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$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

$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

$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

$479,900
3 Beds 2 Baths ACTIVE Status 24187904 MLS
Welcome home to this charming colonial tucked away on a peaceful cul-de-sac, offering privacy and picturesque views on a full acre of land. As you step in through the fresh new mudroom, you will find a spacious, bright living room, a separate dining room, and a beautiful kitchen with stainless steel appliances, a breakfast bar, abundant cabinet space, and access to a private back deck overlooking a scenic backyard and surrounding nature. Just off the kitchen, you will find a versatile bonus room currently used as a bedroom offering endless possibilities as a family room, home office, playroom or guest space. This area also features a wood stove, and a convenient laundry room complete with a bonus shower and sink. Upstairs the spacious primary bedroom includes a walk in closet, accompanied by two additional bedrooms and a full bath with a brand new double vanity. Major improvements provide added peace of mind, including a brand new roof and siding, water filtration system, new hot water heater, new washer and dryer, and leased solar panels for improved energy efficiency. A two car garage and beautiful natural surroundings complete this move in ready home in a highly desirable location.

21 Fairfield Dr, Woodstock

$799,900
4 Beds 3 Baths ACTIVE Status 24165439 MLS
TO BE CONSTRUCTED | Starting at $799,900 Welcome to Eastwood Estates, where luxury living meets the natural beauty and tranquility of Woodstock. Set on a picturesque 1.92-acre homesite bordering protected open space and framed by classic New England stone walls, this offering provides a rare opportunity to build a custom home in one of the area's most desirable neighborhoods. Partner with an experienced local builder to create a home that reflects your lifestyle and vision. Choose from thoughtfully designed plans, including a stunning Country Colonial featuring 4 bedrooms and 2.5 baths, or explore alternative layouts, or bring your own ideas to life within the builder's program. Each home is crafted with attention to detail, blending timeless elegance with modern functionality; open living spaces, quality finishes, and design flexibility suited for today's living. Eastwood Estates is governed by covenants that preserve the integrity and value of the neighborhood, including a minimum home size of 2,900 square feet (which may include finished lower-level space). Enjoy the peaceful charm of Woodstock with nearby access to local farms, walking trails, and scenic roads, while still being within reach of everyday conveniences and commuting routes. A unique opportunity to build a home that is both refined and personal, guided every step of the way.

36 Olde Meadow Rd, Woodstock

$520,000
4 Beds 3 Baths ACTIVE Status 24125003 MLS
Step back in time with this one-of-a-kind 1830 Greek Revival farmhouse, offering 2,150 sq ft of character and charm on a picturesque 0.90-acre lot surrounded by farm land. Just down the hill from historic Woodstock Hill and the Academy, this setting is as scenic as it is convenient. Inside, wide plank floors and distinctive windows frame beautiful country views, while the front entry showcases its original door with full exterior shutters, a hallmark of Greek Revival style. The living room centers on a classic fireplace, and along the upstairs landing a wall of built-in bookshelves creates a welcoming library space. Three bedrooms are located on the second floor, with an additional first-floor room currently serving as a fourth bedroom. The primary includes a walk-in closet and bath with a clawfoot tub. The walk-up attic offers potential for an office, playroom, or studio. The kitchen features a custom layout paired with quality appliances (Sub-Zero fridge & Thor cooktop) and the warmth of a wood stove. Updates include new Trex decking and a newly finished three-season room off the dining room. Historic touches, such as unique wallcoverings and original details, remain intact, blending history, artistry, and the timeless charm of living in Woodstock, CT. Property to be sold in as-is condition.

101 Child Hill Rd, Woodstock

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