Homes for Sale in 05301

/42
$849,000
- 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
/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
/27
$695,000
- 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
/27
$550,000
- 3 Beds
- 3 Baths
- 3,148 Sq Ft
672 E Orchard St, West Brattleboro, VT 05301

You can't beat this location, overlooking the Brattleboro Country Club golf course. This home was built circa 1919, and has many cool vintage features such as retro curved metal kitchen cabinets and baths. Generous rooms include a large living room with two field-stone fireplaces, a spacious family room. This is a 3 bedroom house with 3 full bathrooms, but it's really about how you configure

John Hatton Berkley & Veller Greenwood Country

672 E Orchard St, West Brattleboro, VT 05301
/60
$729,000
- 3 Beds
- 2 Baths
- 2,731 Sq Ft
49 Tyler St, Brattleboro, VT 05301

Rare opportunity to own this iconic Queen-Anne Victorian in Brattleboro’s coveted Tyler Street neighborhood. A remarkable and extremely rare blend of country and in-town living. Extraordinary and stunning views of the Connecticut River & Mount Wantastiquet. Lovingly cared for by the same owner for the past 29 yrs. This home sits proudly on the expansive 0.85-acre corner lot, in the core of

Dan Normandeau Berkley & Veller Greenwood Country

49 Tyler St, Brattleboro, VT 05301
/51
$949,000
- 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
/52
$525,000
- 3 Beds
- 2.5 Baths
- 2,023 Sq Ft
6940 Coolidge Hwy, Guilford, VT 05301

Located just north of the Massachusetts border, this home with two car detached garage is conveniently just 15 minutes from both Greenfield and Brattleboro.As you step inside to the mudroom you'll enter the coziest of kitchens radiating warmth and character. Featuring a wood stove, a stunning brick hearth with beehive oven, wooden beams adding rustic charm, while a cathedral ceiling keeps the

Rebecca Seymour Brattleboro Area Realty

6940 Coolidge Hwy, Guilford, VT 05301
/58
$650,000
- 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
/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
/20
$249,000
- 6 Beds
- 2 Baths
- 1,968 Sq Ft
14-16 Valley St, Brattleboro, VT 05301

Perfectly situated on a quiet street close to downtown, stores, and schools, this well cared for duplex is a rare opportunity for owner-occupants or investors alike. Each spacious unit offers 3 bedrooms and 1 full bath, with a host of updates and energy-efficient upgrades throughout. Many recent upgrades include Solar panels, Finished and insulated attics, Partially finished basements, Gas

Claire Renaud Berkley & Veller Greenwood Country

14-16 Valley St, Brattleboro, 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
/56
$235,000
- 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
/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
/18
$176,500
- 2 Beds
- 1 Bath
- 888 Sq Ft
15 Lynwood Dr, Brattleboro, VT 05301

This is absolutely NOT your ordinary Mobile Home! The original steel frame is the only remaining component of the mobile home. Completely rebuilt from the floor up with wood framing, windows, doors and insulation. This fully fenced leased lot has two sheds, a 1 car garage building with tons of storage and a workshop building with its own mini-split for heat and AC. The tastefully renovated

Chris Long BHG Masiello Brattleboro

15 Lynwood Dr, Brattleboro, VT 05301
/53
$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
/9
$80,250
- Land
- 3.10 Acres
- $25,887 per Acre
0 E Orchard St Unit 5047716, Brattleboro, VT 05301

A rare opportunity to purchase a lot in a highly desirable Brattleboro neighborhood. This 3+ acre wooded parcel features a mature pine forest with additional hardwoods intermixed, stonewalls and even a small stream. It's the location that makes this property unique. Just up the road from the Brattleboro Country Club on a quiet street that gives quick access to all that Brattleboro and the

Bill Hickok Berkley & Veller Greenwood Country

0 E Orchard St Unit 5047716, 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
/47
$299,000
- 3 Beds
- 1 Bath
- 1,222 Sq Ft
1082 W River Rd, Brattleboro, VT 05301

Welcome to 1082 West River Road — a peaceful, well-located gem just minutes from downtown Brattleboro. This charming home offers the perfect blend of convenience, outdoor space, and natural beauty. Set on a spacious lot with a large, open yard, there's room to garden, gather, or simply relax and enjoy the Vermont seasons. The private river access makes it easy to enjoy kayaking, swimming, or

Kate Barry EXP Realty

1082 W River Rd, Brattleboro, VT 05301
/24
$279,900
- 3 Beds
- 2 Baths
- 1,183 Sq Ft
4322 Augur Hole Rd, Brattleboro, VT 05301

Super location! Easy access to Rt 9 and Rt 30 but tucked into nearly a level acre in a lovely country setting. You can tell the previous occupants loved their gardens and a bit of work would restore the blooms to full glory. The pool is a bonus but is waiting for some care to get up and running...The home has emerged from a fun loving schoolhouse filled with learning and joy to a cozy,

Christine Lewis Brattleboro Area Realty

4322 Augur Hole Rd, Brattleboro, VT 05301
/58
$859,000
- 3 Beds
- 3.5 Baths
- 3,212 Sq Ft
104 Juniper Ridge Rd, Brattleboro, VT 05301

Welcome to Juniper Ridge! Where you will find superior craftsmanship, a private haven, and neighbors only one can dream of. As you enter the foyer of this custom built home, you'll feel its character & elegance with vaulted ceilings, arched doorways, terracotta tile and balconies lined with bookshelves. The home was built with attention to the flow, energy and natural light. The kitchen has

Kristen Ziter Taylor Brattleboro Area Realty

104 Juniper Ridge 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
$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
/42
$415,000
- 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
/5
$139,900
- Land
- 1.30 Acres
- $107,615 per Acre
00 Creamery Rd, Guilford, VT 05301

Just in time! Unbelievable! A high rolling meadow of your very own! Build the new home, the one you have been waiting for all your life, on this beautifully cared for sweet spot in the Vermont countryside community of Guilford. The boundaries are easy to find, one being right up to the edge of an old stone wall, the others marked with posts. Pick the high point and have a local view of old

Christine Lewis Brattleboro Area Realty

00 Creamery Rd, Guilford, 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
/41
$299,000
- 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
/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
$225,000
- 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
/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
/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
/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
/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
/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
/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
/5
$315,000
- 3 Beds
- 2.5 Baths
- 2,014 Sq Ft
412 Western Ave, Brattleboro, VT 05301

The cutest house on the block! Only 1 house from the famous deli for eats, right near the entrance to I 91, both north and south for travel or work and 2 minutes away from Memorial Park with all it offers....skating, ball games, pools, sliding, skiing. Plus it has a great back yard, 2 levels of decks and a front porch to add to the package. This 1860's Mansard is so sweet, filled with character

Christine Lewis Brattleboro Area Realty

412 Western Ave, Brattleboro, VT 05301
/12
$425,000
- 3 Beds
- 2 Baths
- 2,074 Sq Ft
36 Spruce St, Brattleboro, VT 05301

New Price! $25,000.00 price drop and a revised offering... If you saw this home before you want to take a second look! The 2nd floor is now vacant! ..and ready for owner occupancy. The basement, barn and lower building are empty and ready for all YOUR stuff. Plenty of undercover storage for boats, special vehicles or lots of other toys. A workshop? Home is just right for 2 family use or

Christine Lewis Brattleboro Area Realty

36 Spruce St, Brattleboro, VT 05301
/59
$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

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.