Homes in ZIP Code 05301

/19
$150,000 Sold Oct 17, 2025
- 700 Sq Ft
- $214/SF
- 18 Days On Market
- 1 Bed
- 1 Bath
- Built 1966
59 Brookside Dr Unit 8, Brattleboro, VT 05301

Low maintenance, affordable and desirable ground floor unit. Perched up high in Brookside development sits this cute efficient one bedroom condo. Inviting flow with a pass thru from the kitchen into the dining and the spacious living room has a great brand new slider out to your spacious level yard. Get creative and build a terrace to enjoy your summer evenings. The large bedroom with double

Angela Sherman Brattleboro Area Realty

59 Brookside Dr Unit 8, Brattleboro, VT 05301

/14
Est $231,014 Not Listed For Sale
- Studio
- 2 Baths
- 2,708 Sq Ft
202 Canal St, Brattleboro, VT 05301

202 Canal St, 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
/10
$180,100 Sold Oct 17, 2025
- 3,370 Sq Ft
- $53/SF
- 180 Days On Market
- 3 Beds
- 3 Baths
- Built 1830
148 Elliot St, Brattleboro, VT 05301

Spring Price Reduction! 3 One bedroom units and 4 single room occupancy units (SROs) w a shared bathroom and dishwashing area. Newer shingle roof on rear addition. The unfinished basement is spray foam insulated with a vapor barrier. Recent fire and safety inspection. Building needs a hands-on owner willing to take on some maintenance and improvements. Solid returns with opportunity to enhance

Steve Schoppmeyer BHG Masiello Brattleboro

148 Elliot St, Brattleboro, VT 05301

/38
Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,950 Sq Ft
773 Guilford St, Brattleboro, VT 05301

773 Guilford St, Brattleboro, VT 05301

/51
$425,000 Pending
- 4 Beds
- 2 Baths
- 2,445 Sq Ft
17 Tinker Hill Rd, Guilford, VT 05301

This one is the right one! So very special, nestled in the countryside just waiting.... So many options to choose from...a first floor main bedroom is perfect for aging in place, an x gen who still lives at home, in-law suite...or...perfect for an Air B&B. The other main bedroom features a walk out to the upper gardens, vaulted ceilings, room for a private getaway or reading nook. Plenty of

Christine Lewis Brattleboro Area Realty

17 Tinker Hill Rd, Guilford, VT 05301
/25
$210,000 Sold Oct 10, 2025
- 800 Sq Ft
- $262/SF
- 0 Days On Market
- 1 Bed
- 1 Bath
- Built 1944
402 Butternut Hill Rd, Guilford, VT 05301

Charming one-bedroom cottage sitting on a gentle hill with a lovely view of Wantastiquet. Located in Guilford, it presents the best of both worlds: a peaceful rural setting with quick access to all Brattleboro has to offer and to I-91N/S. The home offers a full kitchen, dining room, living-room and full-bath. The footprint of the 800-sq ft home provides surprisingly generous-sized rooms. New

Laura D'Angelo Berkley & Veller Greenwood Country

402 Butternut Hill Rd, Guilford, VT 05301

/40
Est $123,599 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

/40
$450,000 Pending
- 3 Beds
- 2.5 Baths
- 2,399 Sq Ft
10 Ethan Hill, Brattleboro, VT 05301

Tranquil Woodland Setting. Situated at the end of a peaceful neighborhood road, this classic Vermont-style cape has been thoughtfully designed to nestle perfectly within its forested lot. Experience the serenity of your own tree house in the woods, enjoying a country ambiance while still being conveniently close to Brattleboro’s amenities and I-91. Step into the efficiently arranged, fully

John Mcpherson Berkley & Veller Greenwood Country

10 Ethan Hill, Brattleboro, VT 05301
/28
$350,000 Sold Oct 06, 2025
- 1,768 Sq Ft
- $198/SF
- 31 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1950
177 Fairview St, Brattleboro, VT 05301

Ta Da! This is it! This diamond in the rough was built for the owner in 1950 and has been in the family ever since! The kitchen is huge, large enough for the traditional kitchen table, or a new kitchen island. True, it is vintage, but lots of cabinets and countertop for cooking and open to both living and dining for great parties. The living room is 26 ft long and room for everyone with big

Christine Lewis Brattleboro Area Realty

177 Fairview St, Brattleboro, VT 05301

/39
Est $300,261 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,206 Sq Ft
10 Jackson Rd, Guilford, VT 05301

10 Jackson Rd, Guilford, VT 05301

/27
$425,000 Under Contract
- 3 Beds
- 1.5 Baths
- 1,846 Sq Ft
16 Vermont Ave, Brattleboro, VT 05301

Vermont Avenue Gem! This stunning in-town Craftsman-style home is ideally located in a highly sought-after neighborhood. Just a short 1/4 mile to downtown, or in the opposite direction, the Marina and trails await. Boasting three bedrooms and 1.5 bathrooms, this home exudes charm with its exquisite woodwork, beautiful floors, and custom-built-ins throughout. Enjoy the abundance of natural light

Thomas Dahlin Berkley & Veller Greenwood Country

16 Vermont Ave, Brattleboro, VT 05301
/26
$714,000 Sold Oct 06, 2025
- 4,932 Sq Ft
- $145/SF
- 135 Days On Market
- 18 Beds
- 8 Baths
- Built 1900
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 2x1br A new owner can step into to this

Michael Gilman 3GEN Real Estate Inc

29 Canal St, Brattleboro, VT 05301

/36
Est $807,363 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,000 Sq Ft
19 S Belden Hill Rd, Guilford, VT 05301

19 S Belden Hill Rd, Guilford, VT 05301

/47
$499,000 Under Contract
- 4 Beds
- 4 Baths
- 2,372 Sq Ft
187 Hillwinds Rd, Brattleboro, VT 05301

Welcome home! The four bedroom home with dedicated office space is located in one of the area’s most desirable communities. Just minutes from Brattleboro, it offers the perfect blend of convenience, comfort, and outdoor living, with walking trails right nearby. The bright, open layout is ideal for everyday living and entertaining, featuring a welcoming kitchen, dining, and living area. A private

Claire Renaud Berkley & Veller Greenwood Country

187 Hillwinds Rd, Brattleboro, VT 05301
/60
$625,000 Sold Oct 03, 2025
- 2,731 Sq Ft
- $229/SF
- 65 Days On Market
- 3 Beds
- 2 Baths
- Built 1880
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

Karen Hoppe Berkley & Veller Greenwood Country

49 Tyler St, Brattleboro, VT 05301

/31
Est $272,188 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,335 Sq Ft
196 Randall Dr, Brattleboro, VT 05301

196 Randall Dr, Brattleboro, VT 05301

/32
$425,000 Under Contract
- 3 Beds
- 1.5 Baths
- 1,655 Sq Ft
155 Upper Dummerston Rd, Brattleboro, VT 05301

Great location! This 3-bedroom Colonial, built in 1920 (when houses were well-built) on Upper Dummerston Road is up the road from the Brattleboro Country Club and its golf course, cross country skiing, trails, and the West River. On a comfortable 0.75 level acres, this property is private but only 10 minutes from the center of town. Lots of windows bring in lots of light. Generous living room,

John Hatton Berkley & Veller Greenwood Country

155 Upper Dummerston Rd, Brattleboro, VT 05301
/42
$925,000 Sold Oct 01, 2025
- 4,150 Sq Ft
- $223/SF
- 5 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1983
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

/40
Est $604,261 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,075 Sq Ft
192 Lakeridge Rd, Guilford, VT 05301

192 Lakeridge Rd, Guilford, VT 05301

/60
$499,000 Under Contract
- 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
/50
$560,000 Sold Sep 30, 2025
- 1,658 Sq Ft
- $338/SF
- 5 Days On Market
- 4 Beds
- 2 Baths
- Built 1988
5134 Vermont 9, Brattleboro, VT 05301

Escape to this hidden gem with mountain views, 17 rolling acres,& featuring a rare blend of privacy, beauty, & income potential in the heart of southern Vermont. The contemporary main house offers clean lines, warm wood floors, & modern comforts, ideal for year-round living or a peaceful retreat. Expansive windows fill the rooms with natural light & frame the stunning surroundings. This 4

Tamara Purcell Berkley & Veller Greenwood Country

5134 Vermont 9, Brattleboro, VT 05301

/38
Est $437,840 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,398 Sq Ft
71 Great Blue Heron Dr, Guilford, VT 05301

71 Great Blue Heron Dr, Guilford, VT 05301

/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
/23
$266,000 Sold Sep 30, 2025
- 864 Sq Ft
- $308/SF
- 8 Days On Market
- 2 Beds
- 2 Baths
- Built 1942
45 Blakeslee St, Brattleboro, VT 05301

Charming Sun-Filled Cape on Corner Lot.This sweet and practical 2-bedroom, 2-bathroom Cape offers timeless appeal and everyday comfort on a sunny corner lot. Built in 1942, the home retains its original charm with 3-over-1 windows, built-ins throughout, and even a vintage ironing board cabinet. Inside, enjoy wood floors, a spacious eat-in kitchen with generous counter space, and a bright

Liz LaVorgna Berkley & Veller Greenwood Country

45 Blakeslee St, Brattleboro, VT 05301

/18
Est $343,321 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

/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
/54
$1,743,600 Sold Sep 30, 2025
- 8,718 Sq Ft
- $200/SF
- 274 Days On Market
- 7 Beds
- 7.5 Baths
- Built 2005
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

/37
Est $351,763 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

/17
$209,000
- 1 Bed
- 1 Bath
- 720 Sq Ft
75 Mather Rd, Brattleboro, VT 05301

Great Location, Great opportunity! Currently, a 1-bedroom, 1-bath home sits back on a desirable, pleasant country road. It is a larger lot than most, and with vision, here is an opportunity to start home ownership, downsize to a one-level with efficient living space. Use an investment or create your small Vermont getaway. This sweet spot is ready for your vision and ideas. This property is in

Kristen Ziter Taylor Brattleboro Area Realty

75 Mather Rd, Brattleboro, VT 05301
/50
$659,000 Sold Sep 29, 2025
- 1,600 Sq Ft
- $412/SF
- 4 Days On Market
- 3 Beds
- 2 Baths
- Built 2018
86 Stark Rd, Brattleboro, VT 05301

This property is a fine example of a labor of love by it's owner; he built everything from the literal ground, up. There are 3 bedrooms and 2 full baths, including a primary bedroom with ensuite, as well as a loft and a massive bonus room. You'll congregate around the granite countertops while cooking amidst the cathedral ceiling and fireplace ambiance. There's an abundance of things to love

Victoria Woods Brattleboro Area Realty

86 Stark Rd, Brattleboro, VT 05301

/39
Est $761,986 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

/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
/34
$310,000 Sold Sep 26, 2025
- 1,025 Sq Ft
- $302/SF
- 8 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1972
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

/19
Est $360,821 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,351 Sq Ft
1190 Stage Rd, Guilford, VT 05301

1190 Stage Rd, Guilford, 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
/27
$470,000 Sold Sep 26, 2025
- 3,148 Sq Ft
- $149/SF
- 49 Days On Market
- 3 Beds
- 3 Baths
- Built 1919
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

/40
Est $454,106 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,190 Sq Ft
98 Jelly Mill Rd, Guilford, VT 05301

98 Jelly Mill 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
/34
$399,000 Sold Sep 26, 2025
- 2,190 Sq Ft
- $182/SF
- 92 Days On Market
- 3 Beds
- 2 Baths
- Built 1997
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

Showing Results 41 - 80, Page 2 of 18

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