Bennington County VT Homes for Sale with Garage

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  /45

  $350,000

  • 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
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  /4

  $249,000

  • 5 Beds
  • 3 Baths
  • 2,184 Sq Ft

  137 Park St, Bennington, VT 05201

  Terrific income producing property. 2 - 1 bedroom units and a 3 bedroom unit with a garage. Close to town and modern systems. Good rental history. Is in a flood zone but owner has found a good flood insurance company.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  137 Park St, Bennington, VT 05201
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  /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
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  /23

  $4,000,000

  • 5 Beds
  • 2 Baths
  • 3,347 Sq Ft

  15 Wind Hill Rd, Manchester Center, VT 05255

  At the heart of this remarkable 136-acre property in Manchester Center, Vermont, are two distinct historic homes, each telling a story of the land’s deep roots in the Beattie-Forrest family, who have stewarded it for over a century.The original farmhouse, built circa 1800, offers five bedrooms and two baths, with timeless details including a vintage kitchen and hand-hewn timber framing.

  Paul Carroccio TPW Real Estate

  15 Wind Hill Rd, Manchester Center, VT 05255
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  /34

  $500,000

  • 1 Bed
  • 2 Baths
  • 300 Sq Ft

  417 Maple Hill Rd, Arlington, VT 05250

  Scandinavian Timber Frame Tiny House & Grindbygg! Over 10 acres of privacy and beautiful vistas. 360 degree mountain view from this custom heartfelt build. The property includes a one bedroom tiny house complete with kitchen, gas range, wood stove, movie projector, sleeping loft and so much more. A drilled well, on demand propane hot water heater and water shed for water storage. This cozy

  Margretta Fischer Wohler Realty Group

  417 Maple Hill Rd, Arlington, VT 05250
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  /31

  $150,000

  • 3 Beds
  • 1 Bath
  • 1,508 Sq Ft

  109 Evergreen Dr, Bennington, VT 05201

  House flippers and rehabbers rejoice: an excellent opportunity to put some sweat equity into this charming WWII-era gem at an accessible price. Last house on the right on a quiet dead-end road in a residential area of Bennington, this property boasts a lovely stream running along the northwest of the parcel, a cozy wood stove within, three bedrooms with more space adjoining, enclosed front

  Zachary Zupan EXP Realty

  109 Evergreen Dr, Bennington, VT 05201
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  /41

  $499,900

  • 4 Beds
  • 2.5 Baths
  • 2,116 Sq Ft

  245 Southshire Dr, Bennington, VT 05201

  Nestled in one of Bennington's most sought-after neighborhoods, this elegant 4-bedroom, 2.5-bath center-hall Colonial offers space, privacy, and timeless charm--all just minutes from downtown Bennington, SVMC Hospital, walking paths, and the Bennington Area Trail System(BATS). The first floor welcomes you with gleaming hardwood floors, a spacious kitchen, a formal dining room, and a gracious

  Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

  245 Southshire Dr, Bennington, VT 05201
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  /37

  $639,000

  • 3 Beds
  • 2 Baths
  • 2,070 Sq Ft

  68 Owls Nest Cir Unit B-7, Manchester, VT 05254

  Equinox on the Battenkill, is one of Southern Vermont’s premier condominium resort communities. Located in the historic Village of Manchester, nestled at the base of Mt. Equinox and situated along the acclaimed Equinox Golf Course and Battenkill River. One of it's gems, 68 Owls Nest Circle, has opened up and is priced to sell! Fresh interior and exterior paint and new windows. This charming 3

  Dana Kingsley Josiah Allen Real Estate, Manchester Branch Office

  68 Owls Nest Cir Unit B-7, Manchester, VT 05254
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  /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
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  /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
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  /45

  $1,350,000

  • 6 Beds
  • 7 Baths
  • 5,400 Sq Ft

  2001 Depot St, Manchester Center, VT 05255

  LOCATION, LOCATION: 8 minutes from Bromley, 20 minutes to Stratton, yet close to Manchester restaurants, shopping, fishing, Horse Show & golf. Built as a bed & breakfast, this fully furnished and impeccably maintained 6-bedroom, 7-bathroom retreat offers 5,400+ square feet of living space on 3.2 private acres—perfect for use as a primary residence, vacation getaway, or a return to its B&B roots.

  Steven Bryant TPW Real Estate

  2001 Depot St, Manchester Center, VT 05255
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  /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
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  /50

  $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
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  /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
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  /37

  $1,275,000

  • 4 Beds
  • 4 Baths
  • 4,266 Sq Ft

  693 Longview Dr, Manchester, VT 05255

  This four-bedroom, four-bath home offers not only exceptional views and privacy but also the convenience of an in-town location. It's ideally situated in Manchester Village, set on three landscaped acres featuring mature trees, custom stonework, level lawns, and active brook.The interior of the home provides a comfortable living space. On the Main Level, you'll find a spacious living room

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  693 Longview Dr, Manchester, VT 05255
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  /33

  $1,274,999

  • 4 Beds
  • 2.5 Baths
  • 4,620 Sq Ft

  139 Village View Rd, Manchester, VT 05255

  From morning coffee on the deck to cozy evenings by the fire, this Manchester home is designed for comfort, flexibility, and four-season living. The main level features a bright great room, an eat-in kitchen with an adjacent covered porch, a formal dining room, a den with a fireplace, two bedrooms, a full bath, and a primary suite with a walk-in shower and a jetted tub.The finished lower

  Marek Kovac TPW Real Estate

  139 Village View Rd, Manchester, VT 05255
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  /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
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  /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
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  /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
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  /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
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  /49

  $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

  1677 Barnumville Rd, Manchester Center, VT 05255
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  /57

  $617,000

  • 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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  /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
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  /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
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  /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
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  /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
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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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  /46

  $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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  /27

  $549,000

  • 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
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  /40

  $1,249,000

  • 4 Beds
  • 6 Baths
  • 5,764 Sq Ft

  842 Dorset Rd W, Dorset, VT 05251

  Spacious luxury contemporary on 15 amazing acres conveniently located on the Dorset West Road. 4 bedrooms including a primary suite on the main floor with adjoining office and huge walk-in closet. Second primary with bath on second floor. Living room with massive stone fireplace and bar area. Well planned and equipped kitchen. Comfortable dining room between living room and kitchen.

  Jill Simon Josiah Allen Real Estate, Manchester Branch Office

  842 Dorset Rd W, Dorset, VT 05251
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  /25

  $199,000

  • 4 Beds
  • 4 Baths
  • 3,576 Sq Ft

  883 Vt Route 7a, Shaftsbury, VT 05262

  A classic Victorian home in the village of Shaftsbury is waiting for your imagination and perseverance to bring this once charming residence back to its original luster. Each room has its own character from dining room built-ins, shelving throughout the entire house to display your precious treasures, living room fireplace for those cozy winter nights, exposed brick and extra large eat-in

  Monique Geannelis Mahar McCarthy Real Estate

  883 Vt Route 7a, Shaftsbury, VT 05262
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  /50

  $4,999,000

  • 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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  /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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  /57

  $2,495,000

  • 5 Beds
  • 4.5 Baths
  • 4,483 Sq Ft

  743 Green Peak Orchard, Manchester Center, VT 05255

  Exceptional Main Residence and Guest House in a premier quintessential Vermont setting, beautifully designed to capture spectacular views of mountains and sunsets. Situated on 7.9 acres in an exceptional estate-style setting, the forward-thinking floor plan is prime for entertaining in multiple spaces, while still maintaining a welcoming New England character.With views from every gathering

  Kim Morgan-Wohler Wohler Realty Group

  743 Green Peak Orchard, Manchester Center, VT 05255
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  /47

  $625,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft

  682 Fox Hill Rd, Bennington, VT 05201

  Soak up the mountain view from a brand new custom built home. Desirable neighborhood with paved town maintained roads. Just outside of Old Bennington and close to SVMC hospital, downtown restaurants and theaters. An easy commute to Bennington College, 22 minute drive to Williamstown, MA or an hour to Albany Int'l Airport. Nestled at the base of Mount Anthony, hikers will appreciate direct

  Jenifer Prouty Hoffman Hoffman Real Estate

  682 Fox Hill Rd, Bennington, VT 05201
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  /34

  $1,695,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,688 Sq Ft

  143 Stratton Mountain Access Rd, Winhall, VT 05340

  Welcome to 143 Stratton Mountain Access Road, a newly completed 5-bedroom, 5 bath residence by DG Builders, located just minutes from Stratton Mountain Resort and all the year round activities it has to offer. Blending modern mountain style with timeless Vermont charm, this home is move-in ready and waiting for its first owners.The light filled open floor plan showcases wide-plank oak floors,

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  143 Stratton Mountain Access Rd, Winhall, VT 05340
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  /55

  $10,300,000 New Construction

  • 6 Beds
  • 9 Baths
  • 10,993 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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  /9

  $1,350,000 New Construction

  • 3 Beds
  • 4.5 Baths
  • 3,415 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

  3746 Main St, Manchester, VT 05255
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  /9

  $575,000 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

  18 Jameson Flats Rd Unit 18, Manchester, VT 05255
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  /50

  $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

  38 Jamesons Flats, Manchester, VT 05255

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