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Brattleboro, VT Homes for Sale

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  • 156 Sherwood Cir, Brattleboro, VT 05301
    156 Sherwood Cir, Brattleboro, VT 05301
    156 Sherwood Cir, Brattleboro, VT 05301
    /44

    $375,000 Open Sun 2PM - 3:30PM

    • 4 Beds
    • 2.5 Baths
    • 2,132 Sq Ft

    156 Sherwood Cir, Brattleboro, VT 05301

    YOU CAN GET THERE FROM HERE! NEW ENGLAND CHARM AND FLEXIBLE SPACES...YOUR LUSH RETREAT AWAITS! A short drive to the cultural and foodie hub of southeastern Vermont, this slice of heaven is where your dreams take root. Follow a scenic road to a vibrant green lot where a terraced rock wall dotted with ferns and hostas signals your arrival. A large covered porch invites you to pull up a chair,

    Fine Homes Group International Keller Williams Realty-Metropolitan

    156 Sherwood Cir, Brattleboro, VT 05301
  • 672 E Orchard St, West Brattleboro, VT 05301
    672 E Orchard St, West Brattleboro, VT 05301
    672 E Orchard St, West Brattleboro, VT 05301
    /26

    $550,000

    • 3 Beds
    • 3 Baths
    • 3,148 Sq Ft

    672 E Orchard St, West Brattleboro, VT 05301

    You can't beat this location, overlooking the Brattleboro Country Club golf course. This home was built circa 1919, and has many cool vintage features such as retro curved metal kitchen cabinets and baths. Generous rooms include a large living room with two field-stone fireplaces, a spacious family room. This is a 3 bedroom house with 3 full bathrooms, but it's really about how you configure

    John Hatton Berkley & Veller Greenwood Country

    672 E Orchard St, West Brattleboro, VT 05301
  • 49 Tyler St, Brattleboro, VT 05301
    49 Tyler St, Brattleboro, VT 05301
    49 Tyler St, Brattleboro, VT 05301
    /60

    $729,000

    • 3 Beds
    • 2 Baths
    • 2,731 Sq Ft

    49 Tyler St, Brattleboro, VT 05301

    Rare opportunity to own this iconic Queen-Anne Victorian in Brattleboro’s coveted Tyler Street neighborhood. A remarkable and extremely rare blend of country and in-town living. Extraordinary and stunning views of the Connecticut River & Mount Wantastiquet. Lovingly cared for by the same owner for the past 29 yrs. This home sits proudly on the expansive 0.85-acre corner lot, in the core of

    Dan Normandeau Berkley & Veller Greenwood Country

    49 Tyler St, Brattleboro, VT 05301
  • 660 Bonnyvale Rd, Brattleboro, VT 05301
    660 Bonnyvale Rd, Brattleboro, VT 05301
    660 Bonnyvale Rd, Brattleboro, VT 05301
    /38

    $465,000

    • 3 Beds
    • 1.5 Baths
    • 1,560 Sq Ft

    660 Bonnyvale Rd, Brattleboro, VT 05301

    Tucked away on a peaceful 4.3-acre lot surrounded by mature trees, this “wow—worthy” 960 sq ft modern “glass house” (with additional 600+ sq ft of lower level living) on Bonnyvale Road, offers a stylish and serene retreat. Exquisitely designed, it blends indoor ease and simplicity with an outstanding natural setting. The stand-out home features an open-concept layout filled with natural light

    Kate Barry EXP Realty

    660 Bonnyvale Rd, Brattleboro, VT 05301
  • 301 Maple St, Brattleboro, VT 05301
    301 Maple St, Brattleboro, VT 05301
    301 Maple St, Brattleboro, VT 05301
    /58

    $650,000

    • 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
  • 1142 Western Ave, Brattleboro, VT 05301
    1142 Western Ave, Brattleboro, VT 05301
    1142 Western Ave, Brattleboro, VT 05301
    /26

    $450,000

    • 3 Beds
    • 1.5 Baths
    • 2,262 Sq Ft

    1142 Western Ave, Brattleboro, VT 05301

    You choose! Such a versatile property...invest in 2 rentals...live in either unit and rent the other...maybe develop the barn into another unit, home business, workshop..(check with Zoning). Just short of an acre (.86) the land is the big, big seller....the huge, mostly level back yard is already lush with flourishing fruit trees and blueberry bushes. There is a garage/gardening shed for your

    Christine Lewis Brattleboro Area Realty

    1142 Western Ave, Brattleboro, VT 05301
  • 36 Spruce St, Brattleboro, VT 05301
    36 Spruce St, Brattleboro, VT 05301
    36 Spruce St, Brattleboro, VT 05301
    /13

    $450,000

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

    36 Spruce St, Brattleboro, VT 05301

    You choose! This amazing property can be used as one of the grand ladies of the neighborhood...just open a door or two and repurpose the kitchen...what a nice laundry room it would make...or use as is with 2 flats, live in 1 and have a bit of income from the other...What else, you might ask! There is a rear section of the house ready to be reclaimed, and a barn attached that could also be built

    Christine Lewis Brattleboro Area Realty

    36 Spruce St, Brattleboro, VT 05301
  • 15 Lynwood Dr, Brattleboro, VT 05301
    15 Lynwood Dr, Brattleboro, VT 05301
    15 Lynwood Dr, Brattleboro, VT 05301
    /18

    $176,500

    • 2 Beds
    • 1 Bath
    • 888 Sq Ft

    15 Lynwood Dr, Brattleboro, VT 05301

    This is absolutely NOT your ordinary Mobile Home! The original steel frame is the only remaining component of the mobile home. Completely rebuilt from the floor up with wood framing, windows, doors and insulation. This fully fenced leased lot has two sheds, a 1 car garage building with tons of storage and a workshop building with its own mini-split for heat and AC. The tastefully renovated

    Chris Long BHG Masiello Brattleboro

    15 Lynwood Dr, Brattleboro, VT 05301
  • 85 Crosby St, Brattleboro, VT 05301
    85 Crosby St, Brattleboro, VT 05301
    85 Crosby St, Brattleboro, VT 05301
    /19

    $299,000

    • 3 Beds
    • 1 Bath
    • 1,500 Sq Ft

    85 Crosby St, Brattleboro, VT 05301

    Charming 1950s Gem! Step into timeless warmth and character with this delightful 3-bedroom, 1-bath home. This lovingly cared for home features beautiful rock maple hardwood floors, solid wood doors, and rich original woodwork that speak to its enduring craftsmanship. Recent updates blend vintage charm with modern comfort, including fresh interior and exterior paint, standing seam metal roof,

    Karen Hoppe Berkley & Veller Greenwood Country

    85 Crosby St, Brattleboro, VT 05301
  • 138 Cedar St, Brattleboro, VT 05301
    138 Cedar St, Brattleboro, VT 05301
    138 Cedar St, Brattleboro, VT 05301
    /18

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,174 Sq Ft

    138 Cedar St, Brattleboro, VT 05301

    Welcome to this adorable 3-bedroom, 1-bath ranch-style home nestled in one of Brattleboro's most sought-after neighborhoods! Built in 1956, this lovingly cared for gem perfectly blends classic character with modern comfort. Many recent upgrades including CertainTeed Monogram vinyl siding and trim, freshly painted interior walls and so much more. The kitchen features a sleek Whirlpool glass top

    Claire Renaud Berkley & Veller Greenwood Country

    138 Cedar St, Brattleboro, VT 05301
  • 0 E Orchard St Unit 5047716, Brattleboro, VT 05301
    0 E Orchard St Unit 5047716, Brattleboro, VT 05301
    0 E Orchard St Unit 5047716, Brattleboro, VT 05301
    /9

    $80,250

    • Land
    • 3.10 Acres
    • $25,887 per Acre

    0 E Orchard St Unit 5047716, Brattleboro, VT 05301

    A rare opportunity to purchase a lot in a highly desirable Brattleboro neighborhood. This 3+ acre wooded parcel features a mature pine forest with additional hardwoods intermixed, stonewalls and even a small stream. It's the location that makes this property unique. Just up the road from the Brattleboro Country Club on a quiet street that gives quick access to all that Brattleboro and the

    Bill Hickok Berkley & Veller Greenwood Country

    0 E Orchard St Unit 5047716, Brattleboro, VT 05301
  • 39 Brookside Dr Unit 7, Brattleboro, VT 05301
    39 Brookside Dr Unit 7, Brattleboro, VT 05301
    39 Brookside Dr Unit 7, Brattleboro, VT 05301
    /5

    $100,000

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft

    39 Brookside Dr Unit 7, Brattleboro, VT 05301

    Ready for a redo, this home is priced right for anyone who is handy with freshening, light carpentry (flooring) and other minor skills. Worth the effort to find an affordable option to renting or living with Mom! 48 hour a must for notice. This condo is located in a prime location with quick, easy access to I91 and a stones throw to the Whetstone Brook, Farmers Market and Living Memorial Park.

    Christine Lewis Brattleboro Area Realty

    39 Brookside Dr Unit 7, Brattleboro, VT 05301
  • 1082 W River Rd, Brattleboro, VT 05301
    1082 W River Rd, Brattleboro, VT 05301
    1082 W River Rd, Brattleboro, VT 05301
    /47

    $299,000

    • 3 Beds
    • 1 Bath
    • 1,222 Sq Ft

    1082 W River Rd, Brattleboro, VT 05301

    Welcome to 1082 West River Road — a peaceful, well-located gem just minutes from downtown Brattleboro. This charming home offers the perfect blend of convenience, outdoor space, and natural beauty. Set on a spacious lot with a large, open yard, there's room to garden, gather, or simply relax and enjoy the Vermont seasons. The private river access makes it easy to enjoy kayaking, swimming, or

    Kate Barry EXP Realty

    1082 W River Rd, Brattleboro, VT 05301
  • 925 Hinesburg Rd, Brattleboro, VT 05301
    925 Hinesburg Rd, Brattleboro, VT 05301
    925 Hinesburg Rd, Brattleboro, VT 05301
    /51

    $949,000

    • 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
  • 4322 Augur Hole Rd, Brattleboro, VT 05301
    4322 Augur Hole Rd, Brattleboro, VT 05301
    4322 Augur Hole Rd, Brattleboro, VT 05301
    /24

    $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
  • 104 Juniper Ridge Rd, Brattleboro, VT 05301
    104 Juniper Ridge Rd, Brattleboro, VT 05301
    104 Juniper Ridge Rd, Brattleboro, VT 05301
    /58

    $859,000

    • 3 Beds
    • 3.5 Baths
    • 3,212 Sq Ft

    104 Juniper Ridge Rd, Brattleboro, VT 05301

    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

    Kristen Ziter Taylor Brattleboro Area Realty

    104 Juniper Ridge Rd, Brattleboro, VT 05301
  • 266 Ursa Ridge Rd, Dummerston, VT 05301
    266 Ursa Ridge Rd, Dummerston, VT 05301
    266 Ursa Ridge Rd, Dummerston, VT 05301
    /60

    $995,000

    • 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
  • 164 Chestnut St, Brattleboro, VT 05301
    164 Chestnut St, Brattleboro, VT 05301
    164 Chestnut St, Brattleboro, VT 05301
    /18

    $319,900

    • 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
  • 49 Hampshire Cir, Brattleboro, VT 05301
    49 Hampshire Cir, Brattleboro, VT 05301
    49 Hampshire Cir, Brattleboro, VT 05301
    /34

    $334,500

    • 3 Beds
    • 1.5 Baths
    • 1,848 Sq Ft

    49 Hampshire Cir, Brattleboro, VT 05301

    Cute home at the end of the cul-de-sac. Large front deck with a slider that leads into a newly refinished kitchen, dining area and living room. A half bath with laundry complete the first floor. Two bedrooms upstairs with a full bath. First floor has a door that leads out back to another large deck. The third bedroom and family room in the walkout basement. Open house Saturday 6/21/25 from

    Darlene Conca Keller Williams Realty Metro-Keene

    49 Hampshire Cir, Brattleboro, VT 05301
  • 69-71 Elliot St, Brattleboro, VT 05301
    69-71 Elliot St, Brattleboro, VT 05301
    69-71 Elliot St, Brattleboro, VT 05301
    /23

    $1,150,000

    • 6,442 Sq Ft

    69-71 Elliot St, Brattleboro, VT 05301

    Prime commercial opportunity in the heart of downtown Brattleboro. This mixed-use property features seven residential apartments on the upper levels and five ground-floor commercial units. Two retail spaces have direct frontage on Elliot Street, offering strong visibility, while three others open onto the Harmony Lot pedestrian area, a centrally located public parking and business zone. The

    Erica Reynolds Southern Vermont Realty Group

    69-71 Elliot St, Brattleboro, VT 05301
  • 316 Putney Rd, Brattleboro, VT 05301
    316 Putney Rd, Brattleboro, VT 05301
    316 Putney Rd, Brattleboro, VT 05301
    /28

    $225,000

    • 3 Beds
    • 1.5 Baths
    • 1,531 Sq Ft

    316 Putney Rd, Brattleboro, VT 05301

    Convenient Location & Low Maintenance Living! Enjoy easy access to shopping, public transportation and waterfront with scenic trails. The backyard is just the right size for enjoying nature and a little fresh air. This charming home combines classic character with practical updates featuring a standing seam roof, vinyl windows and aluminum siding. Inside, the home radiates its original charm

    Kerry Mulverhill Brattleboro Area Realty

    316 Putney Rd, Brattleboro, VT 05301
  • 176 High St, Brattleboro, VT 05301
    176 High St, Brattleboro, VT 05301
    176 High St, Brattleboro, VT 05301
    /16

    $488,875

    • 5 Beds
    • 4 Baths
    • 3,064 Sq Ft

    176 High St, Brattleboro, VT 05301

    Unique opportunity to live very comfortably in the more than 1400 sq ft 1st floor apartment with private laundry, private covered porch and your own deck. The apartment has 2 plus bedrooms and 2 full bathrooms, eat in kitchen, dining room and living room. invest in your own home and have revenue from 2 apartments to help with costs. Apartment #2, on the 2nd floor, is a 1-2 bedroom unit which has

    Susan Bellville Bellville Realty

    176 High St, Brattleboro, VT 05301
  • 62 Lawton Dr, Brattleboro, VT 05301
    62 Lawton Dr, Brattleboro, VT 05301
    62 Lawton Dr, Brattleboro, VT 05301
    /22

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft

    62 Lawton Dr, Brattleboro, VT 05301

    Everything deserves a second chance, and this home found the right owner to love and recreate it in a stunning new life. Anyone who has looked at this home in the past few years, has to come back to see the shine....the fresh new look....the simplicity of move right in. Not only is this home refreshed stem to stern, it has new windows, siding, shingles, kitchen, bath.....and on and on! Tuck

    Christine Lewis Brattleboro Area Realty

    62 Lawton Dr, Brattleboro, VT 05301
  • 29 Canal St, Brattleboro, VT 05301
    29 Canal St, Brattleboro, VT 05301
    29 Canal St, Brattleboro, VT 05301
    /26

    $725,000

    • 18 Beds
    • 8 Baths
    • 4,932 Sq Ft

    29 Canal St, Brattleboro, VT 05301

    High cash flow 100% occupied 8 unit located in downtown Brattleboro. This property was recently renovated and is being listed at a 11% cap and an annual Net Operating Income estimated at north of ~$80K (12% cap without management fees). The property features an attractive mix of unit types and sizes including 4x rarely available oversized 3br, 2x2br and 2x1brA new owner can step into to

    Michael Gilman 3GEN Real Estate Inc

    29 Canal St, Brattleboro, VT 05301
  • 22 Chestnut St, Brattleboro, VT 05301
    22 Chestnut St, Brattleboro, VT 05301
    22 Chestnut St, Brattleboro, VT 05301
    /51

    $544,400

    • 6 Beds
    • 4 Baths
    • 3,000 Sq Ft

    22 Chestnut St, Brattleboro, VT 05301

    4 condo units being sold together as a great residential package investment opportunity! Rent them, live in one and/or sell them off individually. This offering includes 4 of 5 units in a charming condo development just minutes from downtown, the hospital, shopping, and I-91. Unit 5 has been sold. The property features a large shared yard, off-street parking, and strong rental potential. The

    Erica Reynolds Southern Vermont Realty Group

    22 Chestnut St, Brattleboro, VT 05301
  • 412 Western Ave, Brattleboro, VT 05301
    412 Western Ave, Brattleboro, VT 05301
    412 Western Ave, Brattleboro, VT 05301
    /5

    $315,000

    • 3 Beds
    • 2.5 Baths
    • 2,014 Sq Ft

    412 Western Ave, Brattleboro, VT 05301

    The cutest house on the block! Only 1 house from the famous deli for eats, right near the entrance to I 91, both north and south for travel or work and 2 minutes away from Memorial Park with all it offers....skating, ball games, pools, sliding, skiing. Plus it has a great back yard, 2 levels of decks and a front porch to add to the package. This 1860's Mansard is so sweet, filled with character

    Christine Lewis Brattleboro Area Realty

    412 Western Ave, Brattleboro, VT 05301
  • 36 Spruce St, Brattleboro, VT 05301
    36 Spruce St, Brattleboro, VT 05301
    36 Spruce St, Brattleboro, VT 05301
    /13

    $450,000

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

    36 Spruce St, Brattleboro, VT 05301

    Perfect investment. Choose which flat you want to live in and have a bit of income, OR...consider this a long term investment! Such a special location and huge yard. Consider developing more apartments in the back of the house, and rent out the 40 x 40 steel frame building...OR develop into your dream workshop and let the rentals help pay for your fun. Rentals are below market for the

    Christine Lewis Brattleboro Area Realty

    36 Spruce St, Brattleboro, VT 05301
  • 1845 Hatch School Rd, Brattleboro, VT 05301
    1845 Hatch School Rd, Brattleboro, VT 05301
    1845 Hatch School Rd, Brattleboro, VT 05301
    /59

    $1,338,000

    • 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
  • 16 Washington St, Brattleboro, VT 05301
    16 Washington St, Brattleboro, VT 05301
    16 Washington St, Brattleboro, VT 05301
    /22

    $275,000

    • 4 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
  • 16 Washington St, Brattleboro, VT 05301
    16 Washington St, Brattleboro, VT 05301
    16 Washington St, 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
  • 1324 Middle Rd, Brattleboro, VT 05301
    1324 Middle Rd, Brattleboro, VT 05301
    1324 Middle Rd, Brattleboro, VT 05301
    /46

    $2,490,000

    • 7 Beds
    • 7.5 Baths
    • 8,718 Sq Ft

    1324 Middle Rd, Brattleboro, VT 05301

    Truly a rare and remarkable property. This custom home was lovingly designed and constructed in 2005 with a clear vision for bringing the Vermont scenery in, while maintaining the rustic charm befitting a country estate. The main house features gorgeous exposed timber frame construction throughout, natural wood flooring, paneling, and trim, extensive artisan stonework inside and out, including 3

    Adam Palmiter Berkley & Veller Greenwood/Dover

    1324 Middle Rd, Brattleboro, VT 05301
  • 46-48 Lexington Ave, Brattleboro, VT 05301
    46-48 Lexington Ave, Brattleboro, VT 05301
    46-48 Lexington Ave, Brattleboro, VT 05301
    /5

    $89,000

    • Land
    • 0.21 Acre
    • $423,810 per Acre

    46-48 Lexington Ave, Brattleboro, VT 05301

    This open, level, in-town building lot is a blank slate awaiting its next chapter. Tucked away in a small neighborhood on a dead-end street, this location offers easy accessibility to shopping, restaurants, public transportation and the interstate. Utilities are readily available, including existing hookups for town water and sewer. A unique opportunity!

    Stephanie Wilde Brattleboro Area Realty

    46-48 Lexington Ave, Brattleboro, VT 05301
  • 50 Terrace St, Brattleboro, VT 05301
    50 Terrace St, Brattleboro, VT 05301
    50 Terrace St, Brattleboro, VT 05301
    /5

    $680,000

    • Studio
    • 5,540 Sq Ft

    50 Terrace St, Brattleboro, VT 05301

    SUPERB OPPORTUNITY to acquire one of Brattleboro’s nicest multi-family, investment properties!! Situated in one of THE BEST neighborhoods in Brattleboro, Vermont, this sweet, money-maker offers 7 units on a quiet street that is SOOO close to downtown Brattleboro. What every investor dreams of!!! Location, quality condition and build, spacious unit size, superb level, off-street parking, and

    Dan Normandeau Berkley & Veller Greenwood Country

    50 Terrace St, Brattleboro, VT 05301
  • 24 Summit Cir, West Brattleboro, VT 05301
    24 Summit Cir, West Brattleboro, VT 05301
    /2

    $90,000

    • Land
    • 1.97 Acres
    • $45,685 per Acre

    24 Summit Cir, West Brattleboro, VT 05301

    Gorgeous building lot nestled into a prime development on a wooded hillside in Southern Vermont. The 1.97 wooded lot is minutes to downtown Brattleboro, yet private and rural!

    Claire Renaud Berkley & Veller Greenwood Country

    24 Summit Cir, West Brattleboro, VT 05301
  • 203 Fairview St, Brattleboro, VT 05301
    203 Fairview St, Brattleboro, VT 05301
    203 Fairview St, Brattleboro, VT 05301
    /10

    $59,900

    • Land
    • 0.25 Acre
    • $239,600 per Acre

    203 Fairview St, Brattleboro, VT 05301

    In-town lots are few and far between these days but are such a great option! Design your own low inpact, energy efficient home, your dream home! This is your spot! This neighborhood is friendly and convenient to schools, Memorial Park, shopping, hospitals and just minutes to 91. The .25 acre lot is cleared and ready to go with easy access to town water and sewer. House site is set back from the

    Rebecca Seymour Brattleboro Area Realty

    203 Fairview St, Brattleboro, VT 05301
  • 211 High St, Brattleboro, VT 05301
    211 High St, Brattleboro, VT 05301
    211 High St, Brattleboro, VT 05301
    /15

    $100,000

    • 2,090 Sq Ft

    211 High St, Brattleboro, VT 05301

    Here's a great opportunity! Formerly a 2 unit multi-family, this is currently a shell ready for your finishing! This property will need everything ... heating, electrical, plumbing, exterior work and full interior finishing. Very convenient to downtown, some off street parking but nicely sited above the road. Please do NOT park in the driveway.

    A.J. Bellville Bellville Realty

    211 High St, Brattleboro, VT 05301
  • 25 Cottage St, Brattleboro, VT 05301
    25 Cottage St, Brattleboro, VT 05301
    25 Cottage St, Brattleboro, VT 05301
    /5

    $380,000

    • 6 Beds
    • 4 Baths
    • 3,264 Sq Ft

    25 Cottage St, Brattleboro, VT 05301

    Sweet neighborhood. This would be a great location for an owner to live in one unit and rent the other 3. Lots of character! Great investment possibility. Close to Hospital, nursing homes, shopping, interstate for travel. Plenty of off street parking

    Christine Lewis Brattleboro Area Realty

    25 Cottage St, Brattleboro, VT 05301
  • 000 Fort Dummer Heights Unit 1 and 2, Brattleboro, VT 05301
    000 Fort Dummer Heights Unit 1 and 2, Brattleboro, VT 05301
    000 Fort Dummer Heights Unit 1 and 2, Brattleboro, VT 05301
    /9

    $250,000

    • Land
    • 3.79 Acres
    • $65,963 per Acre

    000 Fort Dummer Heights Unit 1 and 2, Brattleboro, VT 05301

    Easy to build!!! The land is open, so no fuss with a lot of prep. Beautiful high meadow, in a nice little neighborhood tucked up against the state park, what more could you want? This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor cooperation.

    Christine Lewis Brattleboro Area Realty

    000 Fort Dummer Heights Unit 1 and 2, Brattleboro, VT 05301
  • 00 Fort Dummer Heights Unit 2, Brattleboro, VT 05301
    00 Fort Dummer Heights Unit 2, Brattleboro, VT 05301
    /2

    $150,000

    • Land
    • 2.05 Acres
    • $73,171 per Acre

    00 Fort Dummer Heights Unit 2, Brattleboro, VT 05301

    Beautiful high meadow, in a nice little neighborhood tucked up against the state park, what more could you want? Easy to build!!! The land is open, so no fuss with a lot of prep. This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor cooperation.

    Christine Lewis Brattleboro Area Realty

    00 Fort Dummer Heights Unit 2, Brattleboro, VT 05301
  • 0 Fort Dummer Heights Unit 1 4934976, Brattleboro, VT 05301
    0 Fort Dummer Heights Unit 1 4934976, Brattleboro, VT 05301
    0 Fort Dummer Heights Unit 1 4934976, Brattleboro, VT 05301
    /3

    $125,000

    • Land
    • 1.75 Acres
    • $71,429 per Acre

    0 Fort Dummer Heights Unit 1 4934976, Brattleboro, VT 05301

    Manicured into a beautiful high meadow, in a nice little neighborhood....sunny with views, what more could you want? Easy to build!!! The land is open, so no fuss with a lot of prep. This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor

    Christine Lewis Brattleboro Area Realty

    0 Fort Dummer Heights Unit 1 4934976, Brattleboro, VT 05301

Showing Results 1 - 40, Page 1 of 2

Vermont Brattleboro

Real Estate & Homes for Sale in Brattleboro, VT

Why Live in Brattleboro

On the southeastern edge of Vermont, Brattleboro started as a trading gateway along the Connecticut River before developing into a bookbinding and pipe organ manufacturing town in the 1800s. Today, the small town of about 12,000 residents offers both an artsy and outdoorsy way of life. “We’re a service town for the more rural areas around our outskirts, and city folk have found us, so we’ve become more desirable,” says Christine Lewis, a local broker at Brattleboro Area Realty. “Our landscape is lumpy; we have hills and valleys that give us nice views and waterways. The town is well-laid out with nature preserves all around us, so we also attract outdoorsy and active people.” In addition to hiking trails and green spaces, this Windham County town offers ski slopes and boat ramps. Brattleboro’s industry seamlessly transformed from industrial to creative, as more artists, musicians and authors moved to the area. Art galleries and music venues neighbor Main Street’s trendy boutiques and eateries. “We are considered kind of a hippie town. During the war draft years, a lot of young people with a conscience came to Windham College, which was a liberal arts college," Lewis says,
Learn more about living in Brattleboro

Frequently Asked Questions

What is the average home price in Brattleboro, VT?
Homes for sale in Brattleboro, VT have an average home price of $393,962.
Are home prices dropping in Brattleboro?
Yes, home prices in Brattleboro are down 11% in the last 12 months.
How many homes have sold over the last 12 months in Brattleboro, VT?
74 homes have sold in Brattleboro, VT over the last 12 months.
What are the most popular zip codes in Brattleboro, VT?
The most popular zip codes in Brattleboro, VT include 05356, 05301, 03431, 05363 and 01301.
How much do you need to make to afford a house in Brattleboro?
The median home price in Brattleboro is $325,000. If you put a 20% down payment of $65,000 and had a 30-year fixed mortgage with an interest rate of 6.77%, your estimated principal and interest payment would be $1,690 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $72K a year to afford the median home price in Brattleboro.
How are the schools in Brattleboro, VT?
Brattleboro, VT has highly rated public and private schools. Some of the best schools in Brattleboro based on Niche Grades are St. Michael Catholic School, Brattleboro Union High School and Dummerston School. Browse all the schools in Brattleboro, VT to learn more.

Home Trends in Brattleboro, VT

On average, homes in Brattleboro, VT sell after 54 days on the market compared to the national average of 50 days. The median sale price for homes in Brattleboro, VT over the last 12 months is $323,640, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$323,640
Median Single Family Sale Price
$335,000
Median Townhouse Sale Price
$225,000
Median 2 Bedroom Sale Price
$231,150
Median 1 Bedroom Sale Price
$135,000
Average Price Per Sq Ft
$221
Number of Homes for Sale
20
Last 12 months Home Sales
74
Months of Supply
3.20
Median List Price
$325,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-3%
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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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