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$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
$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
$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 ⋅ COMING SOON 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
$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
$549,900
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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
$650,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24197102 MLS
This 4-bedroom, 2591sqft Cape is on cul-de-sac, conveniently located in South Woodstock. Offering combination of classic character with hardwood floors and comfortable living spaces, this single owner home is ready for it's next chapter. The main level living area is all hardwoods, with a kitchen/dining combination, a living room with a propane fireplace, and an office with tons of built-ins. Come in from the garage that is equipped with shelving and a set tub, to the mudroom with open locker style storage. Privately tucked to the rear of the main floor is the primary suite, with a large walk in closet, and full bath. The 2nd level is a surprise with 3 good sized bedrooms, a full bath, a great closet storage space, and a future living space, already studded with rough plumbing and electric. The level back yard offers room to relax, play, garden, or entertain. The irrigation system will keep the lawn green. No HOA, Senexet Village Road is town owned, and also hosts a recreation area for all to use.

23 Senexet Village Rd, Woodstock
$2,500,000
3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24196666 MLS
Welcome to this 80 acre Connecticut Estate, tucked into the rolling hills of Woodstock Ct. This exceptional 4,655 sq ft contemporary home offers a unique living experience with its own privately owned public FAA approved commercial grade airport. The property is a pilot's paradise, featuring a spacious hangar that not only accommodates multiple small planes and helicopters but also offers ample room for vehicle storage. The hangar is self-sufficient with its own septic, well, electrical, and heating systems, providing convenience and flexibility as well as a finished lounge area to gather and relax. This property is a rare find, offering a blend of luxury, functionality, and the ultimate in private aviation convenience! Whether you're an avid pilot, car enthusiast, or simply seeking a tranquil retreat, this home promises an unparalleled lifestyle. This residence boasts privacy and scenic New England beauty with stunning views. The contemporary design, built in 1987, features 3 bedrooms and 4 bathrooms, open living space with soaring ceilings, two story fireplace, and a beautiful open center oak staircase. The home's large windows and open layout invite the natural surroundings inside, creating a harmonious living environment. The finished walkout lower level offers beautiful views of the pond and the plush grounds. So many exciting possibilities!

80 Bungay Hill Rd, Woodstock
$698,900
2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24193568 MLS
Enjoy Lake Living in Woodstock's Quiet Corner at Quasset Lake! Welcome to this beautifully landscaped 2-3 bedroom, 2.5-bath home in the desirable Quasset Lake community, where lake living and year-round recreation await. Located directly across the street from the association's private boat launch and deeded lake/beach access, you'll enjoy convenient access to swimming, boating, kayaking, and fishing just steps from your front door. Designed for both everyday living and entertaining, the open-concept main level features a gourmet kitchen with a center island, fixed breakfast bar, and seamless flow into the dining area and family room. A stunning floor-to-ceiling, double-sided fireplace creates a warm and inviting atmosphere, serving both the family room and the first-floor primary suite. The spacious primary bedroom includes a full en-suite bath and a private sauna and standup tanning booth, offering the perfect retreat after a day on the lake.

20 Loyola Rd, Woodstock
$74,999
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24193441 MLS
Welcome to your summer "Home away from Home" Looking for your "Seasonal Home Away from Home" Look no further this cute as a button, privately situated park model. Fresh new updates and newly applied finishing touches, makes this unit able to just move on in and start enjoying the rest of the season. Just steps from the amenities. pool, pavilion, mini golf, cornhole field, basketball and short walk to the catch and release fishing pond. While also enjoying the tranquility of the home away from home feeling. This unit comes almost completely furnished.

25 Rte 197th Rte, Woodstock
$599,000
2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24187780 MLS
Perfect Countryside Elegance. Welcome to 511 Perrin Road, an exceptional country estate gracefully set atop a private 3.5-acre hillside in scenic Woodstock. A long paved driveway winds through picturesque grounds to this beautifully crafted home, where timeless architecture meets modern efficiency with 100% owned solar. Designed for effortless one-floor living, the residence features a luxurious first-floor primary suite, private executive office, gleaming hardwood floors, exquisite custom built-ins, and an inviting open living and dining area anchored by a dramatic back to back wood-burning fireplace. The custom Brunarhans kitchen is a showcase of quality craftsmanship and thoughtful design. The home boasts 2,393 SqFt of finished living space with 2.5 baths. The second level offers a spacious guest bedroom, full bath, and a connected bonus room, providing exceptional flexibility for family and guests. Step outside to enjoy the serenity of the private patio, a charming pond, and sweeping open grounds. The expansive lawn offers outstanding potential for a boutique vineyard, gardens, or equestrian pursuits, with horses and household pets permitted and ample room for paddocks. Completing this remarkable property is an oversized two-car garage with a private workshop. A rare combination of privacy, elegance, sustainability, and refined country living. A truly exceptional offering in one of Woodstock's most desirable locations.

511 Perrin Rd, Woodstock
$479,900
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24187904 MLS
Welcome home to this charming colonial tucked away on a peaceful cul-de-sac, offering privacy and picturesque views on a full acre of land. As you step in through the fresh new mudroom, you will find a spacious, bright living room, a separate dining room, and a beautiful kitchen with stainless steel appliances, a breakfast bar, abundant cabinet space, and access to a private back deck overlooking a scenic backyard and surrounding nature. Just off the kitchen, you will find a versatile bonus room currently used as a bedroom offering endless possibilities as a family room, home office, playroom or guest space. This area also features a wood stove, and a convenient laundry room complete with a bonus shower and sink. Upstairs the spacious primary bedroom includes a walk in closet, accompanied by two additional bedrooms and a full bath with a brand new double vanity. Major improvements provide added peace of mind, including a brand new roof and siding, water filtration system, new hot water heater, new washer and dryer, and leased solar panels for improved energy efficiency. A two car garage and beautiful natural surroundings complete this move in ready home in a highly desirable location.

21 Fairfield Dr, Woodstock
$1,275,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24185273 MLS
Waterfront living at its most private and picturesque on beautiful Chamberlain Lake. Set on 200 feet of private lake frontage, this exceptional custom post-and-beam Cape offers a rare combination of craftsmanship, character, privacy and direct access to the water. Thoughtfully designed and built using timber milled from trees harvested on the property, the home has an unmistakable warmth and authenticity. A dramatic center brick chimney anchors the main living spaces, complemented by wide-board pine floors, exposed beams and abundant windows framing the surrounding landscape and lake. The spacious primary suite features a private balcony overlooking the water, two walk-in closets and a spa-like bath. Generously sized rooms and oversized step-in closets provide exceptional comfort and storage throughout. Step outside and enjoy the best of lake living with a private pathway leading to the water, ideal for swimming, fishing, kayaking and canoeing. Relax on the covered porch, gather around the fire pits, or enjoy the outdoor shower after a day on the lake. Beautifully landscaped grounds create a peaceful and private setting surrounded by mature trees and natural beauty.

95 Pole Bridge Rd, Woodstock
$625,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24183359 MLS
Step into this remarkable 2,400-square-foot farmhouse In Woodstock Connecticut. Rich in character and timeless charm, this exceptional property offers the opportunity to enjoy the beauty of country living while creating the homestead, estate, venue, investment you've always envisioned. Thoughtfully renovated in the 1980s, the home was updated while preserving the character and charm that make this farmhouse so special. The result is a home that offers the warmth, personality, and craftsmanship of another era with the functionality needed for comfortable modern living. Outside, the possibilities are truly enless. Whether your dream is to cultivate expansive gardens, raise animals, have a country retreat, have your own bread and breakfast or simply enjoy more space for you and your family, this property offers the space and setting to make it happen! Imagine gathering in the large dinning area and enjoying your own fresh produce or enjoying peaceful mornings on the expansive deck creating a private retreat to call your own or guests. Despite its peaceful rural atmosphere, convenience is never far away. Shopping, dining, everyday amenities, and major highways are all within easy reach, giving you the best of both worlds-privacy and country charm without sacrificing accessibility. This is an opportunity worth taking a closer look at. All offers will be considered.

429 New Sweden Rd, Woodstock
$880,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24180671 MLS
Welcome to this exceptional custom-built ranch, perfectly situated at the end of a peaceful cul-de-sac in South Woodstock. Offering a great blend of luxury, comfort, and versatility, this impressive home boasts 2,822 square feet of beautifully designed main-level living space, with over 5000 square feet of total finished living area including the private in-law apartment above the garage and the spacious walk-out lower level. Stepping through the front door, be captivated by soaring ceilings, arched doorways, and quality craftsmanship throughout. Generously sized living areas provide the perfect setting for entertaining family and friends, while thoughtfully designed spaces offer comfort and privacy for everyday living. The home features spacious bedrooms, abundant storage, and countless custom details that reflect pride of ownership and meticulous attention to quality. Come see this property to see all that it offers.

48 Grey Fox Lndg, Woodstock
$1,995,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24180508 MLS
Extraordinary Waterfront Estate. Set on an exceptional 5.5-acre private lot with 265 feet of shoreline frontage, this completely rebuilt luxury residence offers a rare opportunity to own one of Woodstock's premier lakefront properties. Arrive via a long, newly paved private driveway that winds through a tranquil setting before revealing this stunning waterfront retreat. Offering 3,971 square feet, 4 bedrooms, and 4 bathrooms, the home was rebuilt from the ground up with next level quality and craftsmanship. Designed for both elegant entertaining and everyday enjoyment, the layout includes a formal dining room, spacious family room, custom mudroom, and a beautiful living room with propane fireplace overlooking Quasset Lake. The showpiece kitchen is truly one-of-a-kind, featuring handcrafted cabinetry by a New York artisan cabinet maker, thick quartzite countertops, premium built-in appliances, and a dramatic tray ceiling with custom white oak detailing. Luxury finishes continue throughout with veneer plaster walls, custom white oak vanities, a professionally designed primary closet, handmade laundry room cabinetry, and architectural flangeless LED lighting seamlessly integrated into the wood ceilings. Built with 2x6 construction, engineered floor systems, 2x12 roof rafters, red cedar siding and trim, central air, all-new heating and cooling systems, underground 400-amp service, and an automatic whole-house generator. Step outside and embrace the ultimate lake lifestyle.

158 W Quasset Rd, Woodstock
$1,395,000
4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24177811 MLS
Set on 10.3 private acres in desirable Woodstock Valley, "Blue Heron Glade" offers a rare blend of privacy, natural beauty, and thoughtfully designed living spaces in Connecticut's Quiet Corner. A long private driveway with a charming cobblestone bridge leads to this exceptional property surrounded by stone walls, abundant wildlife, and a large pond frequented by blue herons. The main residence offers over 6,000SF above grade plus an extensively finished lower level designed for entertaining and everyday comfort. The kitchen features granite countertops, a large center island, and abundant cabinetry. The first-floor primary suite includes tray ceilings, a spa-like bath with double sinks, a 2-person jetted tub, and separate shower. The finished lower level offers a completely unique atmosphere with a custom speakeasy-style bar, theater room, full bath, dog washing station, laundry area, and private office suite with 2 rooms and an additional full bath. An attached in-law apartment has its own bedroom, full bath, kitchen & loft/office area, and newly added white oak flooring. 4 oversized garage bays, 2 of which offer unfinished loft space above. Outside, enjoy the fenced inground pool area with beautifully updated landscaping & a pool house complete with plumbing, granite counters, half bath, & outdoor shower. Fiber internet with mesh nodes provides seamless connectivity throughout the house. A rare Woodstock Valley retreat where privacy, nature, and luxury come together.

1374 Rte 171, Woodstock
$799,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24165439 MLS
TO BE CONSTRUCTED | Starting at $799,900 Welcome to Eastwood Estates, where luxury living meets the natural beauty and tranquility of Woodstock. Set on a picturesque 1.92-acre homesite bordering protected open space and framed by classic New England stone walls, this offering provides a rare opportunity to build a custom home in one of the area's most desirable neighborhoods. Partner with an experienced local builder to create a home that reflects your lifestyle and vision. Choose from thoughtfully designed plans, including a stunning Country Colonial featuring 4 bedrooms and 2.5 baths, or explore alternative layouts, or bring your own ideas to life within the builder's program. Each home is crafted with attention to detail, blending timeless elegance with modern functionality; open living spaces, quality finishes, and design flexibility suited for today's living. Eastwood Estates is governed by covenants that preserve the integrity and value of the neighborhood, including a minimum home size of 2,900 square feet (which may include finished lower-level space). Enjoy the peaceful charm of Woodstock with nearby access to local farms, walking trails, and scenic roads, while still being within reach of everyday conveniences and commuting routes. A unique opportunity to build a home that is both refined and personal, guided every step of the way.

36 Olde Meadow Rd, Woodstock
$689,000
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24142329 MLS
Perched above the shoreline of private Witches Woods Lake, this beautifully renovated waterfront retreat pairs breathtaking water views with exceptional privacy and an incredible indoor-outdoor lifestyle. Nearly 800 square feet of brand-new multi-level TimberTech decking takes full advantage of the setting, creating an extraordinary space for entertaining, dining, relaxing, and enjoying the lake below. Thoughtfully and extensively improved, the home features a refreshed granite and stainless kitchen, whole-house mini-split heating and cooling, a new full septic system, Kohler automatic generator, updated baths, and numerous additional improvements throughout. The main level offers an easy flow between the kitchen and living room, two bedrooms, a full bath, and a sun-filled enclosed porch opening directly to the decks and panoramic lake views. The professionally waterproofed, finished walk-out lower level adds valuable flexibility with a spacious recreation room, full bath with laundry, and direct exterior access. A one-car garage, breezeway, and multiple storage areas add everyday convenience, and the home is offered furnished for an easy transition into lake life. Witches Woods Lake is treasured for its peaceful atmosphere and natural beauty, offering kayaking, swimming, fishing, sailing, and regulated power boating, while restrictions on jet skis and personal watercraft help preserve the quiet character of this special waterfront community.

60 Indian Spring Rd, Woodstock
$520,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24125003 MLS
Step back in time with this one-of-a-kind 1830 Greek Revival farmhouse, offering 2,150 sq ft of character and charm on a picturesque 0.90-acre lot surrounded by farm land. Just down the hill from historic Woodstock Hill and the Academy, this setting is as scenic as it is convenient. Inside, wide plank floors and distinctive windows frame beautiful country views, while the front entry showcases its original door with full exterior shutters, a hallmark of Greek Revival style. The living room centers on a classic fireplace, and along the upstairs landing a wall of built-in bookshelves creates a welcoming library space. Three bedrooms are located on the second floor, with an additional first-floor room currently serving as a fourth bedroom. The primary includes a walk-in closet and bath with a clawfoot tub. The walk-up attic offers potential for an office, playroom, or studio. The kitchen features a custom layout paired with quality appliances (Sub-Zero fridge & Thor cooktop) and the warmth of a wood stove. Updates include new Trex decking and a newly finished three-season room off the dining room. Historic touches, such as unique wallcoverings and original details, remain intact, blending history, artistry, and the timeless charm of living in Woodstock, CT. Property to be sold in as-is condition.

101 Child Hill Rd, Woodstock

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