Homes for Sale in 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
$499,000
- 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
/3
$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
/33
$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
/33
$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
/44
$475,000
- 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
/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
/60
$499,000
- 3 Beds
- 2.5 Baths
- 3,415 Sq Ft
23 Meeting House Ln, Brattleboro, VT 05301

First Time on the Market – Premier Brattleboro Location!Nestled on one of the most desirable lots in one of Brattleboro’s finest neighborhoods, this well-maintained home is being offered for sale for the very first time! Custom-built by the current owner in 1970 with attention to detail, this spacious ranch offers comfort, functionality, and an impressive list of amenities.Perfect for

Bert Inman RE/MAX Town & Country

23 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
/49
$475,000
- 3 Beds
- 3 Baths
- 2,463 Sq Ft
1591 Higley Hill, Marlboro, VT 05344

Wonderful home on 11.2 acres in a peaceful setting on Higley Hill in Marlboro. The main level boasts a beautiful family room addition with lots of windows and a gas fireplace, galley kitchen with stainless appliances, dining area, 3/4 bath with laundry, living room with gas stove, 3/4 bath with sitting area and a primary bedroom with ensuite full bath. A loft area that can be used as a bedroom or

Jennifer Hovey-Densmore Deerfield Valley Real Estate

1591 Higley Hill, Marlboro, VT 05344
/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
/58
$515,000
- 4 Beds
- 2 Baths
- 3,090 Sq Ft
301 Maple St, Brattleboro, VT 05301

Fall is here! The leaves are turning, the mums are in cheerful blooming mode and soon it will be time to cozy in with the woodstove! But...not quite yet, there are still plenty of days for the sun filled deck, blooms galore and strolls around your own private gardens. This sweet home has the great construction of the 1800's...loved and cared for by generations of Vermonters who have added,

Christine Lewis Brattleboro Area Realty

301 Maple St, Brattleboro, VT 05301
/21
$149,000
- Land
- 0.39 Acre
- $382,051 per Acre
19 Western Ave, Brattleboro, VT 05301

Location, Location, Location.... This level Sunny lot has enough frontage on both Acorn Lane and Western Ave to build a home. Seller's have put in systems: main water & sewer connections, as well as 200 amp electric in place and have them located in the shed for easy access for your new construction. The photos show the work they did to bring up the water/sewer and electric from the street.

Mary M. Wallace Berkley & Veller Greenwood Country

19 Western Ave, Brattleboro, VT 05301
/38
$359,000
- 2 Beds
- 1.5 Baths
- 1,321 Sq Ft
257 Partridge Rd, Guilford, VT 05301

Beautiful north and westerly views! This sweet 2-bedroom, 2-bath, low maintenance home with a 2-car garage was built in 2004 and handsomely sits perched atop of a gentle hill and overlooks the rolling knolls and the pretty fields below. A stone's throw to the historic Guilford Store and Cafe- have your morning coffee and muffin there, at your kitchen table or out on your side deck overlooking

Stephanie Peduzzi-Baker Brattleboro Area Realty

257 Partridge Rd, Guilford, VT 05301
/59
$335,000 Open Sat 10AM - 12PM
- 3 Beds
- 2 Baths
- 1,728 Sq Ft
290 Guilford St, Brattleboro, VT 05301

This meticulously maintained 3-bedroom, 2-bath ranch surprises with its spacious layout and thoughtfully designed interior. The kitchen is a dream for those who love to cook, featuring quartz countertops, slate flooring, solid hardwood soft-close cabinetry, a dedicated baking station, and access to the nearly 700 sq. ft. back deck—perfect for entertaining. The open main living area features

Kate Barry EXP Realty

290 Guilford St, Brattleboro, VT 05301
/17
$110,000
- Land
- 22.6 Acres
- $4,867 per Acre
215 Melendy Hill Rd, Guilford, VT 05301

Just past the Guilford Store and a short drive up Melendy Hill Rd sits this 23.60+/- acres of forest land. This wonderful property offers 2 delightful brooks, Broad Brook to the west and north and a smaller brook that’s closer to Melendy Hill Rd. The parcel features a mixed forest consisting of large stands of pine and hemlock with the east side offering a good mix of hardwoods. Great views

Bill Hickok Berkley & Veller Greenwood Country

215 Melendy Hill Rd, Guilford, 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
/26
$175,000
- Land
- 19.4 Acres
- $9,021 per Acre
2610 Lower Dover Rd, Marlboro, VT 05344

Marlboro Sanctuary – Private Meadow Retreat. Discover this beautiful and private parcel in the heart of Marlboro, featuring an open meadow with sunny southern exposure. With generous road frontage and easy access between two charming stonewalls, a well-maintained old logging road leads you into the property. Along the way, pass by a small pond site before arriving at the expansive meadow, framed

Monique White Deerfield Valley Real Estate

2610 Lower Dover Rd, Marlboro, VT 05344
/24
$425,000
- 5 Beds
- 3 Baths
- 2,254 Sq Ft
85 Stockwell Dr, Brattleboro, VT 05301

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 downtown, to

Christine Lewis Brattleboro Area Realty

85 Stockwell Dr, Brattleboro, VT 05301
/30
$345,000
- 3 Beds
- 2.5 Baths
- 1,890 Sq Ft
91 Sunny Acres Rd, Brattleboro, VT 05301

You will appreciate this bright and light, very well kept, in-town home on .22 acre.The open concept feel on the main floor smoothly incorporates the kitchen, dining and living spaces. You'll absolutely love cooking in the updated kitchen with granite countertops/island, attractive GE appliances and soft-close cabinetry. The dining area has a French door leading to the large private back deck,

Stephanie Peduzzi-Baker Brattleboro Area Realty

91 Sunny Acres Rd, 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
$385,000
- 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
/36
$424,500
- 4 Beds
- 3.5 Baths
- 2,794 Sq Ft
87 Orchard St, Brattleboro, VT 05301

Charming home located on desirable Orchard Street, just minutes from I-91 for easy commuting. Whether you want to wander the woods, paddle local waterways, hit the links, or ride the slopes you have multiple wonderful options nearby. This spacious home features four large bedrooms, three full bathrooms, and an open living concept perfect for entertaining. Beautiful flower gardens welcome you

Jim Bellville Bellville Realty

87 Orchard St, Brattleboro, VT 05301
/29
$325,000
- 4 Beds
- 2 Baths
- 2,408 Sq Ft
78-80 Central St, Brattleboro, VT 05301

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, light-filled

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
/25
$189,000
- 2 Beds
- 1 Bath
- 1,000 Sq Ft
22 Chestnut St Unit 1, Brattleboro, VT 05301

Welcome to 22 Chestnut Street, Unit #1 — a charming and fully furnished first-floor condo nestled in the lovely Chestnut Street neighborhood. This spacious 2-bedroom, 1-bath unit features a thoughtfully updated bathroom with a clawfoot tub and separate shower, a cozy mudroom entryway, and a sunny side porch that conveys with the unit — perfect for morning coffee or evening relaxation. The kitchen

Erica Reynolds Southern Vermont Realty Group

22 Chestnut St Unit 1, Brattleboro, 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
/10
$175,000
- Land
- 8 Acres
- $21,875 per Acre
680 W River Rd, Brattleboro, VT 05301

8 acres only 2 miles from Brattleboro situated across the road from the West River. Existing gated gravel driveway is in. Gravel on site and road roughed into a high plateau with designs for SIX 1-2 bedroom cottages. Topographical survey, septic design plans and other existing engineering are complete which make this an attractive option for someone looking to develop a parcel into a cottage

Chris Long BHG Masiello Brattleboro

680 W River Rd, Brattleboro, 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
/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
$319,900
- 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

Christine Lewis Brattleboro Area Realty

164 Chestnut St, Brattleboro, VT 05301

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