Woodstock CT Real Estate & Homes for Sale

This four-story custom-built home blends timeless craftsmanship with luxurious modern touches. Designed to showcase breathtaking lake views and sunsets, this home features exposed beams, cathedral ceilings, and oversized windows throughout. Highlights include mahogany front stairs and porches, a stucco and stone exterior, and an on-demand heated driveway. Inside, enjoy radiant heat powered by two Buderus boilers, hardwood floors, granite countertops, and travertine in the primary bath. The chef's kitchen boasts solid cherry cabinets, a 6-burner Wolf gas range, double wall ovens, and a professional-size fridge and freezer. Open-concept living flows easily across the main floor, with a wired opening for future elevator installation. Step out to your private beach and dock, professionally landscaped yard, or relax by the water's edge. The home also includes a 5-6 car attached garage, generator, new roof, and fresh exterior paint. Offering 2-3 bedrooms, 3 full baths, and 2 half baths, this home is ideal as a summer escape or year-round retreat.

Set on nearly 3 peaceful acres in Woodstock, this 4-bedroom Cape offers a flexible layout with three bedrooms on the main level, including the primary, plus a spacious loft-style 4th bedroom upstairs. The home features many recent updates: Pergo flooring in the kitchen and full bath (2022), new dishwasher (2025), water heater (2022), furnace (2019), and a repointed chimney (2021) with liner (2019). A Nashua wood stove in the basement efficiently heats the entire house. Outside, you'll find fenced-in front yard and a beautiful inground pool with a newer liner and cover (2019), surrounded by brick and granite stonework. A large cleared space at the back of the property-with its own driveway-was prepped for a future barn, workshop, or garden space. While there's opportunity for cosmetic updates, this property offers a strong foundation with valuable improvements already in place, all in a lovely country setting. Take Route 197 to Andrews Rd. (across from Deer Meadow Lane), GPS can be misleading.

Welcome to the home where sunsets paint the sky, the water whispers just steps from your door, and every day feels like a getaway. Tucked into a peaceful bay with gentle boat-speed restrictions, this contemporary waterfront retreat isn't just a place to live- it's where memories are made and moments linger. Expansive windows flood the space with natural light and showcase unobstructed views that shift from golden mornings to fire-lit evenings. Inside, thoughtful updates elevate every inch, from the complete kitchen remodel with oversized quartz counters and multiple skylights throughout, to modern LED lighting and new sliding glass doors that open seamlessly to the water's edge. The reimagined 3-season room offers a cozy extension of your living space, while the whole-house generator, upgraded 200-amp service, and newly installed heat pump and furnace ensure comfort in every season. Step outside to a private sandy beach, boat ramp, firepit, and an expansive waterfront deck with power- ideal for entertaining or simply soaking in the stillness. Nestled on a quiet dead-end road with ample guest parking and a serene sitting area off the main bedroom, this home invites you to stay a little longer... then never leave at all.

First time on the market in years! Located in the sought-after Meadowside community, this spacious lot offers the perfect seasonal escape. The property features a newer 12x27 loft-style structure with ample room to accommodate multiple beds, same sized spacious living room area, plus a covered 12x28 area ideal for relaxing or entertaining. Also included is a well-maintained 10x26 1981 camper offering a king-size sleeping area, full-size sleeping space, full bath, A/C, working mini refrigerator (not built-in), radio, and kitchen sink. Additional highlights, detached outbuilding, firepit area, stone retaining wall, access to community amenities including swimming pool, indoor recreational center, mini golf, playground, fishing pond, walking trails, coin-operated laundry, public restrooms with showers, and indoor and outdoor community rooms just steps from lot 42. Planned activities for all throughout the entire season. Don't miss this rare opportunity to own your own piece of Meadowside-schedule your showing today and start making memories!

Welcome to this beautiful 2 Bedroom/2.5 Bathrooms Townhouse with Central Air & Attached Garage located in the highly sought-after "Fairways at Woodstock" perfectly situated overlooking the picturesque Harrisville Golf Course. This serene & scenic setting offers a true New England feel, ideal for peaceful living. You will enjoy entertaining your friends & family in this spacious Living Room featuring a pellet stove, perfect for those cold winter nights, sliders leading onto the private patio, which offers panoramic views of the golf course-a true highlight of the home. The Eat-In Kitchen is ideal for entertaining between the large peninsula which offers a seamless spot for extra seating, ideal for morning coffee or social gathering as well as a casual separate dining area. A 1/2 Bath on the main floor adds convenience, attached garage offers easy access & additional storage. A grand Staircase leads to the 2nd floor which features a Primary Suite which is a true retreat, complete w/Walk-in Closet, Shower, separate Soaking Tub & large Vanity. The 2nd Bedroom also includes its own full Bathroom with a walk-in Shower-perfect for guests or family. Convenient 2nd-floor Laundry. Bonus Loft Area offers a flexible space that can be used as an office, exercise area, or cozy reading nook-complete with stunning views of the golf course from the outside deck. Don't miss your chance to live in one of Woodstock's most desirable communities. This is a GEM. You will be Proud to call this HOME!

View this home on April 27th- 12pm-2pm-This oversized colonial home with central air and gleaming hardwoods is move in ready. Are you wanting space and storage?, well this home will check both of those boxes. The massive 3 car garage offers an additional walk-up storage space, as well as an additional bay in the rear. If that wasn't enough you will find a 2 bay storage shed/garage on the side of the property as well as a shed in the backyard. This home provides privacy with it's 3.5 acre wooded lot. The fenced in back yard with a patio is perfect for the evening barbeques. The kitchen offers granite and a large counter, there are 2 fireplaces, 1 in the living room and 1 in the family room, there is also a formal dining room. Additionally, there is a primary suite on the 1st floor that offers a walk-in closet. Laundry is on the main level with a 1/2 bath, The second floor offers 2 extra large bedrooms as well as a full bath.

Situated on 3 scenic acres, this classic ranch-style home offers timeless charm and abundant potential. Being sold as-is, this property presents an excellent opportunity for buyers looking to invest in a solid home with room for customization.The residence features original hardwood floors throughout, while a cozy fireplace creates a welcoming gathering space during cooler months. A spacious two-car garage with a second story provides ample storage or space for future expansion. Outdoors, enjoy the tranquility of active streams that flow through multiple areas of the property, offering a peaceful country setting just a short drive from local amenities. This property is ideal for those seeking space, serenity, and the chance to create something truly their own. Schedule your private tour today.

Prominently located on prestigious Woodstock Hill, this 1850 Greek Revival Farmhouse sits on the easterly side of the road, enjoying morning sun rises from its two porches! A short walk to The Woodstock Academy, the Woodstock Hill Congregational Church, and The Inn at Woodstock Hill, and just 45 minutes to Harford, 30 minutes to Worcester and 1.15 to Boston you simply cannot ask for a better location! This 2200 SF home has seen many renovations over the years both aesthetically and mechanically making it move-in ready for its next lucky owner. There are 4 bedrooms, including one on the first floor that could also serve as a great home office. Upstairs there are 3 bedrooms, one with its own ensuite bath and another privately set at the rear of the home with its own dressing room, window seat and many built-ins. The home enjoys a gracious front foyer and a lovely 2nd floor landing. It is the kitchen though where this home sings the most with a large eat-in area, granite countertops and updated stainless appliances. The Dining Room enjoys a wood fireplace surrounded by built-ins with the Living Room to the front from there. Downstairs is a heated room perfect for a home gym and a 2-car garage.

Welcome to your home away from home! This is your opportunity to own your very own campsite located in in the beautiful Meadowside of Woodstock community! Included is a 1995 33' Corsica Cobra 30BH trailer that has been well cared for. The trailer has a queen bed and a bunk room with two additional sleeping bunks, a full bath with a standup shower and an eat-in kitchen. There is an addition which adds additional living space, perfect for an office, family room or additional sleeping space. Everything you will need to start camping right away will be included! The camper is conveniently located on a corner lot right across from the pool, clubhouse and laundry facilities and has two sheds for all of your exterior storage needs. There is a 2-year young patio and stone retaining wall. There is a fishing pond, mini golf, playground, and a rec hall for residents to enjoy along with all of the campground events throughout the season. The campground is open mid April through October. Schedule your showing today and be ready to start camping at the beginning of the season! Property sold as-is, where-is.

Welcome to Eastwood Estates - Luxury Living in the Heart of Woodstock! Discover the elegance and tranquility of Eastwood Estates, a prestigious enclave of just eight finer homes nestled in one of Woodstock's most desirable settings. This 3,356 sq ft Colonial TO BE BUILT is thoughtfully designed for those seeking timeless sophistication, quality craftsmanship, and a connection to nature. With 18 acres of conservation land just beyond your backyard, this is truly a nature lover's paradise. Home Features Include: 4 spacious bedrooms & 3 baths. Gourmet kitchen with stainless steel appliances, quartz or granite countertops, large pantry & breakfast nook. Formal living & dining rooms. Show-stopping family room with vaulted ceilings, gas fireplace, and custom hearth/mantel. Loft/flex space overlooking family room - ideal for home office, media, or playroom. Primary suite with spa-like bath: tiled walk-in shower, glass enclosure, soaking tub. Separate main-level laundry area. Engineered hardwood flooring throughout, 9' ceilings & crown molding in formal rooms. Custom tile work in all bathrooms. Bonus Potential: A full walk-out lower level offers over 900 sq ft of space for future in-law accommodations, home gym, or additional living area. Prime Location: Enjoy the serenity of a country lifestyle with access to top-rated schools and easy commuting routes to Massachusetts and Rhode Island. Let's build your dream home together- tailored to your taste and lifestyle.

Welcome home. This Woodstock condo is ready to go. New kitchen, updated bathrooms all new interior doors....fresh and clean. Fireplace in the living room, hardwood floors on the first floor. 2 bedrooms and 1.5 bathrooms. Full basement. Private back deck and a 1 car detached garage. Come relax and enjoy.

Spring is coming and this charming cape is ready to be your new home. Meticulously done with so many new features. Large living room with fireplace, or woodstove and gleaming hardwood floors through out! Screened in porch just waiting for you to enjoy your morning coffee. Updated bathrooms, kitchen, newer appliances...every inch has been painted and made ready for its new owner. New Septic, New Shingles, New well, Newer vinyl siding and replacement windows, generator hook up. Attached garage and easy access to main road and commute to 184. Nothing to do but move in!

The Historic General Samuel McClellan Estate - A Timeless Luxury Retreat. Experience the perfect blend of historic grandeur and modern luxury at this extraordinary estate, meticulously restored with $1.3 million in improvements. This multi-residence compound offers exceptional living and investment potential. Three Distinctive Homes: The Main House - A former bed and breakfast featuring six ensuite bedrooms, each bath newly remodeled. The Cape House - A stunning 3-bed, 2.5-bath home, fully renovated. The Pool House - A luxury studio with indoor & outdoor kitchens, a fireplace, expansive sliding glass doors, and spa-like bath. Unparalleled Amenities: New saltwater pool with automatic retractable cover and serene views. Renovated barn with a new foundation, new siding and a six-car garage. Extensive stonework, landscaping, and new roofs on all structures. Once home to Revolutionary War General Samuel McClellan, this estate is rich in history while offering tremendous commercial potential as a luxury B&B, event venue, school housing, or multigenerational retreat. During the Revolutionary War in 1775, General McClellan led 184 men at the Battles of Lexington and Concord and also played a prominent role in the Battle of Bunker Hill. Ideally located across from the peaceful village green, near top schools, fine dining, and I-395. A rare opportunity to own this landmark property in desirable Woodstock CT. Sale Includes #6 & #8 Stone Bridge. Please schedule your private tour today!

Seller is willing to cosmetically customize for the buyer within reason. On the water and waterfall estate! This exceptional estate, nestled on serene waterfront land offers the perfect blend of timeless craftsmanship and modern luxury. From its historic charm to its state-of-the-art mechanics, this home offers a unique opportunity for those seeking both beauty and functionality. The main house has 4 bedrooms and 4 full baths including one 2-person and one 2-4 person jacuzzi tubs, has been freshly painted and features original architectural details like hardwood floors, exposed beams, and period fireplaces. The estate has cutting-edge mechanical systems while preserving cost-prohibitive materials and craftsmanship .Built-in brick kitchen appliances and slate floors give this spacious kitchen a rustic, yet luxurious feel. The guest cottage overlooks a babbling brook and waterfall. This offers a tranquil space for visitors or a potential income-generating vacation rental. The beautifully landscaped estate includes mature trees, gardens, and pathways leading to the brook and waterfall, along with patios and seating areas for peaceful outdoor enjoyment. This property is currently a successful Airbnb, attracting guests who seek a retreat in nature, offering endless possibilities for either continuing as a vacation rental or transforming into a private residence.

Welcome to this classic New England Colonial set on a serene 1.6-acre lot on a designated scenic road, steps from historic Woodstock Hill and the Woodstock Academy. Spanning 2,682 sq. ft., this charming property boasts four bedrooms and timeless elegance with thoughtful details throughout. The kitchen features wide-plank oak floors, a cozy dining area, and an open-concept layout, making it ideal for both daily life and entertaining. The formal dining room, with its wainscoting and crown molding, adds sophistication to every gathering. Unwind in the family room, featuring exposed beams, a fireplace, and built-in bookcases, or relax in the front living room with its own fireplace and elegant crown molding. A cozy back office with exposed beams offers privacy and character. The primary bedroom suite includes a newly renovated bathroom with double sinks and an adjacent versatile room, ideal as a walk-in closet, nursery, or small office. Hardwood flooring spans the entire second floor, adding to the home's inviting ambiance. Outside, enjoy a 20' x 40' gunite inground pool, freshly painted exterior, 2 year old roof, and a recently repaved driveway. Completing the property are a detached two-car carriage shed garage and a small barn, perfect for storage or hobbyists. Discover New England charm, privacy, and convenience in this one-of-a-kind Woodstock home.

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!

Welcome to this charming 2.7-acre property, where functionality meets potential. Perfectly suited for horse enthusiasts, this small yet mighty property provides endless possibilities-whether you're looking to house your own horses, run a boarding business, or provide training. The beautifully remodeled antique home exudes warmth and character, featuring a cozy living room with a wood stove, a formal dining room with built-in cabinetry, and a convenient first-floor primary bedroom and bath. The stunning eat-in kitchen is sure to captivate, with a breakfast nook that overlooks the paddocks, making every meal a serene experience. With abundant storage-rare for a home of its age-and numerous thoughtful updates, this property provides both charm and modern convenience. (Please see attachments for full details.) Equestrian enthusiasts will feel right at home with a spacious 60' x 120' indoor arena, a winter essential for New England's colder months. Alternatively, enjoy the outdoors in the 100' x 200' lighted outdoor arena, ideal for riding year-round. The main barn is well-equipped with 10 matted stalls, a bright and wide aisle, personal tack boxes, a wash rack, hay storage, and an additional tack and feed room. Behind the barn, there's ample pasture space for grazing, plus two extra in-and-out stalls with paddocks for added flexibility.