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

$299,900

3 Beds ⋅ 1 Baths ⋅ 24214400 MLS

Welcome to 82 Little Pond Road in Woodstock, CT! This charming 3-bedroom, 1-bath ranch offers the convenience of single-level living on a .64-acre lot. With approximately 1,100 square feet of living space, this home features hardwood flooring, a cozy fireplace, and a functional floor plan. The full basement provides additional storage space and includes a one-car garage. Situated in a peaceful setting, the property offers a spacious yard with room to enjoy the outdoors. While the home could benefit from some updating and a little TLC, it presents a wonderful opportunity for buyers looking to add their personal touches and make it their own. With plenty of potential and a desirable Woodstock location, this property is ready for its next chapter. Bring your vision and explore the possibilities!

82 Little Pond Rd, Woodstock

$350,000

2 Beds ⋅ 1 Baths ⋅ 24214889 MLS

Charming Home on Beautiful Bungay Lake Experience the beauty of lakeside living in Connecticut's picturesque Quiet Corner! Welcome to this inviting and spacious 2-bedroom ranch, nestled in the beautiful town of Woodstock, Connecticut, along the desirable Bungay Lake. Whether you're searching for a peaceful year-round residence, a relaxing weekend retreat, or the perfect place to enjoy all four New England seasons, this property offers a wonderful opportunity to embrace the lake lifestyle. Step inside and discover a warm, welcoming home featuring convenient one-level living. The main floor offers two generously sized bedrooms, a full bathroom, a spacious living room, and a comfortable kitchen, providing plenty of room for everyday living and entertaining. The expansive lower level presents incredible potential for additional living space! With its generous size and convenient walkout access, this area offers endless possibilities for a future in-law suite, guest accommodations, recreation room, home office, or additional finished living area. Outside, enjoy the privacy of your own yard and driveway, creating a peaceful setting to relax, entertain, or simply appreciate the natural beauty surrounding you. Imagine experiencing all four seasons in this beautiful lakeside community - warm summer days enjoying the lake, breathtaking autumn foliage, peaceful winter scenery, and the refreshing beauty of spring. Located in Woodstock, one of

30 Hilltop Dr, Woodstock

$490,000

3 Beds ⋅ 2 Baths ⋅ 24214001 MLS

SOLAR PAID OFF AT CLOSING! Move in with solar working to keep your electric bills low from day one! This updated colonial sits on a peaceful acre on a quiet cul-de-sac in sought-after Woodstock, and the BIG-TICKET items are done: brand new roof and siding, new hot water heater, water filtration system, new washer and dryer, and a freshly painted back deck overlooking the yard and the above ground pool. The hard work is done and the peace of mind is included; all that's left is to make it your own. Enter through the new mudroom to a bright living room, separate dining room, and a kitchen with granite counters, stainless appliances and a breakfast bar. Off the kitchen, the bonus room with a pellet stove is ready for whatever you need: home office, guest space, or den. Right next to it, the laundry room includes a second shower and sink, with the half bath just down the hall. Upstairs, the primary bedroom has a walk-in closet, plus two more bedrooms and a full bath with a brand new double vanity. Generator ready, with a 2-car attached garage. Minutes from Woodstock Academy, scenic Route 169, local farms, orchards and the Woodstock Fairgrounds, with easy access to I-395 and Massachusetts.

21 Fairfield Dr, Woodstock

$369,000

3 Beds ⋅ 1 Baths ⋅ 24187880 MLS

A little charm, a lot of heart, and a location worth getting excited about! Nestled in Woodstock with deeded rights and beach access to highly sought-after Witches Woods Lake, this inviting 3-bedroom, 1-bath ranch offers comfort, warmth, and the ease of one-level living. The home has been lovingly maintained and thoughtfully updated, including a kitchen remodel in 2023 with new cabinets, appliances, and flooring, offering a fresh and functional space for everyday living. The spacious deck is a wonderful place to enjoy morning coffee, gather with friends, or simply unwind. Downstairs, the finished lower level offers a cozy rec room and dedicated office area, providing extra space to make your own. Improvements over the years include a roof in 2018, water heater in 2021, interior and exterior doors in 2023, and well tank and well cap in 2024. Filled with warmth, character, and pride of ownership, this inviting home is ready for its next chapter and someone new to make it their own.

1629 Rte 171, Woodstock

$339,900

4 Beds ⋅ 2 Baths ⋅ 24212685 MLS

What started as just a summer cottage has been transformed over the 50 years of ownership into a great lake view & access home. This home features over 1,700 sq. ft. on two floors, 4 total bedrooms along with 2 full bathrooms. The first floor has a large living room with pellet stove heating that satisfies the major of the heating needs. There is a good working space kitchen along with a rear sunroom/plant room/dining area. There are two bedrooms, a full bathroom with tub/shower along with the laundry on the main level. The second floor was a full addition years ago. There are two very good-sized bedrooms, a sitting area/den, along with an additional full bathroom. You will even find a second story open deck for enjoying nature. Home features a full walk-up attic with good access & storage. The basement, once just a small crawl space, was excavated out and a block foundation was installed. A propane warm air heating system, propane water heater, along with an additional chimney flue for woodstove can be found. Home has deeded access & lake rights to Lake Bungee and is just walking distance from private beaches and boat launches.

101 Beaver Dam Rd, Woodstock

$499,900

6 Beds ⋅ 3 Baths ⋅ 24212211 MLS

Beautifully charming and beaming with character is this very spacious 2-family duplex; a rare find in Woodstock! This home is not your typical duplex and has a great floor plan in each unit. Perfect for an owner that wants to occupy a lovely home in a great location. Also nice for investors because the nicely updated and generously-sized units, each with their own laundry on the main floors, brings a higher rental income! The very large main house has attractive character, 4 large bedrooms, 2 full bathrooms, a dreamy updated kitchen with open floor plan to living room and dining areas. A first floor 4th bedroom and a laundry room on the main floor is large enough to be a 5th bedroom or office space! The second floor has three large bedrooms and a very large open den/craft room/office/home or college school area and a 2nd full bath! This unit has more space than you can dream to fill! The second unit is also generously-sized and nicely updated with 2 large bedrooms and a laundry room large enough to be a 3rd bedroom or office. Large living room leads to the updated open kitchen with an island and separate dining room. The home has a 3-car detached garage and peacefully landscaped grounds with room to garden. All separate utilities. Well water and public sewer. Listing Agent related to Seller. Come see this hidden gem before its gone!

9 Ellen Ln, Woodstock

$379,900

3 Beds ⋅ 2 Baths ⋅ 24211726 MLS

If you're looking for a place to be surrounded in all that nature has to offer, you'll want to call this home! This 3 bedroom, 2 bath, saltbox colonial is sited on a double lot, bordering Wyndham Land Trust. You'll love watching the deer and other wildlife from the 10'x20' deck. As a part of the private community of Lake Bunggee, you may also take a short stroll to the beaches to enjoy water rights and access. The lake is about 112 acres to enjoy boating, fishing, swimming and hiking areas. The light filled, open floor plan is perfect for entertaining; vaulted ceiling living room/dining area has hardwood flooring, an expansive wall of windows, and slider open to deck. Tiled kitchen has cozy breakfast bar and spacious walk-in pantry. 1st floor bedroom has ensuite bath with shower. 2nd floor primary also has ensuite bath with tub/shower unit and walk-in closet. Additional bedroom on second floor. Walk-out lower level has wood stove. Updates include newer hot water tank, septic system, and oil tank. Roof shingles 2015. Welcome Home!

35 Old Sawmill Rd, Woodstock

$85,000

24210559 MLS

What could you build on Lot 4 at Aplin Hill? We've already started imagining the possibilities. This .88-acre homesite is tucked within a thoughtfully planned Woodstock subdivision, with conservation land along the northern and eastern boundaries providing a natural buffer. A local builder has developed a proposed home design with this lot in mind, giving buyers a great starting point for seeing what could take shape here. The rendering and floor plan are conceptual and can be modified, or buyers are welcome to bring their own plans and builder. For buyers who prefer a more streamlined path to building, the proposed builder package takes much of the guesswork out of the process. The builder's estimated price includes construction of the home, site work, septic, well and driveway. Current builder pricing, specifications and details of what is included are available upon request. Aplin Hill features just 10 homesites across 29 acres, with approximately 18 acres preserved as permanent open space. Infrastructure includes a town road, walking path, underground power at the street and hydrant. Architectural guidelines help maintain the character of the neighborhood, where newer homes have recently been completed on neighboring lots.

Aplin Hill Ln, Woodstock

$779,000

5 Beds ⋅ 4 Baths ⋅ 24209434 MLS

Set high on historic Woodstock Hill, this distinctive 19th-century property offers a rare combination of history, character, exceptional views, flexible living spaces, guest accommodations, gardens, and opportunity. Offering approximately 2,500 square feet, this beautifully maintained home features five bedrooms and three-and-a-half baths, along with multiple living areas and a beautiful sitting porch overlooking the surrounding landscape. The home has been thoughtfully adapted to accommodate both private living and hospitality, creating flexibility for a variety of lifestyles. Two separate, thoughtfully furnished guest suites provide an established short-term rental opportunity and have enjoyed strong bookings. Guests have included parents visiting their children attending Woodstock Academy and Pomfret School, families attending weddings and local events, and visitors seeking to experience the beauty and charm of Woodstock. The grounds offer another exceptional dimension. Flower-growing areas, gardens, and a flower stand have been developed by the current owners during their first year on the property, building upon their longstanding experience with gardening and growing. The property offers an exciting opportunity to continue and expand the flower-growing vision, create a garden-based business, or explore the possibility of a future studio or shop, subject to applicable approvals.

500 Rte 169, Woodstock

$379,000

3 Beds ⋅ 2 Baths ⋅ 24209276 MLS

Move in ready ranch offering updated one level living, a finished walkout basement, and a private, level yard, all in the desirable town of Woodstock! The open concept main floor features hardwood floors, abundant natural light, and an updated kitchen with upgraded cabinetry, countertops, center island, and eat-in area. The kitchen opens to the living room, creating an inviting space for everyday living and entertaining. Three spacious bedrooms and an updated full bath complete the first floor. The finished lower level adds flexible living space with an open layout, pellet stove, walkout access, half bath, and laundry room. This space is ideal for a family room, home office, recreation space, or guest area. Outside, enjoy the spacious deck overlooking the private yard, plus a storage shed. Set in a quiet Woodstock location with easy access to 395 and 84, this home is convenient to major routes and surrounding communities. An affordable opportunity to enjoy the charm of Woodstock with updates already in place. Nothing to do but move in!

1619 Rte 171, Woodstock

$339,900

3 Beds ⋅ 2 Baths ⋅ 24205731 MLS

WAKE UP TO THE LAKE AND LIVE THE LAKE LIFE! Welcome to 91 Beaver Dam Rd, where everyday living feels like a getaway. This inviting 3-bedroom, 2-bath home is ideally situated across the road from the beach, putting swimming, fishing, kayaking, and canoeing practically at your doorstep. Imagine starting your morning with a beautiful sunrise over the lake, enjoying your coffee, then heading out for a paddle or some of the area's great fishing. Take a leisurely walk along the quiet community roads, meet your neighbors, and enjoy the relaxed atmosphere of this wonderful lake neighborhood. Whether you're searching for a year-round home, a weekend escape, or a place where you and friends can gather and make lasting memories, this property offers the lifestyle you've been looking for. Spend your days on the water, enjoy peaceful evenings, and leave the hustle and bustle behind. This isn't just a home-it's an opportunity to own a piece of the lake lifestyle.

91 Beaver Dam Rd, Woodstock

$1,425,000

4 Beds ⋅ 5 Baths ⋅ 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.

329 Rte 198, Woodstock

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Woodstock Real Estate

Newest Listings in Woodstock

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