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

$1,425,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 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.

Woodstock

$175,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24205739 MLS ⋅ Fawn Ridge BLDG.

Welcome to 4 Fawn Ridge in Woodstock! This inviting condo offers a wonderful opportunity to enjoy the ease and convenience of condo living in a peaceful setting. Featuring a functional layout with comfortable living spaces, this home provides a great foundation for its next owner. Offering a great opportunity to add your own personal touches, this condo has solid potential and is ready for its next owner to make it their own. Bring your ideas and vision to create a space that truly reflects your style. Enjoy the charm of Woodstock while remaining conveniently located near local amenities, shopping, dining, recreation, and major routes. Whether you're looking for your first home, downsizing, or simply searching for a low-maintenance lifestyle, this property is worth a look. Schedule your private showing today and come see the possibilities at 4 Fawn Ridge Rd! (Photos virtually enhanced and staged)

4 Fawn Rdg Unit 4, Woodstock

$399,900

3 Beds ⋅ 1 Baths ⋅ COMING SOON Status ⋅ 24205841 MLS

Discover the privacy and peaceful setting of this charming 1,334 sq. ft. ranch nestled on 2 level, wooded acres in beautiful Woodstock, conveniently located near the Massachusetts line. Built in 1973, this home offers 3 bedrooms, 1 full bath, and inviting spaces designed for comfortable everyday living. A standout feature is the wonderful four-season sunroom, complete with a woodstove, cathedral ceiling, and skylights-an ideal spot to enjoy the beauty of the surrounding property year-round. The living room features a fireplace with a wood insert, adding warmth and character to the home. All three bedrooms offer ceiling fans, and window A/C units provide seasonal cooling. The attached 2-car insulated garage includes electric, automatic garage door openers, and a convenient breezeway connecting directly to the house. For the car enthusiast, hobbyist, or additional storage needs, there is also a separate 3-car detached garage with electric, providing an abundance of workspace and parking. The completely fenced yard features sheep fencing and offers plenty of room for pets, gardening, or outdoor activities. A shed at the rear of the property also serves as a chicken coop, adding to the property's versatility and rural charm. Add'tl updates and features include 200-amp electrical service, a 2011 furnace, 2026 hot water system, and a 2023 well tank. A private, versatile property with plenty of garage space, usable acreage, and the peaceful Woodstock setting you've been looking for.

673 Brickyard Rd, Woodstock

$164,900

ACTIVE Status ⋅ 24205686 MLS

Out in the boonies! 22 acres on the discontinued portion of Pole Bridge Rd. Discontinued means legal access & legally buildable but access is for property owners only, no public access. Subdivisions are only allowed on town owned & maintained roads so this extremely unique area of 2,000+ acres loaded with wildlife galore will remain natural large parcels. The land is located on the right 1.5 miles north of RT 197 with approximately 1,030 feet of road frontage (flagged) and is 1/4 mile deep. There are 3 off the grid homes north of this property and the road is maintained by owners who own equipment that must get in and out for supplies. Old camp in disrepair needs roof, maybe frame and floor salvageable. Pond has dried up, appears dam needs work.

00 Pole Bridge Rd, Woodstock

$499,900

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24203840 MLS

To be built 7 room raised ranch in a cozy neighborhood in Woodstock, At this price, this home will go quick! You have time to make several customized selections. Located on a fairly level and private lot, Tayler Tr is a quiet 20 year old open space subdivision (all homes less 20 years old) located on the Union town line off Tayler Rd, of which the remaining 27.77 acres of the original 44 acres on Tayler Rd was donated to the Wyndham Land Trust. The 94 acres across the street on Tayler Rd (south side) was donated to Nature's Conservancy, so no other homes will ever be built on Tayler Rd. AI says 36 minutes to 1 College St, Worcester (Holy Cross) and 40 minutes to Hartford.

8-2 Tayler Trl, Woodstock

$299,900

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24204986 MLS

Charming one-owner ranch nestled on a quiet country road in Woodstock, close to the Massachusetts border. This sweet home offers easy one-level living with three bedrooms, a full bath, hardwood floors in the living room and bedrooms, plus a comfortable eat-in kitchen. Enjoy the outdoors from the back deck overlooking the property, with the added convenience of walk-out basement and detached two-car garage. The roof is approximately 10 years old and a newer septic system (2010), this well cared for home is ready for its next family to make it their own. A wonderful opportunity to enjoy the peace and quiet and all that Woodstock has to offer while remaining close to area amenities and the Massachusetts border.

652 Brickyard Rd, Woodstock

$125,000

ACTIVE Status ⋅ 24204756 MLS

Mamma Italia Ristorante - Business for Sale | Turnkey Restaurant Opportunity in Woodstock, CT! Here is an opportunity to take over an established Italian restaurant and make it your own. Mamma Italia Ristorante offers an inviting dining atmosphere, bar seating, a well-equipped commercial kitchen, and an established location along Route 169 in Woodstock. The restaurant offers approximately 48 seats, including dining and bar seating, (outdoor table and chair seating available) providing a comfortable and welcoming setting for guests. The commercial kitchen is already set up for restaurant operations, providing a new owner with the infrastructure and equipment needed to step into an existing restaurant environment without starting from scratch. The wet bar and dining areas offer an inviting atmosphere for casual dining, family gatherings, and special occasions. This is a great opportunity for a family-run restaurant, chef-owner, experienced restaurateur, or entrepreneur looking to take over an established operation. Continue the current Italian concept and its traditions or bring your own vision to the space, subject to lease, licensing, and landlord requirements. Business only; real estate is not included. Additional information upon request.

Woodstock

$115,000

ACTIVE Status ⋅ 24205232 MLS

This is an approved, new lot of 1.97 acres on scenic Route 169. The slope is the the south west, and the house site is at the high spot of the land. A bit overgrown now, but once cleaned up, the lot could be mostly open with great sun exposer. The septic design is for a 3 bedroom house, set off the road. The current owner will be grading the road frontage for line of sight required by the state.

Tbd 169 Route, Woodstock

$679,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24202453 MLS

Discover the timeless charm and endless potential of this antique home in Woodstock located down the hill from Woodstock Academy. Situated on a lovely country road while remaining close to all amenities. Entering through the side door into a lovely sitting/dining area with fireplace that opens to the kitchen, which flows into a large living room, perfect for gathering family or entertaining. There is plenty of space for a home office or den too. Head upstairs where there are 4 spacious bedrooms, the primary having its own dressing room, along with 2 full baths. Lovely wood flooring throughout the home. Rich with character and antique details, this special property offers a wonderful opportunity to refresh, restore and make it all your own. Set 8.5 acres, the grounds provide plenty of room for gardening, agriculture and animals or just a quiet place to relax. The beautiful post and beam barn adds character and versatility, while providing the foundation for hobbies, storage, or animals. Come and discover all the amazing features and opportunities this home has to offer!

122 Child Hill Rd, Woodstock

$600,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24204008 MLS

Modern amenities meet unmatched seclusion in this 2,000+ sq ft colonial. A mostly level lot offers abundant green space, fruiting plants, and perennials, while the side deck and yard open to a beautiful natural view of the Still River-ideal for outdoor entertaining or quiet, serene living. Inside, gleaming maple floors lead to a first-floor bedroom with attached pass-through bath, a modern eat-in kitchen with double wall ovens and a propane stovetop, a large dining room, and a spacious living room with a functional fireplace. Upstairs, a hallway full bath serves three additional bedrooms, including the primary suite with its own attached full bath. The walk-up attic's excellent ceiling height and volume create a strong opportunity to add livable square footage. The basement's layout and ceiling height are equally well suited to finishing and expanding the home further. An attached two-car garage and paved driveway provide ample parking. If you want modern comfort, privacy, and room to grow in a peaceful woodsy setting, this is the home for you!

47 Sherman Rd, Woodstock

$589,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24201418 MLS

There's something special about being able to see the lake from home and be at the water in just a short walk. Welcome to 4 Oak Drive, a thoughtfully cared-for 2-bedroom, 2-full-bath home with a spacious loft in the Lake Bungee community. With deeded lake and beach rights and views of the water, this newer home sits on an inviting corner lot surrounded by colorful flowers, raised vegetable gardens and touches of classic New England charm. Traditional stone walls along the adjoining historic cemetery add to the peaceful character of the setting. Inside, the open-concept kitchen with granite countertops and center island flows comfortably into the dining and living areas, with windows bringing in plenty of natural light and views toward the lake. Step out onto the deck to unwind and enjoy the glowing sunsets that cast a warm light across the property. Both bedrooms are on the main level, including the primary with a large walk-in closet, private full bath and sliders to its own small deck. Upstairs, the open loft offers flexible additional space along with two closets and attic storage. The full walk-out basement with sliders provides plenty of storage and potential for future finished living space. Generator hookup ready for added peace of mind. Lovingly maintained and easy to settle into, this home offers a welcoming place to enjoy the seasons, the lake and the simple pleasures of home, all while being conveniently located near the Massachusetts line and area amenities.

4 Oak Dr, Woodstock

$125,000

ACTIVE Status ⋅ 24202057 MLS

Woodstock 13.60-Acre Residential Home Lot With 643-FT Frontage. Soil Testing, Perc Test Done. Septic Design / Engineering Done Approved. Proposed Site Plan With 4-Bedroom, 2-Car Attached Garage, And Nice Size 30' X 40' Outbuilding / Shop / Detached Garage As Well Done And Ready To Go. Most Of The Property Frontage And Both Driveway Aprons Are On Rte-197 (Old Turnpike Rd) And Continues Onto Lyon Hill Rd. Property Is Located At The Intersection Of Rte-197 (Old Turnpike Rd), Center Road, And Lyon Hill Road, Woodstock. Across Road From Laurel Spring Farm, 866 Rte-197 (Old Turnpike Rd). Driveway Apron On Rte-197 (Old Turnpike Rd) Build Site Is Accessible, Cleared, Level, Open, Already Has Two Access Ways / Driveways. See MLS Attachments For Soil Testing Results, Perc Testing Results, Survey / Site Plan, Aerial Maps, Etc. Please Do Not Go On The Property Without An Appointment.

Lyon Hill Rd, Woodstock

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