Bennington County VT Homes for Sale

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  /59

  $989,900

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

  66 Somerset Rd, Searsburg, VT 05363

  LOW TAXES! Six oversized garage bays across two multi-level outbuildings, direct access to National Forest, backyard waterfalls, and 5.4 private acres make this gated Southern Vermont retreat unlike anything else near Wilmington. Just five miles from downtown Wilmington and less than 12 miles from Mount Snow, the property combines substantial space for living and entertaining with exceptional

  Erica Reynolds Southern Vermont Realty Group

  66 Somerset Rd, Searsburg, VT 05363
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  /4

  $25,000

  $25K PRICE DROP

  • Land
  • 43,124 Sq Ft
  • $25,253 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

  $489,000

  $10K PRICE DROP

  • 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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  /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
• 

  

  

  /19

  $209,000

  $15K PRICE DROP

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

  7066 Main St, Readsboro, VT 05350

  Recently renovated & affordable 3-bedroom, 2-bath home comes with NEW Solar Panels INCLUDED in Price! The home has two full kitchens, one up and one down and comes partially furnished. 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

  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

  $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 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. It is mostly cleared & level & has a quaint pathway leading down to the river, to enjoy nature. The property includes a cozy 16x10 cabin with solar powered battery system for lights and to plug things into. with 2

  Susan Colvin Monarch Realty

  14 The Ln, Stamford, VT 05352
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  /60

  $1,750,000

  $100K PRICE DROP

  • 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

  $399,000

  $11K PRICE DROP

  • 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

  **Privacy. Design. Nature. Possibility.** Tucked away on 12.3 acres, this exceptional contemporary retreat is the kind of property that makes you slow down the moment you arrive. A peaceful pond, mature woodlands, and complete privacy create an extraordinary setting, while the home's thoughtful architecture brings the beauty of the outdoors into every room.Wrapped in beautiful clear cedar

  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
• 

  

  /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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  /59

  $190,000

  $20K PRICE DROP

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

  118 Foster Dr, Bennington, VT 05201

  Invest in the potential with this unique split-level ranch and guest house. This property presents an exceptional opportunity for anyone looking to roll up their sleeves and bring a property back to life. Set on expansive acreage surrounded by peaceful woodlands, the property offers a tranquil rural setting while remaining just a short drive from town amenities.The main residence features

  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

  • 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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  /10

  $169,000

  $31K PRICE DROP

  • 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
  • 5,072 Sq Ft

  36 Beaver St, Bondville, VT 05340

  Your Ultimate Vermont Mountain Retreat Awaits! Luxury log home plus a 2,250 sqft guest house! 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,

  MaryKate Grey Stratton Real Estate

  36 Beaver St, Bondville, VT 05340
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  /37

  $539,900

  $10K PRICE DROP

  • 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
• 

  

  /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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  /17

  $635,000

  $115K PRICE DROP

  • 3,216 Sq Ft

  198 Elm St, Manchester Center, VT 05255

  Enjoy the privacy and charm of your own well-maintained carriage house in the heart of Manchester while the additional three-unit apartment building generates income to help cover the property’s expenses. The inviting carriage house offers 2 bedrooms and 2 baths, while the separate building features two 2-bedroom, 1-bath units and one 1-bedroom, 1-bath apartment. Recent updates include new

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  198 Elm St, Manchester Center, VT 05255
• 

  

  /22

  $435,000

  $64K PRICE DROP

  • 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. 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 investors seek. Whether you're adding

  The Nancy Jenkins Team Nancy Jenkins Real Estate

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

  $199,000

  $51K PRICE DROP

  • 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
• 

  

  /50

  $150,000

  $10K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,575 Sq Ft

  127 Dewey St, Bennington, VT 05201

  Opportunity awaits with this spacious property offering incredible potential for investors, renovators, or buyers looking to create their dream home. Currently configured as a single family residence, this home features 5 bedrooms and 2 bathrooms. At one point it was a 2 unit home and could potentially be again.Inside, you'll find generous living space ready for your vision and updates. A

  Lindsey Martin Maple Leaf Real Estate

  127 Dewey St, Bennington, VT 05201
• 

  /2

  $3,934,900

  $1M PRICE DROP

  • 33,801 Sq Ft

  1000 Investors Ln, Manchester, VT 05255

  Exceptional opportunity to acquire a well-established Vermont investment portfolio consisting of 10 properties inclusive of 33 residential units and 2 commercial units located across the desirable communities of Brattleboro, Ludlow, Manchester, Cavendish, Shaftsbury, Proctorsville, and Chester. This diverse portfolio has been thoughtfully maintained and professionally managed, with many long-term

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  1000 Investors Ln, Manchester, VT 05255
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  /26

  $1,575,000

  • 3 Beds
  • 2.5 Baths
  • 3,264 Sq Ft

  777 McCooey Dr, Manchester Center, VT 05255

  Set back from a quiet country road in Manchester, Vermont, this spaciousFederal farmhouse style home offers a wonderful blend of comfort, privacyand Vermont charm. The classic white exterior with its attached red barncreates a welcoming first impression, while the home’s thoughtful designprovides plenty of space for everyday living, entertaining and enjoying thepeaceful

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

  777 McCooey Dr, Manchester Center, VT 05255
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  /14

  $135,000

  $5K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 948 Sq Ft

  432 South St Unit C10, Bennington, VT 05201

  Townhouse style condo on the north side of Nathaniel court. Living room, kitchen, and half bath downstairs. Upstairs is the full bath with laundry and 2 bedrooms. All units have new roof within the last 5 years. No pets allowed. No smoking. Dues are $760 a quarter.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  432 South St Unit C10, Bennington, VT 05201
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  /37

  $264,900

  $24K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,146 Sq Ft

  109 County St, Bennington, VT 05201

  The renovations are done, just move in! Nearly everything is NEW at 109 County Street, including the price! In addition, the seller is offering a $5K credit towards the buyer’s closing costs. This extensively renovated 4BR/2BA home with a fully fenced yard gives you the opportunity to enjoy the benefits of a much newer home without the time, expense, and stress of renovating one yourself.

  Angela Bevin Maple Leaf Real Estate

  109 County St, Bennington, VT 05201
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  /42

  $180,000

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft

  105 Hicks Ave, Bennington, VT 05201

  Opportunity awaits at this unique property with an exceptional setting along the Walloomsac River. A true Vermont farmhouse offering three bedrooms and two bathrooms, situated on a flat, park-like lot with mature landscaping, open green space, and beautiful river frontage. The serene setting creates a peaceful atmosphere rarely found in properties with such versatile potential. A large barn

  Angela Bevin Maple Leaf Real Estate

  105 Hicks Ave, Bennington, VT 05201
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  /42

  $3,900,000

  • 5 Beds
  • 7 Baths
  • 11,736 Sq Ft

  2236 River Rd, Manchester, VT 05254

  Set on more than 18 picturesque acres along desirable River Road in Manchester Village, this extraordinary, converted farm offers a rare blend of historic character, modern comfort, & endless possibilities. Thoughtfully transformed into a multi-use residential compound, the property features four distinct living, working, & entertaining spaces, each with its own personality and purpose.

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

  2236 River Rd, Manchester, VT 05254
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  /4

  $80,000

  • 4 Beds
  • 2 Baths
  • 1,465 Sq Ft

  107 Lyons St, Bennington, VT 05201

  Situated on a peaceful dead-end street, this home offers tremendous potential for investors, contractors, or buyers looking to create their dream home. The property features 3 bedrooms, with the possibility of a fourth, along with 2 bathrooms, providing a highly desirable layout and ample living space. With some vision, care, and updates, this home can be transformed into a beautiful residence in

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  107 Lyons St, Bennington, VT 05201
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  /34

  $875,000

  • 4 Beds
  • 2.5 Baths
  • 2,746 Sq Ft

  2436 Mad Tom Rd, East Dorset, VT 05253

  Picture yourself on 12 private wooded acres along one of Vermont's most scenic country roads in a classic 4-bedroom, 3-bath Colonial offering the perfect blend of comfort, character, and outdoor adventure. Built in 1977 and thoughtfully maintained, the home welcomes you with warm hardwood floors, a beautifully renovated kitchen featuring soapstone countertops, abundant cabinetry, and a sunny

  Gregory Cutler Four Seasons Sotheby's Int'l Realty

  2436 Mad Tom Rd, East Dorset, VT 05253
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  /54

  $460,000

  $35K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,312 Sq Ft

  498 Townline Rd, Bennington, VT 05201

  If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the

  Betty McEnaney Diamond Realty

  498 Townline Rd, Bennington, VT 05201
• 

  

  /23

  $269,000

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft

  1806 Bosley Hill Rd, Readsboro, VT 05350

  This Contemporary Chalet sit on a quiet rural town maintained road.The property is a tasteful blend of woodland and grassy yard with gardens. You can enter from the garage ,above ground , and walk up an interior staircase to the the next level. There is also a half bath and laundry room and plenty of room for side-by-sides, snowmobiles and seasonal gear!On the second level there is a very

  Janet Boyd Boyd Real Estate

  1806 Bosley Hill Rd, Readsboro, VT 05350
• 

  

  /50

  $745,000

  $30K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,220 Sq Ft

  392 Powderhorn Rd, Manchester Center, VT 05255

  Set on two private acres in a desirable Manchester location, this renovated four-bedroom, three-bath Colonial balances privacy and convenience with easy access to both Manchester and Dorset. Wide-plank pine floors, abundant natural light, and inviting living spaces define the interiors.The main level features a spacious living room anchored by a stone fireplace, a formal dining room, and

  Alexandra Crowley Four Seasons Sotheby's Int'l Realty

  392 Powderhorn Rd, Manchester Center, VT 05255
• 

  

  /60

  $995,000

  • 5 Beds
  • 5 Baths
  • 4,126 Sq Ft

  238 Seminary Ave, Manchester, VT 05254

  Manchester Village LivingExperience the charm of village life in this expansive Victorian home and guest cottage, ideally located in the heart of Manchester Village. Rich in character and architectural detail, the home features original woodwork, soaring ceilings, generously sized rooms, and timeless New England appeal—enhanced by a new roof, windows and heating system.The spacious main

  

  Margretta Fischer

  Wohler Realty Group

  238 Seminary Ave, Manchester, VT 05254
• 

  

  /38

  $299,000

  $26K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,829 Sq Ft

  89 Merson St, Woodford, VT 05201

  Welcome to 89 Merson Street! This charming Cape style home offers 3 bedrooms, 1 full bathroom and a half bathroom, and nearly an acre of land on a quiet in town street. Inside, you’ll find beautifully refinished hardwood floors, an updated kitchen, a spacious family room with a fireplace, and a new Weil-McLain boiler installed in February 2026.What truly sets this property apart is its

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  89 Merson St, Woodford, VT 05201
• 

  

  /52

  $299,000

  $10K PRICE INCREASE

  • 3 Beds
  • 1.5 Baths
  • 1,411 Sq Ft

  262 Union St, Bennington, VT 05201

  Just a short walk to downtown shopping and dining you can move right into this well-maintained and thoughtfully updated 3-bedroom, 2-bath home offering comfortable living spaces, modern conveniences, and plenty of room to spread out both inside and out.The heart of the home is the spacious, updated kitchen featuring a center island, abundant counter top space, and generous cabinetry, and even

  William Paquin Maple Leaf Real Estate

  262 Union St, Bennington, VT 05201

Showing Results 81 - 120, Page 3 of 7