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Bennington County

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41-43 Cranberry Hill Road Winhall VT 05340

Winhall, VT41-43 Cranberry Hill Road

Price$979,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5079224

  • Residential Single Family
  • Full Bath 3
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 5,248

This is the ultimate modern Alpine chalet, fully renovated yet boasting the classic flat-sawn balusters characteristic of mountain homes in the Alps. Three expansive floors offer sunny, well-appointed space, beginning with a roomy mudroom, three bedrooms and two bathrooms (one en-suite). Head upstairs to join your friends and family in the open-concept European kitchen/living/dining room with expanded island optimal for entertaining -- grill and wraparound deck just outside the kitchen. The fourth bedroom -- a primary suite with en-suite bathroom -- is on this level. On the walk-out lower level, a game room with pool table and a separate TV room with gas stove offer a getaway before soaking in the hot tub, within earshot of the babbling brook down the hill. Nestled in the coveted community of Strattonwald, this 4-bedroom home offers Stratton shuttle access right from the driveway. Strattonwald's rare swimming pond, sandy beach, tennis/pickleball courts, picnic area, and space to fish and kayak make it one of the area's most preferred communities. Finally -- a renovated 1BR/1BA guest house boasts space for guests, in-laws, your office, or long-term rental income. Just in time to move in, enjoy summer, and get geared up for your first season in your Vermont ski house! Call for your tour soon.

Listed by Jamie Luke of TPW Real Estate

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

2001 Depot Street Manchester VT 05255

Manchester, VT2001 Depot Street

Price$950,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5042704

  • Residential Single Family
  • Full Bath 6
  • Address 2001 Depot Street
  • Bedrooms 6
  • Bathroom 7

LOCATION, LOCATION: Just 8 minutes to Bromley and 20 minutes to Stratton, yet close to Manchester's dining, shopping, fishing, golf, and the Horse Show. Built as a bed & breakfast, this fully furnished and impeccably maintained 6-bedroom, 7-bath retreat offers over 5,400 sq ft on 3.2 private acres-ideal as a primary home, vacation getaway, or rental investment. With a strong history as a successful Airbnb/short-term rental, Greybourne House is well-positioned for continued income. Freshly painted interiors create a bright, welcoming feel, and a brand-new outdoor hot tub adds a luxury touch. The home features two generous living areas-the main floor great room and the walkout lower-level den-designed for gathering and relaxation. The chef's kitchen with double ovens, dual refrigerators, granite counters, and a central island flows into the dining room for easy entertaining. Two bedrooms, including the primary suite, are on the main level, while four additional en-suite bedrooms upstairs each offer a gas fireplace and TV. The oversized two-car garage connects through a custom ski mudroom to a well-equipped laundry and pantry. The finished lower level adds a den, bar, game/lounge areas, a full bath, and direct access to the landscaped grounds. With flexible zoning, a prime location, and strong rental appeal, Greybourne House is a move-in-ready year-round retreat or income-producing property.

Listed by Steven Bryant of TPW Real Estate

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

24 North Branch Road Winhall VT 05340

Winhall, VT24 North Branch Road

Price$950,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5069406

  • Residential Single Family
  • Full Bath 4
  • Address 24 North Branch Road
  • Bedrooms 5
  • Bathroom 5

Location says it all ! Stratton Quarter Mile neighborhood on Shuttle, just a short walk home from the Village. This exceptional renovation offers an expanded floor plan with a third level.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 with all the comforts you expect in a luxury getaway. Two wood burning fireplaces , tasteful ambiance with warm wood ceiling and accents. A second family room is designed as a T.V. Room/den with kitchenette/bar for movie night snacks and football game halftime spreads.The floor plan offers bedrooms on each of three levels- ideal for inviting friends and multiple families.Equipped with a well designed mudroom entrance Shuttle picks you up at your driveway and an easy walk home for those who want to close down Grizzlies apres ski and bands.Roads and security fees apply. Stratton Sports Center Bond eligible and property is served by community water and sewer. What are you waiting for? This is beautifully redone and turn key. No need for a project. This mountain residence is ready to go and prime for the winter enthusiast! Stratton Mountain is calling you!

Listed by Kim Morgan-Wohler of Wohler Realty Group

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

7 Roundtree Road Winhall VT 05340

Winhall, VT7 Roundtree Road

Price$950,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5071605

  • Residential Single Family
  • Full Bath 2
  • Address 7 Roundtree Road
  • Bedrooms 4
  • Bathroom 4

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 inside to find a spacious, light-filled interior with clean contemporary lines, warm natural materials, and an inviting open layout ideal for gathering with family and friends. Large windows bring the outdoors in, while generous living spaces provide plenty of room to relax after a day on the mountain. With four well-appointed bedrooms, this home comfortably accommodates guests and offers flexible space for work, play, or quiet retreat. Outside, the expansive 1.37-acre lot delivers the privacy and peaceful surroundings you expect from a mountain home, including a covered deck with a hot tub and grill to be able to enjoy year round, all while keeping you close to the heart of the resort. Whether you're seeking a year-round getaway, a winter ski home, or a property with excellent rental potential, 7 Roundtree Road delivers contemporary style, convenience, and Stratton Mountain charm in one exceptional package.

Listed by Bob Maisey of Berkshire Hathaway HomeServices Stratton Home

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

171 Mending Walls Road Manchester VT 05255

Manchester, VT171 Mending Walls Road

Price$925,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5083086

  • Residential Single Family
  • Full Bath 1
  • Bedrooms 3
  • Bathroom 5
  • Square Feet 3,718

Looking for "NEW"? This residence is as close to new construction as it gets, having been thoughtfully gutted to the studs and tastefully renovated across all three levels. The stunning new quartz island kitchen features all new stainless appliances, new soft gray cabinetry, and an open-concept design flowing seamlessly into the dining room, living room and main-level office. A dramatic two-story tiled foyer with powder room welcomes you inside, while the spacious vaulted living room showcases a propane fireplace and beautiful white oak flooring that extends though the main living areas. The main-level primary suite offers a finished walk-in closet and beautifully updated bath. Upstairs are two additional bedrooms, one of which serves as a second option for primary ensuite, along with 2 additional baths. The finished lower level adds exceptional flexibility with storage, new mechanics an alcove area, another bath and the potential to use as a fourth bedroom or divide to use as a bedroom with additional game room/den, creating a comfortable 3-4 bedroom home configuration. A septic design for four bedrooms is already in place. The oversized attached two-bay garage includes a mudroom/laundry area, plus an additional windowed space ideal for a workshop, studio fitness room room, or private office. Major updates include new heating, air conditioning, roof, and more, providing peace of mind for years to come. Landscaping has intentionally been left open to the purchaser's vision with a $20K allowance in the purchase price, allowing creativity to compliment the property's beautiful stone walls and setting. This is a turnkey residence shall nurture and inspire for many years to come!

Listed by Laura Beckwith and Elizabeth Romano of Josiah Allen Real Estate, Inc.

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

178 High Meadow Road Winhall VT 05340

Winhall, VT178 High Meadow Road

Price$899,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5088923

  • Residential Single Family
  • Full Bath 2
  • Address 178 High Meadow Road
  • Bedrooms 5
  • Bathroom 4

POSTPONED OPENHOUSE Spacious 4,000± sq. ft. contemporary home located in a sought-after ski resort community with convenient winter shuttle bus access to the slopes. Designed for both entertaining and everyday comfort, this property features an open-concept floor plan, abundant natural light, and generous living spaces throughout. The inviting family recreation room with bar offers the perfect setting for gatherings, game nights, or relaxing aprs-ski evenings. Additional highlights include a screened in porch , heated two-car garage, multiple entertaining areas, expansive deck and a seamless blend of mountain charm and modern design. Additional detached workshop on sight for all your storage needs. Ideal as a primary residence, vacation getaway, or investment property in a premier four-season destination. Stratton Fitness Ctr bond available to purchase.

Listed by Terry Hill of Berkshire Hathaway HomeServices Stratton Home

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

2572 Morse Hill Road Dorset VT 05251

Dorset, VT2572 Morse Hill Road

Price$899,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5090583

  • Residential Single Family
  • Full Bath 2
  • Address 2572 Morse Hill Road
  • Bedrooms 4
  • Bathroom 3

Set along the rise of Morse Hill Road, this Dorset home has the quiet gravity of a place that feels discovered rather than merely shown. It carries the attributes buyers most often hope to find here: privacy, scale, high ceilings, fireplaces, a substantial bedroom count, ski access, village proximity, and a layered mountain outlook beyond the road, where the ridgeline appears through the trees and gives the setting a quiet sense of distance and place. The property offers 10 mostly wooded acres, creating a natural sense of enclosure without feeling removed from daily life. Mature trees, hillside contours, shifting light, and the broader landscape of the Green Mountains give the setting an atmosphere that feels composed, grounded, and deeply connected to its surroundings. Dorset Village, Manchester, Bromley, and Stratton are all within easy reach, allowing the home to live equally well as a full-time residence, weekend retreat, or four-season attended house. Inside, the home has presence. Expansive living spaces, natural materials, high ceilings, and multiple fireplaces create volume without sacrificing intimacy. The layout allows for both gathering and retreat, with room to support guests, work, family, and the kind of longer stays that happen when a house simply works. There is a particular rhythm this property suggests: slow mornings, winter fires, dinners after long days outside, quiet workweeks, full ski weekends, and seasons marked more by landscape than schedule. It is substantial without being showy, private without being isolated, and grounded in the understated elegance that makes Dorset so enduringly desirable.

Listed by Hayleyanne Van Der Kar of Four Seasons Sotheby's Int'l Realty

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

24 VT Route 11 Landgrove VT 05148

Landgrove, VT24 VT Route 11

Price$895,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5038367

  • Residential Single Family
  • Full Bath 5
  • Address 24 VT Route 11
  • Bedrooms 6
  • Bathroom 8

Some properties simply hold stories within their walls. Formerly the beloved Nordic Inn, this iconic Landgrove property has been thoughtfully reimagined into a gathering place designed for modern Vermont living while honoring its rich history of hospitality, adventure, and connection. Inside, six ensuite bedrooms, spa-inspired baths, multiple fireplaces, a chef's kitchen, sun-filled all-season room, and a cellar tavern and game room create spaces that feel welcoming in every season. The separate two-bedroom guesthouse offers additional flexibility for hosting family and friends after long days spent exploring the mountains and surrounding countryside. From winter mornings skiing Stratton, Bromley, Magic, or Okemo to summer afternoons at Lowell Lake, nearby trails, swimming holes, galleries, farmers markets, and outdoor concerts, life here naturally follows the rhythm of Vermont's changing seasons. Evenings return home beside the fire, gathering over dinner, sharing stories, and settling into the quiet beauty of the Green Mountains. Set along scenic Route 11 near the Catamount Trail and just a short drive to Manchester and Weston, this is more than a home. It is a place to create traditions, welcome generations, and experience Vermont at its most timeless and authentic. Floor plans and video tours available online. All measurements approximate.

Listed by Nancy Jensen and Lavinia Lee Brown of Four Seasons Sotheby's Int'l Realty

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

636 Dexter Road Shaftsbury VT 05262

Shaftsbury, VT636 Dexter Road

Price$875,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5083102

  • Residential Single Family
  • Full Bath 1
  • Address 636 Dexter Road
  • Bedrooms 4
  • Bathroom 3

In 1922, poet laureate and Shaftsbury resident Robert Frost was inspired by the bucolic local backroads to write “Stopping by the Woods on a Snowy Evening." The Dexter Road Farmhouse, dating back 225 years, remains a testament to the enduring charm of Vermont and the simpler rhythms of country life. Nestled at the end of a serene, tree-lined town road, this charming 1800 farmhouse captures the timeless beauty of rural Vermont. With sweeping vistas, peaceful surroundings, and a perfect balance of seclusion and convenience to all the Northshire region has to offer, this property is a rare gem. Lovingly cared for by the same family for over 70 years, the home retains much of its original character and craftsmanship, including wide pine flooring, original moldings, classic woodwork, and a gracious entrance hall. Traditional wall and ceiling boards further enhance the home's authentic farmhouse allure. With 40 acres more or less and a picturesque skating pond, there's ample room to explore, garden, or enjoy the pastoral landscape. The spacious layout features 4 bedrooms, 3 bathrooms, an inviting country kitchen, a formal dining room, a living room with a wood-burning fireplace, a library, and a bonus room. The windowed office on the lower level overlooks the pond and includes a Murphy bed. We invite you to discover the timeless appeal of this exceptional property, explore the quiet beauty of Shaftsbury, and consider making this charming farmhouse your home in Vermont.

Listed by Kristin Comeau and Elliott Nachwalter of TPW Real Estate

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1731 Three Maple Drive Manchester VT 05255

Manchester, VT1731 Three Maple Drive

Price$875,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5086027

  • Residential Single Family
  • Full Bath 3
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,237

Welcome to this beautifully maintained log home nestled on a open four-acre lot in the heart of Manchester Center. With over 3,200 square feet of thoughtfully designed living space, this 4 bedroom, 3.5 bathroom residence delivers the perfect blend of rustic charm and modern comfort. Step inside to discover a stunning great room anchored by a stone fireplace, soaring windows that flood the space with natural light, and a charming loft overlooking the gathering area below. The sun-drenched kitchen features a gorgeous center island with views of the backyard, flowing seamlessly into an intimate dining room ideal for memorable meals. The main-floor primary bedroom suite offers sliders leading to a spacious deck, while the private bath boasts a generous jacuzzi tub and shower for ultimate relaxation. A separate in-law suite on the first floor provides flexible living arrangements for extended family or guests. Upstairs, three additional bedrooms, a full bath, and a cozy sitting area ensure everyone has room to spread out. A four-car garage with additional basement storage rounds out the practical amenities. Outside, the generous acreage presents endless possibilities for gardens, play areas, or evening bonfires. Sip your morning coffee on the front porch while taking in seasonal mountain views, or lace up your boots and explore the neighboring conservation area trails. Located near the Southern Vermont Arts Center and all of Manchester's shops and restaurants, this property pairs country living with cultural enrichment. Quality craftsmanship topped with a brand-new roof makes this one worth seeing. Schedule your private tour today.

Listed by David Citron and Julie Citron of RE/MAX Four Seasons

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2026 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. Data last updated June 9, 2026 2:26 PM EDT

 

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