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Bennington County

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58 Mount Anthony Road Bennington VT 05201

Bennington, VT58 Mount Anthony Road

Price$599,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 5067086

  • Residential Single Family
  • Full Bath 1
  • Village Bennington
  • Bedrooms 3
  • Bathroom 3

Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c.1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can be surmised that this property was for the intent of upper management housing for the farm. With sprawling views to the north, south and west, this location does not disappoint! A typical farmhouse style home that esthetically blends rustic and modern elements for easy living. A generously sized kitchen is perfection for entertaining and for spending time with family and friends. The living room invites a space for conversation, a cozy fire during the chilly Vermont evenings, or simply relaxing taking in the divine views at sunset. More casually, the family room offers exposed beams, vaulted ceilings and abundance of natural light. A formal dining room is strategic to the kitchen for holidays and family gatherings. The second floor boasts three bedrooms and two bathrooms, while the third bath is on the first level for convenience. And have I mentioned the renovated space above the garage? Wow! Breathe in the fresh air, take a walk up a country road and hunker down for the most genuine, spectacular sunsets. This is the type of special property that you will not want to miss.

Listed by Monique Geannelis of Mahar McCarthy 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.

185 Kelleher Road Dorset VT 05251

Dorset, VT185 Kelleher Road, Unit 10-00-99

Price$599,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5090243

  • Residential Single Family
  • Full Bath 1
  • Address 185 Kelleher Road
  • Bedrooms 3
  • Bathroom 2

This Pretty White Cape is located on a low traveled dead end road right off Dorset's Morse Hill Road... equidistance to Manchester and Dorset and an easy walk to the newly transitioning Green Ridge Elementary K-5, for the 26-27 school year. Beautifully maintained, this residence offers a lovely open Dining/Kitchen /Living great-room with vault that beholds sunlight all day long. The quartz counters and white cabinets brighten up the space with corner windows around the dining area and new light wool carpet in the living room. This is a house that feels easy and light! There's a den/office and main level bedroom and bath. The living area walks out onto a deck... This house is in great condition. On the second level there are two spacious bedrooms and bath. There's a dry concrete basement for domestic mechanics and plenty of storage! The mudroom is quite ample and connects the house to the two car garage. The rear yard is fenced. Keep it Simple, Easy Living is Found Right Here!

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

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

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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.

21 Jameson Flats Manchester VT 05255

Manchester, VT21 Jameson Flats, Unit Duplex Unit B

Price$595,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5079271

  • Residential Single Family
  • Full Bath 2
  • Address 21 Jameson Flats
  • Bedrooms 3
  • Bathroom 3

THE PROGRAM: Purchase Price Assistance/ Mortgage Payment Reduction: Eligibility Requirements: * Vermont Residency or Residency at time of Purchase * First Time Vermont Homebuyer * Household Income at or Below $178,735* * Qualify for a Bank Mortgage * 10% Down Payment The developer will offer Gifted Equity and Paid Points at closing that will reduce the purchase price of the real estate and reduce the interest rate to 4%. All of this will reduce the monthly mortgage payment for qualified buyers. Homes Designed to Strengthen and Enrich the Manchester Community Jamesons Flats was thoughtfully developed to ensure that dedicated, skilled Vermonters have the opportunity to live, grow, and thrive right here in Manchester. A strong community depends on a stable and supported local workforce-and that begins with access to reliable, high-quality housing. Jamesons Flats offers beautifully crafted, energy-efficient homes designed with the full-time resident in mind, featuring garages, basements, and smart, functional storage throughout.

Listed by Britt Wohler of WOHLER REALTY GROUP, Trent Stephens of Wohler Realty Group

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

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Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

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

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

14 A Marisa Lane Dorset VT 05251

Dorset, VT14 A Marisa Lane

Price$584,900The price has recently decreased

Est. Mortgage: $/month

MLS Number 5085703

  • Residential Single Family
  • Full Bath 1
  • Address 14 A Marisa Lane
  • Bedrooms 3
  • Bathroom 3

Welcome to your next chapter in the charming heart of Vermont, where easy living meets thoughtful design in this beautifully crafted one-level duplex townhouse. If you've been dreaming of a home that eliminates stairs from your daily routine while still delivering style and substance, your search ends here. Step inside and discover an open floor plan that feels both spacious and inviting across 1,786 square feet of well-appointed living space. The kitchen is a true showstopper, featuring custom cabinetry and stunning wood countertops that bring warmth and character to every meal. A generous breakfast bar provides the perfect spot for morning coffee or casual entertaining with friends. Three bedrooms offer flexibility for every lifestyle. The primary suite is a private retreat complete with a walk-in closet and a beautifully tiled shower that adds a touch of everyday luxury. Two additional bedrooms stand ready to serve as guest quarters, a private home office, or a cozy den for unwinding after a long day. Two and a half bathrooms ensure everyone has the space they need. Practical perks abound with a two-car attached garage that keeps Vermont winters at bay and a full unfinished basement offering abundant storage or future finishing potential for the ambitious homeowner. The location is nothing short of delightful. Just five minutes from the picturesque Dorset Village green, you'll find yourself steps from the library, the beloved Playhouse, the Dorset Field Club, several fine dining establishments, and well stocked VT general stores. Manchester's popular bike trail and recreation park is just down the road with pool, running track, playgrounds, and ball courts. This is single-level living done right in one of Vermont's most beloved communities. Schedule your private showing today and experience it for yourself.

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

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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.

4 Pearl Buck Drive Winhall VT 05340

Winhall, VT4 Pearl Buck Drive

Price$579,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5082377

  • Residential Single Family
  • Full Bath 2
  • Address 4 Pearl Buck Drive
  • Bedrooms 3
  • Bathroom 2

Just minutes from the slopes of Stratton Mountain Resort, this three bedroom plus den, two bath home offers an easy four season retreat with stunning views of Stratton Mountain. Set on 2 acres, it gives you convenient access to everything the area is known for, from winter ski days to summer mountain biking, golf, hiking, and village events. The home has been thoughtfully improved over time, offering a comfortable mix of mountain charm and practical updates. A newly built deck creates the perfect place to take in the view, while inside, a Vermont Castings wood stove brings warmth and character to the vaulted living space, it's ideal for cozy apres-ski evenings. The efficient layout makes for easy maintenance, and the attached two-car garage provides excellent storage for skis, boards, bikes, and outdoor gear. Offered furnished for added convenience, this is an easy opportunity to settle in and start enjoying the Stratton lifestyle right away. With important improvements already completed, the home is ready to be enjoyed from day one.

Listed by Andie Fusco of Four Seasons Sotheby's Int'l Realty

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

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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.

856 Matteson Road Bennington VT 05201

Bennington, VT856 Matteson Road

Price$579,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5085559

  • Residential Single Family
  • Full Bath 2
  • Address 856 Matteson Road
  • Bedrooms 3
  • Bathroom 2

Nestled on 5 private acres, this custom-built log home offers the perfect blend of rustic charm and refined comfort. Surrounded by beautifully curated gardens, mature apple trees, lilacs, maples, plum trees, oaks, and stone walls, the setting is both tranquil and picturesque-yet just minutes from town conveniences. There is even a targeting golf green! Inside, the home showcases a stunning great room anchored by an impressive floor-to-ceiling fireplace, with a loft above that overlooks the space and adds architectural interest. The thoughtfully designed layout includes three bedrooms, highlighted by an incredibly spacious primary suite featuring a walk-in closet and a luxurious en suite bath with soaking tub and double vanities. The main level also offers two additional bedrooms, a full bath, and convenient first-floor laundry. A bright breakfast nook provides the perfect spot to start your day, while the back deck overlooks the lush gardens, creating an ideal setting for outdoor entertaining or quiet relaxation. The inviting front sitting porch, complete with a charming fish pond, enhances the home's peaceful appeal. Additional features include an attached oversized two-car garage, a home office, large workshop and sweeping mountain views that complete this exceptional property. A rare opportunity to enjoy privacy, natural beauty, and timeless craftsmanship in one remarkable setting.

Listed by Faith Rhodes of Maple Leaf Real Estate

{$office->Name}

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.

30 Upper Woods and Water Road Winhall VT 05340

Winhall, VT30 Upper Woods and Water Road

Price$575,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5078937

  • Residential Single Family
  • Full Bath 1
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,400

Perched to capture breathtaking long-range views, this striking ski home offers an unforgettable vantage point of Magic Mountain and Stratton, with Bromley visible to the northwest-a daily reminder that some of Southern Vermont's best skiing and outdoor adventure are just minutes away. With its cool, modern vibe and classic alpine character, the home perfectly blends style, comfort, and mountain living. The main living area is designed to showcase the spectacular scenery, with large windows that frame the surrounding mountains and fill the space with natural light. A wood-burning fireplace anchors the living room, creating the perfect spot to gather after a day on the slopes. Clean architectural lines, warm materials, and thoughtful updates give the home a contemporary yet welcoming feel throughout. Several upgrades and renovations provide comfort and efficiency for years to come. The property also includes a carport, providing convenient covered parking so you won't have to clear snow off your car after a Vermont snowfall, along with space for skis and all the gear that comes with an active mountain lifestyle. Perfectly located just minutes from Bromley Mountain and a short drive to Stratton Resort, this home is ideally positioned for year-round recreation-from skiing and snowboarding in winter to hiking, biking, and golf in the warmer months. An added benefit of this property, if you opt to join, is that a Bromley Bond is available, providing driveway plowing, and garbage pickup services. Whether you are seeking a full-time residence or a retreat, this unique mountain home offers style, views, and an unbeatable Southern Vermont location. Closing to occur on or after June 15. The buyer may elect to close earlier and allow the seller to rent the property back until June 15. This property will transfer unfurnished.

Listed by Carrie Mathews of Winhall Real Estate

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

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Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

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

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

126 Simeon Dean Road Shaftsbury VT 05262

Shaftsbury, VT126 Simeon Dean Road

Price$574,900The price has recently decreased

Est. Mortgage: $/month

MLS Number 5067149

  • Residential Single Family
  • Full Bath 2
  • Address 126 Simeon Dean Road
  • Bedrooms 4
  • Bathroom 3

Horse enthusiasts take notice! Barn Recently renovated w New Electric, 3@12x12 stalls, new Loft & Heated Tack Rm added, or use as desired, Hobby Shop, Antiques, Storage. Wonderful Newly Fenced Pasture & Paddocks & Fencing around house for children or pets. Charming audible Paran Creek from the porch w/nearby adjoining access to serene 6acre Spring Fed Pond. Total of 17.47 acres for your complete enjoyment. This is a vintage 1800's farmhouse w/an old grist mill foundation still evident along the brook w/this historic property! Covered Porch & Patio is perfect for relaxing rocking, while being soothed by the soft sounds of the brook. Renovated in 2020 including Elec, Heating & Lighting updates. Outdoors there are berries, perennials, mature apple trees & volleyball court! Presently used as a second story apartment/two family, or can easily revert back to one larger single family, additionally can be as In-Law family living w/second kitchen. Home presently occupied by Owner & Tenant, photos prior to owner occupancy. Currently home business. 15 mins to nearby Bennington or 25 mins to Manchester for shopping & restaurants, Rt 7 north/south State access. Lake Shaftsbury State Park nearby. Seller can be Ready! Tractor negotiable. Please call,text or email for latest on occupancy.

Listed by Denise Byers of Green Mountain Premiere Properties

{$office->Name}

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.

971 South Stream Road Bennington VT 05201

Bennington, VT971 South Stream Road

Price$550,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5088350

  • Residential Single Family
  • Full Bath 2
  • Village Bennington
  • Bedrooms 5
  • Bathroom 2

Have you been searching for the Vermont farmhouse that truly feels like home? The one with the land, the barns, the mountain views, the wraparound driveway, the screened in porch, and the beautiful front porch where you can sit and enjoy quiet mornings and peaceful evenings? This is that home. Situated on over 17 acres, this property offers not one but two barns, established fenced pastures, and the kind of setting that feels like a Vermont dream. Listen to the breeze move through the grass, watch the leaves change color in the fall, and enjoy the privacy and beauty that surround you. Inside, you'll find five bedrooms and two full bathrooms, with space that invites family dinners, holiday gatherings, and everyday moments that make a house feel special. The usable basement offers excellent storage, workshop potential, tool space, or room for tack and farm equipment. Whether you have horses, farm animals, or simply want the charm and comfort of country living, this property offers the Vermont lifestyle so many people dream about. This is more than a house it's the feeling of finally coming home.

Listed by Brooke Thomson Drew of Mahar McCarthy 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.

136 Fox Run Road Arlington VT 05250

Arlington, VT136 Fox Run Road

Price$550,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5089945

  • Residential Single Family
  • Full Bath 1
  • Address 136 Fox Run Road
  • Bedrooms 2
  • Bathroom 2

Perched above the Battenkill River Valley and surrounded by mountain views this two story Vermont Gem is waiting for you. The perfect size two bedrooms, two bath home offers maple hardwood flooring, oversized windows and soaring mountain views. Lovely perennial gardens, flowering apple trees and large meadows grace the 3.90 acre property. This thoughtfully constructed home was built in 2000 with meticulous details, including; crown molding, built-in bookshelves, solid wood pocket doors and large closets are just a snipit of the construction. The soapstone wood stove and attached garage offer convenience and practical living. Don't miss the large, heated, unfinished basement with high ceilings an additional 700 sqft. The front porch and back patio offer a nice mix of outside living. The second meadow parcel would make a fabulous garden or horse pasture. Fishing, Swimming and floating on the Battenkill River, The picturesque West Arlington Covered Bridge and Wayside Country Store are just down the way. Manchester and Ski mountains are a short drive. Five Ski Mountains with in an hour drive. Come live your Vermont Dream and make this property your own. Showings by appointment. Call today! Don't let this one get away. Truly a special property. Open House Saturday, May 23 1-3

Listed by Margretta Fischer 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.

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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 9:53 PM EDT

 

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