Newest Homes for Sale in Brattleboro, VT

• 

  

  

  /40

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft

  2022 Route 9, Brattleboro, VT 05301

  Set on 2.2 wooded acres in Marlboro, this 3-bedroom, 2-bath Cape offers 1,410 square feet of living space and plenty of classic Vermont character. The main level features a spacious kitchen and dining area, a comfortable living room with a brick fireplace and hearth, a first-floor bedroom, full bath, and convenient laundry hookups. Two additional bedrooms and a second full bath are located

  Grayson VanHendrick Flex Realty

  2022 Route 9, Brattleboro, VT 05301
• 

  

  

  /26

  $330,000

  • 4 Beds
  • 1.5 Baths
  • 2,189 Sq Ft

  36 Paul's Rd Unit 6-259, Guilford, VT 05301

  Welcome to a bright, airy home that blends comfort, character, and convenience! Set on 1.26 acres of sunny lawn and wooded privacy, this four-bedroom, two-bath property offers inviting, freshly painted living spaces, central air, and efficient baseboard radiant heat. The living room features a welcoming fireplace, while the kitchen includes a woodstove setup and comes fully applianced with a

  John Mcpherson Berkley & Veller Greenwood Country

  36 Paul's Rd Unit 6-259, Guilford, VT 05301
• 

  

  

  /31

  $260,000

  • 4 Beds
  • 2.5 Baths
  • 2,572 Sq Ft

  106 Coolidge Hwy Unit 6-276, Guilford, VT 05301

  Beautiful 1925 stucco Craftsman home needing TLC. Narrow strip oak flooring throughout, brick fireplace with original oak trim, original windows, beautiful oak staircase, arched doorways, dining room with enclosed porch, and a big country kitchen. There are many original features that make this property a great investment. The main house offers 2 sunny bedrooms; the adjacent finished apartment

  John Mcpherson Berkley & Veller Greenwood Country

  106 Coolidge Hwy Unit 6-276, Guilford, VT 05301
• 

  

  

  /5

  $425,000

  • 3,439 Sq Ft

  126 Oak Grove Ave, Brattleboro, VT 05301

  Outstanding investment opportunity! This well-maintained 5-unit apartment building offers strong income in a highly desirable neighborhood close to downtown, shopping, schools, and the hospital. The property features five 1-bedroom apartments and has seen some updates, including some new vinyl replacement windows, one unit fully renovated, recently painted porches, and improvements to portions of

  Angela Sherman Brattleboro Area Realty

  126 Oak Grove Ave, Brattleboro, VT 05301
• 

  

  

  /40

  $350,000

  • 2,745 Sq Ft

  120 Western Ave, Brattleboro, VT 05301

  Discover this lovingly cared-for two-unit multi-family property, ideally located in town with convenient access to shopping, restaurants, public transportation, and everyday amenities. Each unit offers a comfortable layout featuring 2 bedrooms and 1 bathroom, making this property an excellent opportunity for owner-occupants, investors, or those seeking rental income. Pride of ownership is evident

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  120 Western Ave, Brattleboro, VT 05301
• 

  

  /36

  $729,000

  • 3 Beds
  • 3 Baths
  • 3,400 Sq Ft

  219 Hillcrest Terrace, Brattleboro, VT 05301

  A rare combination of recreation & convenience in one of Brattleboro's most desirable neighborhoods. This home is designed for living & entertaining! The property sits on 1.6 acres of landscaped grounds with sweeping views of Mt. Wantastiquet showcasing spectacular sunrises & front-row views of Brattleboro's 4th of July fireworks. Tucked beside Living Memorial Park on a quiet cul-de-sac where

  Robert Doyle Berkley & Veller Greenwood Country

  219 Hillcrest Terrace, Brattleboro, VT 05301
• 

  

  /27

  $295,000

  • 3 Beds
  • 1 Bath
  • 1,350 Sq Ft

  136 Oak Grove Ave, Brattleboro, VT 05301

  Timeless Character on Coveted Oak Grove Avenue!There's something special about an American Foursquare. Built for comfort and designed to stand the test of time, this quintessential early 20th-century home welcomes you with classic architecture, generous room sizes, and the warmth of original craftsmanship.Set on a desirable in-town lot along Oak Grove Avenue, this 3-bedroom home showcases

  Liz LaVorgna Brattleboro Area Realty

  136 Oak Grove Ave, Brattleboro, VT 05301
• 

  

  /17

  $265,000

  Open Sat 11AM - 1PM

  • 2 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  9 Evergreen Ln, Brattleboro, VT 05301

  Nestled next to Brattleboro's favorite public park, this end unit is wrapped in coveted out door space ,wrapping from the coffee deck all the way around to the back brick patio It also features a private garage with auto open, and laundry and storage neatly behind, The parking is paved with plenty of room for guests. Inside the ample galley kitchen has everything you need including a large top

  Christine Lewis Brattleboro Area Realty

  9 Evergreen Ln, Brattleboro, VT 05301
• 

  

  /25

  $250,000

  • 2 Beds
  • 1.5 Baths
  • 2,496 Sq Ft

  11 Evergreen Ln, Brattleboro, VT 05301

  This inviting 2 bedroom, 2-bathroom townhouse is located with privacy but close to Brattleboro amenities. Drive into your one car garage, in addition there is a storage area and laundry room. The second floor has a spacious living room and galley kitchen with eating nook which flows into a dining room and outdoor deck. The third level of this cozy condominium has a full sectional bathroom and 2

  Janet Lucier Barrett & Valley Assoc. Inc

  11 Evergreen Ln, Brattleboro, VT 05301
• 

  

  /17

  $110,000

  • Land
  • 5,227 Sq Ft
  • $916,667 per Acre

  117 * Fuller Dr, Brattleboro, VT 05301

  Nestled just behind 117 Fuller Drive, with privacy and easy access from the street, this property is the perfect spot for the tiny home you have been longing for. Water, sewer, and electric are all at the street, and the seller will help to keep the access accessible :) The subdivision has received preliminary approval from the town, with finalization to be completed prior to sale—giving you

  Rebecca Seymour Brattleboro Area Realty

  117 * Fuller Dr, Brattleboro, VT 05301
• 

  

  /32

  $495,000

  • 3,882 Sq Ft

  1309 Putney Rd, Brattleboro, VT 05301

  Exceptional investment opportunity! This well maintained six-unit property is in outstanding condition and has seen numerous recent improvements, making it an attractive addition to any investment portfolio. Exterior updates include fresh paint completed last year, newer windows (approximately three years old), a newer rubber membrane roof, buried power, updated electrical, a newer hot water

  Kerry Mulverhill

  1309 Putney Rd, Brattleboro, VT 05301
• 

  

  /12

  $285,000

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  455 S Main St, Brattleboro, VT 05301

  Tucked in near schools, hospital, shopping and a short walk to fishing and a canoe ride. Room enough for a garden, play space and just the right size for new beginnings. Nice sun porch doubles a a mud room, kitchen is huge with room enough for an island, a sweet spot with lots of potential.

  Christine Lewis Brattleboro Area Realty

  455 S Main St, Brattleboro, VT 05301
• 

  

  /13

  $465,500

  $50K PRICE DROP

  • 3,364 Sq Ft

  28 Brook St, Brattleboro, VT 05301

  Strong returns and future potential define this well-maintained 4-unit investment property in vibrant Brattleboro. Offered at an impressive 10% cap rate, the building consists of four spacious 2-bedroom, 1-bath apartments, providing a desirable and consistent unit mix. Pride of ownership is evident throughout, making this a turnkey addition to any portfolio. Beyond the existing income, the

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  28 Brook St, Brattleboro, VT 05301
• 

  

  /11

  $422,000

  $43K PRICE DROP

  • 3,756 Sq Ft

  820 Western Ave, Brattleboro, VT 05301

  Exceptional cash flow meets classic Vermont charm in this well-maintained 4-unit property in the heart of Brattleboro. Offered at an impressive 10% cap rate, the building features a desirable unit mix with two 2-bedroom, 1-bath apartments and two 1-bedroom, 1-bath apartments. Recent improvements include a freshly painted exterior in 2025 and bathroom renovations completed in 2023, reflecting

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  820 Western Ave, Brattleboro, VT 05301
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  /34

  $78,000

  • 2 Beds
  • 1 Bath
  • 552 Sq Ft

  22 Valley St, Brattleboro, VT 05301

  Welcome to 22 Valley Road, an affordable and easy-to-maintain 2-bedroom, 1-bath mobile home located in Brattleboro’s Tri-Park Cooperative Housing Corporation. This cozy single-level home offers a bright and refreshed interior with natural light, LED lighting, first-floor laundry hookups, and a functional layout that makes great use of the space. The kitchen features an electric range,

  Grayson VanHendrick Flex Realty

  22 Valley St, Brattleboro, VT 05301
• 

  

  /38

  $309,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,140 Sq Ft

  48 Carriage Hill Rd, Brattleboro, VT 05301

  ***Open House Sunday 7/19 from 11am-1pm** Welcome to a home where everyday living feels just a little more special. Offering three comfortable bedrooms and a functional, inviting layout, this property is designed for everything from quiet evenings at home to hosting family and friends. The true highlight is the incredible backyard, a rare, fully fenced, level oasis that's ready for every season

  Jonathan Griffus BHG Masiello Keene

  48 Carriage Hill Rd, Brattleboro, VT 05301
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  /60

  $795,000

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

  947 Miller Rd, Brattleboro, VT 05301

  Stunning Southern Vermont home with views, gardens and private pond on 10 acres incoveted Dummerston, Windham County. Entering the circular drive, lush perennial gardens welcome you and the magic begins. This meticulously designed 1600-square-foot home features soaring ceilings and superior craftsmanship throughout. Thespacious kitchen includes custom cabinetry, Sub-Zero and Wolf

  Kristen Ziter Taylor Brattleboro Area Realty

  947 Miller Rd, Brattleboro, VT 05301
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  /52

  $1,350,000

  $50K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,536 Sq Ft

  1845 Hatch School Rd, Brattleboro, VT 05301

  Thoughtfully constructed in 2016 with efficiency, durability, and longevity in mind, this modern farmhouse offers 3,536 square feet of open, light-filled living space on nearly 100 private acres, just 0.8 miles from the Wilmington town line. Built with double-wall construction, a high-performance building envelope, and imported European triple-pane windows, the home reflects a deliberate

  Melissa Nebelski Real Broker LLC

  1845 Hatch School Rd, Brattleboro, VT 05301
• 

  

  /37

  $299,000

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  412 Western Ave, Brattleboro, VT 05301

  Move-in ready and full of potential, this charming Brattleboro home is ready for its next chapter. The main level features a bright, open-concept layout with a spacious kitchen and comfortable living area, creating an ideal space for everyday living and entertaining. Filled with natural light, the living room opens directly onto a private rear deck overlooking a manageable backyard—perfect for

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  412 Western Ave, Brattleboro, VT 05301
• 

  

  /30

  $305,000

  $10K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,607 Sq Ft

  136 Morningside Dr, Brattleboro, VT 05301

  Rare opportunity to enjoy single-level living with all modern conveniences on the main floor in this magnificent condo unit. Featuring a spacious primary bedroom with a walk-in closet and full en-suite bathroom, this home offers comfort and functionality throughout. A second bedroom provides flexibility for guests, a home office, or additional living space. The open-concept kitchen and dining

  Desiree Stango Berkley & Veller Greenwood Country

  136 Morningside Dr, Brattleboro, VT 05301
• 

  

  /26

  $1,350,000

  • 7,660 Sq Ft

  131,133,141 Green St, Brattleboro, VT 05301

  What an opportunity to own 11 units in 3 separate buildings with a fantastic rental history. Close to downtown, schools, shopping and bus routes. Very well maintained properties with 3 - two bedroom units and 8 one bedroom units. On site laundry for the convenience of tenants. Wonderful features including hardwood floors and large windows for exceptional natural light. Great porches and very

  Susan Bellville Bellville Realty

  131,133,141 Green St, Brattleboro, VT 05301
• 

  

  /44

  $475,000

  • 6 Beds
  • 2.5 Baths
  • 3,682 Sq Ft

  4303 Hinesburg Rd, Brattleboro, VT 05301

  Private! Guilford! This unusual combination of a true log home with an incredible center double sided chimney....a fireplace facing the kitchen/dining and wood stove in the living room, bringing the best of both worlds:... ambience and warmth. There is a surprise of one more fireplace on the 2nd floor in the charming primary bedroom...use the ensuite for a huge walk in closet. The other half of

  Christine Lewis Brattleboro Area Realty

  4303 Hinesburg Rd, Brattleboro, VT 05301
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  /4

  $499,000

  $41K PRICE DROP

  • 6,000 Sq Ft

  16 School St, Brattleboro, VT 05301

  Attention Investors & 1031 Exchange Buyers! A premier, turn-key investment opportunity is now available in the high-demand Brattleboro rental market. Offered at $540,000, this massive, stately 6-unit multifamily building delivers immediate, fully stabilized cash flow from day one. With a robust gross monthly income of $7,675 and an outstanding gross annual income of $92,100, this property is a

  Kate Barry EXP Realty

  16 School St, Brattleboro, VT 05301
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  /37

  $340,000

  $10K PRICE DROP

  • 1,918 Sq Ft

  50 Oak Grove Ave, Brattleboro, VT 05301

  Excellent opportunity to own a three-unit investment property in a fabulous location. Enjoy being near the well-known Little League field, grab a hot dog and catch a game. Conveniently located near public transportation, the hospital, shopping, restaurants, schools, and other local amenities. The property offers a great yard set back from the road, providing both privacy and usable outdoor space.

  Kerry Mulverhill

  50 Oak Grove Ave, Brattleboro, VT 05301
• 

  

  /36

  $325,000

  $10K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,216 Sq Ft

  6 Sycamore St, Brattleboro, VT 05301

  Located in one of Brattleboro’s desirable neighborhoods, this inviting 4-bedroom home offers a comfortable layout, great natural light, and convenient access to schools, parks, trails, shopping, and downtown amenities. The bright living room features a large bay window that fills the space with natural sunlight, while the kitchen offers ample cabinet space and overlooks the backyard. With two

  Wendie Wright Coldwell Banker LIFESTYLES - Hanover

  6 Sycamore St, Brattleboro, VT 05301
• 

  

  /24

  $295,000

  $15K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,451 Sq Ft

  461 South Rd, Brattleboro, VT 05301

  This sweet 2 bedroom, 2 bathroom home has been recently rejuvenated with a new heating system, new flooring, new kitchen cabinets and counter tops, and fresh paint inside and out, and a new septic system! There's been quite a bit done to this lovely home that's a short distance to the Marlboro town office and post office and a few minutes' ride down to Brattleboro. There's good lawn space on the

  Susan Bellville Bellville Realty

  461 South Rd, Brattleboro, VT 05301
• 

  

  /19

  $350,000

  $35K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,521 Sq Ft

  82 Oak Grove Ave, Brattleboro, VT 05301

  Neighborhood home! Living in a sweet neighborhood is a lifestyle choice. Walk to schools, playgrounds, and shopping. This vintage home has an added features of roof top solar, 2 car direct entry garage, a fenced-in yard, and lots and lots of gardens. The classic front porch is on everyone's list of must haves. The neighborhood is perfect for long evening strolls or a brisk walk at dawn. Inside

  Christine Lewis Brattleboro Area Realty

  82 Oak Grove Ave, Brattleboro, VT 05301
• 

  

  /22

  $399,000

  • 9 Beds
  • 4 Baths
  • 3,286 Sq Ft

  19 Canal St, Brattleboro, VT 05301

  Located in the heart of Brattleboro, this fully occupied and consistently high-performing investment property offers an outstanding opportunity for investors seeking strong cash flow and steady rental demand. Currently configured with 9 individual rentable rooms, the property has been successfully exclusively rented to The New England Center for Circus Arts students for years and maintains an

  Karen Hoppe Berkley & Veller Greenwood Country

  19 Canal St, Brattleboro, VT 05301
• 

  

  /37

  $595,000

  • 3 Beds
  • 3 Baths
  • 2,172 Sq Ft

  171 Green Meadow, Brattleboro, VT 05301

  Immaculate! Lovingly reimagined over two decades, this impeccable residence blends thoughtful design with modern sustainability. The heart of the home is a chef’s kitchen with ample counter space and a spacious pantry with an integrated dining area—perfect for entertaining. Relax in the stunning living room, anchored by a gas insert fireplace crafted by a very talented local mason. Outdoor living

  Thomas Dahlin Berkley & Veller Greenwood Country

  171 Green Meadow, Brattleboro, VT 05301
• 

  

  /17

  $329,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft

  550 S Main St, Brattleboro, VT 05301

  Lovely level lot, close to schools, hospital, shopping, State park and downtown. The best of everything, and BRAND NEW!!! Be the the envy of all your friends, with this wonderful, open concept, one level home. Primary bedroom on one end with an ensuite for privacy! New, shiny appliances, good sized island for cooking or hanging out and both a tub and a walk in shower. Special in so many ways,

  Christine Lewis Brattleboro Area Realty

  550 S Main St, Brattleboro, VT 05301
• 

  

  /32

  $475,000

  $75K PRICE DROP

  • 4,116 Sq Ft

  33 Oak St, Brattleboro, VT 05301

  This is a rare opportunity to take over a multi-family project in the heart of Brattleboro. The 0.40-acre site features a vacant three-story building that has already been gutted and fully remediated for lead paint. With town zoning already approved to expand from 8 to 13 units and full architect plans included, the heavy lifting and permitting phase is already behind you. Upon completion, the

  Kate Barry EXP Realty

  33 Oak St, Brattleboro, VT 05301
• 

  

  /38

  $769,900

  $25K PRICE DROP

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

  5 Hillwinds N, Brattleboro, VT 05301

  Owner plans on house roof replacement, skylight replacement and necessary chimney work. Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on almost 2 acres of landscaped grounds with lawns, stone walls & gardens, plus an adjoining 9.4 acre woodland lot with snowshoe trails in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to

  Robert Doyle Berkley & Veller Greenwood Country

  5 Hillwinds N, Brattleboro, VT 05301
• 

  

  /17

  $255,000

  $30K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 1,320 Sq Ft

  116 Birge St Unit 2, Brattleboro, VT 05301

  Simple but elegant! Historic posts and wonderful beams define the magnificent open concept, giving visual shape and creating traditional options or whimsical uses for your new lifestyle. High ceilings and huge windows create a celebration of light, complementing the glowing antique floors magical in combination and truly beautiful. A home, an artist loft...so many uses, so unique, so

  Christine Lewis Brattleboro Area Realty

  116 Birge St Unit 2, Brattleboro, VT 05301
• 

  

  /32

  $429,000

  $70K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,550 Sq Ft

  77 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 mile

  Dan Normandeau Berkley & Veller Greenwood Country

  77 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  /15

  $149,900

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 685 Sq Ft

  39 Brookside Dr Unit 7, Brattleboro, VT 05301

  Move right in! This condo has had some updates to include new scratch resistant vinyl plank flooring, new bathroom vanity, new kitchen range and freshly painted interior. Located in a prime location with quick, easy access to I91 and a stones throw to the Whetstone Brook, Farmers Market and Living Memorial Park. Shared basement with assigned storage space. Association fees include heat,

  Angela Sherman Brattleboro Area Realty

  39 Brookside Dr Unit 7, Brattleboro, VT 05301
• 

  

  /35

  $239,000

  $50K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 2,000 Sq Ft

  116 Birge St Unit 3, Brattleboro, VT 05301

  Price Improvement! Welcome to Esteyville! Here, history, location, and distinctiveness excel. This rare, NYC loft-style condo on the 3rd and 4th floors was formerly home to Estey Organ, the world's largest pipe organ manufacturer, circa 1870. Listed in the National Registry of Historic Places, you will find original pine wide-plank floors, exposed post-and-beam construction, soaring ceilings,

  Liz LaVorgna Brattleboro Area Realty

  116 Birge St Unit 3, Brattleboro, VT 05301
• 

  

  /20

  $320,000

  $34K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  39 Atwood St, Brattleboro, VT 05301

  First time offered, EVER... built and loved by the current family, it is time to pass the keys to a new generation of owners ready to put their own love and dreams into this sweet home. Just across from the high and middle schools, around the corner from Oak Grove grade school, and down the street from the hospital and shopping. There is a first floor bed and bath for aging in place, but 2 big

  Christine Lewis Brattleboro Area Realty

  39 Atwood St, Brattleboro, VT 05301
• 

  

  /51

  $284,000

  $15K PRICE DROP

  • 2,360 Sq Ft

  5 Reynolds Dr, Brattleboro, VT 05301

  Turn-Key Investment in the Heart of Brattleboro! This versatile three-unit multifamily property offers an excellent opportunity for investors. Two of the three units have been recently and extensively renovated, featuring brand-new flooring, fresh paint, modern baseboards, and updated plumbing and light fixtures. All three units are currently occupied, providing immediate cash flow. Unit 2 also

  Kate Barry EXP Realty

  5 Reynolds Dr, Brattleboro, VT 05301
• 

  

  /8

  $48,000

  $4K PRICE DROP

  • Land
  • 6.1 Acres
  • $7,869 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
• 

  

  /60

  $3,800,000

  $2M PRICE DROP

  • 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

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