$486,844Average Value$277Average Price per Sq Ft13Homes 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
Gina Cavallo,
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.
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On average, homes in Woodstock, CT sell after 39 days on the market compared to the national average of 55 days. The median sale price for homes in Woodstock, CT over the last 12 months is $435,000, up 1% from the median home sale price over the previous 12 months.
Now offered for the spring market, this exceptional waterfront home on Witches Woods Lake is ready to be enjoyed in its most vibrant season. Set on nearly an acre with approximately 200 feet of direct waterfront, this 4-bedroom, 2-bath home offers 2,630 sq. ft. of inviting living space. The main level features a warm, functional layout with a stone fireplace, built-ins, sunroom, and a flexible
Enjoy this beautiful, like-new, well-cared for 2250 square foot 3 bedroom, 3 full bath home in picturesque Woodstock setting. Private but yet convenient to major routes. Home features hardwood floors on main level with an open floor plan. Eat in Kitchen has stainless steel appliances, granite countertops, tile backsplash and a gas range. Kitchen also features Cubitac white shaker style cabinets.
Welcome home to this beautifully maintained 3-bedroom, 1-bath residence nestled on a generous half-acre lot. Perfectly situated for privacy and room to roam, the expansive yard offers endless possibilities-whether you dream of a lush garden, a fire-pit or gathering spot. Step inside and be greeted by warm hardwood floors that flow seamlessly throughout the entire home, creating a bright, cohesive
House was withdrwan due to bad winter weather only. Historic elegance meets modern comfort in the Ebenezer Stoddard House (c. 1800), a former inn offering 4,172 sq ft, 5 bedrooms, and 3.5 baths on 1.2 acres in Woodstock's sought-after Quiet Corner. Original charm shines through wide-plank floors, exposed beams, multiple fireplaces, 2 stair cases , while recent updates include a modernized kitchen
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
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
Now offered for the spring market, this exceptional waterfront home on Witches Woods Lake is ready to be enjoyed in its most vibrant season. Set on nearly an acre with approximately 200 feet of direct waterfront, this 4-bedroom, 2-bath home offers 2,630 sq. ft. of inviting living space. The main level features a warm, functional layout with a stone fireplace, built-ins, sunroom, and a flexible
Set in the charming town of Woodstock and minutes from the Massachusetts line, this 3-bedroom, 2.5-bath home offers space, flexibility, and a layout ideal for both everyday living .The home includes two primary suites- rare find! Inside, you'll find a spacious living room with vaulted ceilings and a propane fireplace, creating a warm and inviting focal point. The large kitchen features abundant
Enjoy this beautiful, like-new, well-cared for 2250 square foot 3 bedroom, 3 full bath home in picturesque Woodstock setting. Private but yet convenient to major routes. Home features hardwood floors on main level with an open floor plan. Eat in Kitchen has stainless steel appliances, granite countertops, tile backsplash and a gas range. Kitchen also features Cubitac white shaker style cabinets.
Welcome home to this beautifully maintained 3-bedroom, 1-bath residence nestled on a generous half-acre lot. Perfectly situated for privacy and room to roam, the expansive yard offers endless possibilities-whether you dream of a lush garden, a fire-pit or gathering spot. Step inside and be greeted by warm hardwood floors that flow seamlessly throughout the entire home, creating a bright, cohesive
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
Welcome to this charming colonial with stenciled details that add character & style! This delightful antique property is the perfect fixer upper and features 3 bedrooms, 1 and a 1/2 bathrooms, and a clapboard exterior. Situated on a 0.9 acre lot, this home boasts a garden in the side yard and a large backyard, perfect for outdoor enjoyment. Additionally, a shed provides convenient storage for
Exceptional pride of ownership is evident in this rare opportunity to acquire a 14-unit multifamily asset in Woodstock, CT, with the option to combine with an additional 14 units at Pinecrest Apartments for portfolio sale. Built in 1987, the property features tenant-paid utilities with individual hot water heaters and electrical subpanels in every unit-supporting efficient operations and strong,
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
On a private road with Unspoiled Splendor - 79 Acres with 2 brooks on the property. Lebanon Brook on the west side and Porter Pond brook on the east. Some wetlands mixed with some highlands and lots of trees. Absolute seclusion possibe with enough lumber to build and heat your home forever. Carve your homestead out of the Wilderness amongst other large acreage parcels. 300' Road Frontage on Ide
Property Id: 2430022I have a large victorian home from the 1800's set in rural Woodstock, CT. Room rentals are available on a monthly term, no lease. All utilities are included, with laundry facilities available aa well as a fully furnished kitchen. Perfect for travel nurses and other traveling professionals needing short term accommodations. Boston is two hours away. Prividence is one
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
Woodstock 3-bedroom 1 bathroom Ranch rental, conveniently located for commuting. Sitting on 3/4 AC, this home features new roof, efficient solar panels for low electric bills, brand new well, along with cosmetic updates to the kitchen, bathroom, and bedrooms. Home has a good sized attached 2 car garage/workshop/storage area along with a full basement for additional storage. Paved driveway with
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