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

$799,000
4 Beds ⋅ 2 Baths ⋅ 24206040 MLS
Tucked away at the end of a long private driveway, this 3,794-square-foot custom home offers four bedrooms on nine scenic acres, with potential for a free land split. Wood flooring milled from trees on the property, natural beams and built-ins lend warmth and character. Every door is custom made; the doors, staircase treads and living room floor are Brazilian cherry. A pass-through stone-and-brick fireplace anchors the living space, while steel-beam construction extends through the house, basement and garage. The granite kitchen features an island, new hardware and a new commercial-grade propane range with 10 burners and double ovens. Windows surround the four-season great room, bringing in light and views year-round. A first-floor primary suite offers one-floor living. Above the oversized two-car garage, a cathedral-ceiling bonus room offers flexible space for an office, studio or guests. Updates include an automatic Generac generator, 2009 roof, new garage doors, stainless-steel chimney liner, repointed chimney, new gutters, gas lines, tamper-resistant outlets, lighting, new dishwasher, a new boiler (February 2026) and fresh paint. Enjoy privacy close to schools, restaurants, shopping and I-395 in Woodstock.

555 Senexet Rd, 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
$175,000
2 Beds ⋅ 1 Baths ⋅ 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
$164,900
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
$164,900
73573956 MLS
Enjoy quiet and privacy 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 are serviceable. The pond has dried up, appears the dam needs some work.

XO Pole Bridge Rd, Woodstock
$499,900
3 Beds ⋅ 3 Baths ⋅ 24203840 MLS
To be built 6.5 room Colonial Home 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
$125,000
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
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
$509,000
3 Beds ⋅ 2 Baths ⋅ 1422207 MLS
Looking for a home that exudes the character and craftsmanship of bygone days without the challenges of a true antique? 15 Paine District Road looks and feels like it's been here for centuries, but this gorgeous reproduction Saltbox is less than 40 years old. Hand-built by its original owner with extraordinary attention to craftsmanship and period-inspired detail, it offers the warmth and character of early New England architecture recreated for modern living. Huge blocks of granite form the entry steps to each of the three doors, while exposed rough hewn beams and an oversized fireplace harken back to quieter days. Custom cabinetry and millwork by the renowned craftsmen at Brunarhans can be found throughout the home, from the solid wood kitchen, custom chair rails and molding to the raised paneled wall surrounding the fireplace. The kitchen features a cooking island and charming bay window dining nook with built-in seating. The flexible floor plan offers 3 bedrooms, including one on the first floor currently used as an office with more beautiful built in floor to ceiling custom cabinetry. The second floor offers a spacious primary and two additional bedrooms, the smaller one currently being used as a separate laundry area and playroom. The oversized garage includes a workshop area and storage loft. If you think this property looks pretty now, just imagine it when the fall foliage blooms. Act now and you can be moved in by peak leaf season, your pumpkins and scarecrow await!

15 Paine District Road, Woodstock
$679,000
4 Beds ⋅ 3 Baths ⋅ 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 ⋅ 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
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