Bennington County VT Houses for Sale

/37
$1,100,000
- 5 Beds
- 4.5 Baths
- 3,697 Sq Ft
1589 Richville Rd, Manchester Center, VT 05255

Welcome to your dream Vermont retreat. This classic 3 bedroom Colonial is gracefully set on 9.52 acres of open meadows with direct frontage on the Battenkill River, renowned worldwide for its exceptional trout fishing. With timeless architecture, peaceful privacy, and sweeping Mountain views, this property captures the essence of New England living. Inside, the home blends historic charm with

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

1589 Richville Rd, Manchester Center, VT 05255
/50
$425,000
- 3 Beds
- 2 Baths
- 1,941 Sq Ft
97 Buck Hill Rd, Shaftsbury, VT 05262

Two homes on 4.67 acres in Shaftsbury, VT! This village home offers a rare opportunity indeed by including a separate 2 bedroom ranch home as well. The main home is a charming New England farmhouse with 3 bedrooms and 2 bathrooms, living room, formal dining room, kitchen, main level laundry and so much more. The accessory dwelling unit offers 2 bedrooms, 1 bathroom, eat-in kitchen and living

Brenda Jones KW Vermont - Brenda Jones Real Estate Group

97 Buck Hill Rd, Shaftsbury, VT 05262
/57
$2,429,000
- 7 Beds
- 6.5 Baths
- 6,358 Sq Ft
349 Kent Hill Rd, Dorset, VT 05251

Located in the heart of Dorset Village, just a short walk to the town green, this stunning 7-bedroom, 7-bath residence, built in 1928, is a rare find. Set on 4 hill top acres, the property exudes timeless elegance, blending the charm of its historic roots with thoughtful modern updates. Inside, you will discover a captivating blend of warmth and sophistication. The gourmet kitchen, the heart of

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

349 Kent Hill Rd, Dorset, VT 05251
/59
$569,000
- 4 Beds
- 2 Baths
- 1,828 Sq Ft
69 Hillvale Dr, Manchester Center, VT 05255

This is a wonderful craftsman style ranch in a great location right in the heart of Manchester, in the sunny Hillvale neighborhood. It offers views to Mt. Equinox and is walking access to all Manchester's amenities. Four bedrooms, two full baths, updated kitchen with stainless appliances and granite counter tops, the dining room's french door opens on to an expansive deck for BBQ's and

Robert Sabol Wohler Realty Group

69 Hillvale Dr, Manchester Center, VT 05255
/26
$289,900
- 3 Beds
- 1.5 Baths
- 1,576 Sq Ft
519 South St, Bennington, VT 05201

Welcome to this beautifully maintained 3-bedroom, 1.25-bath home nestled on a corner lot in Bennington. This inviting property blends classic charm with thoughtful updates, offering comfort and style both inside and out.Step into the spacious kitchen featuring stunning wood cabinetry, granite countertops, and a functional island with a bar sink-perfect for entertaining or everyday living. The

Kelley Mccarthy Mahar McCarthy Real Estate

519 South St, Bennington, VT 05201
/27
$1,250,000
- 2 Beds
- 1 Bath
- 1,056 Sq Ft
233 Squires Rd, Manchester Center, VT 05255

Discover a rare opportunity to live and work amidst the serene beauty of Manchester, Vermont. This fully renovated 2-bedroom, 1-bath contemporary ranch, with leased solar array, is nestled on nearly 19 acres, offering a harmonious blend of modern comfort and entrepreneurial potential.The open-concept design features a spacious kitchen and living area, complemented by energy-efficient

Mark Triller Real Broker LLC

233 Squires Rd, Manchester Center, VT 05255
/49
$325,000
- 3 Beds
- 1.5 Baths
- 1,664 Sq Ft
93 Pace Rd, Bennington, VT 05201

Welcome Home to Your Private Woodland Retreat! ??Tucked away on a serene 2.75-acre wooded lot, this charming 3-bedroom, 1.5-bath home offers a rare blend of comfort, updates, and outdoor magic. With approximately 1,664 sq ft of living space, you’ll have plenty of room to stretch out—and three spacious decks to soak in those treetop views from every angle!? What’s New? Just about

Harvey Roettinger RE/MAX North Professionals

93 Pace Rd, Bennington, VT 05201
/34
$525,000
- 3 Beds
- 3 Baths
- 1,696 Sq Ft
104 Johnny Cake Hill Ln, Readsboro, VT 05350

If you've been dreaming of peaceful country living with stunning views, this one-of-a-kind home on approximately 22 private acres in the hills of Southern Vermont is calling your name. Greet each morning with an awe-inspiring easterly panorama that, on clear days, stretches all the way to Mount Monadnock.This serene retreat offers the best of nature — birdsong in the morning, occasional

Monica Sumner BHG Masiello Brattleboro

104 Johnny Cake Hill Ln, Readsboro, VT 05350
/31
$1,593,000
- 5 Beds
- 5 Baths
- 5,000 Sq Ft
951 Rupert Rd, Arlington, VT 05250

Discover peace and privacy on this scenic Sandgate, Vermont retreat near the New York border. Nestled on 67 acres of unspoiled land, it’s ideal for outdoor enthusiasts, or those seeking to get away from it all—blending natural beauty with comfortable living.Tucked down a long private drive, the home evokes a Scottish countryside manor. The spacious layout features a first-floor primary suite

Kristin Pirie KW Vermont Woodstock

951 Rupert Rd, Arlington, VT 05250
/39
$2,950,000
- 8 Beds
- 8.5 Baths
- 6,471 Sq Ft
69 Upper Taylor Hill Rd Unit D, Winhall, VT 05155

This extraordinary Stratton Mountain Retreat, just minutes to the slopes, offers glorious long range views and a very private setting. This impressive home was masterfully constructed in 2009 and includes a separate barn, 11.55 acres of land, 2 covered porches, a built in barbecue and an outdoor fireplace, hot tub and fire pit.The main level of the home features a Gourmet Kitchen, grand

Sara Buckley Josiah Allen Real Estate, Inc.

69 Upper Taylor Hill Rd Unit D, Winhall, VT 05155
/33
$349,900
- 3 Beds
- 1.5 Baths
- 1,666 Sq Ft
379 Swallow Hill Rd, Pownal, VT 05261

Welcome home! Tucked away on over 2.6 private and partially wooded acres in the exclusive and tight-knit Swallow Hill neighborhood, this stunning 3-bedroom, 1.5-bath home offers modern comfort and rustic charm in a serene natural setting in Southern Vermont.Step inside to soaring cathedral ceilings, exposed wood beams, and an abundance of Vermont beauty pouring in through large windows.

Cassie Barbeau Mahar McCarthy Real Estate

379 Swallow Hill Rd, Pownal, VT 05261
/7
$399,000
- 4 Beds
- 2 Baths
- 1,368 Sq Ft
72 Mckee Rd, Arlington, VT 05250

This charming 1985 Cape Cod style home, situated on 2.4 acres, is now available.The first floor features a kitchen with a cathedral ceiling, a comfortable living room, and two bedrooms. Upstairs, you will find an additional two bedrooms and a bathroom. The home also includes a full unfinished basement, offering potential for future expansion or storage. The barn could be used as a

Tatsiana Clark Four Seasons Sotheby's Int'l Realty

72 Mckee Rd, Arlington, VT 05250
/37
$1,700,000
- 6 Beds
- 7 Baths
- 5,400 Sq Ft
2001 Depot St, Manchester Center, VT 05255

Experience the best of Vermont living at Greybourne House, a fully furnished and impeccably maintained estate offering four-season enjoyment. With 6 bedrooms, 7 full bathrooms, and over 5,400 square feet of living space on 3.2 private acres, this home combines comfort, elegance, and an unbeatable location just minutes from Bromley, Stratton, and the dining and shopping of Manchester. A grand

Steven Bryant TPW Real Estate

2001 Depot St, Manchester Center, VT 05255
/50
$398,900
- 5 Beds
- 4 Baths
- 3,400 Sq Ft
927 Water St, North Bennington, VT 05257

Stately North Bennington Colonial with In-Law Suite & Barn on 2.6 Acres.Step into timeless elegance in this beautifully crafted colonial-style home located in the heart of charming North Bennington. Offering 5 spacious bedrooms and 4 bathrooms, this home features a flexible floor plan that includes a private in-law suite, formal living and dining rooms, a welcoming foyer, and both front and

Brenda Jones KW Vermont - Brenda Jones Real Estate Group

927 Water St, North Bennington, VT 05257
/57
$200,000
- 3 Beds
- 1 Bath
- 1,416 Sq Ft
100 Webb St, Bennington, VT 05201

Enchanted Historic Home with Storybook Charm – A Hidden Gem Near Downtown!Step into a fairytale in this one-of-a-kind, lovingly maintained home — a true magical retreat nestled just minutes from downtown. Owned and cherished by the same family since 1951, this architectural treasure blends old-world artistry with everyday comfort.From the moment you arrive, you're greeted by the

Lindsey Martin Maple Leaf Realty

100 Webb St, Bennington, VT 05201
/42
$1,950,000
- 9 Beds
- 7 Baths
- 6,956 Sq Ft
1086 West Rd, Bennington, VT 05201

Captivating French Provincial architecture is the hallmark of this 6,800 sq. ft 1866 Manor House occupying a commanding and picturesque view over 94 acres of pristine pastoral fields and the distant Taconic Mountain Range. The timeless and beautifully proportioned interiors feature extensive molding, solid oak flooring, eight fireplaces, nine bedrooms, seven baths, country kitchen and adjoining

Chris DeFelice Four Seasons Sotheby's Int'l Realty

1086 West Rd, Bennington, VT 05201
/49
$4,875,000
- 7 Beds
- 10 Baths
- 7,422 Sq Ft
318 Spring Hill Ln, Dorset, VT 05251

Welcome to a truly exceptional estate where classic charm and modern craftsmanship unite on 9 secluded acres in the heart of coveted Dorset, Vermont. Meticulously curated with no detail overlooked and no expense spared, this remarkable property features a beautifully renovated 1941 Colonial residence, complemented by a collection of newer luxury companion buildings that together create a one of a

Richard Slocum Four Seasons Sotheby's Int'l Realty

318 Spring Hill Ln, Dorset, VT 05251
/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
/43
$1,495,000
- 5 Beds
- 4.5 Baths
- 4,219 Sq Ft
7 Timberbrook N, Dorset, VT 05251

Modern Elegance Surrounded by Mountain Serenity. Stunning 5-bedroom, 4.5-bath home nestled on nearly 2 acres, just minutes from Dorset Green and Manchester Village. Blending modern design with traditional warmth, the property features energy-efficient geothermal heating & cooling and solar power. Expansive windows and French doors frame mountain views, the deck is perfect for entertaining. The

Margretta Fischer Wohler Realty Group

7 Timberbrook N, Dorset, VT 05251
/41
$1,449,000
- 4 Beds
- 4 Baths
- 2,736 Sq Ft
693 Longview Dr, Manchester, VT 05255

Tucked away in one of Manchester's most scenic neighborhoods, this 4-bedroom, 4-bathroom home offers peace,privacy,and thoughtful updates on three beautifully landscaped acres.Mature trees, immaculately crafted stone walls, a flowing brook,and expansive level lawn spaces create a true Vermont retreat.Centrally located near the town center and 1.5 miles from Burr and Burton Academy,you get the

Tara van de Velde Four Seasons Sotheby's Int'l Realty

693 Longview Dr, Manchester, VT 05255
/35
$244,900
- 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
/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
/21
$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
/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
/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
$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 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
$275,000
- 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
/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
/43
$1,975,000
- 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
/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
/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
$399,000
- 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
/48
$2,999,000
- 6 Beds
- 6.5 Baths
- 6,500 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

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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.