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Windham County

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11 Strawberry Hill Brattleboro VT 05301

Brattleboro, VT11 Strawberry Hill

Price$639,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 5082239

  • Residential Single Family
  • Full Bath 1
  • Address 11 Strawberry Hill
  • Bedrooms 4
  • Bathroom 3

Beautifully sited on 1.9 acres just off Greenhill Parkway, this tastefully modernized 1940s cape blends architectural pedigree with thoughtful, high end updates. Designed by noted architect James Britton of Greenfield, MA - a contemporary of Royal Barry Wills and long admired for his classic New England forms - the home retains its classic original character, while offering a fully refreshed interior. The 4 BR, 3 BA layout includes a full width living room with wood burning fireplace, a handsome dining room with built-in corner cabinets and a massive, x-pane window overlooking the backyard. The kitchen is a standout, featuring Crown Point beaded frame cabinetry, heated encaustic tile floors, Zellige tile walls, a Liebherr refrigerator, Miele propane cooktop, KitchenAid double ovens, and a custom Pella hydraulic lift awning window - ideal for outdoor entertaining. Rounding out the first floor is a beautifully executed mudroom/laundry created between the kitchen and attached 2 car garage, a private and comfortable den, a spacious formal entry hall, and updated powder room. All bathrooms have been fully renovated with Waterworks fixtures and Toto washlet toilets; two with custom tile showers, heated tile floors, and Visual Comfort lighting. A spacious suite above the garage offers flexibility for a primary bedroom or in law arrangement, offering new solid oak flooring, a walk-in closet, and a decadent bathroom with soaking tub and separate shower. The location is exceptional, being an easy walk to downtown and the park, and privately tucked into an unusually large lot; and with unique, direct access to over 9 miles of trails via a path along the lower edge of the property. A rare combination of history, craftsmanship, and modern comfort in one of Brattleboro's most desirable neighborhoods. The home also comes with original 1944 blueprints and historical materials from the Norton family; the property's first owners.

Listed by Dan Normandeau 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.

187 Poverty Row Whitingham VT 05361

Whitingham, VT187 Poverty Row

Price$629,900The price has recently decreased

Est. Mortgage: $/month

MLS Number 5093664

  • Residential Single Family
  • Full Bath 2
  • Address 187 Poverty Row
  • Bedrooms 3
  • Bathroom 2

Outstanding contemporary farmhouse set on 5.3 acres of private, level acres, offering the perfect blend of comfort, space, and functionality. This well-maintained home features an open-concept first floor with a spacious great room highlighted by a cathedral ceiling. The main level also includes one bedroom and full bath, along with a convenient mudroom and laundry room. The custom maple kitchen cabinets boast updated countertops, and the newer flooring runs throughout the first floor. The home's efficient Buderus boiler provides five heating zones for year-round comfort, with radiant heat running through the kitchen and bath for added comfort on those chilly mornings. The unfinished basement has separate rooms for potential finishing, along with a workspace for the handy or craftsperson. The oversized 30x30 two-car garage with loft provides exceptional storage space. A covered wraparound porch offers the perfect place to relax and enjoy the peaceful surroundings, and the open deck off the rear for sunny days to relax or entertain. Conveniently located near a local park with a ballfield and playground. We are just a short drive to wonderful Vermont skiing and many 4 season activities. Whitingham Dam is a quick drive for your boating pleasure. This is country living with easy access to community activities all on your own 5.3 acre parcel.

Listed by Pauline Green of Lamacchia Realty 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: 6.52% 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.

239 Valley View Road Dover VT 05356

Dover, VT239 Valley View Road

Price$625,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5078011

  • Residential Single Family
  • Full Bath 1
  • Address 239 Valley View Road
  • Bedrooms 4
  • Bathroom 2

This contemporary 3-bedroom plus loft, 2-bath home in Dover Hills offers both comfort and convenience. The property features a detached 2-car garage with overhead storage, an additional carport, and a wood shed. The recently remodeled kitchen boasts new cabinets, countertops, and appliances, complemented by wood floors throughout and new skylights that fill the space with natural light. A gas brick fireplace adds warmth to the living room, while the mudroom includes a built-in bench for added functionality. The lower level, with direct outdoor access, includes a family room, laundry area, and open space ready for your finishing touches. Located near VAST trails, this move-in-ready home is perfect for year-round living or a weekend ski retreat, offering easy access to Vermont's outdoor adventures in every season.

Listed by Jennifer Densmore of Deerfield Valley Real Estate

{$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.

15 Bills Road Stratton VT 05360

Stratton, VT15 Bills Road

Price$625,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5079418

  • Residential Single Family
  • Full Bath 2
  • Address 15 Bills Road
  • Bedrooms 4
  • Bathroom 3

This spacious four-bedroom, three-bath Cape-style home offers a wonderful Vermont retreat, ideally located just minutes from the Stratton Mountain Resort Sun Bowl and the scenic Grout Pond Recreation Area, and only about 10 minutes from Mount Snow Resort. With immediate access to nearby snowmobile trails, it's perfectly suited for year-round outdoor enthusiasts. Nicely landscaped yard with perennial gardens, 25x16 barn with electric, gardening shed, wood shed, playground structure, and a circular driveway. The main level features a thoughtfully updated layout, including a remodeled full bathroom, a comfortable bedroom, and an updated kitchen with stainless steel appliances that flow seamlessly into the dining area. A cozy den with a wood stove provides the perfect spot to relax after a day on the slopes, while the spacious living room offers additional gathering space for family and friends and sliders out to the back deck. Upstairs, you'll find the primary bedroom, a second guest bedroom, and another beautifully remodeled full bathroom, creating a comfortable and private upper-level retreat. The finished lower level adds exceptional versatility and potential for guest accommodations. It includes a family room with a Jotul wood stove, an additional bedroom, a ¾ bathroom, and a storage room that could easily serve as a sleeping space or office. A convenient kitchenette, utility and laundry room, and a mudroom with a separate entrance. With its prime location near skiing, hiking, snowmobiling, and year-round recreation, this home offers the perfect balance of comfort, convenience, and Vermont mountain lifestyle.

Listed by Jennifer Densmore of Deerfield Valley 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: 6.52% 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.

143 Hillwinds Road Brattleboro VT 05301

Brattleboro, VT143 Hillwinds Road

Price$625,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 5082786

  • Residential Single Family
  • Full Bath 1
  • Address 143 Hillwinds Road
  • Bedrooms 5
  • Bathroom 4

Welcome to Hillwinds and this lovely colonial. With 200 acres of conserved land and trails behind and a wonderful meadow view in the front, this house truly feels a part of the landscape. The main house has four bedrooms and two and a half baths and invites you to step right into your new life in this well cared for and lovingly maintained home. The gardens are in, the drive paved and the garden shed with power is standing ready. The sweet sun room is a nice addition to the living area, just off the kitchen/family room so a great place to expand when entertaining in the warmer months. It overlooks the very peaceful conservancy and is a special place for a quiet read or fun games in the rain. No worries of power outages here with both a gas generator and the new Tesla Powerwall! Above the garage is a versatile space that can be used as a studio, guest room, mother-in-law suite, or a study boasting a mini-split, refrigerator, and three-quarter bath. Enjoy the fire pit in the evening, under the stars. Watch the bluebirds at the birdhouses as they raise their families, the chipmunks that scurry, and the turkeys in the meadow. This is a wonderful neighborhood. Make it yours. Open house Saturday, April 25th 11am - 1pm

Listed by Christine Lewis of Brattleboro Area 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.

39 Stoney Brook Road Londonderry VT 05148

Londonderry, VT39 Stoney Brook Road

Price$610,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5088719

  • Residential Single Family
  • Full Bath 2
  • Address 39 Stoney Brook Road
  • Bedrooms 3
  • Bathroom 4

Located on a quiet country lane in Londonderry, this modern farmhouse offers a mountain retreat without traveling far. From the front porch, enter the sunny, open-concept living/dining room and kitchen, with a dining counter in the middle of it all. Outside the kitchen/dining room, the southern patio is framed by landscaping and raised garden beds, with westerly views of the neighboring pond, rolling hills, and setting sun. Also on the first floor are the en-suite primary bedroom and guest 1/2 bathroom. Upstairs are two bedrooms, a full bathroom and an office, all with windows framing the bucolic setting with a peek at the distant ridgeline. The basement offers a gym and second living room, as well as a 3/4 bath and mudroom area ushering you out to the hot tub patio under the stars. The spacious, well-organized 24' x 30' outbuilding is equipped with a Modine heater, shelving, electric outlets, and expansive room for ski tuning, woodworking, carpentry projects, indoor gardening, or storage of ATVs, extra cars, and more. Solar panels on the outbuilding roof typically generate all of the property's electric power. At 39 Stoney Brook, you are 3 minutes to the Londonderry Farmers' Market, grocery, Vermont Butcher, and Viking Nordic Center; 5 minutes to Lowell Lake and Magic Mountain; 12 minutes to Bromley Mountain and Wild Wings X-Country Center; 20 minutes to Stratton Mountain; 23 minutes to Manchester.

Listed by Jamie Luke of TPW Real Estate

{$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: 6.52% 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.

53 Country Lane Wardsboro VT 05360

Wardsboro, VT53 Country Lane

Price$610,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5090511

  • Residential Single Family
  • Full Bath 3
  • Address 53 Country Lane
  • Bedrooms 4
  • Bathroom 3

Tucked between Mount Snow and Stratton, this charming mountain retreat offers the perfect blend of adventure, comfort, and classic Vermont living. Set in the heart of Wardsboro, this property provides easy access to both year-round recreation and peaceful natural surroundings. After a day on the slopes or exploring the nearby Green Mountain National Forest, cozy up beside the inviting wood burning fireplace or unwind on the private balcony surrounded by the beauty of the Green Mountains before rejuvenating with a soak in the hot tub. A lovely screened-in porch creates the perfect space for morning coffee, summer evenings, or taking in the crisp mountain air. With an open kitchen/dining/living space and a large family/game room, this home has plenty of space to make new memories. Outdoor enthusiasts will appreciate access to nearby snowmobile trails, endless hiking opportunities, and all the recreation Southern Vermont is known for. Whether you're seeking a full-time residence, weekend getaway, or investment property, this home captures the warmth, charm, and lifestyle that make Vermont living so special.

Listed by Mike Masters and Betsy Wadsworth of Four Seasons Sotheby's Int'l 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.

556 Saw Mill Road Wardsboro VT 05360

Wardsboro, VT556 Saw Mill Road

Price$609,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5082001

  • Residential Single Family
  • Full Bath 1
  • Address 556 Saw Mill Road
  • Bedrooms 4
  • Bathroom 4

Set on a private one-acre lot in Wardsboro, this well-designed 4-bedroom, 4-bathroom home with a dedicated office space and attached garage offers over 3,000 square feet of living space. Ideally located just 12 minutes from Mount Snow and 20 minutes from Stratton Mountain Resort, the property is perfectly positioned for year-round enjoyment - from winter skiing and riding to relaxing summer evenings on the deck. Inside, the home features a bright open floor plan with 10-foot ceilings on every level and wood flooring throughout. The main living area flows effortlessly from the kitchen to the dining space and into a warm, inviting sitting area anchored by a wood stove - ideal for relaxed gatherings or an energetic game night with friends. The second floor offers a spacious primary suite with an ensuite bath, two additional bedrooms, a full bathroom, and a dedicated office space. A fully finished lower level adds versatility, complete with a beautiful fireplace, generous space for entertaining, and large sliders that open directly to the backyard. Outdoor living is equally impressive. An oversized front porch with an attached gazebo creates a welcoming first impression, while the expansive back deck off the dining room is perfectly sized for outdoor dining, cookouts, and comfortable patio furniture. The private yard offers space to unwind, entertain, and enjoy the peaceful surroundings in every season. Outdoor recreation is right nearby, including hiking, swimming, paddleboarding, and fishing at Grout Pond, along with the extensive backcountry mountain biking at the Stratton town forest or Stratton Recreation Center. You can also enjoy tennis, pickleball, or a swim at the neighborhood recreation center.

Listed by Kim Meeker 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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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.

4448 Route 100 Wardsboro VT 05355

Wardsboro, VT4448 Route 100

Price$599,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5065488

  • Residential Single Family
  • Full Bath 2
  • Address 4448 Route 100
  • Bedrooms 4
  • Bathroom 3

This four-bedroom, three-bathroom home with additional office or bonus room space can be yours! Offering a spacious family room with fireplace, a cozy den off the garage entry. A formal dining room in addition to kitchen that allows for another sitting area with plenty of wall space to decorate. The location is set back off Route 100, so very minimal road noise yet the highway is always maintained well by the state. Private pond with a sprawling yard. The two-car attached garage with access to both the basement and storage space above is very convenient for the colder months! Cedar exterior siding with a Brazilian rosewood oil finish, lovely hardwood flooring throughout most of the home with a walnut finish. Only two smaller rooms have carpeting. Wonderful mudroom entryway to hang your coats and boots. A surround sound system both inside and out for your enjoyment during our warmer months here in southern Vermont. This home has been lovingly cared for and enjoyed for many years! Nice concrete patio at the front of the home with custom Coolaroo shades and an additional rear deck off the back of the home with easy access through the French doors located just off the kitchen overlooking the pond. This home is a solid, well-built home with a nice layout. Very short driving distances to both Stratton and Mount Snow. Truly a hidden gem!

Listed by Julie Lowe of Lowe's Real Estate, 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: 6.52% 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.

673 VT Rte 121 East Grafton VT 05146

Grafton, VT673 VT Rte 121 East

Price$599,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5074888

  • Residential Single Family
  • Full Bath 1
  • Address 673 VT Rte 121 East
  • Bedrooms 5
  • Bathroom 3

Historic Charmer, this c. 1830 farmhouse has been loved and stewarded by its current owners for half a century. It is time to pass this amazing vintage home on to another lucky family. The house has original features including 2 fireplaces, curved plaster walls and beautiful honey colored wide pine floors. The first floor offers an eat-in- kitchen, formal dining room, spacious sunny living room with adjacent family room also a bedroom and combination bathroom laundry. The second floor has 3 additions bedrooms with two bathrooms and a large bunkroom with 5 built in bunkbeds. Take your pick, enjoy privacy outback in the large screen porch or listening to the babbling Saxtons River on the covered front porch. This property has 45 acres with groomed lawn surrounding the house and a large stand of natural forest along the hillside. The property also offers a classic post and beam barn for vehicles, recreation equipment or endless possibilities. Walking distance to, the Phelps Barn Pub, The Grafton Inn, the Market or the village library. Minutes to Summer and Winter activities at the Grafton Trails, Okemo or Stratton . Come be a part of the Vermont experience.

Listed by Janet Lucier of Barrett & Valley Assoc. Inc

{$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 15, 2026 4:22 AM UTC

 

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