Bennington County VT Homes for Sale

/7
$175,000
- Land
- 15 Acres
- $11,298 per Acre
00 Silk Rd, Bennington, VT 05201

Fifteen and a half level, mowed acres, suitable for a home build, agriculture, or a small subdivision.Passing over the iconic Silk Road Covered Bridge crossing the Walloomsac River, on the right you'll find this flat, cleared parcel ready for farming or development. With over 500 feet of road frontage, plenty of acreage, and the beautiful river across the street, the possibilities here

David White OwnerEntry.com

00 Silk Rd, Bennington, VT 05201
/25
$1,274,999
- 4 Beds
- 2.5 Baths
- 4,620 Sq Ft
139 Village View Rd, Manchester, VT 05255

Enjoy privacy and panoramic views of Mount Equinox and the Manchester Valley from this spacious, light-filled home in a desirable location. The main level features a vaulted great room, eat-in kitchen with adjacent covered porch, dining room, den with fireplace, two bedrooms, a full bath, and a primary suite with walk-in shower and jetted tub. Step out onto the expansive deck and take in the

Marek Kovac TPW Real Estate

139 Village View Rd, Manchester, VT 05255
/22
$225,000
- 6 Beds
- 2 Baths
- 2,116 Sq Ft
6967 Main St, Readsboro, VT 05350

Charming, well maintained 1870 duplex in the heart of Readsboro. Each bright spacious unit features a living room, large kitchen, three bedrooms, and bath. The level backyard offers room for gardening. The shed provides additional space for storage. The covered front porch is a wonderful place to relax. With separate utilities for each unit, this property is easy to manage. Conveniently located

Cassandra Ehrlich BHG Masiello Brattleboro

6967 Main St, Readsboro, VT 05350
/22
$995,000
- 4 Beds
- 5.5 Baths
- 4,213 Sq Ft
262 Powderhorn Rd, Manchester Center, VT 05255

Stunning Contemporary Retreat with Indoor Pool on Nearly 2 AcresWelcome to this beautiful 5-bedroom, 5-bath contemporary home nestled on a sunny 1.9+/- acre lot. Designed for both comfort and style, this expansive residence features a 16' x 32' heated indoor swimming pool, perfect for year-round enjoyment.Originally built in 1973 and extensively renovated in 2000, the home blends timeless

Andrea Kaplan Four Seasons Sotheby's Int'l Realty

262 Powderhorn Rd, Manchester Center, VT 05255
/52
$199,000
- 3 Beds
- 2 Baths
- 1,600 Sq Ft
130 Morgan St, Bennington, VT 05201

200 feet of Walloomsac River front .There is a second kitchen for a possible in-law or AB&B. RV parking for those visitors who travel listing to the sounds of the stream for the nomadic visitors. New replacement windows were just done. Bring your imagination and see the possibilities.

Dan Mason Perrott Realty

130 Morgan St, Bennington, VT 05201
/21
$370,000
- 3 Beds
- 1.5 Baths
- 1,116 Sq Ft
6 Deep Woods Rd, Winhall, VT 05255

Escape to your cozy log ski chalet nestled on a private acre in the charming town of Winhall, Vermont! This delightful 3-bedroom, 1.5-bath home offers 1116 square feet of rustic charm and modern comfort. Imagine returning from a thrilling day on the slopes of nearby Stratton or Bromley, just a short drive away, and unwinding by the crackling outdoor fireplace on your spacious patio, with festive

Robin Apps Four Seasons Sotheby's Int'l Realty

6 Deep Woods Rd, Winhall, VT 05255
/45
$1,150,000
- 4 Beds
- 3.5 Baths
- 3,274 Sq Ft
152 Bonnet St, Manchester Center, VT 05255

At 152 Bonnet Street, history holds the walls and craftsmanship tells a story. Built in 1890 and once home to Brewster Antiques, this stately in-town Victorian has stood as a cornerstone of Manchesters architectural heritage for over a century. Thoughtfully renovated from top to bottom, the home honors its vintage soul while embracing modern comfort. Graceful period millwork, preserved original

Hayleyanne Van Der Kar Four Seasons Sotheby's Int'l Realty

152 Bonnet St, Manchester Center, VT 05255
/3
$19,000
- Land
- 1.66 Acres
- $11,446 per Acre
lot 92 Alpendorf Ave, Readsboro, VT 05350

Discover your own piece of Vermont paradise in this picturesque building lot. Surrounded by the scenic Green Mountains with stunning views, this peaceful setting is perfect for your dream home or getaway. Located near top ski areas and just a short drive to North Adams, MA, enjoy easy access to cultural attraction like MASS MoCA. Embrace the tranquility of nature while staying close to outdoor

Christine Girard STEEPLEVIEW REALTY - N. ADAMS

lot 92 Alpendorf Ave, Readsboro, VT 05350
/60
$285,000
- 3 Beds
- 2 Baths
- 1,794 Sq Ft
313 Tunnel St, Readsboro, VT 05350

Seller is motivated! Step into the timeless charm of this lovingly maintained 1900s home, nestled on a peaceful .88-acre lot with Deerfield river frontage. Located in the heart of Readsboro, this 3-bedroom, 2-bathroom residence blends historic character with modern updates, which include new first and second floor windows (2024), a new furnace (2024), and a freshly renovated second floor that is

Flex Realty Group Flex Realty

313 Tunnel St, Readsboro, VT 05350
/40
$1,800,000
- 5 Beds
- 4.5 Baths
- 3,436 Sq Ft
59 Church St, Dorset, VT 05251

Exceptional Dorset Church St. offering. Spacious c 1850s Italianate with Greek Revival features in remarkable condition with new roof, windows, refinished floors, A/C. Spacious, bright eat-in kitchen large parlor living room with fireplace, dining room. First floor master suite, bright well-appointed eat-in kitchen and updated bathrooms. 4-5 bedrooms, Large level yard, stone walled terraces

R. Diedrich August Wohler Realty Group

59 Church St, Dorset, VT 05251
/58
$1,550,000
- 5 Beds
- 3 Baths
- 4,342 Sq Ft
93 Hard Farm Rd, Manchester Center, VT 05255

EARTH WIND AND SHIREHaving caught your breath from the view in the approach, and treading the elegant slate path into the home, you probably won't want to get past the "basking parlor", a room designed for sheer joy in the present moment, made compelling by the wall of windows and the perfectly proportioned design and vaulted ceiling. However, the delights in every room beckon: next is the

Lawrence Zupan EXP Realty

93 Hard Farm Rd, Manchester Center, VT 05255
/51
$970,000
- 6 Beds
- 8 Baths
- 5,764 Sq Ft
24 Vt Route 11, Londonderry, VT 05148

Step into a world of potential with this beautiful country retreat, set on the edge of pristine Green Mountain National Forest. Adventure truly begins here, with nearby access to the Catamount Trail and four renowned ski areas just minutes away. Once home to the beloved Nordic Inn, this versatile property carries a rich legacy of hospitality, having once hosted a restaurant and cross-country ski

Nancy Jensen Four Seasons Sotheby's Int'l Realty

24 Vt Route 11, Londonderry, VT 05148
/54
$1,995,000
- 3 Beds
- 3 Baths
- 5,228 Sq Ft
2167 Myers Rd, Shaftsbury, VT 05262

Welcome to Hidden Ponds Farm!!! Nestled amidst 40 sprawling acres, this historic early 1800's post and beam converted barn is a rare gem combining rustic charm with modern comforts. The property is highlighted by a stunning 1,000-foot hand-placed stone wall, two picturesque ponds, and two orchards offering seasonal beauty and fresh fruit. The expansive outdoor space also features a hot tub,

Kelley Mccarthy Mahar McCarthy Real Estate

2167 Myers Rd, Shaftsbury, VT 05262
/39
$299,000
- 5 Beds
- 2.5 Baths
- 2,735 Sq Ft
30 River Rd, Arlington, VT 05250

300 feet of Batthenkill River front this 3 bedroom 2 bath Colonial with a 2 bed 1 bath in-law wing with an idyllic sound of the River. Enjoy the custom built fire pit to the sound of the river in the evenings and kayaking by day. The 1.5 acre lot has plenty room for gardening or just to spread out a bit. Come see what Southern VT has to offer.

Dan Mason Perrott Realty

30 River Rd, Arlington, VT 05250
/42
$310,000
- 2 Beds
- 2 Baths
- 1,624 Sq Ft
516 Oberdorf Rd, Readsboro, VT 05350

Outdoor lover’s paradise in Alpenwald Village! This beautifully updated 2-bedroom, 2-bath home sits on an ample 2.5 acres and abuts National Forest land—perfect for year-round adventure. Step inside to your open kitchen and a bright family room with cathedral ceilings and a sliding door that opens to a peaceful back porch with stunning mountain views. The spacious mudroom offers plenty of room

Lindsey Martin Maple Leaf Realty

516 Oberdorf Rd, Readsboro, VT 05350
/47
$299,900
- 4 Beds
- 2.5 Baths
- 2,404 Sq Ft
120 Imperial Ave, Bennington, VT 05201

Nestled in the charming village of Bennington, Vermont, this stately 4-bedroom, 2.5-bath home blends timeless elegance with thoughtful updates. Built in 1895 and set on 0.41 acres, the property offers a rare combination of historic character and modern livability. A large Trex front deck with handicap accessible ramp to the front and kitchen doors welcomes you to the home, where you'll find

Kelley Mccarthy Mahar McCarthy Real Estate

120 Imperial Ave, Bennington, VT 05201
/50
$1,275,000
- 4 Beds
- 5 Baths
- 3,610 Sq Ft
3360 Dorset Rd W, Dorset, VT 05251

Exceptional Dorset Contemporary with Classic Craftsmanship & Modern ComfortsSet on 1.86 peaceful acres abutting Dorset Field Club property, this beautifully maintained four-bedroom, five-bath contemporary home offers privacy, elegance, and an ideal Vermont lifestyle. Surrounded by nature and just moments from Dorset Village, this property blends timeless design with thoughtful updates,

David Halligan Four Seasons Sotheby's Int'l Realty

3360 Dorset Rd W, Dorset, VT 05251
/22
$215,000
- 1 Bed
- 1 Bath
- 644 Sq Ft
67 Bourn Brook Rd Unit 55, Manchester Center, VT 05255

Welcome to this beautifully updated one-bedroom upstairs unit that’s move-in ready and packed with value. Freshly painted with stylish vinyl plank flooring throughout, this home shines with natural light and thoughtful upgrades—including brand new kitchen counters and a new hot water tank.Enjoy the ease of low-maintenance living! The association handles trash service, snow removal,

Faith Rhodes Maple Leaf Realty

67 Bourn Brook Rd Unit 55, Manchester Center, VT 05255
/9
$65,000
- Land
- 0.74 Acre
- $87,838 per Acre
0 Stratton View Rd, Winhall, VT 05340

Stratton View Rd Lot # 58 , .74 +- acres wooded parcel. Just 3 minutes to Stratton access road. Minutes to the snow making pond, great for walking and a dip in. the summer. There are 3 ski resorts with in 15 minutes as well as Manchester for shopping and dining. Addition Lot MLS #5036984 available. Own your piece of Vermont.

Mike England Michael England Real Estate

0 Stratton View Rd, Winhall, VT 05340
/13
$135,000
- Land
- 1.36 Acres
- $99,265 per Acre
0 Stratton View Rd, Winhall, VT 05340

Stratton View Road lives up to its name. Big Views of Stratton, just 3 minutes to Stratton access road. Minutes to the snow making pond, great for walking and a dip in. the summer. There are 3 ski resorts with in 15 minutes as well as Manchester for shopping and dining. Own your piece of Vermont.

Mike England Michael England Real Estate

0 Stratton View Rd, Winhall, VT 05340
/8
$65,000
- Land
- 1.02 Acres
- $63,725 per Acre
0 Stratton View Rd, Winhall, VT 05340

Stratton View Rd Lot # 59 , 1.02 +- acres wooded parcel. Just 3 minutes to Stratton access road. Minutes to the snow making pond, great for walking and a dip in. the summer. There are 3 ski resorts with in 15 minutes as well as Manchester for shopping and dining. Addition lot MLS #5036988 available. Own your piece of Vermont.

Mike England Michael England Real Estate

0 Stratton View Rd, Winhall, VT 05340
/60
$1,100,000
- 6 Beds
- 5 Baths
- 5,298 Sq Ft
50 Stratton View Rd, Winhall, VT 05340

Custom built six-bedroom home on 2 acres with spectacular views of Stratton Mountain. The kitchen has granite countertops and custom cabinets with the dining area nearby with plenty of space to accommodate a large gathering. The living area has a cathedral ceiling with large windows for an abundance of natural light and stunning year-round views of Stratton Mountain, with a lovely stone fireplace

Mike England Michael England Real Estate

50 Stratton View Rd, Winhall, VT 05340
/2
$199,500
- Land
- 47 Acres
- $4,245 per Acre
TBD Myers Rd, Shaftsbury, VT 05262

47+/- magical acres of rolling meadows, mountain views, hard woods and wildlife. The acreage affords you the opportunity to build your dream home/mini farm. The expansive acreage invites you to explore the surrounding nature, whether it's a morning walk on the bucolic rural road, greeting the early birds or sitting high on the hillside staring at the stars. Few parcels of this size remain

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

TBD Myers Rd, Shaftsbury, VT 05262
/43
$2,375,000
- 4 Beds
- 4.5 Baths
- 5,696 Sq Ft
376 Windward Hill, Dorset, VT 05251

Welcome to 376 Windward Hill, a stunning Southern Vermont estate with breathtaking views of the Taconic and Green Mountain Ranges. Spanning 12 acres, the property features a private trout pond and tranquil waterfall, creating a serene atmosphere.Inside, the home combines timeless elegance with modern comfort. Herringbone brick and hardwood floors lead to the expansive living room, highlighted

Andrea Kaplan Four Seasons Sotheby's Int'l Realty

376 Windward Hill, Dorset, VT 05251
/39
$297,500
- 5 Beds
- 2 Baths
- 2,294 Sq Ft
218 Union St, Bennington, VT 05201

Charming Downtown Victorian - Income Opportunity Meets Timeless StyleTucked behind the classic facade of this downtown Bennington gem lies an incredible opportunity-for homeowners and investors alike. Located in the heart of downtown on a street known for both professional and residential appeal, this Victorian-style duplex offers versatility, character, and reliable income potential. Each

Kelley Mccarthy Mahar McCarthy Real Estate

218 Union St, Bennington, VT 05201
/12
$575,000
- 6 Beds
- 4 Baths
- 15,179 Sq Ft
423 Main St, Bennington, VT 05201

Historic building in heart of downtown Bennington with solid income from existing commercial tenancy and a fantastic second floor begging to be utilized as residential space. This loft type space is approx. 8,000 sq. ft. and would be an amazing living space (or several) with varying exposure, views of mountains in the distance and of the downtown area. The building offers an abundance of indoor

Chris Long BHG Masiello Brattleboro

423 Main St, Bennington, VT 05201
/28
$1,475,000
- 4 Beds
- 2.5 Baths
- 4,634 Sq Ft
1677 Barnumville Rd, Manchester Center, VT 05255

This historic 19th century two-story brick Federal house was originally a popular tavern. It has been completely renovated/updated to serve today's relaxed living while retaining all classic features. A bright kitchen/dining/living great room w/fireplace is the heart of the home. A first-floor master suite includes a spa-like bath w/fireplace. There is an adjacent mudroom entrance with 1/2 bath

R. Diedrich August Wohler Realty Group

1677 Barnumville Rd, Manchester Center, VT 05255
/52
$629,000
- 3 Beds
- 3 Baths
- 1,650 Sq Ft
11 Pond View Rd, Winhall, VT 05340

6/10/25 Brand new exterior deck being installed very soon to enjoy for the rest of the summer! The Intervale community has long been popular for affordability and value. This bright and sunny unit boasts an updated kitchen, primary suite on the main level with updated bath. Mini suite on upper level along with a third bedroom and shared bath with the loft area. Heating system replaced

Terry Hill Berkshire Hathaway HomeServices Stratton Home

11 Pond View Rd, Winhall, VT 05340
/6
$495,000
- Land
- 7 Acres
- $71,429 per Acre
lot#2 Margeaux Ln, Stratton, VT 05155

This stunning 6.93-acre parcel offers the perfect setting to build the home of your dreams, just moments from the Sun Bowl at Stratton. Nestled in a serene wooded landscape, the property provides both privacy and tranquility while being ideally located for easy access to all that Stratton has to offer. With a septic permit already approved for a 4-bedroom home, this lot is ready for you to begin

Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

lot#2 Margeaux Ln, Stratton, VT 05155
/5
$465,000
- Land
- 6 Acres
- $83,935 per Acre
Lot #4 Margeaux Ln, Stratton, VT 05155

Nestled along a peaceful babbling brook, this 5.54-acre parcel offers an idyllic setting for building the home of your dreams. Surrounded by a serene wooded landscape, the property provides both privacy and tranquility, while still being just moments from the Sun Bowl at Stratton. With a septic permit already approved for a 4-bedroom home, this lot is ready for construction, allowing you

Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

Lot #4 Margeaux Ln, Stratton, VT 05155
/4
$225,000
- Land
- 1.99 Acres
- $113,065 per Acre
00 Margeaux Ln, Stratton, VT 05155

This beautiful 1.99-acre parcel, nestled in the woods, offers the perfect setting to build the home of your dreams. With a 5-bedroom septic permit already in place, you’ll be ready to start construction right away. Access is easy via a right-of-way from Margeaux Lane, providing both privacy and convenience. Located just minutes from the Sun Bowl at Stratton. It is close to everything Stratton

Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

00 Margeaux Ln, Stratton, VT 05155
/40
$305,000
- 3 Beds
- 3.5 Baths
- 3,023 Sq Ft
872 Barber Pond Rd, Pownal, VT 05261

Tucked away in a peaceful Vermont setting, this charming ranch-style home blends rustic charm with modern comfort. Step inside to gleaming hardwood floors, soaring cathedral ceilings, and a cozy brick fireplace, creating an inviting space to relax and unwind. The open kitchen and dining area make mealtime effortless, with easy access to the backyard for summer barbecues or quiet morning coffee on

Nick Sicard EXP Realty

872 Barber Pond Rd, Pownal, VT 05261
/22
$665,000
- 2 Beds
- 2 Baths
- 1,036 Sq Ft
43 Middle Ridge Rd Unit 311, Winhall, VT 05155

Exceptional 2 bedroom /2 bath Rising Bear Unit with Viking Kitchen, propane fireplace and private covered deck. Amenities abound with underground heated parking, year round private outdoor heated pool, sauna and spas. Enjoy private shuttle from the elevator to the Base Lodge during the winter, yet just a short stroll across the Commons into the Village for dining and shopping! Granite

Kim Morgan-Wohler Wohler Realty Group

43 Middle Ridge Rd Unit 311, Winhall, VT 05155
/53
$799,000
- 3 Beds
- 3 Baths
- 2,118 Sq Ft
A6 Ridge Unit A6, Winhall, VT 05340

It’s the Premier Location and commanding views that set this Piper Ridge townhome apart. The stunning unobstructed views are central to thetownhomes design, while the southern exposure provides all day sunshine and a light and airy atmosphere. You’ll experience the evening’s magic watching stunning sunsets with the resort lights on full display and will have the premier “front row seats” to

Karin Hardy Berkshire Hathaway HomeServices Stratton Home

A6 Ridge Unit A6, Winhall, VT 05340
/31
$975,000
- 4 Beds
- 4.5 Baths
- 2,658 Sq Ft
73 Cranberry Hill Rd, Winhall, VT 05340

Nestled at the end of a quiet road in the highly sought-after Strattonwald community, 73 Cranberry Hill Road is the quintessential European-style ski house, offering the perfect Vermont retreat. This impeccably upgraded home has never been rented and is turn-key, ready for immediate enjoyment. It combines timeless charm with modern conveniences, featuring air conditioning for year-round comfort.

Carrie Mathews Winhall Real Estate

73 Cranberry Hill Rd, Winhall, VT 05340
/26
$410,000
- 4 Beds
- 1.5 Baths
- 1,344 Sq Ft
2 Lower Stratton Valley Rd, Winhall, VT 05340

Welcome to this charming ski chalet situated in close proximity to three major ski resorts and offered fully furnished so you can move right in, unpack, and start enjoying yourself. There's a full bath downstairs to go along with 4 generously sized bedrooms and a 1/2 bath upstairs for guests, creating a cozy and inviting atmosphere that's ideal for apres-ski relaxation or a peaceful retreat

Mike Masters Four Seasons Sotheby's Int'l Realty

2 Lower Stratton Valley Rd, Winhall, VT 05340
/43
$2,500,000
- 5 Beds
- 7 Baths
- 7,625 Sq Ft
19 Old Town Rd, Bondville, VT 05340

Experience Vermont luxury at 19 Old Town Road, Winhall—a stunning 5-bedroom, 7-bathroom estate on 21.53 private acres. Built in 2000, this meticulously designed retreat offers unobstructed views of both Stratton Mountain and Magic Mountain.The spacious great room is the heart of the home, featuring soaring ceilings, a grand stone fireplace, and walls of windows that frame breathtaking

Christiane Carroccio TPW Real Estate

19 Old Town Rd, Bondville, VT 05340
/7
$242,000
- Land
- 5 Acres
- $45,234 per Acre
01 Old Depot Rd, West Arlingtn, VT 05250

This 5+ acre open field lot features big sky views of both the Taconic and Green Mountains. Overlooking a privately maintained pond, this property is just down the road from one of Southern Vermont's most charming farms. Comes with an approved wastewater permit for a 4 bedroom home.

Paul Carroccio TPW Real Estate

01 Old Depot Rd, West Arlingtn, VT 05250
/20
$215,000
- Land
- 4.46 Acres
- $48,206 per Acre
OA E Manchester Rd, Manchester, VT 05255

Very desirable lot off East Manchester Road with several building possibilities. Gently sloping, preliminary septic permit in place and access to all Manchester has to offer.

Peter Pierce EXP Realty

OA E Manchester Rd, Manchester, VT 05255
/47
$649,000
- 5 Beds
- 3 Baths
- 3,836 Sq Ft
162 Highland Ave, Manchester Center, VT 05255

Easy Investment Opportunity! Three unit multi-family. Great passive income. Turn key money maker! Spacious layout with privacy for each unit. The main level unit offers an open living dining area, three bedrooms, one-bath with mountain views off the spacious deck. The second floor offers two separate one-bedroom, one-bath units. Each unit has its own entrance. The lower level provides storage for

Margretta Fischer Wohler Realty Group

162 Highland Ave, Manchester Center, VT 05255

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.