Woodstock Homes for Sale

Welcome to Woodstock, Connecticut—a charming town nestled in the scenic hills of Windham County. Known for its rich history and picturesque landscapes, Woodstock offers a unique blend of rural tranquility and community spirit, making it an ideal place for families, retirees, and anyone seeking a peaceful lifestyle. With its quaint New England charm, Woodstock is dotted with historic homes, lush green spaces, and vibrant local businesses.

As you explore the area, you’ll discover a wealth of outdoor activities, from hiking the beautiful trails of the nearby Mashamoquet Brook State Park to enjoying a leisurely afternoon at the charming local farms. The town hosts numerous community events throughout the year, fostering a sense of belonging and connection among residents.

For those considering a move to this idyllic town, there are a variety of homes for sale that cater to diverse tastes and budgets. Whether you’re looking for a cozy cottage, a spacious family home, or a luxurious estate, Woodstock’s real estate market has something for everyone. Many properties boast stunning views, ample outdoor space, and modern amenities while retaining that classic New England charm.

With its strong sense of community, excellent schools, and proximity to major highways, Woodstock is not just a place to live; it’s a place to thrive. Don’t miss the opportunity to make this enchanting town your new home. Explore the homes for sale in Woodstock today and discover the perfect blend of comfort and charm in this hidden gem of Connecticut!

Newest Woodstock Homes for Sale

$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.

Woodstock

$399,900

3 Beds ⋅ 1 Baths ⋅ 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 ⋅ 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 ⋅ 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

$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

$679,000

4 Beds ⋅ 3 Baths ⋅ 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 ⋅ 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 ⋅ 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

$415,000

3 Beds ⋅ 2 Baths ⋅ 24203168 MLS

OFFERS DUE BY TUE 9/8 AT 12 PM PLEASE. Deeded rights to the Bungee Lake community add something special to this charming Woodstock Cape, with a private, beautifully landscaped yard that makes you want to stay awhile. Mature landscaping surrounds the home with storybook charm, while a garden, patio and wonderfully usable backyard create plenty of space to enjoy your best life. Inside, the layout offers flexibility with three bedrooms, including a main-level bedroom with its own full bath and laundry setup, plus a second full bath upstairs. Additional finished space in the lower level gives you even more room to fit the needs of your life. Central air, 200-amp electrical service and an attached two-car garage add the practical comforts, while the adorable cupola perched above it all is the kind of detail that makes this home memorable. Private, charming and refreshingly easy to love- this one just feels like home.

55 Pine Grove Rd, Woodstock

$549,900

3 Beds ⋅ 3 Baths ⋅ 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

$250,000

3 Beds ⋅ 2 Baths ⋅ 24182428 MLS

Welcome to 721 Route 169, a hidden retreat nestled on nearly 5 wooded acres in the heart of scenic Woodstock. Surrounded by mature trees and nature in every direction, this Ranch style home offers the perfect opportunity for investors, renovators, or buyers ready to create their own private escape. Inside, you'll find three bedrooms, one and a half baths, hardwood floors in the bedrooms, a spacious layout, and a charming screened porch where you can relax and enjoy the peaceful surroundings. The full basement provides additional storage, while the level lot offers endless possibilities for gardens, recreation, or future outdoor living. Bring your vision and imagination to unlock this property's full potential.This rare offering combines privacy, acreage, and opportunity in one of Northeastern Connecticut's most desirable rural settings.

721 Rte 169, Woodstock

$650,000

4 Beds ⋅ 3 Baths ⋅ 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

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