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$715,000
4 Beds 3 Baths 5081734 MLS
Built in 1818 for early woolen mill owner John Woolley, the Woolley House is a rare and beautifully preserved Federal-style brick residence that blends historic character with the demands of contemporary life. Listed on the National Register of Historic Places within the Mechanicsville Historic District, this exceptional property offers unique architectural significance. Classic period details are evident throughout: antique brick walkway, a side-hall layout, blind-arch entryway, fanlight transom, wide pine floors, 12-over-12 windows, and an original central cooking hearth complete with an iron crane and concealed baking ovens. What truly distinguishes the Woolley House is its remarkable versatility for today's professional lifestyle. A converted carriage barn offers three separate private office suites with garden views and exterior access, creating an ideal environment for remote professionals, entrepreneurs, consultants, creatives, or anyone operating a home-based business. Whether you need dedicated workspace for multiple household members, private client meeting areas, or room to grow, the flexibility is exceptional. Paired with fiber-optic internet service, the property delivers the connectivity modern professionals demand while offering comfort and character impossible to find in any conventional office setting. The main residence is equally impressive. The lower level features a custom marble kitchen, formal dining room, three-quarter bath, laundry, and two gracious sitting rooms. Upstairs, four bedrooms, two updated bathrooms, a lounge, a finished loft, and a library retreat offer generous, well-appointed living space. Porches at the back of the house offer three-season enjoyment. A large attic provides significant storage space or potential additional use. Outside, mature perennial gardens, a bank of beautiful rhododendrons, and one of Windham County's most admired hosta collections create a peaceful and private setting.

587 Vt Route 121 E, Grafton

$424,000
3 Beds 2 Baths 5076445 MLS
Thoughtfully-designed gambrel on the outskirts of Derby. Was previously a mini horse farm with horse barn. Large meadow up behind the house completely secluded. You enter through a large mud room that also has garage access and back yard access, and laundry. The kitchen/dining area is very spacious spanning the width of the house and opening onto the 34 foot wide covered back porch. Living room, 3/4 bath, and 1 bedroom complete the 1st floor. Upstairs are 2 more bedrooms and a full bath. The full walk-out basement has large windows and would accommodate much more living space. And, 62 acres!!!! Same owners built this well-maintained home in 1990, but now it is time to move one. Road frontage is estimated. Motivated seller.

3724 Vt Route 105th Rd, Derby

$549,000
5 Beds 3 Baths 5074888 MLS
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.

673 Vt Rte 121 E, Grafton

$650,000
5044879 MLS
Exceptional Investment Opportunity in Chester, VT Discover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been meticulously designed, incorporating reclaimed materials that add warmth and charm to the contemporary aesthetic. In addition to the inviting residential spaces, this property includes a versatile two-story commercial area currently occupied by a successful, established business making it ideal for investors or entrepreneurs. With prominent visibility and high traffic flow, the commercial space is well-suited for a variety of ventures, from retail to office use. Situated just a short drive from Okemo Mountain, this property offers year-round appeal for outdoor enthusiasts and tourists alike. Plus, it is conveniently located near the vibrant shops, dining options, and recreational activities of Chester and Ludlow. This versatile property allows for multiple avenues of income - whether you choose to occupy one of the residential units, rent both out, or utilize the commercial space, the possibilities are endless. Don't miss your chance to own a piece of this thriving community.

3630 Vt Route 103 N, Chester

$325,000
3 Beds 2 Baths 5053200 MLS
Back on the market due to a change in the buyers’ circumstances. Don’t miss your chance to tour this newly relisted property. Filled with beauty, style, and warmth, this 3-bedroom, 2-bath home sits on 4.4 acres and offers an array of standout features. Highlights include a stunning fieldstone fireplace and an expansive Great Room, perfect for hosting large gatherings or unwinding by the cozy pellet stove insert. Enjoy living space across three levels, along with a serene, spring-fed pond that enhances the property’s natural appeal. The lower level features a dedicated laundry room and a versatile bonus room with a second fireplace and convenient walk-out access to both the carport and garage. Step outside and you’ll find two covered porches ideal for relaxing or entertaining, a designated outdoor cooking area, and a level yard perfect for lawn games. The brook trout pond provides year-round enjoyment, while direct access to the VAST snowmobile trails makes this property a true outdoor enthusiast’s retreat.

3212 Vt Route 114 E, Norton

$499,000
3 Beds 3 Baths 5108296 MLS
Qualified pricing - check with your agent to see if you qualify! Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"

32 Barnes Brook Rd Unit 10.3, Middlebury

$399,000
2 Beds 2 Baths 5104885 MLS
Welcome to your own peaceful country retreat, where wide pine floors, abundant natural light, and 16.7 acres create a setting that feels instantly inviting. Imagine starting your morning with coffee or unwinding at the end of the day with a glass of wine in the gazebo overlooking the pond—this is a property designed for enjoying the simple pleasures of country living. Inside, the open-concept floor plan is comfortable and welcoming. The efficient kitchen features stainless steel appliances and soapstone countertops and opens to a spacious dining area with direct access to the back deck—perfect for grilling and outdoor dining. Just off the kitchen is a generous living room with a vaulted ceiling, along with an office or study, half bath, and a storage room that could easily be converted back into a screened porch. Upstairs, you'll find two bedrooms and a 3/4 bath, along with built-ins just waiting to be filled with your favorite books and treasures. The walkout lower level offers additional usable space with a gas stove and sliders leading to the backyard. The unfinished portion provides a workbench, laundry area, and plenty of room for storage or projects. Outside, the property has a detached two-car garage, shed, circular driveway, pond frontage, and 16.7 acres surrounded by the natural beauty of a peaceful country setting. All of this is just five minutes from the charming village of Walpole and an easy drive to Keene. The exterior is ready for some attention and care, but the setting, acreage, character, and potential make this property a wonderful opportunity. Bring your ideas and make this hidden gem your own!

148 Barnett Hill Rd, Alstead

$499,000
3 Beds 3 Baths 5101838 MLS
Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"

44 Barnes Brook Rd Unit 10.1, Middlebury

$388,900
2 Beds 2 Baths 5088391 MLS
Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This two-bedroom townhome will be ready for occupancy in May 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. Step inside the open concept first-floor living area, with a generous kitchen featuring an island with seating, Energy Star appliances, and direct access to a private deck, perfect for morning coffee or evening relaxation. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze. A powder room on this level is great for guests. Upstairs, you will find 2 spacious bedrooms and a full bath. The lower level provides private garage parking, laundry room with utility space, and a handy bonus room- perfect as a mudroom, storage, or exercise room. Future community amenities will include green space, a community garden, access to trails, and more. Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Inquire for more details! Photos are "Likeness Only"

41 Barnes Brook Rd Unit 9.2, Middlebury

$765,000
3 Beds 3 Baths 5085570 MLS
Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The wrap-around, covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"

30 Barnes Brook Rd Unit 10.4, Middlebury

$585,000
2 Beds 2 Baths 5055964 MLS
Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This two-bedroom townhome will be ready for occupancy in May 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. Step inside the open concept first-floor living area, with a generous kitchen featuring an island with seating, Energy Star appliances, and direct access to a private deck, perfect for morning coffee or evening relaxation. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze. A powder room on this level is great for guests. Upstairs, you will find 2 spacious bedrooms and a full bath. The lower level provides private garage parking, laundry room with utility space, and a handy bonus room- perfect as a mudroom, storage, or exercise room. Future community amenities will include green space, a community garden, access to trails, and more. Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Inquire for more details! Photos are "Likeness Only"

39 Barnes Brook Rd Unit 9.3, Middlebury

$585,000
2 Beds 2 Baths 5055963 MLS
Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This two-bedroom townhome will be ready for occupancy in May of 2026. With energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. Step inside the open concept first-floor living area, with a generous kitchen featuring an island with seating, Energy Star appliances, and direct access to a private deck, perfect for morning coffee or evening relaxation. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze. A powder room on this level is great for guests. Upstairs, you will find 2 spacious bedrooms and a full bath. The lower level provides private garage parking, laundry room with utility space, and a handy bonus room- perfect as a mudroom, storage, or exercise room. Future community amenities will include green space, a community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"

35 Barnes Brook Rd Unit 9.4, Middlebury

$440,000
3 Beds 3 Baths 5106889 MLS
This is a well-built Dutch Colonial style home with exposed beams and 3 fireplaces, one with a Vermont Castings gas stove, and one hearth, all wrapped in cedar shake siding. The home offers 3 bedrooms upstairs, plus a den/office on the first floor, and 2.5 baths, all set on 6.91 acres with 472.3'+- river frontage, a pond, and open field land. The property also features a 5-stall horse barn with a heated office and open sheds making it an ideal setting for equestrian pursuits, hobby farming, or simply enjoying the peace and beauty of the countryside. The property is conveniently located just 6 miles from I-91 and approximately 20 minutes from Hanover. This special property combines privacy and rural charm with access to excellent primary and secondary schools, libraries, a publicly accessible lake beach, many walking trails and other family-friendly amenities. The unfinished basement ceiling height exceeds 8-feet; a renovation will significantly increase the total finished floor space, or enable a workshop addition. With some TLC, this home’s magic will be restored, and the investment will yield longer term value. Sign on property. This is an estate sale; the property is being sold as-is, where-is.

1049 Barker Rd, Thetford

$689,000
5 Beds 3 Baths 5090735 MLS
MOTIVATED SELLER! PRICED BELOW THE CURRENT ASSESSED VALUE. Offering efficiency, sustainability, and peace of mind, this move-in ready five-bedroom Colonial sits on eight private acres in Post Mills/Thetford, Vermont. Energy-conscious upgrades include rooftop solar panels and an EV charger, adding modern efficiency to this exceptional property. The oversized attached garage and large tiled mudroom provide a practical everyday entry space. The spacious kitchen features a breakfast bar with seating for family and friends and opens to the light-filled dining room, creating an ideal layout for entertaining. The first floor also offers both a living room and a separate family room/den. Upstairs, you'll find five bedrooms, including the primary suite with an ensuite bath and generous closet space. The fully insulated lower level includes a partially finished basement with flexible space for a family room, home gym, playroom, workshop, and storage. A large sink, counter space, and double-door walkout add additional functionality and convenience. Enjoy the outdoors with private walking trails winding through the property's eight acres, offering opportunities for recreation, nature observation, and peaceful walks right from your doorstep. Conveniently located on the school bus route, this property combines rural privacy with everyday convenience. Formerly home to the Sugar Top Sawmill, the mill building offers endless possibilities for outdoor entertaining space, hobbies, storage, workshop space, or animals. A truly unique property with space, versatility, and modern upgrades throughout, all while enjoying tranquil country living just 20 minutes from Hanover and convenient access to Upper Valley amenities. Ready for its next owner to enjoy all this exceptional property has to offer.

1350 Barker Rd, Thetford

$740,000
5097867 MLS
A RARE combination of unspoiled forest (last cut in the 1960's), long road frontage, accessible terrain, and LOCATION! Multiple potential homesites (two easy-to-develop sites already soil tested) with View potential. Outdoors Lovers will appreciate that the Killington Resort and Town Recreation Area, state parks & accessible ponds, two golf courses, and National Forest are ALL only Minutes away! This 122+/- Acres lies East of Rt. 100 and North of River Road. The Tract enjoys 2/3rds mile of maintained road frontage. A recent Forester evaluation reports there is significant timber value. A Soil Test Report is available. Another adjacent 52 acres with two homesites and Ottaqueche riverfront may also be available for $250,000 (MLS #509885).

00 Vt Route 100 & River Road, Killington

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