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Bennington County

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86 Church Street Dorset VT 05251

Dorset, VT86 Church Street

Price$2,850,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5091786

  • Residential Single Family
  • Full Bath 5
  • Address 86 Church Street
  • Bedrooms 5
  • Bathroom 6

Set on the north side of the Dorset Green, 86 and 78 Church Street present a rare village compound in the heart of Dorset. Fully renovated with exceptional attention to detail, this refined micro-estate blends timeless New England character with sophisticated modern living. Encompassing the main residence, guest cottage, gardens, and garage, the property is both gracious in scale and intimate in feel, the quintessential “new old house” imagined to perfection. Beautifully proportioned rooms are filled with warmth and elegance. The chef's kitchen features a walk-in pantry with prep sink and dishwasher, plus a dedicated coffee station and refrigerated drawers. The living room opens to a covered porch overlooking the Green, while the screened porch with a stone fireplace connects seamlessly to the dining room, deck, and patio for effortless indoor-outdoor living. A library hallway leads to a bright laundry room and stunning powder room. The billiards room and den offer richly layered finishes and a more intimate atmosphere. Original beams, remarkable millwork, wide-plank pine floors, two staircases, and generous hallways and landings create an effortless sense of flow throughout. The main residence includes two private primary suites, three additional guest bedrooms, marble baths, and beautifully curated gathering spaces. Outside, mature gardens, stone walls, a water feature, fire pit, and outdoor entertaining areas create a secluded retreat. A separate gym, spa, or hobby space opens directly to a tranquil zen garden. The charming three-bedroom guest cottage, complete with its own screened porch, offers ideal accommodations for guests or potential rental income. A singular offering where historic Dorset charm meets elevated village living on one of Southern Vermont's most iconic addresses.

Listed by Christiane Carroccio 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.

23 Valley View Road Winhall VT 05340

Winhall, VT23 Valley View Road

Price$2,800,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5053750

  • Residential Single Family
  • Full Bath 3
  • Address 23 Valley View Road
  • Bedrooms 3
  • Bathroom 4

Set at the end of a long, private driveway, this remarkable property unveils dramatic panoramic vistas that stretch nearly 40 miles. Offering a rare sense of seclusion & grandeur, the home is an ideal retreat where nature, privacy, and beauty converge.Designed w/a modern aesthetic,an expansive open-concept layout, the main floor features a stunning stone fireplace , enhanced by soaring ceilings and grand French doors that flood the interior w/ natural light. At the heart lies a chef's kitchen, equipped with premier appliances, spacious center island, custom cabinetry-ideal for both daily living and entertaining. Perfectly tailored for hosting, the home includes a dedicated cocktail and coffee bar-rich with wood accents.Step outside to enjoy the convenience of a full outdoor kitchen. Whether you're entertaining or unwinding solo, this porch is a year-round sanctuary.The luxurious primary suite is a private retreat, thoughtfully curated w/ high-end finishes and indulgent amenities.A spa-inspired ensuite bath,w/ an oversized hammered copper soaking tub invites relaxation, a sleek glass fireplace adds ambiance.From the breathtaking views, modern design, & refined blend of indoor-outdoor living this home offers a rare opportunity to experience mountain living at its finest. An entertainer's dream & a serene space to call home. this extraordinary residence invites you to slow down, settle in & savor every moment. Barn & Extraordinary Upgrades. SHOWINGS BEGIN SATURDAY AUGUST 2.

Listed by Kim Morgan-Wohler of Wohler Realty Group, Britt Wohler of WOHLER REALTY GROUP

{$office->Name}

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.

Lot 6 Stone Lodge Road Winhall VT 05340

Winhall, VTLot 6 Stone Lodge Road

Price$2,525,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5076149

  • Residential Single Family
  • Full Bath 3
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,536

SHOWINGS BEGIN at Thursday February 12. Premier New Construction, offering 4500+ SF of luxury living on three levels, perched on 2.5 acres to maximize panoramic mountain and Bromley views. Just minutes to the Stratton Resort Base Lodge, this exceptional 4 bedroom/3.5 bath floor plan combines contemporary design, craftsmanship of the highest caliber and energy efficiency.Thoughtfully designed for comfort and performance, each detail reflects quality craftsmanship-from the sleek finishes to the high performance systems. The handcrafted timber frame great room showcases the natural beauty of the Green Mountains. Defined by soaring cathedral ceilings and exposed natural wood beams, the dramatic wall of stone with wood hearth anchors the space while expansive windows frame breathtaking views, flooding the room with natural light. The designer c hef's kitchen with dedicated scullery is as elegant as it is functional with top tier appliances and and oversized island.A main level en suite primary features views, a walk in closet, and a spa inspired bath, double vanities and glass enclosed tiled shower.A second en-suite primary , occupies its own level with soaring ceilings, upscale tiled bath and peaceful separation from the rest of the residence. The finished lower level walkout provides flexible living with media/game room, and a 4th mega bunk or guest room and bath.The spacious entry welcomes guests, a mudroom and attached 2 car garage provide the spaces needed for Active Mountain Living with a second level expansion room already prepped for future heating, plumbing and electricity.Stone Lodge offers the balance between mountain serenity and the convenience of the Stratton Mountain Resort. Enjoy the comforts of a premier mountain retreat with easy access to year round recreation, dining and everything the area has to offer. Experience adventure , relaxation and the luxury of Stone Lodge!

Listed by Kim Morgan-Wohler of Wohler Realty Group, Britt Wohler of WOHLER REALTY GROUP

{$office->Name}

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.

3039 Route 30 Dorset VT 05251

Dorset, VT3039 Route 30

Price$2,495,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5089828

  • Residential Single Family
  • Full Bath 3
  • Address 3039 Route 30
  • Bedrooms 4
  • Bathroom 6

Tucked away at the end of a long, winding driveway, this remarkable Dorset Village estate sits on one of the area's largest parcels-over six private acres. A rare blend of privacy, history, and elegance, the home features four stunning stone fireplaces, exposed antique beams, reclaimed wood details, and abundant natural light throughout its flowing layout. Designed for gathering and making memories, it offers unique touches like theater-inspired stair railings and a vaulted-ceiling game room. Outdoor living is unmatched with a spacious wraparound deck, screened porch, wood-fired brick pizza oven, and a tucked-away sauna. The charming barn includes two horse stalls, a tack room, and room for more animals, plus a fenced paddock and serene pond. An oversized three-car garage adds functionality to this character-filled property. Just a short walk to town and trails, yet feeling worlds away-this is a one-of-a-kind Vermont estate.

Listed by Carrie Mathews of Winhall Real Estate

{$office->Name}

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.

543 Lower Hollow Road Dorset VT 05251

Dorset, VT543 Lower Hollow Road

Price$2,285,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5089892

  • Residential Single Family
  • Full Bath 4
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,647

A Serene Dorset Hollow Retreat Along the Mettowee River Tucked into the storied Dorset Hollow, this 4.6-acre retreat enjoys 488 feet of Mettowee River frontage, offering a rare blend of tranquility, comfort, and timeless Vermont charm. Expansive mountain views and the soothing sounds of the river surround you-fall asleep each night to its calming presence. Multiple outdoor spaces include a covered front porch, kitchen-side veranda, and a bluestone terrace that seamlessly connects to the open-concept living areas. The home is perfectly positioned for southern light and sweeping views, blending rustic elegance with modern sophistication. Inside, a dramatic two-story foyer and stone fireplace anchor the beautifully maintained residence. Large sliders flood the home with light, creating harmony between indoor and outdoor living. A granite chef's kitchen, dining room, and living room offer stylish functionality. The main-level primary suite features a spa-like bath and walk-in closet. A study and three ensuite bedrooms complete the living spaces. Enjoy the peaceful yard, fish from your private stream frontage, and take in the vibrant foliage or snowy fields. Thoughtful extras include a hot tub, finished bonus room above the garage, and an unfinished basement for future expansion. Just minutes from Dorset Village, this exceptional property offers peace, privacy, and a deep connection to the natural beauty of Southern Vermont.

Listed by Britt Wohler of WOHLER REALTY GROUP, Kim Morgan-Wohler of Wohler Realty Group

{$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:

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.

288 Cedar Lane Peru VT 05152

Peru, VT288 Cedar Lane

Price$2,275,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5061819

  • Residential Single Family
  • Full Bath 6
  • Address 288 Cedar Lane
  • Bedrooms 9
  • Bathroom 8

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 enjoyed fireside under the stars. The main residence boasts a flowing floor plan designed for entertaining, with large windows filling the home with natural light and framing water views from nearly every room. A brand-new septic system, built for seven bedrooms, ensures comfort and space for all. The oversized two-car garage provides ample storage for all your outdoor gear. Set apart among the trees, the guest cottage offers its own sense of retreat with vaulted ceilings, an open living space, two en-suite bedrooms, and an additional two-car garage. A short walking path leads directly to the water's edge. Located less than a mile from Peru's charming Hapgood Store and just 2 miles from Bromley Mountain, this property truly offers four-season enjoyment in the heart of Vermont. The current owner benefits from strong rental income when the properties are not being used for personal enjoyment

Listed by Jessica Citera of Cummings & Co

{$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:

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.

7537 Main Street Manchester VT 05255

Manchester, VT7537 Main Street

Price$2,200,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 5089601

  • Residential Single Family
  • Full Bath 2
  • Address 7537 Main Street
  • Bedrooms 4
  • Bathroom 4

Perched to capture sweeping easterly views of Vermont's mountains, this re-imagined Manchester home lives large. Completely renovated and redesigned in 2022, the pristine property blends timeless materials with modern comforts and efficiency. Danby marble, light oak flooring, high-end fixtures, and antique barn beams anchor the Great Room, while expansive windows fill the home with natural light and ever-changing mountain views. Open, spacious, warm, and inviting, the home was designed for easy living and connection to nature. Enjoy morning coffee from the porch swing as the sun rises over the mountains. Sweeping fenced lawns lead past the pond and into rising gladed woods, where trails wind through rock outcroppings, ferns, and the quiet beauty of more than 14 acres. Energy efficiency, thoughtful upgrades, and countless bells and whistles make daily living comfortable and effortless. Conveniently located near the recreation, dining, shopping, and cultural amenities of Manchester, Dorset and the surrounding mountains, the property feels both private and connected. Photos and the video only hint at the connection and serenity Upland Farmhouse offers. Seller requests no drive-bys please; privacy is appreciated and the property is monitored. Pre-qualified buyers are welcome to schedule a private appointment through their agent. All measurements approximate.

Listed by Elena Atwill of Four Seasons Sotheby's Int'l Realty, Nancy Jensen of Four Seasons Sotheby's Int'l Realty

{$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.

1228 Skiparee Road Pownal VT 05260

Pownal, VT1228 Skiparee Road

Price$2,100,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5008279

  • Residential Single Family
  • Full Bath 3
  • Address 1228 Skiparee Road
  • Bedrooms 4
  • Bathroom 3

Welcome to Amara Farm, an equestrian paradise in Southern Vermont. This meticulously planned property offers a 13-stall barn designed with every detail in mind, ensuring comfort and efficiency for both horse and rider. The state-of-the-art indoor arena features GGT footing and a full wall of window providing top-quality conditions for training and performance. Turnout paddocks and outdoor arena greet you with remarkable mountain views, creating a picturesque backdrop for your riding sessions.Explore the extensive trails on the 30 acres equipped with cross-country jumps and hills, perfect for leisurely rides or serious training. The four bedroom home is a luxurious respite from barn time. The open layout kitchen to living and dining also offers doors to a deck with a view of the mountains and gardens, and a screened porch. Wolf cooktop, walk in pantry, wet bar, and an oversized island make up a stellar kitchen. The office has views of paddocks with run-in sheds. The master suite has dual walk in closets, spa bathroom, and balcony. Lowest level of the home is a theater room, gym, and walks out to a covered patio and firepit. After a day of riding, cool off in the 'tubs' swimming hole. Barn has 2 bedroom apartment. Located just 15 mins from Bennington, VT, and 15 mins from Williamstown, MA, Amara Farm offers the perfect balance of rural tranquility and convenient access to nearby towns and equestrian competition venues. Don't miss this rare opportunity. Inquire for more details.

Listed by Christiane Carroccio 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.

655 Squirrel Hollow Road Dorset VT 05253

Dorset, VT655 Squirrel Hollow Road

Price$1,997,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5093536

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 4,125
  • Acreage 23.09

Set on 23 private acres with sweeping Green Mountain views, this contemporary residence by acclaimed architect Jeff Barnes is thoughtfully composed to engage its landscape at every turn. Walls of glass, soaring ceilings, exposed timber trusses, and stone fireplaces bring scale and warmth to the interiors, while broad windows draw in light and long views from nearly every principal room. Particularly noteworthy is the custom woodwork found throughout the house, from richly figured cabinetry and built-ins to warm wood window surrounds and graceful curved details that lend the home an uncommon sense of finish and refinement. The kitchen is both generous and inviting, with a substantial island, granite counters, panoramic views, and extensive custom cabinetry, and it opens easily to the dining and living rooms, a wet bar, an expansive deck, and a screened porch overlooking the pond and waterfall. A first-floor office or study with built-in bookshelves and a custom wooden desk provides a tailored workspace. Privately situated above the main living level, the primary suite includes a fireplace, sitting area, bath retreat, and far-reaching views. The lower level offers a spacious family room with fireplace and three guest bedrooms, while additional space above the garage is well suited to recreation, fitness, or studio use. Rarely does a house combine architectural pedigree, craftsmanship, and such a compelling Vermont setting with this degree of ease and livability.

Listed by Laura Kottler and Tim Post of LandVest, Inc/Woodstock

{$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.

2589 W. Sandgate Road Sandgate VT 05250

Sandgate, VT2589 W. Sandgate Road

Price$1,995,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 5047939

  • Residential Single Family
  • Full Bath 2
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 6,323

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 for reading, and late winter for tapping maples, reconnecting with the rhythms of nature. A wide porch gazes across to rounded hills. The screened porch, with its pass-through to the kitchen, is perfect for summer suppers. Under the dappled shade of trees, a walled stone terrace welcomes lingering meals and conversations that last into starlight. Perennial gardens bloom from early spring to autumn's last blaze. The kitchen is a true chef's haven-spacious and inviting, with an AGA range, Viking appliances, marble and soapstone counters, a walk-in pantry, and a tucked-away office. Wood-burning fireplaces anchor the library and living room. The primary suite has its own hearth; four more bedrooms offer room for guests. With a 7-stall horse barn, one bedroom studio/art space over the car barn with a commercial kitchen below, infinity pool, sauna house, solar array, greenhouse, trout pond, fruit trees and berries, this is more than a farm-it's a place to re-create. 30 minutes from Manchester/Dorset, 3 hours from New York and Boston. Showings begin June 27

Listed by Dia Jenks and T Story Jenks of LandVest, Inc/Woodstock

{$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 9:40 AM EDT

 

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