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$299,900
2 Beds ⋅ 1 Baths ⋅ 1679589 MLS
This adorable home welcomes you to enjoy the preservation of historic charm with move in ready, updated conveniences. Major systems have all recently been updated, allowing affordable and efficient living. The main living level features a covered porch entry, comfortable flow from living to dining, spacious kitchen, and private screened three season porch to enjoy your morning coffee. The second level features 2 bedrooms and a full bath. Bring you pup along to enjoy the fenced in back yard, and quiet neighborhood. You'll enjoy a short walk into town for date night to get dinner and take in a movie. Seasonal views of the Medomak River make this happy place a lovely and peaceful spot. Schedule your showing today!

24 Glidden St, Waldoboro

Listing courtesy of EXP Realty.

$765,000
3 Beds ⋅ 2 Baths ⋅ 1678586 MLS
What if you were searching for a home, but instead discovered your dream? Sitting on top of a knoll, in the middle of the Dutch Neck community is the property dreams are made of. With an abundance of land filled with nature and wildlife, you won't be able to stop yourself from just slowing down and taking it all in. Over 14 acres of wooded property travels over the Eastern Branch of the Medomak River and ends at the water's edge of Peter's Pond giving 3 separate water frontages to enjoy. Staying close to home in the backyard is just as relaxing around the fire pit or maybe tinkering in the multi-level quintessential Maine red barn. Before spending your days exploring the property, picture all of your morning coffees on the back deck or in the light-filled 3-season sunroom. Walk across the wide plank pine floors to an open kitchen layout with updated appliances to cook your favorite meal or choose a book to read from one of the large built-in bookshelves in the primary living room. With an extra den, separate dining area and a full bathroom downstairs, you will find that the rooms are perfectly divided to create a space for entertaining or just some quiet time. Upstairs you will find an oversized primary bedroom with a sitting area as well as two other bedrooms and a full bath. Additionally, important updates have been made to this home such as new windows and wiring, but all of the charm remains. Being a part of Dutch Neck doesn't just give you an address, it gives you a true community. Grab a bakery treat from one of your neighbors at the local schoolhouse, attend a yoga class taught by another neighbor or maybe display your own artwork or other creation. The Dutch Neck community is truly a welcoming neighborhood waiting for you to join. Explore this opportunity to make your dream a reality.

763 Dutch Neck Rd, Waldoboro

Listing courtesy of RE/MAX JARET & COHN. rockland@jaretcohn.com
$795,000
3 Beds ⋅ 3 Baths ⋅ 1674661 MLS
Situated on more than 13 private acres with over 300 feet of stunning frontage on the beautiful Medomak River, this exceptional antique Cape offers a rare blend of historic character, remarkable versatility, and an idyllic coastal Maine setting. Rich with warmth and timeless appeal, the home showcases beautifully patinated wide pine floors, three inviting fireplaces, three or more comfortable bedrooms, and two-and-a-half baths. Every room reflects the craftsmanship and charm of a bygone era while providing comfortable spaces. Beyond the home, the possibilities are extraordinary. A unique mini event center is perfect for celebrations, gatherings, workshops, or entertaining, while a separate artist's/writer's studio offers an inspiring retreat. The enormous barn, workshop, and garage provide indoor parking for up to five vehicles, boats, or recreational equipment, making this an ideal property for collectors, hobbyists, or anyone needing exceptional storage and workspace. The grounds are simply breathtaking, with rolling lawns stretching toward the river, mature trees, a classic flagpole, and abundant privacy. The property abuts a large 100+ acre conservation parcel. Whether you're launching a kayak, enjoying a peaceful evening by the water, or simply taking in the ever-changing views, the Medomak River becomes an extension of your backyard. Despite its peaceful, secluded feel, this remarkable property is just minutes from the village of Waldoboro, where you'll enjoy convenient grocery shopping, local restaurants, theater, and everyday amenities. A truly special Maine waterfront estate where history, beauty, and endless possibilities come together.

1793 Friendship Rd, Waldoboro

Listing courtesy of Keller Williams Realty.

$285,000
1674224 MLS
Be a part of Waldoboro's exciting growth while enjoying the peace and privacy of your own waterfront retreat. Nestled just outside the revitalized downtown, this exceptional 7 acre parcel is privately tucked away at the end of a deeded ROW, offering the perfect balance of convenience and seclusion. The property features approximately 270 feet of owned tidal frontage on the Medomak River, rolling fields, apple trees, and beautiful perennial flower beds...a lasting reminder of the property's history as a small flower farm. Whether you're envisioning a year-round residence, seasonal escape, or homestead, the setting offers endless possibilities. Much of the groundwork has already been completed with a drilled well, a professionally designed 3-bedroom septic plan, and a recorded boundary survey, giving the next owner a valuable head start. Just minutes from Waldoboro Village and approximately 15 minutes from Damariscotta, Friendship, and the coast.

679 Friendship Rd, Waldoboro

Listing courtesy of Drum & Drum Real Estate Inc..

$2,450,000
3 Beds ⋅ 3 Baths ⋅ 1663865 MLS
Set between the timeless coastal communities of Waldoboro and Bremen, this remarkable 167-acre saltwater farm offers a rare and enduring connection to Maine's unspoiled past. Held and thoughtfully cared for by the one family for more than half a century, the land reflects a legacy of stewardship, enriched through traditional oxen-powered farming. At its center stands a classic antique Cape Cod farmhouse, rich in character and authenticity, featuring three bedrooms, three baths, a formal dining room, and multiple working fireplaces that evoke the warmth and simplicity of an earlier era. Supporting structures include a garage, a charming carriage house, and a substantial pole barn, offering flexibility for agricultural pursuits, livestock, or inspired new uses. The landscape is both diverse and harmonious, unfolding across open organic fields, a serene stretch of old-growth forest alive with wildlife, and a private peninsula extending into the waters of Broad Cove. Here, sweeping views, tidal access, and exceptional privacy create a setting that is breathtaking. Whether envisioned as a working farm, a private coastal retreat, or a legacy family compound, 275 Harriman represents a truly rare opportunity to own a meaningful piece of Maine's coastal heritage.

275 Harriman Rd, Waldoboro

Listing courtesy of L&S Realty.

$115,000
1657602 MLS

265 Friendship Rd, Waldoboro

Listing courtesy of Beacon Realty.

$152,500
1 Beds ⋅ 1 Baths ⋅ 1639879 MLS
MOTIVATED SELLER!! NEW PRICE. Owner is open to offers!! View the Egales from your back deck as they fish. Tiny Home with a large lot (2.6 acres) with 290 feet of waterfront on the tidal part of the Madomak river. Home is fullyi nsuelated and wired, a genarator is included as is a propane heater. Fireplace adds to the warmth. Home needs a septic, well and power. This has been price out. Interior walls need finishing and so does the bathroom. Home and Deck are 100 feet from the river, so some expansion might be possible. Septic field marked. Gravel road is inplace. Triming of lower branckes would give nice views of the river and the vacant land on the other side.

755 Winslows Mills Rd N, Waldoboro

Listing courtesy of Waterfront Properties of Maine.

$59,900
1658359 MLS
Discover the possibilities with this 3.48-acre parcel tucked away in the scenic rural charm of Waldoboro, Maine. Offering approximately 180 feet of frontage on an unnamed stream, this property provides a peaceful natural setting perfect for your future home or getaway retreat. The land has been surveyed, giving you added confidence as you plan your build, and features a deeded right-of-way access for convenient entry while maintaining privacy from the main road. This lot presents a great opportunity to create a custom residence surrounded by Maine's natural beauty. Whether you're looking to build now or invest for the future, this property combines water frontage, acreage, and seclusion--all within a short drive to Waldoboro's village amenities and the Midcoast region. Call to schedule a showing today!

636 Washington Rd, Waldoboro

Listing courtesy of Pooley Realty Group.

$850,000
3 Beds ⋅ 2 Baths ⋅ 1640937 MLS
MID-COASTAL SALTWATER FARM, pampered and updated circa 1814 center chimney cape retaining many colonial features while offering 21st century amenities, a perfect blend of old and new. Wide pine floors, exposed beams and three original fireplaces create the sense of a by-gone era. Well designed newly installed kitchen with separate working pantry, fireplaced dining room, spacious fireplaced living room with soapstone wood stove, office or den, bedroom, full bath and laundry on the first floor. The second floor consists of an en-suite primary bedroom and bath. Attached barn with hayloft and two stalls that open to the well maintained grounds that surround this fine home. Included are a spacious private granite patio with a ''post & beam'' pavilion, a ''post & beam'' carport, numerous planting beds , a small orchard and forest leading to extensive frontage on a tidal estuary. Potentially ''electric self-sufficient'' with a substantial solar generating station.

935 Dutch Nck, Waldoboro

Listing courtesy of RE/MAX JARET & COHN. rockland@jaretcohn.com
$1,199,000
4 Beds ⋅ 4 Baths ⋅ 1643400 MLS
Tucked into idyllic Butter Point in Waldoboro, this waterfront retreat feels like a secret you've been let in on. The original 1997 cottage is all Maine charm - a stone fireplace, warm knotty pine, and cozy gathering spaces that frame the water just beyond the windows. In 2020, a thoughtful addition was crafted to mirror the classic lines of the original structure while quietly elevating everything with modern, luxury finishes. The result is a seamless blend of old and new: expansive glass that floods the home with natural light, elevated materials throughout, and sightlines that pull your eye straight out to the Medomak River where the Narrows open toward Broad Cove. Massive windows run the length of the waterside elevation, making the tide, sky, and ever-changing light part of the daily rhythm of the home. Whether you're curled up by the fire, gathered around the table, or stepping out with your morning coffee, the connection to the cove is constant and effortless. Outside, the property lives just as large. A substantial barn offers storage for up to four vehicles or boats, gear, and workshop space, which could also be converted to a large apartment for your Airbnb visions. The space is further complemented by ample parking below the house and an additional small garage tucked out back. It's the ideal setup for someone who wants a refined coastal home without sacrificing room for projects, toys, or hobbies. From the handcrafted feel of the original camp to the elevated comforts of the 2020 expansion, this Butter Point property is that rare combination of character, privacy, and truly unforgettable water views—ready to be enjoyed in every season.

101 Butter Pt, Waldoboro

Listing courtesy of Pooley Realty Group. jessicapooleyrealtor@gmail.com
$105,000
1620186 MLS
16.85 acres in Waldoboro with 334' frontage on Medomak River. Property was professionally surveyed in 2025. Currently wooded with loads of potential and several options for your homesite, or multiple lots may be possible with planning approval. Time to dream!

00 Wagner Bridge Rd, Waldoboro

Listing courtesy of Pooley Realty Group. jessicapooleyrealtor@gmail.com
$1,200,000
1661376 MLS
A classic brick building offering 4 floors of versatile living, working, and income-producing options, overlooking the Medomak River. The lower level features a fully equipped wood-fired bakery and prep kitchen with a Pat Manley-built oven, circa 1980, and plenty of prep & proofing space. A large walk-in cooler, sinks, a range, refrigeration, and a loading dock make this a complete manufacturing space. Additionally, there's a stone hearth Blodgett double-decker oven, operation ready. The street-level space is compliant, and set up for a 40 seat restaurant. The second floor is a swing floor. When not occupied by short-term renters, it's a venue for rent or a gathering spot, with a stunning, unique parquet dance floor and electrical capacity for a band. There's an adjacent bar, lounge, restroom, and large Riverview deck. There's also a library and office space. Today, the top two floors are listed on multiple platforms as a short-term rental, sleeping up to six. This area could remain a two-story penthouse or be converted into two apartments. Additionally, it doubles as a wellness retreat with plenty of open yoga space, a cedar sauna, and a jacuzzi tub in the remodeled bathroom. This entire opportunity comes fully furnished and equipped, with minor exclusions. Truly turnkey! Recent improvements include a Carlisle Rubber Roofing system, new hatch and louver access to the roof, heat pumps on all floors, a new Jotul gas stove, newly painted inside and out, and new windows on the Friendship Road side, new siding at the rear of the building, a new compressor for the walk-in, new floors in the commercial areas and upgrades to sewer and Ansel systems. This is an exciting opportunity for a lifestyle change, a move to Maine, and the chance to catch the wave and explore Waldoboro's ongoing Renaissance!

13 Friendship Rd, Waldoboro

Listing courtesy of Camden Real Estate. info@camdenre.com
$1,200,000
3 Beds ⋅ 4 Baths ⋅ 1661395 MLS
A classic brick building offering 4 floors of versatile living, working, and income-producing options, overlooking the Medomak River. The lower level features a fully equipped wood-fired bakery and prep kitchen with a Pat Manley-built oven, circa 1980, and plenty of prep & proofing space. A large walk-in cooler, sinks, a range, refrigeration, and a loading dock make this a complete manufacturing space. Additionally, there's a stone hearth Blodgett double-decker oven, operation ready. The street-level space is compliant, and set up for a 40 seat restaurant. The second floor is a swing floor. When not occupied by short-term renters, it's a venue for rent or a gathering spot, with a stunning, unique parquet dance floor and electrical capacity for a band. There's an adjacent bar, lounge, restroom, and large Riverview deck. There's also a library and office space. Today, the top two floors are listed on multiple platforms as a short-term rental, sleeping up to six. This area could remain a two-story penthouse or be converted into two apartments. Additionally, it doubles as a wellness retreat with plenty of open yoga space, a cedar sauna, and a jacuzzi tub in the remodeled bathroom. This entire opportunity comes fully furnished and equipped, with minor exclusions. Truly turnkey! Recent improvements include a Carlisle Rubber Roofing system, new hatch and louver access to the roof, heat pumps on all floors, a new Jotul gas stove, newly painted inside and out, and new windows on the Friendship Road side, new siding at the rear of the building, a new compressor for the walk-in, new floors in the commercial areas and upgrades to sewer and Ansel systems. This is an exciting opportunity for a lifestyle change, a move to Maine, and the chance to catch the wave and explore Waldoboro's ongoing Renaissance!

13 Friendship Rd, Waldoboro

Listing courtesy of Camden Real Estate. info@camdenre.com

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