$599,000 $111 per sq.ft. Brandon VT Home »

9 Beds | 6 Baths |   Total Sq. Ft. 5385  |  Acres: 0.85
Tuesday Aug 5, 2025
Description: This impressive and generously sized Victorian residence, located in the heart of Brandon, Vermont's celebrated artist community, offers a rare opportunity for those seeking space, charm, and versatility. Thoughtfully updated to blend classic architecture with modern comforts, this home features an expansive layout with 9 spacious bedrooms, 6 bathrooms, and over 5,000 square feet distributed across three levels. The property's history as a successful bed and breakfast, with all the associated infrastructure including an integrated fire alarm system, highlights its commercial potential. Large guest rooms and private baths are ideal for hosting guests, multi-generational living, or even business retreats. Zoned within the Village District, the home offers flexibility for both residential and commercial prospects. Among its many features are two efficient heat pumps for year-round climate control, a well appointed kitchen, separate living quarters for privacy or rental opportunities, and a beautifully landscaped 0.85 Acre lot filled with mature trees and plantings. Ample paved parking supports gatherings or events. A prominent two-story carriage barn enhances the property, providing covered vehicle storage, a sizable workshop, and an expansive storage loft - perfect for storage or potential conversion. Well-maintained and move-in ready, this exceptional property presents a unique blend of historical elegance, practical amenities, and endless potential for its new owners. See MLS Property & Listing Details & 45 images. Includes a Virtual Tour

$625,000 $248 per sq.ft. Brattleboro VT Home »

5 Beds | 4 Baths |   Total Sq. Ft. 2520  |  Acres: 1.19
Thursday Apr 9, 2026
Description: Welcome to Hillwinds and this lovely colonial. With 200 acres of conserved land and trails behind and a wonderful meadow view in the front, this house truly feels a part of the landscape. The main house has four bedrooms and two and a half baths and invites you to step right into your new life in this well cared for and lovingly maintained home. The gardens are in, the drive paved and the garden shed with power is standing ready. The sweet sun room is a nice addition to the living area, just off the kitchen/family room so a great place to expand when entertaining in the warmer months. It overlooks the very peaceful conservancy and is a special place for a quiet read or fun games in the rain. No worries of power outages here with both a gas generator and the new Tesla Powerwall! Above the garage is a versatile space that can be used as a studio, guest room, mother-in-law suite, or a study boasting a mini-split, refrigerator, and three-quarter bath. Enjoy the fire pit in the evening, under the stars. Watch the bluebirds at the birdhouses as they raise their families, the chipmunks that scurry, and the turkeys in the meadow. This is a wonderful neighborhood. Make it yours. Open house Saturday, April 11th 11am - 1pm See MLS Property & Listing Details & 46 images.

$639,000 $248 per sq.ft. Brattleboro VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2573  |  Acres: 1.9
Monday Apr 6, 2026
Description: Beautifully sited on 1.9 acres just off Greenhill Parkway, this tastefully modernized 1940s cape blends architectural pedigree with thoughtful, high end updates. Designed by noted architect James Britton of Greenfield, MA - a contemporary of Royal Barry Wills and long admired for his classic New England forms - the home retains its classic original character, while offering a fully refreshed interior. The 4 BR, 3 BA layout includes a full width living room with wood burning fireplace, a handsome dining room with built-in corner cabinets and a massive, x-pane window overlooking the backyard. The kitchen is a standout, featuring Crown Point beaded frame cabinetry, heated encaustic tile floors, Zellige tile walls, a Liebherr refrigerator, Miele propane cooktop, KitchenAid double ovens, and a custom Pella hydraulic lift awning window - ideal for outdoor entertaining. Rounding out the first floor is a beautifully executed mudroom/laundry created between the kitchen and attached 2 car garage, a private and comfortable den, a spacious formal entry hall, and updated powder room. All bathrooms have been fully renovated with Waterworks fixtures and Toto washlet toilets; two with custom tile showers, heated tile floors, and Visual Comfort lighting. A spacious suite above the garage offers flexibility for a primary bedroom or in law arrangement, offering new solid oak flooring, a walk-in closet, and a decadent bathroom with soaking tub and separate shower. The location is exceptional, being an easy walk to downtown and the park, and privately tucked into an unusually large lot; and with unique, direct access to over 9 miles of trails via a path along the lower edge of the property. A rare combination of history, craftsmanship, and modern comfort in one of Brattleboro's most desirable neighborhoods. The home also comes with original 1944 blueprints and historical materials from the Norton family; the property's first owners. See MLS Property & Listing Details & 37 images.

$795,000 $221 per sq.ft. Brattleboro VT Home »

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 & 37 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

$899,800 $121 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.

$999,000 $204 per sq.ft. Brattleboro VT Home »

Price Change! Reduced by $401,000 down 40% on April 8th 2026
5 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, 35 acres of open meadow, 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.

$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.

$619,900 $167 per sq.ft. Bridport VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 3712  |  Acres: 4
Monday Aug 25, 2025
Description: 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. Peaceful setting, yet located close to Middlebury, Addison Central School District, & easy access to NY. See MLS Property & Listing Details & 60 images.

$699,000 $527 per sq.ft. Bridport VT Home »

Price Change! Reduced by $96,000 down 14% on April 13th 2026
475 Ft. of Waterfront on Lake Champlain
2 Beds | 2 Baths |   Total Sq. Ft. 1326  |  Acres: 10.2
Thursday Oct 9, 2025
Description: Lakefront Homestead Retreat - Gardens, Pasture, and Endless Potential! Discover this rare opportunity to own a property on Lake Champlain with 475' of frontage. This property is ideal for homesteading, hobby farming, horses, or a flower/vegetable farm. Nestled on 10+acres, this property features a charming home with scenic Lake Champlain and Adirondack Mountain views, with open pasture. The home offers a warm, welcoming layout with plenty of natural light, cozy living spaces and a large garage that could accommodate a workshop for the hobbyist. The grounds include established fruit trees , fertile soil for growing vegetables, and ample space for livestock or equestrian use. Enjoy private access to a peaceful lake for boating, fishing, kayaking, or simply relaxing in nature. Put a couple of Adirondack chairs in your back yard and enjoy the view from dawn until dusk. Despite the tranquil rural setting, you're conveniently located just minutes from local country stores, diners and Creemee stands! Within 20 minutes you can be in Middlebury or Vergennes to enjoy the shopping, restaurants, cultural events and employment opportunities -- the best of both worlds. Don't miss this unique property that offers self-sufficient living without sacrificing convenience. Schedule your private showing today! See MLS Property & Listing Details & 40 images. Includes a Virtual Tour

$865,000 $394 per sq.ft. Bridport VT Home »

100 Ft. of Waterfront on Lake Champlain
3 Beds | 3 Baths |   Total Sq. Ft. 2198  |  Acres: 1.65
Thursday Apr 16, 2026
Description: Beautiful lakefront retreat offering 100 feet of direct shoreline and breathtaking panoramic views of both the lake and surrounding mountains. This 10-year-old thoughtfully designed home showcases a Vermont slate foyer and bamboo first floor flooring. Designed for exceptional energy efficiency, including triple pane windows, 10-inch walls, a standing seam metal roof, and modern mini split systems for year-round comfort. The open living spaces connect seamlessly to a large deck with awnings, perfect for entertaining or relaxing in the hot tub, with the added luxury of an outdoor shower. A moveable boat dock enhances easy lake access and waterfront enjoyment. The property also includes a flexible garage/outbuilding with carport and workshop space. There is also a paved driveway for convenience. This property is a rare combination of contemporary design, high performance construction and prime lakefront living. See MLS Property & Listing Details & 50 images.

$575,900 $177 per sq.ft. Bristol VT Home »

Price Change! Reduced by $24,100 down 4% on February 27th 2026
5 Beds | 3 Baths |   Total Sq. Ft. 3248  |  Acres: 0.41
Wednesday Mar 26, 2025
Description: Charming Vermont village home offering the perfect blend of comfort and convenience. This spacious 5-bedroom, 3-bathroom property features 3,248 square feet of thoughtfully designed living space, including a private apartment on the third floor--perfect for rental income or visiting guests. Enjoy breathtaking mountain views from this deep lot with a detached garage, pavilion, and storage shed. The outdoor space provides ample room for gardening, entertaining, or simply relaxing in Vermont's natural beauty. Solar panels help reduce electricity costs while supporting sustainable living. The property's prime location allows you to stroll to local parks, schools, and restaurants, genuinely embracing village life. Outdoor enthusiasts will appreciate being just 25 minutes from Mad River Glen and 30 minutes from Sugarbush for winter adventures. Burlington is 40 minutes away for those seeking urban amenities, while Middlebury College is a quick 20-minute drive. This versatile home offers the quintessential Vermont lifestyle--where small-town charm meets outdoor recreation and modern conveniences. See MLS Property & Listing Details & 35 images.

$850,000 $174 per sq.ft. Bristol VT Home »

6 Beds | 3 Baths |   Total Sq. Ft. 4872  |  Acres: 135
Tuesday Aug 26, 2025
Description: Generate passive income and long-term cash flow with this once-in-a-lifetime opportunity--available for the first time since 1909. Spanning 135 acres of fields, timber, and river frontage, Leaning Barn Farm offers unmatched versatility in the heart of Addison County. Income streams include a maple sugar tap lease, 42 acres of tillable sandy loam soil to lease or farm, timber for logging or firewood, miles of roadside frontage, and an established farm stand, greenhouses, and apartments ready for income. Two dwellings provide options for multi-generational living, farmhands, or rental use--the classic farmhouse is 80% renovated, while a spacious double-wide adds flexibility. A new 4,000 sq. ft. barn and multiple greenhouses support nearly any agricultural pursuit. Most acreage is conserved with the Vermont Land Trust. Baldwin Creek runs through the land, adding natural beauty and value. Owner financing and partnership opportunities available. Just 1 minute to Bristol Falls, 4 minutes to downtown Bristol, and within an hour of major ski resorts. A legacy property offering rare income potential, beauty, and flexibility--ready for its next steward.Motivated Seller. See MLS Property & Listing Details & 60 images.

$525,000 $189 per sq.ft. Brookline VT Home »

Waterfront on River West River
3 Beds | 3 Baths |   Total Sq. Ft. 2772  |  Acres: 1.2
Tuesday Mar 3, 2026
Description: Incredible Opportunity! This fully renovated, move-in ready retreat is perfectly situated on the picturesque West River. Enjoy your own private beach and waterfront lifestyle at its finest. Whether you're seeking a peaceful getaway, a year-round residence, or an investment property with proven short-term rental history, this home checks every box. Inside, the property has been thoughtfully updated from top to bottom: all-new kitchen cabinetry, bathrooms, appliances, utilities, a beautifully finished basement, and even Tesla battery storage for added efficiency and peace of mind. The main level is perfectly suited for single-floor living, offering comfort and accessibility. This home is ideal for those who value ease, style, and access to outdoor adventure. Located just 20 minutes from Brattleboro and within 40 minutes of Mount Snow and Stratton, you're perfectly positioned for skiing, snowboarding, hiking, mountain biking--or simply relaxing by the river. Can be sold fully furnished, less exclusions, this is a rare opportunity to own a move-in-ready riverside gem with strong Airbnb/VRBO rental potential. Kindly refrain from using the driveway on drive-by's unless you have a scheduled appointment. Lastly, please reference the FEMA LOMA in the disclosures for clarification on third-party flood risk estimates; the property is not in a designated floodplain. See MLS Property & Listing Details & 58 images.