Bennington County VT Homes for Sale

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  /10

  $109,000

  • Land
  • 30.8 Acres
  • $3,539 per Acre

  0 Old Gale Hill Rd Unit 5099471, Shaftsbury, VT 05262

  30 acres of Heaven located on a private road just 20 minutes from the center of Shaftsbury . There is a mix of hardwoods, evergreens and wet lands around the pond. this is suitable for a dry camp. A slice paradise to get away to in the Green Mountains.

  Dan Mason Perrott Realty

  0 Old Gale Hill Rd Unit 5099471, Shaftsbury, VT 05262
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  /11

  $260,000

  • Land
  • 3.3 Acres
  • $78,788 per Acre

  0 Mountain Haunts Unit 5099438, Winhall, VT 05340

  The 3.3-acre parcel of land located on Mt Haunts Road in Winhall has received approval for the construction of a four-bedroom residence, presenting an outstanding opportunity for prospective homeowners. This exceptional site boasts views of Stratton Mountain Resort, allowing residents to monitor the mountain's snow conditions from the comfort of their own home each morning, as well as enjoy views

  Mike England Michael England Real Estate

  0 Mountain Haunts Unit 5099438, Winhall, VT 05340
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  /33

  $250,000

  • 2 Beds
  • 1 Bath
  • 1,504 Sq Ft

  252 Tudor Rd, Arlington, VT 05250

  Got a toolbelt, a dangerous amount of Pinterest boards, and an active imagination? It’s your time to shine! Tucked away on 3.52 blissfully serene, wooded acres in beautiful Sandgate, this rural retreat is the dictionary definition of a "diamond in the rough" just waiting for your grand vision! Born in 1983, this ranch has fantastic bones. The main house is completely liveable right now, sporting

  TG Glazer Winhall Real Estate

  252 Tudor Rd, Arlington, VT 05250
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  /30

  $595,000

  • 3 Beds
  • 2 Baths
  • 2,379 Sq Ft

  1278 Harrington Rd, Bennington, VT 05201

  Nestled on 17 picturesque acres, this spacious 3-4 bedroom, 2 full bath home offers the perfect blend of privacy, comfort, and breathtaking Vermont scenery. Built in 1993, the home features a bright, open-concept great room with expansive windows that capture stunning views of the surrounding landscape. The inviting living area is anchored by a beautiful fireplace, creating a warm and welcoming

  Kelley Mccarthy Mahar McCarthy Real Estate

  1278 Harrington Rd, Bennington, VT 05201
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  /26

  $2,300,000

  • 5 Beds
  • 3.5 Baths
  • 3,332 Sq Ft

  241 High Hill Rd, Manchester Center, VT 05255

  Perched on a hillside in one of the area's most sought-after in-town locations, this special property offers a rare combination of privacy, breathtaking mountain views, and a picturesque pond, all just moments from local shops, restaurants, and amenities. Surrounded by established landscaping and filled with natural light, the home captures the beauty of its setting through expansive windows on

  Carol O`Connor Four Seasons Sotheby's Int'l Realty

  241 High Hill Rd, Manchester Center, VT 05255
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  /29

  $265,000

  • 3 Beds
  • 1.5 Baths
  • 1,688 Sq Ft

  128 Northside Dr, Bennington, VT 05201

  Welcome to this classic 3-bedroom, 1.5-bath Cape style home located in a planned commercial zone. Offering 1,688 square feet of well-designed living space on a manageable 0.26-acre lot, this inviting residence is perfect for comfortable family living. Offers beautiful hardwood floors gracing the upstairs bedrooms, as well as the spacious living and dining rooms—ideal for gathering with loved

  Timothy Corcoran Mahar McCarthy Real Estate

  128 Northside Dr, Bennington, VT 05201
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  /60

  $989,900

  • 4 Beds
  • 3 Baths
  • 5,697 Sq Ft

  66 Somerset Rd, Searsburg, VT 05363

  A truly extraordinary, gated Vermont retreat, backing up to the Green Mountain National Forest. This remarkable mountain haven offers a rare lifestyle: waterfalls in the backyard, a sitting deck surrounded by nature, more than 65 perennials and established gardens, easy-maintenance grounds, and extraordinary access to Southern Vermont recreation. Inside, enjoy post-and-beam warmth, hardwood

  Erica Reynolds Southern Vermont Realty Group

  66 Somerset Rd, Searsburg, VT 05363
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  /4

  $50,000

  • Land
  • 43,124 Sq Ft
  • $50,505 per Acre

  0 Route 30 Unit 5099207, Winhall, VT 05340

  Wooded one acre parcel off Rt 30 in Winhall, just past the west entrance to French Hollow Rd. and by Green Mountain National Forest and VTRT 30. This is a sloping /wooded parcel that extends down to the Mill Brook. There seems to be a nice plateau/bench as a possible build site........All Buyers should/must do their Own due diligence.

  Mike England Michael England Real Estate

  0 Route 30 Unit 5099207, Winhall, VT 05340
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  /50

  $499,000

  • 4 Beds
  • 2 Baths
  • 2,144 Sq Ft

  5131 Main Rd, Stamford, VT 05352

  Set on 2.85 acres with beautiful mountain views, this 4-bedroom, 2-bath Colonial offers space, comfort, and classic Vermont charm in the heart of Stamford. The home features 2,144 finished square feet with a welcoming layout that includes a bright living room, family room, dining area, and a spacious kitchen with warm cabinetry, an arched window, and great flow for everyday living or

  Colt Hazell Flex Realty

  5131 Main Rd, Stamford, VT 05352
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  /43

  $619,000

  • 4 Beds
  • 2.5 Baths
  • 2,692 Sq Ft

  34 Monument Ave, Bennington, VT 05201

  Set along tree-lined Monument Avenue in prestigious and historic Old Bennington, the Spargo House offers a rare opportunity to own a distinctive piece of Vermont history. Dating to circa 1800, this remarkable home was once the longtime residence of noted author, historian and collector John Spargo, founder and longtime director of the Bennington Museum. Just below the Bennington Battle Monument,

  Jeffrey Dorman

  34 Monument Ave, Bennington, VT 05201
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  /52

  $359,000

  • 2 Beds
  • 1 Bath
  • 1,686 Sq Ft

  712 Vt Route 30, Dorset, VT 05251

  Nestled in a picturesque Dorset, Vermont setting, this classic 1850 farmhouse offers an affordable opportunity to create the home of your dreams. Situated on a manageable quarter-acre lot, the property features a detached two-car garage, two additional outbuildings, screened in porch, enclosed three season porch and established perennial plantings with classic New England character throughout.

  

  Margretta Fischer

  Wohler Realty Group

  712 Vt Route 30, Dorset, VT 05251
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  /36

  $259,000

  • 4 Beds
  • 2 Baths
  • 1,768 Sq Ft

  549 Houran Rd, Bennington, VT 05201

  Well maintained and thoughtfully updated, this 4-bedroom, 2-bath home offers the ease of single-level living on a beautiful level one-acre lot in Bennington's desirable west end. Enjoy stunning mountain views from the spacious back deck or sip your morning coffee on the covered front porch. Inside, you'll find an updated kitchen, refreshed bathrooms, a cozy fireplace, central air conditioning, a

  Abi Gregorio

  549 Houran Rd, Bennington, VT 05201
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  /19

  $224,000

  • 3 Beds
  • 2 Baths
  • 1,718 Sq Ft

  7066 Main St, Readsboro, VT 05350

  So many possibilities await at this recently renovated and affordable 3-bedroom, 2-bath home, featuring two full kitchens, one up and one down. Whether you're envisioning multigenerational living, a home-based business, or simply want to be close to skiing and outdoor adventure, this versatile layout adapts to fit your life. Recent renovations touch nearly every corner of the home, including both

  Pam Tworig BISHOP WEST REAL ESTATE

  7066 Main St, Readsboro, VT 05350
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  /46

  $1,599,000

  • 6 Beds
  • 5.5 Baths
  • 5,568 Sq Ft

  144 High Meadow Rd, Winhall, VT 05340

  Expansive Stratton Mountain Resort Residence with exceptional floor plan and renovation! Featuring an upscale redesign of two top floor primary suite bathrooms, updated kitchen and expanded finished lower level, this home is ready for mountain living and endless entertaining! Designed with multiple gathering rooms and fireplaces, you'll enjoy apres ski with and an incredible open floor plan. Game

  Kim Morgan-Wohler Wohler Realty Group

  144 High Meadow Rd, Winhall, VT 05340
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  /40

  $325,000

  • 3 Beds
  • 1 Bath
  • 1,170 Sq Ft

  107 Colbrook Dr, Arlington, VT 05250

  Move right into this beautifully updated 3-bedroom, 1-bath home situated on 0.61 acres on a private dead-end road in Arlington. Offering a peaceful setting just minutes from town, this property combines privacy with convenience. The level yard features a mix of sunny and shaded spaces, perfect for outdoor enjoyment, while a year-round stream adds to the natural beauty of the property. Inside,

  David Shehadi Josiah Allen Real Estate, Inc.

  107 Colbrook Dr, Arlington, VT 05250
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  /56

  $600,000

  • 4 Beds
  • 3.5 Baths
  • 2,730 Sq Ft

  405 Old West Rd, Arlington, VT 05250

  Offered for the first time since it was custom built by the original family, this exceptional property is a rare opportunity to own a true Vermont homestead. Privately situated on more than 10 picturesque acres, the home enjoys an idyllic setting overlooking a peaceful pond with breathtaking long-range views. The surrounding landscape offers open fields, mature trees, and the sounds of nature.

  Faith Rhodes Maple Leaf Real Estate

  405 Old West Rd, Arlington, VT 05250
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  /13

  $430,000

  • 4 Beds
  • 2 Baths
  • 2,768 Sq Ft

  253 Perkins Rd, Rupert, VT 05776

  Tucked away on a quiet, town-maintained dead-end dirt road, this inviting Rupert, Vermont property offers the kind of peaceful country setting that's becoming increasingly hard to find. Set on 6.79± acres, it's a place where morning walks, afternoon bike rides, and evenings under the stars can become part of everyday life.At the heart of the property is a circa 1850 Greek Revival home, rich

  Derryl Lang Four Seasons Sotheby's Int'l Realty

  253 Perkins Rd, Rupert, VT 05776
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  /40

  $59,900

  • Land
  • 40,075 Sq Ft
  • $65,109 per Acre

  14 The Ln, Stamford, VT 05352

  Escape to the beauty of VT with this unique shed/cabin in charming Stamford VT. This is a beautiful almost 1 acre lot that has direct frontage on the North Branch of the Hoosic River. The lot is mostly cleared and level, and has quaint pathway leading down to the river, to enjoy nature. The property includes a cozy shed/cabin with solar powered lights, with 2 batteries for storage. A rustic

  Susan Colvin Monarch Realty

  14 The Ln, Stamford, VT 05352
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  /60

  $1,850,000

  • 4 Beds
  • 3.5 Baths
  • 3,828 Sq Ft

  400 Spring Brook Rd, Arlington, VT 05250

  A once-in-a-generation estate, this 125 acre property offers the rare combination that you almost never find: true privacy, two residences, forest trails, cultivated grounds, and river frontage on the Battenkill. Nestled at the base of Red Mountain on a private road, with the far shore protected by parkland, the property feels like its own secluded world while remaining minutes from Manchester

  Emily Heyer Hoffman Real Estate

  400 Spring Brook Rd, Arlington, VT 05250
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  /38

  $409,900

  • 2 Beds
  • 2 Baths
  • 1,648 Sq Ft

  1253 Old West Rd, Arlington, VT 05250

  Enjoy beautiful Green Mountain views from this exceptionally well-maintained home offering the perfect blend of comfort, space, and Vermont country living. The bright, inviting floor plan features a spacious living room with a gas fireplace, a well-appointed kitchen with abundant cabinetry, center island, gas range, stainless steel appliances, and direct access to the expansive rear deck

  Jeffrey Dorman

  1253 Old West Rd, Arlington, VT 05250
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  /32

  $1,795,000

  • 5 Beds
  • 3 Baths
  • 5,287 Sq Ft

  84 Frost Pond Rd, Dorset, VT 05251

  Tucked away on 12.3 private acres, this move-in-ready contemporary retreat offers the perfect balance of modern design, natural beauty, and effortless single-level living. Adding to its exceptional appeal, the property includes an additional building lot, creating a rare opportunity for a guest house, family compound, future expansion, or investment. Clad in timeless clear cedar siding and

  Carol O`Connor Four Seasons Sotheby's Int'l Realty

  84 Frost Pond Rd, Dorset, VT 05251
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  /29

  $3,250,000

  • 5 Beds
  • 6 Baths
  • 8,156 Sq Ft

  1613 West Rd, Manchester, VT 05254

  Located in the beautiful countryside of Manchester, Vermont, 1613 West Road offers a peaceful setting with the kind of charm and character that makes this property truly one of a kind. Surrounded by scenic mountain views, open land, and natural surroundings, the property strikes a perfect balance of privacy and convenience. Just a short drive from the heart of Manchester, you enjoy easy access to

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  1613 West Rd, Manchester, VT 05254
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  /36

  $219,000

  • 2 Beds
  • 1 Bath
  • 753 Sq Ft

  16 Old Farm Rd Unit 4, Winhall, VT 05340

  Tucked into the Old Farm community in Winhall, this inviting condominium offers classic Vermont character with the ease of association living. The main building has pre-1900 roots, with later additions that help create a warm and practical mountain-town retreat. A hydronic electric baseboard heating system, replaced when the current owners purchased the property, is complemented by a pellet stove

  Trent Stephens Wohler Realty Group

  16 Old Farm Rd Unit 4, Winhall, VT 05340
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  /22

  $579,000

  • 3 Beds
  • 1.5 Baths
  • 2,048 Sq Ft

  560 New Ireland Rd, Manchester Center, VT 05255

  This charming two-story Colonial in Manchester offers a comfortable and functional layout with plenty of living space. The first floor features a kitchen with a wood burning fireplace, along with dining and living areas perfect for everyday living and entertaining. A mudroom provides convenient access to the attached garage. Upstairs, you’ll find three additional rooms offering flexibility for

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  560 New Ireland Rd, Manchester Center, VT 05255
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  /33

  $749,000

  • 4 Beds
  • 2 Baths
  • 2,128 Sq Ft

  2 Corner Rock Rd, Winhall, VT 05340

  Stratton Mountain Renovated! 4 bedroom 2 bath is located just mins to the mountain . This home has access to all that Stratton has to offer. The Ski shuttle comes right outside your door for easy access to the mountain and your home. Freshly painted inside and out, with a partial renovation just completed. This home just installed all new windows with egress and new doors and sliders. The new

  Jessica Marullo TPW Real Estate

  2 Corner Rock Rd, Winhall, VT 05340
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  /59

  $210,000

  • 5 Beds
  • 2 Baths
  • 2,200 Sq Ft

  118 Foster Dr, Bennington, VT 05201

  Set on over 5.5 acres of private, natural surroundings, this unique split-level ranch with an auxiliary dwelling unit offers an exceptional opportunity for multi-generational living, rental income, or a private guest retreat. Surrounded by peaceful woodlands, the property provides a tranquil rural setting while remaining just a short drive from town amenities.The main residence features three

  Lindsey Martin Maple Leaf Real Estate

  118 Foster Dr, Bennington, VT 05201
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  /53

  $205,000

  • 3 Beds
  • 1.5 Baths
  • 1,632 Sq Ft

  305 Weeks St, Bennington, VT 05201

  Experience refined living in this beautifully appointed tri-level townhouse-style condominium, ideally situated just moments from downtown, the hospital, shopping, and dining. Rich in vintage character while thoughtfully updated for modern living, this exceptional residence showcases elegant quartz and butcher block countertops, a designer tile backsplash, and striking marble flooring that create

  Lindsey Martin Maple Leaf Real Estate

  305 Weeks St, Bennington, VT 05201
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  /38

  $795,000

  • 4 Beds
  • 3.5 Baths
  • 4,104 Sq Ft

  25 Benson Fuller Dr, Bondville, VT 05340

  Where Mountains Meet Modern Living: Perched just moments from the energy of Stratton Mountain Resort, this contemporary mountain home reimagines what a Vermont getaway feels like. From the moment you step inside, the design does exactly what a great contemporary home should: it steps back and lets nature take center stage. Massive, soaring windows act as living art pieces, framing sweeping,

  Robin Apps Four Seasons Sotheby's Int'l Realty

  25 Benson Fuller Dr, Bondville, VT 05340
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  /60

  $1,495,000

  Open Sat 11AM - 1PM

  • 5 Beds
  • 5 Baths
  • 5,029 Sq Ft

  20 Blackberry Ln, Peru, VT 05152

  Welcome home to this spectacular, multi-level property in Bromley Village, a private slopeside community in Peru. Conveniently located just a short walk to/from Bromley Mountain's ski slopes, the Village Clubhouse, and across from the Village pond. A well designed layout which features 5 Bedrooms (including two En-suites), a total of 5 Bathrooms, multiple spacious Living areas, and a fabulous

  Dylan Gage Bromley Real Estate

  20 Blackberry Ln, Peru, VT 05152
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  /6

  $199,900

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

  631 Oberdorf Rd, Readsboro, VT 05350

  Bring your vision and transform this 3-bedroom, 2-bathroom home into the Vermont getaway you've always wanted. Located in the private Alpenwald Village community, this fixer-upper offers a fantastic opportunity for investors, vacation home buyers, or anyone looking to build equity in a scenic mountain setting.Surrounded by the Green Mountain National Forest, the property provides direct

  Kristen Breeden Southern Vermont Realty Group

  631 Oberdorf Rd, Readsboro, VT 05350
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  /13

  $229,000

  • Land
  • 0 Sq Ft

  468 Skyboro Rd, Pownal, VT 05261

  Beautiful property featuring an impressive 835.9 feet of road frontage and over 10 partially cleared acres of private land in Pownal, Vermont. This land is situated on a private road with rolling woods, making it an ideal location to build a dream home or a vacation getaway. It offers easy access to Route 7, providing a quick drive north to the Bennington, Vermont area and local ski resorts.

  

  Sheryl Morehouse

  BISHOP WEST REAL ESTATE

  468 Skyboro Rd, Pownal, VT 05261
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  /60

  $1,650,000

  • 3 Beds
  • 4 Baths
  • 2,872 Sq Ft

  36 Beaver St, Bondville, VT 05340

  Your Ultimate Vermont Mountain Retreat Awaits! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is the perfect year-round escape - crafted for adventure, relaxation, and making lasting memories in every season. Whether you’re hitting the slopes in winter, hiking through summer trails, or soaking in the stunning fall foliage, this property delivers! Plus, it's only a

  MaryKate Grey Stratton Real Estate

  36 Beaver St, Bondville, VT 05340
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  /48

  $230,000

  • 3 Beds
  • 1.5 Baths
  • 1,128 Sq Ft

  104 Short St, Bennington, VT 05201

  Blending vintage charm with modern updates, this beautifully refreshed 3-bedroom, 2-bath home offers comfortable in-town living close to local amenities. Recent improvements include a newer roof installed just three years ago and new flooring throughout, creating a fresh and inviting atmosphere. Other additions include new kitchen appliances, furnace, and heat pump hybrid water heater, making the

  Lindsey Martin Maple Leaf Real Estate

  104 Short St, Bennington, VT 05201
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  /37

  $549,900

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

  811 Middle Pownal Rd, Bennington, VT 05201

  Thoughtfully crafted with a distinctive European-inspired character and beautifully updated throughout, this custom-built 4-bedroom, 3-bath home offers the perfect blend of quality craftsmanship, privacy, and convenience on a picturesque, landscaped lot just minutes from downtown Bennington. The bright and inviting interior features a beautifully renovated kitchen, spacious living areas with

  Jeffrey Dorman

  811 Middle Pownal Rd, Bennington, VT 05201
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  /43

  $439,000

  • 4 Beds
  • 2.5 Baths
  • 1,868 Sq Ft

  96 Twitchell Hill Rd, Shaftsbury, VT 05262

  Some homes simply have a way of making you slow down. Built in 1863, the original Twitchell Farmhouse is one of them. Rich in history and craftsmanship, this beautifully maintained four-bedroom, 2.5-bath home offers the warmth and authenticity that only a true Vermont farmhouse can provide. Original hardwood floors, handcrafted woodwork by a master carpenter, and thoughtful updates create a home

  Daire Gibney Barrett and Valley Associates Inc.

  96 Twitchell Hill Rd, Shaftsbury, VT 05262
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  /15

  $125,000

  • Land
  • 1.18 Acres
  • $105,932 per Acre

  510 Center St, Pownal, VT 05261

  Discover the potential of this scenic 1.18 acre parcel situated on a quiet street directly across from the town offices. Offering beautiful views and the convenience of town sewer, this property presents an excellent opportunity to build the home you've been dreaming of. Whether you're planning a year-round residence or a peaceful retreat, the generous lot provides plenty of space to create your

  Angela Bevin Maple Leaf Real Estate

  510 Center St, Pownal, VT 05261
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  /21

  $750,000

  • 3,216 Sq Ft

  198 Elm St, Manchester Center, VT 05255

  Rare opportunity to own a well-maintained 4-unit property in the heart of Manchester, one of Southern Vermont’s most sought-after destinations. Offered at an attractive 8% cap rate, this unique investment features a charming 2-bedroom, 2-bath carriage house, two 2-bedroom, 1-bath units, and a 1-bedroom, 1-bath apartment, providing an appealing mix for a variety of tenants. Recent updates include

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  198 Elm St, Manchester Center, VT 05255
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  /22

  $499,000

  • 3,648 Sq Ft

  938 Vt Route 7a, Shaftsbury, VT 05262

  Strong income potential and a versatile unit mix make this 4-unit property an outstanding investment opportunity. Offered at an attractive 10% cap rate, the building features two 2-bedroom, 1-bath units, a spacious 3-bedroom, 1-bath unit, and a 1-bedroom, 1-bath apartment, appealing to a wide range of tenants. This well-positioned property offers dependable rental income and the flexibility that

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  938 Vt Route 7a, Shaftsbury, VT 05262
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  /8

  $250,000

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  924 Vt Route 7a, Shaftsbury, VT 05262

  Full of character and opportunity, this charming 2-bedroom, 2-bath home in Shaftsbury offers an affordable entry into homeownership or a fantastic addition to an investment portfolio. Once serving as the local post office, the property has a unique history and a cozy footprint that makes it ideal as a starter home, downsizing option, or rental property. Recent improvements include a beautifully

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  924 Vt Route 7a, Shaftsbury, VT 05262
• 

  

  /15

  $169,000

  • 2 Beds
  • 1 Bath
  • 806 Sq Ft

  415 County St, Bennington, VT 05201

  STOP RENTING and start building equity! Call your lender today to discover the latest programs that could MAKE HOMEOWNERSHIP A REALITY. Owning may be closer than you think. The transformation inside this home is nothing short of spectacular. This move-in-ready, one-floor living bungalow has been thoughtfully designed to maximize every square foot, including a brand-new bathroom and updated

  Lori Hurley Four Corner Properties LLC

  415 County St, Bennington, VT 05201

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