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Very Cool Houses

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B Prospect Street Manchester VT 05254

Manchester, VTB Prospect Street

Price$1,425,000

Est. Mortgage: $/month

MLS Number 5094369

  • Land
  • PricePerSqFt 37500
  • Address B Prospect Street
  • Acreage 38
  • Area VT-Bennington

A rare opportunity to own 38 stunning acres in the heart of Manchester Village, offering the perfect balance of seclusion, natural beauty, and convenience. A long, winding serpentine driveway gracefully leads to a beautifully manicured and ready-to-build homesite, creating a dramatic and private approach. Thoughtfully improved with underground power brought directly to the building site, a well, and a 7-bedroom septic design, this property allows you to begin planning your dream home immediately. As you explore the property, you'll discover a peaceful stream and a beautiful maple grove, enhancing its classic Vermont character and year-round natural appeal. From the homesite, enjoy magnificent views of Mt. Equinox and the Green Mountains to both the east and west, capturing breathtaking sunrises, sunsets, and the beauty of Vermont's changing seasons. A private trail from the property leads directly to Equinox Pond, where it connects to an extensive network of hiking trails. Privacy, views, and location come together in this truly exceptional offering.

Listed by Sunny Breen of Josiah Allen Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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932 Mcnamara Road Dorset VT 05251

Dorset, VT932 Mcnamara Road

Price$1,425,000

Est. Mortgage: $/month

MLS Number 5058749

  • Residential Single Family
  • PricePerSqFt 362.5
  • Full Bath 3
  • Address 932 Mcnamara Road
  • Construction Existing

It's SUMMER in Dorset and Manchester Vermont and this home screams opportunity ! NEW ROOF and exterior maintenance all updated for new owner! Situated in a most beautiful 5.4 acre setting of mature trees, landscaping and privacy, tucked away at the end of a gently curved, tree-lined drive. Located just over the Manchester Dorset town line, where Three Maple Drive becomes MacNamara, you'll experience the rare combination of private country living with the convenience of being in the Manchester Village or Dorset Village in 5 minutes. This well built and maintained residence offers an abundance of space and an open floor plan ready for you to create your legacy home. Inside, locally sourced marble floors flow into rich cherry hardwoods, setting the tone for quality throughout. Soaring ceilings extend from the foyer into the formal living room with a wood-burning fireplace and into the relaxed family room, where a second fireplace with a dramatic floor-to-ceiling brick hearth creates a warm gathering space. The formal dining room opens to an expansive eat-in kitchen, designed with generous counter space for cooking, entertaining, and daily living. The serene primary suite offers oversized windows and a charming pellet stove, while the spa-like bath includes a soaking tub, walk-in shower, double vanity, and ample closets. A private guest suite with its own bath and a laundry/utility room complete the first floor. Upstairs are two additional guest bedrooms, a full bath, and a spacious recreation room with wet bar and wood finishes-ideal for a pool table or media space. A detached, heated and cooled studio offers the perfect home office, art studio, or retreat. Nestled on 5 picturesque acres and just a short stroll to the Equinox Highlands Natural Area, this property balances sophistication, comfort, and Vermont lifestyle.

Listed by Britt Wohler of WOHLER REALTY GROUP, Martina Dvorak-Grattan of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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610 Route 100 Plymouth VT 05056

Plymouth, VT610 Route 100

Price$1,400,000

Est. Mortgage: $/month

MLS Number 5093857

  • Land
  • PricePerSqFt 5584.36
  • Address 610 Route 100
  • Acreage 250.7
  • Area VT-Windsor

Imagine owning 250 acres of unspoiled land in Vermont's coveted Lake Region, featuring five separate access points to the crystal-clear waters of Echo Lake. Whether you're envisioning a private family retreat, a recreational paradise, a conservation property, or a future development opportunity, this remarkable offering offers endless possibilities. Miles of established trails wind through the property, leading to open meadows, historic stone walls, and diverse terrain rich with natural beauty. Create a spectacular estate with sweeping views of the surrounding lakes and distant mountain ranges, or preserve the land's natural character and enjoy unmatched privacy within your own woodland sanctuary. Outdoor recreation is at your doorstep. Echo Lake offers boating, fishing, and swimming, while Camp Plymouth State Park sits just across the water. The VAST snowmobile trail network is nearby, and Vermont's premier ski destinations are within easy reach, with Okemo Mountain less than five miles to the south and Killington Resort approximately ten miles to the north. The charm of quintessential New England is all around, with the picturesque villages of Woodstock and Weston just a short drive away, offering fine dining, shopping, theaters, and year-round community events. This is a rare opportunity to own one of Central Vermont's truly exceptional legacy properties. Visit the Okemo real estate community today. Taxes are based on the current town assessment.

Listed by Kevin Barnes of William Raveis Real Estate Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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81 Town Farm Road Ludlow VT 05149

Ludlow, VT81 Town Farm Road

Price$1,400,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5096704

  • Residential Single Family
  • PricePerSqFt 639.27
  • Full Bath 3
  • Address 81 Town Farm Road
  • Construction Existing

Experience the essence of Vermont mountain living in this exceptional five-bedroom, four-and-a-half-bath retreat, ideally located just minutes from Okemo Mountain Resort and offering partial winter views of the mountain. Nestled on approximately one acre and boasting over 3,300 square feet of beautifully finished living space, this inviting home combines timeless mountain character with the comfort and amenities today’s buyers seek. From the moment you enter you will notice a soaring cathedral ceiling, natural woodwork, abundant natural light, and stunning wide-plank wood floors that create a warm and welcoming atmosphere. The spacious living room serves as the heart of the home, where a beautiful fireplace invites family and friends to gather after a day of skiing, hiking, golfing, or exploring Vermont’s four-season recreation. Designed for both everyday living and entertaining, the well-appointed kitchen features stainless steel appliances, beautiful cabinetry, and generous workspace for preparing everything from casual breakfasts to holiday meals. The private primary suite offers a relaxing sanctuary, while four additional bedrooms and multiple baths provide ample space for family and guests. The lower-level family room is the perfect destination for game nights and aprs-ski gatherings, complete with a billiard table and room to unwind. Step outside onto the expansive deck to enjoy fresh mountain air, seasonal views toward Okemo, morning coffee, summer barbecues, and evenings under the stars. A two-car garage offers convenient storage for vehicles and outdoor gear, while the home’s spacious layout comfortably accommodates large gatherings and memorable weekends. Whether you’re searching for a luxury vacation home, an investment opportunity, or a year-round residence, this remarkable property delivers the ideal blend of location, comfort, and mountain lifestyle in one of Vermont’s most sought-after destinations.

Listed by Matthew Bellantoni of Mary W. Davis Realtor & Assoc.,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

5347 Shelburne Road Shelburne VT 05482

Shelburne, VT5347 Shelburne Road

Price$1,400,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5097854

  • Residential Single Family
  • PricePerSqFt 201.96
  • Full Bath 8
  • Address 5347 Shelburne Road
  • Construction Existing

Step into Vermont hospitality with this well-maintained 1886 Victorian property in the heart of Shelburne Village, offering a rare hospitality real estate opportunity in one of Vermont's most desirable villages. Rich in historic character and updated, the property features nine well-appointed guest accommodations with updated en-suite baths, comfortable owner's quarters, a well-equipped inn kitchen, mature maple trees, perennial gardens, and original architectural details including hardwood floors, stained-glass windows, a preserved butler's pantry, decorative English tile fireplace surround, and original Burlington Blind Company shutters. Features include programmable electronic locks, two sprinkler systems, natural gas service, EV charging, and other infrastructure improvements supporting continued hospitality use. Located within the Village-1 Zoning District, the property operates as a permitted bed and breakfast, with single-family residential use also permitted subject to applicable approvals. Less than one mile from the Shelburne Museum, under two miles from Shelburne Farms, and within walking distance of restaurants, shops, the library, the Shelburne Farmers Market, and community events, the property is well positioned for continued hospitality or other permitted uses. Seller is a licensed Vermont real estate agent.

Listed by Lipkin Audette Team of Coldwell Banker Hickok and Boardman

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

67 Shallowbrook Road Jay VT 05859

Jay, VT67 Shallowbrook Road

Price$1,400,000

Est. Mortgage: $/month

MLS Number 5109540

  • Residential Single Family
  • PricePerSqFt 265.6
  • Full Bath 2
  • Address 67 Shallowbrook Road
  • Construction Existing

This expansive 5,271 sq. ft. residence offers a rare blend of space, comfort, and refined mountain living just 1.5 miles from Jay Peak Resort. Built in 1994, the home is permitted for five bedrooms, though the current owners chose to finish three, giving buyers the opportunity to expand or customize additional living space to suit their needs. With four bathrooms and a flexible layout, the property is ideal for large families or multi generational living. A dramatic grand staircase sets an elegant tone upon entry, leading to bright open living room and family room along with a dedicated dining room, all designed for gathering and entertaining. The main floor also includes a primary suite, offering convenience and privacy for owners or guests. The upper level also includes two additional bedrooms and office space, along with a spacious bonus room ideal for bunkbeds, a game room, an additional family hangout, or an arts and crafts space. A large deck overlooks beautifully landscaped grounds, creating a peaceful outdoor retreat, and the finished walk out basement is open and provides multiple areas for recreation, fitness, or guests, while also giving new owners the opportunity to add additional rooms, including the potential for extra bedrooms or an in law suite. An attached two car garage completes the property. The seller acknowledges that some minor cosmetic updates would further elevate the home and has priced accordingly, offering buyers an opportunity to personalize a substantial, well located property. Current photos do not fully highlight the scale, elegance, and potential of this impressive home, making an in person visit especially valuable. With its generous square footage, elegant architectural features, flexible layout, and unbeatable proximity to Jay Peak Resort's skiing, golf, waterpark, ice arena, and year round amenities, this home delivers a luxurious mountain lifestyle with exceptional value.

Listed by Mark English of Jim Campbell Real Estate @ Jay

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

1559 Swamp Road Fairfield VT 05455

Fairfield, VT1559 Swamp Road

Price$1,400,000

Est. Mortgage: $/month

MLS Number 5079104

  • Residential Single Family
  • PricePerSqFt 705.65
  • Full Bath 1
  • Address 1559 Swamp Road
  • Construction Existing

Discover an extraordinary opportunity to own 284.9 acres of Vermont countryside in the scenic town of Fairfield. This remarkable property offers a beautiful mix of open agricultural fields, mature woodland, and abundant wildlife, providing exceptional privacy and endless possibilities for recreation, farming, or a peaceful rural retreat. At the center of the property sits a historic farmhouse built in 1800, offering approximately 1,984 square feet with 4 bedrooms and 1 bathroom. The home is rich with character and presents a wonderful opportunity to personalize a classic Vermont farmhouse while enjoying the surrounding landscape. The expansive acreage provides excellent potential for agriculture, forestry, hunting, trail systems, and outdoor recreation. Protected through a Vermont Land Trust conservation easement, the land has been preserved to maintain its agricultural productivity, natural resources, and scenic beauty for generations while still allowing continued farming, forestry, recreation, and residential use in accordance with the easement. Despite its peaceful rural setting, the property is within driving distance of Jay Peak Resort and Smugglers' Notch, offering easy access to some of Vermont's best skiing, hiking, and four-season outdoor recreation. Large conserved tracts of land of this size are increasingly rare. Whether you're seeking a working agricultural property, recreational escape, or long-term land investment, this unique Fairfield property offers incredible potential and Vermont country charm.

Listed by Michael Preseau of CENTURY 21 North East

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1589 Main Street Cavendish VT 05142

Cavendish, VT1589 Main Street

Price$1,400,000

Est. Mortgage: $/month

MLS Number 5048760

  • Residential Single Family
  • PricePerSqFt 254.55
  • Full Bath 2
  • Address 1589 Main Street
  • Construction Existing

Glimmerstone Mansion, an extraordinary legacy estate where timeless elegance meets modern sophistication. Set on 2.4± beautifully landscaped acres, this iconic property, listed on the National Historic Register, has been meticulously restored, thoughtfully upgraded, and exquisitely furnished. At the heart of the estate is the grand 10-bedroom mansion, where nearly every bedroom and gathering space is graced with a stately fireplace, evoking the charm of a bygone era. Five bedrooms offer ensuite baths, each with spa-style finishes, while the owner's private apartment ensures comfort and privacy. Enjoy central air conditioning, high-speed internet, and cell service, ideal for today's work-from-home lifestyle. An entertainer's dream, the lower level reveals an English-style pub complete with a full bar and pool table, opening to an expansive bluestone patio. Step outside to relax in the 6 to 8-person hot tub, gather around the fire pit, or unwind on the gracious covered porch. The estate includes a fully equipped chef's kitchen designed for restaurant-scale culinary experiences and a beautifully renovated, 3,000-square-foot rustic barn, ideal for hosting events of up to 125 guests. Whether envisioned as a luxury retreat, corporate gathering space, or exceptional venue for weddings and celebrations, the possibilities are endless. Once a thriving bed and breakfast, this remarkable estate is ready for its next steward, whether as a private residence or a luxury hospitality venture. Visit the Okemo real estate community today. Taxes are based on current town assessment.

Listed by Kevin Barnes of William Raveis Real Estate Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

286 Coldbrook Road Wilmington VT 05363

Wilmington, VT286 Coldbrook Road

Price$1,400,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5073006

  • Residential Single Family
  • PricePerSqFt 571.9
  • Full Bath 4
  • Address 286 Coldbrook Road
  • Construction New Construction

This new construction home is in one of Southern Vermont's top four season destinations. Three homes are being built, with two still available, offering a great opportunity to secure a brand new home! The multi gabled modern farmhouse design blends clean architectural lines and warm natural materials. Ideally located just minutes from Mount Snow, the Hermitage Club, Harriman Reservoir, golf courses, and local amenities, this home suits a luxury second home, a strong investment property, or a comfortable year-round residence. The floor plan features a main level primary bedroom with an en suite bath and walk-in closet, plus what could be a second primary bedroom on the lower level with a full bath and direct walkout access to the covered patio. There are two more spacious bedrooms on the top level, each with its own full bathroom, and a bonus room for an office or extra sleeping space. Highlights include a two-story great room with a wood burning fireplace, a large covered porch, and an oversized attached two car garage. Buyers who commit early could personalize finishes within the builder's allowances or choose upgrades at their expense.

Listed by Melissa Nebelski of Real Broker LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

5347 Shelburne Road Shelburne VT 05482
Active With Contract

MLS Number 5098759

  • Commercial
  • PricePerSqFt 201.96
  • Address 5347 Shelburne Road
  • Year Built 1886
  • Square Feet 6,932

Step into Vermont hospitality with this well-maintained 1886 Victorian property in the heart of Shelburne Village, offering a rare hospitality real estate opportunity in one of Vermont's most desirable villages. Rich in historic character and updated, the property features nine well-appointed guest accommodations with updated en-suite baths, comfortable owner's quarters, a well-equipped inn kitchen, mature maple trees, perennial gardens, and original architectural details including hardwood floors, stained-glass windows, a preserved butler's pantry, decorative English tile fireplace surround, and original Burlington Blind Company shutters. Features include programmable electronic locks, two sprinkler systems, natural gas service, EV charging, and other infrastructure improvements supporting continued hospitality use. Located within the Village-1 Zoning District, the property operates as a permitted bed and breakfast, with single-family residential use also permitted subject to applicable approvals. Less than one mile from the Shelburne Museum, under two miles from Shelburne Farms, and within walking distance of restaurants, shops, the library, the Shelburne Farmers Market, and community events, the property is well positioned for continued hospitality or other permitted uses. Seller is a licensed Vermont real estate agent.

Listed by Lipkin Audette Team of Coldwell Banker Hickok and Boardman

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

26 Bridge Road Jay VT 05859

Jay, VT26 Bridge Road, Unit V144

Price$1,400,000

Est. Mortgage: $/month

MLS Number 5094775

  • Condo
  • PricePerSqFt 560
  • Square Feet 2,500
  • Bedrooms 5
  • New Contruction Existing

Opportunities like this don't come around often at Jay Peak. This spacious 5 bedroom, 4 bath condo sits just off the Grammy Jay ski trail, giving you true slopeside access in one of the mountain's most desirable spots. Owned by the same family since it was built and never rented, it shows a level of care that's hard to find. Inside, the main level offers an easy, open layout made for gathering a bright living area with a gas fireplace, a dining space that fits a crowd, and a well appointed kitchen with a new refrigerator. Large windows bring in soft natural light and views of the surrounding woods. A new furnace installed in 2024 adds peace of mind. Multiple bedroom suites are spread across different levels, giving everyone space and privacy. Additional bedrooms make hosting simple, and the layout handles larger groups without ever feeling cramped. And of course, this is Jay Peak known for some of the most abundant annual snowfall in the East. Step outside and you're moments from skiing, riding, hiking, and all of the resort's four season amenities, including the Pump House Waterpark, Ice Haus Arena, championship golf, restaurants, and miles of trails. It's one of the mountain's largest and most versatile condos in a true slopeside location.

Listed by Mark English of Jim Campbell Real Estate @ Jay

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

1589 Main Street Cavendish VT 05142

MLS Number 5102799

  • Commercial
  • PricePerSqFt 254.55
  • Address 1589 Main Street
  • Year Built 1860
  • Square Feet 5,500

Glimmerstone Mansion - an extraordinary legacy estate where timeless elegance meets modern sophistication. Set on 2.4± beautifully landscaped acres, this iconic property listed on the National Historic Register has been meticulously restored, thoughtfully upgraded, and exquisitely furnished. At the heart of the estate is the grand 10-bedroom mansion, where nearly every bedroom and gathering space is graced with a stately fireplace, evoking the charm of a bygone era. Five bedrooms offer ensuite baths, each with spa-style finishes, while the owner's private apartment ensures comfort and privacy. Enjoy central air conditioning, high-speed internet, and cell service-ideal for today's work-from-home lifestyle. An entertainer's dream, the lower level reveals an English-style pub complete with a full bar and pool table, opening to an expansive bluestone patio. Step outside to relax in the 6 to 8-person hot tub, gather around the fire pit, or unwind on the gracious covered porch. The estate includes a fully equipped chef's kitchen designed for restaurant-scale culinary experiences and a beautifully renovated, 3,000-square-foot rustic barn ideal for hosting events of up to 125 guests. Whether envisioned as a luxury retreat, corporate gathering space, or exceptional venue for weddings and celebrations, the possibilities are endless. Once a thriving bed and breakfast, this remarkable estate is ready for its next steward whether as a private residence or a luxury hospitality venture. Visit the Okemo real estate community today. Taxes are based on current town assessment.

Listed by Kevin Barnes of William Raveis Real Estate Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

Broker Reciprocity 

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 October 7, 2026 12:54 PM UTC