$499,000 $210 per sq.ft. Wilmington VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2372  |  Acres: 0.59
Tuesday Jun 24, 2025
Description: Contemporary retreat in the heart of Chimney Hill. Set on a double lot along a paved road offering the perfect balance of comfort, style and year round convenience. Located just minutes from Wilmington village, Lake Whitingham, Mount Snow and scenic trail that leads to the summit of Haystack Peak in the Green mountain National Forest. The bright, open concept interior is filled with natural light, thanks to expansive windows that bring the outdoors in. Living with wood burning fireplace, kitchen with stainless appliances including a premium 6-burner Viking gas range. Step outside to wrap-around deck ideal setting for summer relaxation and outdoor entertaining. Spacious primary suite is a true retreat with a three-sided gas fireplace, multiple sitting areas and large picture windows that capture the morning sun. Spiral staircase leads to a loft-style play area. The entry level offers a family room with pool table and bar area, great for gatherings as well as an attached garage providing excellent storage. As a part of Chimney Hill, you'll enjoy full access to a wide array of amenities: Clubhouse with indoor and outdoor pools, hot tub, fitness center, game room, theater room, lounge areas, tennis courts, hiking and snowmobile trails, and an ice skating rink. Whether you're looking for a year-round home or a Vermont getaway, this property offers a rare blend of privacy, recreation, and comfort in one of the region's most sought-after communities-A perfect four-season retreat! See MLS Property & Listing Details & 31 images.

$499,000 $260 per sq.ft. Wilmington VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1920  |  Acres: 7.1
Wednesday Oct 8, 2025
Description: Vermont mountain getaway perched on a private parcel at the end of a quiet country road, this charming mountain retreat offers sweeping long-range views spanning from the Green Mountains within the National Forest north to Mount Snow and east toward neighboring Marlboro. Enjoy breathtaking sunsets from the covered front porch or relax in the outdoor hot tub surrounded by nature. Inside, the open-concept floor plan features a cozy living area with a pellet stove and a convenient lift system for easy refilling from the lower level. The main floor offers a primary bedroom, a full bath with laundry, and a spacious mudroom. Upstairs are two additional bedrooms and a second bath, providing comfortable space for family or guests. The walkout lower level includes utilities and garage space for two vehicles, with potential to finish into a family or recreation room. Outdoor highlights include a firepit seating area and a raised platform treestand--perfect for peaceful moments or enjoying the scenery. Conveniently located just minutes from Wilmington for shopping and dining, Lake Raponda for swimming, and Molly Stark State Park for hiking. Being sold mostly furnished, this is a ready-to-enjoy Vermont getaway. See MLS Property & Listing Details & 41 images. Includes a Virtual Tour

$250,000 $166 per sq.ft. Windham VT Home »

5 Beds | 2 Baths |   Total Sq. Ft. 1504  |  Acres: 2.6
Tuesday Dec 17, 2024
Description: Great location for primary or vacation home. Near Burbee Pond in Windhame. 2.6 acres and possibly small commercial. 4 Plus bedrooms with one full bath and a half bath on main floor. Home is ready for your improvements. Close to ski resorts! See MLS Property & Listing Details & 18 images.

$335,000 $265 per sq.ft. Windham VT Home »

Price Change! Reduced by $24,000 down 7% on September 27th 2025
3 Beds | 3 Baths |   Total Sq. Ft. 1266  |  Acres: 1.9
Friday Jun 13, 2025
Description: Charming and meticulously maintained, this classic Vermont A-frame with a tasteful addition offers the perfect blend of character and comfort. Nestled on just under 2 acres, the home features 3 cozy bedrooms, warm wood accents, and inviting living spaces filled with natural light. Whether you're enjoying a quiet morning on the deck or taking in the peaceful surroundings, this property is a true Vermont retreat. Located in Windham, a quaint village rich in history and natural beauty, you'll find yourself in the heart of Southern Vermont. Established in the 18th century, Windham is known for its rolling hills, outdoor recreation, and close-knit community. A rare gem in a timeless setting! See MLS Property & Listing Details & 28 images.

$397,777 $262 per sq.ft. Windham VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1520  |  Acres: 2.34
Thursday Aug 28, 2025
Description: Nestled alongside a meandering stream, this perfectly private Cape-style home offers an idyllic setting with over 2 acres of lush land, perfect for play, gardening, or entertaining. Built in the late 80's this home features 3 bedrooms and 2 baths blending timeless appeal with modern conveniences. First floor bedroom and a 2 car garage attached with a practical mudroom offers easy living. 5 new heat pumps provides efficient heating and cooling. Located near Magic Mountain ski resort and Lowell Lake state park keeping you active year-round. See MLS Property & Listing Details & 33 images.

$425,000 $129 per sq.ft. Windham VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 3300  |  Acres: 1.3
Thursday Sep 25, 2025
Description: Welcome to 715 Chase Road where you will find peace, tranquility and even convenience. This home offers so much bang for its' buck, you must come see it to believe it. Three bedrooms one full bath and laundry on the main level along with den, breakfast room and inviting living area with wood burning fireplace. The kitchen boasts plenty of counter and cupboard space with newer appliances and a little breakfast bar. The upper level features the fourth bedroom area in it's own mother in law floor away from the rest of the living areas. That suite has a separate enclosed porch as well as deck overlooking the 25' x 16' above ground pool. Relax outside on the raised decking. Workshop to store your riding mower and firewood. The established groomed lot is level and the address allows easy access to Windham's town public roads. Take a bike ride to the close by Burpee Pond. This wonderful well kept property is your next home run investment. Don't wait too long to take a tour ! See MLS Property & Listing Details & 50 images.

$499,000 $158 per sq.ft. Windham VT Home »

Price Change! Reduced by $50,000 down 10% on October 14th 2025
4 Beds | 4 Baths |   Total Sq. Ft. 3152  |  Acres: 5.08
Monday Sep 22, 2025
Description: Classic 1875 colonial home located on 5 acres in beautiful Windham VT. Home sits well off the road for privacy. Large first floor with kitchen, two living rooms, dining room and half bath with laundry. Second floor has 3 bedrooms and 2 full baths. Detached 2 car garage has a first floor bonus room with 1 bedroom 1 bathroom ADU on the second floor with separate utilities. Great rental history/potential. There is a nice barn with lots of storage for your equipment, wood or animals. The house sits high above a beautiful stream with a bridge over it to a small island which has another shed/summer animal barn. Beautiful perennial gardens could be brought back to life with a bit of weeding. The house needs a bit of TLC but could be a wonderful country escape for the right buyer. See MLS Property & Listing Details & 34 images. Includes a Virtual Tour

$256,500 $208 per sq.ft. Windsor VT Home »

3 Beds | 1 Baths |   Total Sq. Ft. 1232  |  Acres: 0.13
Sunday Sep 21, 2025
Description: Located near the end of a dead end street and also near Mill Pond, this home is convenient to where you need to go! There's a nice covered front porch as well as a detached 1 car garage. The interior features 3 bedrooms, formal dining room, a nicely sized living room and character and charm throughout. This property is definitely worth checking out! See MLS Property & Listing Details & 26 images.

$269,000 $204 per sq.ft. Windsor VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1320  |  Acres: 0.13
Tuesday Oct 7, 2025
Description: Step into the timeless appeal of this beautifully maintained 1920s home, ideally situated in the heart of Olde Windsor. The inviting front patio welcomes you into a charming entryway that opens to a cozy living room, perfect for relaxing evenings or entertaining guests. Gleaming hardwood floors flow through the entry and dining areas, adding warmth and character throughout. The spacious dining room connects seamlessly to a well-appointed kitchen, offering both functionality and charm. A conveniently located half bath on the main floor includes an integrated washer and dryer for added ease. From the dining area, step out to the back patio and take in serene views of the expansive backyard, ideal for outdoor gatherings, gardening, or summer barbecues. Upstairs, you'll find three comfortable bedrooms and a full bath, providing plenty of space for family or guests. Perfectly positioned between Mill Pond, Lake Runnenede, and the Connecticut River, this home offers a unique blend of tranquility and convenience. Enjoy a leisurely 15-minute walk to Main Street, where local shops and restaurants create a vibrant small-town atmosphere. Combining vintage charm with thoughtful updates, this Olde Windsor gem is ready to welcome its next chapter. See MLS Property & Listing Details & 33 images.

$325,000 $133 per sq.ft. Windsor VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2452  |  Acres: 0.75
Thursday Jun 5, 2025
Description: Charming Duplex in the Heart of Windsor - Ideal for Owner-Occupants or Investors! Discover a fantastic opportunity to own a versatile, income-producing duplex in the vibrant and historic town of Windsor. Perfectly suited for an owner-occupant looking to offset their mortgage with rental income--or a savvy investor seeking solid returns--this well-maintained property offers both comfort and cash flow. Each unit features 2 spacious bedrooms, 1 full bathroom, a bright living area, and a spacious kitchen, making it ideal for tenants or personal use. Separate utilities ensure ease of management and straightforward billing, while continued thoughtful maintenance enhances long-term value and efficiency. Just minutes from local shops, dining, and schools, this property offers small-town charm with big investment potential. Enjoy easy access to I-91 and nearby recreational opportunities including hiking, skiing, and kayaking/fishing. Whether you choose to live in one unit and let the other help pay your mortgage, or fully rent both for reliable income, this duplex is a rare find in a desirable location. Don't miss your chance to own this flexible and financially smart property in one of Vermont's most charming towns. Schedule your showing today! See MLS Property & Listing Details & 36 images.

$329,000 $200 per sq.ft. Windsor VT Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1649  |  Acres: 0.18
Monday Sep 29, 2025
Description: Open House 10/4/1025 11Am-1Pm. This lovingly maintained Cape-style home, perfectly set on a 0.18-acre corner lot. With 2 bedrooms, 1.5 bathrooms, a welcoming covered porch, and spacious basement, this home blends classic Vermont character with everyday comfort. The home has a standing seam roof and a brand new boiler, with timeless features such as built-in cabinetry, hardwood floors, and ample closet space. Bonus rooms on each floor add to its charm and flexibility. The two-car garage with attic storage offers plenty of room for vehicles, tools, and more. Inside, the traditional layout provides a functional, warm, and inviting flow but leaves room for adding your own personal touches. Enjoy the convenience of being within walking distance to local amenities like Kennedy's Pond and the Windsor Fairgrounds all while savoring the peace and space of your corner lot, ideal for gardening, play, or quiet relaxation. See MLS Property & Listing Details & 41 images.

$399,900 $238 per sq.ft. Windsor VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1680  |  Acres: 0.96
Thursday Sep 18, 2025
Description: Welcome to this well-kept ranch home in the heart of Windsor, VT. Offering 3 bedrooms and 1.5 baths, this home provides a comfortable layout, perfect for everyday living. The spacious living room is bright and inviting, opening easily into the eat-in kitchen where there's plenty of room for family and friends to gather. This is what a true turnkey home looks like; new roof, windows, siding, decking, electrical, flooring, whole house generator, and beautiful new baths and kitchen complete with granite countertops. Boiler was replaced just before these owners purchased in 2016. Even the basement has potential to be fully finished if you need more living space or to have a workshop or home studio. Enjoy the convenience of a 2-car garage and a level lot that's ideal for gardening, pets, or outdoor entertaining. Single-level living makes this property easy to maintain, while the location offers quick access to Windsor's shops, restaurants, and local amenities. Whether you're looking for your first home, a place to downsize, or a Vermont getaway, this ranch is full of potential and ready for its next chapter. See MLS Property & Listing Details & 28 images.

$499,000 $344 per sq.ft. Windsor VT Home »

Price Change! Reduced by $136,000 down 27% on October 7th 2025
3 Beds | 3 Baths |   Total Sq. Ft. 1452  |  Acres: 10.18
Monday Jun 16, 2025
Description: Enjoy privacy and lovely views from this well executed contemporary home overlooking copious gardens and mature plantings to a spectacular pond with an arched footbridge (spotlights highlight the bridge after dark) to access your own little island. Beautiful updates throughout the home include new maintenance-free manufactured cedar-tone shingles on the entire house and workshop shed. The kitchen features custom oak cabinetry, granite counters and updated appliances. The living room has sweeping cathedral ceilings, hardwood walls, oversized windows, and a wood burning fireplace. There is a primary Bedroom ensuite, and a guest powder room off of the foyer mudroom complete with slate floors. Step out to a private iron balcony with Trex decking and spiral stairway accessing a stone terrace below complete with fire pit, water feature and screened gazebo. Upper level has a spacious loft area, and a second bedroom. The walk out lower level includes a third bedroom, studio/rec room (could accommodate overflow guests) and laundry, plus a wine or root cellar. Oversized two car garage with plenty of storage above. Located just minutes from I 91. Easy access to Upper Valley, DHMC, Woodstock, skiing and all recreation. See MLS Property & Listing Details & 39 images.

$375,000 $279 per sq.ft. Winhall VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1344  |  Acres: 1.03
Saturday Aug 30, 2025
Description: Escape to the mountains in this charming A-frame, ideally located between the bustling town of Manchester and the area's best ski mountains. This home is your perfect base for year-round adventure, putting you just minutes from world-class skiing, hiking, mountain biking, and shopping. Inside, you'll find a comfortable layout featuring 3 bedrooms, 2 bathrooms, and a home office that can easily flex to accommodate extra guests. Cozy up by the wood-burning fireplace after a day on the slopes or soak up the sun on the inviting deck. This isn't just a home; it's a gateway to the best of Vermont. Property is being sold as is. Septic has failed. State Permit and design and Quote to replace found in documents. See MLS Property & Listing Details & 22 images. Includes a Virtual Tour

$425,000 $436 per sq.ft. Winhall VT Home »

2 Beds | 1 Baths |   Total Sq. Ft. 974  |  Acres: 1.01
Saturday Oct 4, 2025
Description: A cozy chalet style home tucked in the woods in Winhall. Enjoy peaceful and private living with three seasons of beautiful mountain views and twinkling valley below. Hot tubbing and star gazing year round. Second owner since 1976. Updates include new metal roof, siding, deck, hot tub, kitchen, floors, bath, detached shed and more. A short drive to Bromley and Stratton Resorts. Lots of easily accessible activities such as hiking, mountain biking, cross-country skiing, golfing and pickle ball. An array of fun shops, restaurants, galleries in nearby Manchester So much nature and history to explore, too. A great place to relax and enjoy sunsets and snowfalls with family and friends - serenity now! Fondly named "Snugaboo" by owners. See MLS Property & Listing Details & 21 images.