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26 Lanewood Rd, Cumberland
$5,195,000
3 Beds ⋅ 5 Baths
More than 380 feet of frontage on Broad Cove and nearly five private acres create an extraordinary waterfront setting in the heart of Cumberland Foreside. Beyond a winding drive, the property reveals itself gradually, where mature trees frame the shoreline and the home settles naturally into the landscape. The experience here is defined by privacy, the quiet rhythm of the tides, and ever-changing water views from nearly every principal room. The property's size and configuration also present the potential to create a separate home site with water access. Designed to celebrate the landscape, the home unfolds through a series of beautifully proportioned spaces, each taking full advantage of the surrounding water and gardens. A dramatic two-story foyer, gracious living spaces, a vaulted sunroom wrapped in glass, and a beautifully appointed primary suite are all oriented toward the water, while rich millwork, warm hardwood floors, and carefully curated details create interiors that feel enduring and quietly refined. Bluestone terraces extend naturally toward the shoreline, inviting long summer evenings, effortless entertaining, or peaceful mornings overlooking the cove. Just minutes from Cumberland Center, Falmouth, Portland, yacht clubs, golf, and some of Maine's most treasured coastal destinations, this is a home of quiet beauty, where the landscape has always been the centerpiece.

26 Lanewood Rd, Cumberland

Listing courtesy of RE/MAX By The Bay.

10 Fairwind Lane Ext, Cumberland
$3,150,000
4 Beds ⋅ 3 Baths
Set proudly at the highest elevation in Southern Maine, with far-reaching views of Casco Bay and the Calendar Islands, this brick Tudor estate possesses an architectural pedigree evocative of a distinguished English manor. Masterfully conceived and meticulously built by renowned commercial builder C.M. Cimino as his personal residence, the home reflects permanence and sophisticated European character. Accessed via a long, winding private drive, the gracious 2.93-acre property features mature trees and gardens, stone walls, and a sweeping lawn overlooking the bay. A dramatic two-story foyer and curving staircase introduce interiors as refined as they are inviting. Freshly painted and warmed by polished hardwood floors, three fireplaces, and breathtaking vistas, the expansive, light-filled rooms retain an intimacy that belies their scale. From festive holiday gatherings in the stately dining room to white-tent soirées on the lawn, the thoughtfully conceived layout accommodates grand occasions with ease, while its intimate gathering spaces lend themselves equally to relaxed evenings and the quiet pleasures of daily life. A beautifully appointed new primary suite with a spa-like bath and a newly completed guest suite provide private sanctuaries, while a custom-built African cedar sauna for four offers a restorative retreat. Completed architectural plans are available for additional living space above the garage, with options for a fifth bedroom, office, in-law suite, or media room. Additional amenities include a new roof with copper ridge caps, two new Viessmann Vitocrossal boilers, and a commercial-grade whole-house generator. Ideally located in the heart of Cumberland Foreside, just minutes from the town beach, restaurants, and award-winning schools, this remarkable estate brings together scale, provenance, privacy, and commanding coastal views. An uncommon offering of enduring character, exceptional craftsmanship, and unmistakable distinction.

10 Fairwind Lane Ext, Cumberland

Listing courtesy of Legacy Properties Sotheby's International Realty.

Lot 9 Coastal Pines, Cumberland
$2,542,287
5 Beds ⋅ 6 Baths
Privately positioned at the end of a cul-de-sac in one of Cumberland's most sought-after neighborhoods, this exceptional new construction home by Brush & Hammer Builders showcases Coastal Contemporary design and high-end finishes. Blending classic New England architecture with clean, modern styling and systems, this custom residence offers exceptional craftsmanship and a floor plan tailored to today's lifestyle. The heart of the home is a vaulted great room that flows seamlessly into a beautifully appointed kitchen featuring an oversized island, walk-in pantry, and generous dining area. On the main level, the primary suite features a gas fireplace, an expansive bath, and a custom walk-in closet. A dedicated office, generous mudroom, and four-car garage complete a layout that offers both everyday convenience and long-term flexibility. Upstairs, three en-suite bedrooms provide comfort and privacy for family and guests. The walkout lower level expands the living space with a family room, game room, kitchenette, full bath, and guest bedroom, creating an ideal setting for entertaining or extended stays. Covered outdoor living areas, abundant natural light, and carefully considered architectural details complete a home that balances everyday comfort with a refined, timeless aesthetic.

Lot 9 Coastal Pines, Cumberland

Listing courtesy of RE/MAX By The Bay.

17 Coastal Pnes, Cumberland
$2,390,000
4 Beds ⋅ 5 Baths
Perfectly positioned at the end of a quiet cul-de-sac in the desirable Coastal Pines Subdivision, this exceptional residence was built with an uncompromising commitment to quality, craftsmanship, and timeless elegance. Offering more than 5,000 square feet of thoughtfully designed living space, the home seamlessly blends luxury, functionality, and effortless comfort. As you enter, the home immediately impresses with an abundance of natural light, 9-foot ceilings, and meticulous attention to detail evident throughout every finish and fixture. The custom-designed kitchen is a true focal point, featuring premium finishes, a spacious eat-in area, and a large walk-in pantry. A separate dining area provides an ideal setting for entertaining, while the breathtaking living room serves as a stunning gathering space, highlighted by its dramatic vaulted ceiling, striking fireplace, and impressive wall of glass overlooking the private yard. The 1st floor primary suite offers a luxurious retreat, complete with a spa-inspired bathroom featuring dual vanities, a soaking tub, custom-tiled shower, and an expansive walk-in closet with custom-built cabinetry. An office, convenient laundry room, and additional thoughtfully designed living spaces complete the main level. Upstairs, a beautiful loft overlooks the great room below and takes full advantage of the home's impressive windows and surrounding views. The second level also features an en-suite bedroom, two additional bedrooms, and a full bathroom, providing exceptional accommodations for family and guests. The full daylight basement extends the living space even further, featuring a spacious bonus room with a custom bar, wine cabinet, and fireplace; a full bathroom; dedicated space for a home gym; an office or den; and generous storage and utility areas. Built with exceptional craftsmanship and quality finishes throughout, this remarkable home is truly a property to experience. Welcome to 17 Coastal Pines!*Photo renderings used*

17 Coastal Pnes, Cumberland

Listing courtesy of Portside Real Estate Group.

186 Foreside Rd, Cumberland
$1,475,000
5 Beds ⋅ 4 Baths
This beautifully preserved New Englander home blends classic architecture with thoughtful updates in one of Greater Portland's most sought-after locations. A welcoming front hall showcases the home's original character with an elegant staircase and period millwork, inviting you inside to explore the expansive and flexible layout. The formal living room is anchored by a gas fireplace, while the comfortable family room overlooking the rear yard features a cozy heat stove. The updated kitchen includes a walk-in pantry and adjacent dining area. A full bath and additional room currently used as a bedroom complete the first floor. All of this flows seamlessly to an expansive tiered deck with hot tub, overlooking the private backyard and pool area. A spacious bonus room with half bath reached by its own staircase from the family room functions as a home office, playroom, guest space or future primary ensuite with conversion of the existing half bath to a full bath. Follow the original staircase from the front hall to the second and third floors, with each level offering a full bath and multiple bedrooms. Outside, the pool area calls for relaxation. The pool house is a legal ADU with kitchenette, sitting area, half-bath and laundry opening onto the pool deck, plus a bedroom and full bath upstairs, offering 864 sf of additional living space. Whether used for guests, entertaining, or rental income, it offers endless possibilities. Many improvements--heat pumps, whole-house automatic generator, solar panels, irrigation system, and more--enhance comfort, efficiency, and peace of mind. Life in Cumberland offers the best of coastal Maine, with award-winning schools, a welcoming community, and abundant outdoor recreation. Nearby Broad Cove Reserve offers 23 acres of protected shoreline with sandy beach, pier, and walking trails just steps from your door. Enjoy the beauty of the Foreside with Portland's acclaimed restaurants, shopping, and arts scene just a short drive away.

186 Foreside Rd, Cumberland

Listing courtesy of Portside Real Estate Group.

6 Nautical Dr, Cumberland
$849,900
4 Beds ⋅ 3 Baths
You'll believe in love at first sight when you step into this gorgeous Cumberland Foreside colonial! Sitting pretty on a spacious lot in a welcoming & walkable neighborhood, this 4-bedroom, 3-bath beauty is the perfect backdrop for life's most treasured moments. Hardwood floors, lofty ceilings, large rooms, and a flowing floor plan await inside. The kitchen's granite countertops, tile backsplash, stainless steel appliances, gas stove, and pantry will make every home chef happy. Enjoy breakfast seated at the island; linger over dinner in the dining area. The seamlessly situated living room is a great place to gather. A half bath rounds out the main floor. Upstairs, the dreamy primary suite provides ample space to stretch out, a walk-in closet, and a recently revamped bathroom with a walk-in shower. Three additional bedrooms/multi-use rooms, a full bathroom, and a laundry room provide plenty of options on the second floor. Need more space to store your stuff? The daylight walkout basement (which could be finished for a future family room) and attached garage are ready to serve. Outside, the freshly renovated front porch and back deck are sweet spots for morning coffee and al fresco fare. The big backyard means there's plenty of room to play; the custom fire pit is ready for s'mores under the stars. Idyllic and adored, Cumberland's rolling hills, hiking trails, and easy local water access make life great. Any amenity you need is a short dash away, and Yarmouth, Freeport, and Portland's spoils are within easy reach. A perfectly appointed home in an enviable locale - the epitome of small-town charm with effortless convenience. The best of all worlds is at your doorstep with this easy living home!

6 Nautical Dr, Cumberland

Listing courtesy of King + Miller Real Estate. info@kingmillerrealestate.com

13 Nautical Dr, Cumberland
$799,900
3 Beds ⋅ 3 Baths
Craving a stunning home in a coveted Cumberland Foreside community? This 3-bedroom, 3-bath beauty delivers! Nestled in a welcoming, walkable neighborhood in easy reach of everyday essentials, this property will have your heart. Mood-boosting natural light, an open layout, hardwood floors, and thoughtful design details are a delight inside. You'll love making memorable meals in the kitchen, thanks to granite countertops, stainless steel appliances, a gas stove, a new refrigerator & dishwasher, and an island with storage & seating. The seamlessly situated dining area makes gathering a breeze. The living room is a perfect place to relax with your favorite people & pets. A half bath rounds out the main floor. The primary suite upstairs is your go-to for relaxation, complete with a walk-in closet and full bathroom. Two additional second-floor bedrooms/multi-use rooms, a family/play room, a full bathroom, and a laundry closet mean there's plenty of room for all. Below deck, the finished basement provides opportunities galore for your home office, home gym, and more. Take your pick from the backyard patio or front porch for soaking up the sun through the seasons. A new boiler, automatic whole-house generator, and built-in irrigation system mean never worrying about chilly rooms, power outages, or parched landscaping. The attached 2-car garage is ready for your cars, toys, and tools. Abundant amenities are yours for the taking from this special spot, from gas to groceries to dining & entertainment. You need not leave the bounds of town for a thing, but when you do, the highway is within easy reach. You'll love coming home to this Cumberland gem!

13 Nautical Dr, Cumberland

Listing courtesy of King + Miller Real Estate. info@kingmillerrealestate.com

44 Glacier Dr Unit 47, Cumberland
$750,900
3 Beds ⋅ 3 Baths
An individually designed home in Phase II of Mineral Springs, featuring a floor plan that balances open gathering spaces with private retreats. The main level brings together the kitchen, dining, and living areas, while upstairs offers three bedrooms, a bonus room, and generous storage. A full basement and attached two-car garage provide flexibility for everything from outdoor gear to future expansion. Mineral Springs was planned with the landscape in mind. Walking trails, shared green spaces, a neighborhood sports court, and a playground create a setting where outdoor recreation is part of daily life. Set in West Cumberland, it's a community that feels connected to both nature and its neighbors.

44 Glacier Dr Unit 47, Cumberland

Listing courtesy of Portside Real Estate Group.

40 Powell Rd, Cumberland
$725,000
3 Beds ⋅ 3 Baths
Set on 1.53 beautifully established acres in coveted Cumberland Foreside, 40 Powell Rd reflects decades of thoughtful care. With just two owners throughout its history, this 3 bed, 2.5 bath home has been lovingly and meticulously maintained and is ready for its new owner. Inside, the 1st floor offers a comfortable, flexible layout with a remodeled kitchen, mudroom, half bath, formal dining room, living room with fireplace, and bonus room leading to the expansive back deck. Upstairs are 3 bedrooms, including 2 with a shared hallway bath and a spacious primary suite with an impressive walk-in closet and private full bath. Heat pumps, a whole-house generator, and attached 2 car garage add comfort and convenience year-round. Outside is where decades of care really come into view. The front and back yards have been continuously landscaped since the 1990s, creating an established property filled with mature plantings that change throughout the seasons. Hydrangeas, peonies, hostas, blueberries, several varieties of iris and daisies, and many more perennials fill the grounds, while Joe-Pye weed and liatris bring butterflies to the gardens. A hand-laid front walkway welcomes you home, while a peaceful waterfall pond adds another special element. And then there is the location. Cumberland Foreside is one of southern Maine's most coveted coastal communities. Just .5 miles away is deeded waterfront access to the ocean, making it easy to enjoy one of the very things that makes living in the Foreside so special. Cumberland Center, Yarmouth, Falmouth and Portland are all close by. There is something special about a property that has been in the hands of only two owners and cared for this intentionally. 40 Powell Road offers the opportunity to settle into an established property in one of Maine's most desirable coastal communities. To view a full video walk thru tour, head to YouTube & search the property address.

40 Powell Rd, Cumberland

Listing courtesy of U&R Real Estate.

10 Ole Musket Rd Unit 4, Cumberland
$725,000
2 Beds ⋅ 2 Baths
You will fall in love with Stony Manor. Situated in desirable Cumberland Foreside and tucked into one of the prettiest seaside neighborhoods one could imagine this condominium is unlike anything else you will find in greater Portland. This former estate offers condo living with water views and deeded rights to the water! It holds the original charm and qualities of the Manor House, yet offers modern 21st century living. Beautiful landscaping, a live-in caretaker, & full maintenance ensure a leisurely lifestyle. This 2-bedroom, 2-bath unit features a floor-plan that flows from the living room with a gas fireplace into the spacious eat-in kitchen. The master en-suite includes a beautifully updated bath, water views, and access to a deck overlooking the yard and gardens below. The second bedroom suite is generous in size and charm. With a detached two-car garage that has finished space perfect as an office or guest quarters, a swimming pool, billiards room and fitness center on the lower level, this condo offers something for everyone.

10 Ole Musket Rd Unit 4, Cumberland

Listing courtesy of Portside Real Estate Group.

261 Main St, Cumberland
$700,000
4 Beds ⋅ 2 Baths
Welcome home to 261 Main Street, perfectly sited in the heart of Cumberland Center with picturesque, walkable access to all village amenities. Blending classic Cape Cod charm with modern sophistication, this thoughtfully expanded home is designed for seamless daily living and effortless entertaining.At the center of the home, a granite-accented kitchen flows into a light-filled family room addition that opens directly to the new deck and private backyard—creating an ideal indoor-outdoor flow for summer gatherings. The main level offers exceptional versatility with a formal dining room, a first-floor bedroom, and a dedicated home office, making it easy to adapt for remote work, a home gym, or main-level living. Upstairs, enjoy a spacious primary suite alongside two additional generous bedrooms and a spa-inspired full bath. Numerous updates, rest easy with an on-demand generator as well! Modern comforts, timeless character, and an unbeatable location—welcome to your ideal Cumberland retreat.

261 Main St, Cumberland

Listing courtesy of Legacy Properties Sotheby's International Realty.

45 Sand Point Ln Unit 45, Cumberland
$689,000
2 Beds ⋅ 2 Baths
In Rockwood, simple enjoyments take center stage, with mornings on the deck, evenings by the fire, casual strolls along the neighborhood sidewalks, and everything you need within easy reach on a single level. This 2-bedroom, 2-bath condo in Cumberland's established 55+ community, provides easy, low maintenance living amid well tended landscaping. Making your way inside, you'll find hardwood floors leading you through an open living space crowned by cathedral ceilings, lending every room a light, airy feel. The kitchen is well equipped, with ample cabinetry, stainless steel appliances, and granite countertops offering plenty of room to cook, gather, and linger. The living room draws you in around a gas fireplace framed by a clean, classic mantel, while just beyond through the family room, a private deck invites quiet moments, coffee at sunrise, or simply unwinding as the day settles down. The primary suite is complete with a private full bath, double vanity, and a walk-in closet. Add in first-floor laundry, direct entry from the 2-car garage, central air, a whole-house generator for year-round peace of mind, and a full unfinished walk-out basement ready for storage or future expansion, and everyday living becomes remarkably simple. With the effortless ease of Rockwood community living, this home is built for comfort without the upkeep, it's a wonderful opportunity to find your new home in one of Cumberland's most cherished neighborhoods.

45 Sand Point Ln Unit 45, Cumberland

Listing courtesy of RE/MAX By The Bay.

22 Pinewood Dr, Cumberland
$679,000
4 Beds ⋅ 3 Baths
In the heart of Cumberland Center, 22 Pinewood Drive delivers that hard-to-find combination of location, curb appeal, privacy, and everyday convenience. Set on a wonderfully tree-lined street with an abundance of streets to meander, the home is close to the center of town, local schools, and just a stone's throw from Val Halla Golf & Recreation. The exterior has received a serious refresh with a new roof, a totally redone retaining wall, granite steps, and new front gutter system, giving the home a fresh, polished look from the street. Inside, the main floor features new flooring, while the lower-level laundry room and mudroom/drop zone have been thoughtfully redone for everyday function and yard access. A newly installed natural-gas furnace and heat pump provide efficient heating and cooling, while the patio offers a great spot to enjoy the private, level lot. The one-car garage is currently outfitted with an electric heater and used as a gym, offering flexibility for fitness, storage, or traditional garage use. There's so much to love about this beautifully refreshed Cumberland Center home, perfectly positioned in a prime location with thoughtful updates, a private setting, and plenty of curb appeal.

22 Pinewood Dr, Cumberland

Listing courtesy of Waypoint Brokers Collective. monica@waypointbrokers.com

1 Buds Trl, Cumberland
$549,000
3 Beds ⋅ 2 Baths
Set in an established neighborhood, this open concept colonial home offers a bright, open first floor with comfortable living and dining spaces, a kitchen with peninsula seating, and a back deck made for easy entertaining. Lovingly maintained and thoughtfully updated, the home features a 2023 roof, newer appliances, hardwood flooring in place of carpeting, refreshed outdoor spaces, and a shed. Propane heat! Laundry in the walkout basement with ample storage and a seasonal home gym add everyday function. Plus a portable generator hookup add peace of mind, though the sellers have never needed to use it. Just minutes from Cumberland's schools, shops, restaurants, trails, and I-95.

1 Buds Trl, Cumberland

Listing courtesy of Waypoint Brokers Collective. monica@waypointbrokers.com

20 Solar Way, Cumberland
$297,000
MORE THAN LAND. A PLACE TO CREATE YOUR HOME. Exclusive Builder Opportunity with The Nesting Ground Discover a rare opportunity to create a truly personal custom home in Cumberland, Maine. Tucked away on a private dead-end road, this exceptional 1.4-acre parcel offers a level of privacy and connection to nature that is increasingly hard to find. And this opportunity goes beyond the property itself. The buyer will have the opportunity to partner with The Nesting Ground, an experienced Maine design/build team specializing in thoughtfully designed, energy-efficient homes that are carefully integrated with their natural surroundings. The property also provides access to more than 10 additional private acres and an established trail system, offering an extraordinary extension of your own backyard. Whether it's a morning walk through the woods, snowshoeing the trail network in winter, or simply enjoying the peace and privacy of the setting, this is a property designed for those who value a connection to nature. With The Nesting Ground's collaborative approach, the vision for your home can begin with the land itself—considering the setting, sunlight, views, natural features, indoor-outdoor connection, and the way you want to live. Rather than choosing from an existing home, this is an opportunity to create something that is uniquely yours from the ground up. Led by Patrice Cappelletti, The Nesting Ground brings more than two decades of experience in design, development, and building to the process, with a focus on creating homes that are beautiful, efficient, durable, and responsive to their surroundings. This is more than a building lot. It's the opportunity to create a one-of-a-kind home on a private way, and a lifestyle designed around you. Located in highly desirable Cumberland, this private setting is conveniently located to local amenities, shopping, and restaurants in Yarmouth and the Greater Portland area.

20 Solar Way, Cumberland

Listing courtesy of Home At Last Realty.

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