Homes for Sale in 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

  (802) 317-7158

  1950 Collins Rd, Brattleboro, VT 05301
• 

  

  

  /32

  $495,000

  $55K 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
• 

  

  

  /8

  $119,999

  • Land
  • 15 Acres
  • $8,000 per Acre

  0 Carpenter Hill Rd Unit 5090787, Guilford, VT 05301

  Hillside building lot deeded for one beautiful home, with a straight-ahead view of inspiring mountains and valleys to the south. The property is moderately sloped near the road but more flat at the highest elevation, with benches of level ground at intervals up and down the land. A network of hiking trails is blazed across the property, but the easiest way to view the high ground is what remains

  David White OwnerEntry.com

  0 Carpenter Hill Rd Unit 5090787, Guilford, VT 05301
• 

  

  

  /6

  $295,000

  • 4 Beds
  • 2 Baths
  • 1,744 Sq Ft

  48 Pleasant St, Brattleboro, VT 05301

  This handsome two unit home is located on desirable Pleasant Street and includes a large yard with plenty of parking. Each unit is 2 bedrooms, bath, living room and kitchen and they feature softwood flooring, bulls eye molding, replacement windows, decking and a covered front porch. Tenant pays for Electric and Heat and each unit has new Buderus boilers. W&D hookup up and Coin washer and dryer in

  Robert Doyle Berkley & Veller Greenwood Country

  48 Pleasant St, Brattleboro, VT 05301
• 

  

  

  /46

  $699,000

  $100K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,353 Sq Ft

  2416 Stage Rd, Guilford, VT 05301

  A truly magical setting! If you've never experienced the blissfulness of the Green River Village and its historic covered bridge and crib dam/waterfall and one of the most spectacular swimming holes imaginable, it's a must visit southern Vermont destination. Nestled in this picturesque valley village is this charming old home privately situated on 53.5 acres only a short stroll up the driveway

  Chris Long BHG Masiello Brattleboro

  2416 Stage Rd, Guilford, VT 05301
• 

  /2

  $245,000

  • 4 Beds
  • 2 Baths
  • 2,148 Sq Ft

  69 Grove St, Brattleboro, VT 05301

  69 Grove Street is a pleasant 2 unit home just a short walk from vibrant downtown. Each unit features 2 bedrooms, bath, living room and kitchen with wide board flooring and replacement windows. The first floor unit has a covered front porch, pantry and W&D hookups in the basement. The second floor apartment has an additional room (office), W&D hookups, decking and a rear staircase. Recent

  Robert Doyle Berkley & Veller Greenwood Country

  69 Grove St, Brattleboro, VT 05301
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  /24

  $139,000

  $20K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 592 Sq Ft

  219 High St Unit 3, Brattleboro, VT 05301

  Welcome to the effortless existence of condominium life with the rare addition of uniqueness. How nice to own a home while splitting the expenses with two other condo owners. Park in your driveway and follow a pretty stone path to your first-floor sanctuary. This efficient 592 sq ft space offers an open kitchen, dining area with a washer and dryer, living room, one bedroom, and a full bath. Share

  Kristen Ziter Taylor Brattleboro Area Realty

  219 High St Unit 3, Brattleboro, VT 05301
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  /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
• 

  

  /27

  $339,000

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft

  117 Oak Grove Ave, Brattleboro, VT 05301

  Located in one of the area’s most desirable and close-knit neighborhoods, this beautifully preserved 1929 home blends timeless character with thoughtful updates. Featuring hardwood floors, natural woodwork, custom built-ins, classic wainscoting, and a welcoming mudroom, the home retains the charm and craftsmanship buyers love. The open and inviting first floor offers generous living space and a

  Liz LaVorgna Brattleboro Area Realty

  117 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
• 

  /2

  $350,000

  $30K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 3,312 Sq Ft

  573 S Main St, Brattleboro, VT 05301

  Just around the corner! From the middle and high school, Oak groveelementary! Pop around the corner for all the high school games,exercise at the track. Interstate is minutes away for easy access towork or play! One apartment is over 1,000 square feet so tons of roomfor owner occupancy! 2 nice front porches. Worth looking at for eitheryour own home or as an investment. Masks

  Christine Lewis Brattleboro Area Realty

  573 S Main St, Brattleboro, VT 05301
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  /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
• 

  

  /42

  $525,000

  • 3 Beds
  • 1 Bath
  • 1,508 Sq Ft

  147 Gilbert Rd, Guilford, VT 05301

  This sweet home is nestled in the serene, and quiet location of Gilbert Rd, a dead end, located on the edge of Newfane but in the quaint town of Marlboro, VT. It has been completely renovated within the past few years by a local high-end builder with an eye for energy efficiency. His workmanship is evident in the renovation. The result: this pristine home gleams with its fresh and inviting

  Monica Sumner BHG Masiello Brattleboro

  147 Gilbert Rd, Guilford, VT 05301
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  /40

  $665,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft

  47 Oak Hill Dr, Dummerston, VT 05301

  Tucked away on a private road, this impeccably maintained 3-bedroom, 2-bathroom home sits on a serene 6-acre lot, offering the perfect blend of privacy and comfort. Set well back from the road, the property provides a peaceful retreat surrounded by nature. Inside, you’ll find a bright and inviting open-concept layout designed for both everyday living and entertaining. The spacious living and

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  47 Oak Hill Dr, Dummerston, VT 05301
• 

  

  /7

  $75,000

  • Land
  • 20.8 Acres
  • $3,606 per Acre

  0 Hunter Brook Rd, Marlboro, VT 05344

  *Please do not go onto the neighbors driveways.* Deep into Marlboro, on a seasonal rd, set up camp and fall asleep to the white noise of the brook. The campsite is flat, right off the road and then the land slopes upward. At the back there is a shared pond site.Hunter Brook Rd is not maintained in the wintertime, from the Marlboro side; you'll need to snowmobile, ski or walk in.

  Victoria Woods Brattleboro Area Realty

  0 Hunter Brook Rd, Marlboro, VT 05344
• 

  /2

  $370,000

  • 5 Beds
  • 4 Baths
  • 3,002 Sq Ft

  10 Birge St, Brattleboro, VT 05301

  Invest in your own home town! Full tenant roster with the easy access to laundry across the street, grocery stores, train and The Moover. Right in the heart of things with little yard to maintain! Consider as an investment in your portfolio or decide to live in one unit and have the others pay your mortgage! Good way to start, retire or increase your portfolio! Owner is a licensed appraiser.

  Christine Lewis Brattleboro Area Realty

  10 Birge St, Brattleboro, VT 05301
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  /24

  $310,000

  • 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
• 

  

  /40

  $825,000

  • 5 Beds
  • 1 Bath
  • 1,224 Sq Ft

  6036 Jacksonville Stage Rd, Guilford, VT 05301

  Imagine 216 acres of rolling fields, serene woodlands, and a glowing sugarbush tucked along a quiet country dirt road near the Massachusetts border in Halifax, just a short drive to Brattleboro and Wilmington. Held by the same family for generations, this timeless Southern Vermont property includes a farmhouse, barns, and several outbuildings—many ready for restoration, reimagining, or

  Melissa Nebelski Real Broker LLC

  6036 Jacksonville Stage Rd, Guilford, VT 05301
• 

  

  /55

  $849,000

  • 6 Beds
  • 6.5 Baths
  • 3,877 Sq Ft

  2435 Stage Rd, Guilford, VT 05301

  Only a fortunate few have the privilege of calling Green River Village home—a quintessential Vermont hamlet distinguished by its historic covered bridge, the 1811 timber crib dam, and the iconic wood-spired church perched proudly on the hillside above. Sited adjacent to the bridge, the Green River Bridge House, originally a blacksmith shop, enjoys 300 feet of frontage along the Green River. Built

  John Mcpherson Berkley & Veller Greenwood Country

  2435 Stage Rd, Guilford, VT 05301
• 

  

  /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
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  /51

  $899,800

  $49K PRICE DROP

  • 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
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  /28

  $369,900

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  39 Locust St, Brattleboro, VT 05301

  Sweet and charming from an era of wonderful wood work, polished floors and rooms with a purpose. This home has a lovely big kitchen with a peninsula for baking prep, formal dining with built in china cabinet, living room and an first floor bedroom with 1/2 bath. Since the basement is walk out, the back porch is 2nd level, above the bugs, and overlooking the private back yard. Fenced for a dog,

  Christine Lewis Brattleboro Area Realty

  39 Locust St, Brattleboro, VT 05301
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  /42

  $479,900

  $95K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft

  555 Vermont 9, Wilmington, VT 05363

  Located just minutes from the slopes of Mount Snow, the pristine waters of Lake Raponda, and the expansive Harriman Reservoir, this property offers the ideal combination of convenience, recreation, and opportunity. With ample space and zoning flexibility, you have the unique chance to build an Accessory Dwelling Unit (ADU) on-site, perfect for generating rental income, hosting guests, or creating

  Colt Hazell Flex Realty

  555 Vermont 9, Wilmington, VT 05363
• 

  

  /10

  $199,000

  $51K PRICE DROP

  • Land
  • 23.1 Acres
  • $8,615 per Acre

  184 Dupre Dr, Guilford, VT 05301

  Here's a large 23.10 +/- acre parcel that's mostly wooded but with a little bit of open field and possible short range local views. Conveniently located within a few minutes of town, here's an opportunity to enjoy country living while having access to modern amenities. There's a lot of potential for the right buyer! Please respect the privacy of the other houses on the road past this land.

  A.J. Bellville Bellville Realty

  184 Dupre Dr, Guilford, VT 05301
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  /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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  /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
• 

  

  /3

  $125,000

  $50K PRICE DROP

  • Land
  • 1.75 Acres
  • $71,429 per Acre

  0 Fort Dummer Heights Unit 4934976, Brattleboro, VT 05301

  Manicured into a beautiful high meadow, in a nice little neighborhood....sunny with views, what morecould you want? Easy to build!!! The land is open, so no fuss with a lot of prep. This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor

  Christine Lewis Brattleboro Area Realty

  0 Fort Dummer Heights Unit 4934976, Brattleboro, VT 05301
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  /38

  $749,000

  $46K PRICE DROP

  • 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 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 downtown and the Country Club. Step inside the striking custom-designed interior through

  Robert Doyle Berkley & Veller Greenwood Country

  5 Hillwinds N, Brattleboro, VT 05301
• 

  

  /42

  $467,000

  Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 2,400 Sq Ft

  3524 Deer Park Rd, West Halifax, VT 05358

  Elevated from the Road, this spectacular three-bedroom, two-bath home with 22 acres offers gardening, farming, and hiking and snowshoeing trails. Bright sunlight abundantly welcomes you from room to room. The spacious kitchen includes a dinette with a cozy wood stove and a walkout to the rebuilt, large deck overlooking your picturesque open meadow. The qualitycraftsmanship is evident

  Kristen Ziter Taylor Brattleboro Area Realty

  3524 Deer Park Rd, West Halifax, VT 05358
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  /30

  $315,000

  • 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
• 

  

  /4

  $125,000

  $15K PRICE DROP

  • Land
  • 1.3 Acres
  • $96,154 per Acre

  00 Creamery Rd, Guilford, VT 05301

  Just in time for Spring building! This incredibly beautiful high meadow is perfect for your new home, be it a get away or primary. Wake up to the views of the local hills and rolling countryside...enjoy gardening, a pool, decks or covered porches ..or just install oversized windows to take advantage while you putter about! Soils tests are done...drive is into the lot...consult GMP for power...Get

  Christine Lewis Brattleboro Area Realty

  00 Creamery Rd, Guilford, VT 05301
• 

  

  /60

  $1,215,000

  • 4 Beds
  • 3 Baths
  • 3,632 Sq Ft

  350 Sunset Lake Rd, Newfane, VT 05301

  Experience the timeless charm of Vermont living at this beautifully renovated farmhouse estate sitting on 92 acres in Newfane Vermont. Originally restored and thoughtfully updated, this exceptional antique farmhouse seamlessly blends historic character with modern comfort and convenience. Unlike many older homes, this property features expansive rooms, high ceilings, wood floors, abundant natural

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  350 Sunset Lake Rd, Newfane, VT 05301
• 

  

  /10

  $250,000

  • 2 Beds
  • 2 Baths
  • 1,139 Sq Ft

  108 Morningside Commons, Brattleboro, VT 05301

  Take a deep breath...enjoy your free time...sit back and wait for the walks to be clear, the lawn mowed and the flowers to bloom...without lifting a finger! Take a dip in the clear waters of the fenced, private pool or have a game of friendly tennis or pickleball! No clean up there either! The best of the best! Top floor, end unit 2nd floor deck for looking down at the world, and windows

  Christine Lewis Brattleboro Area Realty

  108 Morningside Commons, Brattleboro, VT 05301
• 

  /2

  $80,000

  $10K PRICE DROP

  • Land
  • 1.97 Acres
  • $40,609 per Acre

  24 Summit Cir, West Brattleboro, VT 05301

  Gorgeous building lot nestled into a prime development on a wooded hillside in Southern Vermont. The 1.97 wooded lot is minutes to downtown Brattleboro, yet private and rural!

  Claire Renaud Berkley & Veller Greenwood Country

  24 Summit Cir, West Brattleboro, VT 05301
• 

  

  /28

  $325,000

  $25K PRICE INCREASE

  • 5 Beds
  • 3 Baths
  • 2,209 Sq Ft

  16 Washington St, Brattleboro, VT 05301

  Fabulous potential with this in-town home on a great neighborhood street just a few short minutes to downtown Brattleboro where you'll find shops, restaurants, galleries, and more! Close to the hospital, schools, and points north and south with easy access to Rt 91. This home retains much of the original woodwork with bulls eye trim for the doors, an elegant staircase with two stained glass

  Rebecca Seymour Brattleboro Area Realty

  16 Washington St, Brattleboro, VT 05301
• 

  

  /4

  $540,000

  • 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
• 

  /2

  $150,000

  • Land
  • 2.05 Acres
  • $73,171 per Acre

  00 Fort Dummer Heights, Brattleboro, VT 05301

  Beautiful high meadow, in a nice little neighborhood tucked up against the state park, what more could you want? Easy to build!!! The land is open, so no fuss with a lot of prep. This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor cooperation.

  Christine Lewis Brattleboro Area Realty

  00 Fort Dummer Heights, Brattleboro, VT 05301
• 

  

  /5

  $380,000

  • 6 Beds
  • 4 Baths
  • 3,264 Sq Ft

  25 Cottage St, Brattleboro, VT 05301

  Sweet neighborhood. This would be a great location for an owner to live in one unit and rent the other 3. Lots of character! Great investment possibility. Close to Hospital, nursing homes, shopping, interstate for travel. Plenty of off street parking

  Christine Lewis Brattleboro Area Realty

  25 Cottage St, Brattleboro, VT 05301
• 

  

  /23

  $78,000

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft

  4 Reservoir Rd, Brattleboro, VT 05301

  In a very private area of the Park. Right out your door is the walking path to Pleasant Valley Reservoir! This 2 bedroom home has an updated bathroom. There's a concrete grilling/patio pad, lovely flower beds line the front yard and the front and back entryway are covered.

  Victoria Woods Brattleboro Area Realty

  4 Reservoir Rd, Brattleboro, VT 05301
• 

  

  /19

  $380,000

  • 3 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  15 Lawton Dr, Brattleboro, VT 05301

  This fun and stylish gem was built and lived in by one family. Now, it is time to pass the torch! A surprise package with the look of a Gambrel but is really a raised ranch, waiting for a finish in the lower level! Cared for lovingly, and ready to move in, you will appreciate the manicured lawn, nice deck on the back, and lower level walk out and garage. The road is dead end, so little traffic.

  Christine Lewis Brattleboro Area Realty

  15 Lawton Dr, Brattleboro, VT 05301

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