Woodstock Real Estate

Welcome to Woodstock, Connecticut, a charming town nestled in the picturesque Windham County. With its rich history, stunning landscapes, and a tight-knit community, Woodstock offers a unique blend of rural tranquility and modern conveniences, making it an ideal place to call home.

Founded in the 18th century, Woodstock is steeped in history, with several well-preserved buildings and landmarks that tell the story of its past. Stroll through the quaint streets lined with colonial-style homes, or visit the iconic Woodstock Academy, one of the oldest private schools in the nation. The town’s vibrant cultural scene is complemented by annual events, including the famous Woodstock Fair, where residents and visitors alike gather to celebrate local traditions, crafts, and agriculture.

Nature enthusiasts will find Woodstock to be a haven for outdoor activities. The town is surrounded by lush forests, rolling hills, and serene lakes, perfect for hiking, fishing, and birdwatching. The nearby Mashamoquet Brook State Park offers miles of trails, picnic areas, and the tranquil beauty of nature, inviting you to explore and unwind.

In addition to its natural beauty, Woodstock boasts a friendly community with top-rated schools, local shops, and delightful eateries that showcase the best of New England cuisine. Whether you’re looking for a peaceful retreat or an active lifestyle, Woodstock has something to offer everyone.

Discover the charm of Woodstock, CT, where history meets nature, and a vibrant community awaits you. Come and explore the possibilities of making this enchanting town your new home!

Newest Listings in 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 road from Woodstock Academy and 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

$509,000

3 Beds ⋅ 2 Baths ⋅ 24204065 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 spacious garage includes a workshop area and storage loft. If you think this property looks pretty now, just imagine it with the bloom of foliage. Act now and you can be moved in by peak leaf season, your pumpkins and scarecrow await!

15 Paine District 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. 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

$125,000

24202057 MLS

Woodstock 13.60-Acre Residential Home Lot With 643-FT Frontage. Soil Testing, Perc Test Done. Septic Design / Engineering Done Approved. Proposed Site Plan With 4-Bedroom, 2-Car Attached Garage, And Nice Size 30' X 40' Outbuilding / Shop / Detached Garage As Well Done And Ready To Go. Most Of The Property Frontage And Both Driveway Aprons Are On Rte-197 (Old Turnpike Rd) And Continues Onto Lyon Hill Rd. Property Is Located At The Intersection Of Rte-197 (Old Turnpike Rd), Center Road, And Lyon Hill Road, Woodstock. Across Road From Laurel Spring Farm, 866 Rte-197 (Old Turnpike Rd). Driveway Apron On Rte-197 (Old Turnpike Rd) Build Site Is Accessible, Cleared, Level, Open, Already Has Two Access Ways / Driveways. See MLS Attachments For Soil Testing Results, Perc Testing Results, Survey / Site Plan, Aerial Maps, Etc. Please Do Not Go On The Property Without An Appointment.

Lyon Hill Rd, Woodstock

$415,000

3 Beds ⋅ 2 Baths ⋅ 24203168 MLS

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

$199,900

2 Beds ⋅ 1 Baths ⋅ 24201823 MLS ⋅ Fawn Ridge BLDG.

Welcome to this beautifully renovated 832 sq. ft. end-unit condo in Woodstock, CT, offering an inviting opportunity to trade renting for owning and start building equity of your own. Freshly updated with new paint and flooring, this home provides a clean, comfortable setting that's ready for you to make your own. As an end unit, the home offers added privacy and a desirable layout. Whether you're a first-time homebuyer ready to take the next step or simply looking for an affordable way to put your monthly housing toward ownership, this condo is a smart place to begin. Enjoy the simplicity of condo living while taking advantage of all that charming Woodstock has to offer. Why keep paying rent when you can start building something of your own? Come see how easy homeownership can be!

12 Fawn Rdg Unit 12, 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

$289,900

2 Beds ⋅ 2 Baths ⋅ 24198944 MLS ⋅ Woodstock Meadows BLDG.

Charming Woodstock countryside condo privately set off the road with beautiful meadow views and a peaceful, natural setting. This inviting home offers easy, low-maintenance living with the exterior upkeep, lawn care, and snow removal handled by the association. The first floor features hardwood flooring, a spacious living room with a wood-burning fireplace and slate hearth, and a dining area conveniently located off the kitchen. A newer sliding door leads from the living room to the deck, creating an ideal spot to relax and enjoy the tranquil surroundings. Upstairs are two comfortable bedrooms, including the primary bedroom with double closets, with a full bath conveniently situated between them. There's plenty of storage with an additional large closet in the hallway. The finished lower level adds valuable living space with a cozy family room/den, carpeting, a large closet, and a slider leading to a patio and small fenced area. The lower level also includes a utility/laundry area with washer and dryer, utility tub, hot water heater, and a workshop area. Windows were replaced in 2009. Enjoy the best of the Woodstock countryside with nearby walking trails, Roseland Park, restaurants and Woodstock Golf Course. The condo association allows up to two pets. An appealing opportunity for those seeking an affordable home in a private setting without the maintenance responsibilities of a single-family property.

33 Woodstock Mdws Unit 33, 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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