$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.

$489,000 $212 per sq.ft. Brattleboro VT Home »

Price Change! Reduced by $10,000 down 2% on April 2nd 2026
4 Beds | 4 Baths |   Total Sq. Ft. 2312  |  Acres: 0.27
Saturday Feb 28, 2026
Description: Welcome to 23 Wilsons Woods Road, a meticulously maintained Colonial-style home that offers the perfect Vermont balance: total wooded privacy combined with absolute convenience. Nestled at the end of a quiet road, this property feels like a secluded retreat tucked into the forest, yet you are literally moments away from Brattleboro's vibrant restaurants, local shops, the hospital, and a thriving arts scene. The standout feature of this residence is the thoughtfully designed addition, which serves as a premier mother-in-law suite or guest wing. This expansive space offers flexible multi-generational living without compromise, featuring its own eat-in kitchen and sitting area, and the high-end luxury of radiant floor heating for year-round comfort. With direct access to a private deck and open patio, it is a seamless blend of indoor-outdoor living. The home's exceptional layout includes 4 bedrooms and 4 bathrooms, providing a natural flow that is perfect for both entertaining and quiet daily life. High standards of maintenance are evident throughout, including recent roof renovations and pristine mechanical systems. Whether you are relaxing on the classic covered wraparound porch or hosting a dinner on the beautiful rear deck, the serene surroundings provide a sense of total calm. This move-in-ready property offers the comfort and quality lifestyle Vermont is known for--quality construction, modern upgrades, and a location that puts the very best of Brattleboro right at your fingertips. Open House April 12th 12pm-2pm See MLS Property & Listing Details & 60 images.

$495,000 $180 per sq.ft. Brattleboro VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2756  |  Acres: 0.79
Friday Feb 13, 2026
Description: Step back in time and discover the enchanting potential of this distinguished 1940 Colonial, perfectly positioned to capture the spirit of Brattleboro. Perched on a generous 0.79-acre level lot, this home offers a rare blend of expansive personal space and convenient in-town living. From the moment you arrive, the classic lines, wood siding, and enduring slate roof hint at the craftsmanship of a bygone era. Inside, the home spans a spacious 2,756 square feet, featuring four bedrooms plus bonus room and three bathrooms that provide ample room for family, guests, or creative pursuits. While the interiors are ready for a thoughtful restoration, the home's historic character serves as a beautiful canvas for your vision. This is a unique opportunity to breathe new life into a property with significant provenance, preserving its architectural soul while infusing it with modern comforts and your own personal style.The true magic of this property lies in its setting. Imagine waking up to sweeping, picturesque views of the West River Meadows, a daily reminder of Vermont's natural beauty right from your back yard. Despite this serene visual escape, you are just a short, pleasant walk from the vibrant heartbeat of downtown Brattleboro, where local shops, dining, and community events await. This residence offers the best of both worlds: a private, historic retreat with the convenience of a walkable, connected lifestyle. There are extensive berry bushes, a vegetable garden, and perennials growing on the property. Don't miss this rare opportunity. See MLS Property & Listing Details & 46 images.

$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 25th 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. Includes a Virtual Tour

$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
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.

$485,000 $163 per sq.ft. Bridgewater VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 2977  |  Acres: 0.23
Saturday Feb 28, 2026
Description: This property is conveniently located in Bridgewater Village, situated midway between Woodstock and the Killington Ski Area. While currently configured as three income-producing units, it offers an outstanding opportunity for a creative conversion back into a single-family residence, with the detached rear unit available to supplement the cost of ownership. Recent updates include a new roof, mini-splits, kitchen renovation and a new heating system. Additionally, the high-visibility location is ideal for an entrepreneur or service provider seeking a home occupation. Please come and see the possibilities for yourself. We require 48 hours' notice for all showings, furniture negotiable. See MLS Property & Listing Details & 27 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.

$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.

$520,000 $381 per sq.ft. Bristol NH Home »

Waterfront on Lake Newfound
4 Beds | 2 Baths |   Total Sq. Ft. 1366  |  Acres: 0.95
Monday Jan 12, 2026
Description: LAKE LIFE IS A GREAT LIFE! EXPERIENCE TIMELESS CHARM AND FLEXIBILITY IN A VACATION COMPOUND LIKE NO OTHER! Tucked into a peaceful wooded environment just a short distance from the clear, refreshing waters of desirable Newfound Lake, this unique property features two beautifully updated cottages designed for hosting guests, accommodating extended family or creating an additional income stream. Here, you'll feel like you're miles away from it all yet you're wonderfully connected to local shopping and a stroll away from favorite dining. Each cottage showcases light-filled interiors with open layouts, soaring ceilings and distinctive natural knotty pine paneling that evokes classic Lakehouse character. Enjoy morning coffee and breakfast in your eat-in kitchen or head outside to bask in dappled sunlight and birdsong. Spend the day paddling, boating or swimming in crystal waters, explore the shoreline with your fishing gear, hike in nearby nature preserves or take in an outdoor gazebo concert or holiday parade. After dinner at nearby Big Catch or a festive cookout with alfresco dining, gather around the fire pit for s'mores and stories under star-filled skies. Retire to restful bedrooms for a good night's sleep and wake up refreshed and ready to do it all again. Live the vacation lifestyle you always dreamed of, create a shared family retreat, or enjoy a strategic investment as you rent one or both cottages. A RARE OPPORTUNITY FOR A LIFETIME OF MEMORIES WAITING TO BE MADE! See MLS Property & Listing Details & 48 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.