Windham, VT Homes in ZIP Code 05301

• 

  

  

  /37

  $455,000 Sold Jul 18, 2025

  • 1,608 Sq Ft
  • $283/SF
  • 48 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1983

  880 Green River Rd, Brattleboro, VT 05301

  Sweet, passive solar cape in the delightful Green River Road area of Guilford, Vermont. Meticulously located in a meadow, well set back from the road, this inviting and cozy home adeptly collects and distributes the sun’s energy when needed in the winter. While designed for passive solar comfort and low energy needs, the home also offers modern conveniences, such as a newer propane furnace, a

  Dan Normandeau Berkley & Veller Greenwood Country

  880 Green River Rd, Brattleboro, VT 05301
• 

  

  

  /30

  Not Listed For Sale

  • 8 Beds
  • 4 Baths
  • 3,854 Sq Ft

  100 Frost St, Brattleboro, VT 05301

  100 Frost St, Brattleboro, VT 05301
• 

  

  

  /35

  $525,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 2,456 Sq Ft

  1073 Upper Dummerston Rd, Brattleboro, VT 05301

  This very Vermont country home is nestled on a peaceful, beautifully landscaped 1.5 acre lot along Upper Dummerston Road. Built with unparalleled craftsmanship by some of the region’s finest artisans, the home exudes exceptional quality throughout. At the heart of the residence is a large chef's kitchen, complete with a gas fireplace, granite countertops, solid maple cabinetry, and premium Wolf

  Thomas Dahlin Berkley & Veller Greenwood Country

  1073 Upper Dummerston Rd, Brattleboro, VT 05301
• 

  

  

  /41

  $545,000 Sold Jul 18, 2025

  • 2,450 Sq Ft
  • $222/SF
  • 48 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1880

  441 Guilford St, Brattleboro, VT 05301

  Perched proudly on a knoll, this mid-19th-century colonial was one of two farmsteads in this neighborhood of Brattleboro, VT. This stunning, 4-BR, 2-BA hip roof colonial & spacious, 2-story barn have been lovingly cared for by the same owner for 56 years! Now is your opportunity to own a New England classic in a neighborhood setting, but country feel - all w/in very close proximity to town

  Dan Normandeau Berkley & Veller Greenwood Country

  441 Guilford St, Brattleboro, VT 05301
• 

  

  

  /24

  Est $333,617 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft

  118 Partridge Rd, Guilford, VT 05301

  118 Partridge Rd, Guilford, VT 05301
• 

  

  /20

  $495,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 2,400 Sq Ft

  21 Howard St, Brattleboro, VT 05301

  This beautiful Victorian home is just a short stroll from vibrant Brattleboro and has access to a huge town trail network. Nicely landscaped and has a partially fenced yard for pets or children. The house has lovely Victorian detailing and includes 3 covered porches. The formal entry has hardwood flooring, period staircase, stained glass window and a 3/4 bath. The adjacent front parlor includes

  Robert Doyle Berkley & Veller Greenwood Country

  21 Howard St, Brattleboro, VT 05301
• 

  

  /25

  $349,000 Sold Jul 15, 2025

  • 1,503 Sq Ft
  • $232/SF
  • 42 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1928

  6 Willow St, Brattleboro, VT 05301

  This home truly has it all and is conveniently located on one Brattleboro's most charming streets. Close to shopping, restaurants, and downtown yet tucked away from it all. The large fenced lot has good exposure for gardening. Inside the home you will find 3 bedrooms and a fabulous renovated attic, complete with custom cabinetry and shelving. Enjoy indoor/outdoor entertaining with french-door

  John Hatton Berkley & Veller Greenwood Country

  6 Willow St, Brattleboro, VT 05301
• 

  

  /31

  Est $339,534 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  47 Sherwood Cir, Brattleboro, VT 05301

  47 Sherwood Cir, Brattleboro, VT 05301
• 

  

  /20

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,178 Sq Ft

  17 Winter Ct, Brattleboro, VT 05301

  Classic Ranch Style Home! Just starting out or thinking of downsizing? This could be the one! Nestled in a sweet neighborhood, this charming ranch offers easy one-level living just minutes from downtown shopping, schools, and recreation. Set on a manageable 0.2 acre lot, this home features a bright enclosed porch/bonus room perfect for morning coffee, reading, or relaxing year-round. Continuing

  Liz LaVorgna Berkley & Veller Greenwood Country

  17 Winter Ct, Brattleboro, VT 05301
• 

  

  /60

  $130,000 Sold Jul 15, 2025

  • 1,392 Sq Ft
  • $93/SF
  • 204 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  7 Deepwood Park, Brattleboro, VT 05301

  Price improvement!!! Charming one level mobile home with addition in Tri Park Co-op. 3 bedrooms, 2 bathrooms, eat in kitchen, large living room, den/other room, large back deck for entertaining and BBQs and a full concrete foundation!!! Great property! Don't miss this opportunity! Seller to pay buy in fee to the park for buyer at time of closing!!!

  Emily Lagerberg R.H. Thackston & Company

  7 Deepwood Park, Brattleboro, VT 05301
• 

  

  /38

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 4,410 Sq Ft

  773 Guilford St, Brattleboro, VT 05301

  773 Guilford St, 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
• 

  

  /10

  $40,000 Sold Jul 14, 2025

  • Land
  • 0.29 Acre
  • $137,931 per Acre

  • 2 Days On Market

  42-44 Canal St, Brattleboro, VT 05301

  .31 Acre lot in downtown Brattleboro with 4 rental storage units. Storage units with parking lot can bring in ~10K+ of revenue if used as such, or lot is perfect for townhome development, which is highly supported by the Town. Storage units rents can rent at $150 each. The lot recently appraised at $45,000 (please e-mail for appraisal). Parking lot currently used by residents of adjacent

  Michael Gilman 3GEN Real Estate Inc

  42-44 Canal St, Brattleboro, VT 05301
• 

  

  /40

  Est $138,418 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 595 Sq Ft

  335 Depot Rd Unit 2, Williamsville, VT 05362

  335 Depot Rd Unit 2, Williamsville, VT 05362
• 

  

  /34

  $299,900

  • 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
• 

  

  /23

  $93,999 Sold Jul 14, 2025

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

  • 3 Beds
  • 2 Baths
  • Built 2024

  8 Deepwood Park, Brattleboro, VT 05301

  Welcome to 8 Deepwood Dr, 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 Deepwood Park, Brattleboro, VT 05301
• 

  

  /32

  Est $391,687 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft

  348 Green River Rd, Brattleboro, VT 05301

  348 Green River Rd, Brattleboro, VT 05301
• 

  

  /28

  $249,000

  • 3 Beds
  • 1 Bath
  • 1,213 Sq Ft

  5704 Coolidge Hwy, Guilford, VT 05301

  Tucked back off the road, equidistant between Brattleboro, Vermont and Bernardston, MA, this “cute-as-a-button,” chalet-influenced cape is an excellent opportunity for a cozy, 3-bedroom home or an Airbnb, on a 7.9-ac lot in beautiful Guilford, Vermont. Nice mix of sun and shade. Excellent gardening spot. High-speed internet available. Single-level living is possible, with a first-floor

  Dan Normandeau Berkley & Veller Greenwood Country

  5704 Coolidge Hwy, Guilford, VT 05301
• 

  

  /48

  $310,000 Sold Jul 14, 2025

  • 1,300 Sq Ft
  • $238/SF
  • 57 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1924

  52 Belmont Ave, Brattleboro, VT 05301

  Step into this beautifully updated Cape style home offering a perfect blend of classic charm and modern updates. Ideally located near the hospital, public transportation, shopping and more, providing both convenience and comfort in an ideal location. From the moment you enter, you’ll be greeted by the warm inviting ambiance, fall in love with the stunning wood flooring and rich natural woodwork

  Kerry Mulverhill Brattleboro Area Realty

  52 Belmont Ave, Brattleboro, VT 05301
• 

  

  /35

  Est $408,332 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,272 Sq Ft

  73 Clark Rd, Brattleboro, VT 05301

  73 Clark Rd, Brattleboro, VT 05301
• 

  

  /35

  $399,000

  • 4 Beds
  • 2 Baths
  • 1,768 Sq Ft

  1469 Higley Hill Rd, West Marlboro, VT 05363

  Cozy Log Cabin with Sunny Addition, Small Pond & Sugar House on 5 Acres in Marlboro, VermontThis inviting log cabin blends classic Vermont charm with a thoughtfully designed, light-filled addition—offering comfort, space, and versatility on 5 peaceful acres. Tucked away on a quiet dirt road in a desirable Marlboro neighborhood, the property features a small pond and a traditional sugar house,

  Melissa Nebelski Skihome Realty

  1469 Higley Hill Rd, West Marlboro, VT 05363
• 

  

  /33

  $209,000 Sold Jul 11, 2025

  • 1,248 Sq Ft
  • $167/SF
  • 42 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2018

  3 Record Dr, Brattleboro, VT 05301

  This spacious double-wide mobile home offers structural upgrades not often found in park settings. Set on a full poured concrete walk-out basement with I-beam supports and 8" basement walls, the property includes an expansive deck constructed with reinforced framing. Inside, a primary suite with oversized glass stall shower and oversized closet complement an ADA-accessible layout featuring an

  Erica Reynolds Southern Vermont Realty Group

  3 Record Dr, Brattleboro, VT 05301
• 

  

  /31

  Est $391,484 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,240 Sq Ft

  140 Marynuk Rd, Guilford, VT 05301

  140 Marynuk Rd, Guilford, VT 05301
• 

  

  /31

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  321 Leonard Rd, Dummerston, VT 05301

  Get ready for your new favorite property. Located in highly-desirable West Dummerston, just 10 minutes from downtown Brattleboro, this energy-efficient Unity high performance home is waiting for you. It’s a very cozy 3-bedroom, 2 full bathroom single-level home on 0.88 acres. Built of pre-fabricated components in factory-controlled conditions, this house is just some solar panels away from

  John Hatton Berkley & Veller Greenwood Country

  321 Leonard Rd, Dummerston, VT 05301
• 

  

  /14

  $65,000 Sold Jul 11, 2025

  • 924 Sq Ft
  • $70/SF
  • 70 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1978

  4 Brookwood Dr, West Brattleboro, VT 05301

  Well-maintained single-wide mobile home on a double lot in Tri-Park Coop. Fresh paint and new flooring throughout, newer appliances, and new hot water heater. This home has a light-filled living room, spacious eat-in kitchen, and primary bedroom with half-bath and custom barn door. Enjoy the sounds of the brook from the covered porch and large fenced-in yard with space for gardening. There is a

  Cassandra Ehrlich BHG Masiello Brattleboro

  4 Brookwood Dr, West Brattleboro, VT 05301
• 

  

  /38

  Est $429,650 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,436 Sq Ft

  71 Great Blue Heron Dr, Guilford, VT 05301

  71 Great Blue Heron Dr, Guilford, VT 05301
• 

  /2

  $90,000

  • 3 Beds
  • 1 Bath
  • 1,030 Sq Ft

  93 Clark St, Brattleboro, VT 05301

  An affordable opportunity for a new beginning, for both you and the home! Located in an evolving neighborhood where a new generation is investing, walk to downtown. This corner lot has off street parking, a bit of yard for some planting or sunning, and what the current owner has used as a workshop. This one will take cash or a rehab loan, but is being occupied so systems are working. Please,

  Christine Lewis Brattleboro Area Realty

  93 Clark St, Brattleboro, VT 05301
• 

  

  /29

  $269,000 Sold Jul 07, 2025

  • 2,242 Sq Ft
  • $120/SF
  • 65 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1890

  27 Horton Place, Brattleboro, VT 05301

  Outstanding Investment Opportunity Near Downtown Brattleboro. Just minutes from the vibrant Brattleboro town center, this versatile two-unit property offers unmatched convenience and strong potential for investors or owner-occupants alike. Enjoy close proximity to shopping, dining, and professional services, as well as Brattleboro Memorial Hospital, local schools, and several parks for year-round

  Patrice Schneider Southern Vermont Realty Group

  27 Horton Place, Brattleboro, VT 05301
• 

  

  /18

  Est $317,697 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft

  103 Great Blue Heron Dr, Guilford, VT 05301

  103 Great Blue Heron Dr, Guilford, VT 05301
• 

  

  /60

  $899,000

  • 4 Beds
  • 3.5 Baths
  • 3,685 Sq Ft

  155 Hillwinds N, Brattleboro, VT 05301

  Situated in Brattleboro’s premier, rural neighborhood, this much-loved home is a masterclass in thoughtful design, meticulous construction, & refined living. A grand dbl-door foyer welcomes you into a soaring entry hall that flows seamlessly into a sunken, dbl-height ceiling LR - complete w/ granite-surround FP, custom blt-ins, & crowned by a dramatic balcony overlook. Light pours in from every

  Dan Normandeau Berkley & Veller Greenwood Country

  155 Hillwinds N, Brattleboro, VT 05301
• 

  

  /33

  $310,000 Sold Jul 03, 2025

  • 1,666 Sq Ft
  • $186/SF
  • 25 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  34 Hampshire Cir, Brattleboro, VT 05301

  Charming home located in peaceful neighborhood setting of Carriage Hill. Move right in to this inviting home located on quiet cul-de-sac. The spacious eat-in kitchen features a breakfast bar and sliding doors leading to a back deck — perfect for morning coffee or summer gatherings. The bright living room boasts a beautiful bay window that fills the space with natural light. The main level

  Carol Slocum Keller Williams Realty Metro-Keene

  34 Hampshire Cir, Brattleboro, VT 05301
• 

  

  /37

  Est $302,933 Not Listed For Sale

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

  298 Sweet Pond Rd, Guilford, VT 05301

  298 Sweet Pond Rd, Guilford, VT 05301
• 

  /2

  $89,000

  • 4 Beds
  • 3 Baths
  • 2,108 Sq Ft

  321 Williams St, Brattleboro, VT 05301

  Great opportunity for starting or expanding your investment portfolio. Good rental income and affordable property. Nice location. Good parking for tenants and private porches. Minimal yard maintenance.

  Susan Bellville Bellville Realty

  321 Williams St, Brattleboro, VT 05301
• 

  

  /39

  $312,450 Sold Jul 03, 2025

  • 1,758 Sq Ft
  • $178/SF
  • 49 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1952

  96 Brattle St, Brattleboro, VT 05301

  Loved and owned by the same family for over 50 years! Very well maintained 1952 Cape with 1 car garage under. This home features first floor bedroom, 2 bedrooms on the second floor. It also has first floor laundry, screen room off the family room, large kitchen and formal living room with fireplace. Two bedrooms and full bath on the second floor round out this wonderful family home. Showings

  Darlene Conca Keller Williams Realty Metro-Keene

  96 Brattle St, Brattleboro, VT 05301
• 

  

  /39

  Est $687,889 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,272 Sq Ft

  762 Stage Rd, Guilford, VT 05301

  762 Stage Rd, Guilford, VT 05301
• 

  

  /16

  $259,900

  • Land
  • 29 Acres
  • $8,901 per Acre

  1270 Melendy Hill Rd, Guilford, VT 05301

  A rare find! This amazing land has long range views, privacy and close to everything! There is a right of way for egress, and will be perfect for an off grid tuck away cabin or primary. A small meadow is part of the 2 acre exemption for house site, just at the end of the existing drive...easy to get to and just the beginning of the land. Mostly Black Birch, Sugar Maple and Hemlock, there is

  Christine Lewis Brattleboro Area Realty

  1270 Melendy Hill Rd, Guilford, VT 05301
• 

  

  /36

  $525,000 Sold Jun 30, 2025

  • 1,284 Sq Ft
  • $409/SF
  • 11 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1920

  1486 Sweet Pond Rd, Guilford, VT 05301

  Tucked away on 25.7 picturesque acres along the beloved Sweet Pond Road—with easy, year-round access—this enchanting property welcomes you with two stately sentinel trees and a sweeping wraparound driveway. The first to greet you is a spacious barn, where cords of dry firewood await cozy evenings by the classic Vigilant wood stove. The barn also offers a heated studio and office—ideal for

  Desiree Stango Berkley & Veller Greenwood Country

  1486 Sweet Pond Rd, Guilford, VT 05301
• 

  

  /19

  Est $344,932 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,351 Sq Ft

  1190 Stage Rd, Guilford, VT 05301

  1190 Stage Rd, Guilford, VT 05301
• 

  

  /47

  $995,000

  • 5 Beds
  • 1 Bath
  • 1,224 Sq Ft

  6036 Jacksonville Stage Rd, Guilford, VT 05301

  Welcome to a rare and breathtaking slice of Vermont. This expansive 216-acre farm offers a beautiful mix of open pastures, mature woodlands, fruit trees, berry bushes, and a small section of scenic wetlands – a true haven for nature lovers and outdoor enthusiasts seeking peace and space in every direction. Set along a quiet dirt road near the Massachusetts border, with the added convenience of

  Melissa Nebelski Skihome Realty

  6036 Jacksonville Stage Rd, Guilford, VT 05301
• 

  

  /18

  $420,000 Sold Jun 30, 2025

  • 2,880 Sq Ft
  • $146/SF
  • 88 Days On Market

  • 6 Beds
  • Built 1970

  238 Marlboro Rd, Brattleboro, VT 05301

  This 6-unit fully-leased and cashflowing property is in great condition. With gross rents of $66,000, expenses (including property taxes) of $14,538, and net income of $51,462, this investment property shows a 12.1% cap rate. With stable, long-term tenants on annual leases and fully-separated utilities in 5 of the 6 units, just about everything is taken care of. Built in 1970, the property is

  Steve Schoppmeyer BHG Masiello Brattleboro

  238 Marlboro Rd, Brattleboro, VT 05301

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