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$895,000

Experience elevated living at 58 Cumberland Avenue, Portland's newest boutique development. Nestled atop Munjoy Hill in Portland's vibrant East End and blending timeless craftsmanship with modern sophistication, each residence offers 2 to 3 bedrooms, 2 bathrooms, and open-concept layouts ranging from 1,000 to nearly 1,500 SF. Expansive Marvin windows, 9-foot ceilings, and wide-plank hickory floors create light-filled interiors with a refined sense of space. Unit 1 enjoys a thoughtfully designed living space ideal for entertaining or unwinding in style. The chef-inspired kitchen showcases exquisite custom cherry cabinetry from Cabico, complemented by Vadara Quartz countertops, an elegant tile backsplash, and high end Cafe Series appliances. Spacious and tranquil bedrooms prioritize comfort and privacy, creating a serene retreat. Luxurious bathrooms boast custom Cabico vanities complete with stylish Kohler fixtures, alongside designer tile showers and flooring sourced from Tilebar creating a truly refined yet functional feel. Each energy-efficient, fully electric unit is equipped with Mitsubishi in-ceiling heat pumps, ERV systems, and premium insulation to ensure year-round comfort. The building also offers heated garage parking with EV charging infrastructure for added convenience. Located just steps from the vibrant Washington Ave corridor and Eastern Promenade, residents enjoy seamless access to top restaurants, local shops, and Portland's picturesque waterfront. Experience luxury, location, and lifestyle redefined at 58 Cumberland. For more information, please visit the development section of Portside's website.

2 Beds ⋅ 2 Baths

Experience elevated living at 58 Cumberland Avenue, Portland's newest boutique development. Nestled atop Munjoy Hill in Portland's vibrant East End and blending timeless craftsmanship with modern sophistication, each residence offers 2 to 3 bedrooms, 2 bathrooms, and open-concept layouts ranging from 1,000 to nearly 1,500 SF. Expansive Marvin windows, 9-foot ceilings, and wide-plank hickory floors create light-filled interiors with a refined sense of space. Unit 1 enjoys a thoughtfully designed living space ideal for entertaining or unwinding in style. The chef-inspired kitchen showcases exquisite custom cherry cabinetry from Cabico, complemented by Vadara Quartz countertops, an elegant tile backsplash, and high end Cafe Series appliances. Spacious and tranquil bedrooms prioritize comfort and privacy, creating a serene retreat. Luxurious bathrooms boast custom Cabico vanities complete with stylish Kohler fixtures, alongside designer tile showers and flooring sourced from Tilebar creating a truly refined yet functional feel. Each energy-efficient, fully electric unit is equipped with Mitsubishi in-ceiling heat pumps, ERV systems, and premium insulation to ensure year-round comfort. The building also offers heated garage parking with EV charging infrastructure for added convenience. Located just steps from the vibrant Washington Ave corridor and Eastern Promenade, residents enjoy seamless access to top restaurants, local shops, and Portland's picturesque waterfront. Experience luxury, location, and lifestyle redefined at 58 Cumberland. For more information, please visit the development section of Portside's website.

58 Cumberland Ave Unit 1, Portland

Listing courtesy of Portside Real Estate Group.

$653,000

Historic West End residences of this caliber rarely become available. Thoughtfully restored and beautifully renovated, this distinctive Italianate home blends timeless architectural character with sophisticated modern updates, creating an exceptional space for both everyday living and entertaining. The main level is designed for gathering, featuring elegant living and dining spaces, beautiful original details, hardwood floors, and a beautifully updated kitchen that honors the home's historic character. The private lower level serves as a dedicated bedroom wing, offering three well-appointed bedrooms and updated baths in a thoughtfully integrated design. Located just moments from the heart of Portland's historic West End, you'll enjoy easy access to neighborhood cafés, restaurants, the Western Promenade, Maine Medical Center, and downtown Portland--all while returning home to a residence that offers uncommon character, craftsmanship, and comfort. For buyers seeking authentic historic architecture, exceptional renovation quality, and an in-town lifestyle, this is a rare opportunity to own one of Portland's truly distinctive homes.

3 Beds ⋅ 3 Baths

Historic West End residences of this caliber rarely become available. Thoughtfully restored and beautifully renovated, this distinctive Italianate home blends timeless architectural character with sophisticated modern updates, creating an exceptional space for both everyday living and entertaining. The main level is designed for gathering, featuring elegant living and dining spaces, beautiful original details, hardwood floors, and a beautifully updated kitchen that honors the home's historic character. The private lower level serves as a dedicated bedroom wing, offering three well-appointed bedrooms and updated baths in a thoughtfully integrated design. Located just moments from the heart of Portland's historic West End, you'll enjoy easy access to neighborhood cafés, restaurants, the Western Promenade, Maine Medical Center, and downtown Portland--all while returning home to a residence that offers uncommon character, craftsmanship, and comfort. For buyers seeking authentic historic architecture, exceptional renovation quality, and an in-town lifestyle, this is a rare opportunity to own one of Portland's truly distinctive homes.

20 Dow St Unit 1, Portland

Listing courtesy of Legacy Properties Sotheby's International Realty.

$899,000

Thoughtful design meets the best of downtown living! Verdante's most desirable residences -- a beautifully upgraded two-bedroom, two-bath corner unit with no neighboring units on either side, offering a level of privacy rarely found in condominium living. Soaring 10-foot ceilings and walls of oversized windows flood every room with natural light, while motorized power shades give you effortless control over sun and privacy throughout the day. The open-concept living, dining, and kitchen area is an entertainer's dream. A chef's kitchen anchors the space with quartz countertops, a large island, premium appliances, and a warm subway tile backsplash -- all finished with crisp white shaker cabinetry and black hardware. The living room features a shiplap accent wall with a sleek inset fireplace, and a private balcony just off the dining area extends the living space outdoors. The primary suite is a serene retreat, generous storage, and a spa-caliber en-suite bath with a dual-sink floating vanity, and a glass-enclosed walk-in shower. The second bedroom is equally well-appointed, served by a beautifully finished full bath. Clever built-in storage solutions throughout the unit maximize every square foot. Central air conditioning keeps things comfortable year-round. Parking is handled effortlessly via the building's sophisticated mechanical stacking garage with dedicated bike storage for two-wheel commuters. Verdante's amenity package is equally impressive: a fully equipped fitness center, a stunning rooftop deck with panoramic views of the Portland skyline and church steeples, and great views of the 4th of July Fireworks! A rare perk: a dedicated guest suite available exclusively to unit owners, perfect for visiting family and friends. Step outside and you're already there: the city's best restaurants, coffee shops, the Eastern Promenade, the Old Port, and the East End Beach are all just minutes away on foot. This is Portland living at its most refined.

2 Beds ⋅ 2 Baths

Thoughtful design meets the best of downtown living! Verdante's most desirable residences -- a beautifully upgraded two-bedroom, two-bath corner unit with no neighboring units on either side, offering a level of privacy rarely found in condominium living. Soaring 10-foot ceilings and walls of oversized windows flood every room with natural light, while motorized power shades give you effortless control over sun and privacy throughout the day. The open-concept living, dining, and kitchen area is an entertainer's dream. A chef's kitchen anchors the space with quartz countertops, a large island, premium appliances, and a warm subway tile backsplash -- all finished with crisp white shaker cabinetry and black hardware. The living room features a shiplap accent wall with a sleek inset fireplace, and a private balcony just off the dining area extends the living space outdoors. The primary suite is a serene retreat, generous storage, and a spa-caliber en-suite bath with a dual-sink floating vanity, and a glass-enclosed walk-in shower. The second bedroom is equally well-appointed, served by a beautifully finished full bath. Clever built-in storage solutions throughout the unit maximize every square foot. Central air conditioning keeps things comfortable year-round. Parking is handled effortlessly via the building's sophisticated mechanical stacking garage with dedicated bike storage for two-wheel commuters. Verdante's amenity package is equally impressive: a fully equipped fitness center, a stunning rooftop deck with panoramic views of the Portland skyline and church steeples, and great views of the 4th of July Fireworks! A rare perk: a dedicated guest suite available exclusively to unit owners, perfect for visiting family and friends. Step outside and you're already there: the city's best restaurants, coffee shops, the Eastern Promenade, the Old Port, and the East End Beach are all just minutes away on foot. This is Portland living at its most refined.

99 Federal St Unit 209, Portland

Listing courtesy of The Flaherty Group.

$735,000

Enjoy easy, low maintenance living in Portland's highly desirable Mason Block community. This thoughtfully designed condo offers an efficient and versatile floor plan with an open concept living area with gas fireplace, kitchen with center island, spacious primary bedroom with a customized walk in closet, and a flexible second bedroom that works equally well as a guest room, home office, or den. The private deck extends your living space outdoors, while heat pumps provide efficient heating and air conditioning year round. Building amenities and features include elevator access, covered garage parking, private storage unit, and a beautifully landscaped shared terrace for residents to enjoy. Ideally located in Portland's East End, you'll be just blocks from the waterfront, marinas, restaurants, coffee shops, galleries, museums, and everything downtown Portland has to offer.

2 Beds ⋅ 1 Baths

Enjoy easy, low maintenance living in Portland's highly desirable Mason Block community. This thoughtfully designed condo offers an efficient and versatile floor plan with an open concept living area with gas fireplace, kitchen with center island, spacious primary bedroom with a customized walk in closet, and a flexible second bedroom that works equally well as a guest room, home office, or den. The private deck extends your living space outdoors, while heat pumps provide efficient heating and air conditioning year round. Building amenities and features include elevator access, covered garage parking, private storage unit, and a beautifully landscaped shared terrace for residents to enjoy. Ideally located in Portland's East End, you'll be just blocks from the waterfront, marinas, restaurants, coffee shops, galleries, museums, and everything downtown Portland has to offer.

62 India St Unit 308, Portland

Listing courtesy of Waypoint Brokers Collective.

$675,000

Wow!!! Nothing wrong with this property, off street parking+++ original features, beautiful woodwork that you just don't find in homes these days! Do you like the charm the Colonial Victorian? Come see this property where timeless charm surrounds you. This home has been well maintained and preserved. Exceptional 5-bedroom home showcasing craftsmanship, original woodwork, and timeless architectural character. Beginning in the entry you'll be captivated by the grand staircase, rich millwork and beautiful stained glass. Move right in or take a moment to bring back the woodwork to its original luster and design the kitchen to match your taste! Natural gas fired furnace, newly replaced water heater, updates to the porch, roof and much more. Entertain friends and family in the spacious living and dining rooms, or in the comfortable sitting room. The expansive unfinished third-floor attic presents incredible potential for expansion. Perhaps a future living space, a studio, office or workshop. Additional features include a full length covered front porch, a large driveway.

5 Beds ⋅ 2 Baths

Wow!!! Nothing wrong with this property, off street parking+++ original features, beautiful woodwork that you just don't find in homes these days! Do you like the charm the Colonial Victorian? Come see this property where timeless charm surrounds you. This home has been well maintained and preserved. Exceptional 5-bedroom home showcasing craftsmanship, original woodwork, and timeless architectural character. Beginning in the entry you'll be captivated by the grand staircase, rich millwork and beautiful stained glass. Move right in or take a moment to bring back the woodwork to its original luster and design the kitchen to match your taste! Natural gas fired furnace, newly replaced water heater, updates to the porch, roof and much more. Entertain friends and family in the spacious living and dining rooms, or in the comfortable sitting room. The expansive unfinished third-floor attic presents incredible potential for expansion. Perhaps a future living space, a studio, office or workshop. Additional features include a full length covered front porch, a large driveway.

271 Woodford St, Portland

Listing courtesy of Keller Williams Realty. 207-415-8995

$729,000

Welcome to 248 Pleasant Avenue on Peaks Island, where classic island charm meets comfortable year-round living. Set on a beautifully landscaped lot, this 3-bedroom, 2-bath home offers a spacious covered front porch, fenced yard, fire pit patio, hot tub, and storage shed creating the perfect setting for relaxing or entertaining. Inside, you'll find warm and inviting living spaces filled with natural light, hardwood floors, and a pellet stove that adds both comfort and character. Seasonal glimpses of Casco Bay can be enjoyed from the property, while nearby beaches, scenic walking trails, local restaurants, and ferry access are all within easy reach. Experience the vibrant Peaks Island lifestyle with easy access to the historic TEIA (Trefethen-Evergreen Improvement Association), a cherished community hub offering sailing, tennis, pickleball, youth camps, arts and cultural programs, fitness classes, live music, lectures, and seasonal events that bring neighbors and visitors together. Whether you're seeking a full-time residence, seasonal getaway, or investment opportunity, this home offers the perfect blend of coastal beauty, community, and convenience--just a short ferry ride from Portland.

3 Beds ⋅ 2 Baths

Welcome to 248 Pleasant Avenue on Peaks Island, where classic island charm meets comfortable year-round living. Set on a beautifully landscaped lot, this 3-bedroom, 2-bath home offers a spacious covered front porch, fenced yard, fire pit patio, hot tub, and storage shed creating the perfect setting for relaxing or entertaining. Inside, you'll find warm and inviting living spaces filled with natural light, hardwood floors, and a pellet stove that adds both comfort and character. Seasonal glimpses of Casco Bay can be enjoyed from the property, while nearby beaches, scenic walking trails, local restaurants, and ferry access are all within easy reach. Experience the vibrant Peaks Island lifestyle with easy access to the historic TEIA (Trefethen-Evergreen Improvement Association), a cherished community hub offering sailing, tennis, pickleball, youth camps, arts and cultural programs, fitness classes, live music, lectures, and seasonal events that bring neighbors and visitors together. Whether you're seeking a full-time residence, seasonal getaway, or investment opportunity, this home offers the perfect blend of coastal beauty, community, and convenience--just a short ferry ride from Portland.

248 Pleasant Ave, Portland

Listing courtesy of Berkshire Hathaway HomeServices Verani Realty.

$420,000

Tucked into the heart of the West End, this 2-bedroom condo brings together the architectural soul of one of Portland's most beloved neighborhoods and the thoughtful updates that make everyday living feel effortless. Soaring ceilings, light hardwood floors, and oversized windows fill the space with sun and charm that's hard to find. The primary bedroom is anchored by classic bay windows and opens into a versatile bonus room, equally suited as a walk-in closet, home office, or private exercise space. The renovated kitchen features custom cabinetry and quartz countertops, and the bathroom strikes a clean, modern note. In-unit laundry rounds out the conveniences that make city living easy. Step outside to a private urban oasis with a fire pit, lush plantings, and room to unwind through every Maine season. A caged storage unit in the basement keeps the clutter at bay, and low condo fees that include heat make this an uncommonly smart entry into peninsula living. The Western Promenade, celebrated restaurants, and the neighborhood's signature tree-lined streets are all right outside your door. Open House Sunday 7/19 from 10:00-11:00.

2 Beds ⋅ 1 Baths

Tucked into the heart of the West End, this 2-bedroom condo brings together the architectural soul of one of Portland's most beloved neighborhoods and the thoughtful updates that make everyday living feel effortless. Soaring ceilings, light hardwood floors, and oversized windows fill the space with sun and charm that's hard to find. The primary bedroom is anchored by classic bay windows and opens into a versatile bonus room, equally suited as a walk-in closet, home office, or private exercise space. The renovated kitchen features custom cabinetry and quartz countertops, and the bathroom strikes a clean, modern note. In-unit laundry rounds out the conveniences that make city living easy. Step outside to a private urban oasis with a fire pit, lush plantings, and room to unwind through every Maine season. A caged storage unit in the basement keeps the clutter at bay, and low condo fees that include heat make this an uncommonly smart entry into peninsula living. The Western Promenade, celebrated restaurants, and the neighborhood's signature tree-lined streets are all right outside your door. Open House Sunday 7/19 from 10:00-11:00.

170 Clark St Unit 2, Portland

Listing courtesy of Portside Real Estate Group.

$525,000

In Portland's coveted East End, this corner unit residence is an invitation to experience a lifestyle shaped by harbor light, historic character, and the energy of one of the city's most cherished neighborhoods. Framed by sweeping views of Casco Bay from nearly every room, this home is filled with an ever-changing coastal backdrop. Just steps from the Eastern Promenade, neighborhood cafes, and nationally recognized restaurants, the location offers a rare blend of waterfront tranquility, exceptional walkability and vibrant city living. Equally suited to a lock-and-leave retreat or full-time residence, this is where the very best of East End living comes together in perfect balance.

2 Beds ⋅ 2 Baths

In Portland's coveted East End, this corner unit residence is an invitation to experience a lifestyle shaped by harbor light, historic character, and the energy of one of the city's most cherished neighborhoods. Framed by sweeping views of Casco Bay from nearly every room, this home is filled with an ever-changing coastal backdrop. Just steps from the Eastern Promenade, neighborhood cafes, and nationally recognized restaurants, the location offers a rare blend of waterfront tranquility, exceptional walkability and vibrant city living. Equally suited to a lock-and-leave retreat or full-time residence, this is where the very best of East End living comes together in perfect balance.

45 Eastern Promenade Unit BG, Portland

Listing courtesy of Keller Williams Realty. 207-576-8771

$799,000

Welcome to Chandlers Wharf building 7. A stand alone brick building sited on a private pier in the heart of Portlands Old Port. A premiere waterfront lifestyle awaits you with unobstructed views of lobster boats, yachts and harbor tours. Start your day on your covered balcony watching the sunrise with your morning coffee listening to the cry of the ospreys. The residence is a light filled end unit with expansive windows offering illumination throughout the day. This rare first floor one level condominium also has its own private entrance. An open concept kitchen,dining and living area has been updated recently. The kitchen would delight most chefs with high end appliances and a good amount of counter space. It's an easy walk to a few excellent fish markets. The kitchen is open to the dining and living room area And with over 1000 square feet the space feels spacious and functional. Highlights are a master bedroom suite that really feels private. Plenty of storage with deep closets. The guest bedroom has a bathroom from the hall adjacent to the room. Both bathrooms have been renovated with tile and shiplap. Other amenities include laundry in the unit and an ample entry area with an additional pantry closet. The charm of a working waterfront combined with world class restaurants and boutiques, a vibrant art and music scene make this spot very special whether it is your main residence or pied-a-terre

2 Beds ⋅ 2 Baths

Welcome to Chandlers Wharf building 7. A stand alone brick building sited on a private pier in the heart of Portlands Old Port. A premiere waterfront lifestyle awaits you with unobstructed views of lobster boats, yachts and harbor tours. Start your day on your covered balcony watching the sunrise with your morning coffee listening to the cry of the ospreys. The residence is a light filled end unit with expansive windows offering illumination throughout the day. This rare first floor one level condominium also has its own private entrance. An open concept kitchen,dining and living area has been updated recently. The kitchen would delight most chefs with high end appliances and a good amount of counter space. It's an easy walk to a few excellent fish markets. The kitchen is open to the dining and living room area And with over 1000 square feet the space feels spacious and functional. Highlights are a master bedroom suite that really feels private. Plenty of storage with deep closets. The guest bedroom has a bathroom from the hall adjacent to the room. Both bathrooms have been renovated with tile and shiplap. Other amenities include laundry in the unit and an ample entry area with an additional pantry closet. The charm of a working waterfront combined with world class restaurants and boutiques, a vibrant art and music scene make this spot very special whether it is your main residence or pied-a-terre

703 Chandlers Wharf, Unit 703, Portland

Listing courtesy of RE/MAX Shoreline.

$1,495,000

Buffered by natural beauty and protected land, this remarkable seaside property delights the senses at every turn. The sparkle of the tide, rustle of foliage, salty sea breezes, birdsong, and spectacular sunrises & sunsets create an atmosphere of uncommon tranquility. Set on a generous, sun-drenched lawn just steps from the shore, this 3 BR, 2 BA home blends coastal elegance with timeless cottage architecture. Meticulously maintained, the year-round residence reflects pride of ownership. Water views and natural light grace nearly every room, while quality craftsmanship and tasteful design create spaces that are both beautiful and functional. At the heart of the home, the bright and inviting kitchen encourages effortless gathering. Open to the living and dining areas, it features custom-crafted pantry and buffet cabinetry beneath a vaulted ceiling. A woodstove adds warmth and ambiance on cooler days, while oversized glass sliders frame the picturesque landscape and seamlessly connect the interior to the outdoors. Designed for entertaining and everyday enjoyment alike, the expansive, partially covered deck overlooks the water and extends the living space. Stone patios create inviting destinations for outdoor dining and evening fires by the sea. Whether hosting family & friends or enjoying a quiet moment alone, the setting is simply unforgettable. The primary BR offers a walk-in closet and private balcony w/ outdoor shower overlooking the shoreline. Additional amenities include a 1st flr BR with nearby full BA, a cozy study/artist's nook, 2nd-flr laundry, mud rm. The exterior features high-quality, low-maintenance materials, delightful landscaping, raised garden beds, a charming children's play area complete with sandpit & secret path, and a newly constructed deluxe shed. Enhanced by countless details that elevate it from ordinary to exceptional, this private coastal retreat offers the best of island living. Enjoy easy access to village shops and ferry landing.

3 Beds ⋅ 2 Baths

Buffered by natural beauty and protected land, this remarkable seaside property delights the senses at every turn. The sparkle of the tide, rustle of foliage, salty sea breezes, birdsong, and spectacular sunrises & sunsets create an atmosphere of uncommon tranquility. Set on a generous, sun-drenched lawn just steps from the shore, this 3 BR, 2 BA home blends coastal elegance with timeless cottage architecture. Meticulously maintained, the year-round residence reflects pride of ownership. Water views and natural light grace nearly every room, while quality craftsmanship and tasteful design create spaces that are both beautiful and functional. At the heart of the home, the bright and inviting kitchen encourages effortless gathering. Open to the living and dining areas, it features custom-crafted pantry and buffet cabinetry beneath a vaulted ceiling. A woodstove adds warmth and ambiance on cooler days, while oversized glass sliders frame the picturesque landscape and seamlessly connect the interior to the outdoors. Designed for entertaining and everyday enjoyment alike, the expansive, partially covered deck overlooks the water and extends the living space. Stone patios create inviting destinations for outdoor dining and evening fires by the sea. Whether hosting family & friends or enjoying a quiet moment alone, the setting is simply unforgettable. The primary BR offers a walk-in closet and private balcony w/ outdoor shower overlooking the shoreline. Additional amenities include a 1st flr BR with nearby full BA, a cozy study/artist's nook, 2nd-flr laundry, mud rm. The exterior features high-quality, low-maintenance materials, delightful landscaping, raised garden beds, a charming children's play area complete with sandpit & secret path, and a newly constructed deluxe shed. Enhanced by countless details that elevate it from ordinary to exceptional, this private coastal retreat offers the best of island living. Enjoy easy access to village shops and ferry landing.

17 3rd St, Portland

Listing courtesy of Portside Real Estate Group.

$799,900

Set above Portland's Eastern Promenade on the 5th floor, this condo is all about the view. Expansive windows span the living and dining areas, drawing in sweeping views over Back Cove where sunsets become part of the nightly routine and on especially clear days, even Mount Washington makes an appearance on the horizon. The updated kitchen offers a modern, functional design with generous cabinet storage and seamless connection to the main living spaces. Two bedrooms, two baths and in-unit laundry complete this unit. Please note that the association maintains a NO dog policy. Residents enjoy access to a covered parking spot, a heated outdoor pool, fitness room, library, and spacious community room. With convenient access to the Eastern Prom trails, East End Beach, and Portland's celebrated food scene, this location offers an easy connection to some of the city's best waterfront and downtown amenities.

2 Beds ⋅ 2 Baths

Set above Portland's Eastern Promenade on the 5th floor, this condo is all about the view. Expansive windows span the living and dining areas, drawing in sweeping views over Back Cove where sunsets become part of the nightly routine and on especially clear days, even Mount Washington makes an appearance on the horizon. The updated kitchen offers a modern, functional design with generous cabinet storage and seamless connection to the main living spaces. Two bedrooms, two baths and in-unit laundry complete this unit. Please note that the association maintains a NO dog policy. Residents enjoy access to a covered parking spot, a heated outdoor pool, fitness room, library, and spacious community room. With convenient access to the Eastern Prom trails, East End Beach, and Portland's celebrated food scene, this location offers an easy connection to some of the city's best waterfront and downtown amenities.

340 Eastern Promenade Unit 252, Portland

Listing courtesy of Portside Real Estate Group.

$660,000

Location, Luxury, and More Space to Breathe! Welcome home to this pristine, one-of-a-kind one-bedroom condo sitting right in the vibrant heart of the Portland peninsula. Offered by its original owner and kept in absolutely immaculate condition, this unit isn't just another condo--it's a step up from the rest. If you've been wishing for a little bit more, this is the one you've been waiting for. It boasts a larger footprint, a brighter atmosphere, and high-end upgrades that truly set it apart. Notably larger than standard one-bedroom units in the building, this unit is flooded with natural light thanks to the extra windows. The owner also spared no expense on the kitchen, adding additional custom cabinetry and equipping the space with top-of-the-line, premium appliances. The dining area features custom built-in seating, creating the perfect cozy spot for morning coffee or hosting intimate dinner parties. Situated in a quiet section of the building, you get all the perks of downtown living without any of the hustle-and-bustle noise. Relax on your private balcony to enjoy your morning coffee or unwind after a busy day. This unit also comes with its own dedicated single-car parking space. It simply has more of everything a discerning owner wants: more square footage, great storage, superior finishes, and a peaceful vibe in a premium location. Seller is willing to entertain leaving the furnishings.

1 Beds ⋅ 1 Baths

Location, Luxury, and More Space to Breathe! Welcome home to this pristine, one-of-a-kind one-bedroom condo sitting right in the vibrant heart of the Portland peninsula. Offered by its original owner and kept in absolutely immaculate condition, this unit isn't just another condo--it's a step up from the rest. If you've been wishing for a little bit more, this is the one you've been waiting for. It boasts a larger footprint, a brighter atmosphere, and high-end upgrades that truly set it apart. Notably larger than standard one-bedroom units in the building, this unit is flooded with natural light thanks to the extra windows. The owner also spared no expense on the kitchen, adding additional custom cabinetry and equipping the space with top-of-the-line, premium appliances. The dining area features custom built-in seating, creating the perfect cozy spot for morning coffee or hosting intimate dinner parties. Situated in a quiet section of the building, you get all the perks of downtown living without any of the hustle-and-bustle noise. Relax on your private balcony to enjoy your morning coffee or unwind after a busy day. This unit also comes with its own dedicated single-car parking space. It simply has more of everything a discerning owner wants: more square footage, great storage, superior finishes, and a peaceful vibe in a premium location. Seller is willing to entertain leaving the furnishings.

113 Newbury St Unit 206, Portland

Listing courtesy of Portside Real Estate Group.

$591,599

Step into the perfect blend of timeless charm and modern convenience in this beautifully maintained 1919 Gambrel-style home on Presumpscot Street in Portland. Featuring 4 bedrooms and 2 bathrooms, this home features a thoughtfully designed layout with a first-floor bedroom, full bath, and laundry--ideal for single-level living or accommodating guests. The inviting farmer's porch welcomes you home and flows into a cozy living room filled with character and warmth. A designated dining room provides the perfect setting for gatherings, while the kitchen seamlessly combines classic charm with modern functionality. Throughout the home, you'll find a wonderful balance of original details and tasteful updates. Upstairs, three spacious bedrooms and a full bathroom provide comfortable living space for bedrooms, guests, or a home office setup. Enjoy abundant storage with separate full basements under both the original home and the addition. Outside, enjoy a beautifully landscaped, level 0.12-acre lot with open yard space perfect for gardening, entertaining, or simply relaxing. Conveniently located under 10 minutes from Portland's vibrant Old Port and downtown districts, this home offers easy access to local restaurants, shops, and waterfront attractions. Outdoor enthusiasts will appreciate the proximity to the Presumpscot River Preserve, Back Cove Trail, and miles of walking, running, and biking trails, along with nearby parks, golf courses, and recreational opportunities. A rare opportunity to own a piece of Portland history while enjoying the conveniences of modern living in one of Maine's most desirable cities. Open House Saturday July 25th from 11:30am-1pm.

4 Beds ⋅ 2 Baths

Step into the perfect blend of timeless charm and modern convenience in this beautifully maintained 1919 Gambrel-style home on Presumpscot Street in Portland. Featuring 4 bedrooms and 2 bathrooms, this home features a thoughtfully designed layout with a first-floor bedroom, full bath, and laundry--ideal for single-level living or accommodating guests. The inviting farmer's porch welcomes you home and flows into a cozy living room filled with character and warmth. A designated dining room provides the perfect setting for gatherings, while the kitchen seamlessly combines classic charm with modern functionality. Throughout the home, you'll find a wonderful balance of original details and tasteful updates. Upstairs, three spacious bedrooms and a full bathroom provide comfortable living space for bedrooms, guests, or a home office setup. Enjoy abundant storage with separate full basements under both the original home and the addition. Outside, enjoy a beautifully landscaped, level 0.12-acre lot with open yard space perfect for gardening, entertaining, or simply relaxing. Conveniently located under 10 minutes from Portland's vibrant Old Port and downtown districts, this home offers easy access to local restaurants, shops, and waterfront attractions. Outdoor enthusiasts will appreciate the proximity to the Presumpscot River Preserve, Back Cove Trail, and miles of walking, running, and biking trails, along with nearby parks, golf courses, and recreational opportunities. A rare opportunity to own a piece of Portland history while enjoying the conveniences of modern living in one of Maine's most desirable cities. Open House Saturday July 25th from 11:30am-1pm.

64 Presumpscot St, Portland

Listing courtesy of Keller Williams Coastal and Lakes & Mountains Realty.

$499,000

OPEN HOUSE SATURDAY 7/11/26 - 11am-1pm Experience the best of Portland's East End neighborhood in this spacious and inviting one-bedroom condo featuring breathtaking views of the Atlantic Ocean and unforgettable sunrises. Nestled in a quiet, well maintained building on a corner lot, this rare offering combines comfort, convenience, and investment potential in one of Portland's most sought-after neighborhoods. Inside, you'll find an expansive open layout featuring beautiful wood floors throughout, a generously sized bedroom, and a large living room. The well appointed kitchen flows seamlessly in to a cozy dining space, sitting area and office nook, designed to maximize both space and natural light. Enjoy your morning coffee while watching the sun rise over the water, then take advantage of the property's shared outdoor patio and garden amenity. A short stroll to neighborhood coffee shops, acclaimed restaurants, and Portland's vibrant Old Port District, there is plenty to explore just steps from the door. Whether you're seeking a primary residence, a second home, or an investment property, this condo offers exceptional flexibility with an HOA that allows rentals. Additional highlights include an efficient gas heating system with a recently updated boiler, updated appliances, in-unit laundry, and ample storage space. Don't miss this rare opportunity to own a piece of Portland's coveted East End lifestyle.

1 Beds ⋅ 1 Baths

OPEN HOUSE SATURDAY 7/11/26 - 11am-1pm Experience the best of Portland's East End neighborhood in this spacious and inviting one-bedroom condo featuring breathtaking views of the Atlantic Ocean and unforgettable sunrises. Nestled in a quiet, well maintained building on a corner lot, this rare offering combines comfort, convenience, and investment potential in one of Portland's most sought-after neighborhoods. Inside, you'll find an expansive open layout featuring beautiful wood floors throughout, a generously sized bedroom, and a large living room. The well appointed kitchen flows seamlessly in to a cozy dining space, sitting area and office nook, designed to maximize both space and natural light. Enjoy your morning coffee while watching the sun rise over the water, then take advantage of the property's shared outdoor patio and garden amenity. A short stroll to neighborhood coffee shops, acclaimed restaurants, and Portland's vibrant Old Port District, there is plenty to explore just steps from the door. Whether you're seeking a primary residence, a second home, or an investment property, this condo offers exceptional flexibility with an HOA that allows rentals. Additional highlights include an efficient gas heating system with a recently updated boiler, updated appliances, in-unit laundry, and ample storage space. Don't miss this rare opportunity to own a piece of Portland's coveted East End lifestyle.

16-18 Cumberland Ave Unit 4, Portland

Listing courtesy of Keller Williams Realty.

$525,000

A MUST SEE!! THE MONTHLY CONDO DUES INCLUDE ACCESS TO THE BEAUTIFUL NEW POOL AREA. PICKLE BALL AND TENNIS COURTS. EXTRA AMENITIES ARE CABLE, INTERNET AND TRASH REMOVAL - ADDING TREMEDOUS VALUE AND CONVENIENCE. ONE OF THE BEST POND VIEWS IN THE COMMUNITY RIGHT IN YOUR OWN BACK YARD!! Enjoy serene pond views from this sunny and beautifully updated 2-bedroom, 2.5 bath condo in desirable Parsons Pond. Known for its peaceful setting, this home features an updated kitchen, renovated baths and newer flooring throughout. Stay comfortable year-round with efficient heat pumps providing both heating and air conditioning, while the cozy fireplace adds warmth and charm to the living space. The spacious primary bedroom includes its own private bath and the convenience of second-floor laundry adds to the home's functional layout. Enjoy our private deck overlooking the peaceful pond, perfect for relaxing or entertaining. Additional features include a one-car garage a third-floor unfinished loft offering great potential for extra living space, a home office or storage. Residents enjoy access to desirable amenities including a swimming pool, tennis courts and pickleball courts. conveniently located just minutes from Portland's dining, shopping and everyday amenities, this condo offers the perfect blend of comfort, convenience and tranquility. OPEN HOUSE AUGUST 2ND 10AM-12PM

2 Beds ⋅ 3 Baths

A MUST SEE!! THE MONTHLY CONDO DUES INCLUDE ACCESS TO THE BEAUTIFUL NEW POOL AREA. PICKLE BALL AND TENNIS COURTS. EXTRA AMENITIES ARE CABLE, INTERNET AND TRASH REMOVAL - ADDING TREMEDOUS VALUE AND CONVENIENCE. ONE OF THE BEST POND VIEWS IN THE COMMUNITY RIGHT IN YOUR OWN BACK YARD!! Enjoy serene pond views from this sunny and beautifully updated 2-bedroom, 2.5 bath condo in desirable Parsons Pond. Known for its peaceful setting, this home features an updated kitchen, renovated baths and newer flooring throughout. Stay comfortable year-round with efficient heat pumps providing both heating and air conditioning, while the cozy fireplace adds warmth and charm to the living space. The spacious primary bedroom includes its own private bath and the convenience of second-floor laundry adds to the home's functional layout. Enjoy our private deck overlooking the peaceful pond, perfect for relaxing or entertaining. Additional features include a one-car garage a third-floor unfinished loft offering great potential for extra living space, a home office or storage. Residents enjoy access to desirable amenities including a swimming pool, tennis courts and pickleball courts. conveniently located just minutes from Portland's dining, shopping and everyday amenities, this condo offers the perfect blend of comfort, convenience and tranquility. OPEN HOUSE AUGUST 2ND 10AM-12PM

59 Parsons Pond Dr Unit 4205, Portland

Listing courtesy of Greater Portland Realty.

$2,200,000

Stunning 6th floor condo with three bedrooms, three full bathrooms and sparkling water views, located in the heart of the historic Portland waterfront. This rare and pristine 2,064sf unit offers numerous sophisticated upgrades including high end appliances, thoughtfully curated built-ins throughout, gorgeous floor to ceiling stonework surrounding the gas fireplace, a custom bar, designer lighting, deeded garage parking, private storage unit. Amenity-laden building includes a concierge, spacious community room with full kitchen and balcony, mailroom, fitness room, reservable guest suite, shared work/study space, dog wash, and 2 large landscaped courtyards. Just steps away, enjoy award-winning dining, boutique shopping, museums, art galleries, theater, boat tours to the islands and beyond. Don't miss this extraordinary offering!

3 Beds ⋅ 3 Baths

Stunning 6th floor condo with three bedrooms, three full bathrooms and sparkling water views, located in the heart of the historic Portland waterfront. This rare and pristine 2,064sf unit offers numerous sophisticated upgrades including high end appliances, thoughtfully curated built-ins throughout, gorgeous floor to ceiling stonework surrounding the gas fireplace, a custom bar, designer lighting, deeded garage parking, private storage unit. Amenity-laden building includes a concierge, spacious community room with full kitchen and balcony, mailroom, fitness room, reservable guest suite, shared work/study space, dog wash, and 2 large landscaped courtyards. Just steps away, enjoy award-winning dining, boutique shopping, museums, art galleries, theater, boat tours to the islands and beyond. Don't miss this extraordinary offering!

383 Commercial St Unit 603, Portland

Listing courtesy of Town & Shore Real Estate. 207-773-0262

$1,100,000

A breath of fresh air, a step above, one of a kind, welcome to 4 Oramel. Set on nearly an acre and a half and surrounded by protected land abutting parks and trails it is hard to believe you are just moments away from downtown Portland. Thoughtfully developed to match the natural landscape, the home seamlessly blends modern farmhouse with mid-century modern design throughout. Frenking Building Company is a design-forward building company specializing in high end finish carpentry with an approach rooted in simplicity. This 3 bedroom, 2.5 bathroom home surrounded by a gorgeous natural backdrop offers clean lines, natural materials and pallets, and a floor-plan that flows effortlessly inside and out. Stepping inside you will immediately be taken with the attention to detail in every aspect of the design and finish. Custom built cabinetry, simple yet sophisticated tile choices, natural woods throughout, incredible windows and doors, venetian plaster detail, and the incredible wrap around porch. If you have been searching for a truly special property with privacy that doesn't sacrifice convenience, where spaces are soaked in natural light, and where you can be close to nature, you will find it here.

3 Beds ⋅ 3 Baths

A breath of fresh air, a step above, one of a kind, welcome to 4 Oramel. Set on nearly an acre and a half and surrounded by protected land abutting parks and trails it is hard to believe you are just moments away from downtown Portland. Thoughtfully developed to match the natural landscape, the home seamlessly blends modern farmhouse with mid-century modern design throughout. Frenking Building Company is a design-forward building company specializing in high end finish carpentry with an approach rooted in simplicity. This 3 bedroom, 2.5 bathroom home surrounded by a gorgeous natural backdrop offers clean lines, natural materials and pallets, and a floor-plan that flows effortlessly inside and out. Stepping inside you will immediately be taken with the attention to detail in every aspect of the design and finish. Custom built cabinetry, simple yet sophisticated tile choices, natural woods throughout, incredible windows and doors, venetian plaster detail, and the incredible wrap around porch. If you have been searching for a truly special property with privacy that doesn't sacrifice convenience, where spaces are soaked in natural light, and where you can be close to nature, you will find it here.

4 Oramel Ave, Portland

Listing courtesy of Portside Real Estate Group.

$729,000

Welcome to 495 Allen Avenue - a rare opportunity to own a versatile move-in-ready property in Portland's convenient North Deering neighborhood. This 2,200 sqft property includes the 2BD/2BA main house and a 1BD/1BA Accessory Dwelling Unit (ADU). The ADU offers multigenerational living, guest quarters, and potential for rental income. Outside, enjoy a spacious backyard ideal for entertaining, gardening, and relaxing during Maine summers, plus ample off-street parking. Conveniently located just minutes from Shaw's, Northgate Plaza, restaurants, coffee shops, and local favorite Lib's Dairy Treats, with downtown Portland and Falmouth only about 15 minutes away. Whether you're looking for extra space, income potential, or a smart investment in a prime Portland location, 495 Allen Avenue delivers opportunity and convenience.

3 Beds ⋅ 3 Baths

Welcome to 495 Allen Avenue - a rare opportunity to own a versatile move-in-ready property in Portland's convenient North Deering neighborhood. This 2,200 sqft property includes the 2BD/2BA main house and a 1BD/1BA Accessory Dwelling Unit (ADU). The ADU offers multigenerational living, guest quarters, and potential for rental income. Outside, enjoy a spacious backyard ideal for entertaining, gardening, and relaxing during Maine summers, plus ample off-street parking. Conveniently located just minutes from Shaw's, Northgate Plaza, restaurants, coffee shops, and local favorite Lib's Dairy Treats, with downtown Portland and Falmouth only about 15 minutes away. Whether you're looking for extra space, income potential, or a smart investment in a prime Portland location, 495 Allen Avenue delivers opportunity and convenience.

495 Allen Ave, Portland

Listing courtesy of Elevate Maine Realty.

$574,900

Thoughtfully designed with simple living in mind, this 3 bedroom, 2.5 bathroom home features an open-concept layout that blends comfort, style, and functionality. The kitchen is the heart of the home, complete with granite countertops, stainless steel appliances, sleek cabinetry, pantry and a large center island perfect for gathering and entertaining. Upstairs, you'll find a large primary suite with a beautifully finished en-suite bath, along with two additional bedrooms, a full guest bathroom, and convenient second-floor laundry. Situated just minutes from Westbrook's vibrant downtown, local parks, schools, and a quick drive to Portland, this home offers the perfect combination of suburban comfort and city convenience. Don't miss the opportunity to own a brand-new home in one of Southern Maine's most growing communities!

3 Beds ⋅ 3 Baths

Thoughtfully designed with simple living in mind, this 3 bedroom, 2.5 bathroom home features an open-concept layout that blends comfort, style, and functionality. The kitchen is the heart of the home, complete with granite countertops, stainless steel appliances, sleek cabinetry, pantry and a large center island perfect for gathering and entertaining. Upstairs, you'll find a large primary suite with a beautifully finished en-suite bath, along with two additional bedrooms, a full guest bathroom, and convenient second-floor laundry. Situated just minutes from Westbrook's vibrant downtown, local parks, schools, and a quick drive to Portland, this home offers the perfect combination of suburban comfort and city convenience. Don't miss the opportunity to own a brand-new home in one of Southern Maine's most growing communities!

15 Lane Ave, Portland

Listing courtesy of Dan Anderson Real Estate, Inc..

$459,000

Welcome to 29 Brook Road, a charming 3-4 bedroom Cape tucked into Portland's desirable North Deering neighborhood. Full of warmth and everyday comfort, this inviting home offers a flexible layout that can easily adapt to a variety of needs. Inside, you'll find hardwood, tile, and carpeted flooring, a bright, sun-filled living room, and a spacious eat-in kitchen with ample cabinet storage. The floor plan includes a first-floor bedroom, a full bath, and an additional room that can serve as a playroom, home office, formal dining room, or fourth bedroom. A back mudroom with windows overlooking the partially fenced backyard adds both charm and function, while the layout also offers the convenience of single-level living if desired. Upstairs, two bedrooms with newer windows provide cozy, private spaces for family or guests. Notable updates include a Buderus boiler installed in 2015, a roof replaced in 2016, and rebuilt back stairs. Built in 1941, the home also features a full basement with room for storage, hobbies, or future finished space, a covered patio for outdoor relaxation, and a one-car garage with electricity and a remote door opener. Set on a manageable lot with a paved driveway, this property is conveniently located near schools, shopping, restaurants, trails, and downtown Portland. A wonderful opportunity to create a home filled with comfort, connection, and your own personal touch.

3 Beds ⋅ 1 Baths

Welcome to 29 Brook Road, a charming 3-4 bedroom Cape tucked into Portland's desirable North Deering neighborhood. Full of warmth and everyday comfort, this inviting home offers a flexible layout that can easily adapt to a variety of needs. Inside, you'll find hardwood, tile, and carpeted flooring, a bright, sun-filled living room, and a spacious eat-in kitchen with ample cabinet storage. The floor plan includes a first-floor bedroom, a full bath, and an additional room that can serve as a playroom, home office, formal dining room, or fourth bedroom. A back mudroom with windows overlooking the partially fenced backyard adds both charm and function, while the layout also offers the convenience of single-level living if desired. Upstairs, two bedrooms with newer windows provide cozy, private spaces for family or guests. Notable updates include a Buderus boiler installed in 2015, a roof replaced in 2016, and rebuilt back stairs. Built in 1941, the home also features a full basement with room for storage, hobbies, or future finished space, a covered patio for outdoor relaxation, and a one-car garage with electricity and a remote door opener. Set on a manageable lot with a paved driveway, this property is conveniently located near schools, shopping, restaurants, trails, and downtown Portland. A wonderful opportunity to create a home filled with comfort, connection, and your own personal touch.

29 Brook Rd, Portland

Listing courtesy of Gardner Real Estate Group.

$650,000

Exceptional value with this Munjoy Hill condo! 1,640 sq.ft. of living space, 3 bedrooms, 3 bathrooms and gorgeous views of Casco Bay! Hardwood and tile floors throughout, 2 primary suites with private baths, updated appliances and a lot of in unit storage. The Portland House offers unprecedented amenities including heated garage parking, concierge, onsite gym, most utilities are included (cable/internet services, heat, hot water, water/sewer) and onsite maintenance. All this next to Portlands most beautiful city park on the Eastern Prom with over 70 acres of public space stretching around Casco Bay. Don't miss this opportunity!

3 Beds ⋅ 3 Baths

Exceptional value with this Munjoy Hill condo! 1,640 sq.ft. of living space, 3 bedrooms, 3 bathrooms and gorgeous views of Casco Bay! Hardwood and tile floors throughout, 2 primary suites with private baths, updated appliances and a lot of in unit storage. The Portland House offers unprecedented amenities including heated garage parking, concierge, onsite gym, most utilities are included (cable/internet services, heat, hot water, water/sewer) and onsite maintenance. All this next to Portlands most beautiful city park on the Eastern Prom with over 70 acres of public space stretching around Casco Bay. Don't miss this opportunity!

45 Eastern Promenade Unit 2H, Portland

Listing courtesy of Gardner Real Estate Group.

$990,000

Nestled in the heart of Portland's highly sought-after West End, this exceptional property is sure to charm investors and those seeking multi-generational living in a city setting. Currently operating as a highly successful Airbnb, the next owner could continue to make income from one or both of the living spaces, or owner occupy and utilize the first floor unit as an in-law suite. The spacious primary home features 4 bedrooms plus an office and 3 full bathrooms across three floors. Thoughtfully updated, the main home features a custom kitchen and inviting living spaces where soaring cathedral ceilings, exposed wood beams, and skylights create an airy yet cozy atmosphere, filling the kitchen and living room with beautiful natural light and architectural charm. Other standout features include a custom antique bar, wainscoting along the main staircase with a beautifully preserved original banister, and a private deck with low maintenance composite decking. The first floor bedroom is currently used as a home studio office with its own full bathroom. The secondary one bedroom, one bath unit is an easy one level living set up, all on the first floor. The full basement is available for storage. Built in 1874 and offering 2,634 square feet of living space, this West End gem is made even more special by amenities rarely found in the city: a private courtyard perfect for relaxing or entertaining, space for a city garden, and coveted off-street parking. Just moments from Portland's renowned restaurants, shops, hospitals, and waterfront, this is a rare opportunity to own a piece of Portland history.

5 Beds ⋅ 4 Baths

Nestled in the heart of Portland's highly sought-after West End, this exceptional property is sure to charm investors and those seeking multi-generational living in a city setting. Currently operating as a highly successful Airbnb, the next owner could continue to make income from one or both of the living spaces, or owner occupy and utilize the first floor unit as an in-law suite. The spacious primary home features 4 bedrooms plus an office and 3 full bathrooms across three floors. Thoughtfully updated, the main home features a custom kitchen and inviting living spaces where soaring cathedral ceilings, exposed wood beams, and skylights create an airy yet cozy atmosphere, filling the kitchen and living room with beautiful natural light and architectural charm. Other standout features include a custom antique bar, wainscoting along the main staircase with a beautifully preserved original banister, and a private deck with low maintenance composite decking. The first floor bedroom is currently used as a home studio office with its own full bathroom. The secondary one bedroom, one bath unit is an easy one level living set up, all on the first floor. The full basement is available for storage. Built in 1874 and offering 2,634 square feet of living space, this West End gem is made even more special by amenities rarely found in the city: a private courtyard perfect for relaxing or entertaining, space for a city garden, and coveted off-street parking. Just moments from Portland's renowned restaurants, shops, hospitals, and waterfront, this is a rare opportunity to own a piece of Portland history.

75 Carleton St, Portland

Listing courtesy of Maine Real Estate Co.

$990,000

Nestled in the heart of Portland's highly sought-after West End, this exceptional property has charm, comfort, and outstanding income potential. Currently operating as a highly successful Airbnb, this versatile two unit property offers endless possibilities for investors, owner-occupants, or those seeking multi-generational living in a city setting. The spacious primary living space features 4 bedrooms plus an office and 3 full bathrooms across three floors. Thoughtfully updated, the main home features a custom kitchen and inviting living spaces where soaring cathedral ceilings, exposed wood beams, and skylights create an airy yet cozy atmosphere, filling the kitchen and living room with beautiful natural light and architectural charm. Other standout features include a custom antique bar, wainscoting along the main staircase with a beautifully preserved original banister, and a private deck with low maintenance composite decking. The first floor bedroom is currently used as a home studio office with its own full bathroom. The secondary unit includes an oversized 1-bedroom, 1-bath layout, ideal for guests, rental income, or extended stays. The one bedroom is an easy one level living set up, all on the first floor. The full basement is available for storage. Built in 1874 and offering 2,634 square feet of living space, this West End gem is made even more special by amenities rarely found in the city: a private courtyard perfect for relaxing or entertaining, space for a city garden, and coveted off-street parking. Just moments from Portland's renowned restaurants, shops, hospitals, and waterfront, this is a rare opportunity to own a piece of Portland history with proven income performance and an inviting feel that keeps guests coming back.

4 Baths

Nestled in the heart of Portland's highly sought-after West End, this exceptional property has charm, comfort, and outstanding income potential. Currently operating as a highly successful Airbnb, this versatile two unit property offers endless possibilities for investors, owner-occupants, or those seeking multi-generational living in a city setting. The spacious primary living space features 4 bedrooms plus an office and 3 full bathrooms across three floors. Thoughtfully updated, the main home features a custom kitchen and inviting living spaces where soaring cathedral ceilings, exposed wood beams, and skylights create an airy yet cozy atmosphere, filling the kitchen and living room with beautiful natural light and architectural charm. Other standout features include a custom antique bar, wainscoting along the main staircase with a beautifully preserved original banister, and a private deck with low maintenance composite decking. The first floor bedroom is currently used as a home studio office with its own full bathroom. The secondary unit includes an oversized 1-bedroom, 1-bath layout, ideal for guests, rental income, or extended stays. The one bedroom is an easy one level living set up, all on the first floor. The full basement is available for storage. Built in 1874 and offering 2,634 square feet of living space, this West End gem is made even more special by amenities rarely found in the city: a private courtyard perfect for relaxing or entertaining, space for a city garden, and coveted off-street parking. Just moments from Portland's renowned restaurants, shops, hospitals, and waterfront, this is a rare opportunity to own a piece of Portland history with proven income performance and an inviting feel that keeps guests coming back.

75 Carleton St, Portland

Listing courtesy of Maine Real Estate Co.

$549,000

Welcome to 199 Vaughan Street #4, a classic Portland West End condominium full of charm, character, and timeless appeal. Situated in a beautifully maintained historic brick building, this spacious 3 bedroom condo offers the perfect blend of original architectural details and comfortable everyday living. Inside, you'll find hardwood floors, high ceilings, oversized windows bringing in natural sunlight, and a warm fireplace that anchors the living space. The layout offers flexibility for working from home, hosting guests, or simply enjoying city living with room to spread out. A private deck, generous storage space, and coveted off street parking add to the convenience. Located just steps from the Western Promenade, Maine Medical Center, local coffee shops, restaurants, and everything Portland has to provide, this home places you right in the heart of one of the city's most desirable neighborhoods. Historic charm, walkability, and easy peninsula living all come together at 199 Vaughan Street #4.

3 Beds ⋅ 1 Baths

Welcome to 199 Vaughan Street #4, a classic Portland West End condominium full of charm, character, and timeless appeal. Situated in a beautifully maintained historic brick building, this spacious 3 bedroom condo offers the perfect blend of original architectural details and comfortable everyday living. Inside, you'll find hardwood floors, high ceilings, oversized windows bringing in natural sunlight, and a warm fireplace that anchors the living space. The layout offers flexibility for working from home, hosting guests, or simply enjoying city living with room to spread out. A private deck, generous storage space, and coveted off street parking add to the convenience. Located just steps from the Western Promenade, Maine Medical Center, local coffee shops, restaurants, and everything Portland has to provide, this home places you right in the heart of one of the city's most desirable neighborhoods. Historic charm, walkability, and easy peninsula living all come together at 199 Vaughan Street #4.

199 Vaughan St Unit 4, Portland

Listing courtesy of Benchmark Real Estate.

$832,283

Life Re-Imagined! Building 3, Stevens Square at Baxter Woods! This growing new neighborhood is on its way to be one of the most exciting places to live in Portland Maine! Stevens Square represents Portland's first 55+ condominium community adjacent to hundreds of acres of woods and walking trails. Complete with convenient dog washes, crackling fire pits, and available community center with saltwater pool and gym, this 4th floor south facing unit has it all. Nicely balanced living spaces focused with designer chosen appointments, including ensuite bedrooms, private deck and lots of wonderful light. This unit faces the beautiful and protected Baxter Woods. Enjoy the large gathering room and sky deck at your fingertips. Covered parking and storage also included. A well-rounded life begins at the Square!

2 Beds ⋅ 2 Baths

Life Re-Imagined! Building 3, Stevens Square at Baxter Woods! This growing new neighborhood is on its way to be one of the most exciting places to live in Portland Maine! Stevens Square represents Portland's first 55+ condominium community adjacent to hundreds of acres of woods and walking trails. Complete with convenient dog washes, crackling fire pits, and available community center with saltwater pool and gym, this 4th floor south facing unit has it all. Nicely balanced living spaces focused with designer chosen appointments, including ensuite bedrooms, private deck and lots of wonderful light. This unit faces the beautiful and protected Baxter Woods. Enjoy the large gathering room and sky deck at your fingertips. Covered parking and storage also included. A well-rounded life begins at the Square!

75 Mcauley Way Unit 305, Portland

Listing courtesy of Gardner Real Estate Group.

$268,800

Be the first to live in this brand-new, zero-energy-ready 1BR condo at Dougherty Commons by Maine Cooperative Development Partners. Move-in ready now. This stylish first-floor home features a private no-step entrance, high ceilings, large windows, wide doorways, a step-in shower, and roll-under kitchen counters -- thoughtfully designed for easy, comfortable living. Enjoy a modern kitchen with new stainless-steel appliances, a bright open layout, and in-unit washer/dryer hookups. Energy-efficient and low-maintenance, this home is perfect for a first-time buyer, downsizer, or anyone wanting a beautifully designed space close to everything Portland offers. Located next to Dougherty Fields (playground, outdoor pool, skate park, sports fields, basketball court). The #1, #4, #5, #7 & #9 Metro & Breez bus lines, Amtrak Downeaster, and Concord Coach are within .5 mile. Income-qualified: up to $90,900/year for one person, or $103,850 for two -- only the buyer on the deed needs to meet the income limit. Deed-restricted to keep this home permanently affordable for future buyers, too.

1 Beds ⋅ 1 Baths

Be the first to live in this brand-new, zero-energy-ready 1BR condo at Dougherty Commons by Maine Cooperative Development Partners. Move-in ready now. This stylish first-floor home features a private no-step entrance, high ceilings, large windows, wide doorways, a step-in shower, and roll-under kitchen counters -- thoughtfully designed for easy, comfortable living. Enjoy a modern kitchen with new stainless-steel appliances, a bright open layout, and in-unit washer/dryer hookups. Energy-efficient and low-maintenance, this home is perfect for a first-time buyer, downsizer, or anyone wanting a beautifully designed space close to everything Portland offers. Located next to Dougherty Fields (playground, outdoor pool, skate park, sports fields, basketball court). The #1, #4, #5, #7 & #9 Metro & Breez bus lines, Amtrak Downeaster, and Concord Coach are within .5 mile. Income-qualified: up to $90,900/year for one person, or $103,850 for two -- only the buyer on the deed needs to meet the income limit. Deed-restricted to keep this home permanently affordable for future buyers, too.

65 Dougherty Ct Unit 101, Portland

Listing courtesy of www.HomeZu.com. 877-249-5478

$234,900

Recently approved building lots in North Deering! Zoning allows for up to 4 units on each lot. Lot 1 of two lots available. See MLS 1652546

1551 Washington Avenue Extension, Portland

Listing courtesy of The Flaherty Group.

$435,000

New price. Well-located 2-bedroom, 1-bath Portland condominium in the sought-after Deering/Rosemont area. This first-floor unit features hardwood floors, a recently renovated bathroom, private washer/dryer, private storage, a private shed, and two dedicated off-street parking spaces. A ducted heat pump system provides efficient heating and cooling with vents to multiple rooms, with boiler back-up for added comfort. Enjoy a large fenced backyard with a patio, fire pit, grill area, and plenty of space for relaxing, gardening, or entertaining. Pet-friendly association. Conveniently located near Deering High School, UNE, USM, Rosemont Market, local restaurants, Maine Medical Center, and Northern Light Mercy Hospital. Outdoor enthusiasts will appreciate nearby Evergreen Woods, offering approximately 4 miles of trails. An appealing opportunity to own a first-floor Portland condo with two-car parking, private outdoor space, hardwood floors, and pet-friendly living in a highly desirable location. Seller is willing to give concessions to Buyer at closing

2 Beds ⋅ 1 Baths

New price. Well-located 2-bedroom, 1-bath Portland condominium in the sought-after Deering/Rosemont area. This first-floor unit features hardwood floors, a recently renovated bathroom, private washer/dryer, private storage, a private shed, and two dedicated off-street parking spaces. A ducted heat pump system provides efficient heating and cooling with vents to multiple rooms, with boiler back-up for added comfort. Enjoy a large fenced backyard with a patio, fire pit, grill area, and plenty of space for relaxing, gardening, or entertaining. Pet-friendly association. Conveniently located near Deering High School, UNE, USM, Rosemont Market, local restaurants, Maine Medical Center, and Northern Light Mercy Hospital. Outdoor enthusiasts will appreciate nearby Evergreen Woods, offering approximately 4 miles of trails. An appealing opportunity to own a first-floor Portland condo with two-car parking, private outdoor space, hardwood floors, and pet-friendly living in a highly desirable location. Seller is willing to give concessions to Buyer at closing

280 Concord St W Unit 1, Portland

Listing courtesy of www.HomeZu.com. 877-249-5478

$799,000

Perched just steps from the ferry landing, the iconic Webber Store building is a rare offering on Peaks Island- where coastal charm, investment potential, and an elevated island lifestyle converge. Set within the island's business district, this distinctive two-story property presents a unique live/work opportunity. The first floor (Unit 1) features an inviting, flexible commercial space with three separate rooms, each with its own entrance--most recently a thriving thrift store and equally well-suited for a boutique office, creative studio, or gallery. Above, the second-floor residence (Unit 2) is a light-filled retreat, where an open-concept living space flows effortlessly onto a private deck overlooking Casco Bay and the Portland skyline. Here, sunset gatherings are framed by ever-changing ocean views. The one-bedroom layout is enhanced by a charming loft, ideal for guests or an inspiring workspace, along with a spacious closet. Both units feature private outdoor spaces and their own dedicated off-street parking spot, all just moments from the ferry, beaches, and the best of island living. A property of this caliber- rich in history, unmatched in location, and defined by its sweeping water views- offers an extraordinary chance to live, work, and unwind in one of Maine's most treasured coastal communities.

1 Beds ⋅ 2 Baths

Perched just steps from the ferry landing, the iconic Webber Store building is a rare offering on Peaks Island- where coastal charm, investment potential, and an elevated island lifestyle converge. Set within the island's business district, this distinctive two-story property presents a unique live/work opportunity. The first floor (Unit 1) features an inviting, flexible commercial space with three separate rooms, each with its own entrance--most recently a thriving thrift store and equally well-suited for a boutique office, creative studio, or gallery. Above, the second-floor residence (Unit 2) is a light-filled retreat, where an open-concept living space flows effortlessly onto a private deck overlooking Casco Bay and the Portland skyline. Here, sunset gatherings are framed by ever-changing ocean views. The one-bedroom layout is enhanced by a charming loft, ideal for guests or an inspiring workspace, along with a spacious closet. Both units feature private outdoor spaces and their own dedicated off-street parking spot, all just moments from the ferry, beaches, and the best of island living. A property of this caliber- rich in history, unmatched in location, and defined by its sweeping water views- offers an extraordinary chance to live, work, and unwind in one of Maine's most treasured coastal communities.

14 Welch St Unit 1 and 2, Portland

Listing courtesy of Peninsula Real Estate LLC.

$949,000

Positioned in Portland's desirable Parkside Neighborhood, 142 Sherman Street is a fully occupied four-unit investment property offering stable in-place income in one of the city's most sought-after residential neighborhoods. The property benefits from a walkable location just minutes from downtown, the Peninsula, and major commuter routes. The building features a functional unit mix with consistent occupancy, supported by strong rental demand in the surrounding area. The property has been well maintained and improved over time, with a series of updates to both unit interiors and key building systems, contributing to overall efficiency, condition, and long-term reliability. Tenants enjoy convenient access to local shops, restaurants, and services, supporting strong retention and continued demand.

4 Baths

Positioned in Portland's desirable Parkside Neighborhood, 142 Sherman Street is a fully occupied four-unit investment property offering stable in-place income in one of the city's most sought-after residential neighborhoods. The property benefits from a walkable location just minutes from downtown, the Peninsula, and major commuter routes. The building features a functional unit mix with consistent occupancy, supported by strong rental demand in the surrounding area. The property has been well maintained and improved over time, with a series of updates to both unit interiors and key building systems, contributing to overall efficiency, condition, and long-term reliability. Tenants enjoy convenient access to local shops, restaurants, and services, supporting strong retention and continued demand.

142 Sherman St, Portland

Listing courtesy of The Dunham Group.