$496,863Average Value$290Average Price per Sq Ft15Homes For Sale
A hidden residential gem in the Quiet Corner of New England
When successful New York businessman Henry Bowen built a pink summer home in the countryside of Woodstock, he started a trend that continues in the Connecticut town today. Transplants and visitors from across the Northeast, particularly New York, head to the sprawling estate homes and vacation rentals amid the dairy farms and wineries of this rural community, anchored by a wide variety of established housing that is affordable enough for the average homeowner seeking natural beauty and seclusion rather than an exhilarating urban lifestyle. This tranquil town of fewer than 8,000 is located in the Quiet Corner, a segment of northeastern Connecticut known for its distance from any major cities.
Woodstock sign that tells it's neighborhood's story.
Pre-Railroad homes can be found easily in the Woodstock neighborhood.
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From cozy Cape Cods to sprawling estate homes
Homes are spread out among Woodstock’s large land area, which ranks second among Connecticut towns. Cozy Cape Cods and larger Colonial Revival homes are prominent among the town’s established housing, while new construction often features the traditional window-heavy facades of the Colonial Revival style. Ranch-style homes and contemporary custom designs also can be found among housing typically priced from the high $200,000s to more than $2 million. The median lot size is nearly 2 acres, although numerous homes occupy sprawling lands of 50 to 100 acres. Lavish estate homes on the high end of the price range can offer unique features such as their own airfield or medieval moat. Waterfront homes built along the town’s collection of lakes and large ponds are common as well. The average home value of just over $450,000 is more than $100,000 higher than the Windham County average.
The Olde Pineapple that blends in with Woodstock's National homes.
Colonial homes are common in Woodstock.
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Top-notch private education is free for Woodstock high schoolers
The Woodstock School District comprises Woodstock Elementary and Woodstock Middle, both B-minus-rated schools by Niche. Most high schoolers attend The Woodstock Academy, an A-minus-rated private college preparatory school that’s free for Woodstock residents. Founded in 1801, the academy serves approximately 1,100 students from Woodstock and five other surrounding towns. It offers more than 20 Advanced Placement courses among a curriculum of more than 230 courses and features the state-of-STEAM Center and Loos Center for the Arts.
Families from all over the country move to Woodstock for it's infamous Woodstock Academy.
Welcome to Woodstock Middle School in Woodstock.
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Water, water everywhere provides plenty of recreation
Woodstock’s parks make the most of the town’s many lakes and ponds. For example, Crystal Pond Park encourages visitors to bring their kayaks and canoes to paddle around the waterway, nearly as expansive as a lake. The park is open year-round, with boating and swimming in the warm months transitioning to ice skating and cross-country skiing in the winter. Though Roseland Park rests on the shore of Roseland Lake, swimming isn’t allowed. Instead, paddlers skim across the surface of the lake while kids frolic on the playground and youth baseball games are contested on the baseball field. Residents can swim Muddy Pond at Town Beach, although there are no lifeguards. The pond can be fished, and small watercraft are allowed. Golfers can enjoy a relaxing couple of hours on the links at Harrisville Golf Course’s public 9-hole layout.
Kayakers and canoers can paddle across the water at Crystal Pond Park.
Woodstock Town beach can also be a great spot for a family picnic with great views.
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A contemporary destination for antiquing
Antique shops and fresh food marketplaces define Woodstock’s business sector. Locals and tourists frequent the remote boutiques and emporiums spread across town. They shop for vintage furniture at The Rusty Relic, browse antique home décor at The Olde Pineapple and pick up beef or milk straight from the farm at Elm Farm’s Farm to Table Market. Fruits and vegetables are on sale at Woodstock Orchards produce market, but residents need to drive to the town of Putnam to shop at a supermarket, such as Price Chopper. The nearest full-service medical center is UMass Memorial-Harrington Hospital 10 miles away.
Woodstock is infamous for its antique shop like Scranton's Shops.
Rusty Relic can easily be found by using one of their classic trucks as signage.
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Roseland Cottage: A venue fit for a president
Taylor Brooke Winery hosts gatherings and celebrations several times a week throughout the year, from indoor cornhole matches to live musical performances. Of course, the vineyard’s wines often are incorporated into events, such as the December Sip & Shop Holiday Market. Roseland Cottage, Henry Bowen’s Gothic Revival estate visited by four U.S. presidents, hosts 150 artisans from across New England at the annual Roseland Cottage Fine Arts & Craft Festival.
Built in 1846, Roseland Cottage today hosts an annual arts festival in Woodstock.
Roseland Park barn can be used for events.
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Boston, Worcester, Hartford within reach
Seclusion is part of Woodstock’s appeal, but it’s a simple drive to several New England cities. Highways such as Connecticut Routes 169 and 171, as well as nearby Interstate 395, put drivers on the path to Worcester, Mass., 30 miles to the north, Boston, 70 miles to the northeast and Hartford, Conn., 45 miles west. Travelers can catch planes at Rhode Island T.F. Green International Airport 40 miles away in Warwick, but Boston Logan International Airport offers more flight options.
Crime
The town enjoys the CAP Index’s lowest possible crime rate, scoring a 1-out-of-10.
Photography Contributed By
Jack Lourenco
Interested in learning more about homes in this area?
Reach out to
Mary Collins,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
On average, homes in Woodstock, CT sell after 38 days on the market compared to the national average of 57 days. The median sale price for homes in Woodstock, CT over the last 12 months is $450,000, up 5% from the median home sale price over the previous 12 months.
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
This lakeside escape was completely redone in 2023. This beautifully updated 1-bedroom, 1-bath year-round home is nestled on the shores of private Quasset Lake in Woodstock. This direct waterfront property is an absolute paradise for entertaining, boating, water skiing, and fishing. Step inside to a bright interior that has been freshly painted top to bottom in a neutral color palette. The entire
Summer isn't over yet-there's still time to own your own slice of paradise at beautiful Lake Bungee! Nestled just a one-minute walk from the water, this charming retreat offers the perfect blend of relaxation and recreation. Step outside to a private backyard oasis designed for making memories, featuring a spacious patio, cozy fire pit, and plenty of room to entertain family and friends under the
Step back in time and discover the charm of this beautifully preserved 2,400 sq. ft. farmhouse, originally built in 1805. Rich in character and timeless appeal, this property offers the perfect blend of country living and modern convenience. Whether you dream of cultivating extensive gardens, raising animals, creating a self-sustaining homestead, or simply enjoying wide-open spaces, this property
Your seasonal escape is waiting at Meadowside of Woodstock - a private, gated 100-site co-op campground in Connecticut's Quiet Corner. Lot 69 features TWO structures: a 1999 40-foot Retreat park model with central air, new refrigerator, new deck, and new grill, PLUS a 12x16 log cabin on a concrete slab with electric fireplace and AC. Sleeps 6 total. Fully furnished including brand new sofa.
On a private road surrounded by unspoiled natural beauty, this remarkable 79-acre property offers exceptional privacy and endless potential. Two brooks enhance the landscape - Lebanon Brook along the western boundary and Porter Pond Brook to the east. The land features a mix of wetlands and highlands, heavily wooded with abundant timber resources. Create your secluded homestead in the wilderness
Discover the possibilities on this exceptional 100-acre parcel on Quarry Road in scenic Woodstock, Connecticut. Boasting approximately 1,900 feet of road frontage, this expansive property offers a rare combination of privacy, natural beauty, and development potential. The current owner has already cleared three beautiful potential building sites, each positioned to take advantage of the
Welcome to this stunning 2022-built Colonial set on 2.42 private acres in desirable Woodstock! Tucked back from the road and surrounded by nature, this beautifully maintained 3-bedroom, 2.5-bath home offers the perfect blend of modern comfort and peaceful country living. Step inside to an inviting open-concept layout featuring gleaming hardwood floors, recessed lighting, and abundant natural
Rare opportunity to secure the last premium homesite in one of Woodstock's most desirable areas, Eastwood Estates. This approved building lot is being offered as part of a custom home package with a local established builder. It is not being offered for sale as "land only" and requires a build contract with the designated builder, PMR Home Design and Expansion. Buyers may choose from thoughtfully
Adorable year-round home on Lake Bunggee, ideally located across from a private beach with stunning lake views. The main level features vaulted ceilings and an open-concept layout connecting the living room, dining area, and kitchen. There are two bedrooms on the main floor, along with a finished room on the lower level for added space. Enjoy not only the beautiful lake views but also a private
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
Welcome to this charming 2-bedroom, 1.5-bath home that offers the perfect blend of comfort and convenience. Ideal for empty nesters, downsizers, or anyone looking for a fantastic condo alternative, this home provides the privacy of single-family living without the hassle HOA. Step inside and enjoy a warm and inviting layout with comfortable living spaces that make the home feel instantly
Rare opportunity to own a large buildable lot in Woodstock, CT. This serene rear lot is located on one of the highest elevations in Woodstock. Surrounded by conservatory farmland, the views are for miles. The ride to this property, through the sparsely populated countryside, will surely give you the feel of the natural surroundings. Although located "far from the crowd" you are centrally located
Build your dream home near the lake! This unique offering includes two adjoining parcels being sold together for a combined total of approximately 0.7 acres. The primary 0.5-acre parcel features a beautiful cleared and level homesite with open grassy space, ideal for new construction. Previous perc testing and a site development plan in 2008 outlines proposed home placement, septic system, and
Enjoy the beautiful landscaping of this custom oversized ranch. Located on 6 acres, Recently cleared, private back yard perfect for entertaining, recreation and maybe a chicken or two. Double deck off the kitchen, that leads to above ground pool. This is your perfect summer spot! Kitchen with breakfast nook updated cabinets and stainless appliances, tile... Dining room follows kitchen to a one
Spacious 3-bedroom, 1-bath second-floor apartment located in a well-maintained mixed-use building. This unit offers a large, open layout featuring a bright kitchen with ample cabinet space, a combined dining area, and an expansive living room with plenty of natural light. Three bedrooms and a full bath completes the space. Private entrance with exterior stairs leading to the unit. Off-street
Stunning remodeled 4 bedroom, 2.5 bath lakefront home available for rent! This spacious residence boasts modern updates throughout, including a fully renovated kitchen with stainless steel appliances, stylish bathrooms, and fresh flooring. Enjoy breathtaking lake views from the largeopen floor plan and the screened in and open deck-perfect for relaxing or entertaining. With ample natural light, a
Very nice first floor unit with patio area. Hardwood floors in living room and both bedrooms. Kitchen is modern with newer cabinets and countertops. Stove and refrigerator is included. Ceramic tile floor. Bathroom has been remodeled with ceramic floor. Plenty of parking. Large yard. Great location in Woodstock. Laundry hookup is in the basement. Washer and dryer supplied by tenant. PETS ARE NOT
Brand-new multi-level TimberTech decks spanning roughly 800 square feet anchor the back of this fully furnished and beautifully renovated lakeside home on private Witches Woods Lake, creating an expansive outdoor haven for hosting, unwinding, and breathing in the calm of true waterfront living. With breathtaking views and direct frontage, the home has been thoughtfully updated in recent years
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