22

Brattleboro, VT Houses for Sale

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  • /39

    $625,000

    • 5 Beds
    • 4 Baths
    • 3,748 Sq Ft

    58 Oak St, Brattleboro, VT 05301

    Come experience the elegance and charm of this stunning in-town retreat! Close to the town common and vibrant downtown Brattleboro—home to fine dining, galleries, quaint shops, and live music venues. Step inside the main house and be welcomed by a country kitchen featuring a large island, ideal for gatherings. The home exudes Victorian character with soaring ceilings, hardwood floors, and

    Rebecca Seymour Brattleboro Area Realty

    58 Oak St, Brattleboro, VT 05301
  • /36

    $442,500 Open Sat 10AM - 12PM

    • 4 Beds
    • 3.5 Baths
    • 2,794 Sq Ft

    87 Orchard St, Brattleboro, VT 05301

    Pleasant and comfortable! This inviting home offers four bedrooms, three and a half bathrooms, a choice of primary bedroom with ensuite bath on the first floor or on the second. Enjoy a pleasant open flow living, kitchen and dining with hard wood floors for entertaining or hosting your next book club. The first floor offers a cheerful step saver kitchen with a pantry, gas range and views to the

    Jim Bellville Bellville Realty

    87 Orchard St, Brattleboro, VT 05301
  • /32

    $425,000

    • 3 Beds
    • 1.5 Baths
    • 1,655 Sq Ft

    155 Upper Dummerston Rd, Brattleboro, VT 05301

    Great location! This 3-bedroom Colonial, built in 1920 (when houses were well-built) on Upper Dummerston Road is up the road from the Brattleboro Country Club and its golf course, cross country skiing, trails, and the West River. On a comfortable 0.75 level acres, this property is private but only 10 minutes from the center of town. Lots of windows bring in lots of light. Generous living room,

    John Hatton Berkley & Veller Greenwood Country

    155 Upper Dummerston Rd, Brattleboro, VT 05301
  • /37

    $849,000

    • 4 Beds
    • 4 Baths
    • 3,600 Sq Ft

    5 Hillwinds N, Brattleboro, VT 05301

    Elegant Post-and-Beam home in coveted Hillwinds. Tucked along a birch-lined drive, this exceptional post-and-beam home is set on 11+ acres of landscaped grounds with lawns, stone walls, gardens, and mixed woodland 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

    Robert Doyle Berkley & Veller Greenwood Country

    5 Hillwinds N, Brattleboro, VT 05301
  • /44

    $475,000

    • 4 Beds
    • 3 Baths
    • 3,314 Sq Ft

    76 Spruce St, Brattleboro, VT 05301

    Sweet! The perfect location...intown...backing up to the retreat trail system...and has a beautiful front porch and private back deck. This has been a much loved home, ready for a new generation to create their own music and harmony of life. The rooms are large, comfortable with lots of windows, real wood paneling reflecting the era, high ceilings, enough room to work from home (even an office

    Christine Lewis Brattleboro Area Realty

    76 Spruce St, Brattleboro, VT 05301
  • /58

    $568,000

    • 3 Beds
    • 2 Baths
    • 2,066 Sq Ft

    192 Western Ave, Brattleboro, VT 05301

    Timeless 1855 classic with historic charm just minutes to downtown Brattleboro. Step back in time with this beautifully preserved home, offering a rare blend of vintage character and modern comfort. Featuring three bedrooms and two bathrooms, this home is perfect for those who appreciate craftsmanship and history. Thoughtful updates complement the historic features without compromising

    Claire Renaud Berkley & Veller Greenwood Country

    192 Western Ave, Brattleboro, VT 05301
  • /30

    $579,000

    • 4 Beds
    • 2 Baths
    • 2,656 Sq Ft

    204 Meeting House Ln, Brattleboro, VT 05301

    Your Dream Home Awaits on Meetinghouse Lane! Nestled in the desirable and quiet neighborhood of Meetinghouse Lane, this contemporary home offers both privacy & charm. Surrounded by mature trees, the property feels like a peaceful retreat, while still being conveniently located. A paved driveway leads to an oversized two-car garage, connected to the house by a convenient breezeway. The expansive

    Desiree Stango Berkley & Veller Greenwood Country

    204 Meeting House Ln, Brattleboro, VT 05301
  • /60

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 3,415 Sq Ft

    23 Meeting House Ln, Brattleboro, VT 05301

    First Time on the Market – Premier Brattleboro Location!Nestled on one of the most desirable lots in one of Brattleboro’s finest neighborhoods, this well-maintained home is being offered for sale for the very first time! Custom-built by the current owner in 1970 with attention to detail, this spacious ranch offers comfort, functionality, and an impressive list of amenities.Perfect for

    Bert Inman RE/MAX Town & Country

    23 Meeting House Ln, Brattleboro, VT 05301
  • /18

    $425,000

    • 3 Beds
    • 2 Baths
    • 2,074 Sq Ft

    36 Spruce St, Brattleboro, VT 05301

    New Price! $25,000.00 price drop and a revised offering... If you saw this home before you want to take a second look! The 2nd floor is now vacant! ..and ready for owner occupancy. The basement, barn and lower building are empty and ready for all YOUR stuff. Plenty of undercover storage for boats, special vehicles or lots of other toys. A workshop? Home is just right for 2 family use or

    Christine Lewis Brattleboro Area Realty

    36 Spruce St, Brattleboro, VT 05301
  • /30

    $400,000

    • 3 Beds
    • 2 Baths
    • 1,703 Sq Ft

    1089 Marlboro Rd, Brattleboro, VT 05301

    The one you have been waiting for! This traditional New England cape with a twist checks all the boxes! Remodeled in the 90's, it has a cook's delight for a kitchen with tons of cabinets and lots of countertops for baking prep...cookies and breads are a must!. The first floor was expanded to almost double the size of the living room, adding a fireplace and a main bedroom. Again in place is easy

    Christine Lewis Brattleboro Area Realty

    1089 Marlboro Rd, Brattleboro, VT 05301
  • /19

    $84,500

    • 3 Beds
    • 1 Bath
    • 1,490 Sq Ft

    7 Nichols Dr, Guilford, VT 05301

    This two story home offers 3 bedrooms/1 bathroom with 1,490 sq. ft. of living space. The property sits on a 0.50 acre lot. The first floor has a kitchen with wooden cabinets and granite countertops, wood flooring and a carpeted living room. A dedicated laundry area is also included. The property features a barn in the backyard for storage. Exterior highlights include a covered front entry,

    Derek Greene Derek Greene

    7 Nichols Dr, Guilford, VT 05301
  • /38

    $395,000

    • 4 Beds
    • 2 Baths
    • 2,715 Sq Ft

    105 Chestnut St, Brattleboro, VT 05301

    This authentic and updated Vermont home is situated on welcoming, dead-end street surrounded by woods on two sides creating a feeling of peacefulness and connection with nature. How fortunate to live in town but also have the calming surroundings of mature plantings, opportunity to garden and de-stress in your private sanctuary. Enjoy outdoor dining on the deck, located just off the dining

    Kristen Ziter Taylor Brattleboro Area Realty

    105 Chestnut St, Brattleboro, VT 05301
  • /24

    $299,000

    • 3 Beds
    • 1 Bath
    • 912 Sq Ft

    91 Carriage Hill Rd, Brattleboro, VT 05301

    This charming split-level home offers 3 bedrooms and a full bathroom, complete with a single-bay garage in the desirable Carriage Hill neighborhood. Hardwood floors extend through the living room, hall, and bedrooms, adding warmth and character. The living room features a lovely picture window with opening side windows, perfect for letting in a refreshing breeze and natural light.The lower level

    Rebecca Seymour Brattleboro Area Realty

    91 Carriage Hill Rd, Brattleboro, VT 05301
  • /20

    $279,900

    • 4 Beds
    • 2 Baths
    • 1,733 Sq Ft

    1177 Western Ave, Brattleboro, VT 05301

    Looks can be deceiving! This home is worth more than a drive by...it offers so much...a huge lot so the solar panels are tucked away and not in your face, huge gardening possibilities and lots of parking for easy access. The large back deck overlooks the backyard giving a little view of the neighborhood. There are baths on both floors and a newer kitchen with lots of counter space and the

    Christine Lewis Brattleboro Area Realty

    1177 Western Ave, Brattleboro, VT 05301
  • /2

    $300,000

    • 4 Beds
    • 2 Baths
    • 1,808 Sq Ft

    109 Central St, Brattleboro, VT 05301

    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

    Christine Lewis Brattleboro Area Realty

    109 Central St, Brattleboro, VT 05301
  • /51

    $899,800

    • 5 Beds
    • 8 Baths
    • 7,430 Sq Ft

    925 Hinesburg Rd, Brattleboro, VT 05301

    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

    Christine Lewis Brattleboro Area Realty

    925 Hinesburg Rd, Brattleboro, VT 05301
  • /29

    $279,900

    • 3 Beds
    • 2 Baths
    • 1,183 Sq Ft

    4322 Augur Hole Rd, Brattleboro, VT 05301

    Super location! Easy access to Rt 9 and Rt 30 but tucked into nearly a level acre in a lovely country setting. You can tell the previous occupants loved their gardens and a bit of work would restore the blooms to full glory. The pool is a bonus but is waiting for some care to get up and running...The home has emerged from a fun loving schoolhouse filled with learning and joy to a cozy,

    Christine Lewis Brattleboro Area Realty

    4322 Augur Hole Rd, Brattleboro, VT 05301
  • /60

    $895,000

    • 3 Beds
    • 3 Baths
    • 2,258 Sq Ft

    266 Ursa Ridge Rd, Dummerston, VT 05301

    This home is living art, tucked away at the end of the road of lovely homes & hundreds of acres ridgetop, yet only 10 minutes from downtown Brattleboro. Built by a craftsman this home is gracious & energy efficient. Building materials have been harvested from it's 51-1/2 acre woodland. Rooms are thoughtfully designed awash with natural light. Walk up the covered, stone walkway to enter the

    Randi Ziter Brattleboro Area Realty

    266 Ursa Ridge Rd, Dummerston, VT 05301
  • /18

    $319,900 Open Sun 11AM - 1PM

    • 3 Beds
    • 1 Bath
    • 1,323 Sq Ft

    164 Chestnut St, Brattleboro, VT 05301

    Just right for new beginnings! This raised ranch affords the new home buyer a cozy place to start with a big, level yard with lots of flowering shrubs to look pretty when you drive up, and a perfect spot for ball in the back! The dead end street is a bit safer for bikes and strolls than others and creates a nice comfortable neighborhood for smiling greetings. With an eat in kitchen with

    Christine Lewis Brattleboro Area Realty

    164 Chestnut St, Brattleboro, VT 05301
  • /58

    $586,000

    • 4 Beds
    • 2 Baths
    • 3,090 Sq Ft

    301 Maple St, Brattleboro, VT 05301

    This is IT! Summer is here! The gardens are ablaze, the deck is perfect for the evening sip of something cool and there is open sky for sightings like the strawberry moon and shooting stars. Treat yourself to your own spa....the sweet spot is the oversized salt pool, surrounded by lush greenery for privacy and an apron for sunning. Add some of your own fun and you will stay at home,

    Christine Lewis Brattleboro Area Realty

    301 Maple St, Brattleboro, VT 05301
  • /60

    $1,195,000

    • 4 Beds
    • 3.5 Baths
    • 3,400 Sq Ft

    1845 Hatch School Rd, Brattleboro, VT 05301

    Welcome to our Contemporary Farmhouse with 100 private acres yet only 5 miles to Wilmington Center and 14 miles to Mount Snow Ski Resort. Harriman Reservoir is close for summer boating, water sports and picnics. Nestled in the heart of nature, the property offers numerous possibilities, including a well-appointed home, a working farm, various business opportunities and/or investment potential. As

    Richard Caplan Deerfield Valley Real Estate

    1845 Hatch School Rd, Brattleboro, VT 05301
  • /22

    $275,000

    • 5 Beds
    • 3 Baths
    • 2,209 Sq Ft

    16 Washington St, Brattleboro, VT 05301

    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

    Rebecca Seymour Brattleboro Area Realty

    16 Washington St, Brattleboro, VT 05301

Why Live in Brattleboro

Brattleboro, Vermont, is a small town of about 12,000 residents located on the southeastern edge of the state, along the Connecticut River. Known for its artsy and outdoorsy lifestyle, Brattleboro has transformed from an industrial hub to a haven for artists, musicians, and authors. The town features a variety of things to do, including hiking trails, ski slopes, and boat ramps. Downtown Brattleboro is vibrant, with Main Street lined with trendy boutiques, eateries, and art galleries. Popular dining spots include Echo with its river views, Superfresh Organic Cafe, Mocha Joe’s, and Peter Havens. For nightlife, Kipling’s Tavern offers an intimate Irish pub experience. The town also hosts cultural events like the Brattleboro Literary Festival and monthly gallery walks. Outdoor enthusiasts can enjoy Living Memorial Park, which offers athletic fields, a disc golf course, and winter sports facilities. Retreat Farm provides 500 acres of preserved land with interactive nature experiences and historic landmarks. Housing styles in Brattleboro range from historic Victorians and eclectic bungalows to spacious farmhouses known as New Englanders. The town is served by the Windham Southeast Supervisory Union, with schools receiving mid-range ratings. Commuters benefit from Interstate 91, U.S. Route 5, and State Route 9, with Bradley International Airport about 80 miles away and Boston Logan International Airport approximately 110 miles southeast. Public transportation includes Amtrak Vermonter service and the free MOOver bus shuttle.

Home Trends in Brattleboro, VT

Housing Trends

Median Sale Price
$335,500
Median Single Family Sale Price
$356,000
Median Townhouse Sale Price
$235,000
Median 2 Bedroom Sale Price
$212,150
Median 1 Bedroom Sale Price
$150,000
Average Price Per Sq Ft
$222
Number of Homes for Sale
23
Last 12 months Home Sales
88
Months of Supply
3.10
Median List Price
$339,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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