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6 Harbor Ledge Ln, Southport
$3,650,000
3 Beds ⋅ 3 Baths ⋅ 1662169 MLS
Perched high above Southport Island's east shore with panoramic views of the Townsend Gut, Boothbay Harbor, and outer islands, this extraordinary 3,300+/- sq ft. Scandinavian-inspired retreat delivers a seamless blend of modern luxury and Maine's scenic beauty. Water views are ever-present, welcomed into living spaces by 9' windows & doors for truly breathtaking vantages. Designed to encourage gatherings, the home features open concept living, with a great room that includes 10' ceilings and a wood-burning fireplace, a woodsy screened porch above the waterfront, and a large waterfront lawn with 6' x 6' granite slab fire pit. Built for year-round use, the property includes advanced systems such as closed-cell insulation, Mitsubishi heating & cooling, public water supply, and a 42kW, whole-house generator. Set on 1.2-acres with 350' of deep-water ocean frontage, the property ensures an unparalleled waterfront lifestyle, with a private pier & oversized float, a multitude of outdoor living spaces, cooling sea breezes, and quick access to area amenities, by car or by boat.

6 Harbor Ledge Ln, Southport

Listing courtesy of Tindal & Callahan Real Estate.

Selling Office: Tindal & Callahan Real Estate.

75 Stowaway Rd, Southport
$2,950,000
3 Beds ⋅ 4 Baths ⋅ 1673667 MLS
Experience coastal Maine living at its best in this custom-built shingle-style home, set on 2.25 landscaped acres with 501' +/- of deep-water frontage and a protected private dock and sandy beach. Featuring sweeping southwesterly views to Sequin Island, this property perfectly balances luxury and comfort. The open-concept main floor centers on a chef's kitchen, a formal dining room, and a dramatic two-story living room with a propane fireplace. A sun-drenched, vaulted-ceiling sunroom, convenient mudroom, and a luxurious first-floor primary suite complete the main level. The second floor offers two ensuite guest bedrooms and a versatile family room. Designed with precision, the home includes radiant propane floor heat, a daylight walkout basement, an oversized heated two-car garage, and a whole-house generator. Being sold completely furnished. A rare find on the Maine coast.

75 Stowaway Rd, Southport

Listing courtesy of Tindal & Callahan Real Estate.

Selling Office: Armentrout Select Realty of Maine.

30 Cedar Bush Ln, Southport
$1,500,000
4 Beds ⋅ 2 Baths ⋅ 1665595 MLS
Quintessential Maine coastal cabin offering 4 bedrooms and 2 baths in a private setting with beautiful ocean views and refreshing sea breezes. This seasonal retreat has been thoughtfully updated while preserving its classic coastal charm. Recent improvements include a new septic system, new roof, repair of all wood rot, and more, providing peace of mind for future ownership. Interior updates include fresh paint and high end furnishings throughout, along with new mattresses and top of the line LL Bean bedding. Enjoy outdoor living from the covered deck, shoreline seating area, and multiple outdoor gathering spaces. Located just a short walk from Hendrick's Head Beach, the Southport General Store, and Hendrick's Head Preserve, with Boothbay Harbor restaurants, shops, and attractions only minutes away. A rare opportunity to own an authentic Maine summer getaway that combines timeless character, quality finishes, and significant recent improvements. Book your showing today. Private Road. Please No Drive By's

30 Cedar Bush Ln, Southport

Listing courtesy of The Real Estate Store.

Selling Office: Tindal & Callahan Real Estate.

26 Pratts Island Rd, Southport
$1,495,000
3 Beds ⋅ 3 Baths ⋅ 1672367 MLS
Located in one of the Boothbay Region's most scenic coastal neighborhoods, this property presents a special opportunity to join the coveted Cozy Harbor community. All attention is focused toward the water, where boating activity of all types is on full display, as are stunning sunsets. The houses were built with this in mind, with abundant windows toward the water and perhaps its most satisfying element, an 11'8'' x 15'5'' screened porch overlooking the harbor and Sheepscot River, beyond. The property has been thoughtfully developed with a main house, guest house, and studio building, beautifully accented by rock walls and gardens. Built in 2018 by Becker Construction, the construction is high-quality and features modern fundamentals, including propane-fired heat, heat pumps for cooling, water filtration, and an automatic generator. The property will convey with a one third interest in a waterfront parcel across the street, which includes a deepwater dock, boathouse, and wharf. This is a must-see for those seeking a seasonal or year-round property in a quintessential Maine setting.

26 Pratts Island Rd, Southport

Listing courtesy of Tindal & Callahan Real Estate.

Selling Office: Tindal & Callahan Real Estate.

236 Dogfish Head Rd, Southport
$1,100,000
4 Beds ⋅ 2 Baths ⋅ 1669943 MLS
The perfect summer cottage on Dogfish Head with waterfront on the Sheepscot River. Enjoy the sunsets, boating activity all day long from this immaculately maintained cottage. The first floor offers a living room with fireplace, dining room, kitchen and bath, complemented by a screened porch and an open deck. The 2nd floor offers 3 bedrooms, a half bath and access to a 2nd floor deck. The third floor is a spacious gathering area, offering breathtaking views, perfect office space or read your favorite book. Built-in benches with storage. There is a ladder that takes you to a widow's walk from this room. Additional amenities include a guest cabin, access to a shared dock, and close proximity to the local beach and general store.

236 Dogfish Head Rd, Southport

Listing courtesy of Tindal & Callahan Real Estate.

Selling Office: Tindal & Callahan Real Estate.

30 & 34 Nickerson Rd, Southport
$925,000
3 Beds ⋅ 3 Baths ⋅ 1680109 MLS
Located on desirable Southport Island, this three bedroom, three bath year round home is filled with natural light and has stunning views of all the boating traffic on Townsend Gut. Many improvements have been made within the last five years, including a totally renovated kitchen with new granite countertops and stainless appliances; new windows, sliding glass doors, and solar-powered remote skylights; a whole-house automatic generator; three renovated bathrooms and much more! A separate one-bedroom, 1 bath guest cottage, which comes completely furnished, has a great rental history. Located on a dead-end street, there is also a 10 walking ROW to water. Beautiful Boothbay Harbor and all of its amenities are less than 10 minutes away.

30 & 34 Nickerson Rd, Southport

Listing courtesy of Tindal & Callahan Real Estate.

Selling Office: Tindal & Callahan Real Estate.

58 Hendricks Hill Rd, Southport
$665,000
4 Beds ⋅ 3 Baths ⋅ 1650412 MLS
Located on charming and highly desirable Southport Island, this turn-key property offers a thoughtful blend of comfort, functionality, and recent upgrades in a convenient coastal setting. The four-bedroom, three-bath residence provides the option for first-floor living and features a Vermont Castings woodburning stove, granite-appointed kitchen, newer appliances, covered porch, and an open deck, ideal for both everyday living and entertaining. Notable improvements include connection to town water, a four-bedroom-designed septic system, new first floor full bathroom, rug, vinyl floors, 2021 shingled garage and house, garage doors, automatic whole-house standby generator, paved driveway, and beautifully maintained gardens and hardscape to name a few. Lots of new features and personal updates to list in this home inside and out that a new owner would not need to invest in. A standout feature is the 24' x 30' two-story barn, constructed in 2021 and connected to the home by a breezeway, complete with an adjacent paddock. This versatile space offers excellent potential for animal use, hobby farming, workshop conversion, or simply added convenience and storage. The property also boasts a large two and a half bay garage with space above to customize or use for storage. Southport Island is known for its welcoming community and coastal charm, offering local restaurants, shops, public beaches, and docks. Ideally located just moments from the Townsend Gut Swing Bridge, the property provides effortless access to Boothbay Harbor's renowned shops, dining, and waterfront, an exceptional opportunity to enjoy island living with proximity to premier Midcoast Maine amenities.

58 Hendricks Hill Rd, Southport

Listing courtesy of Legacy Properties Sotheby's International Realty.

Selling Office: Vitalius Real Estate Group.

23 Nickerson Rd, Southport
$570,000
2 Beds ⋅ 1 Baths ⋅ 1684256 MLS
Embrace the classic coastal Maine lifestyle in this charming 2-bedroom, 1-bathroom Southport Island cottage. Tucked away on a quiet road just over the bridge, this beautifully maintained home offers the perfect balance of peaceful privacy and easy convenience to all the amenities of downtown Boothbay Harbor. Step inside to find a neat and tidy layout throughout, designed for easy living. The highlight of the home is a spacious family room addition, boasting dramatic vaulted ceilings and a cozy fireplace that serves as the perfect centerpiece for crisp autumn evenings or summer gatherings. Outside, the back deck seamlessly extends your living space into a beautifully landscaped yard, providing an ideal setting for outdoor dining, gardening, or simply relaxing. Take in the serene surroundings and enjoy lovely peekaboo views of the Townsend Gut right from the house and property. Whether you are looking for a classic summer getaway or a low-maintenance year-round home, this island gem offers a wonderful opportunity to join the vibrant Southport community.

23 Nickerson Rd, Southport

Listing courtesy of Tindal & Callahan Real Estate.

Selling Office: Tindal & Callahan Real Estate.

11 Youngs Rd, Southport
$461,500
3 Beds ⋅ 3 Baths ⋅ 1629793 MLS
Tucked away on a scenic knoll surrounded by spruce trees and natural landscaping, this Southport Island retreat offers the perfect escape—whether for summer getaways or year-round living. Spread across three levels, the home provides ample space for family and guests, with a primary suite, 2-3 additional bedrooms, and 2.5 baths. The heart of the home is the spacious great room, where the kitchen, dining, and living areas flow together beneath soaring ceilings—anchored by a striking central fireplace, ideal for cozy evenings and memorable gatherings. Step out onto generous decks on both the first and second levels, or unwind in the secluded hot tub tucked just off the lower deck. Dreaming of island life? Now's your chance. Connected to the Boothbay mainland by a historic swing bridge, this charming village offers a unique blend of serenity and community spirit. Enjoy local inns and restaurants, a quaint general store, a peaceful beach, and all the coastal charm Maine is known for.

11 Youngs Rd, Southport

Listing courtesy of Newcastle Realty. 207-633-4433

Selling Office: Camden Real Estate Company.

527 Cape Newagen Rd, Southport
$425,000
2 Beds ⋅ 1 Baths ⋅ 1658090 MLS
Are you tired of renting? This seasonal cottage on Southport Island offers a wonderful opportunity to own a two-plus bedroom home on a private 4.7-acre wooded parcel. The cottage features a poured concrete foundation and an open floor plan encompassing the kitchen, dining, and living areas--complete with a propane wood stove for chilly nights. The layout includes a first-floor bedroom and a second-floor bedroom with an open loft that can serve as a game room, studio, or guest space, featuring its own private balcony. Outdoor living is easy with both a screened porch and an open deck. You can enjoy the peace of this wooded site while staying close to local favorites like Hendrick's Head Beach, Southport General Store, and Robinson's Wharf as well as a short drive to golf, hiking trails, botanical gardens, and all the Boothbay Region has to offer.

527 Cape Newagen Rd, Southport

Listing courtesy of Tindal & Callahan Real Estate.

Selling Office: Legacy Properties Sotheby's International Realty.

391 Cape Newagen Rd, Southport
$416,000
2 Beds ⋅ 1 Baths ⋅ 1646459 MLS
Welcome to this charming open concept cottage on the tranquil island of Southport. Newly constructed in 2023, this inviting home blends modern comfort with serene coastal living. The main floor consists of a nicely appointed kitchen, a cozy living room, a comfortable bedroom and a large bath with laundry area. Expansive windows fill the space with natural light and afford peaceful views of the surrounding woods. A versatile loft overlooks the main living area and can be set up as a second bedroom or other living area. A separate smaller room could be a home office or a relaxing reading area. Set on a soon to be surveyed 1.5 acre lot; that will provide ample privacy and room to enjoy the peaceful quiet of the island. Whether you're seeking a seasonal getaway or a year round home, this thoughtfully designed cottage has the perfect blend of simplicity, comfort and modern style.

391 Cape Newagen Rd, Southport

Listing courtesy of Harbor Realty.

Selling Office: The Maine Real Estate Experience.

14 Pinkie Ln, Southport
$175,000
2 Beds ⋅ 2 Baths ⋅ 1635079 MLS
This little Pinkie Went to Market Rare Southport Find - Funky Fixer with Loads of Potential! ✨ Looking for a home you can make your own? Welcome to 14 Pinkie Lane, tucked away at the very end of a quiet dead-end road in beautiful Southport. This is a rare opportunity to snag a reasonably priced home in a prime location, with plenty of room for creativity and updates. Inside, you'll find a fun and funky floorplan with 2 bedrooms and 2 bathrooms, a great start for anyone who loves character and quirk. Step outside onto the huge deck—perfect for grilling, entertaining, or just soaking in the peaceful surroundings. There's even a balcony for morning coffee and a yard that feels like your own private retreat, complete with a frog pond, lush plantings, and plenty of natural charm. Need space for projects, storage, or hobbies? You'll love the large workshop/garage area, plus an additional one-car garage. This is more than just a house—it's a canvas ready for your vision. With its private setting, unique personality, and tons of potential, 14 Pinkie Lane is a Southport gem just waiting for someone to bring it back to life. 🔑 Bring your ideas, roll up your sleeves, and create your dream coastal escape!

14 Pinkie Ln, Southport

Listing courtesy of Realty of Maine.

Selling Office: Vitalius Real Estate Group, LLC.

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