Homes for Sale in 05301

• 

  

  

  /42

  $574,900

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft

  555 Vermont 9, Wilmington, VT 05363

  Welcome to your dream home in the heart of Southern Vermont. This brand-new construction 3-bedroom, 2-bath residence seamlessly blends modern comfort with classic Vermont charm, perfect for year-round living or a weekend escape. Enjoy a spacious, open-concept layout filled with natural light, enhanced by high-quality Anderson windows and doors. The kitchen boasts brand new appliances, while the

  Flex Realty Group Flex Realty

  555 Vermont 9, Wilmington, VT 05363
• 

  

  

  /23

  $500,000

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft

  137 Pleasant Valley Rd, Brattleboro, VT 05301

  This is IT! If you are looking for an incredible small home...not tiny...but compact and just the right size, this is it. Timber framing at it's best gives you an open concept, live in every inch, light filled, high quality charming home. Nestled in a wildflower meadow, with plenty of room for a homestead garden, enough open sky for stargazers, big and flat enough for your own cross country ski

  Christine Lewis Brattleboro Area Realty

  137 Pleasant Valley Rd, Brattleboro, VT 05301
• 

  

  

  /44

  $599,000

  • 4 Beds
  • 4 Baths
  • 4,060 Sq Ft

  141 Piney Brook Way, Brattleboro, VT 05301

  Set on 12 acres of wooded privacy in desirable Marlboro, this spacious and versatile property offers comfort, flexibility, and stunning natural surroundings. The main home features 3 bedrooms, a large family room and first-floor laundry, offering plenty of room for a growing household, guests, or multi-generational living. Cozy up by the wood stove on chilly evenings, and enjoy the peace of mind

  Desiree Stango Berkley & Veller Greenwood Country

  141 Piney Brook Way, Brattleboro, VT 05301
• 

  

  

  /41

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft

  216 Ghastly Job Way, Wilmington, VT 05363

  Vermont mountain getaway perched on a private parcel at the end of a quiet country road, this charming mountain retreat offers sweeping long-range views spanning from the Green Mountains within the National Forest north to Mount Snow and east toward neighboring Marlboro. Enjoy breathtaking sunsets from the covered front porch or relax in the outdoor hot tub surrounded by nature. Inside, the

  Monique White Deerfield Valley Real Estate

  216 Ghastly Job Way, Wilmington, VT 05363
• 

  

  

  /36

  $479,000

  • 4 Beds
  • 2.5 Baths
  • 1,887 Sq Ft

  230 Western Ave, Brattleboro, VT 05301

  This beautifully renovated in-town home blends character, comfort, and convenience. From the welcoming front porch to the shaded backyard and new deck, every space has been thoughtfully updated. The sunny kitchen offers granite countertops, stainless steel appliances, and a well-planned pantry, while the living room is anchored by a handsome Italian pellet stove; efficient, warm, and the perfect

  John Hatton Berkley & Veller Greenwood Country

  230 Western Ave, Brattleboro, VT 05301
• 

  

  /32

  $560,000

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft

  162 Buttonwood Dr, Brattleboro, VT 05301

  BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

  Dan Normandeau Berkley & Veller Greenwood Country

  162 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  /34

  $585,000

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft

  24 Dogwood Dr, Brattleboro, VT 05301

  BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

  Dan Normandeau Berkley & Veller Greenwood Country

  24 Dogwood Dr, Brattleboro, VT 05301
• 

  

  /32

  $585,000

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft

  161 Buttonwood Dr, Brattleboro, VT 05301

  BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

  Dan Normandeau Berkley & Veller Greenwood Country

  161 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  /39

  $625,000

  • 5 Beds
  • 4 Baths
  • 3,748 Sq Ft

  58 Oak St, Brattleboro, VT 05301

  Come experience the elegance and charm of this stunning in-town retreat! Close to the town common and vibrant downtown Brattleboro—home to fine dining, galleries, quaint shops, and live music venues. Step inside the main house and be welcomed by a country kitchen featuring a large island, ideal for gatherings. The home exudes Victorian character with soaring ceilings, hardwood floors, and

  Rebecca Seymour Brattleboro Area Realty

  58 Oak St, Brattleboro, VT 05301
• 

  

  /37

  $849,000

  • 4 Beds
  • 4 Baths
  • 3,600 Sq Ft

  5 Hillwinds N, Brattleboro, VT 05301

  Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on 11 acres of landscaped grounds with lawns, stone walls, gardens, and woodland in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through a covered porch that opens into a marble floored foyer

  Robert Doyle Berkley & Veller Greenwood Country

  5 Hillwinds N, Brattleboro, VT 05301
• 

  

  /58

  $568,000

  • 3 Beds
  • 2 Baths
  • 2,066 Sq Ft

  192 Western Ave, Brattleboro, VT 05301

  Timeless 1855 classic with historic charm just minutes to downtown Brattleboro. Step back in time with this beautifully preserved home, offering a rare blend of vintage character and modern comfort. Featuring three bedrooms and two bathrooms, this home is perfect for those who appreciate craftsmanship and history. Thoughtful updates complement the historic features without compromising

  Claire Renaud Berkley & Veller Greenwood Country

  192 Western Ave, Brattleboro, VT 05301
• 

  

  /30

  $629,000

  • 4 Beds
  • 2 Baths
  • 2,656 Sq Ft

  204 Meeting House Ln, Brattleboro, VT 05301

  Your Dream Home Awaits on Meetinghouse Lane! Nestled in the desirable and quiet neighborhood of Meetinghouse Lane, this contemporary home offers both privacy & charm. Surrounded by mature trees, the property feels like a peaceful retreat, while still being conveniently located. A paved driveway leads to an oversized two-car garage, connected to the house by a convenient breezeway. The expansive

  Desiree Stango Berkley & Veller Greenwood Country

  204 Meeting House Ln, Brattleboro, 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
• 

  

  /58

  $515,000

  • 4 Beds
  • 2 Baths
  • 3,090 Sq Ft

  301 Maple St, Brattleboro, VT 05301

  Sweet! It is starting to get chilly, we remember the oversized salt water pool fun and the summer heat on tanned skin, coming again in the spring. The flowers and shrubs will sing again next season, but for now, we get to love the hardscape that comes to life catching flakes and creating breathtaking sculptures that glitter and change as we watch. It is the season for snuggling in, all toasty and

  Christine Lewis Brattleboro Area Realty

  301 Maple St, Brattleboro, VT 05301
• 

  

  /28

  $285,000

  • 2 Beds
  • 1 Bath
  • 903 Sq Ft

  1555 W River Rd, Dummerston, VT 05301

  Open House 11/15 - 12pm-2pm Welcome home to this inviting 2-bedroom, 1-bath Cape on scenic West River Road. Perfectly located just a short drive to downtown Brattleboro’s shops, restaurants, and local conveniences—just over a quarter mile to West River Park and about 30 minutes to Mount Snow—this home offers the ideal blend of country charm and everyday comfort. Set on a beautiful .6-acre lot

  Morriah Adams BHG Masiello Brattleboro

  1555 W River Rd, Dummerston, VT 05301
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  /8

  $52,000

  • Land
  • 6.1 Acres
  • $8,525 per Acre

  0 Cooke Rd, Brattleboro, VT 05301

  Amidst rolling VT farmland, sits these 6 acres in West Brattleboro. While there is road frontage on Rte 9, the driveway is off the class 4 section of Cooke Rd. There's about 250 feet of Cooke Rd that you would need to maintain before the town road. The ROW into the land parallels the power lines, which you cannot see when you're on the land. There a nice cleared shelf when you walk in and then

  Victoria Woods Brattleboro Area Realty

  0 Cooke Rd, Brattleboro, VT 05301
• 

  

  /12

  $165,000

  • Land
  • 16.48 Acres
  • $10,012 per Acre

  1854 Vermont 9, Marlboro, VT 05344

  Escape to Nature – 16.48-Acre Glampsite with Cozy Cabins and Endless Potential Discover your private retreat on 16.48 serene wooded acres featuring two comfortably appointed sleeping cabins, each offering electricity, electric fireplaces for year-round comfort, and the possibility of internet. Enjoy modern convenience in a natural setting, with facilities for cooking and showering already onsite.

  Kristen Breeden Southern Vermont Realty Group

  1854 Vermont 9, Marlboro, VT 05344
• 

  

  /19

  $190,000

  • 2 Beds
  • 1 Bath
  • 930 Sq Ft

  39 Brookside Dr Unit 3, 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 bathroom

  Angela Sherman Brattleboro Area Realty

  39 Brookside Dr Unit 3, Brattleboro, VT 05301
• 

  

  /24

  $29,900

  • 2 Beds
  • 1 Bath
  • 684 Sq Ft

  97 Glen St, Brattleboro, VT 05301

  Finally!! Affordable!! This just right sized home is tucked into the 55 and older park for peace and quiet. Along the brook, the damaged homes have been removed and replaced with open green space with a gentle park like feel. There is an awning over the stairs, an added pitched roof, spacious front end kitchen/dining with several windows and some built-ins. Located in one of the 3 parks, making

  Angela Sherman Brattleboro Area Realty

  97 Glen St, Brattleboro, VT 05301
• 

  

  /54

  $1,400,000

  • 5 Beds
  • 4.5 Baths
  • 4,908 Sq Ft

  131 Stark Rd, Brattleboro, VT 05301

  Remember when you were 6 and the Hundred Acre Wood seemed as big as the whole world? Now is the time to write your own story...and live in your own Hundred Acre Wood....only this one is grown up with 103 acres, 35 acres of open meadow, about 1/4 mile bordering the Whetstone Brook, a great barn, nearly 4000 square feet of living space and so many stories to live! With a perfect

  Christine Lewis Brattleboro Area Realty

  131 Stark Rd, Brattleboro, VT 05301
• 

  

  /24

  $365,000

  • 5 Beds
  • 3 Baths
  • 2,254 Sq Ft

  85 Stockwell Dr, Brattleboro, VT 05301

  Motivated Seller! Sweet! This 5 bedroom /3 bath home is located in one of our most sought after neighborhoods, is newly remodeled, has 2 pellet stoves for economical heat and a nice back deck. Lots of opportunities to garden, relax in a hammock or play with pets. Flexible floor plan is perfect for at home workers, multigenerational living and aging in place. Hop the MOOVER and take a ride

  Christine Lewis Brattleboro Area Realty

  85 Stockwell Dr, Brattleboro, VT 05301
• 

  

  /60

  $415,000

  • 6 Beds
  • 2 Baths
  • 2,048 Sq Ft

  58-60 Frost Place, Brattleboro, VT 05301

  OPEN HOUSE 11/13 4-5:30PM This turnkey income generator is now move in ready! One side is vacant and ready for your plans, the other has a successful Airbnb rental history and was completely renovated in 2018. Both have in-unit washer/dryer/ hook up. Enter through the thoughtfully crafted mudroom with generous built-in storage. The open-concept kitchen, dining, and living areas create an inviting

  Lily Gautot Greenwald Realty Group

  58-60 Frost Place, Brattleboro, VT 05301
• 

  

  /60

  $5,900,000

  • 4 Beds
  • 8 Baths
  • 16,736 Sq Ft

  1950 Collins Rd, Brattleboro, VT 05301

  Exceptional 177+ Acre Estate with Luxury Log Home, Event Venue & Craft Beverage Facilities. Experience unmatched luxury and opportunity on this remarkable 177+ acre estate. Featuring an 8,000+ sq ft timber frame log home, a 7,100 sq ft finished event venue, and on-site winery, craft brewery, and champagne-making facilities, this turn-key property is ideal as a private residence, retreat, or

  Margretta Fischer Wohler Realty Group

  1950 Collins Rd, Brattleboro, VT 05301
• 

  

  /30

  $369,000

  • 3 Beds
  • 2 Baths
  • 1,703 Sq Ft

  1089 Marlboro Rd, Brattleboro, VT 05301

  The one you have been waiting for! This traditional New England cape with a twist checks all the boxes! Remodeled in the 90's, it has a cook's delight for a kitchen with tons of cabinets and lots of countertops for baking prep...cookies and breads are a must!. The first floor was expanded to almost double the size of the living room, adding a fireplace and a main bedroom. Aging in place is easy

  Christine Lewis Brattleboro Area Realty

  1089 Marlboro Rd, Brattleboro, VT 05301
• 

  

  /44

  $425,000

  • 4 Beds
  • 3 Baths
  • 3,314 Sq Ft

  76 Spruce St, Brattleboro, VT 05301

  Sweet! The perfect location...intown...backing up to the retreat trail system...and has a beautiful front porch and private back deck. This has been a much loved home, ready for a new generation to create their own music and harmony of life. The rooms are large, comfortable with lots of windows, real wood paneling reflecting the era, high ceilings, enough room to work from home (even an office

  Christine Lewis Brattleboro Area Realty

  76 Spruce St, Brattleboro, VT 05301
• 

  

  /29

  $310,000

  • 4 Beds
  • 2 Baths
  • 2,408 Sq Ft

  78-80 Central St, Brattleboro, VT 05301

  MOTIVATED SELLER: Charming Two-Unit Multi-Family on Quiet In-Town Street – Ideal for Investors or Owner-Occupants! Tucked away on a peaceful side street yet just minutes from shopping, dining, and public transportation, this two-family property offers the perfect blend of convenience and comfort. The current owners have updated all the electrical in both units. Each unit features spacious,

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  78-80 Central St, Brattleboro, VT 05301
• 

  

  /39

  $585,000

  • Land
  • 67.63 Acres
  • $8,650 per Acre

  932 Middle Rd, Dummerston, VT 05301

  Discover the perfect blend of peace, privacy, and potential on this 67.63-acre privately owned parcel of land. Nestled in a scenic and serene setting, this expansive property is a rare opportunity to build your dream home, estate, or getaway retreat. Two picturesque ponds – ideal for fishing, wildlife watching, or just enjoying the view. The main home site has amazing mountain views and sits

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  932 Middle Rd, Dummerston, VT 05301
• 

  

  /20

  $279,900

  • 4 Beds
  • 2 Baths
  • 1,733 Sq Ft

  1177 Western Ave, Brattleboro, VT 05301

  So much to offer! This 4 bedroom 2 bath has plenty of room for all! It features a large kitchen with lots of counter space and the laundry tucked in for easy access while you cook and bake. The deck overlooks the lower yard where the solar panels live and the perfect spot for the above ground swimming pool (needs a liner). Huge lot, lots of off street parking and on the MOOVER line for non

  Christine Lewis Brattleboro Area Realty

  1177 Western Ave, 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
• 

  

  /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
• 

  /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
• 

  /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
• 

  

  /16

  $259,900

  • Land
  • 29.2 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
• 

  

  /38

  $1,750,000

  • 4 Beds
  • 3.5 Baths
  • 2,862 Sq Ft

  161 Depot Rd, Williamsville, VT 05362

  Perched high above the enchanting hills of Newfane, VT, lies a truly one-of-a-kind property. This meticulously crafted home offers an off-grid, private retreat with breathtaking views of the surrounding landscape. Constructed in 2003, the post and beam design incorporates wood and stone harvested from its expansive219-acre setting, showcasing a harmonious blend of nature and architecture. This

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  161 Depot Rd, Williamsville, VT 05362
• 

  

  /11

  $250,000

  • Land
  • 18 Acres
  • $13,889 per Acre

  0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301

  Tucked in the gently rolling hills of Vermont, this is a sweet spot to build your new home. Located on a class 3 privately maintained road, there are power poles the length of the road with fiber optics ready for the streamers or work at home folks. Build on the road for a short drive and utility ease, or take the secluded route and tuck away in the forest. The acreage is an educated guess and

  Christine Lewis Brattleboro Area Realty

  0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301
• 

  

  /51

  $899,800

  • 5 Beds
  • 8 Baths
  • 7,430 Sq Ft

  925 Hinesburg Rd, Brattleboro, VT 05301

  Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

  Christine Lewis Brattleboro Area Realty

  925 Hinesburg Rd, Brattleboro, VT 05301
• 

  

  /60

  $895,000

  • 3 Beds
  • 3 Baths
  • 2,258 Sq Ft

  266 Ursa Ridge Rd, Dummerston, VT 05301

  This home is living art, tucked away at the end of the road of lovely homes & hundreds of acres ridgetop, yet only 10 minutes from downtown Brattleboro. Built by a craftsman this home is gracious & energy efficient. Building materials have been harvested from it's 51-1/2 acre woodland. Rooms are thoughtfully designed awash with natural light. Walk up the covered, stone walkway to enter the

  Randi Ziter Brattleboro Area Realty

  266 Ursa Ridge Rd, Dummerston, VT 05301
• 

  

  /18

  $309,900

  • 3 Beds
  • 1 Bath
  • 1,323 Sq Ft

  164 Chestnut St, Brattleboro, VT 05301

  Just right for new beginnings! This raised ranch affords the new home buyer a cozy place to start with a big, level yard with lots of flowering shrubs to look pretty when you drive up, and a perfect spot for ball in the back! The dead end street is a bit safer for bikes and strolls than others and creates a nice comfortable neighborhood for smiling greetings. With an eat in kitchen with sliders

  Christine Lewis Brattleboro Area Realty

  164 Chestnut St, Brattleboro, VT 05301
• 

  

  /48

  $380,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 1.5 Baths
  • 2,433 Sq Ft

  183 Bear Hill Rd, Dummerston, VT 05301

  Discover a hidden gem nestled deep in the woods—a rustic retreat that’s entirely off-grid and 100% solar powered. Perfect for nature lovers, creative spirits, or anyone seeking serenity and self-sufficiency. This one-of-a-kind property features a charming main house with a two-bedroom loft attached, currently used for short-term rentals. The main cabin exudes classic Adirondack charm with

  Kate Barry EXP Realty

  183 Bear Hill Rd, Dummerston, VT 05301
• 

  

  /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

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