Bennington County VT Homes for Sale with Garage

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  $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
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  $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
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  $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
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  $279,900

  • 4 Beds
  • 2 Baths
  • 1,302 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
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  $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
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  $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
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  /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
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  $1,475,000

  • 4 Beds
  • 2.5 Baths
  • 4,084 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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  $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
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  /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
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  $2,500,000

  • 5 Beds
  • 7 Baths
  • 6,625 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
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  $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
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  $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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  $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
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  /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
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  $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
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  $1,350,000

  • 4 Beds
  • 4 Baths
  • 4,640 Sq Ft

  33 Forest Haunts Rd, Winhall, VT 05340

  Discover Your Vermont Retreat Nestled amidst 20.8 private acres of tranquil woods, this French country manor offers an exceptional opportunity to own a piece of Vermont paradise. Situated near the serene North Branch Ball Mountain Brook, enjoy the soothing sounds of cascading water and the breathtaking beauty of nature. Property Highlights: Prime Location: Just minutes from Stratton Resort for

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  33 Forest Haunts Rd, Winhall, VT 05340
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  $549,000

  • 4 Beds
  • 2.5 Baths
  • 2,700 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
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  $5,999,000

  • 6 Beds
  • 7.5 Baths
  • 8,720 Sq Ft

  454 Mountain Rd, Stratton, VT 05155

  Welcome to a one-of-a-kind 141-acre mountaintop retreat at Stratton Mountain Resort - an extraordinary sanctuary with panoramic views of Stratton, Mount Snow, and Bromley. Designed for elegance and ease, this home is a rare blend of architectural beauty, comfort, and sophistication.A gracious entryway opens to a sunlit living room and library anchored by an 18-foot stone fireplace.

  Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  454 Mountain Rd, Stratton, VT 05155
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  $3,275,000

  • 6 Beds
  • 3.5 Baths
  • 3,250 Sq Ft

  73 Pine Rd, Dorset, VT 05251

  This custom-designed modern farmhouse in Dorset, Vermont was completed in 2023. Soaked in natural light, this sunny home may be everything you are looking for. Spectacular mountain and valley views from this private location, yet minutes from all the best of Southern Vermont. Every detail is completely planned and executed - from the Marvin Ultimate windows to the Waterworks bathtub, the finishes

  Christiane Carroccio TPW Real Estate

  73 Pine Rd, Dorset, VT 05251
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  /40

  $1,975,000

  • 4 Beds
  • 4 Baths
  • 4,270 Sq Ft

  14 Old Ridge Rd, Winhall, VT 05155

  This mountain home is beautifully furnished with a refined design that perfectly balances comfort and style, offering a seamless move-in ready experience. Located in the sought-after High Meadow neighborhood, this four bedroom, four bathroom property sits high on a perch, with clear views of Stratton’s trails, and a view of Bromley from the front of the house. Rebuilt in 2023/2024, the home is

  Christiane Carroccio TPW Real Estate

  14 Old Ridge Rd, Winhall, VT 05155
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  $2,495,000

  • 5 Beds
  • 4.5 Baths
  • 3,583 Sq Ft

  743 Green Peak Orchard, Manchester Center, VT 05255

  Beautifully designed to capture spectacular views of mountains and sunsets, this exceptional residence has recently completed the addition of another full bath, improving the floor plan, situated on 7.9 open acres w/guest house/barn off Overlook Drive in Green Peak Orchard. With views from every gathering space; living room, billiard room and gourmet kitchen, the residence is situated to

  Kim Morgan-Wohler Wohler Realty Group

  743 Green Peak Orchard, Manchester Center, VT 05255
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  $10,300,000 New Construction

  • 6 Beds
  • 9 Baths
  • 10,609 Sq Ft

  551 West Fields, Manchester, VT 05254

  Discover "the pinnacle of luxury living" in the heart of Manchester Village! Crafted by Breen Builders and Ramsay Gourd Architect, every detail reflects superior craftsmanship and timeless elegance! From the very foundation to the finishing touches, attention to detail and commitment to quality shine through! Experience the perfect blend of luxury and convenience in this stunning 10,000 sq.ft

  Sunny Breen Josiah Allen Real Estate, Inc.

  551 West Fields, Manchester, VT 05254
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  $1,350,000 New Construction

  • 3 Beds
  • 4.5 Baths
  • 2,200 Sq Ft

  3746 Main St, Manchester, VT 05255

  Monarch on Main – Luxury Living in Historic Manchester VillageAnticipated completion, Fall 2025, Monarch on Main offers the rare opportunity to own a thoughtfully designed townhome in the heart of Manchester Village. Imagine an easy strolling to fine dinning, shopping and evening events. This three-level residence combines the efficiency of new construction with the timeless charm of its

  Britt Wohler Wohler Realty Group

  3746 Main St, Manchester, VT 05255
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  /9

  $599,000 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
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  $849,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,980 Sq Ft

  40 Jameson Flats Unit D, Manchester, VT 05255

  New Construction in the Heart of Manchester – Showings Begin April 15This beautifully designed 3-bedroom, 2.5-bath freestanding home (with potential for a 4th bedroom) offers modern comfort, energy efficiency, and fine craftsmanship just steps from downtown Manchester. The open-concept main level features a chef’s kitchen with an eat-in island, ample storage, stainless steel appliances,

  Britt Wohler Wohler Realty Group

  40 Jameson Flats Unit D, Manchester, VT 05255
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  $795,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,760 Sq Ft

  38 Jamesons Flats, Manchester, VT 05255

  NEW CONSTRUCTION -Showings Begin 3/1.This beautifully designed 3-bedroom, 2.5-bath Condo blends modern comfort & energy-conscious features in a prime location, just steps from the heart of Manchester. An open-concept main living area is perfect for entertaining, with a kitchen featuring an eat-in island, ample storage, stainless steel appliances, including your choice of electric or propane

  Britt Wohler Wohler Realty Group

  38 Jamesons Flats, Manchester, VT 05255

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