Brattleboro, VT Homes

• 

  

  

  /27

  Est $408,180 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,994 Sq Ft

  22 Howard St, Brattleboro, VT 05301

  22 Howard St, Brattleboro, VT 05301
• 

  

  

  /25

  $269,000 Pending

  • 5 Beds
  • 4 Baths
  • 2,376 Sq Ft

  50 Grove St, Brattleboro, VT 05301

  New to the market, this well-maintained 3-unit property is a fantastic opportunity for both investors and owner-occupants. Located just minutes from downtown, it offers convenience, value, and flexibility. One unit is currently on a month to month and move-in ready, making it ideal for someone looking to live on-site or set their own rental terms. The other two units are occupied by long-term,

  Kate Barry EXP Realty

  50 Grove St, Brattleboro, VT 05301
• 

  

  

  /33

  $386,250 Sold Jun 12, 2025

  • 1,617 Sq Ft
  • $239/SF
  • 49 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1880

  33 Frost Place, Brattleboro, VT 05301

  Whether you're seeking a smart investment or a beautifully appointed primary residence, this exceptional offering in the heart of Brattleboro, VT, is not to be missed. Fully renovated by the current owners, this charming home offers far more than it's modest exterior suggests.Step onto the inviting screened porch — the perfect spot to unwind during warmer months or transition comfortably from the

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  33 Frost Place, Brattleboro, VT 05301
• 

  

  

  /40

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,628 Sq Ft

  43 Williston St, Brattleboro, VT 05301

  43 Williston St, Brattleboro, VT 05301
• 

  

  

  /42

  $849,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,150 Sq Ft

  65 Hillwinds N, Brattleboro, VT 05301

  This beautiful Colonial blends timeless design with contemporary enhancements. Set on over 2 acres of landscaped grounds, the property offers a country setting just minutes from Brattleboro. Inside, the floor plan has been expanded with large, light-filled rooms & custom features. The gourmet kitchen is a showstopper, w/Quartz counters, custom cabinetry, top-tier appliances, glass tile backsplash

  Robert Doyle Berkley & Veller Greenwood Country

  65 Hillwinds N, Brattleboro, VT 05301
• 

  

  /15

  $350,000 Sold Jun 12, 2025

  • 1,272 Sq Ft
  • $275/SF
  • 7 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1872

  187 Maple St, Brattleboro, VT 05301

  This light, airy, two-story, 3-bedroom house was built during the Civil War, around 1864. On .35 acres, there are planted gardens, lawn, and a large, sunny area that can be a good-sized vegetable garden. The house has a large kitchen area w/ a small wood-burning stove, a living room, dining room, a ground-floor WC and study. A screened three-season porch has been added to the house and is a

  John Hatton Berkley & Veller Greenwood Country

  187 Maple St, Brattleboro, VT 05301
• 

  

  /40

  Est $676,418 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,137 Sq Ft

  43 Tyler St, Brattleboro, VT 05301

  43 Tyler St, Brattleboro, VT 05301
• 

  

  /33

  $235,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 2,112 Sq Ft

  116 Morningside Commons, Brattleboro, VT 05301

  Yes! A coveted first floor single level unit! And not only that but an end unit, sweetly tucked away for privacy! Just follow the tree and flower lined path right to your door!2 bedrooms, one ensuite, with an additional bedroom, bath, large eat in kitchen, living room, and a stackable washer/dryer, all on the first floor! There are only a few condos here that have finished basement space and

  Rebecca Seymour Brattleboro Area Realty

  116 Morningside Commons, Brattleboro, VT 05301
• 

  

  /22

  $93,999 Sold Jun 10, 2025

  • 880 Sq Ft
  • $107/SF
  • 90 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2024

  8 Reservoir Rd, Brattleboro, VT 05301

  Welcome to 8 Reservoir Rd, Brattleboro, VT 05301, where modern comfort meets affordability in Deepwood MHP Park! This brand-new Dias model manufactured home offers 3 bedrooms, 2 bathrooms, and 869 sq. ft. (14 x 66 ft.) of thoughtfully designed living space.Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  8 Reservoir Rd, Brattleboro, VT 05301
• 

  

  /12

  Est $312,746 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,542 Sq Ft

  35 Upper Forest St, Brattleboro, VT 05301

  35 Upper Forest St, Brattleboro, VT 05301
• 

  

  /38

  $395,000 Under Contract

  • 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

  $325,000 Sold Jun 09, 2025

  • 1,464 Sq Ft
  • $222/SF
  • 7 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1990

  110 Arbor Hill Commons Unit 25, Brattleboro, VT 05301

  Sunlight pours into this beautifully maintained home! If you're looking for a low-maintenance lifestyle—no snow shoveling, no exterior upkeep—this is the one for you. Drive directly into your attached garage, which offers extra storage, and enter through a spacious mudroom with even more room to stay organized. The main level features an open-concept kitchen, dining, and living area—perfect for

  Thomas Dahlin Berkley & Veller Greenwood Country

  110 Arbor Hill Commons Unit 25, Brattleboro, VT 05301
• 

  

  /14

  Est $304,926 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,368 Sq Ft

  7 Union St, Brattleboro, VT 05301

  7 Union St, Brattleboro, VT 05301
• 

  

  /14

  $249,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft

  70 Arbor Hill Commons Unit 15, Brattleboro, VT 05301

  Beautifully elegant light filled condo in Bluebell Building at Arbor Hill. An abundance of windows throughout creates a magical light filled environment that includes hardwood flooring, a Great Room providing space for Living, Dining and Kitchen, 2 spacious Bedrooms, 2 Full Baths, Entry w/ double closet and Laundry/Pantry. The Primary Bedroom has an en suite Bath, mini split and a large walk-in

  Robert Doyle Berkley & Veller Greenwood Country

  70 Arbor Hill Commons Unit 15, Brattleboro, VT 05301
• 

  

  /15

  $160,000 Sold Jun 09, 2025

  • 840 Sq Ft
  • $190/SF
  • 276 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 2003

  12 Culbertson Dr, West Brattleboro, VT 05301

  PRETTY IN PINK! The famous PINK house is back on the market with a huge price reduction and looking for just the right buyer...can it be an investor who takes it to a new level.....it is a sweet rental property... or an affordable great place to park the x generation until they find their way? If you saw it before, come back and check it out...great new price, stackable washer and dryer...and a

  Christine Lewis Brattleboro Area Realty

  12 Culbertson Dr, West Brattleboro, VT 05301
• 

  

  /38

  Est $286,387 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 916 Sq Ft

  92 Western Ave, Brattleboro, VT 05301

  92 Western Ave, Brattleboro, VT 05301
• 

  

  /23

  $249,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  45 Blakeslee St, Brattleboro, VT 05301

  Charming Sun-Filled Cape on Corner Lot.This sweet and practical 2-bedroom, 2-bathroom Cape offers timeless appeal and everyday comfort on a sunny corner lot. Built in 1942, the home retains its original charm with 3-over-1 windows, built-ins throughout, and even a vintage ironing board cabinet. Inside, enjoy wood floors, a spacious eat-in kitchen with generous counter space, and a bright

  Liz LaVorgna Berkley & Veller Greenwood Country

  45 Blakeslee St, Brattleboro, VT 05301
• 

  

  /22

  $67,000 Sold Jun 06, 2025

  • 1,224 Sq Ft
  • $55/SF
  • 14 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1978

  89 Glen St, West Brattleboro, VT 05301

  This single wide has so many added benefits! You can heat entirely with wood should you choose, there's an entryway and a huge heated mudroom, with direct access to the expansive back yard. The corner lot overlooks neighboring grassy fields for additional privacy. This yard has raised beds and over 200 bulbs planted!Being sold with a solar generator that powers the owners' home office.Contingent

  Victoria Woods Brattleboro Area Realty

  89 Glen St, West Brattleboro, VT 05301
• 

  

  /31

  Est $248,401 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 752 Sq Ft

  95 Williams St, Brattleboro, VT 05301

  95 Williams St, Brattleboro, VT 05301
• 

  

  /34

  $299,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,025 Sq Ft

  35 Hillcrest Terrace, Brattleboro, VT 05301

  Open House August 1, 5:30-7:00 and August 2, 10-11:30. Welcome to 35 Hillcrest Terrace, a well-loved home owned by the same family for over 20 years, perfectly situated in one of Brattleboro’s most convenient neighborhoods. Just moments from Memorial Park, this charming property offers easy access to recreation, walking trails, and town amenities while providing a peaceful, residential

  Morriah Adams BHG Masiello Brattleboro

  35 Hillcrest Terrace, Brattleboro, VT 05301
• 

  

  /35

  $341,000 Sold Jun 03, 2025

  • 1,631 Sq Ft
  • $209/SF
  • 62 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1945

  70 Greenleaf St, Brattleboro, VT 05301

  Welcome Home! This move-in-ready gem is a delight, full of character and charm with modern conveniences. As you step inside, you'll find a home bathed in natural sunlight, creating a warm and inviting atmosphere. The open kitchen and dining area are perfect for entertaining, and the new sliding door opens onto the large back deck, where you can enjoy the spacious, level yard—ideal for gardening

  Kerry Mulverhill

  70 Greenleaf St, Brattleboro, VT 05301
• 

  

  /27

  Est $492,656 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft

  39 Western Ave, Brattleboro, VT 05301

  39 Western Ave, Brattleboro, VT 05301
• 

  

  /27

  $550,000 Under Contract

  • 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
• 

  

  /26

  $207,000 Sold May 27, 2025

  • 1,512 Sq Ft
  • $137/SF
  • 28 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1920

  9 Garden Dr, Brattleboro, VT 05301

  ***Offers due by Monday 4/28 at 3:00" Looking for an affordable home within walking distance to downtown Brattleboro? Come see this 8 room, 3+ bed, 2 full bath home. The 2nd floor has been updated with beautiful refinished floors, recent paint, updated bath and walkup attic with spray foam insulation. The 1st floor needs updates and repairs, but could shine as nicely as the 2nd floor! Replacement

  Sue Beaudet EXP Realty

  9 Garden Dr, Brattleboro, VT 05301
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  /4

  Est $290,909 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,250 Sq Ft

  65 Cedar St, Brattleboro, VT 05301

  65 Cedar St, Brattleboro, VT 05301
• 

  

  /47

  $299,000 Under Contract

  • 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
• 

  

  /19

  $345,000 Sold May 27, 2025

  • 2,736 Sq Ft
  • $126/SF
  • 16 Days On Market

  • 6 Beds
  • 4 Baths
  • Built 1890

  99 Clark St, Brattleboro, VT 05301

  High cash flow well maintained 4plex located in quaint Brattleboro neighborhood within proximity to the vibrant downtown, listed at a deep-value 11% cap rate. This 100% occupied building has 2x 2br and 2x1br, and a net operating income of ~38K with significant upside based on rents over 20% below market. A new owner can step into to yield over a 15% cash on cash return starting year 1, and

  Michael Gilman 3GEN Real Estate Inc

  99 Clark St, Brattleboro, VT 05301
• 

  

  /18

  Est $315,344 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,092 Sq Ft

  48 Speno Ct, Brattleboro, VT 05301

  48 Speno Ct, Brattleboro, VT 05301
• 

  

  /60

  $649,000 Under Contract

  • 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

  Karen Hoppe Berkley & Veller Greenwood Country

  49 Tyler St, Brattleboro, VT 05301
• 

  

  /23

  $180,000 Sold May 23, 2025

  • 930 Sq Ft
  • $194/SF
  • 49 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1966

  39 Brookside Dr Unit 5, Brattleboro, VT 05301

  Desirable 2 bedroom, 1 bath low maintenance, affordable home. Your spacious living/dining area has sliders looking out to the woods and a small yard space. Upstairs are 2 large bedrooms and a full bath. The lower level is a 465 square foot basement for extra storage with washer/dryer hookup. The entire interior has been freshly painted, new kitchen cabinets, countertop, new flooring, new

  Angela Sherman Brattleboro Area Realty

  39 Brookside Dr Unit 5, Brattleboro, VT 05301
• 

  

  /15

  Est $319,339 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,578 Sq Ft

  6 Sycamore St, Brattleboro, VT 05301

  6 Sycamore St, Brattleboro, VT 05301
• 

  

  /29

  $329,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,548 Sq Ft

  11 Maple St, Brattleboro, VT 05301

  Charming and well-built Cape-style home featuring 4 bedrooms and 2 full baths. The updated kitchen boasts tiled floors, generous counter space, and modern finishes—perfect for the home chef. Just off the kitchen, the dining room includes a sliding door that opens to the backyard and patio, ideal for indoor-outdoor entertaining.Beautiful hardwood floors run throughout the home—no carpet here.

  Monica Sumner BHG Masiello Brattleboro

  11 Maple St, Brattleboro, VT 05301
• 

  

  /33

  $348,000 Sold May 21, 2025

  • 2,313 Sq Ft
  • $150/SF
  • 50 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1940

  145 Marlboro Ave, Brattleboro, VT 05301

  Marlboro Avenue! A desirable and sunny neighborhood of sweet homes known for its friendliness and truly convenient location. This attractive 3 bedroom, 2 bath home with a fantastic fenced-in yard has many sought-after key features. Current owners have added mini-splits, a huge, enclosed porch- perfect for a mudroom and additional living space. They have renovated the kitchen, including

  Stephanie Peduzzi-Baker Brattleboro Area Realty

  145 Marlboro Ave, Brattleboro, VT 05301
• 

  

  /39

  Est $427,412 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,894 Sq Ft

  63 Greenhill Pkwy, Brattleboro, VT 05301

  63 Greenhill Pkwy, Brattleboro, VT 05301
• 

  

  /10

  $175,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 3,370 Sq Ft

  148 Elliot St, Brattleboro, VT 05301

  Spring Price Reduction! 3 One bedroom units and 4 single room occupancy units (SROs) w a shared bathroom and dishwashing area. Newer shingle roof on rear addition. The unfinished basement is spray foam insulated with a vapor barrier. Recent fire and safety inspection. Building needs a hands-on owner willing to take on some maintenance and improvements. Solid returns with opportunity to enhance

  Steve Schoppmeyer BHG Masiello Brattleboro

  148 Elliot St, Brattleboro, VT 05301
• 

  

  /36

  $396,023 Sold May 13, 2025

  • 2,232 Sq Ft
  • $177/SF
  • 9 Days On Market

  • 6 Beds
  • 3 Baths
  • Built 1920

  711 Western Ave, Brattleboro, VT 05301

  Nice location on Western Avenue, sitting up above the road, on an open lot. There is ample parking and the side yard has a sitting area and garden space. Enter the main house through the entryway hall and into the mudroom. Some of the nice features in this home are the walk-in pantry, period natural woodwork, gorgeous maple flooring, built-ins and tasteful and fun light fixtures throughout!

  Victoria Woods Brattleboro Area Realty

  711 Western Ave, Brattleboro, VT 05301
• 

  

  /37

  Est $638,735 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,044 Sq Ft

  145 Greenhill Pkwy, Brattleboro, VT 05301

  145 Greenhill Pkwy, Brattleboro, VT 05301
• 

  

  /5

  $680,000 Under Contract

  • 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
• 

  

  /26

  $118,000 Sold May 09, 2025

  • 1,873 Sq Ft
  • $63/SF
  • 215 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1869

  1149 Western Ave, Brattleboro, VT 05301

  Check out this 4 bedroom, 2 bathroom home in Southern Vermont. This house has town water and sewer as well as high speed internet available. The house does needs work, but would make a great winter project. The location could also be a great spot for a professional office, but you would need to discuss what options are available with town.

  Derek Eisenberg Continental Real Estate Group, Inc.

  1149 Western Ave, Brattleboro, VT 05301
• 

  

  /34

  Est $282,117 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,038 Sq Ft

  56 Orchard St, Brattleboro, VT 05301

  56 Orchard St, Brattleboro, VT 05301

Showing Results 161 - 200, Page 5 of 18