Bennington County VT Homes for Sale

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  /29

  $250,000

  • 9 Beds
  • 5 Baths
  • 3,810 Sq Ft

  6982 Main St, Readsboro, VT 05350

  Prime location meets potential! Situated in the center of charming Readsboro, this 5-unit multi-family property offers a rare opportunity for investors and owner-occupants alike. Whether you're looking to expand your portfolio or live in one unit while generating rental income from the others, this property delivers. Some renovations needed – perfect for those looking to add value and

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  6982 Main St, Readsboro, VT 05350
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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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  /52

  $269,000

  • 2 Beds
  • 1 Bath
  • 1,400 Sq Ft

  3264 Route 153, West Rupert, VT 05776

  This neat and tidy single story home has been completely renovated from top to bottom, offering comfort, efficiency, and style. Updates include all new metal roof, vinyl siding, thermopane windows, propane hot-air heating system with heat pump central air conditioning, appliances, kitchen cabinets, counters, and hardwood flooring. Also updated plumbing, fiber optic internet, new electrical with a

  Scott McChesney McChesney RE, Inc.

  3264 Route 153, West Rupert, VT 05776
• 

  

  

  /22

  $895,000

  • Land
  • 24.08 Acres
  • $37,168 per Acre

  A Windsor Rd, Manchester, VT 05255

  Simply Extraordinary! 24.08 Acres with a State Wastewater Permit for 11 Bedrooms that includes 2 buildable lots within the acreage. With unrivaled easterly views, this parcel is the last permitted within what is now the Forest and Recreational/Farming and Rural Residential District of Manchester , Vermont. There will be no further development around this parcel. Abutted by protected lands and

  Kim Morgan-Wohler Wohler Realty Group

  A Windsor Rd, Manchester, VT 05255
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  /3

  $219,000

  • 2 Beds
  • 1 Bath
  • 1,872 Sq Ft

  17 Henry Hill, Stamford, VT 05352

  Sean Taylor Moresi Real Estate Partners

  17 Henry Hill, Stamford, VT 05352
• 

  

  /41

  $950,000

  • 4 Beds
  • 3.5 Baths
  • 3,031 Sq Ft

  7 Roundtree Rd, Winhall, VT 05340

  Discover the perfect mountain retreat at 7 Roundtree Road, a contemporary and beautifully designed 4-bedroom home set on 1.37 private acres in one of Stratton’s most sought-after neighborhoods. Ideally located just a quick drive to the Base Lodge—or simply hop on the convenient shuttle for effortless access to the slopes—this property offers the best of Stratton living in every season.Step

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  7 Roundtree Rd, Winhall, VT 05340
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  /4

  $28,000

  • Land
  • 2.3 Acres
  • $12,174 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 2-acre lot offers the perfect blend of privacy and convenience. The property is partially cleared, making it easy to envision your dream home while still enjoying the natural beauty and tranquility of the surrounding forest. With power already available at the road and septic plans in place, much of the groundwork

  Flex Realty Group Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350
• 

  

  /15

  $298,500

  • Land
  • 3.7 Acres
  • $80,676 per Acre

  69 Benson Fuller Dr, Winhall, VT 05340

  High dry and spectacular views of the Equinox Mountain range and Bromley Mountain! Oversized building lot with lots of privacy. Approved septic system for a 5 bedroom house!

  Andrea Linkin-Butler Stratton Buyer Brokerage

  69 Benson Fuller Dr, Winhall, VT 05340
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  /24

  $471,000

  • 3 Beds
  • 2 Baths
  • 1,357 Sq Ft

  102 Mccormick Ln, Sunderland, VT 05250

  Built in 2003, the home's open-concept design is highlighted by a bright and airy living/dining/kitchen area, where large windows flood the space with abundant natural light. A cozy pellet stove provides warmth and ambiance for those crisp Vermont evenings. The functional layout features two comfortable bedrooms and a full bathroom on the main level, while the private primary ensuite bedroom

  Dana Kingsley Josiah Allen Real Estate, Manchester Branch Office

  102 Mccormick Ln, Sunderland, VT 05250
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  /34

  $249,900

  • 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
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  /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
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  /29

  $729,000

  • 3 Beds
  • 3.5 Baths
  • 2,262 Sq Ft

  253 Owls Head Hill Ln S, Dorset, VT 05251

  Welcome to this beautifully maintained Cape-style home tucked away on peaceful cul-de-sac with stunning mountain views. Enjoy your morning coffee on the front porch and relaxing evenings on the spacious back deck. Inside, you will find a warm and inviting layout featuring a gorgeous newer kitchen with modern finishes and ample space for cooking, gathering, and entertaining. The thoughtful floor

  Annette Gallo Real Broker LLC

  253 Owls Head Hill Ln S, Dorset, VT 05251
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  /39

  $599,000

  • 5 Beds
  • 3.5 Baths
  • 2,468 Sq Ft

  17 Signal Hill Rd, Winhall, VT 05340

  17 Signal Hill Road offers Vermont charm in a secluded mountain setting. With over 2,400 square feet of living space, this five-bedroom, three-and-a-half-bath home has been thoughtfully maintained and move-in ready. The main level features a spacious living room with a dramatic fieldstone fireplace, vaulted ceilings, and skylights that fill the home with natural light. A loft overlooking

  Christiane Carroccio TPW Real Estate

  17 Signal Hill Rd, Winhall, VT 05340
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  /30

  $550,000

  • 2 Beds
  • 2 Baths
  • 2,218 Sq Ft

  1439 Main St, Manchester Center, VT 05255

  Purdy School House, est. 1850 - Step into history with this lovingly preserved former schoolhouse, offering timeless character with modern comfort. Featuring 2 bedrooms, 2 baths, and a striking stone fireplace, this home blends warmth and charm. A full basement and attached one-car garage provide practical convenience. Set on 2.01 acres, the property includes a fenced dog yard and plenty of space

  Richard Slocum Four Seasons Sotheby's Int'l Realty

  1439 Main St, Manchester Center, VT 05255
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  /4

  $190,000

  • 5 Beds
  • 2 Baths
  • 1,478 Sq Ft

  32-34 Sage St, Bennington, VT 05257

  Duplex in North Bennington offering 1 way street location. decent yard and 2 - 2 bedroom units. Good investment potential in a walkable and sought location. Town water and sewer. Current tenants keep their units up well.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  32-34 Sage St, Bennington, VT 05257
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  /60

  $1,745,000

  • 17 Beds
  • 20 Baths
  • 14,861 Sq Ft

  3888 Vermont Route 7a, Shaftsbury, VT 05262

  The historic Arlington Inn & Spa is the centerpiece of scenic Arlington, Vermont. It features a tavern, restaurant and massage spa room. There are 15 guest rooms in 3 buildings, and an antique event barn on over 3.5 beautifully landscaped acres. This unique property can easily be configured in many creative ways. It could remain as an inn with a restaurant and bar. It could become a restaurant

  Vicki Wilson Maple Leaf Realty

  3888 Vermont Route 7a, Shaftsbury, VT 05262
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  /4

  $27,999

  • Land
  • 2.4 Acres
  • $11,666 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 2.4-acre lot offers the perfect blend of privacy and convenience. The property is partially cleared, making it easy to envision your dream home while still enjoying the natural beauty and tranquility of the surrounding forest. With power already available at the road and septic plans in place, much of the groundwork

  Flex Realty Group Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350
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  /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
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  /60

  $629,000

  • 5 Beds
  • 3.5 Baths
  • 3,271 Sq Ft

  5408 Main St, Manchester Center, VT 05255

  A great in town location offering two Homes,#5406 and #5408. The Front house is a three bedroom, two full bath home with a great front covered porch with views of Mt. Equinox. You can easily walk to all of Manchester Center's amenities. The back Cottage has two bedrooms, one and a half baths with kitchen and living area. This property is zoned as multi use which provides the owners the ability to

  Robert Sabol Wohler Realty Group

  5408 Main St, Manchester Center, VT 05255
• 

  

  /23

  $360,000

  • 3 Beds
  • 2 Baths
  • 1,590 Sq Ft

  22 Carlen St, Manchester Center, VT 05255

  Live in one and rent the other. Discover the charm and value of this affordable starter home with rental option. Located in a quiet, residential area of Manchester. This spacious ranch-style property offers a rare combination of flexibility, space, and opportunity, perfect for first-time buyers, investors, or anyone looking to create their dream home with a few finishing touches. The main level

  Andy Reed Four Seasons Sotheby's Int'l Realty

  22 Carlen St, Manchester Center, VT 05255
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  /33

  $295,000

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  254 Union St, Bennington, VT 05201

  Welcome to this well-maintained, solid income-producing two-family home located in the heart of town—just steps from shops, dining, and downtown events. Perfect for owner-occupants or savvy investors, this property combines classic charm with modern efficiency and low operating costs.Each two-bedroom unit features spacious, light-filled living areas, eat-in kitchen and comfortable

  Cassie Barbeau Mahar McCarthy Real Estate

  254 Union St, Bennington, VT 05201
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  /29

  $415,000

  • 6 Beds
  • 3 Baths
  • 5,208 Sq Ft

  126 Washington Ave, Bennington, VT 05201

  Circa 1913 carriage barn converted into a mixed-use property in the heart of downtown Bennington. This distinctive 5,208± sq. ft. building combines residential and commercial opportunity, featuring three apartments and a ground-floor retail space. Original architectural details evoke the property’s historic character, while modern updates support comfortable living and reliable income potential.

  Vicki Wilson Maple Leaf Realty

  126 Washington Ave, Bennington, VT 05201
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  /2

  $20,000

  • Land
  • 3 Acres
  • $6,667 per Acre

  0 U S 7, Pownal, VT 05261

  3 acre parcel located behind other parcels. Would be a great place for a hunting "camp", blind or recreation. Right of Way is from 63 Metcalfe Road, Pownal.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  0 U S 7, Pownal, VT 05261
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  /55

  $995,000

  • 5 Beds
  • 4.5 Baths
  • 2,321 Sq Ft

  24 N Branch Rd, Winhall, VT 05340

  Exceptional Renovation of a Stratton Resort Residence in the Stratton Quarter Mile neighborhood on Shuttle, just a short walk home from the Village. Beautiful upscale baths with tile work and craftsmanship of the highest caliber. Wood floors throughout. Open gourmet kitchen makes for premier apres ski gatherings. With 5 bedrooms/4 baths and multiple ensuite- this mountain chalet has been updated

  Kim Morgan-Wohler Wohler Realty Group

  24 N Branch Rd, Winhall, VT 05340
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  /22

  $225,000

  • 2 Beds
  • 1 Bath
  • 784 Sq Ft

  67 Bourn Brook Rd Unit 57, Manchester Center, VT 05255

  Discover your perfect blend of comfort and convenience in this charming two-bedroom, one-bathroom townhouse in Manchester Center. With thoughtfully designed living space, this home offers laminate wood flooring throughout the main level, creating a warm and welcoming atmosphere. Venture upstairs where you'll be greeted by stunning views of Equinox Mountain - a daily reminder of Vermont's natural

  Julie Citron RE/MAX Four Seasons

  67 Bourn Brook Rd Unit 57, Manchester Center, VT 05255
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  /6

  $110,000

  • Land
  • 1 Acre
  • $110,000 per Acre

  88A Sylvan Ridge Rd, Winhall, VT 05340

  Wooded lot with hardwoods, evergreens and birch trees. Potential views of Bromley Mountain and beyond. Town maintained road. Close to VAST snowmobile trails. Build your dream home in the Golden Triangle of ski areas, Stratton, Bromley, and Magic Mountains. Only 10 minuets to Manchester. Available on request:Wastewater System and Potable Water Supply PermitSeptic

  Andrew King Stratton Real Estate

  88A Sylvan Ridge Rd, Winhall, VT 05340
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  /56

  $2,300,000

  • 9 Beds
  • 8 Baths
  • 5,512 Sq Ft

  288 Cedar Ln, Peru, VT 05152

  Imagine your own private Vermont resort getaway just a short drive from Bromley Mountain! Nestled on 12 peaceful acres, this property offers the perfect blend of relaxation, recreation, and convenience. Spend summer days swimming or paddling on your private pond, relaxing on the sandy beach, soaking in the hot tub, or unwinding in the sauna after a workout in your home gym. Evenings can be

  Jessica Citera Cummings & Co

  288 Cedar Ln, Peru, VT 05152
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  /56

  $3,350,000

  • 3 Beds
  • 4.5 Baths
  • 3,059 Sq Ft

  466 3 Maple Dr, Manchester, VT 05254

  Welcome to Three Maple Drive, a beautifully crafted, brand-new single-family home nestled in a quiet and scenic location in Manchester, Vermont. Built in 2023 with impeccable attention to detail, this 3,059 sq ft modern farmhouse seamlessly blends luxury, comfort, and timeless design—all set on a private 3.85-acre lot with gorgeous mountain views.This home features three spacious bedroom

  David Shehadi Josiah Allen Real Estate, Inc.

  466 3 Maple Dr, Manchester, VT 05254
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  /33

  $575,000

  • Land
  • 99.31 Acres
  • $5,790 per Acre

  000 Vermont 11, Peru, VT 05152

  Embrace the timeless beauty of Vermont with this exceptional 99.31-acre retreat. Nestled in the heart of picturesque Peru, Vermont, this expansive land parcel offers an extraordinary opportunity to own a slice of New England’s breathtaking landscapes. Surrounded by lush forests and bordering pristine national forest land, this property boasts timeless views of neighboring fields and the Green

  Kim Prins Four Seasons Sotheby's Int'l Realty

  000 Vermont 11, Peru, VT 05152
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  /37

  $585,000

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

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

  Special Price!! EOB Unit B-7!!! Equinox on the Battenkill, one of Southern Vermont’s premier condo/resort communities located in the historic village of scenic Manchester. This charming 3 bed 2 bath luxury town home, one of the select few with attached garages, offers the privacy of a quiet cul de sac, beautifully landscaped. Four seasons living in sought out neighborhood, Owls Nest! Management

  Dana Kingsley Josiah Allen Real Estate, Manchester Branch Office

  68 Owls Nest Cir Unit B-7, Manchester, VT 05254
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  /47

  $245,000

  • 2 Beds
  • 2 Baths
  • 911 Sq Ft

  726 Rice Ln, Bennington, VT 05201

  Welcome to this charming Cape-style home, nestled in a peaceful country setting just moments from Bennington College and scenic walking and hiking trails. This inviting property offers the perfect blend of rural tranquility and convenient access to town. Located just 10 minutes from downtown Bennington, you’ll have quick access to local shops, restaurants, cultural attractions, and everyday

  Thomas Martins Maple Leaf Realty

  726 Rice Ln, Bennington, VT 05201
• 

  

  /42

  $575,000

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft

  211 Rod and Gun Club Rd, Shaftsbury, VT 05262

  Welcome to Rod and Gun Club Rd. Offering 1748 sq ft, with a full useable basement, sitting on 4.43 acres of land, with a 3-bay garage with carport as well as, an attached 2-car garage, a barn with stalls if you want to have some animals. This newly renovated ranch style home with thoughtful design offers 3B,2Bath, with a spacious and flexible layout with a fireplace with a gas insert in the

  Wendy Larson Hooscik Realty

  211 Rod and Gun Club Rd, Shaftsbury, VT 05262
• 

  

  /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
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  /17

  $85,000

  • Land
  • 9.74 Acres
  • $8,727 per Acre

  1 & 2 Joy Ln, Arlington, VT 05250

  Two Perked and Permitted Building Lots tucked away in the village of Arlington. Survey and Waste Water Permit available for two lots totaling 9.74 acres. These two Joy Lane lots are ready for your vision and your dreams. Close to town and all amenities, however private. Opportunity awaits to build one house or two. Owners are selling both lots together. The next owner could build on one lot and

  Margretta Fischer Wohler Realty Group

  1 & 2 Joy Ln, Arlington, VT 05250
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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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  /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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  /28

  $414,900

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  139 Bergwelt Ln, Readsboro, VT 05350

  Charming Country Retreat with Scenic Views and Timeless Character.Welcome to your dream country escape! Nestled on a peaceful, tree-lined lane, this beautifully maintained 3-bedroom, 2-bathroom home offers the perfect blend of rustic charm and modern comfort. Set on a spacious 3.6 acre lot, the property boasts serene views, mature gardens, and ample privacy — ideal for relaxing weekends or

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  139 Bergwelt Ln, Readsboro, VT 05350
• 

  

  /10

  $14,999

  • Land
  • 1 Acre
  • $14,999 per Acre

  0 Oberhugel Rd, Readsboro, VT 05350

  1-acre generally flat and densely wooded building lot in Alpenwald Village in Stamford, VT. This is a very well maintained district with lots of privacy and the neighbors widely spread out on their own acreage, yet there's still a friendly neighborhood feel. Speaking of privacy, the rear boundary is the large southern portion of the 420,000-acre Green Mountain National Forest. Stare off your back

  David White OwnerEntry.com

  0 Oberhugel Rd, Readsboro, VT 05350
• 

  

  /31

  $339,000

  • 3 Beds
  • 1.5 Baths
  • 1,829 Sq Ft

  89 Merson St, Woodford, VT 05201

  This inviting in-town home has been nearly completely renovated with only a few more touches to be brought by the new owner, blending fresh updates with classic comfort. Inside, you’ll find 3 bedrooms and a full bath, plus a bonus room that could serve as a 4th bedroom with a half-bath. An additional room with its own separate entrance is ideal for a small home business. The convenient attached

  Cassie Barbeau Mahar McCarthy Real Estate

  89 Merson St, Woodford, VT 05201
• 

  

  /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

Showing Results 121 - 160, Page 4 of 5