Windham, VT Homes in ZIP Code 05301

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  /13

  $79,000

  • Land
  • 3.69 Acres
  • $21,409 per Acre

  0 Honeycomb Hill, Marlboro, VT 05301

  On the privately maintained road of Honeycomb Hill sits this 3.69 acre lot. The wooded parcel has young tree growth and slopes gently. There are three areas that are fairly level and open and may be suitable building sites. Just 30 minutes to Mt. Snow, 25 minutes to Brattleboro and 15 minutes to Harriman Reservoir, this conveniently located parcel offers easy access to all of Southern Vermont's

  Laura D'Angelo Berkley & Veller Greenwood Country

  0 Honeycomb Hill, Marlboro, 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 $315,069 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,532 Sq Ft

  1219 Wickopee Hill Rd, Dummerston, VT 05301

  1219 Wickopee Hill Rd, Dummerston, VT 05301
• 

  

  

  /41

  $265,000

  • 4 Beds
  • 1 Bath
  • 1,612 Sq Ft

  178 Parsons Rd, Wilmington, VT 05363

  Charming Cape-style home set on 1.7 beautifully landscaped acres, featuring a detached two-car garage. The expansive yard includes established gardens, a BBQ area, a barn, and two additional sheds in need of some TLC. Located just 4 miles from downtown Wilmington, you’ll enjoy easy access to shopping, dining, and year-round outdoor activities like skiing, golfing, hiking, biking, and boating. The

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  178 Parsons Rd, Wilmington, VT 05363
• 

  

  

  /59

  $850,000 Sold May 30, 2025

  • 2,855 Sq Ft
  • $298/SF
  • 28 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1790

  232 Butternut Hill Rd, Guilford, VT 05301

  High Meadow Farm gets its name from the high meadow above the main house where the view up the CT River Valley across into NH is lovely. The property's legacy dates back to the Revolutionary War, (See attached history). Imagine 10.84 acres of unrivaled beauty with a picturesque post & beam timber-framed farmhouse, a versatile 700 square-foot guest house, a 20 x 25 1780s post & beam barn with

  Kristen Ziter Taylor Brattleboro Area Realty

  232 Butternut Hill Rd, Guilford, VT 05301
• 

  

  /36

  Est $321,292 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,026 Sq Ft

  1670 Upper Dummerston Rd, Dummerston, VT 05301

  1670 Upper Dummerston Rd, Dummerston, 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
• 

  

  /28

  $275,000 Sold May 28, 2025

  • 1,085 Sq Ft
  • $253/SF
  • 51 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1956

  401 Hague Rd, Dummerston, VT 05301

  Sweet 2 bedroom, 1 bath ranch that sits on a knoll with 3 surrounding acres. Lots of improvements, including new flooring throughout, new garage/breezeway roof, new kitchen cabinets, granite counter top, stove and dishwasher. Fresh paint through out. Lovely open concept kitchen, dining and living room with lots of light. The attached oversized 2 car and breezeway is a true bonus to an already

  Susan Bellville Bellville Realty

  401 Hague Rd, Dummerston, VT 05301
• 

  

  /10

  Est $248,530 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,079 Sq Ft

  272 Stickney Brook Rd, Dummerston, VT 05301

  272 Stickney Brook Rd, Dummerston, VT 05301
• 

  

  /34

  $399,000

  • 3 Beds
  • 2 Baths
  • 2,190 Sq Ft

  1637 Adams Brook Rd, Marlboro, VT 05301

  Tucked away in the rolling hills of Marlboro, Vermont, this off-the-grid house sits on 8 plus acres of forest and meadowland, offering a perfect blend of rustic charm and sustainable living. Powered by a newer 48V Schneider solar power system, with a backup propane generator, the home is a self-sufficient sanctuary far from the hustle of modern life. An open concept floor plan offers much

  Kassie Rubico Berkley & Veller Greenwood Country

  1637 Adams Brook Rd, Marlboro, 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
• 

  

  /12

  Est $227,000 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 924 Sq Ft

  129 West St, Brattleboro, VT 05301

  129 West 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
• 

  

  /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
• 

  

  /40

  Est $356,831 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,716 Sq Ft

  36 Goldfinch Ln, Brattleboro, VT 05301

  36 Goldfinch Ln, Brattleboro, VT 05301
• 

  

  /52

  $329,000

  • 3 Beds
  • 2 Baths
  • 1,239 Sq Ft

  3185 Higley Hill Rd, Guilford, VT 05301

  Originally built for the 1980 Lake Placid Winter Olympics, this iconic A-frame was later relocated to a serene 2+ acre setting in Marlboro Vermont. Tucked away on a quiet paved road, this 3-bedroom, 2-bath home blends rustic charm with thoughtful updates, including spacious additions and featuring a large mudroom—perfect for storing winter gear after a day on the slopes. The open-concept

  Chad Lackey Deerfield Valley Real Estate

  3185 Higley Hill Rd, Guilford, 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
• 

  

  /32

  Est $296,286 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,363 Sq Ft

  499 S Main St, Brattleboro, VT 05301

  499 S Main 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
• 

  

  /43

  $549,000 Sold May 23, 2025

  • 1,876 Sq Ft
  • $293/SF
  • 184 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 2006

  500 Hague Rd, Dummerston, VT 05301

  Discover this exceptional equestrian property in Dummerston, VT, combining rustic charm with modern amenities. The 1,876 sq. ft. home features an open-concept design with 10-foot tongue-and-groove ceilings, creating a spacious atmosphere ideal for entertaining. The kitchen is fully equipped with stainless steel appliances, ample counter space, and a large center island. There’s also potential for

  Kate Barry EXP Realty

  500 Hague Rd, Dummerston, VT 05301
• 

  

  /23

  Est $271,309 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,539 Sq Ft

  380 S Main St, Brattleboro, VT 05301

  380 S Main St, 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
• 

  

  /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
• 

  

  /16

  Est $374,817 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,722 Sq Ft

  68 Wilsons Woods Rd, Brattleboro, VT 05301

  68 Wilsons Woods Rd, Brattleboro, VT 05301
• 

  

  /15

  $74,900

  • Land
  • 3.58 Acres
  • $20,922 per Acre

  Lot 4 Ghastly Job Way, Wilmington, VT 05363

  3.58 acres east of Wilmington village. This property is ready to build on, site work has commenced; tree clearing and partial driveway installed, fully engineered, survey, and Sate of Vermont Wastewater Permit for the construction of a three bedroom home. This parcel offers a great location, close to Lake Raponda for swimming, near Molly Stark State Park for hiking and minutes to Lake Whitingham

  Monique White Deerfield Valley Real Estate

  Lot 4 Ghastly Job Way, Wilmington, VT 05363
• 

  

  /26

  $300,000 Sold May 19, 2025

  • Land
  • 160 Acres
  • $1,875 per Acre

  • 621 Days On Market

  4600 Augur Hole Rd, Marlboro, VT 05344

  This property of 169+/- acres blankets the side of a mountain along the Augur Hole valley. There is over 700 feet of the Marlboro Branch River running through the property: a trout fishermen's dream! Over the last 40 years of family attention, forestry harvests have concentrated on creating animal habitat, and the land presently has respectable numbers of deer, coyotes, bear and turkeys, just to

  Donald Koelsch Deerfield Valley Real Estate

  4600 Augur Hole Rd, Marlboro, VT 05344
• 

  

  /40

  Est $435,896 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,038 Sq Ft

  67 Wilsons Woods Rd, Brattleboro, VT 05301

  67 Wilsons Woods Rd, 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
• 

  

  /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
• 

  

  /30

  Est $377,701 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,929 Sq Ft

  49 Marlboro Ave, Brattleboro, VT 05301

  49 Marlboro Ave, 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
• 

  

  /40

  $285,000 Sold May 09, 2025

  • 1,228 Sq Ft
  • $232/SF
  • 50 Days On Market

  • 2 Beds
  • 3.5 Baths
  • Built 1960

  2469 Augur Hole Rd, Guilford, VT 05301

  This charming Vermont bungalow is a work in progress, offering cozy charm and modern potential. Originally a three-bedroom plus loft home, the seller has opened two bedrooms to create a spacious en suite primary retreat. The inviting living room features a fireplace, perfect for chilly New England evenings, while the eat-in kitchen provides ample space for an island. A bright three-season room

  Patrice Schneider Southern Vermont Realty Group

  2469 Augur Hole Rd, Guilford, VT 05301
• 

  

  /24

  Est $495,573 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,592 Sq Ft

  89 Oak Grove Ave, Brattleboro, VT 05301

  89 Oak Grove Ave, Brattleboro, VT 05301
• 

  

  /37

  $1,499,000

  • 5 Beds
  • 4.5 Baths
  • 3,429 Sq Ft

  26 Springhill Rd, Dover, VT 05301

  This spectacular Post & Beam home is located just off the 13th hole of the Mount Snow Golf Course just minutes from the Mount Snow ski area. Nestled in a quiet community, with tremendous curb appeal, enjoy year round enjoyment thanks to the adjacent course, for obvious summer fun, but also snowshoeing and hiking in the winter. The interior of the home is about as good as it gets when looking for

  Adam Palmiter Berkley & Veller Greenwood/Dover

  26 Springhill Rd, Dover, 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /40

  Est $325,742 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,629 Sq Ft

  38 Borkowski Rd, Guilford, VT 05301

  38 Borkowski Rd, Guilford, VT 05301
• 

  

  /10

  $250,000

  • Land
  • 23 Acres
  • $10,823 per Acre

  184 Dupre Dr, Guilford, VT 05301

  Here's a large 23.10 +/- acre parcel that's mostly wooded but with a little bit of open field and possible short range local views. Conveniently located within a few minutes of town, here's an opportunity to enjoy country living while having access to modern amenities. There's a lot of potential for the right buyer! Please respect the privacy of the other houses on the road past this land.

  A.J. Bellville Bellville Realty

  184 Dupre Dr, Guilford, VT 05301

Showing Results 121 - 160, Page 4 of 18