Woodstock Real Estate

Woodstock Real Estate

Welcome to Woodstock, Connecticut, a charming town nestled in the picturesque Windham County. Known for its rich history and stunning natural landscapes, Woodstock offers a perfect blend of rural charm and modern conveniences, making it an ideal place to call home.

Founded in 1686, Woodstock boasts a vibrant heritage that is evident in its well-preserved architecture and historic sites. The town is home to several notable landmarks, including the iconic Roseland Cottage, a Gothic Revival masterpiece that draws history enthusiasts and visitors alike. The local community takes great pride in its heritage, often hosting events that celebrate the town's unique past.

Nature lovers will find Woodstock particularly appealing, with its expansive parks and nature reserves. The town is surrounded by lush forests, serene lakes, and scenic hiking trails, providing endless opportunities for outdoor recreation. Whether you enjoy a leisurely stroll through the picturesque countryside or an adventurous hike in the nearby woods, Woodstock offers an abundance of natural beauty to explore.

In addition to its scenic landscapes, Woodstock features a friendly, tight-knit community that fosters a welcoming atmosphere. The local farmers' market showcases fresh produce and artisanal goods, while quaint shops and cozy cafes line the charming streets, inviting residents and visitors to enjoy the small-town vibe.

With its perfect blend of history, nature, and community spirit, Woodstock, CT, is more than just a place to live—it's a lifestyle. Whether you're looking to settle down or simply explore, Woodstock promises a warm welcome and a wealth of experiences waiting to be discovered.

Newest Listings in Woodstock

$698,900
2 Beds ⋅ 3 Baths ⋅ 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
$260,000
2 Beds ⋅ 2 Baths ⋅ 24193406 MLS ⋅ Woodstock Meadows BLDG.
Tucked away in the sought-after Woodstock Meadows community, this beautifully maintained townhouse offers the perfect balance of comfort, convenience, and small-town charm. Opportunities to own in this desirable neighborhood are few and far between, making this an exceptional place to be home. Enjoy the best of Woodstock living with historic Roseland Park and Golf Course just moments away, where scenic walking trails, open green space, and year-round recreation are right at your fingertips. The surrounding neighborhood is peaceful and inviting, offering a quiet setting without sacrificing accessibility to local shops, dining, and everyday conveniences. Inside, this two-bedroom home offers 1,080 square feet of thoughtfully designed living space, complemented by an additional 264 square feet in the partially finished lower level-perfect for a family room, home office, fitness space, or hobby area. A one-car garage adds practicality and extra storage. Whether you're looking for your first home, downsizing, or searching for a low-maintenance lifestyle, this property delivers. The professionally managed homeowners association takes care of the exterior maintenance, allowing you to spend less time on upkeep and more time enjoying everything the area has to offer. With its desirable location, welcoming community, and easy living, 25 Woodstock Meadows is a place you'll be proud to be home.

25 Woodstock Mdws Unit 25, Woodstock
$75,000
2 Beds ⋅ 1 Baths ⋅ 24193441 MLS
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
$75,000
2 Beds ⋅ 1 Baths ⋅ 73552757 MLS
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 197 Unit 70, Woodstock
$650,000
2 Beds ⋅ 3 Baths ⋅ 24187780 MLS
Perfect Countryside Elegance. Welcome to 511 Perrin Road, an exceptional country estate gracefully set atop a private 3.5-acre hillside in scenic Woodstock. A long paved driveway winds through picturesque grounds to this beautifully crafted home, where timeless architecture meets modern efficiency with 100% owned solar. Designed for effortless one-floor living, the residence features a luxurious first-floor primary suite, private executive office, gleaming hardwood floors, exquisite custom built-ins, and an inviting open living and dining area anchored by a dramatic back to back wood-burning fireplace. The custom Brunarhans kitchen is a showcase of quality craftsmanship and thoughtful design. The home boasts 2,393 SqFt of finished living space with 2.5 baths. The second level offers a spacious guest bedroom, full bath, and a connected bonus room, providing exceptional flexibility for family and guests. Step outside to enjoy the serenity of the private patio, a charming pond, and sweeping open grounds. The expansive lawn offers outstanding potential for a boutique vineyard, gardens, or equestrian pursuits, with horses and household pets permitted and ample room for paddocks. Completing this remarkable property is an oversized two-car garage with a private workshop. A rare combination of privacy, elegance, sustainability, and refined country living. A truly exceptional offering in one of Woodstock's most desirable locations.

511 Perrin Rd, Woodstock
$629,900
4 Beds ⋅ 3 Baths ⋅ 24189890 MLS
Nestled on 12.78 acres in the beautiful countryside of Woodstock, this custom-built contemporary home offers 3,447 square feet of thoughtfully designed living space with 4 bedrooms and 3 baths. Built in 1980 and enhanced with a spacious primary suite addition in 2005, this home blends timeless character with modern updates. The first-floor primary suite is a true retreat, featuring its own cozy fireplace for year-round comfort. A second fireplace anchors the main living area, where soaring ceilings, abundant natural wood accents, and expansive windows create a warm and inviting atmosphere. Wood flooring complements the main living spaces, while wall-to-wall carpeting adds comfort to the bedrooms and select living areas. The kitchen features new appliances and opens to the home's generous living and entertaining spaces. An Andersen French door slider, installed in 2020, leads to a new deck overlooking the peaceful property. Enjoy the outdoors from the screened-in porch, perfect for relaxing or entertaining while taking in the surrounding natural beauty. Recent improvements include a new garage roof, a new deck, and a main house roof that is less than 15 years old, providing added peace of mind. A long driveway leads to the home and detached two-car garage, offering a picturesque approach. Located in one of Woodstock's most desirable areas, this exceptional property combines tranquil country living with convenient access to the Mass border, making it ideal for commuters

496 Center Rd, Woodstock
$300,000
24188739 MLS
22.2-acre building lot offering endless possibilities in desirable Woodstock! Whether you're a builder, investor, or looking for the perfect location to build your forever home, this property is ready for your vision. Approximately 0.5 acres have already been cleared, and valuable due diligence has been completed, including a town-approved septic design, engineered site plan, and professionally delineated and marked wetlands. Neighboring lots have been surveyed, adding to the property's appeal. Enjoy the privacy and beauty of country living with plenty of space for your dream home while remaining conveniently located near local amenities and major routes. A rare opportunity to own a large parcel with much of the groundwork already in place. Bring your plans and make your dream a reality!

Route 197 Route, Woodstock
$45,000
1 Beds ⋅ 1 Baths ⋅ 24188690 MLS
Welcome to Beautiful Meadowside of Woodstock Campground, a private, gated 100 site co-op campground in Connecticut's quiet Corner. Unit 29 features a 1998 Four Winds mobile home model 30fk and a 30 foot by 9.5 foot combination room added on to the front. The trailer has a kitchen, living room dining room combo with a pull out bed, full bath, and bed room. The addition had a bigger eating area and a family room. It is move in ready, fully furnished. Lot assessment of $1,650/ season (1,350 early-bird before Jan 31) covers water, sever, trash, grounds maintenance, and all amenities. Season runts from mid April through October

25 Rte 197 Rte Unit 29, Woodstock
$500,000
3 Beds ⋅ 2 Baths ⋅ 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
$74,900
24186921 MLS
Imagine waking each morning to shimmering lake views and the peaceful sounds of nature. Tucked away on a quiet dead-end road in Woodstock's coveted Quassett Lake community, this exceptional homesite offers the rare opportunity to create a custom retreat in one of northeastern Connecticut's most treasured settings. Perched above the road with a gentle rise in elevation, the property enjoys beautiful direct views of Quassett Lake, with the potential to enhance those vistas through selective tree clearing. Just a short stroll away, the neighborhood lake access invites you to spend your days swimming, kayaking, boating, fishing, or simply soaking in the tranquility of lakeside living. As a previously improved homesite, the property offers an existing well and prior septic area, creating a helpful foundation for buyers as they explore future building plans. A 2016 perc test and A-2 survey are also available, offering additional confidence as you begin planning your dream home. Whether you envision a timeless architectural masterpiece, a modern lakeside escape, or a peaceful year-round residence, this is a place where your vision can truly come to life. Opportunities to build with lake views in Quassett Lake are exceptionally rare- don't miss your chance to create something extraordinary!

182 Baxter Rd, Woodstock
$1,275,000
4 Beds ⋅ 4 Baths ⋅ 24185273 MLS
This extraordinary waterfront estate on Chamberlain Lake offers a lifestyle rarely found in Connecticut. With 200ft of private lake frontage, this custom post-and-beam Cape was thoughtfully crafted using timber milled directly from trees harvested on the property, creating a residence that is as authentic as it is remarkable. A dramatic center chimney anchors the home, while wide-board pine floors, exposed beams, and walls of windows showcase breathtaking views. The primary suite features a private balcony overlooking the lake, two walk-in closets, and a spa-like bath. Generously sized rooms and oversized step-in closets throughout the home provide exceptional comfort and storage. A private entrance way will lead you to the lake to enjoy fishing, kayaking, canoeing, swimming and peaceful lake living await. Gather around the fire pits, enjoy the outdoor shower after a day on the water, or simply relax on the covered deck among professionally landscaped grounds. This exceptional property combines privacy, craftsmanship, recreation, and timeless New England beauty in one truly unforgettable offering.

95 Pole Bridge Rd, Woodstock
$290,000
2 Beds ⋅ 2 Baths ⋅ 24183795 MLS
Welcome to this beautiful lakeside retreat, ideally situated just a short walk from the private beach at Lake Bungee. Offering comfortable one-level living, this home features 2 bedrooms, one being a primary suite with a private bath and relaxing Jacuzzi tub. The bright and inviting floor plan includes a sun-filled sunroom, perfect for enjoying morning coffee or unwinding at the end of the day. This home also has a second full bathroom, open kitchen with bar style seating. Step outside to a spacious deck overlooking the oversized lot, offering plenty of room for entertaining, gardening, or simply enjoying the outdoors. Car enthusiasts and hobbyists will appreciate the oversized attached two-car garage with ample storage space. Whether you're looking for a year-round residence or a peaceful get away near the lake, this charming property combines comfort, convenience, and a desirable location with private beach access just moments away. Home is being sold in AS-IS condition

60 Lyon Rd, Woodstock
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