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Windham County

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147 Gilbert Road Marlboro VT 05344

Marlboro, VT147 Gilbert Road

Price$525,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5089735

  • Residential Single Family
  • Full Bath 1
  • Address 147 Gilbert Road
  • Bedrooms 3
  • Bathroom 1

This sweet home is nestled in the serene, and quiet location of Gilbert Rd, a dead end, located on the edge of Newfane but in the quaint town of Marlboro, VT. It has been completely renovated within the past few years by a local high-end builder with an eye for energy efficiency. His workmanship is evident in the renovation. The result: this pristine home gleams with its fresh and inviting design. New heat pumps, insulation and septic provide a clean slate for any homebuyer. All brand-new furnishings for an easy transition. An attractive retaining wall was recently built with field stones and steps for easy access. Many plantings have been added for a colorful summer ahead. A wood stove was installed in the sunroom for year-round comfort. A babbling brook runs along one side of the property, leading to the nearby West River. The home is also an easy commute to Brattleboro for unique eateries, farmers markets, gallery walks and so much more. If you are a skier, Mount Snow is nearby! Hikers will have the opportunity to explore the almost 50 acres this property has to offer. Plenty of open space is available for vegetable gardening, as well. This truly is a lovely home waiting for its next chapter to unfold. (Deed says 52.5 plus or minus and tax bill says 49 acres.) This home is coming mostly furnished making it completely move in ready.

Listed by Monica Sumner of BHG Masiello Brattleboro

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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: 6.52% last updated on 2026-06-11

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

5735 VT Route 11 Londonderry VT 05148

Londonderry, VT5735 VT Route 11

Price$525,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5091606

  • Residential Single Family
  • Full Bath 2
  • Address 5735 VT Route 11
  • Bedrooms 4
  • Bathroom 4

What do you get when two pioneers buy a beautiful colonial farmstead with the intention of sticking around quite a while, rehabilitate it for their long-term use, and then find out work will require them to relocate? You get this gorgeously renovated 4-bath-4-bed 1890 construction on over 2.5 lovely acres back on the market! Historical authenticity has not been sacrificed in their successful pursuit of modern comfort: the tasteful remodeling of the kitchen, bathrooms, floors, ceilings, and more won't distract from your delight in the rustic touches left intact or even improved upon, like the specially-selected Glenwood Modern F Cookstove. Luxuriate in central AC, a Vermont rarity, when you come in from your work in the expansive 2-floor garage/barn, chicken coop, or on the grounds graced by a lovingly cared for orchard beside a scenic private pond. Did we mention the orchard? Apples, peaches, pears and cherries dot the landscape, an arborist's dream, with gorgeous mountain views in the distance! Nestled in the desirable town of Londonderry, you have access to year-round amenities at a level not found in every ski town: it's home to Magic Mountain, and a short drive away from Bromley, Stratton, and Okemo. In the warmer months, enjoy gorgeous 102-acre Lowell Lake, its state park and its islands just minutes away! While newly-planted arbor vitae promise to shoot up quickly and reduce the highway noise, the house sits comfortably above Vermont Route 11, a road offering pleasant drives between ski towns. Once you're inside or in your backyard, you may be surprised how quickly you forget about the world going by and remember to be glad you bought this diamond-out-of-the-rough. Sold largely furnished! Inquire today while it's still available!

Listed by Zachary Zupan of EXP 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: 6.52% last updated on 2026-06-11

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

25-27 Gingko Lane Brattleboro VT 05301

Brattleboro, VT25-27 Gingko Lane

Price$525,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5091641

  • Residential Single Family
  • Full Bath 2
  • Address 25-27 Gingko Lane
  • Bedrooms 3
  • Bathroom 2

Welcome to an amazing, unique opportunity on Gingko Lane in a very special location. Located on a quiet side street in this beloved neighborhood, you are in close proximity to the Retreat trails, which offer extensive hiking, and close to our vibrant downtown, a short walk away. The adorable 1,600-square-foot home has 3 bedrooms and 2 baths. The light-filled, open-concept kitchen/dining area is inviting and spacious. Upstairs needs finishing, but there are vaulted ceilings and an abundance of light from the many skylights. Pretty stone paths, widespread gardens, open decks, and a level, private sunny lawn. Above the two-car garage are two rental units-one occupied and one vacant-offering immediate income, strong potential for investors, and appreciation for homeowners. One unit is a two-bedroom, one-bath, and the other is a one-bedroom, one-bath. The home needs some finishing work, but this is an unbeatable opportunity, and your work will be well worth it.

Listed by Kristen Ziter Taylor and Angela Sherman of Brattleboro Area Realty

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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: 6.52% last updated on 2026-06-11

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

7 High Top Road Wilmington VT 05363

Wilmington, VT7 High Top Road, Unit B117

Price$525,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5092082

  • Residential Single Family
  • Full Bath 2
  • Address 7 High Top Road
  • Bedrooms 3
  • Bathroom 2

Section B. Top of the Hill, end of the road, this home is meticulously kept and updated, with lots of attention to detail. Start living the dream you imagine! A classic chalet design with mudroom entry, full bath and bedroom, and open concept living, dining and kitchen on the main level, with a wraparound deck. Upstairs has two bedrooms and a second full bath. The double lot offers privacy and options for a garage. Nice, landscaped level lot with a shed and woodbin, firepit and plenty of parking. Enjoy all the amenities Chimney Hill offers including the exclusive members only clubhouse, located at 2,000' in elevation, it's the perfect spot to enjoy year-round featuring indoor and outdoor heated pools, a brand new hot tub, fitness room, arcade, playroom, lounge, fully-equipped kitchen, playground, community room, table tennis, pickleball, ice skating, hiking, biking and snowmobiling on the 1,200 acre resort campus nestled between the Green Mt National Forest and the town of Wilmington VT. Minutes from world class skiing and shredding at either Vail's Mt Snow or the private Hermitage Club. Discover Southern VT and enjoy outdoor and indoor music, festivals, unique shopping and dining, antiques, flea markets, golf, boating, paddleboarding, and so much more! Owner's list of features and improvements: Two Lots, B117, B118 for privacy, Two Split Units for AC/Heat, Replaced all Electric Baseboard Heating Units, Gasoline powered generator hardwired into the electric panel, New Electric Panel, Hardwired Ring Outdoor Cameras, Vapor Barrier Throughout Crawl Space, Flooring throughout the whole house, Window treatments, Furniture, Bedding, Kitchen Appliances, HWH on GMP Rental Program $10 mo., Washer & Dryer, Four Flatscreen TV's, Safe in MBR, Kitchen Countertops, Both Bathroom Fixtures, Countertops & Toilets, Ceiling Fans & Ceiling Lights, Safety Railings & Wiring on Stairs & Loft, Storage/Woodshed Outside, Firepit

Listed by Sigrid Pickering of Chimney Hill 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: 6.52% last updated on 2026-06-11

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

27 Ray Hill Road Wilmington VT 05363

Wilmington, VT27 Ray Hill Road

Price$510,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5083391

  • Residential Single Family
  • Full Bath 2
  • Address 27 Ray Hill Road
  • Bedrooms 3
  • Bathroom 3

Located in a desirable setting that offers both privacy and the convenience of walking to the quaint village of downtown Wilmington, this spacious country home is full of potential. The home features a large, light-filled kitchen with plenty of space for cooking and gathering. The original post-and-beam barn, which was moved to the property, has been converted into a generous living and dining area, adding warmth and character. There are two bedrooms on the first floor, each with its own private bathroom. Additional space includes another bedroom, a bonus area, and an office, providing flexibility for a variety of uses. Outside, you'll find established perennial gardens and a sunny meadow, perfect for gardening or relaxing. The property also borders a stream, with the option to create a path for access. The home does need updating, but with renovations, it offers a great opportunity to create something special. If you're looking for country living with convenience, this property is for you.

Listed by Monica Sumner of BHG Masiello Brattleboro

{$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: 6.52% last updated on 2026-06-11

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

829 Pennel Hill Road Halifax VT 05358

Halifax, VT829 Pennel Hill Road

Price$499,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5042081

  • Residential Single Family
  • Full Bath 1
  • Address 829 Pennel Hill Road
  • Bedrooms 3
  • Bathroom 3

Spacious cabin set on 16.4 acres with stream and pond. Open main living area features hardwood floors, vaulted ceilings with skylights, exposed beams, and an efficient wood stove. Updated kitchen includes stainless steel appliances and breakfast bar seating. Main level bedroom with shared en suite bathroom featuring claw foot tub and walk-in shower. Spiral staircase leads to primary suite with three-quarter bath. Lower level features an additional bedroom and cozy den/media room. Lower level includes garage with workbench, three-quarter bath, and new washer/dryer. Enjoy space for work or pleasure for a small car, recreational vehicles, snowmobiles, or lawn equipment. Recent improvements include fresh paint inside and out, generator, new decking with additional kitchen deck for outdoor dining, regraded driveway with expanded parking, and woodshed conveniently just off the front door. Idyllic location just 19 miles to Mount Snow ski resort and nine miles to Lake Whitingham's boating and recreation. Surrounded by nature with easy access to scenic hiking trails, premier fishing spots, and charming New England village shops. Perfect year-round retreat or weekend getaway.

Listed by Megan Quinn of Southern Vermont Realty Group

{$office->Name}

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

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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: 6.52% last updated on 2026-06-11

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

41 Chapin Street Brattleboro VT 05301

Brattleboro, VT41 Chapin Street

Price$499,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5087925

  • Residential Single Family
  • Full Bath 2
  • Address 41 Chapin Street
  • Bedrooms 4
  • Bathroom 3

Beautifully maintained, 1880s, in-town Victorian blends timeless elegance with modern comfort. The large, light-filled kitchen combines with an open, cathedral ceiling dining area inviting the gathering of family and friends. The renovated kitchen has granite, stainless steel appliances, and laundry area. Soaring, 9 ft ceilings create light-filled rooms. Elegance of timeless design and detailed wood trimmed finishes are throughout with crafted moldings framing arched and stain glass windows, custom fireplace mantles and functionally flexible built-ins. Enjoy the old-world charm of two covered porches. The expansive first floor has lovely potential for those wanting first floor accommodations. An ornately crafted staircase rises gracefully to the second floor with four bedrooms, two full baths and the continuation of flooding sunlight. The outdoors offers gorgeous stonework, lush perennial plantings and a magical patio. So close to downtown's Brattleboro Museum, Art Center, Galleries, Cafes, and more! Convenient to ski mountains and ready access to Boston and NY City. Visit this beloved, period home to experience a world of gentle elegance.

Listed by Kristen Ziter Taylor of Brattleboro Area Realty

{$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: 6.52% last updated on 2026-06-11

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

142 Dover Road Newfane VT 05362

Newfane, VT142 Dover Road

Price$499,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 5092305

  • Residential Single Family
  • Full Bath 1
  • Address 142 Dover Road
  • Village Williamsville
  • Bedrooms 4

Two houses for the price of one! Set on five acres along the beautiful Rock River in the heart of Williamsville, Vermont, this remodeled and tastefully furnished twelve-room farmhouse offers the perfect blend of classic New England charm and modern comfort. The spacious main home features four inviting bedrooms, generous living and entertaining spaces, and thoughtfully updated interiors throughout, combining warmth, character, and contemporary convenience. New windows frame peaceful views of the surrounding countryside and riverfront, while the expansive property provides endless opportunities to relax or explore nature. Whether enjoying quiet mornings on the patio by the water, hosting family and friends, or working remotely in a serene setting, this exceptional property-twenty minutes from Mt. Snow and fifteen minutes from bustling Brattleboro-offers a true Vermont lifestyle. Adding to its appeal is a separate completely renovated and fully furnished cottage - ideal for guests, extended family, rental income, or a private home office or studio. With its turnkey condition, stunning natural setting, and versatile living spaces, this rare Rock River property is a perfect year-round residence, vacation retreat, or investment opportunity. All you need are your swimsuit and skis to feel at home at this true slice of paradise.

Listed by Kassie Rubico of Berkley & Veller Greenwood Country

{$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: 6.52% last updated on 2026-06-11

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

522 Vermont Route 100 Wardsboro VT 05355

Wardsboro, VT522 Vermont Route 100

Price$499,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5093027

  • Residential Single Family
  • Full Bath 3
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,665

Dating to the 1830s and thoughtfully renovated through the 1990s and early 2000s, this Vermont homestead blends historic character with the comforts of modern living. Set on 12 mostly open, level acres surrounded by mountains, it offers the kind of setting people dream about but rarely find. Start your morning with coffee overlooking the meadow as mist rises from the fields and the sound of the rushing brook across the road fills the air. Just steps away, enjoy your own frontage on Wardsboro Brook, where you can create a private swimming hole, gather around a campfire under the stars, or simply relax and listen to the water flow by. The land invites endless possibilities. Picture horses grazing in the pasture, chickens in the barn, vegetable gardens and fruit trees, or create winding paths through wildflowers in the meadow. Old stone walls trace portions of the property's boundaries, while mature apple and pear trees provide seasonal harvests. The property includes a spacious 3-bedroom main residence with both formal and informal living areas, offering flexibility for entertaining or quiet evenings at home. An attached 2-bedroom guest apartment provides space for visitors, extended occupancy, or a home office setup. Between the house and barn, a fenced outdoor area offers a convenient space for recreation, pets, gardening, or outdoor gatherings. The circa-1942 barn stands ready for animals, equipment, hobbies, storage, or agricultural pursuits, while the attached 2-car garage adds everyday convenience. Located just minutes from Mount Snow and Stratton Resort, and with convenient access to the village center of Wardsboro, this property combines the peace and beauty of country living with easy access to recreation, dining, and community amenities.Come experience the sights, sounds, and possibilities of a Vermont property where history, nature, and lifestyle come together.

Listed by Lavinia Lee Brown 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: 6.52% last updated on 2026-06-11

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

313 South Pine Banks Road Putney VT 05346

Putney, VT313 South Pine Banks Road

Price$495,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5081236

  • Residential Single Family
  • Full Bath 2
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,536

Tucked into the woods of southern Vermont's most vibrant and artistic village, this thoughtfully updated 25-year-young home offers the perfect blend of modern ease and tranquil privacy amidst natural serenity. Indulge in the pleasures of the region that nourish body and soul - hiking, skiing, dining, local theater and music, and crafts - without the preoccupations and burdens of home renovations hanging over you. Major house upgrades over the past four years include a new roof, hot water tank, mini-split, garage door, side deck, front stairs, septic line, and water softener. Mature gardens and occasional visits from deer lend an added layer of beauty and calm. Inside, an open-concept layout seamlessly connects the kitchen, dining, and living spaces, all bathed in natural light. Two main-floor bedrooms and a private lower-level room make hosting and entertaining a breeze. Recent enhancements elevate daily living, including a sauna, a high-end Piazzetta pellet stove, honeycomb blinds, a custom closet system, and a full-house generator.An attached garage ensures winter convenience, while a detached two-car garage with an expansive unfinished studio loft offers a blank canvas for creatives and hobbyists, or some extra storage space. Peaceful, private, and move-in ready-this is Putney living at its finest.

Listed by Thom Dahlin of Berkley & Veller Greenwood Country

{$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: 6.52% last updated on 2026-06-11

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 17, 2026 9:23 AM UTC

 

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