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

$199,900

1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24217258 MLS ⋅ Woodstock Meadows BLDG.

Welcome to Woodstock Meadows! This charming ranch-style, 1-bedroom, 1-bath condominium offers convenient single-level living with the added bonus of finished space in the lower level. The main living area features a comfortable and functional layout, while the finished bonus room in the basement provides flexible space ideal for a home office, hobby room, or additional living area. With some updating and your personal touches, this condo has the potential to truly shine! Whether you're a first-time buyer, looking to downsize, or simply seeking a more manageable living space, this property offers a wonderful opportunity to make it your own. Enjoy the charm of Woodstock and the convenience of nearby shopping, dining, and local amenities. Bring your vision and discover the possibilities this home has to offer!

39 Woodstock Mdws Unit 39, Woodstock

$445,000

3 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24217202 MLS

Experience the beauty of Bungee Lake living in this inviting Cape, where charm, comfort, and the beauty come together! This beautifully maintained, move-in ready home offers three bedrooms, two full bathrooms, and an inviting open floor plan designed for comfortable everyday living and effortless entertaining. The kitchen features beautiful granite countertops and stainless steal appliances, and flows seamlessly into the living areas, creating a bright and welcoming atmosphere. Step outside onto the gorgeous porch, the perfect spot to enjoy your morning coffee, unwind after a long day, or simply take in the surroundings and peaceful view of the lake. If you're looking for additional space, the walkout basement complete with a pellet stove offers wonderful potential for future finished living space, whether you envision a family room, home office, gym, or entertainment area. Additional features include a water softener, water purification system, and two outdoor sheds, offering plenty of storage. Located in the desirable Bungee Lake community, this home offers the opportunity to enjoy the charm and tranquility of lake life living, beautifully maintained, thoughtfully, equipped, and truly move in ready. Just unpack, settle in, and start enjoying everything this wonderful Home has to offer!

65 Hemlock Dr, Woodstock

$735,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24215553 MLS

Some homes just feel like home the moment you arrive, and 48 May Brook Road is one of them! Nestled in one of Woodstock's most desirable neighborhoods, this charming Colonial offers 3,537 square feet of thoughtfully designed living space, picturesque views, and sunsets you'll never grow tired of. A welcoming farmer's porch sets the tone, while the beautifully maintained grounds create an unforgettable first impression. Inside, the main level features an open-concept kitchen with walk-in pantry, dedicated dining area, two spacious living areas including one with a cozy gas fireplace, a private home office, and convenient first-floor laundry. Upstairs, you'll find four generously sized bedrooms and two full bathrooms. The finished walkout lower level offers incredible flexibility with an additional bedroom, full bathroom, media room with equipment included, ample storage, and potential in-law accommodations! Step outside to enjoy the expansive deck overlooking Connecticut's Quiet Corner, beautifully manicured grounds, a storage shed, and even a batting cage! Located within the Woodstock school district, this property offers the perfect combination of comfort, space, and New England charm. Homes like this don't come around often.

48 May Brk, Woodstock

$299,900

3 Beds ⋅ 1 Baths ⋅ COMING SOON Status ⋅ 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 ⋅ ACTIVE Status ⋅ 24214889 MLS

Charming Home on Beautiful Bunggee 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 Bunggee 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

$470,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24214001 MLS

$10,000 BUYER CREDIT! The seller is offering a $10,000 buyer credit to make this move-in ready house even easier to own. Use the credit to buy down your interest rate or help cover closing costs. 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, solar keeping electric bills low, 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

$329,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

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Woodstock Real Estate

Newest Listings in Woodstock

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