$299,000 $160 per sq.ft. Brattleboro VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 1872  |  Acres: 0.22
Sunday Jun 14, 2026
Description: Move-in ready and full of potential, this charming Brattleboro home is ready for its next chapter. The main level features a bright, open-concept layout with a spacious kitchen and comfortable living area, creating an ideal space for everyday living and entertaining. Filled with natural light, the living room opens directly onto a private rear deck overlooking a manageable backyard--perfect for relaxing, gardening, or outdoor gatherings. Upstairs, the bedrooms offer comfortable accommodations with the opportunity to add a full bathroom in the future, allowing the home to grow with your needs. The lower level includes a separate in-law suite complete with its own private entrance and laundry area, offering flexibility for guests, multi-generational living, a home office, or potential rental income. Conveniently located, the property is less than a block from the Vermont Country Deli and within walking distance of the Brattleboro Farmers' Market, Memorial Park, and recreation fields. Easy access to Interstate 91 makes commuting simple while keeping downtown Brattleboro's shops, restaurants, arts, and entertainment just minutes away. Whether you're searching for a primary residence, an investment property, or a home with income-producing potential, this well-priced property offers an excellent opportunity. See MLS Property & Listing Details & 37 images.

$300,000 $272 per sq.ft. Brattleboro VT Home »

3 Beds | 1 Baths |   Total Sq. Ft. 1522  |  Acres: 0.48
Friday Jul 10, 2026
Description: Welcome to this lovingly maintained 3-bedroom, 1-bath ranch located in the sought-after Carriage Hill neighborhood of West Brattleboro. Where affordability & opportunity come together in this move-in ready home. Whether you're taking the exciting step into homeownership or searching for a home that lets you spend less time on upkeep and more time enjoying life. The open-concept, light filled living room and eat-in kitchen create a comfortable, welcoming space that feels like home the moment you walk in. South facing windows fill the living room with an abundance of natural light, creating a bright and inviting atmosphere throughout the day. Just off the kitchen, step onto the back deck overlooking the spacious, fenced-in backyard. Mature trees provide natural shade and privacy, while the property extends well into the woods with established walking trails, offering a setting to explore and enjoy nature right from your own backyard. Back inside, you'll find three comfortable bedrooms and a full bath, all conveniently located on the main level. The partially finished basement adds valuable living space with a versatile bonus room, a rec room or office space, and a spacious utility area, providing flexibility for hobbies, fitness space, or additional storage. Thoughtfully cared for over the years, this home offers peace of mind with a roof that's approximately seven years old and a hot water heater that's just two years old. Additional features include town water and sewer, a paved driveway, and a functional layout designed for today's lifestyle. Enjoy easy access to shopping, local restaurants, coffee shops, Brattleboro Memorial Hospital, Interstate 91, public transportation, schools, and countless everyday conveniences, all while coming home to the peaceful charm of an established neighborhood. See MLS Property & Listing Details & 57 images.

$300,000 $286 per sq.ft. Brattleboro VT Home »

3 Beds | 1 Baths |   Total Sq. Ft. 1050  |  Acres: 0.15
Thursday Jul 2, 2026
Description: Tucked in near schools, hospital, shopping and a short walk to fishing and a canoe ride. Room enough for a garden, play space and just the right size for new beginnings. Nice sun porch doubles a a mud room, kitchen is huge with room enough for an island, a sweet spot with lots of potential. See MLS Property & Listing Details & 12 images.

$309,000 $358 per sq.ft. Brattleboro VT Home »

Price Change! Reduced by $10,000 down 3% on July 6th 2026
3 Beds | 1 Baths |   Total Sq. Ft. 1140  |  Acres: 0.41
Monday Jun 22, 2026
Description: ***Open House Saturday 7/18 from 11am-2pm** Welcome to a home where everyday living feels just a little more special. Offering three comfortable bedrooms and a functional, inviting layout, this property is designed for everything from quiet evenings at home to hosting family and friends. The true highlight is the incredible backyard, a rare, fully fenced, level oasis that's ready for every season of life. Fire up the grill on the spacious back deck, let the kids and pets roam freely, plant the garden you've always wanted, or gather around a fire pit under the Vermont stars. This is the kind of outdoor space buyers dream about and seldom find. Located in one of Brattleboro's most convenient neighborhoods, you'll love being just minutes from vibrant downtown shops, local restaurants, schools, parks, and year-round community events while still enjoying the peace and privacy of your own backyard retreat. Whether you're grabbing a morning coffee, exploring the local arts scene, or taking advantage of nearby hiking and recreation, everything you love about Brattleboro is right at your fingertips. This isn't just a place to live, it's a place to make memories. This home offers the lifestyle you've been waiting for. Don't miss your chance to experience everything this exceptional property has to offer. List Agent is related to the Sellers See MLS Property & Listing Details & 38 images.

$319,000 $207 per sq.ft. Brattleboro VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1539  |  Acres: 0.09
Thursday May 7, 2026
Description: Charming and conveniently located, this inviting home is situated less than one mile from the heart of Brattleboro Village. Offering 3-4 bedrooms, including a first-floor bedroom for added flexibility, the home features a practical mudroom entry and a bright, sun-filled dining porch just off the kitchen. The basement provides a dedicated workshop area, laundry space, and ample additional storage. Set on a manageable 0.09-acre lot, the property is bordered by mature trees along the rear for added privacy, while the open yard offers excellent potential for gardens and outdoor enjoyment. A cozy screened-in porch tucked behind the house creates the perfect retreat for relaxing during the warmer months. See MLS Property & Listing Details & 44 images. Includes a Virtual Tour

$319,000 $245 per sq.ft. Brattleboro VT Home »

Price Change! Reduced by $20,000 down 6% on June 19th 2026
3 Beds | 1 Baths |   Total Sq. Ft. 1300  |  Acres: 0.13
Wednesday May 20, 2026
Description: Located in one of the area's most desirable and close-knit neighborhoods, this beautifully preserved 1929 home blends timeless character with thoughtful updates. Featuring hardwood floors, natural woodwork, custom built-ins, classic wainscoting, and a welcoming mudroom, the home retains the charm and craftsmanship buyers love. The open and inviting first floor offers generous living space and a formal dining room, complemented by a retro-inspired kitchen full of personality. Just off the living room, the enclosed south-facing porch with newer windows may become your favorite place to relax and unwind. Upstairs offers 3 bedrooms, a bright and cheerful bath, and access to an incredible attic space with exciting potential for a studio, yoga room, office, or expanded living area. Outside, the landscaping is a delightful surprise, featuring striking artistic bluestone details and a peaceful water feature that create a private, zen-like setting rarely found in town. This is a wonderful opportunity to own a character-filled home in a neighborhood known for its quality homes, strong sense of community, and convenient access to restaurants, shopping, and local amenities. See MLS Property & Listing Details & 27 images.

$320,000 $278 per sq.ft. Brattleboro VT Home »

Price Change! Reduced by $33,900 down 11% on June 29th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1152  |  Acres: 0.23
Monday Feb 2, 2026
Description: First time offered, EVER... built and loved by the current family, it is time to pass the keys to a new generation of owners ready to put their own love and dreams into this sweet home. Just across from the high and middle schools, around the corner from Oak Grove grade school, and down the street from the hospital and shopping. There is a first floor bed and bath for aging in place, but 2 big bedrooms and full bath up! The full basement has room for a workshop, storage or game room. Drive and carport are paved for easy maintenance. Huge shed in the back for storage or lawn care tools. Just what you have been waiting for! See MLS Property & Listing Details & 20 images.

$329,000 $257 per sq.ft. Brattleboro VT Home »

Price Change! Reduced by $10,000 down 3% on June 1st 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1280  |  Acres: 0.15
Thursday Apr 30, 2026
Description: Lovely level lot, close to schools, hospital, shopping, State park and downtown. The best of everything, and BRAND NEW!!! Be the the envy of all your friends, with this wonderful, open concept, one level home. Primary bedroom on one end with an ensuite for privacy! New, shiny appliances, good sized island for cooking or hanging out and both a tub and a walk in shower. Special in so many ways, easy to show. See MLS Property & Listing Details & 17 images.

$340,000 $267 per sq.ft. Brattleboro VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1272  |  Acres: 0.32
Wednesday May 27, 2026
Description: Perfectly situated at the top of the hill on highly desirable Carriage Hill in West Brattleboro, this delightful yellow ranch offers the perfect blend of neighborhood comfort and exceptional curb appeal, accented by a lovely stone pathway and beautiful exterior gardens. Step out back to discover your own private oasis featuring a spacious wooden deck with a gorgeous overhead pergola, custom built-in bench seating, and an attached screened-in porch that looks out over a lush green backyard complete with a handy storage shed. Inside, the home boasts a bright, expansive living room with durable flooring and a mini-split system for efficient year-round comfort. The generous eat-in kitchen features warm wood cabinetry with vibrant turquoise accent shelving, tile flooring, and a large window overlooking the serene backyard. Comfortable bedrooms with unique, colorful accent walls and a dedicated home office or study space under a cheerful blue ceiling provide a highly versatile layout. Complete with two functional bathrooms--including one full bath with a tub/shower combo and a second featuring a retro blue shower stall--this home is ready for its next chapter. Come see all this West Brattleboro gem has to offer at our upcoming open house on Sunday, May 31st from 2:00 PM to 4:00 PM! See MLS Property & Listing Details & 43 images.

$344,900 $223 per sq.ft. Brattleboro VT Home »

Price Change! Reduced by $4,100 down 1% on July 6th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1550  |  Acres: 0.41
Thursday May 28, 2026
Description: Enjoy the privacy of your own space secluded from the rest of the world. Enjoy the comfort of a country setting in town. Look through the tree tops over the roofs of houses below on one side, onto a garden on another side, and onto a wooded hillside on the rest. Nature surrounds this immaculate house on a hill. Amenities include stone walls, a dog cage, a fire pit, raised gardens, a convenient 2-car garage, a mudroom with a closet off the garage, a workshop on the basement level, a pantry with spice racks, a palladian window and ceiling fan in one bedroom, and privacy, privacy, privacy. The seller spent a lot of time and money preparing the house for sale; see the list of improvements in the Documents section of this listing. Includes a 1/34 share of common interest in the Wilsons Woods land. Near the middle school and high school, hospital and shopping. Showings begin on Friday 6/5/26. See MLS Property & Listing Details & 60 images.

$369,900 $243 per sq.ft. Brattleboro VT Home »

Price Change! Reduced by $15,100 down 4% on June 23rd 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1521  |  Acres: 0.15
Thursday May 28, 2026
Description: Neighborhood home! Living in a sweet neighborhood is a lifestyle choice. Walk to schools, playgrounds, and shopping. This vintage home has an added features of roof top solar, 2 car direct entry garage, a fenced-in yard, and lots and lots of gardens. The classic front porch is on everyone's list of must haves. The neighborhood is perfect for long evening strolls or a brisk walk at dawn. Inside there is a huge living room for hanging out with friends, entertaining or movie night. Work at home? You will love the corner office, age in place with first floor bedroom and bath...So nice, just the right location and just the right home. See MLS Property & Listing Details & 19 images.

$475,000 $198 per sq.ft. Brattleboro VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2400  |  Acres: 0.14
Friday May 15, 2026
Description: Set among a row of classic "painted ladies" on picturesque Chapin Street, this gracious Victorian home offers timeless charm just a short stroll from a vibrant downtown. A welcoming front yard with picket fencing and a stone walkway sets the tone, while the rear yard is fenced and features a large covered porch with access to the 2 car garage, which includes overhead storage. Enter through the expansive covered porch into a formal foyer, where period lighting, a powder room, and a handsome original staircase immediately showcase the home's historic character. The front parlor features a bay window and distinctive bullseye molding, while the formal dining room is equally impressive with its own bay windows and a handsome fireplace with an elegant mantle and surround (has a woodstove insert). The spacious country kitchen is warm and inviting, offering cherry cabinetry, large sun-filled windows, and beautiful wood flooring. A flexible first-floor bedroom or family room includes an en suite bath and direct access to a covered rear porch--ideal for guests or easy single-level living. Upstairs, a generous landing with rear staircase leads to a spacious primary bedroom featuring a large en suite bath and convenient laundry. Two additional well-proportioned bedrooms offer excellent closet space, along with a dedicated office. Additional features include a full basement and walk-up attic, providing abundant storage or expansion potential. Rich with period details--from exquisite woodwork and original doors to classic lighting and flooring--this gracious Victorian is a true beauty, seamlessly blending historic elegance with everyday comfort. Showings begin 5/19/26. See MLS Property & Listing Details & 31 images.

$595,000 $274 per sq.ft. Brattleboro VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2172  |  Acres: 0.42
Monday May 4, 2026
Description: Immaculate! Lovingly reimagined over two decades, this impeccable residence blends thoughtful design with modern sustainability. The heart of the home is a chef's kitchen with ample counter space and a spacious pantry with an integrated dining area--perfect for entertaining. Relax in the stunning living room, anchored by a gas insert fireplace crafted by a very talented local mason. Outdoor living is elevated by a light-filled sunroom overlooking a lush backyard complete with raised garden beds and blueberry bushes. Unique features include a former garage transformed into a private guest studio with a Murphy bed, and a new, oversized two-car garage with a clever "drive-through" door for garden access. There is a 40x10' attic space, perfect for tons of storage, or if more living space is needed, it may be finished. Hot water pipes are already located there. Complete with an array of solar panels,{owned}, heat pumps, a whole-house generator, and the potential for single-level living, this Brattleboro gem offers ultimate comfort and self-sufficiency. See MLS Property & Listing Details & 37 images.

$449,000 $302 per sq.ft. Bridgewater VT Home »

Waterfront on River Ottauquechee River
3 Beds | 2 Baths |   Total Sq. Ft. 1489  |  Acres: 0.33
Thursday Jul 24, 2025
Description: This 1885 antique story and a half cape has been comprehensively updated during the long ownership of the sellers who made the home more energy efficient with all new windows, recent heating system, modern kitchen and bathrooms. The home creatively blends an historic floor plan defined by a traditional living room and dining room with the more casual lifestyle of today. The open concept Vermont country kitchen-dining and family room flow into a south facing sunroom overlooking the Ottauquechee River with a terraced yard providing direct access to the water. The home is midway between the resort communities of Woodstock and Killington 5 and 9 miles away. A public park and the Bridgewater Mill showcasing nationally and internationally recognized handmade furniture and pottery of Charles Shackelton and Miranda Thomas, respectively, in addition to a popular restaurant with live entertainment all within walking distance. Ideally sited offering an array of amenities at an attractive price. See MLS Property & Listing Details & 34 images.

$479,000 $282 per sq.ft. Bridgewater VT Home »

Price Change! Reduced by $21,000 down 4% on June 4th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1700  |  Acres: 0.33
Sunday May 10, 2026
Description: THE SUGAR HOUSE -- Beautifully renovated in 2007, this light-filled Vermont home is ideally located in the heart of historic Bridgewater, just 10 minutes from the charm, dining, and culture of the village of Woodstock. Offering the perfect balance of four-season recreation and classic New England character, the property is equally suited as a primary residence, weekend retreat, or investment opportunity. The home features three bedrooms, two updated bathrooms, an open-concept kitchen and living area, and fully modernized systems for easy ownership. Outside, enjoy a true Vermont lifestyle with nearby swimming holes, hiking and biking trails, horseback riding, the Bridgewater Mill, and local favorite Ramunto's Pizza all within easy reach. The VAST trail is located just behind the property, providing direct access to winter adventures and peaceful summer walks through the Green Mountains. A spacious two-car garage includes a large second-floor workshop or studio space, while the charming chicken coop offers flexibility for hobby farming, storage, or relaxed evenings outdoors. Perfectly positioned for ski enthusiasts, the home is just a short drive to Killington Resort, Pico, Okemo, and Saskadena Six, making it an exceptional base for enjoying some of Vermont's best skiing and year-round recreation. The property also benefits from a strong and established short-term rental history, offering excellent income potential in one of the region's most desirable tourism corridors. Move-in ready and conveniently located near outstanding schools, outdoor recreation, and the timeless appeal of Woodstock, The Sugar House is a rare Upper Valley opportunity. See MLS Property & Listing Details & 40 images.