Our mobile site is optimized for smaller screens.

TRY IT NO THANKS

and narrow your search. If you have fewer than 200 results, you can save your search.

308
results
Narrow Your SearchRefine Search

Windham County

r=131-140
3996 Route 30 Jamaica VT 05343

Jamaica, VT3996 Route 30

Price$539,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5076624

  • Residential Single Family
  • Full Bath 2
  • Address 3996 Route 30
  • Bedrooms 4
  • Bathroom 3

Village charm meets mountain lifestyle in this beautifully updated home in the heart of Jamaica. Set above the road for added privacy, the property captures lovely winter views of the surrounding mountains and river while remaining just a short stroll to local shops and village conveniences. Inside, you'll find generous living space with warm wood floors and a flowing, open layout designed for gathering. The inviting great room features a wood-burning stove and sliders that lead to a private deck and sunny yard-perfect for summer barbecues or peaceful mornings with coffee. The renovated kitchen offers an island, large pantry, and easy access to a bright dining area lined with windows. Minimum of 24 hours notice for showings during the month of March. Upstairs are four comfortable bedrooms, including a spacious primary suite with its own bath. With three bathrooms, a dedicated laundry area, office, mudroom, and abundant storage throughout, this home blends classic character with everyday functionality. Adventure is always within reach-just minutes to Stratton Mountain Resort, Jamaica State Park, and Pikes Falls-with hiking, biking, skiing, and kayaking right at your fingertips. A sunny lot with garden potential and storage for bikes and kayaks complete the picture. Extensive updates over the past three years-including new windows, siding, flooring, a new furnace, and much more-offer peace of mind and modern efficiency while preserving the home's timeless appeal. A true four-season retreat at an exceptional value-come experience the best of Vermont living.

Listed by Carrie Mathews of Winhall 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:

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.

1041 Church Hollow Road Marlboro VT 05301

Marlboro, VT1041 Church Hollow Road

Price$538,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5092339

  • Residential Single Family
  • Full Bath 2
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,567

Country quiet and tranquility! Sun dappled trees and seventeen woodland acres surround this comfortable seven room, four bedroom, two and half bath house and two car garage. A peaceful setting where views from the deck, porch and every window take in the richness of nature and give a feeling of solitude. Built in 1987, this 2567 SF home has been much loved and well cared for. Designed for easy liveablity, a lifestyle choice for two level living now or one level living when desired. An inviting open floor plan with an 18'x 11' dining room, a 25' x 15' living room w/cathedral ceiling, a brick hearth & wood stove, a 12' x 11' kitchen that shares the brick hearth wall, all have maple wood floors. A 6' x 11' pantry with laundry. The 12' x 14' first floor primary bedroom has double closets. The full bathroom has both a separate walk in shower and an adjacent tub with a shower. A 13' x 14' bedroom/office and a half bath complete this level. For your creative spirit, upstairs is a 24' x 13' loft space now a quilting studio. There is a 22' x 14' bedroom with a skylight, large windows and two walk in closets. A cozy 12' x 13' bedroom/home office with a skylight. A walk out basement offers ample space for a home workshop. The attached 25' x 25' two car garage has storage space above. A pergola covered 20' x 10' deck is located off the living room. The 6' x 25' side porch is perfect for morning coffee/tea. The 17.8 surveyed acres has 1282 feet of frontage on a town maintained gravel road. When the world invites you away, choices abound in every direction! There is music, restaurants, theater, bookstores, artisan/collectible shops and places for ice cream. Recreational sports of all kinds are not far away. The new Amtrak train station in Brattleboro will bring ways to have new travel adventures. Exit 2 for Interstate 91 is 11 miles away. The town of Marlboro is in the process of completing a townwide property reassessment. Showings begin on Saturday June 6th by appointment.

Listed by Kathy Dowd of Bellville 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: 6.52% 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.

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

{$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.

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

{$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.

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

{$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.

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

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: 6.52% 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

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.

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

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: 6.52% 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

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.

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

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.

Broker Reciprocity 

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 15, 2026 7:37 AM UTC

 

You Can Edit This Text

Custom Search

Luxury Home Guide

Shelburne Luxury Homes