Woodstock Homes for Sale

Welcome to Woodstock, Connecticut, a picturesque gem nestled in Windham County that beautifully blends rural charm with modern conveniences. Known for its rich history and stunning landscapes, Woodstock boasts a vibrant community where nature and culture coexist harmoniously. As you stroll through the town, you’ll be captivated by the historic architecture, lush farmlands, and serene lakes that define its character.

Woodstock is not just a feast for the eyes; it offers a plethora of outdoor activities for nature enthusiasts. With numerous hiking trails, parks, and recreational areas, residents can enjoy everything from peaceful walks to adventurous outings. The town is also home to various seasonal events, farmers' markets, and local festivals that foster a strong sense of community and celebrate the unique spirit of this charming town.

For those considering a move, Woodstock’s real estate market presents an array of homes for sale that cater to diverse tastes and lifestyles. From quaint cottages nestled in wooded areas to spacious family homes with sprawling lawns, there’s something for everyone. Whether you’re a first-time homebuyer or looking to settle into a serene retreat, Woodstock offers properties that combine comfort, style, and a connection to nature.

With its welcoming atmosphere, rich history, and beautiful surroundings, Woodstock, CT is not just a place to live; it’s a place to thrive. Explore the homes for sale today and discover the perfect backdrop for your next chapter in this enchanting town!

Newest Woodstock Homes for Sale

$1,425,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 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.

Woodstock

$399,900

3 Beds ⋅ 1 Baths ⋅ COMING SOON Status ⋅ 24205841 MLS

Discover the privacy and peaceful setting of this charming 1,334 sq. ft. ranch nestled on 2 level, wooded acres in beautiful Woodstock, conveniently located near the Massachusetts line. Built in 1973, this home offers 3 bedrooms, 1 full bath, and inviting spaces designed for comfortable everyday living. A standout feature is the wonderful four-season sunroom, complete with a woodstove, cathedral ceiling, and skylights-an ideal spot to enjoy the beauty of the surrounding property year-round. The living room features a fireplace with a wood insert, adding warmth and character to the home. All three bedrooms offer ceiling fans, and window A/C units provide seasonal cooling. The attached 2-car insulated garage includes electric, automatic garage door openers, and a convenient breezeway connecting directly to the house. For the car enthusiast, hobbyist, or additional storage needs, there is also a separate 3-car detached garage with electric, providing an abundance of workspace and parking. The completely fenced yard features sheep fencing and offers plenty of room for pets, gardening, or outdoor activities. A shed at the rear of the property also serves as a chicken coop, adding to the property's versatility and rural charm. Add'tl updates and features include 200-amp electrical service, a 2011 furnace, 2026 hot water system, and a 2023 well tank. A private, versatile property with plenty of garage space, usable acreage, and the peaceful Woodstock setting you've been looking for.

673 Brickyard Rd, Woodstock

$499,900

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24203840 MLS

To be built 7 room raised ranch 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.

8-2 Tayler Trl, Woodstock

$299,900

3 Beds ⋅ 1 Baths ⋅ COMING SOON Status ⋅ 24204986 MLS

Charming one-owner ranch nestled on a quiet country road in Woodstock, close to the Massachusetts border. This sweet home offers easy one-level living with three bedrooms, a full bath, hardwood floors in the living room and bedrooms, plus a comfortable eat-in kitchen. Enjoy the outdoors from the back deck overlooking the property, with the added convenience of walk-out basement and detached two-car garage. The roof is approximately 10 years old and a newer septic system (2010), this well cared for home is ready for its next family to make it their own. A wonderful opportunity to enjoy the peace and quiet and all that Woodstock has to offer while remaining close to area amenities and the Massachusetts border.

652 Brickyard Rd, Woodstock

$679,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24202453 MLS

Discover the timeless charm and endless potential of this antique home in Woodstock located down the hill from Woodstock Academy. Situated on a lovely country road while remaining close to all amenities. Entering through the side door into a lovely sitting/dining area with fireplace that opens to the kitchen, which flows into a large living room, perfect for gathering family or entertaining. There is plenty of space for a home office or den too. Head upstairs where there are 4 spacious bedrooms, the primary having its own dressing room, along with 2 full baths. Lovely wood flooring throughout the home. Rich with character and antique details, this special property offers a wonderful opportunity to refresh, restore and make it all your own. Set 8.5 acres, the grounds provide plenty of room for gardening, agriculture and animals or just a quiet place to relax. The beautiful post and beam barn adds character and versatility, while providing the foundation for hobbies, storage, or animals. Come and discover all the amazing features and opportunities this home has to offer!

122 Child Hill Rd, Woodstock

$600,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24204008 MLS

Modern amenities meet unmatched seclusion in this 2,000+ sq ft colonial. A mostly level lot offers abundant green space, fruiting plants, and perennials, while the side deck and yard open to a beautiful natural view of the Still River-ideal for outdoor entertaining or quiet, serene living. Inside, gleaming maple floors lead to a first-floor bedroom with attached pass-through bath, a modern eat-in kitchen with double wall ovens and a propane stovetop, a large dining room, and a spacious living room with a functional fireplace. Upstairs, a hallway full bath serves three additional bedrooms, including the primary suite with its own attached full bath. The walk-up attic's excellent ceiling height and volume create a strong opportunity to add livable square footage. The basement's layout and ceiling height are equally well suited to finishing and expanding the home further. An attached two-car garage and paved driveway provide ample parking. If you want modern comfort, privacy, and room to grow in a peaceful woodsy setting, this is the home for you!

47 Sherman Rd, Woodstock

$589,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24201418 MLS

There's something special about being able to see the lake from home and be at the water in just a short walk. Welcome to 4 Oak Drive, a thoughtfully cared-for 2-bedroom, 2-full-bath home with a spacious loft in the Lake Bungee community. With deeded lake and beach rights and views of the water, this newer home sits on an inviting corner lot surrounded by colorful flowers, raised vegetable gardens and touches of classic New England charm. Traditional stone walls along the adjoining historic cemetery add to the peaceful character of the setting. Inside, the open-concept kitchen with granite countertops and center island flows comfortably into the dining and living areas, with windows bringing in plenty of natural light and views toward the lake. Step out onto the deck to unwind and enjoy the glowing sunsets that cast a warm light across the property. Both bedrooms are on the main level, including the primary with a large walk-in closet, private full bath and sliders to its own small deck. Upstairs, the open loft offers flexible additional space along with two closets and attic storage. The full walk-out basement with sliders provides plenty of storage and potential for future finished living space. Generator hookup ready for added peace of mind. Lovingly maintained and easy to settle into, this home offers a welcoming place to enjoy the seasons, the lake and the simple pleasures of home, all while being conveniently located near the Massachusetts line and area amenities.

4 Oak Dr, Woodstock

$549,900

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24201270 MLS

There's something special about being the first to call a brand-new home your own! Set within a desirable Bunggee lake community in Woodstock Valley, this new construction Cape offers approximately 2,230 sq. ft. of finished living space across three levels with 3 bedrooms and 2.5 baths. The main level features an expansive wraparound kitchen, sliders leading to the back deck, and two separate living spaces that can easily adapt to your lifestyle. Create an eat-in kitchen with two living areas, a living room and den, or use one as a spacious formal dining room. A convenient half bath and laundry room complete the first floor. Upstairs are two generous bedrooms, a full bath, and a spacious primary suite with its own private bath and walk-in closet. The finished walkout lower level adds even more flexibility for a family room, home office, gym, hobbies, or additional recreation space and connects directly to the one-car under-house garage. Outside, the private backyard is surrounded by mature trees with a level, open area offering plenty of room for entertaining, gardening, play, or simply relaxing outdoors. The home is nearing its completion, giving you the opportunity to be its very first owner and enjoy all the benefits of new construction without starting from scratch. A great combination of space, privacy, flexibility, and lake-community living! Lake rights and fully recreational amenities offered by Bunggee Lake, including boating, fishing, and swimming opportunities.

61 Red Cedar Rd, Woodstock

$650,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24197102 MLS

This 4-bedroom, 2591sqft Cape is on cul-de-sac, conveniently located in South Woodstock. Offering combination of classic character with hardwood floors and comfortable living spaces, this single owner home is ready for it's next chapter. The main level living area is all hardwoods, with a kitchen/dining combination, a living room with a propane fireplace, and an office with tons of built-ins. Come in from the garage that is equipped with shelving and a set tub, to the mudroom with open locker style storage. Privately tucked to the rear of the main floor is the primary suite, with a large walk in closet, and full bath. The 2nd level is a surprise with 3 good sized bedrooms, a full bath, a great closet storage space, and a future living space, already studded with rough plumbing and electric. The level back yard offers room to relax, play, garden, or entertain. The irrigation system will keep the lawn green. No HOA, Senexet Village Road is town owned, and also hosts a recreation area for all to use.

23 Senexet Village Rd, Woodstock

$2,500,000

3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24196666 MLS

Welcome to this 80 acre Connecticut Estate, tucked into the rolling hills of Woodstock Ct. This exceptional 4,655 sq ft contemporary home offers a unique living experience with its own privately owned public FAA approved commercial grade airport. The property is a pilot's paradise, featuring a spacious hangar that not only accommodates multiple small planes and helicopters but also offers ample room for vehicle storage. The hangar is self-sufficient with its own septic, well, electrical, and heating systems, providing convenience and flexibility as well as a finished lounge area to gather and relax. This property is a rare find, offering a blend of luxury, functionality, and the ultimate in private aviation convenience! Whether you're an avid pilot, car enthusiast, or simply seeking a tranquil retreat, this home promises an unparalleled lifestyle. This residence boasts privacy and scenic New England beauty with stunning views. The contemporary design, built in 1987, features 3 bedrooms and 4 bathrooms, open living space with soaring ceilings, two story fireplace, and a beautiful open center oak staircase. The home's large windows and open layout invite the natural surroundings inside, creating a harmonious living environment. The finished walkout lower level offers beautiful views of the pond and the plush grounds. So many exciting possibilities!

80 Bungay Hill Rd, Woodstock

$698,900

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24193568 MLS

Enjoy Lake Living in Woodstock's Quiet Corner at Quasset Lake! Welcome to this beautifully landscaped 2-3 bedroom, 2.5-bath home in the desirable Quasset Lake community, where lake living and year-round recreation await. Located directly across the street from the association's private boat launch and deeded lake/beach access, you'll enjoy convenient access to swimming, boating, kayaking, and fishing just steps from your front door. Designed for both everyday living and entertaining, the open-concept main level features a gourmet kitchen with a center island, fixed breakfast bar, and seamless flow into the dining area and family room. A stunning floor-to-ceiling, double-sided fireplace creates a warm and inviting atmosphere, serving both the family room and the first-floor primary suite. The spacious primary bedroom includes a full en-suite bath and a private sauna and standup tanning booth, offering the perfect retreat after a day on the lake.

20 Loyola Rd, Woodstock

$74,999

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24193441 MLS

Welcome to your summer "Home away from Home" Looking for your "Seasonal Home Away from Home" Look no further this cute as a button, privately situated park model. Fresh new updates and newly applied finishing touches, makes this unit able to just move on in and start enjoying the rest of the season. Just steps from the amenities. pool, pavilion, mini golf, cornhole field, basketball and short walk to the catch and release fishing pond. While also enjoying the tranquility of the home away from home feeling. This unit comes almost completely furnished.

25 Rte 197th Rte, Woodstock

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