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Homes for Sale in 05301

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  • /40

    $339,000

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

    65 Cedar St, Brattleboro, VT 05301

    Step into a world of artistic whimsy and historic allure at 65 Cedar Street, a property overflowing with character, magic, and boundless potential. Nestled in an ideal location with an entrance to the beloved Retreat Trails, this unique home offers an enchanting escape from the everyday. Outside, the property is embraced by beautiful, mature gardens cultivated over time in a spirit of enchanting

    Kate Barry EXP Realty

    65 Cedar St, 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
  • /25

    $270,000

    Open Sun 11AM - 1PM Coming Soon
    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    111 Central St, Brattleboro, VT 05301

    This adorable single-level home offers easy living with a functional layout and comfortable living spaces. The warm and inviting interior is designed for everyday living. The home features a large living and dining area, a convenient laundry nook, a spacious primary bedroom, and two additional bedrooms that can accommodate guests, a home office, or other multi-purpose needs. Outside, you'll find

    Desiree Stango Berkley & Veller Greenwood Country

    111 Central St, Brattleboro, VT 05301
  • /48

    $1,650,000

    • 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 expansive 219-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
  • /51

    $995,000

    Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 2,800 Sq Ft

    3924 Sweet Pond Rd, Guilford, VT 05301

    Surrounded by 65 acres of glorious land w/meadows, woodland, stone walls, and the meandering Keets Brook, this exceptional property offers a blend of beauty, privacy, and thoughtful design. The grounds are exquisitely landscaped with Gordon Hayward-designed gardens, specimen trees , stone walkways and mature blueberry bushes. A saltwater pool, private rear deck, oversized two-car garage, Kohler

    Robert Doyle Berkley & Veller Greenwood Country

    3924 Sweet Pond Rd, Guilford, VT 05301
  • /56

    $538,000

    • 4 Beds
    • 2.5 Baths
    • 2,567 Sq Ft

    1041 Church Hollow Rd, Brattleboro, VT 05301

    Country quiet and tranquility! Sun dappled trees and seventeen woodland acres surround this comfortable seven room, four bedroom, two and half bath house and two car garage. A peaceful setting where views from the deck, porch and every window take in the richness of nature and give a feeling of solitude. Built in 1987, this 2567 SF home has been much loved and well cared for. Designed for easy

    Kathy Dowd Bellville Realty

    1041 Church Hollow Rd, 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
  • /24

    $210,000

    • 2 Beds
    • 1 Bath
    • 930 Sq Ft

    40 Brookside Dr Unit 6, Brattleboro, VT 05301

    Rare to find an in-town condo with a waterfront view like this! Desirable 2 bedroom, 1 bath low maintenance, affordable home. Your spacious living/dining area has sliders looking out to the tranquil Whetstone Brook. Upstairs are 2 large bedrooms and a full bath. The lower level is a 465 square foot basement with washer/dryer hookup and extra storage. The entire interior has been freshly painted,

    Angela Sherman Brattleboro Area Realty

    40 Brookside Dr Unit 6, Brattleboro, VT 05301
  • /37

    $350,000

    • 4 Beds
    • 3 Baths
    • 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

    Kerry Mulverhill

    50 Oak Grove Ave, Brattleboro, VT 05301
  • /36

    $335,000

    • 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
  • /46

    $525,000

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

    25-27 Gingko Ln, Brattleboro, VT 05301

    Welcome to an amazing, unique opportunity on Gingko Lane in a very special location. Located on a quiet side street in this beloved neighborhood, you are in close proximity to the Retreat trails, which offer extensive hiking, and close to our vibrant downtown, a short walk away. The adorable 1,600-square-foot home has 3 bedrooms and 2 baths. The light-filled, open-concept kitchen/dining area is

    Kristen Ziter Taylor Brattleboro Area Realty

    25-27 Gingko Ln, Brattleboro, VT 05301
  • /49

    $675,000

    • 3 Beds
    • 3 Baths
    • 2,670 Sq Ft

    2079 Ames Hill Rd, Marlboro, VT 05344

    Experience the perfect blend of contemporary design and natural warmth in this stunning 2-story hybrid post & beam set on 5 landscaped acres. Thoughtfully designed with soaring ceilings, exposed beams and lots of glass, this light filled retreat brings the outdoors in while offering comfort and style in every season. Inside rich hardwood floors flow throughout the open concept living spaces,

    Tamara Purcell Berkley & Veller Greenwood Country

    2079 Ames Hill Rd, Marlboro, VT 05344
  • /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
  • /60

    $349,000

    • 3 Beds
    • 1.5 Baths
    • 1,550 Sq Ft

    90 Wilsons Woods Rd, Brattleboro, VT 05301

    Enjoy the privacy of your own space secluded from the rest of the world. Enjoy the comfort of a country setting in town. Look through the tree tops over the roofs of houses below on one side, onto a garden on another side, and onto a wooded hillside on the rest. Nature surrounds this immaculate house on a hill. Amenities include stone walls, a dog cage, a fire pit, raised gardens, a convenient

    Sally Fegley BHG Masiello Brattleboro

    90 Wilsons Woods Rd, Brattleboro, VT 05301
  • /23

    $499,000

    • 3 Beds
    • 2.5 Baths
    • 2,594 Sq Ft

    94 Brets Rd, Brattleboro, VT 05301

    Beautifully cared-for 3 bedroom, 3 bath single family condo in a desirable small association, conveniently located near town, golf course and major road access. This spacious home features a sought after first-floor primary suite with en-suite bath, skylights that fill the home with natural light, and elegant cherry flooring throughout the main living areas. The remodeled kitchen offers modern

    Oona Madden Berkley & Veller Greenwood Country

    94 Brets Rd, Brattleboro, VT 05301
  • /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
  • /19

    $385,000

    • 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
  • /43

    $340,000

    • 3 Beds
    • 2 Baths
    • 1,272 Sq Ft

    184 Carriage Hill Rd, Brattleboro, VT 05301

    Perfectly situated at the top of the hill on highly desirable Carriage Hill in West Brattleboro, this delightful yellow ranch offers the perfect blend of neighborhood comfort and exceptional curb appeal, accented by a lovely stone pathway and beautiful exterior gardens. Step out back to discover your own private oasis featuring a spacious wooden deck with a gorgeous overhead pergola, custom

    Kate Barry EXP Realty

    184 Carriage Hill Rd, Brattleboro, VT 05301
  • /28

    $385,000

    • 2 Beds
    • 2 Baths
    • 1,499 Sq Ft

    1644 Upper Dummerston Rd, Dummerston, VT 05301

    Found It! Live all on one level and tuck the guests in upstairs! The kitchen is modern with lots of counter top for the bakers and cookie makers, The laundry lives next to the kitchen and there is a second bath for visitors and guests. The sweet spot is the huge living room with a wood stove insert in the lovely fireplace. Mini-splits are already up and running for help with both heating and

    Christine Lewis Brattleboro Area Realty

    1644 Upper Dummerston Rd, Dummerston, 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
  • /27

    $389,000

    • 3 Beds
    • 2 Baths
    • 1,377 Sq Ft

    366 Hague Rd, Dummerston, VT 05301

    Historical build by local artist, incorporating wood pews and other architectural pieces reclaimed from an old Vermont church, culminating into a beautiful country home. Appreciate the picturesque views of this 5.5+- acres located on a quiet road, looking south to a lovely meadow, complete with fruit trees and a pine-lined border. This home is perfectly sized with 3 bedrooms, 2 baths and a large

    Kristen Ziter Taylor Brattleboro Area Realty

    366 Hague Rd, Dummerston, VT 05301
  • /24

    $399,000

    • 7 Beds
    • 3 Baths
    • 3,700 Sq Ft

    197 Western Ave, Brattleboro, VT 05301

    Excellent opportunity to own a well-maintained and fully occupied 3-unit investment property in the heart of Brattleboro. Located in-town with convenient access to shopping, restaurants, entertainment, and everyday amenities, this property offers strong in-place income with additional upside potential. The building consists of two 2-bedroom units and one spacious 3-bedroom unit and has been

    Karen Hoppe Berkley & Veller Greenwood Country

    197 Western 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
  • /9

    $165,000

    • Land
    • 1.9 Acres
    • $86,842 per Acre

    Lot A Sweet Pond Rd, Guilford, VT 05301

    Beautiful open 1.9-acre parcel on scenic Sweet Pond Road in Guilford, VT. Featuring open pastureland, generally level terrain, and excellent southern exposure, this property offers a wonderful opportunity for a primary residence, homestead, recreation property, or investment. A classic stone wall borders the western edge, adding timeless Vermont character. Buyers to verify utility availability

    Erica Reynolds Southern Vermont Realty Group

    Lot A Sweet Pond Rd, Guilford, 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
  • /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
  • /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
  • /46

    $799,000

    • 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
  • /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
  • /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
  • /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
  • /53

    $1,249,000

    • 4 Beds
    • 3.5 Baths
    • 4,491 Sq Ft

    390 Pleasant Valley Rd, Brattleboro, VT 05301

    Escape to this beautifully updated home set on 25.9 idyllic acres of forests, meadows and stone walls, while only minutes from amenities including the local creekside farmers market, treasured food co-op and Brattleboro's vibrant downtown. A gorgeous stone floor and blown glass windows in the entry vestibule set the tone as you are drawn to the stunning great room. The home tastefully captures

    Kristen Ziter Taylor Brattleboro Area Realty

    390 Pleasant Valley Rd, Brattleboro, VT 05301
  • /14

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    12 Autumn Gem Dr, Dummerston, VT 05301

    This affordable Dummerston home is tucked away on 11 private acres. Built with personal privacy in mind, the primary bedroom is on one end and the other 2 bedrooms and bath are at the other, eliminating hallways and adding to the living area. Warm yourself and save on fuel with the large pellet stove in the living room. Abundant light with the picture window in the front and skylight over the

    Christine Lewis Brattleboro Area Realty

    12 Autumn Gem Dr, Dummerston, 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
  • /24

    $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
  • /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
  • /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
  • /26

    $349,900

    $45K PRICE DROP
    • 3,240 Sq Ft

    458 Williams St, Brattleboro, VT 05301

    458 Williams Street, formerly the WKVT headquarters, presents an opportunity for buyers exploring potential residential or mixed-use conversion in a convenient Brattleboro location. The 3,240 SF building is currently configured for office use across two levels, with more than 10 individual rooms, multiple bathrooms, and an existing kitchenette. This layout may lend itself to reconfiguration

    Neil Goldberg Brattleboro Area Realty

    458 Williams St, Brattleboro, VT 05301

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