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158 W Quasset Rd, Woodstock
$1,995,000
4 Beds ⋅ 4 Baths ⋅ 24180508 MLS
Extraordinary Waterfront Estate. Set on an exceptional 5.5-acre private lot with 265 feet of shoreline frontage, this completely rebuilt luxury residence offers a rare opportunity to own one of Woodstock's premier lakefront properties. Arrive via a long, newly paved private driveway that winds through a tranquil setting before revealing this stunning waterfront retreat. Offering 3,971 square feet, 4 bedrooms, and 4 bathrooms, the home was rebuilt from the ground up with next level quality and craftsmanship. Designed for both elegant entertaining and everyday enjoyment, the layout includes a formal dining room, spacious family room, custom mudroom, and a beautiful living room with propane fireplace overlooking Quasset Lake. The showpiece kitchen is truly one-of-a-kind, featuring handcrafted cabinetry by a New York artisan cabinet maker, thick quartzite countertops, premium built-in appliances, and a dramatic tray ceiling with custom white oak detailing. Luxury finishes continue throughout with veneer plaster walls, custom white oak vanities, a professionally designed primary closet, handmade laundry room cabinetry, and architectural flangeless LED lighting seamlessly integrated into the wood ceilings. Built with 2x6 construction, engineered floor systems, 2x12 roof rafters, red cedar siding and trim, central air, all-new heating and cooling systems, underground 400-amp service, and an automatic whole-house generator. Step outside and embrace the ultimate lake lifestyle.

158 W Quasset Rd, Woodstock

1374 Rte 171, Woodstock
$1,299,000
4 Beds ⋅ 6 Baths ⋅ 24177811 MLS
Set on 10.3 private acres in desirable Woodstock Valley, Blue Heron Glade offers exceptional privacy, natural beauty and remarkable versatility. A long private drive crosses a cobblestone bridge and opens to a peaceful setting surrounded by stone walls, mature landscaping, abundant wildlife and a large private pond regularly visited by blue herons. More than 6,000 SF of finished living space is thoughtfully arranged into distinct areas for gathering, working, entertaining and retreating, allowing the home to adapt to many different lifestyles. The attached guest/in-law suite lives almost like a home of its own, with a bedroom, full bath, kitchen, loft/office and new white oak flooring. The finished lower level adds a custom speakeasy-style bar, theater and additional flexible rooms. Outdoors, enjoy a fenced inground pool and substantial pool house with granite counters, half bath and outdoor shower. Four oversized garage bays, unfinished loft space and high-speed fiber internet add even more versatility to this remarkable property.

1374 Rte 171, Woodstock

00 Ide Perrin Rd, Woodstock
$299,900
24174800 MLS
On a private road surrounded by unspoiled natural beauty, this remarkable 79-acre property offers exceptional privacy and endless potential. Two brooks enhance the landscape - Lebanon Brook along the western boundary and Porter Pond Brook to the east. The land features a mix of wetlands and highlands, heavily wooded with abundant timber resources. Create your secluded homestead in the wilderness among other large-acreage parcels, with enough lumber to build and heat your home for years to come. The property includes approximately 300 feet of road frontage on Ide Perrin Road, 1,143 feet of frontage on Pole Bridge Road, and 416 feet of frontage by right-of-way. Please do not walk the property without your Realtor present.

00 Ide Perrin Rd, Woodstock

155 Paine Rd, Woodstock
$1,650,000
4 Beds ⋅ 6 Baths ⋅ 24174159 MLS
Set on a breathtaking stretch of rolling countryside in historic Woodstock, this extraordinary Federal Colonial reproduction blends timeless New England craftsmanship with modern luxury across a remarkable multi-parcel estate. Approached by a long winding driveway, the home is perfectly positioned to capture sweeping pastoral views, overlooking fenced fields, hay meadows, and distant farmsteads. Designed with exceptional attention to detail, the residence features a handcrafted artisan kitchen with Wolf and Sub-Zero appliances, soapstone and marble countertops, cooling drawers, wine chillers, and sun-filled gathering spaces framed by French doors and endless views. The home offers five Rumford fireplaces, luxurious bedroom suites each with private baths, a stunning primary suite with reading nook, spa-inspired bath, custom wardrobes, and private deck overlooking the heated gunite pool, pool house, stone patio, and outdoor fireplace. A dramatic central staircase leads through all three finished levels, including a third-floor bonus retreat with full bath, while an elegant private in-law suite offers its own entrance, living area, fireplace, and full bath and the home is geothermal. Complementing the property is a remarkable reconstructed 1800s post-and-beam barn featuring eight stalls, lofts, hay and equipment storage, paddocks, turnouts, hydrants, and 200-amp electrical service-ideal for equestrian use, entertaining, events, hobby farming, endless country living at its finest

155 Paine Rd, Woodstock

36 Olde Meadow Rd, Woodstock
$799,900
4 Beds ⋅ 3 Baths ⋅ 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

30 Crabtree Lane, Woodstock
$1,339,000
1409024 MLS
Abutting lot consisting of 3.18 acres included in the sale. Located in the Woodstock Industrial Park, this versatile 10,000 sq ft metal building offers endless possibilities for industrial, manufacturing, or storage use. The property features two overhead doors-one 14'x16' and one 12'x12'-providing easy access for large equipment or vehicles. Inside, the 18-foot ceiling height (to fans and lights) offers excellent vertical clearance, with 42-inch exterior doors. The building includes five restrooms, a mezzanine for added storage or office space, and is equipped with a brand-new, never-used oil furnace as well as an outdoor woodstove. With powerful 3-phase 220V, 400-amp service to both units, this property is ready to support high-demand operations. Situated in an industrial zone with room to expand, this is a prime opportunity for businesses looking to grow in a well-established location. Conveniently located just 29 miles to Worcester, 35 miles to Providence, and 47 miles to Hartford, with room to expand on-site, this is a smart opportunity in a well-established industrial zone. New roof!

30 Crabtree Lane, Woodstock

30 Crabtree Ln, Woodstock
$1,339,000
24164156 MLS
Abutting lot consisting of 3.18 acres included in the sale. Located in the Woodstock Industrial Park, this versatile 10,000 sq ft metal building offers endless possibilities for industrial, manufacturing, or storage use. The property features two overhead doors-one 14'x16' and one 12'x12'-providing easy access for large equipment or vehicles. Inside, the 18-foot ceiling height (to fans and lights) offers excellent vertical clearance, with 42-inch exterior doors. The building includes five restrooms, a mezzanine for added storage or office space, and is equipped with a brand-new, never-used oil furnace as well as an outdoor woodstove. With powerful 3-phase 220V, 400-amp service to both units, this property is ready to support high-demand operations. Situated in an industrial zone with room to expand, this is a prime opportunity for businesses looking to grow in a well-established location. Conveniently located just 29 miles to Worcester, 35 miles to Providence, and 47 miles to Hartford, with room to expand on-site, this is a smart opportunity in a well-established industrial zone. New roof!

30 Crabtree Ln, Woodstock

30 Crabtree Lane, Woodstock
$989,000
1403779 MLS
Located in the Woodstock Industrial Park, this versatile 10,000 sq ft metal building offers endless possibilities for industrial, manufacturing, or storage use. The property features two overhead doors-one 14'x16' and one 12'x12'-providing easy access for large equipment or vehicles. Inside, the 18-foot ceiling height (to fans and lights) offers excellent vertical clearance, with 42-inch exterior doors. The building includes five restrooms, a mezzanine for added storage or office space, and is equipped with a brand-new, never-used oil furnace as well as an outdoor woodstove. With powerful 3-phase 220V, 400-amp service to both units, this property is ready to support high-demand operations. Situated in an industrial zone with room to expand, this is a prime opportunity for businesses looking to grow in a well-established location. Conveniently located just 29 miles to Worcester, 35 miles to Providence, and 47 miles to Hartford, with room to expand on-site, this is a smart opportunity in a well-established industrial zone. New roof!

30 Crabtree Lane, Woodstock

1250 Rte 171, Woodstock
$245,000
3 Beds ⋅ 2 Baths ⋅ 24147222 MLS
Welcome to this charming colonial with stenciled details that add character & style! This delightful antique property is the perfect fixer upper and features 3 bedrooms, 1 and a 1/2 bathrooms, and a clapboard exterior. Situated on a 0.9 acre lot, this home boasts a garden in the side yard and a large backyard, perfect for outdoor enjoyment. Additionally, a shed provides convenient storage for your tools and equipment. As you step inside, the exterior mudroom/laundry area offers a practical entry point and as well as storage. The main level has a kitchen that has country charm and ample cabinets as well as a full bath with a tub. The living room and dining area are adorned with a traditional fireplace and woodstove, creating a warm and inviting atmosphere. The primary bedroom and a dedicated craft room complete this floor. Upstairs, two more bedrooms await, each offering its own unique charm. One of the bedrooms features an ensuite half bathroom and a walk-in closet and skylight, providing privacy and convenience. Don't miss the opportunity to make this house your home!

1250 Rte 171, Woodstock

1129 Rte 169, Woodstock
$1,350,000
170587074 MLS
Get ready to embark on an exciting opportunity with this licensed daycare facility! Boasting an impressive capacity for a total of 128 children, this conveniently located center is an ideal investment. Catering to families in the surrounding area, this facility has become a trusted hub for childcare. Situated within a charming rural location, this daycare facility offers a serene environment where children can learn, play, & grow. Picture rolling hills, fresh air, & plenty of space for outdoor activities. Parents will appreciate the peaceful surroundings, knowing their little ones are in safe hands. One of the many highlights of this daycare is its unique partnership with Woodstock Elementary School. With a before & after school capacity of 50 children, this facility provides seamless integration for families seeking comprehensive childcare solutions. Measuring 9425 square feet, this daycare facility provides a generous space for children to explore & engage in various educational activities. Equipped with all the necessary amenities, including play areas, classrooms, and restrooms, this facility is ready to accommodate the needs of growing families. Additionally there is a 1300 sq. ft. 3 Bedroom apartment on the property. Don't miss out on this incredible opportunity to own and operate a licensed daycare facility in an idyllic rural setting. Enquire today and embark on a rewarding journey of fostering a safe and nurturing environment for children to thrive in.

1129 Rte 169, Woodstock

848 Rte 171st Rte, Woodstock
$2,100,000
6 Baths ⋅ 24074696 MLS
Taylor Brooke Vineyard, Winery, Brewery, and Residence presents a rare opportunity to acquire 43 picturesque acres in Woodstock, Connecticut. This offering includes three distinct structures: a 7,122 GSF winery with a state-of-the-art wine-making facility layout, tasting pavilion, retail space, and cocktail bar; a 5,884 GSF brewery featuring a beer production facility layout, commercial kitchen, taproom, retail space, and outdoor patio; and a 2400 SF custom-built grand Cape residence. The sale encompasses (Real Estate Only) the vineyard(5.19 Acres of mature vines), winery, brewery, residence offered at $2,100,000. In addition to the Real Estate offering the business assets offering includes all equipment and furnishings $569,007 a current Product inventory. product recipes, wholesale distribution network, brand rights, goodwill and 80 hours of transitional operational consulting $230,993. Total turn-key offering with Real Estate, Business assets, product inventory and transitional consulting $2,900,000.

848 Rte 171st Rte, Woodstock

101 Child Hill Rd, Woodstock
$520,000
4 Beds ⋅ 3 Baths ⋅ 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

30 Crabtree Ln, Woodstock
$989,000
1 Baths ⋅ 24086817 MLS
Located in the Woodstock Industrial Park, this versatile 10,000 sq ft metal building offers endless possibilities for industrial, manufacturing, or storage use. The property features two overhead doors-one 14'x16' and one 12'x12'-providing easy access for large equipment or vehicles. Inside, the 18-foot ceiling height (to fans and lights) offers excellent vertical clearance, with 42-inch exterior doors. The building includes five restrooms, a mezzanine for added storage or office space, and is equipped with a brand-new, never-used oil furnace as well as an outdoor woodstove. With powerful 3-phase 220V, 400-amp service to both units, this property is ready to support high-demand operations. Situated in an industrial zone with room to expand, this is a prime opportunity for businesses looking to grow in a well-established location. Conveniently located just 29 miles to Worcester, 35 miles to Providence, and 47 miles to Hartford, with room to expand on-site, this is a smart opportunity in a well-established industrial zone. New roof!

30 Crabtree Ln, Woodstock

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