Windham, VT Homes

• 

  

  

  /36

  $317,000 Sold Jun 27, 2025

  • 1,300 Sq Ft
  • $244/SF
  • 59 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1943

  51 Parkside Ave, Brattleboro, VT 05301

  Remodeled adorable Cape in a very sweet neighborhood! Since 2022 the current owner has made so many impressive improvements. The new kitchen is bight and contemporary. Tastefully done with new counter-tops, cabinets, flooring, sink and appliances. The dining room has new floors, paint and a propane heater that opens to the deck and a level yard. The labor of love continues throughout the first

  Kristen Ziter Taylor Brattleboro Area Realty

  51 Parkside Ave, Brattleboro, VT 05301
• 

  

  

  /14

  Est $316,052 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,492 Sq Ft

  131 Oak Grove Ave, Brattleboro, VT 05301

  131 Oak Grove Ave, Brattleboro, VT 05301
• 

  

  

  /58

  $599,000

  • 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
• 

  

  

  /24

  $328,000 Sold Jun 23, 2025

  • 1,536 Sq Ft
  • $214/SF
  • 169 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1950

  414 Old Guilford Rd, Brattleboro, VT 05301

  Nestled on a dead end town road, kissing Fort Dummer state park and it's more than 200 acres of forest with trails and campsites, this is a special deal! Minutes to everything Brattleboro but snugged up on almost 4 acres of your own enchanting adventure! With a yard full of flowering bushes, trees and perennials, you will be surrounded by a sweet landscape, with plenty of room for your own

  Christine Lewis Brattleboro Area Realty

  414 Old Guilford Rd, Brattleboro, VT 05301
• 

  

  

  /16

  Est $189,151 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,343 Sq Ft

  23 Winter Ct, Brattleboro, VT 05301

  23 Winter Ct, 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
• 

  

  /37

  $375,000 Sold Jun 16, 2025

  • 1,632 Sq Ft
  • $230/SF
  • 66 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1998

  146 Sherwood Cir, Brattleboro, VT 05301

  If you’re looking for privacy, space to roam, and the convenience of being just 3 miles from downtown Brattleboro, this charming Cape-style home is a must-see! Set on a beautifully landscaped 1.16-acre lot in a desirable neighborhood, this 3-bedroom, 1.5 bath home sits slightly elevated above the others, offering stunning mountain views and all-day natural sunlight. The open-concept kitchen and

  Kate Barry EXP Realty

  146 Sherwood Cir, Brattleboro, VT 05301
• 

  

  /24

  Est $283,391 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,514 Sq Ft

  94 Fuller Dr, Brattleboro, VT 05301

  94 Fuller Dr, Brattleboro, VT 05301
• 

  

  /60

  $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
• 

  

  /25

  $315,000 Sold Jun 13, 2025

  • 1,340 Sq Ft
  • $235/SF
  • 50 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1988

  71 Whetstone Dr, Brattleboro, VT 05301

  Tucked in a sweet newer neighborhood, this home is not to be missed. Perfect for one floor living and aging in place, but versatile enough for choosing an upstairs bedroom! There is a one car attached garage and sunny deck with a slider to the dining area. The open concept with a vaulted ceiling gives a spacious, light filled living area. Some tlc needed but well worth a painting party.

  Christine Lewis Brattleboro Area Realty

  71 Whetstone Dr, Brattleboro, VT 05301
• 

  

  /24

  Est $320,087 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,500 Sq Ft

  62 Highland St, Brattleboro, VT 05301

  62 Highland St, Brattleboro, VT 05301
• 

  

  /54

  $2,490,000

  • 7 Beds
  • 7.5 Baths
  • 6,518 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
• 

  

  /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
• 

  

  /25

  Est $245,958 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,033 Sq Ft

  88 Washington St, Brattleboro, VT 05301

  88 Washington St, 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
• 

  

  /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
• 

  

  /30

  Est $328,780 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft

  20 Washington St, Brattleboro, VT 05301

  20 Washington 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
• 

  

  /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
• 

  

  /27

  Est $223,745 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 900 Sq Ft

  10 Washington St, Brattleboro, VT 05301

  10 Washington St, 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
• 

  

  /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
• 

  

  /17

  Est $296,817 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,927 Sq Ft

  18 Central St, Brattleboro, VT 05301

  18 Central 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
• 

  

  /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
• 

  

  /31

  Est $231,938 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,592 Sq Ft

  39 Clark St, Brattleboro, VT 05301

  39 Clark St, Brattleboro, VT 05301
• 

  

  /15

  $75,000

  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
• 

  

  /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
• 

  

  /18

  Not Listed For Sale

  • Studio
  • 1,683 Sq Ft

  60 Clark St, Brattleboro, VT 05301

  60 Clark St, 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
• 

  

  /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 Brattleboro Area Realty

  70 Greenleaf St, Brattleboro, VT 05301
• 

  

  /33

  Est $237,944 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,722 Sq Ft

  87 Clark St, Brattleboro, VT 05301

  87 Clark St, 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
• 

  

  /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
• 

  

  /20

  Est $409,867 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,012 Sq Ft

  203 Elliot St, Brattleboro, VT 05301

  203 Elliot St, 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
• 

  

  /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
• 

  

  /22

  Est $352,257 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,689 Sq Ft

  76 Belmont Ave, Brattleboro, VT 05301

  76 Belmont Ave, Brattleboro, VT 05301
• 

  

  /5

  $270,000

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

  556 S Main St, Brattleboro, VT 05301

  What a great way to start your home ownership! A tenant can help with the monthly expenses letting you build your own reserves and take a bit of pressure off the cost of home ownership! This 2 family has two-3 bedroom units, a nice yard and off street parking. Check it out and see for yourself...please respect the 48 hour notice for tenants, mask up! No interior photos due to tenant privacy.

  Christine Lewis Brattleboro Area Realty

  556 S Main 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

Showing Results 81 - 120, Page 3 of 18