Bennington County VT Homes for Sale

/26
$795,000
- 3 Beds
- 3 Baths
- 2,044 Sq Ft
6 Quarter Mile Rd, Winhall, VT 05340

AMAZING LOCATION! Walking distance to Stratton Mountain! This home is located on the shuttle route and being offered fully furnished! Walk to the slopes or just take a nice walk around the local trails. Spacious home with ample room for everyone. The open concept kitchen, dining, living room offers cathedral ceilings and woodburning fireplace. French doors leading out to the firepit area for

Julie Lowe Lowe's Real Estate, LLC

6 Quarter Mile Rd, Winhall, VT 05340
/33
$880,000
- 8 Beds
- 6 Baths
- 4,326 Sq Ft
143 Nichols Rd, Peru, VT 05152

I am writing to share information about a remarkable property in Peru, Vermont, that offers year-round enjoyment.This sun-filled home is situated on 10 acres of land, boasting beautiful mountain views and a private pond complete with a beach, deck, above-ground pool, and a sauna. Imagine swimming, fishing, and hiking in the warmer months, and ice-skating, snowmobiling, and cross-country

Tatsiana Clark Four Seasons Sotheby's Int'l Realty

143 Nichols Rd, Peru, VT 05152
/48
$599,900
- 4 Beds
- 3.5 Baths
- 3,742 Sq Ft
34 Southshire Dr, Bennington, VT 05201

Expansive Ranch on 2.4 Acres in Desirable Southshire Neighborhood – Bennington, VermontSet on a generous 2.4-acre lot in the sought-after Southshire neighborhood, this spacious ranch offers comfortable living with scenic privacy and versatile space. The main level features a well-appointed kitchen that opens to a cozy family room complete with a fireplace and built-in bookshelves, all

Kelley Mccarthy Mahar McCarthy Real Estate

34 Southshire Dr, Bennington, VT 05201
/28
$850,000
- 4 Beds
- 2 Baths
- 1,908 Sq Ft
6 Roundtree Rd, Winhall, VT 05340

Prime Stratton location! This charming 4-bedroom, 2-bathroom retreat offers vaulted ceilings, an open-concept living area with a wood burning fireplace, and a private deck and backyard for relaxing after a day on the slopes. With weekend and holiday shuttle service during ski season, plus easy access to Stratton Village’s shops, dining, and year-round activities, it’s the ideal spot to recharge

Christina Dryden Berkshire Hathaway HomeServices Stratton Home

6 Roundtree Rd, Winhall, VT 05340
/42
$799,000
- 4 Beds
- 3.5 Baths
- 4,508 Sq Ft
308 Mending Walls Rd, Manchester Center, VT 05255

Don't hesitate! Come see this immaculate Country Cape located in the highly sought-after community of Mending Walls in Manchester, Vermont. This well-maintained 2003 home combines timeless charm with modern convenience, offering a perfect blend of cozy living and spacious entertaining areas. Enjoy the luxury of main-level living with a spacious primary suite, offering convenience and privacy. The

Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

308 Mending Walls Rd, Manchester Center, VT 05255
/27
$695,000
- 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
/48
$685,000
- 3 Beds
- 2.5 Baths
- 1,738 Sq Ft
1516 W Mountain Rd, Shaftsbury, VT 05262

Discover your dream retreat in this immaculate 3-bedroom, 3-bath, single level home, nestled on over 4 acres of breathtaking landscape. Enjoy expansive mountain views of the Taconic range, Bennington Monument, and Mount Graylock. Relax on the spacious deck or in the screened-in porch, soaking in the stunning vistas. This updated one-level home, features hardwood floors throughout and an open

Margretta Fischer Wohler Realty Group

1516 W Mountain Rd, Shaftsbury, VT 05262
/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
/37
$599,999
- 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
/27
$599,000
- 4 Beds
- 2.5 Baths
- 3,100 Sq Ft
357 Kansas Rd, East Arlington, VT 05252

Welcome to 357 Kansas Road! This beautiful property seamlessly blends rustic charm with modern amenities. Step onto the inviting covered porch, perfect for relaxing. An expansive great room featuring a massive kitchen island ideal for dining & entertaining. A quiet den flows into a great office space. Enjoy the built-ins of the office that make these spaces both functional & stylish. The main

Andrea Kaplan Four Seasons Sotheby's Int'l Realty

357 Kansas Rd, East Arlington, VT 05252
/28
$825,000
- 5 Beds
- 2 Baths
- 3,500 Sq Ft
20 Bishop Rd, Searsburg, VT 05363

Absolutely amazing long range mountain views over the Green Mountain National Forest, Mount Snow, Haystack, and Stratton, from this beautiful 2020 Moosehead log home. This home sits on 7+ acres with easy access to VAST snowmobile trails, as well as your own property to loop on, but still only a short drive to ski resorts, lakes, and other Vermont destinations. The home has a gorgeous open floor

Adam Palmiter Berkley & Veller Greenwood/Dover

20 Bishop Rd, Searsburg, VT 05363
/9
$649,500 New Construction
- 2 Beds
- 1.5 Baths
- 1,293 Sq Ft
18 Jameson Flats Rd Unit 18, Manchester, VT 05255

THE PROGRAM: Purchase Price Assistance/ Mortgage Payment Reduction:Eligibility Requirements:* Vermont Residency or Residency at time ofPurchase* First Time Vermont Homebuyer* Household Income at or Below $178,735** Qualify for a Bank Mortgage* 10% Down PaymentThe developer will offer Gifted Equity andPaid Points at closing that will reduce thepurchase

Britt Wohler Wohler Realty Group

18 Jameson Flats Rd Unit 18, Manchester, VT 05255
/53
$795,000 Open House 7/12
- 3 Beds
- 3 Baths
- 1,842 Sq Ft
E12 Rock Ridge Rd, Winhall, VT 05155

Move right in and start enjoying the Vermont lifestyle at Piper Ridge E12—an impeccably updated, fully furnished 3-bedroom plus den, 3-bath townhome just minutes from Stratton Mountain. Inside this turnkey home, you'll find bright and welcoming spaces designed for comfort and functionality. Every detail has been thoughtfully considered—a brand-new kitchen, stylishly renovated baths, new flooring,

Cheyanne Pugliese

E12 Rock Ridge Rd, Winhall, VT 05155
/15
$565,000
- 4 Beds
- 3 Baths
- 2,073 Sq Ft
2588 Vermont 11, Peru, VT 05152

On a gentle rise surrounded by 7.5 acres of meadows and woodland, this Vermont style ranch subtly blends an appealing rustic charm with contemporary features. The current owners purchased the property in 2021 for family and friends and installed a new wastewater system, new furnace, new roof section, new appliances. The rough sawn clapboard exterior delineates the enduring character of the house.

Diana Stugger Four Seasons Sotheby's Int'l Realty

2588 Vermont 11, Peru, VT 05152
/34
$299,900
- 3 Beds
- 2.5 Baths
- 1,810 Sq Ft
3530 Vt Route 346, Pownal, VT 05261

This historic house, built in 1880, is nestled in the quiet village of North Pownal. It is situated on a large, level lot and offers the timeless charm of yesteryear. The first floor features a roomy kitchen with Kenmore Plus Stainless-Steel appliances, an open-concept living room and dining room, an updated bathroom, and a convenient first-floor laundry room. The back porch has been partially

Matt Waddington Hoffman Real Estate

3530 Vt Route 346, Pownal, VT 05261
/5
$14,500
- Land
- 1.00 Acre
- $14,500 per Acre
0 Lebenschauung Cir Unit 5049439, Stamford, VT 05352

Top-of-the-World Views Await - One Acre in Southern Vermont Discover your own slice of paradise with this beautiful one-acre wooded lot nestled in Southern Vermont. The current owner hand-picked this lot for its ''top of the world'' feel—and with a little clearing, the panoramic views will be nothing short of breathtaking. This is your chance to escape the hustle and build your dream retreat.

Christine Girard Steepleview Realty

0 Lebenschauung Cir Unit 5049439, Stamford, VT 05352
/6
$14,500
- Land
- 1.20 Acres
- $12,083 per Acre
0 Oberdorf Rd Unit 5049437, Readsboro, VT 05350

Looking for the perfect Vermont escape? This 1.2-acre wooded lot in Alpenwald Village, Stamford, is your ticket to fun and freedom! Nestled in the beautiful Green Mountains, the land is mostly level with a charming creek along the edge—ideal for your dream home or weekend getaway. Just minutes to ski resorts, VAST trails for snowmobiling and ATV adventures, and nearby lakes for boating and

Christine Girard Steepleview Realty

0 Oberdorf Rd Unit 5049437, Readsboro, VT 05350
/31
$799,000
- 3 Beds
- 3 Baths
- 2,317 Sq Ft
9 F Cobble Ridge Rd, Winhall, VT 05340

Step into a lifestyle of luxury and convenience at Piper Ridge D9! This stunning community offers the perfect blend of comfort and excitement, with fantastic amenities like a sparkling swimming pool, tennis courts, a clubhouse for social gatherings, and even a weekend shuttle service in the winter—ideal for enjoying the nearby slopes! Inside the impeccably maintained townhouse, you'll find a cozy

Carrie Mathews Winhall Real Estate

9 F Cobble Ridge Rd, Winhall, VT 05340
/33
$355,000
- 4 Beds
- 2 Baths
- 2,072 Sq Ft
60 Knoll Crest Ln, Bennington, VT 05201

Step into this well maintained brick and clapboard residence, perfectly nestled in a lovely neighborhood. Just minutes from the hospital and a short, pleasant walk to downtown, this home offers the best of both convenience and community.Bathed in natural light, the interior boasts an inviting and functional layout highlighted by gleaming hardwood floors and timeless character throughout.

Moira Spivey Four Seasons Sotheby's Int'l Realty

60 Knoll Crest Ln, Bennington, VT 05201
/25
$319,000
- 3 Beds
- 2.5 Baths
- 1,888 Sq Ft
120 Albe Dr, Bennington, VT 05201

Comfortable, convenient and close to downtown Bennington and all its amenities. Built in 2001, in a quiet neighborhood, the home features 3 bedrooms and 2.5 baths,, which includes a primary suite with its own bath. The first floor offers a spacious eat-in kitchen with washer and dryer efficiently installed in a large closet. The kitchen also has glass doors that open to private deck and a level

Ann Greenwood Alton + Westall Real Estate Agency, LLC

120 Albe Dr, Bennington, VT 05201
/19
$219,500
- 3 Beds
- 1 Bath
- 1,254 Sq Ft
14 Robinson Ave, Bennington, VT 05201

Discover this lovely three-bedroom, one-bathroom home featuring 1,254 square feet of finished space, all set on a .24-acre lot. Recent upgrades roughly in the last ten years include blown-in insulation, roof, furnace, and updated kitchen and flooring, making this home both comfortable and stylish. Perfect for families or anyone looking for a cozy place. Minutes from Mt. Anthony Country Club,

Timothy Corcoran Mahar McCarthy Real Estate

14 Robinson Ave, Bennington, VT 05201
/27
$119,000
- 3 Beds
- 1 Bath
- 1,008 Sq Ft
318 Skyboro Rd, Pownal, VT 05261

Nice 1 acre lot with older mobile home in need of renovations or remove the current home and replace it with a new mobile home. Maybe you have been renting in a park and want to move your home to this lot. It would also make a nice building lot with the drilled well and underground power already in place.The possibilities are endless.

Dan Mason Perrott Realty

318 Skyboro Rd, Pownal, VT 05261
/56
$249,000
- 3 Beds
- 1 Bath
- 1,660 Sq Ft
174 Cleveland Ave, Shaftsbury, VT 05262

Fresh clean ranch ready for your finish touched. This house was just painted and the roof was replaced. Large fenced back yard for pets. The deck id ready for a new pool or just access the backyard for games or leisure. Easy to show and move in ready.

Dan Mason Perrott Realty

174 Cleveland Ave, Shaftsbury, VT 05262
/31
$395,000
- 2 Beds
- 1 Bath
- 1,624 Sq Ft
2374 Shaftsbury Hollow Rd, North Bennington, VT 05257

Escape to peace and privacy in this beautiful 2-bedroom, 1 bath getaway home set on 7.15 picturesque acres, complete with your own private pond and surrounded by majestic mountains. Step inside to an open-concept kitchen, dining, and living area-perfect for entertaining or simply soaking in the serenity. The space is filled with natural light thanks to large windows that frame the stunning views.

Kelley Mccarthy Mahar McCarthy Real Estate

2374 Shaftsbury Hollow Rd, North Bennington, VT 05257
/12
$135,000
- 2 Beds
- 1.5 Baths
- 1,056 Sq Ft
242 North Rd, East Arlington, VT 05252

Calling all investors! This property is situated on a private 1-acre lot in sought-after Sunderland, featuring a calming stream running behind the property. It includes an oversized detached garage with a second floor above that could be converted into additional living space. Close proximity to Manchester, Bromley Mountain, and Stratton Mountain. Sunderland offers school choice for grades

Matt Waddington Hoffman Real Estate

242 North Rd, East Arlington, VT 05252
/3
$525,000
- 3 Beds
- 3 Baths
- 2,935 Sq Ft
3460 Sunderland Hill Rd, Arlington, VT 05250

Charm and character of this 1920 farmhouse with wonderful mountain views and close to Manchester location. Stone fireplace centered in living room,Great room with Vermont castings propane stove. Garage / bard has a great second story with potential for finished guest or studio space.

William Mariano Josiah Allen Real Estate, Inc.

3460 Sunderland Hill Rd, Arlington, VT 05250
/33
$525,000
- 3 Beds
- 1 Bath
- 1,344 Sq Ft
3 Strattonwald Rd, Winhall, VT 05340

Lovingly renovated and move-in ready, this 3-bedroom chalet is your ideal mountain escape in the sought-after Strattonwald neighborhood. Take in beautiful views of Stratton Mountain from the comfort of your home while enjoying the warmth and character of this thoughtfully updated retreat. Inside, you’ll find a brand-new kitchen and updated bathroom, stone wood burning fireplace, gleaming hardwood

Robin Apps Four Seasons Sotheby's Int'l Realty

3 Strattonwald Rd, Winhall, VT 05340
/10
$435,000
- Land
- 25 Acres
- $17,726 per Acre
0 River Rd, Winhall, VT 05340

24+ Acres in Winhall, VT — Private 1+ Acre Pond, River Frontage & Minutes from Stratton | Welcome to a rare opportunity in the heart of Vermont’s Green Mountains — a stunning 24+ acre parcel in Winhall offering a unique combination of convenience, privacy, natural beauty, and year-round adventure, just minutes from Stratton Resort. With a state-issued wastewater permit in place, the land is

Cheyanne Pugliese

0 River Rd, Winhall, VT 05340
/37
$239,900
- 6 Beds
- 2 Baths
- 2,288 Sq Ft
215 Dewey St, Bennington, VT 05201

Beautifully situated in the heart of Bennington, this spacious and sunlit 2,288 sq ft duplex (1,144 sq ft per unit) is the perfect blend of comfort, character, and income potential. Each unit features three generous bedrooms, one full bath, in-unit laundry, and charming hardwood floors in the main living areas. An abundance of windows fills the space with natural light, creating a bright and

Jeffrey Dorman EXP Realty

215 Dewey St, Bennington, VT 05201
/14
$259,000
- 3 Beds
- 3 Baths
- 1,461 Sq Ft
400 South St, Bennington, VT 05201

400 South St. is a Very well-maintained 3-unit multi-family home, offering 1-bedroom units, ample natural light from skylights, and off street parking. Unit 3 comes fully furnished. All units have access to an owner supplied washer/dryer room in the thoughtfully designed basement containing designated storage areas for each unit. The property has a great rental history and generates good income,

William Paquin Maple Leaf Realty

400 South St, Bennington, VT 05201
/7
$14,500
- Land
- 1.20 Acres
- $12,083 per Acre
Lot 275 Oberdorf Rd, Stamford, VT 05350

Looking for the perfect Vermont escape? This 1.2-acre wooded lot in Alpenwald Village, Stamford, is your ticket to fun and freedom! Nestled in the beautiful Green Mountains, the land is mostly level with a charming creek along the edge--ideal for your dream home or weekend getaway. Just minutes to ski resorts, VAST trails for snowmobiling and ATV adventures, and nearby lakes for boating and

Christine Girard STEEPLEVIEW REALTY - N. ADAMS

Lot 275 Oberdorf Rd, Stamford, VT 05350
/45
$365,000
- 4 Beds
- 1 Bath
- 1,680 Sq Ft
19 Royal St, North Bennington, VT 05257

Charming North Bennington Home in a Desirable Neighborhood.Welcome to this beautifully updated four-bedroom home, ideally located in a sought-after North Bennington neighborhood. Situated on over half an acre, this property offers the perfect balance of privacy and convenience—just steps from scenic hiking trails and close to Bennington College.Step inside to discover a freshly

Lindsey Martin Maple Leaf Realty

19 Royal St, North Bennington, VT 05257
/40
$225,000
- 3 Beds
- 1 Bath
- 1,538 Sq Ft
721 Vt Route 7a, Shaftsbury, VT 05262

Located in the downtown neighborhood of Shaftsbury. Walking distance to school, town offices, country stores, parks and playgrounds. A first-floor bedroom with French doors leading outside - as well as a first-floor family room, laundry room, new kitchen and den. Two bedrooms upstairs. There's plenty of room in this home. A one car garage and fully fenced in lot for your privacy.

Wendy Larson Maple Leaf Realty

721 Vt Route 7a, Shaftsbury, VT 05262
/26
$275,000
- 3 Beds
- 2 Baths
- 1,440 Sq Ft
2899 W Sandgate Rd, Arlington, VT 05250

Nestled in the green mountains, come enjoy this three-bedroom, two-bath colonial on half an acre. Take in the beautiful meadow and mountain views from the spacious deck. Listen to the sounds of birds and the babbling brook in this lovely private location. The sunny level lot offers plenty of garden space and a generous shed for all your gardening needs. The first floor offers a spacious open

Margretta Fischer Wohler Realty Group

2899 W Sandgate Rd, Arlington, VT 05250
/10
$342,000
- Land
- 28 Acres
- $12,000 per Acre
11 Old County Rd E, Londonderry, VT 05148

A rare opportunity to own a wooded hillside property with potential southern and western views on a quiet country road in the much coveted village of Landgrove. Priced below the town assessment, the land is in current use, affording a tax savings, with a state permit for a 4-bedroom house. Enjoy all the elements of a Vermont country setting including a mix of mature hardwoods and softwoods,

Steve Stettler Four Seasons Sotheby's Int'l Realty

11 Old County Rd E, Londonderry, VT 05148
/54
$1,995,000
- 3 Beds
- 2.5 Baths
- 3,451 Sq Ft
139 Prospect St, Manchester, VT 05254

Originally built with classic charm, the home has undergone a top-to-bottom renovation that honors its history while delivering the modern updates today's homeowner craves. From raising the roof to enhance the second floor (literally), to installing new windows that flood the space with natural light and mountain views, no detail was overlooked. The entire second level was rebuilt, from the

Katherine Zilkha Four Seasons Sotheby's Int'l Realty

139 Prospect St, Manchester, VT 05254
/38
$1,995,000
- 5 Beds
- 3 Baths
- 6,323 Sq Ft
2589 W Sandgate Rd, Arlington, VT 05250

Two Pigs Farm is a hillside retreat in Southern Vermont's Taconic Range, where meadows are bound by ancient maple trees, stone walls and two clear brooks. The circa 1989 farmhouse and barns feel timeless—rooted, quietly graceful—designed for comfort, and connection. Inspired by childhood summers in Sandgate, the owner dreamed of a place where time stretches—mornings for berry picking, afternoons

Dia Jenks LandVest, Inc/Woodstock

2589 W Sandgate Rd, Arlington, VT 05250
/6
$14,500
- Land
- 1.00 Acre
- $14,500 per Acre
lot 305 Lebenschauung Cir, Stamford, VT 05352

Top-of-the-World Views Await - One Acre in Southern VermontDiscover your own slice of paradise with this beautiful one-acre wooded lot nestled in Southern Vermont. The current owner hand-picked this lot for its ''top of the world'' feel--and with a little clearing, the panoramic views will be nothing short of breathtaking.This is your chance to escape the hustle and build your dream retreat.

Christine Girard STEEPLEVIEW REALTY - N. ADAMS

lot 305 Lebenschauung Cir, Stamford, VT 05352
/38
$980,000
- 4 Beds
- 3.5 Baths
- 4,104 Sq Ft
25 Benson Fuller Dr, Jamaica, VT 05343

Mountain paradise awaits in this magnificent 5,000 sq ft Winhall retreat! Perched on a private acre with breathtaking, panoramic mountain views, this 4-bedroom, 3.5-bath home is an entertainer's dream and a serene escape.Step inside to discover a grand living room, a cozy family room, and a luxurious primary ensuite bedroom, each featuring a crackling wood-burning fireplace, perfect for

Robin Apps Four Seasons Sotheby's Int'l Realty

25 Benson Fuller Dr, Jamaica, VT 05343

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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.