Woodstock Homes for Sale

Welcome to Woodstock, Connecticut—a charming town nestled in the scenic hills of Windham County. Known for its rich history and picturesque landscapes, Woodstock offers a unique blend of rural tranquility and community spirit, making it an ideal place for families, retirees, and anyone seeking a peaceful lifestyle. With its quaint New England charm, Woodstock is dotted with historic homes, lush green spaces, and vibrant local businesses.

As you explore the area, you’ll discover a wealth of outdoor activities, from hiking the beautiful trails of the nearby Mashamoquet Brook State Park to enjoying a leisurely afternoon at the charming local farms. The town hosts numerous community events throughout the year, fostering a sense of belonging and connection among residents.

For those considering a move to this idyllic town, there are a variety of homes for sale that cater to diverse tastes and budgets. Whether you’re looking for a cozy cottage, a spacious family home, or a luxurious estate, Woodstock’s real estate market has something for everyone. Many properties boast stunning views, ample outdoor space, and modern amenities while retaining that classic New England charm.

With its strong sense of community, excellent schools, and proximity to major highways, Woodstock is not just a place to live; it’s a place to thrive. Don’t miss the opportunity to make this enchanting town your new home. Explore the homes for sale in Woodstock today and discover the perfect blend of comfort and charm in this hidden gem of Connecticut!

Newest Woodstock Homes for Sale

$299,900

3 Beds ⋅ 1 Baths ⋅ 24194134 MLS

Adorable ranch located in desirable Woodstock, Connecticut! Offering over 1,200 square feet of comfortable one-level living, this charming home features three spacious bedrooms and one full bath. The updated eat-in kitchen opens directly to a bright three-season room, creating the perfect space to enjoy your morning coffee, relax, or entertain guests. The large living room features beautiful windows that fill the space with natural light, along with a convenient storage closet. The generously sized primary bedroom offers two walk-in closets, providing plenty of storage. A standout feature of this property is the oversized two-car attached garage, complete with high ceilings and ample room for vehicles, a workshop, additional storage, or the possibility of creating overhead loft space. Nestled on a peaceful half-acre lot, the property is surrounded by classic New England stone walls and mature trees that provide plenty of shade and privacy. This home offers a wonderful opportunity for buyers looking to add their own personal touches. While some updating and improvements may be desired, the property provides a functional layout, and plenty of potential to create a space that truly feels like home. This inviting Woodstock ranch is ready for its next owner to make it their own! Property is being sold as is where is. Highest and best due 07/28/2026 by 9 pm.

176 Joy Rd, Woodstock

$698,900

2 Beds ⋅ 3 Baths ⋅ 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

$75,000

2 Beds ⋅ 1 Baths ⋅ 24193441 MLS

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

$650,000

2 Beds ⋅ 3 Baths ⋅ 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

$625,000

1 Beds ⋅ 1 Baths ⋅ 24191228 MLS

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 home boasts brand-new wall-to-wall tile flooring with radiant heat that combines luxury with a high-durability lake-life utility. The open-concept layout flows seamlessly into a sunlit living space. Mini splits that provide heat and A/C and a newly installed gas fireplace designed to keep you cozy throughout the seasons. Exit through your sliders to your 19 x 33 outdoor high-end deck that extends your living space. It features motorized adjustable louvers that can be closed for complete shade or weather protection, as well as electric screens for insect protection.

4 Loyola Rd Extension, Woodstock

$279,000

2 Beds ⋅ 1 Baths ⋅ 24189592 MLS

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 stars. Inside, you'll find a bright, open-concept living space that feels warm and inviting, along with two comfortable bedrooms and a full bathroom. Whether you're looking for a peaceful weekend getaway, a seasonal escape, or a year-round home, this property is ready for you to start enjoying the lake lifestyle. Don't miss your opportunity to make every season feel like a vacation at Lake Bungee!

170 Laurel Hill Dr, Woodstock

$45,000

1 Beds ⋅ 1 Baths ⋅ 24188690 MLS

Welcome to Beautiful Meadowside of Woodstock Campground, a private, gated 100 site co-op campground in Connecticut's quiet Corner. Unit 29 features a 1998 Four Winds mobile home model 30fk and a 30 foot by 9.5 foot combination room added on to the front. The trailer has a kitchen, living room dining room combo with a pull out bed, full bath, and bed room. The addition had a bigger eating area and a family room. It is move in ready, fully furnished. Lot assessment of $1,650/ season (1,350 early-bird before Jan 31) covers water, sever, trash, grounds maintenance, and all amenities. Season runts from mid April through October

25 Rte 197 Rte Unit 29, Woodstock

$500,000

3 Beds ⋅ 2 Baths ⋅ 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

$699,000

3 Beds ⋅ 3 Baths ⋅ 24160903 MLS

Welcome to the Top of Connecticut's Last Green Valley. Views sweep across the east and soak up the sunrise every day from the peak of 12 acres that are exclusively yours. Peaceful adventure and native wildflowers beckon you to embrace it all. Step inside your renovated New England Farmhouse and let the home guide you: hand-hewn beams, wide-plank floors, leaded-glass windows, and a cozy working fireplace. The kitchen blends quartz-countertops and new stainless appliances with custom woodwork and an antique butcher-block island. Dine amongst the stars with a wide picture window at your service. The showpiece sunroom features an reclaimed palladian window and chandelier from a historic train station, walnut floors, and is wrapped in glass to bring the light and the view of the valley into every special moment. Around the corner, the Great Room gathers everyone for movies and games, and a finished lower level with full bath adds flexible room to grow. The upstairs bedrooms look out over the lawn and beyond. Major considerations are done: new roof and deck, newer boiler, pressure tank, fresh paint, and a generator hookup for assurance. A barn-style garage, and charming yet large garden sheds give you all the outdoor storage you need. And right out your back door: the town beach is 4 minutes away, a local winery is 5. Hiking, swimming, and frisbee golf at Crystal Pond Park, and the Woodstock Fair every fall. This is the one that you've always dreamed about. And it's here, now

29 Braaten Hill Rd, Woodstock

$1,275,000

4 Beds ⋅ 4 Baths ⋅ 24185273 MLS

This extraordinary waterfront estate on Chamberlain Lake offers a lifestyle rarely found in Connecticut. With 200ft of private lake frontage, this custom post-and-beam Cape was thoughtfully crafted using timber milled directly from trees harvested on the property, creating a residence that is as authentic as it is remarkable. A dramatic center chimney anchors the home, while wide-board pine floors, exposed beams, and walls of windows showcase breathtaking views. The primary suite features a private balcony overlooking the lake, two walk-in closets, and a spa-like bath. Generously sized rooms and oversized step-in closets throughout the home provide exceptional comfort and storage. A private entrance way will lead you to the lake to enjoy fishing, kayaking, canoeing, swimming and peaceful lake living await. Gather around the fire pits, enjoy the outdoor shower after a day on the water, or simply relax on the covered deck among professionally landscaped grounds. This exceptional property combines privacy, craftsmanship, recreation, and timeless New England beauty in one truly unforgettable offering.

95 Pole Bridge Rd, Woodstock

$290,000

2 Beds ⋅ 2 Baths ⋅ 24183795 MLS

Welcome to this beautiful lakeside retreat, ideally situated just a short walk from the private beach at Lake Bungee. Offering comfortable one-level living, this home features 2 bedrooms, one being a primary suite with a private bath and relaxing Jacuzzi tub. The bright and inviting floor plan includes a sun-filled sunroom, perfect for enjoying morning coffee or unwinding at the end of the day. This home also has a second full bathroom, open kitchen with bar style seating. Step outside to a spacious deck overlooking the oversized lot, offering plenty of room for entertaining, gardening, or simply enjoying the outdoors. Car enthusiasts and hobbyists will appreciate the oversized attached two-car garage with ample storage space. Whether you're looking for a year-round residence or a peaceful get away near the lake, this charming property combines comfort, convenience, and a desirable location with private beach access just moments away. Home is being sold in AS-IS condition

60 Lyon Rd, Woodstock

$625,000

3 Beds ⋅ 3 Baths ⋅ 24183359 MLS

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 provides endless opportunities to embrace a rural lifestyle. Mature landscaping, open grounds, and ample space for farming, hobby agriculture, or outdoor recreation make it a rare find for those seeking a connection to the land. Inside, you'll find the warmth and craftsmanship of a bygone era, with spacious living areas designed for comfortable everyday living and entertaining. Enjoy peaceful mornings overlooking your gardens and relaxing evenings surrounded by the tranquility of the countryside. Whether you're seeking a gentleman's farm, a luxury homestead, or a historic country estate to call home, this remarkable property presents a unique opportunity to live a lifestyle defined by beauty, self-sufficiency, and enduring New England character.

429 New Sweden Rd, Woodstock

Start Your Search

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed. © 2026 State-Wide Multiple Listing Service. All rights reserved. Data Last Updated:

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.