Chebeague Island Real Estate

Welcome to Chebeague Island, a hidden gem nestled in the heart of Cumberland County, Maine. This idyllic island, just a stone's throw from the bustling city of Portland, offers a unique blend of natural beauty, rich history, and a tight-knit community that makes it a perfect place to call home or escape for a weekend retreat.

Chebeague Island is renowned for its stunning landscapes, featuring picturesque shorelines, lush forests, and charming cottages that dot the coastline. With over 17 miles of coastline, residents and visitors alike can enjoy an array of outdoor activities, from kayaking and sailing to hiking and birdwatching. The island's serene beaches and tranquil waters provide a perfect backdrop for relaxation and adventure alike.

Rich in history, Chebeague Island has a vibrant cultural scene that reflects its maritime heritage. The island hosts various community events throughout the year, including art shows, farmers' markets, and seasonal festivals, fostering a strong sense of belonging among residents. The local dining scene is equally inviting, with cozy eateries serving up fresh seafood and farm-to-table delights that showcase the region's culinary prowess.

Accessibility is a breeze, with regular ferry services connecting Chebeague Island to the mainland, ensuring that residents can easily enjoy the amenities of nearby Portland while retreating to their peaceful island sanctuary. Whether you are seeking a permanent residence or a seasonal getaway, Chebeague Island offers a unique lifestyle brimming with charm, community, and coastal beauty. Discover the magic of this enchanting island and embrace the tranquility that awaits you!

Newest Listings in Chebeague Island

$350,000

3 Beds ⋅ 1 Baths

A rare opportunity to own a seasonal cottage on Chebeague Island's coveted East End, just steps from the ferry, sandy beaches, and the island inn. Perfect for buyers looking to get on the island and make a place their own, the cottage is ready for some TLC while offering the chance to enjoy everything that makes island life so special. Arrive by ferry, drop your bags, and head straight to the beach. With an unbeatable location and plenty of potential, this is an opportunity to create your own Chebeague retreat. Chebeague Island amenities include beaches, trails, golf, tennis, a full-service boatyard, café and gift shop, seasonal dining, recreation center with pool, and library. Accessible by both Casco Bay Lines and Chebeague Transportation Company, as well as water taxi service from Portland.

7 Soule Rd, Chebeague Island

Listing courtesy of Portside Real Estate Group.

$1,279,000

4 Beds ⋅ 3 Baths

Waterfront Retreat located on picturesque Chebeague Island. This spacious four-bedroom, two-and-a-half-bath home embodies classic island living, offering stunning, panoramic views of Casco Bay. The interior is filled with natural light, featuring gleaming hardwood floors and three cozy wood-burning fireplaces. The property sits on three acres and includes 150 feet of exclusive waterfront, providing direct access for boating, swimming, kayaking, and fishing. The main level offers an open-concept kitchen, an inviting den with a wood-burning fireplace, and direct access to a back porch and expansive deck--perfect for enjoying breathtaking sunsets. The living and dining area features coastal shiplap, a vaulted ceiling, and a wood-burning fireplace. The lower level includes a large, dry daylight basement offering expansive and versatile storage options, and the exterior features an oversized two-car attached garage. This classic coastal hideaway is situated directly on Casco Bay, offering a private setting where you are completely surrounded by nature. The location is exceptionally convenient, situated only seven minutes from the ferry and market, and a two-minute walk or bike ride to the Community Recreation Center. The property is also close to various island amenities, including golf, tennis, sailing, scenic trails, the library, a full-service boatyard, and beautiful beaches. This property is a truly versatile option, whether you are seeking a great investment, a year-round residence, or a summer retreat.

48 Pond Rd, Chebeague Island

Listing courtesy of Portside Real Estate Group.

$198,000

Discover the rare opportunity to own 6.18 acres on beautiful Chebeague Island. This expansive property creates an exceptional setting for the creation of a dream island retreat, private estate, or a family compound. With ample space for a custom home, guest accommodations, and recreational amenities, the property provides both privacy and flexibility while remaining conveniently accessible from the island's main road. Enjoy Chebeague's peaceful woodlands, easy access to beaches, plentiful boating, fishing, hiking, and the island's close-knit community. A short ferry ride to the mainland, take advantage of Portland's restaurants, walkability, and all the city has to offer. 471 South Road offers a sprawling gateway to Maine's rugged coastline, island living, and the truly remarkable opportunity to own a significant land holding on the hidden gem of Casco Bay. Also listed separately as 14.46 acres MLS #1669576 and 8.27 acres MLS # 1669577.

471 S Road Unit B, Chebeague Island

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

$397,650

Discover the rare opportunity to own 14.46 acres on beautiful Chebeague Island. This expansive property creates an exceptional setting for the creation of a dream island retreat, private estate, or a family compound. With ample space for a custom home, guest accommodations, and recreational amenities, the property provides both privacy and flexibility while remaining conveniently accessible from the island's main road. Enjoy Chebeague's peaceful woodlands, easy access to beaches, plentiful boating, fishing, hiking, and the island's close-knit community. A short ferry ride to the mainland, take advantage of Portland's restaurants, walkability, and all the city has to offer. 471 South Road offers a sprawling gateway to Maine's rugged coastline, island living, and the truly remarkable opportunity to own a significant land holding on the hidden gem of Casco Bay. Also listed separately as 6.18 acres MLS #1669578 and 8.27 acres MLS #1669577 .

471 South Rd, Chebeague Island

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

$240,000

Discover the rare opportunity to own 8.27 acres on beautiful Chebeague Island. This expansive property creates an exceptional setting for the creation of a dream island retreat, private estate, or a family compound. With ample space for a custom home, guest accommodations, and recreational amenities, the property provides both privacy and flexibility while remaining conveniently accessible from the island's main road. Enjoy Chebeague's peaceful woodlands, easy access to beaches, plentiful boating, fishing, hiking, and the island's close-knit community. A short ferry ride to the mainland, take advantage of Portland's restaurants, walkability, and all the city has to offer. 471 South Road offers a sprawling gateway to Maine's rugged coastline, island living, and the truly remarkable opportunity to own a significant land holding on the hidden gem of Casco Bay. Also listed separately as 6.18 acres MLS #1669578 and 14.46 acres MLS # 1669576.

471 S Rod Unit A, Chebeague Island

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

$796,000

3 Beds ⋅ 2 Baths

This beautifully renovated historic meeting house, originally built in the 1830s, seamlessly blends timeless New England charm with thoughtfully integrated modern conveniences. The transformation from an antique meeting house into a stunning private residence was completed in 2011. The home preserves its rich history while offering the comfort and functionality of contemporary living. The island's only brick building, the meeting house was constructed using bricks made on the island, making it a truly unique piece of local history. The well-appointed kitchen features granite countertops, modern appliances, and a spacious refrigerator, making it ideal for both everyday living and entertaining. The home offers three bedrooms and two full bathrooms, along with a game room complete with a billiards table for recreation and relaxation. At the heart of the home is a newly rebuilt Rumford fireplace, designed to maximize heat output while creating a warm and inviting gathering space. The living room showcases vaulted ceilings with the original exposed beams from the historic meeting house, adding remarkable architectural character. A bright three-season sunroom opens onto a charming brick patio enclosed by a classic stone wall. The spacious, beautifully maintained yard also includes a potting and tool shed, providing additional storage and workspace for gardening enthusiasts. Enjoy year-round peace of mind with a whole-house, on-demand generator. Experience the best of island living with exceptional community amenities, including a daycare, elementary school, library, museum, assisted living facility, boatyard, golf course, and tennis courts. Explore the islands beaches and surrounding Casco Bay. This extraordinary property offers a rare opportunity to own a beautifully restored historic landmark while embracing the relaxed lifestyle of island living.

10 Meeting House Ln, Chebeague Island

Listing courtesy of EXP Realty.

$1,695,000

4 Beds ⋅ 5 Baths

A rare opportunity to own a spectacular waterfront property on highly sought-after Chebeague Island. Privately situated with a coveted westerly orientation, this exceptional location offers breathtaking sunsets, deep-water access, and an extraordinary island lifestyle just a short distance from Portland. The property features a substantial deep-water dock, private beach frontage, dramatic ledge outcroppings, and picturesque tidal pools that create an unforgettable coastal setting. An antique Cape, expanded and modified over the years, may be enjoyed in its current form, thoughtfully renovated, or more fully reimagined to suit your vision and make the most of the property's exceptional setting. The expansive grounds offer further potential for a legacy compound or multigenerational retreat. Combining privacy, natural beauty, and convenient proximity to the mainland, this is a truly unique offering where boating, swimming, gathering, and relaxed coastal living come together in one remarkable destination. Chebeague Island offers a unique blend of coastal charm and everyday convenience, making it one of Maine's most desirable island communities. Residents and visitors enjoy amenities such as a scenic nine-hole golf course, tennis courts, beautiful public shoreline access, and a full-service marina and boatyard. The island also features a year-round library, recreation center, community school, café dining, and the historic Chebeague Island Inn overlooking Casco Bay. Grocery delivery service adds an extra level of convenience for year-round and seasonal residents alike. Accessible by ferry from Yarmouth or Portland, Chebeague provides a peaceful island lifestyle while still remaining connected to the mainland. Outdoor recreation, boating, biking, walking trails, and strong community traditions make the island especially appealing for both seasonal and year-round living.

61 Sawyer Rd, Chebeague Island

Listing courtesy of Town & Shore Real Estate.

$169,000

Buxhill Boulevard, Lot 2 consists of 1.35 acres in a convenient location near the Stone Pier, CTC Ferry, Chebeague Island Inn, Great Chebeague Golf Club with its nine-hole golf course, and several beaches, including Hamilton Beach. Explore the possibility of building your own two-bedroom island cottage with glimpses of water views on one of Casco Bay's most desirable islands. The parcel has been surveyed and includes a two-bedroom septic design.

Lot 2 Buxhill, Chebeague Island

Listing courtesy of Legacy Properties Sotheby's International Realty.

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