Bennington County VT Homes for Sale

/27
$375,000
- Land
- 53 Acres
- $7,075 per Acre
0 Rock Bottom Ln, Peru, VT 05152

Discover the perfect canvas for your dream retreat on this stunning 53-acre parcel in picturesque Peru, Vermont. Tucked away in the Green Mountains, this exceptional property offers expansive views—including a breathtaking sightline to Magic Mountain—and the serenity of true Vermont wilderness.A private driveway is already in place, making access simple and setting the stage for your future home

David Shehadi Josiah Allen Real Estate, Inc.

0 Rock Bottom Ln, Peru, VT 05152
/35
$269,900
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
115 Jefferson Ave, Bennington, VT 05201

Located in a charming Bennington neighborhood, this home offers both convenience and comfort, with shopping, schools, the post office, and the hospital just a short distance away. The welcoming three-season front porch is perfect for enjoying your morning coffee or winding down after a long day. Inside, the spacious, eat-in kitchen has brand-new flooring and newer appliances, adding a fresh and

Kelley Mccarthy Mahar McCarthy Real Estate

115 Jefferson Ave, Bennington, VT 05201
/6
$389,500
- Land
- 8 Acres
- $46,815 per Acre
X Mount Aeolus Rd, Manchester, VT 05255

Time to build your dream home … 8.32+/- acre lot in prime Manchester location with over 1300 feet of Battenkill River frontage; West Branch. Open meadow with mountain views, wastewater permit in place for a four-bedroom home on 6.34 acres (Parcel B) of total acreage and a second 2+/- acre lot, with 3 bedroom permit (Parcel A) for future expansion. Parcels A & B are naturally divided by the river

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

X Mount Aeolus Rd, Manchester, VT 05255
/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 are

David White OwnerEntry.com

00 Silk Rd, Bennington, VT 05201
/22
$30,000
- 2 Beds
- 2 Baths
- 938 Sq Ft
35 West Rd, Bennington, VT 05201

Lovingly cared for by a single family since it was built in 1986, this well-maintained single wide is ready to welcome its next chapter—and new owners. Conveniently located just 7 minutes from downtown Bennington and moments from the Monument Arts Center, this home offers both comfort and accessibility. Situated on the first lot in the park, you’ll enjoy stunning mountain views right from the

Thomas Martins Maple Leaf Realty

35 West Rd, Bennington, VT 05201
/35
$425,000
- 3 Beds
- 1.5 Baths
- 1,832 Sq Ft
1283 Hidden Valley Rd, Shaftsbury, VT 05262

Welcome to the one you’ve been waiting for in sought after Shaftsbury! This beautifully updated, low-maintenance Colonial offers comfort, style, and space, inside and out. Step into a freshly painted interior where thoughtful updates shine throughout. The heart of the home is the spacious kitchen, featuring all new appliances, gleaming granite countertops, and abundant cabinetry, perfect for

Angela Bevin Maple Leaf Realty

1283 Hidden Valley Rd, Shaftsbury, VT 05262
/44
$340,000
- 4 Beds
- 2.5 Baths
- 2,248 Sq Ft
197 Crescent Blvd, Bennington, VT 05201

Welcome to your ideal in-town residence! This beautifully maintained 4-bedroom, 2.5-bath home offers the perfect blend of space, comfort, and convenience—located just a few blocks from downtown dining, shops and festivals. Step through the enclosed breezeway from your attached garage to find a bright and inviting floor plan featuring a generously sized living room and formal dining room with

Cassie Barbeau Mahar McCarthy Real Estate

197 Crescent Blvd, Bennington, VT 05201
/26
$199,900
- 3 Beds
- 1.5 Baths
- 1,632 Sq Ft
305 Weeks St, Bennington, VT 05201

Located in a sought-after area, this Tri-level townhouse style condo is situated close to Main Street shops, bars, and restaurants, as well as the hospital, rec center, neighborhood markets, and the bus station. The first floor boasts an open floor plan with a unique kitchen that retains its original charm. Highlights include a center brick chimney, island w/ breakfast bar, quartz and butcher

Matt Waddington Hoffman Real Estate

305 Weeks St, Bennington, VT 05201
/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
/8
$575,000
- Land
- 12 Acres
- $47,917 per Acre
TBD Tower Rd, Dorset, VT 05251

Last Dorset hollow Corporation lot to be publicly available. 12 Ac. at end of Tower Rd. (beyond juncture of upper and lower Hollow RD. at water wheel). Lot on right past Grouse lane. Building site elevated level plateau affording views to south and east. Dorset Hollow Corp. (DHC) was created in 1968 to save over 500 acres from becoming a major ski area with intense development. This lot D-5 is

R. Diedrich August Wohler Realty Group

TBD Tower Rd, Dorset, VT 05251
/47
$165,000
- 4 Beds
- 3 Baths
- 2,094 Sq Ft
136 Mccall St, Bennington, VT 05201

Investment opportunity! Three units with strong rental history. Recent renovation of the main foyer with fresh paint and new vinyl plank flooring. The two-story front section features original details including natural woodwork, large windows, and winding staircase. Concrete basement is set up for shared laundry (coin-op washer does not work, new dryer) and all utilities (oil tank, Weil

Jenifer Prouty Hoffman Hoffman Real Estate

136 Mccall St, Bennington, VT 05201
/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 Open Sat 11AM - 1PM
- 5 Beds
- 4.5 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
/22
$285,000
- 3 Beds
- 2 Baths
- 1,332 Sq Ft
18 Stratton Ridge Rd, Winhall, VT 05340

Welcome to 18 Stratton West Road – a charming 3-bedroom, 2-bath ski condo located just minutes from Stratton Mountain Resort. This spacious unit features over 1,300 square feet of well-maintained living space, complete with a cozy wood-burning fireplace, updated bathrooms, and generous natural light throughout. The open-concept layout is perfect for entertaining, with a functional kitchen, dining

Derek Greene Derek Greene

18 Stratton Ridge Rd, Winhall, VT 05340
/3
$25,000
- Land
- 1.66 Acres
- $15,060 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
$309,000
- 3 Beds
- 2 Baths
- 1,794 Sq Ft
313 Tunnel St, Readsboro, VT 05350

Step into the timeless charm of this lovingly maintained 1900s home, nestled on a peaceful .88-acre lot with river frontage. Located in the in the heart of Readsboro, this 3-bedroom, 2-bathroom residence effortlessly blends historic character with modern updates, offering the perfect retreat for full-time living or a seasonal getaway. Inside, you'll find spacious rooms filled with natural light,

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 Federal in remarkable condition with new roof, windows, refinished floors, large dining room, parlor and living room with fireplace. First floor master suite, bright well-appointed eat-in kitchen and updated bathrooms. 4-5 bedrooms, Large level yard, stone walled terraces front and back, attached garage. New mini split AC on second

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 eat-in

Lawrence Zupan EXP Realty

93 Hard Farm Rd, Manchester Center, VT 05255
/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
/35
$289,000
- 3 Beds
- 2 Baths
- 1,740 Sq Ft
65 Mountain View Dr, Shaftsbury, VT 05262

3 bed 2 bath ranch with great views of the Green Mountain Range in a country setting in the Shaftsbury School District. Double flue chimney ready for a secondary heat source.

Dan Mason Perrott Realty

65 Mountain View Dr, 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
/6
$35,000
- Land
- 1.70 Acres
- $20,588 per Acre
159 Oberdorf Rd, Readsboro, VT 05350

Escape to the mountains with this ready-to-build 1.7-acre lot in scenic Alpenwald Village! Nestled beside National Forest land and bordered by a charming brook along the northern edge, this property offers a peaceful natural setting with endless outdoor adventure at your doorstep. Enjoy direct access to VAST snowmobile and VASA ATV trails, nearby hiking and mountain biking, and Dutch Hill for

Lindsey Martin Maple Leaf Realty

159 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
/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, exterior

Faith Rhodes Maple Leaf Realty

67 Bourn Brook Rd Unit 55, Manchester Center, VT 05255
/10
$135,000
- Land
- 5 Acres
- $26,892 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
/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
/17
$4,000,000
- Land
- 136 Acres
- $29,326 per Acre
15 Wind Hill Rd, Manchester Center, VT 05255

A rare offering in the heart of Manchester, Vermont – 136.4 acres of open meadows, hardwood forest, and stunning mountain views. Located at the corner of Wind Hill and North Road, this property features 2 separate dwellings plus outbuildings.

Christiane Carroccio TPW Real Estate

15 Wind Hill Rd, Manchester Center, VT 05255
/46
$269,000
- 4 Beds
- 1 Bath
- 1,875 Sq Ft
4 Pine Rd, Bennington, VT 05201

Motivated seller of this beautifully ranch home on a dead-end road boasts 4 Bedroom. Enjoy the warmth of the sunroom during the day. The living room centered in the middle of the house has plenty of space to spread out and enjoy the pellet stove insert with a brick hearth on those cool nights. Locally crafted Cushman Style cabinet in the dining area with delightful wood cabinets in the kitchen.

Dan Mason Perrott Realty

4 Pine Rd, Bennington, VT 05201
/50
$299,000
- 4 Beds
- 2 Baths
- 1,602 Sq Ft
224 Sycamore Ln, Shaftsbury, VT 05262

This 4 bedroom cape is located on a dead end street in a desirable neighborhood within the village of Shaftsbury. The updated kitchen has a small island and is open to the dining area. The living room has hardwood floors, gas fire place and built-ins along one wall. There is a washer and dryer located on the first floor in the entry hall and a full bath also on this level. There are two

Catherine Cairns Maple Leaf Realty

224 Sycamore Ln, Shaftsbury, VT 05262
/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
/16
$329,000
- 2 Beds
- 1.5 Baths
- 1,152 Sq Ft
89 Field Way, Pownal, VT 05261

Discover your private mountain sanctuary in this charming post-and-beam home with breathtaking views of the Taconic Mountains. Stunning sunrises are visible from the primary bedroom and living area. The versatile loft offers space for a home office, reading nook, or guest accommodation. This unique property seamlessly blends its rustic charm with modern amenities, including solar panels,

Lori Hurley Four Corner Properties LLC

89 Field Way, Pownal, VT 05261
/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

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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.