Woodstock Real Estate

Woodstock Real Estate

Welcome to Woodstock, Connecticut – a charming town nestled in the heart of Windham County, where picturesque landscapes and rich history come together to create a unique living experience. With its serene ambiance and tight-knit community, Woodstock offers a perfect blend of rural charm and modern conveniences.

As you stroll through the scenic streets of Woodstock, you'll be captivated by its beautifully preserved architecture and lush green spaces. The town is home to a variety of historic landmarks, including the iconic Woodstock Academy, which has been serving the community since 1801. The vibrant arts scene is another highlight, with local galleries and studios showcasing the talents of resident artists.

Nature enthusiasts will find plenty to love in Woodstock. The town is surrounded by stunning natural beauty, with numerous parks, hiking trails, and tranquil lakes. The nearby Mashamoquet Brook State Park offers a perfect escape for outdoor activities, including hiking, fishing, and picnicking amidst nature’s splendor.

Families will appreciate the town’s excellent school system and community-oriented atmosphere, making Woodstock an ideal place to raise children. The local farmers' markets and seasonal events foster a sense of belonging, where neighbors come together to celebrate and support one another.

Conveniently located just a short drive from major highways, Woodstock provides easy access to nearby cities while maintaining its peaceful, rural charm. Whether you’re looking for a cozy cottage or a spacious family home, Woodstock has something to offer everyone. Come discover the enchanting lifestyle that awaits you in this idyllic New England town!

Newest Listings in Woodstock

$299,900
3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24194134 MLS
Adorable ranch located in desirable Woodstock, Connecticut! Offering over 1,200 square feet of comfortable one-level living, this charming home features three spacious bedrooms and one full bath. The updated eat-in kitchen opens directly to a bright three-season room, creating the perfect space to enjoy your morning coffee, relax, or entertain guests. The large living room features beautiful windows that fill the space with natural light, along with a convenient storage closet. The generously sized primary bedroom offers two walk-in closets, providing plenty of storage. A standout feature of this property is the oversized two-car attached garage, complete with high ceilings and ample room for vehicles, a workshop, additional storage, or the possibility of creating overhead loft space. Nestled on a peaceful half-acre lot, the property is surrounded by classic New England stone walls and mature trees that provide plenty of shade and privacy. This home offers a wonderful opportunity for buyers looking to add their own personal touches. While some updating and improvements may be desired, the property provides a functional layout, and plenty of potential to create a space that truly feels like home. This inviting Woodstock ranch is ready for its next owner to make it their own! Property is being sold as is where is. Highest and best due 07/28/2026 by 9 pm.

176 Joy Rd, Woodstock
$698,900
2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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
$650,000
2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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
$625,000
1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24191228 MLS
This lakeside escape was completely redone in 2023. This beautifully updated 1-bedroom, 1-bath year-round home is nestled on the shores of private Quasset Lake in Woodstock. This direct waterfront property is an absolute paradise for entertaining, boating, water skiing, and fishing. Step inside to a bright interior that has been freshly painted top to bottom in a neutral color palette. The entire home boasts brand-new wall-to-wall tile flooring with radiant heat that combines luxury with a high-durability lake-life utility. The open-concept layout flows seamlessly into a sunlit living space. Mini splits that provide heat and A/C and a newly installed gas fireplace designed to keep you cozy throughout the seasons. Exit through your sliders to your 19 x 33 outdoor high-end deck that extends your living space. It features motorized adjustable louvers that can be closed for complete shade or weather protection, as well as electric screens for insect protection.

4 Loyola Rd Extension, Woodstock
$279,000
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24189592 MLS
Summer isn't over yet-there's still time to own your own slice of paradise at beautiful Lake Bungee! Nestled just a one-minute walk from the water, this charming retreat offers the perfect blend of relaxation and recreation. Step outside to a private backyard oasis designed for making memories, featuring a spacious patio, cozy fire pit, and plenty of room to entertain family and friends under the stars. Inside, you'll find a bright, open-concept living space that feels warm and inviting, along with two comfortable bedrooms and a full bathroom. Whether you're looking for a peaceful weekend getaway, a seasonal escape, or a year-round home, this property is ready for you to start enjoying the lake lifestyle. Don't miss your opportunity to make every season feel like a vacation at Lake Bungee!

170 Laurel Hill Dr, Woodstock
$300,000
ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ 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
$74,900
ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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
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