Woodstock Homes for Sale

Welcome to Woodstock, Connecticut—a picturesque gem nestled in the heart of Windham County. Known for its rich history and vibrant community spirit, Woodstock offers a unique blend of rural charm and modern conveniences. With its rolling hills, serene landscapes, and lush greenery, this quaint town is an ideal retreat for those seeking a peaceful lifestyle while still being within reach of urban amenities.

Woodstock is home to a variety of recreational activities, including hiking, biking, and fishing, thanks to its beautiful parks and nature reserves. The town also boasts a thriving arts scene, with local galleries, craft fairs, and cultural events that celebrate the creativity of its residents. Families will appreciate the top-rated schools and the close-knit community that fosters a welcoming environment for all ages.

If you’re considering making Woodstock your home, you’ll find an array of charming properties available for sale. From historic colonial homes that exude character to modern new builds equipped with the latest amenities, there’s something for everyone. Many homes are set on spacious lots, offering plenty of room for outdoor activities and gardening, while others provide stunning views of the surrounding countryside.

With a diverse real estate market and a strong sense of community, Woodstock is not just a place to live; it's a place to thrive. Explore the homes for sale today and discover your dream home in this enchanting town!

Newest Woodstock Homes for Sale

$299,900

3 Beds ⋅ 1 Baths ⋅ 24214400 MLS

Welcome to 82 Little Pond Road in Woodstock, CT! This charming 3-bedroom, 1-bath ranch offers the convenience of single-level living on a .64-acre lot. With approximately 1,100 square feet of living space, this home features hardwood flooring, a cozy fireplace, and a functional floor plan. The full basement provides additional storage space and includes a one-car garage. Situated in a peaceful setting, the property offers a spacious yard with room to enjoy the outdoors. While the home could benefit from some updating and a little TLC, it presents a wonderful opportunity for buyers looking to add their personal touches and make it their own. With plenty of potential and a desirable Woodstock location, this property is ready for its next chapter. Bring your vision and explore the possibilities!

82 Little Pond Rd, Woodstock

$350,000

2 Beds ⋅ 1 Baths ⋅ 24214889 MLS

Charming Home on Beautiful Bungay Lake Experience the beauty of lakeside living in Connecticut's picturesque Quiet Corner! Welcome to this inviting and spacious 2-bedroom ranch, nestled in the beautiful town of Woodstock, Connecticut, along the desirable Bungay Lake. Whether you're searching for a peaceful year-round residence, a relaxing weekend retreat, or the perfect place to enjoy all four New England seasons, this property offers a wonderful opportunity to embrace the lake lifestyle. Step inside and discover a warm, welcoming home featuring convenient one-level living. The main floor offers two generously sized bedrooms, a full bathroom, a spacious living room, and a comfortable kitchen, providing plenty of room for everyday living and entertaining. The expansive lower level presents incredible potential for additional living space! With its generous size and convenient walkout access, this area offers endless possibilities for a future in-law suite, guest accommodations, recreation room, home office, or additional finished living area. Outside, enjoy the privacy of your own yard and driveway, creating a peaceful setting to relax, entertain, or simply appreciate the natural beauty surrounding you. Imagine experiencing all four seasons in this beautiful lakeside community - warm summer days enjoying the lake, breathtaking autumn foliage, peaceful winter scenery, and the refreshing beauty of spring. Located in Woodstock, one of

30 Hilltop Dr, Woodstock

$490,000

3 Beds ⋅ 2 Baths ⋅ 24214001 MLS

SOLAR PAID OFF AT CLOSING! Move in with solar working to keep your electric bills low from day one! This updated colonial sits on a peaceful acre on a quiet cul-de-sac in sought-after Woodstock, and the BIG-TICKET items are done: brand new roof and siding, new hot water heater, water filtration system, new washer and dryer, and a freshly painted back deck overlooking the yard and the above ground pool. The hard work is done and the peace of mind is included; all that's left is to make it your own. Enter through the new mudroom to a bright living room, separate dining room, and a kitchen with granite counters, stainless appliances and a breakfast bar. Off the kitchen, the bonus room with a pellet stove is ready for whatever you need: home office, guest space, or den. Right next to it, the laundry room includes a second shower and sink, with the half bath just down the hall. Upstairs, the primary bedroom has a walk-in closet, plus two more bedrooms and a full bath with a brand new double vanity. Generator ready, with a 2-car attached garage. Minutes from Woodstock Academy, scenic Route 169, local farms, orchards and the Woodstock Fairgrounds, with easy access to I-395 and Massachusetts.

21 Fairfield Dr, Woodstock

$369,000

3 Beds ⋅ 1 Baths ⋅ 24187880 MLS

A little charm, a lot of heart, and a location worth getting excited about! Nestled in Woodstock with deeded rights and beach access to highly sought-after Witches Woods Lake, this inviting 3-bedroom, 1-bath ranch offers comfort, warmth, and the ease of one-level living. The home has been lovingly maintained and thoughtfully updated, including a kitchen remodel in 2023 with new cabinets, appliances, and flooring, offering a fresh and functional space for everyday living. The spacious deck is a wonderful place to enjoy morning coffee, gather with friends, or simply unwind. Downstairs, the finished lower level offers a cozy rec room and dedicated office area, providing extra space to make your own. Improvements over the years include a roof in 2018, water heater in 2021, interior and exterior doors in 2023, and well tank and well cap in 2024. Filled with warmth, character, and pride of ownership, this inviting home is ready for its next chapter and someone new to make it their own.

1629 Rte 171, Woodstock

$339,900

4 Beds ⋅ 2 Baths ⋅ 24212685 MLS

What started as just a summer cottage has been transformed over the 50 years of ownership into a great lake view & access home. This home features over 1,700 sq. ft. on two floors, 4 total bedrooms along with 2 full bathrooms. The first floor has a large living room with pellet stove heating that satisfies the major of the heating needs. There is a good working space kitchen along with a rear sunroom/plant room/dining area. There are two bedrooms, a full bathroom with tub/shower along with the laundry on the main level. The second floor was a full addition years ago. There are two very good-sized bedrooms, a sitting area/den, along with an additional full bathroom. You will even find a second story open deck for enjoying nature. Home features a full walk-up attic with good access & storage. The basement, once just a small crawl space, was excavated out and a block foundation was installed. A propane warm air heating system, propane water heater, along with an additional chimney flue for woodstove can be found. Home has deeded access & lake rights to Lake Bungee and is just walking distance from private beaches and boat launches.

101 Beaver Dam Rd, Woodstock

$379,900

3 Beds ⋅ 2 Baths ⋅ 24211726 MLS

If you're looking for a place to be surrounded in all that nature has to offer, you'll want to call this home! This 3 bedroom, 2 bath, saltbox colonial is sited on a double lot, bordering Wyndham Land Trust. You'll love watching the deer and other wildlife from the 10'x20' deck. As a part of the private community of Lake Bunggee, you may also take a short stroll to the beaches to enjoy water rights and access. The lake is about 112 acres to enjoy boating, fishing, swimming and hiking areas. The light filled, open floor plan is perfect for entertaining; vaulted ceiling living room/dining area has hardwood flooring, an expansive wall of windows, and slider open to deck. Tiled kitchen has cozy breakfast bar and spacious walk-in pantry. 1st floor bedroom has ensuite bath with shower. 2nd floor primary also has ensuite bath with tub/shower unit and walk-in closet. Additional bedroom on second floor. Walk-out lower level has wood stove. Updates include newer hot water tank, septic system, and oil tank. Roof shingles 2015. Welcome Home!

35 Old Sawmill Rd, Woodstock

$779,000

5 Beds ⋅ 4 Baths ⋅ 24209434 MLS

Set high on historic Woodstock Hill, this distinctive 19th-century property offers a rare combination of history, character, exceptional views, flexible living spaces, guest accommodations, gardens, and opportunity. Offering approximately 2,500 square feet, this beautifully maintained home features five bedrooms and three-and-a-half baths, along with multiple living areas and a beautiful sitting porch overlooking the surrounding landscape. The home has been thoughtfully adapted to accommodate both private living and hospitality, creating flexibility for a variety of lifestyles. Two separate, thoughtfully furnished guest suites provide an established short-term rental opportunity and have enjoyed strong bookings. Guests have included parents visiting their children attending Woodstock Academy and Pomfret School, families attending weddings and local events, and visitors seeking to experience the beauty and charm of Woodstock. The grounds offer another exceptional dimension. Flower-growing areas, gardens, and a flower stand have been developed by the current owners during their first year on the property, building upon their longstanding experience with gardening and growing. The property offers an exciting opportunity to continue and expand the flower-growing vision, create a garden-based business, or explore the possibility of a future studio or shop, subject to applicable approvals.

500 Rte 169, Woodstock

$379,000

3 Beds ⋅ 2 Baths ⋅ 24209276 MLS

Move in ready ranch offering updated one level living, a finished walkout basement, and a private, level yard, all in the desirable town of Woodstock! The open concept main floor features hardwood floors, abundant natural light, and an updated kitchen with upgraded cabinetry, countertops, center island, and eat-in area. The kitchen opens to the living room, creating an inviting space for everyday living and entertaining. Three spacious bedrooms and an updated full bath complete the first floor. The finished lower level adds flexible living space with an open layout, pellet stove, walkout access, half bath, and laundry room. This space is ideal for a family room, home office, recreation space, or guest area. Outside, enjoy the spacious deck overlooking the private yard, plus a storage shed. Set in a quiet Woodstock location with easy access to 395 and 84, this home is convenient to major routes and surrounding communities. An affordable opportunity to enjoy the charm of Woodstock with updates already in place. Nothing to do but move in!

1619 Rte 171, Woodstock

$339,900

3 Beds ⋅ 2 Baths ⋅ 24205731 MLS

WAKE UP TO THE LAKE AND LIVE THE LAKE LIFE! Welcome to 91 Beaver Dam Rd, where everyday living feels like a getaway. This inviting 3-bedroom, 2-bath home is ideally situated across the road from the beach, putting swimming, fishing, kayaking, and canoeing practically at your doorstep. Imagine starting your morning with a beautiful sunrise over the lake, enjoying your coffee, then heading out for a paddle or some of the area's great fishing. Take a leisurely walk along the quiet community roads, meet your neighbors, and enjoy the relaxed atmosphere of this wonderful lake neighborhood. Whether you're searching for a year-round home, a weekend escape, or a place where you and friends can gather and make lasting memories, this property offers the lifestyle you've been looking for. Spend your days on the water, enjoy peaceful evenings, and leave the hustle and bustle behind. This isn't just a home-it's an opportunity to own a piece of the lake lifestyle.

91 Beaver Dam Rd, Woodstock

$1,425,000

4 Beds ⋅ 5 Baths ⋅ 24205041 MLS

Set amid nearly 120 acres across four deeded lots, this impressive Woodstock property offers an exceptional combination of privacy, space and versatility. The stately Colonial features over 5,000 sq. ft. of living space with 4 bedrooms, 4.1 baths and 12 rooms. A grand two-story foyer leads to a dramatic two-story living room with soaring ceilings and abundant natural light. The spacious kitchen offers extensive cabinetry, granite countertops, stainless steel appliances, a large center island and adjoining dining area with access to the deck. The primary suite features a tray ceiling, walk-in closet and private bath with double vanity, soaking tub and separate shower. A finished walk-up third floor provides flexible bonus space for a home office, recreation room or additional living area. Adding even more versatility is a detached in-law/guest apartment with a separate entrance, kitchen, living area, bedroom, full bath and laundry. Three additional deeded lots are included with the main parcel, bringing the total offering to nearly 120 acres-a truly unique opportunity to enjoy space, privacy and the natural beauty of Woodstock.

329 Rte 198, Woodstock

$499,900

3 Beds ⋅ 3 Baths ⋅ 24203840 MLS

To be built 6.5 room Colonial Home in a cozy neighborhood in Woodstock, At this price, this home will go quick! You have time to make several customized selections. Located on a fairly level and private lot, Tayler Tr is a quiet 20 year old open space subdivision (all homes less 20 years old) located on the Union town line off Tayler Rd, of which the remaining 27.77 acres of the original 44 acres on Tayler Rd was donated to the Wyndham Land Trust. The 94 acres across the street on Tayler Rd (south side) was donated to Nature's Conservancy, so no other homes will ever be built on Tayler Rd. AI says 36 minutes to 1 College St, Worcester (Holy Cross) and 40 minutes to Hartford. Owner is licensed real estate agent.

8-2 Tayler Trl, Woodstock

$509,000

3 Beds ⋅ 2 Baths ⋅ 1422207 MLS

Looking for a home that exudes the character and craftsmanship of bygone days without the challenges of a true antique? 15 Paine District Road looks and feels like it's been here for centuries, but this gorgeous reproduction Saltbox is less than 40 years old. Hand-built by its original owner with extraordinary attention to craftsmanship and period-inspired detail, it offers the warmth and character of early New England architecture recreated for modern living. Huge blocks of granite form the entry steps to each of the three doors, while exposed rough hewn beams and an oversized fireplace harken back to quieter days. Custom cabinetry and millwork by the renowned craftsmen at Brunarhans can be found throughout the home, from the solid wood kitchen, custom chair rails and molding to the raised paneled wall surrounding the fireplace. The kitchen features a cooking island and charming bay window dining nook with built-in seating. The flexible floor plan offers 3 bedrooms, including one on the first floor currently used as an office with more beautiful built in floor to ceiling custom cabinetry. The second floor offers a spacious primary and two additional bedrooms, the smaller one currently being used as a separate laundry area and playroom. The oversized garage includes a workshop area and storage loft. If you think this property looks pretty now, just imagine it when the fall foliage blooms. Act now and you can be moved in by peak leaf season, your pumpkins and scarecrow await!

15 Paine District Road, Woodstock

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Woodstock Homes for Sale

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