$300,000 $166 per sq.ft. Brattleboro VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1808  |  Acres: 0.12
Thursday Jul 31, 2025
Description: Bright Sunny, south facing! 2 stacked flats just perfect for multi generational living! Inside access with both formal front stair and back utility stairs, so easy for caring for family members, or a plan for aging in place with a care giver. Rent one or both for a money maker. This owner is owner occupying both flats. Plenty of off street parking, a sweet side porch and just a bit of a yard to care for. Near down town,, MOOVER route, hospital and all the other good stuff. Quite, level short street, with easy access. Come join the neighborhood! Only the first floor is available to show on first showing. Please have all buyers qualified before requesting an appointment. See MLS Property & Listing Details & 2 images.

$325,000 $147 per sq.ft. Brattleboro VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 2209  |  Acres: 0.21
Wednesday Dec 18, 2024
Description: Fabulous potential with this in-town home on a great neighborhood street just a few short minutes to downtown Brattleboro where you'll find shops, restaurants, galleries, and more! Close to the hospital, schools, and points north and south with easy access to Rt 91. This home retains much of the original woodwork with bulls eye trim for the doors, an elegant staircase with two stained glass windows, and glowing wood floors. First floor has a bedroom option and a full bathroom, there's a full bathroom on each floor! Plenty of room for everyone with three more bedrooms and a bathroom on the second floor. There is an additional room on the second floor with separate entrance that would make a great office, and the third floor offers an in-law potential with a one bedroom studio apartment. There are two furnaces and two oil tanks, one for the first floor, one for the second floor, and a propane wall unit for the third floor. See MLS Property & Listing Details & 28 images.

$335,000 $275 per sq.ft. Brattleboro VT Home »

4 Beds | 1 Baths |   Total Sq. Ft. 1216  |  Acres: 0.18
Friday May 29, 2026
Description: Located in one of Brattleboro's desirable neighborhoods, this inviting 4-bedroom home offers a comfortable layout, great natural light, and convenient access to schools, parks, trails, shopping, and downtown amenities. The bright living room features a large bay window that fills the space with natural sunlight, while the kitchen offers ample cabinet space and overlooks the backyard. With two bedrooms and a full bathroom on the first floor, the layout offers flexibility for a variety of living needs. Outside, enjoy a spacious backyard with room to garden, gather, or simply relax. A warm and welcoming home ready for its next chapter. Open house Saturday, 5/30 from 1-3 and Sunday 5/31 from 11-1 See MLS Property & Listing Details & 36 images.

$339,000 $151 per sq.ft. Brattleboro VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2250  |  Acres: 0.2
Monday Jun 8, 2026
Description: Step into a world of artistic whimsy and historic allure at 65 Cedar Street, a property overflowing with character, magic, and boundless potential. Nestled in an ideal location with an entrance to the beloved Retreat Trails, this unique home offers an enchanting escape from the everyday. Outside, the property is embraced by beautiful, mature gardens cultivated over time in a spirit of enchanting "benign neglect"--where nature and romance intertwine to create a storybook setting that will capture your heart from the moment you arrive. Inside, you will find a spacious layout featuring 4 bedrooms and 2 full baths spread across 2,250 square feet of versatile living space. The home has been thoroughly cleaned out and deep-cleaned, presenting a pristine, blank canvas with exceptional, rock-solid "bones" ready for its next chapter. Fine historic details anchor the home, from rich wood floors to timeless built-ins. At the heart of the home sits a magnificent centerpiece: a vintage Vermont Iron Stove Works stove, radiating authentic New England warmth and charm. The footprint continues to impress with a bright, beautiful sunroom perfect for morning coffee, a large attached 2-car garage providing excellent storage, and a expansive bonus space tucked away in the finished attic. This property is being offered in "as-is" condition and does not include appliances, making it the ultimate dream project for those looking to invest sweat equity into a truly remarkable historic home. Bring your vision to finish the cosmetic upgrades and unlock the true grandeur of this whimsical masterpiece. OPEN HOUSE SUNDAY, JUNE 14TH | 12:00 PM - 2:00 PM Come experience the magic and explore the incredible potential of this one-of-a-kind home in person! See MLS Property & Listing Details & 40 images.

$369,900 $206 per sq.ft. Brattleboro VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1800  |  Acres: 0.25
Thursday May 28, 2026
Description: Sweet and charming from an era of wonderful wood work, polished floors and rooms with a purpose. This home has a lovely big kitchen with a peninsula for baking prep, formal dining with built in china cabinet, living room and an first floor bedroom with 1/2 bath. Since the basement is walk out, the back porch is 2nd level, above the bugs, and overlooking the private back yard. Fenced for a dog, the side yard pops off the kitchen deck for easy pet access. Gardens and a small rivulet in the back complete this special setting. In-town corner lot, ready to go! See MLS Property & Listing Details & 28 images.

$499,000 $174 per sq.ft. Brattleboro VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2874  |  Acres: 0.19
Saturday May 9, 2026
Description: Beautifully maintained, 1880s, in-town Victorian blends timeless elegance with modern comfort. The large, light-filled kitchen combines with an open, cathedral ceiling dining area inviting the gathering of family and friends. The renovated kitchen has granite, stainless steel appliances, and laundry area. Soaring, 9 ft ceilings create light-filled rooms. Elegance of timeless design and detailed wood trimmed finishes are throughout with crafted moldings framing arched and stain glass windows, custom fireplace mantles and functionally flexible built-ins. Enjoy the old-world charm of two covered porches. The expansive first floor has lovely potential for those wanting first floor accommodations. An ornately crafted staircase rises gracefully to the second floor with four bedrooms, two full baths and the continuation of flooding sunlight. The outdoors offers gorgeous stonework, lush perennial plantings and a magical patio. So close to downtown's Brattleboro Museum, Art Center, Galleries, Cafes, and more! Convenient to ski mountains and ready access to Boston and NY City. Visit this beloved, period home to experience a world of gentle elegance. See MLS Property & Listing Details & 51 images. Includes a Virtual Tour

$749,000 $250 per sq.ft. Brattleboro VT Home »

Price Change! Reduced by $46,000 down 6% on June 9th 2026
4 Beds | 4 Baths |   Total Sq. Ft. 3600  |  Acres: 11.4
Wednesday Apr 1, 2026
Description: Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on almost 2 acres of landscaped grounds with lawns, stone walls & gardens, plus an adjoining 9.4 acre woodland lot with snowshoe trails in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through a covered porch that opens into a marble floored foyer with skylight, entry closet and stained-glass windows. Adjacent, opens into a warm, spacious family room with cherry wainscoting, a gas stone fireplace, curved architectural accents and mud room access. The formal living room features a brick fireplace and is surrounded by classic post & beam architecture and stained glass windows. The open kitchen & dining area are ideal for entertaining and impress with cherry cabinetry, quartz countertops, stainless appliances, and sliders to an expansive deck with serene views. A den, half bath, and laundry closet complete the main level. Upstairs offers four bedrooms, including a stunning primary suite with cathedral ceiling, triple closets, fireplace, and Palladian windows. There is a tucked-away guest room that enjoys a private ¾ bath. The finished lower level includes a generous game room with wet bar, half bath, propane stove, & TV area--pool table included! A detached 2-car garage with storage, a garden shed, and timeless craftsmanship throughout make this a truly rare offering. See MLS Property & Listing Details & 38 images.

$795,000 $248 per sq.ft. Brattleboro VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 3212  |  Acres: 4.37
Monday Apr 6, 2026
Description: Welcome to Juniper Ridge! Where you will find superior craftsmanship, a private haven, and neighbors only one can dream of. As you enter the foyer of this custom built home, you'll feel its character & elegance with vaulted ceilings, arched doorways, terracotta tile and balconies lined with bookshelves. The home was built with attention to the flow, energy and natural light. The kitchen has Italian ceramic countertops & butcher block, including a dinette with southern light. With an open concept living/dining arrangement, the living room has lovely radiant wood stove heat. The adjacent dining area is drenched in sunlight. The home affords views of the West River Valley and Green Mountain vistas as far as Hogback Mountain. The first floor offers a fabulous great room, 2 fireplaces, an office, a sun room with hot tub, a laundry room and decks for admiring the sunrises and sunsets. The second floor is exceptional with three expansive primary en suites and two more rooms perfect for study, meditation, or extra bedrooms if needed. The two car garage has plenty of room for a workshop and the landscape features stone walking paths, wildflowers, perennials, pear trees as well as an in-ground pool. Brattleboro offers that small town charm with culture everywhere, from our music center, the Brattleboro Museum and Art Center, galleries, cafes, and more. Convenient to ski mountains & easy access to Boston and NYC. The next owner will truly be fortunate! Showings start Friday, April 10th by appointment. See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$899,000 $235 per sq.ft. Brattleboro VT Home »

Price Change! Reduced by $501,000 down 56% on May 7th 2026
4 Beds | 5 Baths |   Total Sq. Ft. 4908  |  Acres: 103
Tuesday Oct 7, 2025
Description: Remember when you were 6 and the Hundred Acre Wood seemed as big as the whole world? Now is the time to write your own story...and live in your own Hundred Acre Wood....only this one is grown up with 103 acres, rolling meadows, about 1/4 mile bordering the Whetstone Brook, a great barn, nearly 4000 square feet of living space and so many stories to live! With a perfect location...minutes to town, the interstate and all you need for any lifestyle... you are tucked away in the gentle rolling meadows of home. High speed internet is available for home workers or streamers. The small touches are amazing, marble sink toppers from Dartmouth College and dramatic imported faucets tipping the scale of lovely. Delicate adz work in the original wing is amazing and a rarity and the slate floor entry with an inlaid heart to greet you every time you come home is a warm gift from the owner. A huge real cook kitchen with professional Garland range, commercial fridge and soapstone tops galore will tease you into your finest meal ever. Dig deep, find the child who dreamed of the Hundred Acre Wood, and step foot into that dream, in the lovely, comforting hills and meadows of Vermont. Come home for a lifetime. *Age of home is the best estimate seller has. See MLS Property & Listing Details & 54 images.

$899,800 $156 per sq.ft. Brattleboro VT Home »

5 Beds | 8 Baths |   Total Sq. Ft. 7430  |  Acres: 18.11
Wednesday Jun 11, 2025
Description: Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of room for everyone in five bedrooms (and of course 7 bathrooms), a choice of large or cozy living rooms and an office to work from home. Toast your toes at either fireplace or soap stone wood stove. Invite your circle of friends to yoga, parties or create a media room in the huge, finished walk-out basement family room, plumbed and wired for a second kitchen, with ½ bath, easily converted to extended family suite. 47x21 bonus room with skylights and ample windows overlooking the grounds is perfect for play/gym space, artist studio, etc. 3 car detached heated, finished garage/workshop with storage above. Create a cross-country ski track for moonlight nights. Watch for fireflies in the meadows and see the forest creatures explore their world. A one-of-a-kind property with so much to love; solid, expansive architecture, two staircases, windows everywhere, gleaming wood floors and well positioned, dimmable lighting, bringing together classic and fun, this home was designed for those who love organization with oodles of storage space. The heart of Vermont is here! See MLS Property & Listing Details & 51 images.

$1,249,000 $312 per sq.ft. Brattleboro VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 4491  |  Acres: 25.9
Monday May 11, 2026
Description: Escape to this beautifully updated home set on 25.9 idyllic acres of forests, meadows and stone walls, while only minutes from amenities including the local creekside farmers market, treasured food co-op and Brattleboro's vibrant downtown. A gorgeous stone floor and blown glass windows in the entry vestibule set the tone as you are drawn to the stunning great room. The home tastefully captures the historic essence of Vermont with its chestnut beams, wide plank flooring and stylish yet unpretentious design. Interior features offer the perfect balance of grandeur and intimacy with oversized windows that bathe the rooms in natural light, 3 fireplaces and authentic lighting. The kitchen is a culinary haven with state-of-the-art appliances and stunning Brazilian countertops, providing ample workspace and an eat-in area. The first floor also offers a formal dining room, a guest/primary suite with a private entrance and laundry, an office, and it's completed by a sitting room where the current owners gather around the piano. Upstairs you'll find a generous primary suite, two bedrooms, and one with a connecting room, an ideal playroom or office. The walk-out basement is partially finished with a workout room, laundry room and abundant storage. The house includes high-speed fiber internet and a whole-house generator. The attached 2-car garage is heated and a second heated detached 2-car garage with a finished loft above is perfect for playing pool and foosball with family & friends. Relaxation comes easily by the inviting in-ground pool overlooking tranquil woodlands, the stone-terraced landscape and native wildlife. This special property is nestled in a friendly community on a country road, adjacent to 367 acres of protected land with trails perfect for hiking, biking and snowshoeing. Just 2 hrs to Boston, 3.5 hrs to NYC with direct Amtrak to NYC. Easy drive to ski mountains. See MLS Property & Listing Details & 55 images. Includes a Virtual Tour

$439,000 $250 per sq.ft. Bridgewater VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2066  |  Acres: 0.93
Tuesday Jun 9, 2026
Description: Welcome home to this spacious 4-bedroom Cape ideally located between Killington and Okemo ski resorts and just a short drive to charming Woodstock, Vermont. Set on nearly an acre, this property offers the perfect opportunity to enjoy Vermont living with year-round outdoor recreation, dining, shopping, and local attractions nearby. Step inside from the covered front porch into a practical mudroom with a half bath and laundry area. The heart of the home is the bright, oversized kitchen featuring new appliances, a pellet stove, and plenty of space for dining and gathering. The large living room provides ample room for entertaining or relaxing. The main level also offers two bedrooms, a full bath, and a walk-in closet for added storage. Upstairs you'll find two additional bedrooms and a full bath, providing space for family, guests, or a home office. The partially finished basement expands the living area with a family room, pellet stove, and second kitchen, offering excellent potential for recreation, hobbies, or extended living needs. Outside, enjoy the privacy of the spacious yard, while recent updates including a standing seam metal roof provide peace of mind. Whether you're looking for a primary residence, vacation getaway, or investment opportunity, this Vermont home is perfectly positioned to enjoy everything the area has to offer. See MLS Property & Listing Details & 31 images. Includes a Virtual Tour

$799,000 $108 per sq.ft. Bridgewater VT Home »

7 Beds | 9 Baths |   Total Sq. Ft. 7428  |  Acres: 1.5
Thursday Feb 19, 2026
Description: The ideal property for a SKI CLUB! 7 bedrooms! 6 bathrooms! An immaculate, professionally appointed commercial kitchen! Spacious common rooms and dining areas! A classic and inviting bar/lounge area! An interior with the true Vermont style appeal of exposed beams, wood floors and a stone faced fireplace! This inviting New England style building is perfectly situated midway between world class skiing at Killington and the numerous year round amenities of shopping, dining and cultural events of historic Woodstock Village! The highly visible and well known property is easily accessed year round off a well maintained paved road. Conveniently separated within this highly versatile complex is a comfortable residence well suited for rental income as an apartment or perhaps for use as the residence of an on site property manager. Outside dining/lounging areas add further appeal in the warmer months! With commercial zoning, the possibilities are unlimited for entrepreneurial dreams! See MLS Property & Listing Details & 40 images.

$849,000 $335 per sq.ft. Bridgewater VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 2534  |  Acres: 1
Saturday Apr 4, 2026
Description: Turn-key mountain retreat just minutes from Killington or Woodstock! Completely renovated 4-bedroom, 4-bath home blends modern updates with classic Vermont character - featuring an updated kitchen, new bathrooms, a large mudroom with built-in ski storage, and scenic mountain views showcased by oversized custom windows that fill the home with natural light. Multiple living spaces and the expansive deck make this home truly perfect for entertaining large groups in any season. The list of recent improvements is extensive. Some highlights include: all new mini-splits and Rinnai heaters, new tile/hardwood flooring, fresh exterior paint, and a timber frame portico to welcome you home. Located just 9 minutes to the Killington Skyeship Gondola, this property checks all the boxes for a high-demand rental or personal escape. See MLS Property & Listing Details & 39 images.

$995,000 $350 per sq.ft. Bridgewater NH Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2843  |  Acres: 6
Tuesday May 12, 2026
Description: Snowbirds and snowmobile enthusiasts take notice! Perched high along a scenic ridge in Bridgewater, this historic 1912 Cape Cod-style home was Bridgewater's very first summer residence. Set on 6 private acres, the property blends timeless New England charm with thoughtful modern updates and breathtaking mountain views. This unique home features 4 spacious bedrooms, 3 finished baths, and a partially completed fourth bath in the walk-out lower level. Enjoy panoramic views from the covered porch or entertain on the beautiful paver patio surrounded by expansive lawns and peaceful natural beauty. The lower level offers excellent potential for a game room, home theater, wine cellar, or private retreat. Perfect for outdoor enthusiasts, the property offers direct access to snowmobile trails and is close to hiking, biking, lakes, and all the recreation the Lakes Region is known for. Located on a Class VI road that is not town maintained in winter, the home is ideal for seasonal owners, adventurous buyers, or those seeking a true getaway. Owners may plow for year-round access or enjoy winter access by snowmobile. A rare opportunity to own a one-of-a-kind historic property in low-tax Bridgewater. Private showings by appointment. See MLS Property & Listing Details & 59 images.