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Bennington County

Browse all available real estate in Bennington County, Vermont. 

Find Homes for Sale in Bennington County VT

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999 Route 30 Rupert VT 05761

Rupert, VT999 Route 30

Price$3,995,000

Est. Mortgage: $/month

MLS Number 4904677

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 5,094

Hagarbook Farm completely restored 5034 SF C. 1767 Residence consisting of magnificent Mettowee River frontage interior to the 320 acres, Hagar Brook and Waterfall, Harmons Mint Historic Site, Pond, Agricultural Fields, Extensive Trail System and View Sites galore! The Land Straddles both East Rupert and Dorset. Add significant buildings in lovely condition: 750 SF Guest House, Barn 37 X 100, Tractor Barn 26 X 50, Horse Barn 50 X 28 and additional out buildings--24 X 18, 20 X 14, 20 X 12, 16 X 12, 40 X 24! An exemplary eighteenth century compound approximately 3 miles north of the Dorset Green. The Great-Room Kitchen with exposed post and beam framing is the welcoming hearth of the home which walks out to the wrap around porch or sun room to the west where the living extends upon a wonderful level stone walled terrace overlooking the grounds and river beyond. Crisp architectural details witnessed in every room; Dining, Living, Family, Office and 4 Wonderful Bedrooms up. There are 5 baths, 2 half baths and a guest house ... Whether it's agricultural or equine interest, stream & field, auto collector, historical appreciation or family gathering ideals, this property is a treasure. Vermont Current Use real estate tax benefits for the next steward to embrace. 320 acres in the prized Mettowee Valley nearby Dorset!!!

Listed by Charles Mauro of Josiah Allen Real Estate,Inc.

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%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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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1251 West Road Manchester VT 05255

Manchester, VT1251 West Road

Price$3,495,000

Est. Mortgage: $/month

MLS Number 4912881

  • Residential Single Family
  • Construction Existing
  • Bedrooms 9
  • Bathroom 7
  • Square Feet 7,066

Do you like to entertain and host large crowds? Forever Farm is the setting! Have a sit down holiday dinner for many in the spacious cooks kitchen, retire by the wood paneled fireplace with an after dinner drink, or enjoy the covered porches during foliage. This Manchester compound situated conveniently to town shopping, restaurants, the Equinox resort and area ski mountains is a great year round gem! Work out daily in your home gym, skate on the pond during the winter months while family and friends hit the slopes! Bring one and all! The main home offers four guest bedrooms, two en-suite masters and a tastefully appointed three bedroom/two bath guest house above fully restored barn. This home is equipped with horse stalls, riding area and close to area trail systems. This is a rare offering.

Listed by Andrea Kaplan of Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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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440 Marcia Lane Dorset VT 05251

Dorset, VT440 Marcia Lane

Price$3,000,000

Est. Mortgage: $/month

MLS Number 4915207

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 8
  • Square Feet 8,700

This exceptional secluded country estate with breathtaking mountain views sits on a rolling hill in Dorset's exclusive Upper Hollow with 17.25 acres to explore. Showcasing the best in craftsmanship, sophisticated finishes, manicured stone patios, terraces, and walkways, makes this a beautifully refined residence. A custom wood beamed barn hosts an exclusive indoor basketball court and pool house that is beyond compare. Plans to renovate the current floor plan to open the spacious and welcoming gathering and entering space is underway. Whether you prefer a classically designed New England home or a more contemporary flow, the home boasts wide pine floors, crown molding, wainscoting, slate, marble and soapstone throughout. The living areas feature post and beam finishes and open to a covered wrap around porch and stone patio with an outdoor kitchen. The grand Master suite displays a dramatic Benson wood post and beam architecture warming the private retreat. You'll enjoy this special property for its ability to host all of your guests with 5 en-suite bedrooms, 3 wood burning fireplaces, and game room, you'll have plenty of room to gather, entertain or just lounge by the pool. Just 5 minutes to the Dorset Green with the Dorset Inn, Barrows House, Dorset Playhouse & the 3 Pear Gallery. With Bromley and Stratton Mountains just a short drive away, you'll enjoy Dorset and the mountains from this expansive and alluring property.

Listed by Kim Morgan-Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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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190 Turkey Run Lane Dorset VT 05251

Dorset, VT190 Turkey Run Lane

Price$3,000,000

Est. Mortgage: $/month

MLS Number 4941381

  • Residential Single Family
  • Bedrooms 5
  • Construction Existing
  • Bathroom 7
  • Square Feet 5,033

Simply an Extraordinary Dorset Hollow Estate. With breathtaking scenery, this magnificent property features a spacious main residence, 2 bedroom guest house, 50' in ground pool and pool pavilion- all situated amidst a spectacular setting at the top of Turkey Run Lane on 13.49 acres with sweeping views of Mountain Vistas and unrivaled sunsets.A masterful design and floor plan captures the surroundings with a most incredible three season room with high ceilings and unobstructed views of the Dorset Hollow. The grand living room, dining area, gourmet kitchen and family room are ideal for entertaining. This distinctive home features craftmanship of the highest quality with a design to enjoy all of Vermont's seasons: Enjoy a front row seat to fall foliage, the perfect sledding hill and bask in the sun around the pool. Multiple en-suite bedrooms, three fireplaces, wood floors, double garage, and mudroom bring ease to mountain living. With seamless access to the outdoors, the landscape design integrates the pool and pavilion with stone terraces, a bocce court, pergola and perennial gardens. An outdoor spa, shower and finished pool house compliment the summer experience.“Sleepy Hollow”, the guest cottage, offers private accommodations, with convenience to the main house. Dorset Village, Dorset Playhouse, Dorset Horse Show and endless outdoor recreation is at your doorstep. This is a one-of-a-kind property. Rare panoramic setting. Rare offering. Simply Extraordinary!

Listed by Kim Morgan-Wohler of Wohler Realty Group

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$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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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90 Snow Valley Road Winhall VT 05340

Winhall, VT90 Snow Valley Road

Price$2,950,000

Est. Mortgage: $/month

MLS Number 4939595

  • Land
  • Acreage 387
  • Utilities None
  • Zoning Rec

Discover the potential of an alpine escape beyond compare in Snow Valley. Once a beloved winter destination in gorgeous Southern Vermont, Snow Valley operated largely under the radar from 1939 to approximately 1982, with a proud reputation as one of the nations very first ski areas and the very first snowboard area. The stunning 390+ acre property forms an ideal blank canvas for potential future home or family compound with all of the benefits of a resort experience. The region boasts over 120 inches of snowfall per year, truly perfect for the downhill and cross-country skiing Snow Valley was once renowned for, with its north-facing configuration of mountains that funnel snow well into the spring season. Picture-perfect vistas of Vermont countryside stretch in every direction, Snow Valley is ready to exceed every expectation. Additional 60 acre lot available - PID 00489 - Span 771-245-1019 owned by Prospect Rock LLC.

Listed by Timothy Apps of Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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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141 Main Street Bennington VT 05201

MLS Number 4834579

  • Commercial
  • Year Built 1963
  • Square Feet 32,066
  • Acreage 4.29

Turn-key operation or development opportunity, you decide! Large and loyal clientele. Elegant property. Owner home on site. No commute to work. First time offered. PRICED TO SELL! The Paradise Motor Inn is located in Bennington, Vermont. Don't miss this unique opportunity to own one of the finest hospitality establishments in the heart of Southern Vermont. The property is well maintained and offers a variety of added values and experiences: extensive gardens and lawns, tennis courts, pool, and pickle ball. Ski, golf, or hike, all within a few miles from the Inn.

Listed by Marek Kovac and Paul William Carroccio of TPW Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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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74 High Meadow Road Winhall VT 05340

Winhall, VT74 High Meadow Road

Price$2,650,000

Est. Mortgage: $/month

MLS Number 4940403

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 5,460

This masterpiece of architectural and interior design is situated alongside the Stratton golf course with easy access to skiing. Recently re-decorated, the smart floorplan and incredible outdoor space defines this 3.6 acre estate at 74 High Meadow Road. The distinctive style is credited to original architect Mark P. Finlay, with extensive renovations by an exemplary firm that left no detail untouched. Eating at home is a delightful experience with the zen like ambiance in the kitchen, dining, and great room, with walls of windows and finishes in warm hues. Well equipped with a Viking 6 burner duel fuel stove, sub-zero fridge, and 2 dishwashers. The main floor primary suite is privately sited in the home and is akin to stepping into a luxury hotel room. The living room loft has views of the slopes, and a special place to read or make a home office. Exercise room and second laundry room is on the lower level. Three season screened porch, and destination fire pit. Central air-conditioning, radiant heat, backup generator, high speed internet, Crestron remote access system, 3 fireplaces, 2 sets of laundry, and 2 car garage are just a few of the essentials of this home. The site is a rare 3 contiguous lots, allowing you to build a guest house in the future, or enjoy the level lawns for snowmen or swing-sets. Path to golf course to snowshoe.

Listed by Christiane Carroccio of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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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1086 West Road Bennington VT 05201

Bennington, VT1086 West Road

Price$2,600,000

Est. Mortgage: $/month

MLS Number 4905858

  • Residential Single Family
  • Construction Existing
  • Bedrooms 9
  • Bathroom 7
  • Square Feet 6,956

Captivating French Provincial architecture is the hallmark of this 6,800 sq. ft 1866 Manor House occupying a commanding and picturesque view over 94 acres of pristine pastoral fields and the distant Taconic Mountain Range. The timeless and beautifully proportioned interiors feature extensive molding, solid oak flooring, eight fireplaces, nine bedrooms, seven baths, country kitchen and adjoining pantry, formal dining and living rooms. The private estate includes a three car garage, four bedroom caretakers cottage, artist studio and gunite in-ground pool. Set on the outskirts of the historic town of Bennington offering shopping, live theatre, restaurants, horseback riding and proximity to mountain and cross-country skiing. This is a rare opportunity to own an exquisite estate property with a myriad of possibilities as a family compound or country retreat. Only 45 minutes to Albany International Airport and approximately three hours to Manhattan and Boston. All measurements approximate.

Listed by Chris DeFelice and Elena Atwill of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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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1842 Main Street Manchester VT 05255

Manchester, VT1842 Main Street

Price$2,500,000

Est. Mortgage: $/month

MLS Number 4910977

  • Residential Single Family
  • Construction Existing
  • Bedrooms 11
  • Bathroom 13
  • Square Feet 10,877

An enchanting history describes a homestead at Ormsby Hill beginning in 1764 that was historically used to entertain friends a family during the summer months. It was one of the first Federal style mansions to be built in Manchester. Over the years, it evolved and grew to become a luxury Bed and Breakfast Inn with a superlative reputation for hospitality in beautifully appointed guest rooms and common areas. It has always catered to the romantic getaway market with fireplaces and whirlpool tubs in every guest room. Additions were built on the North end of the original building for more guest rooms and on the South end of the building to accommodate the owners of the inn in great style. Original hearths, incredible trim on ceilings and moldings, and great architecture make this property unique in its grandeur.

Listed by Wendy Beach of Hearthside Group

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$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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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528/540 Nichols Hill Road Dorset VT 05251

Dorset, VT528/540 Nichols Hill Road

Price$2,500,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4917068

  • Residential Single Family
  • Construction Existing
  • Bedrooms 8
  • Bathroom 6
  • Square Feet 4,186

Magnificent Offering... Quintessential Dorset Farm! 187 pristine acres in the heart of Dorset on coveted Nichols Hill! Mixture of beautifully managed meadows, sugarbush, woods, stream and pond in Current Use and The Vermont Land Trust. Equine or agriculture friendly with access to all lands through myriad of groomed trails. Incredible panoramic views are distant and intimate. Lovely Goodman Brook meanders thru the property and there is a small pond. Two very well appointed homes include the original farmhouse, a newer constructed cape, a large P&B antique barn and outbuilding in a picturesque tranquil setting. A 1850 2026 SF Colonial and a 1980 2160 SF Cape totals 4,186 finished square feet offering 8 bedrooms between the two homes. Understated elegance. Healthy Forestry Plan. Sellers have gone to great lengths to preserve the property and habitat. Vermont Land Trust owns the development rights but there is the ability for one more homestead within the property. Perfect for a family compound or off-set income potential. Forestry and Land Trust Docs available upon request. Superb View Setting... Bike Ride to Dorset Village... this is the ultimate offering base toward an amazing Dorset Compound!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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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308 Uphill Lane Dorset VT 05253

Dorset, VT308 Uphill Lane

Price$2,500,000

Est. Mortgage: $/month

MLS Number 4939833

  • Residential Single Family
  • Bathroom 7
  • Bedrooms 5
  • Construction Existing
  • Square Feet 8,835

Built in 1989 as a private home oasis, this home does not disappoint. With privacy, views, a heated pool, tennis court, and indoor sauna, your home becomes your own personal resort. Entertaining is a breeze with the open floor plan. Everyone can enjoy the preparing of meals in the large chef's kitchen seated nicely next to the dining room with a gorgeous propane fireplace. After a meal retire to the great room with the wood burning fireplace and large windows to views. Speaking of views, did you see the views? Visible from all the rooms facing east (Bromley Mountain). At the end of the first floor is an expansive gym that can be used for wrestling, dance, working out or repurposed for whatever the new buyer might desire. Oh, and the sauna! On the second floor, you will find the primary suite which comes complete with a large sitting area, separate dressing room, and an expansive bathroom with jetted tub and separate shower....and views! Three additional bedroom suites and laundry room complete the second floor. The third floor offers an additional living space with a bedroom, tv room, full bath (room to add a small kitchen) and an additional exterior stairway in addition to the interior stairway. In the warmer months, enjoy your own heated swimming pool and a game of tennis. All measurements are approximate.

Listed by Lynn Rawson of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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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8 Read Farm Road Dorset VT 05253

MLS Number 4900616

  • Commercial
  • Year Built 1965
  • Square Feet 4,141
  • Acreage 2.5

Chantecleer offers an opportunity to purchase a renowned & well-established restaurant. Chantecleer's celebrated status as the Green Mountain region's premiere fine dining experience consistently yields a significant seven figure annual revenue stream with service 4 evenings per week.The dining areas offer seating for 96 guests with dinner service ranging from 130-170 nightly, featuring a state of the art kitchen with new equipment. Lofty beamed ceilings adorned with sophisticated bronze chandeliers contribute to the dining room's dramatic, but highly functional setting. The well apportioned and full-service bar comfortably seats up to 12 guests, w/ additional table seating for 16.Along the busy 7A corridor, the location benefits from steady summer tourism and proximity to a multitude of ski resorts. Southern Vermont is both a winter and a summer destinations with The annual Dorset Horse Show, professional summer theatre and music festivals. The Wedding Business in strong and demand for a Vermont Venue is significant.If you are looking to create your own vision for a restaurant or hospitality business, this property has what it takes to be successful. Whether you seek to reinvent the existing restaurant offering, combine or partner with a micro-brewery, expand to include lunch and brunch, offer an outdoor summer patio and bar or become a wedding & event venue, the opportunity sets you front and center to pursue. Chantecleer is primed for the next owner-operator or investor.

Listed by Kim Morgan-Wohler and Britt Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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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Broker Reciprocity

Copyright 2023 New England Real Estate Network, Inc. All rights reserved. This display of listings may or may not be the entire Compilation from the NEREN database, and NEREN does not guarantee the accuracy of such information. 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 January 27, 2023 7:39 PM EST.

 
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