Homes in ZIP Code 05301

• 

  

  

  /32

  Est $359,923 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,614 Sq Ft

  36 Chestnut St, Brattleboro, VT 05301

  36 Chestnut St, Brattleboro, VT 05301
• 

  

  

  /60

  $289,900 Pending

  • 5 Beds
  • 4 Baths
  • 2,579 Sq Ft

  11 Culbertson Dr, Brattleboro, VT 05301

  Located in the heart of Brattleboro walking distance to the farmer’s market and the expansive Living Memorial Park, this unique home has many options. Open up one doorway and it could be a 4 bedroom home plus an in-law studio. Or, keep it as 3 separate units – a 3 bedroom home, 1 bedroom apartment, and a very large and elegant studio apartment. It currently functions as an active Air BnB and

  Lisa Friedman Great American Dream Realty

  11 Culbertson Dr, Brattleboro, VT 05301
• 

  

  

  /11

  $165,000 Sold Jun 06, 2025

  • Land
  • 69.7 Acres
  • $2,367 per Acre

  • 26 Days On Market

  575 Collins Rd, Halifax, VT 05301

  Tucked away nearly 1,000 feet from the quiet, town-maintained Collins Road, this exceptional 70-acre parcel offers complete privacy and endless potential. 5 Acres have been removed for the house lot from the Current Use Program. A mix of serene woodlands, open space ideal for building, and a peaceful babbling brook at the rear of the property create a picturesque setting for your dream home or

  Monica Sumner BHG Masiello Brattleboro

  575 Collins Rd, Halifax, VT 05301
• 

  

  

  /36

  Est $307,469 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,388 Sq Ft

  122 Frost St, Brattleboro, VT 05301

  122 Frost St, Brattleboro, VT 05301
• 

  

  

  /54

  $2,189,000 Pending

  • 7 Beds
  • 7.5 Baths
  • 8,718 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
• 

  

  /22

  $67,000 Sold Jun 06, 2025

  • 1,224 Sq Ft
  • $55/SF
  • 14 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1978

  89 Glen St, West Brattleboro, VT 05301

  This single wide has so many added benefits! You can heat entirely with wood should you choose, there's an entryway and a huge heated mudroom, with direct access to the expansive back yard. The corner lot overlooks neighboring grassy fields for additional privacy. This yard has raised beds and over 200 bulbs planted!Being sold with a solar generator that powers the owners' home office.Contingent

  Victoria Woods Brattleboro Area Realty

  89 Glen St, West Brattleboro, VT 05301
• 

  

  /23

  Est $297,790 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,611 Sq Ft

  204 Williams St, Brattleboro, VT 05301

  204 Williams St, Brattleboro, VT 05301
• 

  

  /50

  $659,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  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
• 

  

  /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

  70 Greenleaf St, Brattleboro, VT 05301
• 

  

  /35

  Est $368,977 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,488 Sq Ft

  25 Strand Ave, Brattleboro, VT 05301

  25 Strand Ave, Brattleboro, VT 05301
• 

  /2

  $90,000 Pending

  • 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
• 

  

  /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
• 

  

  /29

  Est $552,751 Not Listed For Sale

  • 3 Beds
  • 4.5 Baths
  • 3,913 Sq Ft

  300 Western Ave, Brattleboro, VT 05301

  300 Western Ave, Brattleboro, VT 05301
• 

  

  /50

  $575,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,658 Sq Ft

  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
• 

  

  /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
• 

  

  /17

  Est $404,905 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,519 Sq Ft

  103 New England Dr, Brattleboro, VT 05301

  103 New England Dr, Brattleboro, VT 05301
• 

  

  /25

  $269,000 Pending

  • 5 Beds
  • 4 Baths
  • 2,376 Sq Ft

  50 Grove St, Brattleboro, VT 05301

  New to the market, this well-maintained 3-unit property is a fantastic opportunity for both investors and owner-occupants. Located just minutes from downtown, it offers convenience, value, and flexibility. One unit is currently on a month to month and move-in ready, making it ideal for someone looking to live on-site or set their own rental terms. The other two units are occupied by long-term,

  Kate Barry EXP Realty

  50 Grove St, Brattleboro, 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
• 

  

  /37

  Est $310,770 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,341 Sq Ft

  625 Western Ave, Brattleboro, VT 05301

  625 Western Ave, Brattleboro, VT 05301
• 

  

  /42

  $849,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,150 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
• 

  

  /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
• 

  

  /33

  Est $402,339 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,716 Sq Ft

  55 Thayer Ridge Rd, Brattleboro, VT 05301

  55 Thayer Ridge Rd, Brattleboro, VT 05301
• 

  

  /20

  $420,000 Pending

  • Land
  • 106 Acres
  • $3,962 per Acre

  2745 Bonnyvale Rd, Guilford, VT 05301

  This property is arguably one of the most extraordinary pieces of land of its size in southeastern Vermont. With 106+- acres; The view from the top of the 6-acre field is nothing short of spectacular with sweeping extensive views & beautiful sunsets. Peace and tranquility abound. Nature abounds here, with the northern property line marked by an ancient, magnificent stone wall that separates

  Mary M. Wallace Berkley & Veller Greenwood Country

  2745 Bonnyvale 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
• 

  

  /17

  Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,192 Sq Ft

  124 Green St, Brattleboro, VT 05301

  124 Green St, Brattleboro, VT 05301
• 

  

  /33

  $235,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 2,112 Sq Ft

  116 Morningside Commons, Brattleboro, VT 05301

  Yes! A coveted first floor single level unit! And not only that but an end unit, sweetly tucked away for privacy! Just follow the tree and flower lined path right to your door!2 bedrooms, one ensuite, with an additional bedroom, bath, large eat in kitchen, living room, and a stackable washer/dryer, all on the first floor! There are only a few condos here that have finished basement space and

  Rebecca Seymour Brattleboro Area Realty

  116 Morningside Commons, 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
• 

  

  /20

  Est $272,148 Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 2,150 Sq Ft

  173 Green St, Brattleboro, VT 05301

  173 Green St, Brattleboro, VT 05301
• 

  

  /38

  $395,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 2,715 Sq Ft

  105 Chestnut St, Brattleboro, VT 05301

  This authentic and updated Vermont home is situated on welcoming, dead-end street surrounded by woods on two sides creating a feeling of peacefulness and connection with nature. How fortunate to live in town but also have the calming surroundings of mature plantings, opportunity to garden and de-stress in your private sanctuary. Enjoy outdoor dining on the deck, located just off the dining

  Kristen Ziter Taylor Brattleboro Area Realty

  105 Chestnut 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
• 

  

  /18

  Est $305,364 Not Listed For Sale

  • 7 Beds
  • 3 Baths
  • 3,540 Sq Ft

  108 High St, Brattleboro, VT 05301

  108 High St, Brattleboro, VT 05301
• 

  

  /14

  $249,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft

  70 Arbor Hill Commons Unit 15, Brattleboro, VT 05301

  Beautifully elegant light filled condo in Bluebell Building at Arbor Hill. An abundance of windows throughout creates a magical light filled environment that includes hardwood flooring, a Great Room providing space for Living, Dining and Kitchen, 2 spacious Bedrooms, 2 Full Baths, Entry w/ double closet and Laundry/Pantry. The Primary Bedroom has an en suite Bath, mini split and a large walk-in

  Robert Doyle Berkley & Veller Greenwood Country

  70 Arbor Hill Commons Unit 15, Brattleboro, VT 05301
• 

  

  /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
• 

  

  /27

  Est $408,180 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,994 Sq Ft

  22 Howard St, Brattleboro, VT 05301

  22 Howard St, Brattleboro, VT 05301
• 

  

  /23

  $249,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  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
• 

  

  /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
• 

  

  /40

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,628 Sq Ft

  43 Williston St, Brattleboro, VT 05301

  43 Williston St, Brattleboro, VT 05301
• 

  

  /34

  $299,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,025 Sq Ft

  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
• 

  

  /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
• 

  

  /40

  Est $676,418 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,137 Sq Ft

  43 Tyler St, Brattleboro, VT 05301

  43 Tyler St, Brattleboro, VT 05301

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