Woodstock Homes under $2 million

Welcome to Woodstock, Connecticut – a charming town nestled in the picturesque Windham County, where the serene beauty of New England meets a vibrant community spirit. Known for its rich history, Woodstock offers a unique blend of rural charm and modern conveniences, making it an ideal place to call home.

As you explore the enchanting streets of Woodstock, you’ll be captivated by its stunning landscapes, which feature rolling hills, lush forests, and tranquil lakes. The town is steeped in history, with beautifully preserved colonial architecture and a variety of cultural attractions, including art galleries, local farms, and seasonal festivals that celebrate the area’s heritage.

For those seeking a home in this idyllic setting, Woodstock offers a diverse selection of properties under $2 million. Whether you’re looking for a cozy cottage, a spacious family home, or a luxurious estate, you’ll find an array of options that cater to a variety of lifestyles and preferences. Many homes boast expansive yards, stunning views, and easy access to outdoor activities, ensuring that you can enjoy the natural beauty that surrounds you.

With a strong sense of community and a commitment to preserving its natural environment, Woodstock is not just a place to live but a place to thrive. The town’s excellent schools, friendly neighbors, and an abundance of recreational opportunities make it perfect for families, retirees, and everyone in between. Discover the charm of Woodstock and find your dream home today!

Newest Woodstock Homes under $2 million

$374,900

4 Beds ⋅ 2 Baths ⋅ 24209768 MLS

Really does a two-family home ever come on the market in Woodstock, never mind one on 3.5 acres. Even more rare is finding a two-family home you can live in with a large commercial/industrial garage for all of your toys, projects, and potential business use. Property consists of two, 2 bedroom-1-bathroom apartments. Each unit paying their own electric/heat. The lower garage has its own electric panel, heat and even a half bathroom. Oversized 10-foot brand new garage door along with steel I-beam construction. Proper property has a newer septic system, and a modern drilled well.

616 Rte 197, 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

$750,000

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

$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

$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

$549,000

2 Beds ⋅ 2 Baths ⋅ 24201418 MLS

There's something special about seeing the lake from home and being 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. Offering deeded lake & beach rights and water views, simply walk across the street to the boat launch and enjoy easy access to the lake. This newer home sits on an inviting corner lot surrounded by colorful flowers and raised vegetable gardens, plus an oversized shed less than a year old for additional storage. Traditional stone walls along the adjoining historic cemetery add to the peaceful New England setting. Inside, the open-concept kitchen with granite countertops and center island flows comfortably into the dining and living areas, with plenty of natural light and views toward the lake. Step onto the deck to unwind and enjoy the glowing sunsets. Both bedrooms are on the main level, including the primary with a large walk-in closet, private full bath and sliders to its own deck. Upstairs, the spacious loft offers flexible additional living space, two closets and attic storage. The full walk-out basement with sliders provides excellent storage and potential for future finished space. Generator hookup ready. Lovingly maintained and move-in ready, this welcoming home offers a wonderful place to enjoy the lake, the seasons and the simple pleasures of home, conveniently located near the MA line and area amenities.

4 Oak Dr, Woodstock

$199,900

2 Beds ⋅ 1 Baths ⋅ 24201823 MLS ⋅ Fawn Ridge BLDG.

Welcome to this beautifully renovated 832 sq. ft. end-unit condo in Woodstock, CT, offering an inviting opportunity to trade renting for owning and start building equity of your own. Freshly updated with new paint and flooring, this home provides a clean, comfortable setting that's ready for you to make your own. As an end unit, the home offers added privacy and a desirable layout. Whether you're a first-time homebuyer ready to take the next step or simply looking for an affordable way to put your monthly housing toward ownership, this condo is a smart place to begin. Enjoy the simplicity of condo living while taking advantage of all that charming Woodstock has to offer. Why keep paying rent when you can start building something of your own? Come see how easy homeownership can be!

12 Fawn Rdg Unit 12, Woodstock

$549,900

3 Beds ⋅ 3 Baths ⋅ 24201270 MLS

There's something special about being the first to call a brand-new home your own! Set within a desirable Bunggee lake community in Woodstock Valley, this new construction Cape offers approximately 2,230 sq. ft. of finished living space across three levels with 3 bedrooms and 2.5 baths. The main level features an expansive wraparound kitchen, sliders leading to the back deck, and two separate living spaces that can easily adapt to your lifestyle. Create an eat-in kitchen with two living areas, a living room and den, or use one as a spacious formal dining room. A convenient half bath and laundry room complete the first floor. Upstairs are two generous bedrooms, a full bath, and a spacious primary suite with its own private bath and walk-in closet. The finished walkout lower level adds even more flexibility for a family room, home office, gym, hobbies, or additional recreation space and connects directly to the one-car under-house garage. Outside, the private backyard is surrounded by mature trees with a level, open area offering plenty of room for entertaining, gardening, play, or simply relaxing outdoors. The home is nearing its completion, giving you the opportunity to be its very first owner and enjoy all the benefits of new construction without starting from scratch. A great combination of space, privacy, flexibility, and lake-community living! Lake rights and fully recreational amenities offered by Bunggee Lake, including boating, fishing, and swimming opportunities.

61 Red Cedar Rd, Woodstock

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