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Windsor County

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111 East Gilson Avenue Hartford VT 05059

Hartford, VT111 East Gilson Avenue

Price$499,500The price has recently decreased

Est. Mortgage: $/month

MLS Number 5086145

  • Residential Single Family
  • Full Bath 1
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,827

This is the type of property that doesn't come around very often! It is set on 2.5 private acres at the end of the road, abutting Vermont State Forest land. That said, it has terrific walkability to stores, Simon Pearce, the elementary school, Lake Pinneo, nearby hiking trails and Quechee Gorge. It's an easy drive to skiing, shopping in West Lebanon and hospitals. The land features level sunny spaces for gardening and gatherings with friends and family, and slopes into woods leading to State Land. This classic New Englander retains the charm you expect in Vermont. The spacious country kitchen has plenty of workspace and room for extra chefs. Original pine plank floors throughout lend warmth and character. The main level features a generous living room suitable for gatherings, central dining room and a three-quarter bathroom. There are also two enclosed porches that invite you to relax with your morning coffee or after a day of work and enjoy the view. The second level features the primary bedroom with full bath and laundry combined, 2 additional bedrooms and a bonus room perfect for a den, office or quiet reading library. The zoning is R3 and it has possible subdivision potential; the town zoning office can provide the necessary information and procedures. This home is ready for its new chapter, offering many years of comfort and enjoyment to the next owners. Sellers are offering $10,000 concession for barn removal or other need. Quote from KJL roofing of $11,750 to remove.

Listed by Mary Paino of Coldwell Banker LIFESTYLES - Quechee

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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.

115 Horseshoe Drive West Windsor VT 05037

West Windsor, VT115 Horseshoe Drive

Price$499,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5086481

  • Residential Single Family
  • Full Bath 1
  • Address 115 Horseshoe Drive
  • Bedrooms 5
  • Bathroom 3

Tucked away at the end of a quiet dirt road, this well-maintained and inviting home offers the perfect blend of privacy and comfort. Set on a secluded lot, the property provides ample space to relax and unwind, featuring two bright and versatile four-season porches ideal for enjoying the surrounding natural beauty year-round. Inside, a spacious living room serves as the heart of the home, highlighted by a stunning stone fireplace and expansive windows that frame picturesque views of a serene, spring-fed pond. The layout is designed for both everyday living and entertaining, with plenty of room to spread out. A standout feature is the bonus basement in-law apartment, complete with its own private entrance-perfect for extended family, guests, or potential rental income. The property directly abuts conservation land, ensuring lasting privacy and access to unspoiled nature, while nearby recreational trails offer endless opportunities for outdoor adventure. This is a rare opportunity to own a peaceful retreat without sacrificing convenience. Close to the Vast Trail. New 5 bedroom septic in 2018. Live upstairs and allow the tenants to pay your taxes.

Listed by Katie Ladue Gilbert and Allison Griep of BHHS Verani Upper Valley

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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.

12 Vermont Drive Hartford VT 05001

Hartford, VT12 Vermont Drive

Price$499,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 5089563

  • Residential Single Family
  • Full Bath 2
  • Address 12 Vermont Drive
  • Bedrooms 3
  • Bathroom 2

Tucked away on a quiet cul-de-sac in Hartford, this lovely ranch-style home offers easy single level living with an inviting open-concept layout, an oversized front porch, and spacious back deck perfect for relaxing or entertaining. The private backyard provides a peaceful setting with room for gardening, play, or enjoying Vermont evenings surrounded by nature. Inside, the generous primary suite and full finished basement offer flexible space for guests, recreation, or a home office. Conveniently located just minutes from shopping, dining, schools, and the many amenities of the greatly desired Upper Valley. This home blends comfort, privacy, and accessibility. House showings may only occur after 4:30p M-F and over weekends.

Listed by Jeff Fogg of Black House 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.

33 Merritt Road Hartland VT 05048

Hartland, VT33 Merritt Road

Price$499,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5092955

  • Residential Single Family
  • Full Bath 1
  • Address 33 Merritt Road
  • Bedrooms 3
  • Bathroom 2

Open House 6/6 2-4 Offered for the very 1st time since it was built in 1973, this enchanting, cherished woodland retreat captures the very essence of VT living. Nestled on 7.6 private acres among the rolling meadows and forests of Hartland, 33 Merritt Road offers a rare opportunity to own a peaceful oasis with exceptional access to the Upper Valley's most desirable destinations. This charming Gambrel-style home features approximately 1,800 square feet of thoughtfully designed living space across two stories, with a walk-out basement. With three bedrooms, a one-car garage, and a warm, inviting atmosphere, it feels instantly like home. Large windows frame the surrounding natural beauty while the home's setting offers privacy, tranquility, and a deep connection to the landscape. The comforting warmth of the woodstove creates the perfect Vermont ambiance on snowy winter evenings, making the home feel especially cozy throughout the colder months. Outside, the expansive deck becomes an extension of the living space and a true sanctuary in the warmer months. Hummingbirds gather among vibrant phlox, lilac, bee balm, and beautifully established perennial gardens, creating a colorful and peaceful backdrop for morning coffee, outdoor dining, or quiet evenings under the stars. Located just minutes from I-91 and directly on the VAST snowmobile trail system, this property offers outstanding year-round recreation and convenience. Commuters will appreciate easy access to DHMC, Dartmouth, Vermont Law School, and nearby NH. Hartland's school choice program continues to attract families seeking flexibility and educational opportunity. Adventure and culture are all within reach, with RT 4 providing easy access to Killington Resort, the timeless village of Woodstock, Quechee, and shopping and dining. Whether you are searching for full-time home, a getaway, or A peaceful Homestead, surrounded by nature, this property offers privacy, convenience, and charm in a beautiful natural setting.

Listed by Sandy Reavill of Willow Brook 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.

990 Main Street Cavendish VT 05153

Cavendish, VT990 Main Street

Price$495,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5090469

  • Residential Single Family
  • Full Bath 1
  • Address 990 Main Street
  • Village Proctorsville
  • Bedrooms 4

If you're looking for the ultime village ski house look no more! This four bedroom three and a half bath TURN KEY home is nestled in the village of Proctorsville. Home to Singletons Store, Outer Limits Brewery, Murdoch's On The Green and much more walking distance away. Step into this lovely well appointed home and you'll feel right at home. The kitchen boasts granite counters with a large breakfast bar. Oak cabinetry, mostly stainless steel appliances, tile backsplash and under counter lighting. You'll love the open concept of the kitchen and dining room, with a granite two sided fireplace. Mozie on into the large living room with space for the whole crew and cozy up to the other side of the fireplace. The first floor is completed with an en-suite bedroom with a beautiful view of Hawks Mountain, the bathroom is finished with a tiled shower and a natural wood vanity. Rounding off the main floor with a half bath laundry room combo and a convenient corner nook for gear storage. Upstairs you find another en-suite bedroom with double sink, natural wood vanity and tiled shower. The two other large bedrooms share a full bath. One bedroom with a balcony overlooking Hawks Mountain State Forest which is a healthy walk away for recreating. Now down the the lower level where the fun begins. Pool table, foosball or a game of cards, pick your favorite. This Ultimate Village Ski House is priced to sell! Come take a look today!

Listed by Frank Provance of Diamond Realty

{$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.

2818 Route 65 Brookfield VT 05036

Brookfield, VT2818 Route 65

Price$495,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5091505

  • Residential Single Family
  • Full Bath 2
  • Address 2818 Route 65
  • Bedrooms 5
  • Bathroom 3

Tucked away on 10+/- enchanting acres in beautiful Brookfield, this special property is filled with warmth, charm, and the kind of peaceful beauty that makes you want to stay forever. Wander along the magical forest trail, cross the path bridge, and discover your own frontage on North Pond, the perfect spot for paddling, quiet reflection, or simply soaking in nature's beauty. The main home welcomes you with inviting outdoor spaces designed for every season, from the beautifully landscaped stone patio with fire pit to the expansive covered front porch made for relaxing summer evenings. Step inside through the side entry and deck into a spacious mudroom area with overhead storage, then continue into the sunny country kitchen featuring a cozy breakfast nook and abundant cabinetry. The heart of the home is the open living and dining area centered around a charming wood stove, creating a warm and inviting gathering space. Just off the dining room, enjoy easy access to the covered porch for seamless indoor-outdoor living. The first floor also offers a spacious primary bedroom and full bath, while upstairs you'll find two generously sized bedrooms and a half bath. Adding even more versatility and value is the beautifully renovated second dwelling connected by the front deck and steps. With a two-car garage below, this lovely space offers an open-concept living, dining, and kitchen area, one bedroom and bath on the main level, and upstairs a large bedroom with French doors plus additional flexible space ideal for a home office, studio, or reading nook. Complete with its own heating system, electric service, and septic, this second home is perfect for guests, rental income, or multi-generational living. A truly exceptional property where comfort, nature, and opportunity come together in one unforgettable setting. Join us for an Open House on Saturday, May 30th from 11:00 AM to 1:00 PM.

Listed by Lucy Ferrada of Heney Realtors - Element Real Estate (Montpelier)

{$office->Name}

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.

105 Craigue Hill Springfield VT 05156

Springfield, VT105 Craigue Hill

Price$490,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5085886

  • Residential Single Family
  • Full Bath 1
  • Address 105 Craigue Hill
  • Bedrooms 3
  • Bathroom 2

Motivated Seller! Price Adjustment on this17 acre, property with a pond and 2 houses. Close to schools, shopping, medical services and recreation, this property offers privacy, views and a pond. This property also enjoys a beautiful guest house for visitors or a long-term rental. The main house is a traditional cape style with an abundance of porches for viewing wildlife. The entrance foyer and sitting area leads to the living room and the large dining room featuring built-ins. The oversized kitchen provides space for dining or perhaps an island, as well as family room space in front of the wood stove. The primary bedroom enjoys a private sitting area, office or perhaps your yoga space. With 2 more bedroom and 2 baths it is truly a delight. The detached garage hosts a studio/office space overhead. The second living space is located over the 2-car garage and is stunning with the interior done in wood, stonework, tile and more. The open concept living, dining and kitchen features plenty of cabinets and storage. The generous bedroom and bathroom are roomy and comfortable. The sunporch has room for the hot tub and offers views of the pond and mountains. The property has fruit trees, stone walls and some trails with land to develop more for walking or snowshoeing.

Listed by Carol Cole of BHG Masiello Brattleboro

{$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.

1254 US Route 5 Weathersfield VT 05156

Weathersfield, VT1254 US Route 5

Price$485,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5070225

  • Residential Single Family
  • Full Bath 1
  • Address 1254 US Route 5
  • Bedrooms 8
  • Bathroom 1

Welcome to the former Danforth Inn! Take a trip back in time to 1780 as you look at this extremely original old building that was built in Weathersfield Bow in 1780 by Gideon Lyman. In 1789 Joseph Danforth moved to the Bow and he leased and then bought the Inn, changing the name to the Danforth Inn. This property will need some love, but it has never been spoiled in its originality, and it's just waiting for someone to bring it back to its former glory days! And the barns? They are beautiful! The really nice full basement under the large barn has very pretty and straight stone foundation and the cow stanchions are still in place! The backyard is private with lots of space for family fun. The 39 acres goes way back up behind the house with an old town road (unmaintained and unused) bordering the property line for easy access. Great for riding horses or for any other outdoor recreation you desire! The "Danforth Inn" would make a beautiful country bed and breakfast, a produce or farm stand, or whatever your dreams might be. Or make it a fabulous home where you can feel like you are reliving the past of 200 plus years ago! This is a rare opportunity for you to own a genuine piece of Vermont history!

Listed by Glenn Olney of Barrett and Valley Associates Inc.

{$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.

691 Cemetery Street Brookfield VT 05036

Brookfield, VT691 Cemetery Street

Price$479,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5066548

  • Residential Single Family
  • Address 691 Cemetery Street
  • Bedrooms 1
  • Bathroom 1
  • Square Feet 816

Beautiful +53-acre property in Brookfield featuring a well-built, efficient off-grid home with rare fiber optic internet on site! There is grid power available at the road should you choose to bring it up the driveway. A four-bedroom septic is ready for your larger custom home should you choose to build one on the gorgeous building site that awaits. There is currently a two-car garage with gambrel living space above that would be a perfect efficiency apartment/guest suite or writer's escape. The living room has a cozy Jotul woodstove and there is a propane furnace so you can head out for the winter without concern. Additionally, the land is in a well-established current use plan offering annual tax savings. Being off grid protects from grid failures or natural disasters with a quality seller-owned solar array powering a deep drilled well. There is also an automatic propane generator at the ready. The land is ~40% open with gentle slopes, ideal for pasture, trails, or gardening, and includes established blueberry, and raspberry bushes and apple and pear trees plus asparagus and grapes. Bring your vision for expansion or enjoy this peaceful, self-sufficient retreat-less than 3 hours from Boston and 5 from NYC. Perfect for outdoor lovers, gardeners, or those seeking privacy with easy accessibility.

Listed by Holly Hall and Franchesca Collins of Hall Collins Real Estate 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.

64 Maple Street Chester VT 05143

Chester, VT64 Maple Street

Price$479,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5087175

  • Residential Single Family
  • Full Bath 1
  • Address 64 Maple Street
  • Bedrooms 3
  • Bathroom 3

Located in the village of Chester, this 3-bedroom, 3-bath property offers a rare amount of space and flexibility for an in-town setting. You'll enter through the heated attached two-car garage into a layout that's both functional and easy to live in, with room to spread out when you need it and gather when you want to. The kitchen features warm wood cabinetry, a breakfast bar, and a flexible area that works just as well for casual dining as it does for a home office setup. The dining space flows easily into a sunken living room, where the pellet stove becomes a natural gathering spot. Two bedrooms on the main level, each with their own bath, make this a great fit for a variety of living situations. Upstairs, you'll find a spacious bedroom, a separate flex room currently used as a movie room, and an unfinished bonus area ready for whatever you have in mind. Storage is not an issue here, between the closets and full basement, there's plenty of space to keep things organized. The home is equipped with a new furnace and four heating zones, offering efficiency and control throughout. Outside, a wide back patio gives you a great place to relax, while the barn and oversized three-bay garage offer serious utility for storage, equipment, or hobbies. The detached garage is currently rented for $500 per month, and the tenant would be open to continuing that arrangement with the next owner. The property borders Lovers Lane Brook, adding to the natural setting and privacy, all just minutes to Chester's shops, dining, and village amenities. If you've been looking for an in-town property with more space and versatility than most, this one is worth a look. Furnishings are negotiable for anyone looking for a truly turn-key property!

Listed by Betsy Adamovich of Real Broker LLC

{$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 13, 2026 11:38 AM UTC

 

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