$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

$769,900 $257 per sq.ft. Brattleboro VT Home »

Price Change! Reduced by $25,100 down 3% on July 14th 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. Upcoming: house roof replacement, skylight replacement and necessary chimney work. 12/1/25 new System 2000 boiler, recently paved drive and so many beautiful appointments. 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 »

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.

$1,100,000 $275 per sq.ft. Brattleboro VT Home »

Price Change! Reduced by $149,000 down 14% on July 8th 2026
4 Beds | 4 Baths |   Total Sq. Ft. 4491  |  Acres: 25.9
Monday May 11, 2026
Description: Price Improvement! 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

$749,000 $101 per sq.ft. Bridgewater VT Home »

Price Change! Reduced by $50,000 down 7% on June 12th 2026
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.

$1,150,000 $264 per sq.ft. Bridgewater VT Home »

Price Change! Reduced by $50,000 down 4% on June 29th 2026
4 Beds | 5 Baths |   Total Sq. Ft. 4352  |  Acres: 13.68
Friday Jun 12, 2026
Description: Tucked on 13.68 private acres near the north branch of the Ottauquechee River, this one-owner Bridgewater estate was built from the ground up with uncommon care -- and it shows in every detail. With 4,300 square feet of living space (6,700 total), the home is heated by radiant flooring throughout and served by a new furnace/boiler, a private septic system, and a private well known for its delicious water. At the heart of the home, an epicurean kitchen with an adjoining scullery is designed for serious cooking and effortless entertaining, with two dining rooms for gathering. The primary suite occupies its own wing: a fireplace, a full soaking tub, a freestanding sink, a lighted mirror, a shower, and a water closet, plus two walk-in closets -- one complete with its own laundry and sink. A three-car garage with automatic doors adds everyday ease. The land is every bit as remarkable. Rich soils nurture blooming flowers -- the air smells incredible this time of year -- and the property is a true natural habitat where birds, foxes, deer, and the occasional bear wander through. Despite its proximity to the river, the home sits outside the FEMA flood plain. Between Woodstock and Killington, this is Vermont living at its most gracious -- private, peaceful, and built to last. See MLS Property & Listing Details & 60 images.

$1,299,000 $341 per sq.ft. Bridgewater VT Home »

8 Beds | 5 Baths |   Total Sq. Ft. 3814  |  Acres: 6
Wednesday Jan 14, 2026
Description: Situated between historic Woodstock Vermont and the ski slopes of Killington, 7030 US Route 4 provides easy access to the best amenities of the area. The Property has two separate spaces, a standalone two-level garage with ample storage area below, and sits on 6 acres with direct river access. The "Apartment" first floor has an open design with a kitchen, living area, and tucked away bathroom. The second floor holds two bedrooms - all of this with its own entrance. The Main House spreads across three levels, all of which was renovated during 2022 and 2023. The first level hosts a beautiful kitchen, dining table, living room, and a few cozy nooks. Right off the kitchen, there's easy access to an over 600 square foot deck built in 2025 with spectacular field and mountain views. The bedrooms throughout the house are spacious and complimented nicely by updated bathrooms. The attic was converted in 2022 into a beautiful open area, with a small kitchenette, and currently serves as both a play / entertainment area while comfortable holding three beds. Currently, the property is operated as an income producing property - with the apartment rented for $1,100/mo to the property manager. The Main House hosts a mix of short- and medium-term users and provides a consistent revenue stream across all four seasons. This winter (December - March), the Main House will generate an average of $14,679 per month in revenue. Additionally, there are approximately 2 acres of developable land that can easily be connected to sewer. 7030 US Rte 4 provides a rare opportunity for buyers looking for easy access to all the best amenities of the upper valley alongside incredible income potential. Agent is a licensed Vermont Real Estate Broker and sole owner of the property. Agent represents only themselves in this transaction and does not represent the Buyer. See MLS Property & Listing Details & 45 images.

$599,990 $162 per sq.ft. Bridport VT Home »

Price Change! Reduced by $18,010 down 3% on June 26th 2026
5 Beds | 3 Baths |   Total Sq. Ft. 3712  |  Acres: 4
Thursday May 21, 2026
Description: Just In Time For Summer ! Welcome To 4351 Crown Point Road in the Town of Bridport. This West Addison County gem offers buyers the best of both worlds - a home consisting of an 1850s farmhouse retaining all of those well-loved period features, as well as a large modern 1990s contemporary addition. This ensures just the right blend of charm and updated conveniences, for the everyday modern lifestyle. Boasting in excess of 3700 SQFT of finished living space, the 1st floor offers the right balance of open spaces and separation including an office, living room, family room, sunroom, & convenient 1/2 bath. Upstairs you'll find 4 bedrooms plus a 5th bonus room, all are of a good proportion. The primary bedroom suite has vaulted ceilings, its own bathroom as well as a spacious balcony - ideal for  relaxing on and savoring those southwesterly views! The addition was architecturally designed to house space for a spiral staircase leading from the bedroom hallway directly into the family room, this final step awaits the next family to complete when time and focus allows! All the important aspects of the house have been taken care of, from the solid standing seam roof to the immaculate siding and trim work. The modern heating & cooling systems include 4 zones, radiant heat in the majority of the 1st floor, 4 AC heat pumps, and the major benefit of (owned) solar panels. Outside enjoy 4 magical acres, with garden shed & convenient canvas carport. Peaceful setting, yet located close to Middlebury, Addison Central School District, & easy access to NY. See MLS Property & Listing Details & 60 images.

$1,250,000 $278 per sq.ft. Bridport VT Home »

6 Beds | 5 Baths |   Total Sq. Ft. 5600  |  Acres: 40.7
Saturday May 23, 2026
Description: Set on 40 private acres with sweeping views in every direction, this property offers a front-row seat to Vermont's natural beauty from open pastoral fields to the Green Mountains and Adirondacks. The south-facing orientation fills the home with natural light throughout the day, while both sunrises and sunsets become part of everyday life. Designed for comfortable living and easy flow, the home offers the flexibility and space today's buyers are looking for. The first-floor primary suite features a walk-in closet, laundry room, and a spacious bath with both a jetted tub and separate shower. A nearby office provides a quiet work-from-home space or could easily serve as a den or reading room. The heart of the home is the large kitchen and dining area with cherry cabinetry, generous counter space, and a center island ideal for gathering. The living room opens directly into a bright sunroom with access to the wraparound deck, overlooking the in-ground pool, outdoor fireplace and established gardens. The basement is partially finished with several storage rooms, a wine cellar a family room space and all of the utilites. Above the attached three-car garage is a well-appointed in-law or guest suite complete with a living room, bedroom, full bath, and kitchenette. A separate detached building adds even more versatility, offering a workshop, additional garage bay, half bath, separate heating system, and two finished rooms above which are perfect for a home business, studio, gym, or recreation space. The classic red Vermont barn provides additional storage or space for small animals and a whole house generator gives you all the backup you might need! Despite the peaceful setting and exceptional privacy, the property remains conveniently located and is 15 minutes to Middlebury or Vergennes and about an hour to Burlington. See MLS Property & Listing Details & 41 images. Includes a Virtual Tour

$1,799,000 $402 per sq.ft. Bridport VT Home »

Price Change! Reduced by $51,000 down 3% on July 13th 2026
308 Ft. of Waterfront on Lake Champlain
4 Beds | 5 Baths |   Total Sq. Ft. 6538  |  Acres: 9.79
Monday May 25, 2026
Description: Dreams really do come true! This is a rare opportunity to own a practically brand-new custom home showcasing exceptional craftsmanship, premium materials, and breathtaking Lake Champlain waterfront living. Set on approximately 10 private acres with 308 feet of shoreline, this remarkable property offers the perfect blend of luxury, comfort, and recreation. Designed for gathering and entertaining, the spacious home features 4 bedrooms, 4.5 baths, and over 1,700 square feet of beautifully finished lower-level living space with radiant heat. The stunning great room is anchored by a massive hearth, creating a warm and inviting centerpiece for the home. Expansive west- and south-facing Trex decks and a charming waterfront cabana (generator powered) provide the perfect setting to relax, entertain, and take in unforgettable sunsets over the lake. Built with quality and efficiency in mind, the home includes closed-cell insulation throughout, top-of-the-line Marvin windows, maple flooring, individually controlled blinds, an air exchanger, whole-house generator, and low-maintenance siding and trim. The heated three-car garage features an epoxy floor for a polished and functional finish. Car enthusiasts, hobbyists, and outdoor adventurers will appreciate the impressive 40' x 60' Lester metal building, just three years old, complete with a foundation, metal roof, water, power, and a drive-on four-post car lift. A floating boat dock with jet ski ramp completes this extraordinary waterfront property, making it easy to embrace the very best of lakefront living. This home is being sold furnished, including the spa pool! See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$420,000 $125 per sq.ft. Bristol VT Home »

Price Change! Reduced by $20,000 down 5% on June 22nd 2026
6 Beds | 3 Baths |   Total Sq. Ft. 3366  |  Acres: 0.51
Monday May 18, 2026
Description: In town, there is one undeniable property that immediately catches your eye and captures your imagination. Located at 28 West Street, this spectacular, once-in-a-lifetime Bristol Village home offers an extraordinary blend of historic grandeur, massive scale, and a rare live-and-work opportunity. Sitting proud on a gorgeous, 0.51-acre lot, this property puts you a stone's throw from the vibrant downtown shops and restaurants, and gives you a front-row seat to Bristol's legendary Fourth of July parade. Spanning over 3,300 square feet, the residence is rich with architectural character, showcasing beautiful original trim and a cozy wood fireplace that anchors the living space. With six generous bedrooms and three bathrooms, the floor plan offers an abundance of space and flexibility. The home has been thoughtfully maintained where it counts, featuring a dry basement, a Buderus boiler, a brand-new septic system installed in 2021, and has been rewired with a newer electrical panel. For those who need extra space for vehicles, hobbies, or storage, the property includes an oversized, detached two-car garage complete with an unfinished second level. What truly sets this village gem apart is its flexible zoning, which allows for mixed-use options including professional offices and commercial space. Whether you dream of launching a boutique business from home or keeping your work and residential life seamless, this layout provides the ultimate template for a live-and-work lifestyle. The ideal buyer is someone ready to embrace a rewarding project; while the home boasts incredible bones and a commanding presence, it is ready for cosmetic updates, offering the perfect canvas to bring your personal touch and design vision to every room. Opportunities of this scale, location, and versatility rarely hit the market in Bristol Village--bring your ideas and revive this local icon into your dream masterpiece. See MLS Property & Listing Details & 60 images.