Windham, VT Homes

• 

  

  

  /17

  Est $300,673 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,000 Sq Ft

  130 Belmont Ave, Brattleboro, VT 05301

  130 Belmont Ave, Brattleboro, VT 05301
• 

  

  /2

  $145,000

  • Land
  • 2.90 Acres
  • $50,000 per Acre

  00 W River Rd, Brattleboro, VT 05301

  A 2.9 acre build-able lot in Brattleboro's Waterfront District, on heavily-trafficked Route 30, next to the well-loved Fire Arts' building. There are many allowed and conditional uses for this zoning, including Residential, Retail, Marina, Fitness, Art Gallery and more. A great location for your new business, with great visibility to over 1500 cars daily.

  John Hatton Berkley & Veller Greenwood Country

  00 W River Rd, 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
• 

  

  

  /17

  Est $259,140 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,320 Sq Ft

  155 Maple St, Brattleboro, VT 05301

  155 Maple St, Brattleboro, VT 05301
• 

  

  /2

  $350,000

  • 2 Beds
  • 4 Baths
  • 3,312 Sq Ft

  573 S Main St, Brattleboro, VT 05301

  Just around the corner! From the middle and high school, Oak grove elementary! Pop around the corner for all the high school games, exercise at the track. Interstate is minutes away for easy access to work or play! One apartment is over 1,000 square feet so tons of room for owner occupancy! 2 nice front porches. Worth looking at for either your own home or as an investment. Masks please.

  Christine Lewis Brattleboro Area Realty

  573 S Main 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
• 

  

  /35

  Est $409,427 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,560 Sq Ft

  31 Pleasant St, Brattleboro, VT 05301

  31 Pleasant St, Brattleboro, VT 05301
• 

  /2

  $370,000

  • 5 Beds
  • 4 Baths
  • 3,002 Sq Ft

  10 Birge St, Brattleboro, VT 05301

  Invest in your own home town! Full tenant roster with the easy access to laundry across the street, grocery stores, train and The Moover. Right in the heart of things with little yard to maintain! Consider as an investment in your portfolio or decide to live in one unit and have the others pay your mortgage! Good way to start, retire or increase your portfolio! Owner is a licensed appraiser.

  Christine Lewis Brattleboro Area Realty

  10 Birge 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
• 

  

  /32

  Est $355,625 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,614 Sq Ft

  36 Chestnut St, Brattleboro, VT 05301

  36 Chestnut St, Brattleboro, VT 05301
• 

  

  /30

  $325,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,146 Sq Ft

  116 Edward Heights, Brattleboro, VT 05301

  This spacious, single-level home is neatly tucked away on a large corner lot at the end of the street - no through-traffic! The interior features inviting, open living space on one end and separate rooms at the other, including a walk-in pantry, laundry room and bathroom with a step-in tub. The expansive yard offers both sun and shade, with a screened-in outbuilding (formerly a pool house) and a

  Stephanie Wilde Brattleboro Area Realty

  116 Edward Heights, Brattleboro, VT 05301
• 

  

  /20

  $79,000 Sold May 05, 2025

  • 784 Sq Ft
  • $101/SF
  • 8 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1986

  6 Thistle Hill Rd, Brattleboro, VT 05301

  This is affordable living and the perfect sized house to live comfortably. New vinyl flooring, roof and furnace. You have the added benefit of heating with wood, should you not want to use the oil furnace. This woodstove could easily be your one and only source of heat! Get it before it's gone!

  Victoria Woods Brattleboro Area Realty

  6 Thistle Hill Rd, Brattleboro, VT 05301
• 

  

  /36

  Est $299,162 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,388 Sq Ft

  122 Frost St, Brattleboro, VT 05301

  122 Frost 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
• 

  

  /43

  $229,300 Sold May 02, 2025

  • 1,139 Sq Ft
  • $201/SF
  • 28 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1998

  129 Morningside Commons, Brattleboro, VT 05301

  Beautiful move-in-ready end unit! This Brattleboro townhouse offers convenience and accessibility in a lovely community with a tennis court, in-ground swimming pool, and dedicated carport (with a hanging space for canoes and kayaks should you feel the call of the nearby Connecticut River). The spacious living room, dine-in kitchen, and 2 bedrooms can play host to many lifestyles: whether

  Zachary Zupan EXP Realty

  129 Morningside Commons, Brattleboro, VT 05301
• 

  

  /23

  Est $296,376 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,611 Sq Ft

  204 Williams St, Brattleboro, VT 05301

  204 Williams St, Brattleboro, VT 05301
• 

  

  /13

  $80,000 Pending

  • 2 Beds
  • 1 Bath
  • 949 Sq Ft

  7 Stonewall Dr Unit 60159.s07, Brattleboro, VT 05301

  This is a well cared for and improved affordable home. The airy open concept of the main space makes for a feeling of spaciousness. The primary bedroom has direct access to the full bath and laundry. The attached enclosed porch offers additional seasonal living space, The large corner lot offers good garden space and storage in the good sized storage shed.

  David Brown Berkley & Veller Greenwood Country

  7 Stonewall Dr Unit 60159.s07, Brattleboro, VT 05301
• 

  

  /49

  $380,000 Sold May 02, 2025

  • 1,901 Sq Ft
  • $200/SF
  • 49 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1918

  125 Pine St, Brattleboro, VT 05301

  This beautifully maintained single-family home offers both comfort and practical living in a charming Brattleboro neighborhood. This inviting residence features four spacious bedrooms and two full well-appointed bathrooms that abounds with natural light and creates an inviting and charming atmosphere throughout. The spacious yard includes a German Hugelkultur raised bed garden, blueberry and

  Kate Barry EXP Realty

  125 Pine St, Brattleboro, VT 05301
• 

  

  /35

  Est $371,037 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,488 Sq Ft

  25 Strand Ave, Brattleboro, VT 05301

  25 Strand Ave, Brattleboro, VT 05301
• 

  

  /28

  $200,000 Pending

  • 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
• 

  

  /16

  $235,000 Sold May 02, 2025

  • 1,056 Sq Ft
  • $223/SF
  • 52 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1988

  42 Morningside Commons, Guilford, VT 05301

  Don't miss this condo! Great location and convenient to downtown. The amenities offered by this condominium community are an in-ground pool, tennis and pickleball courts, a basketball court, hiking trails, little libraries and lovely gardens will make condo owning enjoyable. Almost everything in this immaculate stylish condo is only a couple of years old. Not only is most of this condo updated,

  Tim Berg Brattleboro Area Realty

  42 Morningside Commons, Guilford, VT 05301
• 

  

  /29

  Est $528,574 Not Listed For Sale

  • 3 Beds
  • 4.5 Baths
  • 3,913 Sq Ft

  300 Western Ave, Brattleboro, VT 05301

  300 Western Ave, Brattleboro, VT 05301
• 

  

  /56

  $235,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  67 Morningside Commons, Guilford, VT 05301

  From the rhododendron, orange day lily and morning glories in front of this condo to the herb and flower garden in the rear and with everything in between, this condo speaks "lovely". Completely updated and immaculately maintained. Kitchen features stylish cabinets, Corian counter tops, all Whirlpool stainless steel appliances and a double oven. The hanging wrought iron pot holder and fruit

  Sally Fegley BHG Masiello Brattleboro

  67 Morningside Commons, Guilford, VT 05301
• 

  

  /6

  $399,000 Sold May 02, 2025

  • 4,087 Sq Ft
  • $98/SF
  • 217 Days On Market

  • Built 1910

  79 Putney Rd, Brattleboro, VT 05301

  SUPERB OPPORTUNITY to acquire a solid, small-scale investment property, long-held by local owner/managers. First time offered in nearly 50 years!! This Victorian-era property retains much of its historic charm with hardwood flooring, large rooms, natural woodwork, high ceilings, and fireplaces in two of the four residences. Conveniently located across from the Brattleboro Common on Putney Road

  Dan Normandeau Berkley & Veller Greenwood Country

  79 Putney Rd, Brattleboro, VT 05301
• 

  

  /40

  Est $592,737 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,761 Sq Ft

  160 Guilford St, Brattleboro, VT 05301

  160 Guilford St, Brattleboro, VT 05301
• 

  

  /42

  $849,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 3,550 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
• 

  

  /28

  $460,000 Sold May 01, 2025

  • 2,051 Sq Ft
  • $224/SF
  • 0 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1920

  70 Tyler St, Brattleboro, VT 05301

  Welcome to this 1920's charmer, a perfect blend of classic Craftsman style and modern comfort! Nestled on highly coveted Tyler Street, this 4-bedroom, 1.5-bath gem offers a warm and inviting atmosphere with all the conveniences of today. As you approach, you'll be greeted by a huge covered front porch—an ideal spot for enjoying your morning coffee or relaxing in the evening. Step inside to

  Karen Hoppe Berkley & Veller Greenwood Country

  70 Tyler St, Brattleboro, VT 05301
• 

  

  /17

  Est $406,370 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,119 Sq Ft

  103 New England Dr, Brattleboro, VT 05301

  103 New England Dr, Brattleboro, VT 05301
• 

  

  /5

  $100,000 Pending

  • 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
• 

  

  /40

  $790,000 Sold May 01, 2025

  • 2,474 Sq Ft
  • $319/SF
  • 246 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2011

  373 Summit Cir, Brattleboro, VT 05301

  Motivated Sellers! Enjoy year-round comfort in this stunning Net Zero home, built in 2012 to meet the rigorous Passive House standard. You won’t pay a cent to heat and cool this all-electric house or even charge your EV. Gorgeous woodwork, soaring ceilings, and premium finishes make this light-filled sustainable home a rare find. With superinsulated walls, triple-glazed tilt-turn windows, ducted

  Mike Masters Four Seasons Sotheby's Int'l Realty

  373 Summit Cir, Brattleboro, VT 05301
• 

  

  /33

  Est $348,029 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,184 Sq Ft

  55 Thayer Ridge Rd, Brattleboro, VT 05301

  55 Thayer Ridge Rd, Brattleboro, VT 05301
• 

  

  /22

  $325,000 Pending

  • 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
• 

  

  /39

  $475,000 Sold Apr 23, 2025

  • 2,823 Sq Ft
  • $168/SF
  • 121 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1905

  101 Washington St, Brattleboro, VT 05301

  From the moment you step inside, you’ll be captivated by the timeless beauty of this home. An inviting foyer welcomes you, leading to an elegant, curved staircase that ascends to the second floor—showcasing craftsmanship that would be nearly impossible to replicate today. The home’s original woodwork, plaster, lathe walls, wood trim, and doors are so well preserved that they appear as though they

  Thomas Dahlin Berkley & Veller Greenwood Country

  101 Washington St, Brattleboro, VT 05301
• 

  

  /17

  Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,192 Sq Ft

  124 Green St, Brattleboro, VT 05301

  124 Green St, Brattleboro, VT 05301
• 

  

  /59

  $547,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 5,850 Sq Ft

  628 S Main St, Brattleboro, VT 05301

  Absolutely Gorgeous In-Town Home with Exceptional Attention to Detail.This stunning residence offers over 5,000 square feet of meticulously designed living space in the main house, plus a fully separate accessory dwelling with two independent living areas—ideal for extended family, guests, or producing income. Additionally there is a two-car garage with an integrated service pit for

  Kerry Mulverhill Brattleboro Area Realty

  628 S Main St, Brattleboro, VT 05301
• 

  

  /33

  $350,000 Sold Apr 01, 2025

  • 1,754 Sq Ft
  • $200/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  113 Stockwell Dr, Brattleboro, VT 05301

  Come home to this meticulously maintained home. Upstairs boasts an open concept Kitchen/dining/living space, with beautiful Oak flooring. Down the hall, 2 bedrooms share a full bath with dual sinks. In addition, the primary bedroom has an en suite 3/4 bath. The finished lower level has a large rec room with a newer 3 zone on demand hot water heating system and direct entrance to the oversized 1

  Victoria Woods Brattleboro Area Realty

  113 Stockwell Dr, Brattleboro, VT 05301
• 

  

  /20

  Est $267,541 Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 2,150 Sq Ft

  173 Green St, Brattleboro, VT 05301

  173 Green St, Brattleboro, VT 05301
• 

  

  /8

  $170,000 Pending

  • Land
  • 18 Acres
  • $9,290 per Acre

  0 Gibson Rd, Brattleboro, VT 05301

  This just doesn't happen, a large parcel,18+ acres, in a desirable Brattleboro location. Just up the road the Brattleboro Country Club. Here you'll find stonewalls, small, intriguing streams and mature hard and softwoods. It's the pine trees, however that take center stage, some of them stretching up over 100 feet. If the acreage isn't quite enough there's an adjacent parcel on the market as

  Bill Hickok Berkley & Veller Greenwood Country

  0 Gibson Rd, Brattleboro, VT 05301
• 

  

  /31

  $307,000 Sold Mar 19, 2025

  • 1,760 Sq Ft
  • $174/SF
  • 4 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1990

  473 Williams St, Brattleboro, VT 05301

  Sunny South-Facing End Unit Townhome with Land in Brattleboro, VT. Enjoy the perfect blend of privacy, natural light, and convenience with this unique south-facing end unit townhome. This home is one of three townhomes that share a common wall, has its own land and no HOA fees. Located just minutes from downtown, the Farmers Market and other community events. Versatile! This light filled, well

  Liz LaVorgna Berkley & Veller Greenwood Country

  473 Williams St, Brattleboro, VT 05301
• 

  

  /18

  Est $314,338 Not Listed For Sale

  • 7 Beds
  • 3 Baths
  • 3,540 Sq Ft

  108 High St, Brattleboro, VT 05301

  108 High St, Brattleboro, VT 05301

Showing Results 121 - 160, Page 4 of 18