Bennington County VT Homes for Sale

/54
$1,875,000
- 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
/51
$225,000
- 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 Battenkill River has to offer.

Dan Mason Perrott Realty

30 River Rd, Arlington, VT 05250
/42
$299,000
- 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
/27
$595,000
- 2 Beds
- 2 Baths
- 3,478 Sq Ft
142 Mount Aeolus Rd, Manchester, VT 05255

A Rare Investment Opportunity in Manchester! This versatile property offers the perfect blend of commercial and residential potential, making it an ideal choice for savvy investors or those seeking a live-work setup. The upstairs features a spacious residential rental, while the lower level was recently leased to a local daycare, providing immediate rental income.This well-maintained property

Andrea Kaplan Four Seasons Sotheby's Int'l Realty

142 Mount Aeolus Rd, Manchester, 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
/51
$249,500
- 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
/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
$499,000
- 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
/34
$1,350,000
- 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
/57
$629,000
- 3 Beds
- 3 Baths
- 1,650 Sq Ft
11 Pond View Rd, Winhall, VT 05340

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 with an efficient Buderus boiler. Plenty of room for your weekend guests but a manageable floor plan for

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
/55
$749,000
- 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
$949,000
- 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
/44
$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
/35
$649,000
- 8 Beds
- 3.5 Baths
- 2,520 Sq Ft
405 Vermont 30, Winhall, VT 05340

Ski Resort Investment Gem! 2-Family Home Near Stratton & BromleyRare investment opportunity in the heart of Vermont's premier ski region. Located on scenic Vermont Route 30, this property offers unparalleled access to both Stratton Mountain Resort and Bromley Mountain Ski Resort. Whether you're looking to live in one unit and rent the other, or convert it to a single-family home, this

Robin Apps Four Seasons Sotheby's Int'l Realty

405 Vermont 30, Winhall, VT 05340
/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
$599,000
- 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
/15
$168,000
- Land
- 3.00 Acres
- $56,000 per Acre
530 Finbars Forest Rd, Manchester Center, VT 05255

If you're looking for a distinctive Manchester home site, look no further than this private, wooded lot bordering the back nine of Manchester Country Club's celebrated championship golf course. The south-facing wooded lot offers the perfect blend of privacy, exquisite golf course views, and the distant backdrop of the rolling Green Mountain ridge. The location is as central as it is nestled in

Jamie Luke TPW Real Estate

530 Finbars Forest Rd, Manchester Center, VT 05255
/56
$2,999,000
- 6 Beds
- 6.5 Baths
- 6,650 Sq Ft
25 Mountain Haunts Rd, Winhall, VT 05340

Attend the PUBLIC OPEN HOUSE Monday February 17 from 10:00-2:00. Exceptional 40.8 acre newly expanded and renovated Stratton Mountain estate with unrivaled views of Stratton just minutes from the Base Lodge or Sun Bowl. This is your own personal winter playground where you can hit the slopes or snowmobile and hike on your own land with additional acreage available.This Grand Lodge NOW BOASTS 4

Kim Morgan-Wohler Wohler Realty Group

25 Mountain Haunts Rd, Winhall, VT 05340
/52
$399,900
- 4 Beds
- 2 Baths
- 2,368 Sq Ft
263 Elm St, North Bennington, VT 05257

New Price! Fabulous Four Bedroom Farmhouse. Updated kitchen with new stainless steel appliances. Take in the mountain view through your newer windows over the new stainless steel sink and subway tile backsplash. Natural light graces this spacious home. The first-floor primary bedroom has a private walk-out deck overlooking the large level backyard. The generous living room opens up to a dining

Margretta Fischer Wohler Realty Group

263 Elm St, North Bennington, VT 05257
/15
$195,000
- Land
- 40 Acres
- $4,875 per Acre
0 Alden Ln, Sunderland, VT 05250

Wow! 39+ acres only minutes to Manchester! Trails, privacy and conveniently located. Features mountain vistas and trails to Mill Brook. Rare find and ready for the next owner. No further subdivision.

Margretta Fischer Wohler Realty Group

0 Alden Ln, Sunderland, VT 05250
/15
$670,000
- 5 Beds
- 4 Baths
- 3,732 Sq Ft
105 Elm St, Manchester, VT 05255

This 4 unit multi family property located in Manchester's Depot district has been owned and managed by the same partnership group for over 30 years. The property is fully occupied with good tenants and is in excellent condition. There are two apartments on the first floor and two apartments on the second floor. There is ample of off street parking behind the building. There is coin operated

David Citron RE/MAX Four Seasons

105 Elm St, Manchester, VT 05255
/40
$479,000
- 4 Beds
- 3.5 Baths
- 3,861 Sq Ft
120 Village St, East Dorset, VT 05253

Antique charmer in the village of East Dorset was originally built in the 1850s by famous lumberman, F.G. Harwood. An addition was added in 1900, followed by several improvements over time the colonial farmhouse boasts approximately 3,861 sq. ft. including an oversized two car garage all on 1.1 acres. With a sprawling footprint that features a primary bedroom suite with oversized closet, 4

Jill Simon Josiah Allen Real Estate, Manchester Branch Office

120 Village St, East Dorset, VT 05253
/34
$185,000
- Land
- 3.10 Acres
- $59,677 per Acre
00 Finbar's Forest Rd, Manchester, VT 05255

Set on a knoll. Stunning mountain view of Mt Aeolus. This private 3.1 acre lot is ready to be built on with the driveway installed and lot cleared. Vt State Wastewater permit WW-8-2024 for a 3 bedroom home. Owner has staked the land to show the well and septic location. Newly added topsoil and seeded. Short drive to the center of Manchester and around the corner to the Manchester Country

Patti Trudel RE/MAX Four Seasons

00 Finbar's Forest Rd, Manchester, VT 05255
/18
$29,900
- Land
- 2.34 Acres
- $12,778 per Acre
00 Red Mountain Rd, Arlington, VT 05250

Three Springs Retreat, is a 2.34-acre parcel nestled in the charming town of Arlington, Vermont, offering a serene escape with three flowing brooks in the heart of the Green Mountains. Known for its rich history, Arlington blends small-town charm with vibrant natural beauty, making it an ideal location for outdoor enthusiasts and nature lovers alike. Imagine creating your own personal haven on

Sandy Reavill Real Broker LLC

00 Red Mountain Rd, Arlington, VT 05250
/12
$60,000
- Land
- 11 Acres
- $5,455 per Acre
0 Rupert Rd Unit 5021897, Sandgate, VT 05250

Build your getaway home in the Vermont mountains! Beautiful, secluded lot of varying terrain in Sandgate, Vermont. Close to NY border, 30 minutes to historic Manchester, VT and Bennington, VT, as well as ski mountains. Perc test completed less than a year ago and identified two areas on lot that are usable for septic. Accessible from public road.

Nicholas Charest Maple Leaf Realty

0 Rupert Rd Unit 5021897, Sandgate, VT 05250
/50
$1,050,000
- 5 Beds
- 5.5 Baths
- 4,729 Sq Ft
83 Benson Fuller Dr, Bondville, VT 05340

Just an 8-minute drive to Stratton, 83 Benson Fuller Drive sits atop the beautiful Forest Farms neighborhood, offering both serenity and convenience. This meticulously updated home is ready for you to move in and enjoy the best of Vermont living. Nestled on a quiet dirt road, it’s perfect for morning and evening strolls with the dog before or after a day on the slopes.Inside, this

Christiane Carroccio TPW Real Estate

83 Benson Fuller Dr, Bondville, VT 05340
/40
$1,450,000
- 5 Beds
- 3.5 Baths
- 4,017 Sq Ft
11 Founders Hill Rd, Winhall, VT 05360

Stratton Mountain location for full time or vacation style living! Spacious home that you can walk to Village, gondola, golf and Sports center. Corner lot justdown the street from the Stratton Mountain Club and the Base Lodge. Home has five bedrooms with a chefs kitchen that has Viking Stove, ice-maker and three dishwashers for entertaining guests. Living room and dining room are graced with

Bob Maisey Berkshire Hathaway HomeServices Stratton Home

11 Founders Hill Rd, Winhall, VT 05360
/2
$44,900
- Land
- 1.00 Acre
- $44,900 per Acre
270 Bergabhang Dr, Readsboro, VT 05350

Come and build on this beautiful lot in Alpenwald Village - lot is cleared and is an approved and engineered building lot

Sean Taylor Moresi Real Estate Partners

270 Bergabhang Dr, Readsboro, VT 05350
/37
$569,999
- 4 Beds
- 3 Baths
- 3,504 Sq Ft
636 Tunnel St, Readsboro, VT 05350

Almost there! This owner has taken a traditional farmhouse and transformed it into an amazing home full of style and grace. There are many ways to consider this home...over 3500 square feet of single family living with 4 bedrooms (or even 5) and 3 baths...live on one floor, AIR B&B all or part of the other floor....rent both levels and use as a vacation home on off seasons. The kitchen is

Christine Lewis Brattleboro Area Realty

636 Tunnel St, Readsboro, VT 05350
/28
$750,000
- 3 Beds
- 2 Baths
- 2,610 Sq Ft
3622 Dorset West Rd, Dorset, VT 05251

Unique Dorset West Road offering....This rare opportunity beckons creativity, craft, and charm! Begs all those ready, willing and able to renovate, keeping the existing home, whilst enjoying life in an extremely beautiful and desirable location. Enjoy the beautiful framed in mountain views from most interior living spaces and from the back patio/yard. This 6.6 acre rolling property boasts

Sunny Breen Josiah Allen Real Estate, Inc.

3622 Dorset West Rd, Dorset, VT 05251
/9
$72,000
- Land
- 3.50 Acres
- $20,571 per Acre
0 Vermont Route 313 W, Arlington, VT 05250

Welcome to the site of your new home in Arlington! This bucolic property offers views and an ideal rural location right by town. 180-degree views lend sunrise to sunset moments overlooking the surrounding Green Mountains and Battenkill River Valley. Just a 2-mile drive to the center of Arlington, the balance of privacy and proximity could not be better. Design and permit in place for 3-bedroom

Jamie Luke TPW Real Estate

0 Vermont Route 313 W, Arlington, VT 05250
/30
$1,250,000
- 4 Beds
- 2.5 Baths
- 2,400 Sq Ft
77 Fuller Rd W, Bennington, VT 05201

Experience the quintessential Vermont lifestyle at the historic Nickerson-Jewett farm. Only 5 minutes to Bennington attractions and amenities and 15 minutes to Williamstown, MA. This appealing country home is located on a town maintained dead-end road. Privately nestled on 134.46 acres of scenic beauty, the charming 4 bedroom, 2.5 bath mid nineteenth century farmstead includes a well-preserved

Jason Saphire www.HomeZu.com

77 Fuller Rd W, Bennington, VT 05201
/26
$385,000
- Land
- 2.00 Acres
- $192,500 per Acre
100 Back 9 Bluff, Manchester, VT 05255

Discover the perfect blend of convenience and tranquility with this stunning 2-acre lot nestled in the heart of Manchester, VT. Boasting a picturesque landscape with mature trees and scenic views, this property offers more than just land—it comes complete with essential infrastructure for your dream home. This lot is ready to build with a foundation already in place, a well, a septic system, a

David Shehadi Josiah Allen Real Estate, Inc.

100 Back 9 Bluff, Manchester, 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.