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Bennington County

551 West Fields Road Manchester VT 05254

Manchester, VT551 West Fields Road

Price$10,300,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5052301

  • Residential Single Family
  • Full Bath 3
  • Address 551 West Fields Road
  • Bedrooms 6
  • Bathroom 9

Discover "the pinnacle of luxury living" in the heart of Manchester Village! Crafted by Breen Builders and Ramsay Gourd Architect, every detail reflects superior craftsmanship and timeless elegance! From the very foundation to the finishing touches, attention to detail and commitment to quality shine through! Experience the perfect blend of luxury and convenience in this stunning 10,000 sq.ft estate where impeccable artisanship meets breathtaking mountain views! This architectural masterpiece offers the serenity of nature with privacy and supple views! This is more than a home, it is your private retreat with the world at your doorstep! Additional 10 acre abutting lot also available for purchase. See attached video for property tour.

Listed by Sunny Breen 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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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.

515 West Fields Road Manchester VT 05254

Manchester, VT515 West Fields Road

Price$5,900,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4974441

  • Residential Single Family
  • Full Bath 3
  • Address 515 West Fields Road
  • Bedrooms 5
  • Bathroom 6

Enduring values expressed in stone and wood! VERMONT CRAFTMANSHIP...A WORK OF ART!! Offering a private haven just minutes from downtown, in the heart of Manchester Village, nestled in the foothills of Equinox Mtn. is this rare and exceptional 5-bedroom, 6-bathroom home....The creative design of Architect Ramsey Gourd and Master Builder Mark Breen, well known as two of Southern Vermont's best, along with a dream team of highly skilled craftsmen, all passionate Masters of their own trade, and the result is quite simply....BREATH TAKING!!! The serpentine driveway is bordered by Maples, Birches, Pines and curves gracefully up to the cloistered court yard. Step through the front door into a wide foyer adorned with a gallery of floor to ceiling windows which further enhances the intimacy between the home's interior aesthetic and natural landscape. The home's showstopper has to be its jaw-dropping Great Room, thoughtfully designed as the heart of the home, this massive space accommodates kitchen, dining and living under a vaulted, 26 ft ceiling accented with hand-sawn wood beams. It features an incredible Chef's kitchen at one end and a floor-to-ceiling fire place at the other. The kitchen boasts a 17-foot book matched soap stone clad island seating for 6-8 and light filled sunny breakfast nook. With an outdoor kitchen, fire pit, built in water fall soaking pool, 5 verdant acres, tastefully blends with its idyllic valley setting, serenity is sublime!!!

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

{$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.

1060 Upper Hollow Road Dorset VT 05251

Dorset, VT1060 Upper Hollow Road

Price$5,600,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5075285

  • Residential Single Family
  • Full Bath 1
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 4,674

'MOONLIGHT REFLECTIONS ON AN UPPER HOLLOW SANCTUARY'... This stunning rare estate sits on 66 secluded acres of unspoiled beauty, offering breathtaking sweeping views of two luminous ponds, where moonlight reflections shimmer across the water each evening, creating a truly magical feeling. Inside you will find a contemporary open layout anchored by a dramatic stone fireplace, perfect for cozy evenings. The main residence captures the landscape from every angle blending modern architecture seamlessly with nature. This is much more than a home, it is truly a legacy property... Prestigious, Private and Profoundly Peaceful and must be seen to be fully appreciated!! Beauty, solitude, quiet luxury!!! Subdivision potential.

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

{$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.

1182 1184 East Manchester Road Manchester VT 05255

Manchester, VT1182 1184 East Manchester Road

Price$4,995,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5063499

  • Residential Single Family
  • Full Bath 5
  • Bedrooms 9
  • Bathroom 10
  • Square Feet 7,900

Peacock Hollow, a c.1790 completely private estate, is gracefully sited on 29.9 acres surrounded by sweeping mountain views, a running stream, and bordered by the forest. This rare offering combines historic character with refined updates, creating a legacy property designed for both intimate living and grand entertaining. The 5,500 square foot main residence offers five beautifully appointed bedrooms, five fireplaces, original wood and marble floors, and handsome moldings throughout. The home has been thoughtfully expanded to include a sun-filled country kitchen with custom cabinetry, formal and informal dining rooms, a library, family room, and multiple living spaces that open to marble terraces and gardens. Enhancing the estate are extraordinary amenities, including a marble in-ground swimming pool with stone terrace, a tennis court, and a one-bedroom caretaker's cottage with attached garage for on-site management or guest overflow. A 2,400 square foot three-bedroom guest house, created from the original c.1796 post-and-beam barn, blends historic charm with modern comfort. A goat and chicken barn, equipment barn, and a separate 30' x 60' seven-bay toy and car barn provide abundant storage and the opportunity for a true Vermont farmstead lifestyle or a spectacular car collection. The grounds are equally captivating, featuring mature landscaping, open meadows, orchards, perennial gardens, and stone walls. Pergolas, walkways, and extensive marble terraces.

Listed by Betsy Wadsworth 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.

527 Benson Road Manchester VT 05255

Manchester, VT527 Benson Road

Price$4,975,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5011880

  • Residential Single Family
  • Full Bath 1
  • Address 527 Benson Road
  • Bedrooms 5
  • Bathroom 4

Boorn Brook Farm combines the rich character of history and the comfort of contemporary living with complete privacy. Established in the late 1700s, the estate near Manchester Center offers stunning views of the Mt. Equinox and the Taconic Range. Surrounded by the Green Mountain National Forest, it creates a peaceful haven that balances the old and the new. For over 50 years, Marion Gould Pleissner lived at the Plaza in New York City and summered here while her husband, celebrated artist Ogden Pleissner, used the barn as his studio-his works now hang at the Met, Shelburne Museum and in private collections. The 1790s farmhouse and 1820s barn underwent extensive renovations by Boston architects Judge, Skelton, Smith. The farmhouse was thoughtfully restored, while the barn was transformed into two living spaces. Modern updates, including new utilities and underground infrastructure, were discreetly integrated to preserve the pristine vistas. The Great Room of the Barn have seen many lively gatherings over the years. Today, this multi-generational sanctuary remains a tranquil retreat, bordered by Bourn Brook and encircled by the GMNF's Lye Brook Wilderness Area. The property retains its pastoral allure with goats grazing the fields and timeless pleasures like fly fishing, hiking and swimming. Currently serving as a family compound and wedding venue, the property holds an Act 250 permit for up to 43 cabins. For more details, refer to the commercial listing.

Listed by T Story Jenks of LandVest, Inc/Woodstock, Wade Weathers of LandVest, Inc-Burlington

{$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.

220 Camptown Road Manchester VT 05255

Manchester, VT220 Camptown Road

Price$3,475,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5082096

  • Residential Single Family
  • Full Bath 4
  • Address 220 Camptown Road
  • Bedrooms 5
  • Bathroom 5

Set high on a hillside overlooking a picturesque horse farm, this exceptional Manchester property captures far-reaching mountain views and covetous privacy. Nearly 39 acres of sweeping lawn and open meadow transition into wooded terrain, with direct access to over 1,000 acres of conserved land leading to Mount Equinox and Myrick Mountain in the Equinox Highlands. Trails on the property and star-filled skies complete the setting. The home reflects thoughtful renovations and careful upkeep, designed to take full advantage of its surroundings. At the center, the kitchen opens to both a screened porch and a covered porch for year-round enjoyment of the views. A double oven, farmhouse sink, and bar area support easy living and entertaining. The living room features a wood-burning fireplace, while a separate library or office with fireplace and French doors leads to a private patio. The layout is both practical and flexible, with a primary suite on the main level and an additional suite upstairs, well-suited for multi-generational living or long-term ease. Three guest rooms provide ample space for all. A spacious mudroom connects to a combined pantry, laundry, and pet area, designed with everyday functionality in mind. The attached two-car garage includes a workshop and unfinished space above with heat and AC in place. A separate barn provides generous storage. The whole house generator is in place for backup power. Many recent upgrades have been completed, with a list available.

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.

68 Green Peak Orchard S. Dorset VT 05253

Dorset, VT68 Green Peak Orchard S.

Price$3,285,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5081997

  • Residential Single Family
  • Full Bath 4
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 6,900

Located in the desirable Green Peak Orchard, this exceptional custom Greek Revival residence is set on 9.9 private acres surrounded by mature landscaping, stone walls, and terraces. Thoughtfully designed with timeless craftsmanship, the home features wide-plank floors, hand-plastered walls and ceilings, custom moldings, historic reproduction lighting, and finely crafted wainscoting and cabinetry. Slate and copper roofs, along with Vermont marble and soapstone, enhance the home's distinctive character. A welcoming brick-floored mudroom opens to the heart of the home-an expansive, sun-filled chef's kitchen with butler's pantry, dining area, and bar, all with direct access to a charming kitchen garden for fresh herbs and seasonal blooms. The adjoining keeping room with fireplace flows seamlessly into a rustic family/sunroom highlighted by a striking Vermont fieldstone fireplace. French doors from both spaces open to a gracious slate terrace, creating ideal indoor-outdoor living. A book-lined library offers a quiet retreat, while a first-floor bedroom with en suite bath provides comfort and flexibility for guests. Upstairs, the primary suite features a spacious spa-like bath. Three additional bedrooms and two full baths offer ample accommodations. Radiant heat throughout ensures year-round comfort. The grounds are equally impressive, with curated landscaping, stonework, outdoor shower, and hot tub for relaxing under the stars. Completing the property is a two-story attached party barn/workshop, an attached two-car garage with loft storage and attached garden shed. A rare offering combining classic New England elegance with modern comfort-must be seen to be fully appreciated. All measurements approximate.

Listed by Carol O'Connor 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:

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.

2334 Morse Hill Road Dorset VT 05251

Dorset, VT2334 Morse Hill Road

Price$3,000,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5083576

  • Residential Single Family
  • Full Bath 2
  • Address 2334 Morse Hill Road
  • Bedrooms 2
  • Bathroom 4

Beautiful Dorset Contemporary Offering Privacy, Comfort, and Easy Living. If you've been looking for a private Vermont retreat with room to relax, entertain, and enjoy the beauty of every season, this exceptional custom home may be the perfect fit. Built in 1996 by respected Dorset builder Keith Dodson, this thoughtfully designed 5,731 sq. ft. contemporary sits on 12.15 peaceful acres with a pond and detached four-car garage. Inside, the home offers a welcoming and comfortable layout with 9 rooms, hardwood floors, radiant heat, central air with four zones, and a partial-house generator for added peace of mind. The kitchen features cherry cabinets, Corian countertops, a large island, cathedral ceiling, and easy access to the screened porch, an ideal spot for morning coffee or quiet summer evenings. The dramatic great room creates a wonderful gathering space, with its soaring two-story cathedral ceiling, skylights, exposed beams, built-ins, window seats, and balcony overlook. Throughout the home, warm details such as vertical pine walls, granite stone-faced fireplaces, and generous natural light add character and charm. The exterior combines cedar siding, granite stone accents, and a slate roof for lasting beauty and durability. A detached four-bay garage with direct entry and second-floor storage adds convenience and flexibility. This is a special property for those seeking quality construction, privacy, and a relaxed country lifestyle in one of Vermont's most desirable settings.

Listed by David Halligan 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.

59 Garden Loop Road Winhall VT 05340

Winhall, VT59 Garden Loop Road

Price$2,950,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5085635

  • Residential Single Family
  • Full Bath 1
  • Address 59 Garden Loop Road
  • Bedrooms 4
  • Bathroom 5

Move into this brand new stunning custom contemporary set on over 3 acres in coveted Stratton ski country. This exceptional modern design offers elevated living with superior craftsmanship and sweeping endless views. Featuring four well appointed ensuites with polished baths boasting radiant heated floors, half bath, family room and dual laundry areas. The well designed kitchen with Italian custom cabinetry offers an impressive honed granite island, Thor oven and 6 burner cooktop, Bosch dishwasher, Zline frig/freezer. Beautiful French oak floors throughout. Brizo hardware. Sonos sound system. Air conditioning. HVAC system is variable refrigerant flow (VRF). Weather Shield windows and doors. Heated two car garage. HOA fees include road and driveway maintenance, caretaking, lawn care and private winter shuttle service to Stratton's base lodge. We are nearing completion of Luna Thermowood exterior siding work with landscaping including blue stone patio next. (added digital image of lawn) Stylishly furnished. Experience captivating sunsets from most rooms, your deck and covered porch. We welcome your interest and enthusiasm, come take a look. This is not just a home but a mountain statement.

Listed by Terry Hill of Berkshire Hathaway HomeServices Stratton Home

{$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.

466 Three Maple Drive Manchester VT 05255

Manchester, VT466 Three Maple Drive

Price$2,875,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5065200

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 5
  • Square Feet 3,059
  • Acreage 3.85

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 suites, each with its own private bath, along with an additional half bath on the main level and a ¾ bath in the expansive bonus room above the garage-perfect for a guest suite, office, or studio. The heart of the home is an open-concept kitchen, dining, and living area filled with natural light from oversized windows and designed for effortless entertaining and everyday living. High-end tile work, thoughtfully chosen countertops, and custom finishes create a sense of understated elegance throughout the kitchen and bathrooms. Built with quality and longevity in mind, this home is truly turn-key-from its clean, contemporary farmhouse style to its well-considered layout and luxurious touches. Whether you're seeking a primary residence, a second home, or a Vermont retreat, this property offers it all. Enjoy the peace and privacy of country living while being just 5 minutes from downtown Manchester, close to Dorset, and surrounded by some of the area's best walking and hiking trails. Luxury, comfort, and an unbeatable location-this home checks every box.

Listed by David Shehadi of Josiah Allen Real Estate, Inc.

{$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.

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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 8:53 AM EDT

 

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