Windham, CT Homes

• 

  $530,000 Sold Jun 13, 2025

  • 1,826 Sq Ft
  • $290/SF
  • 33 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1840

  577 Route 197, Woodstock, CT 06281

  Welcome to this lovingly maintained 1840s farmhouse. Enjoy the large living room with skylights and plenty of windows to bring in the natural light, as well as a wood burning stove to keep you cozy on cold winter nights. Master bedroom and large ensuite can be found on the first floor, along with a cozy bright kitchen, dining room and office/den. Make your way upstairs to an updated bathroom and

  Jacqueline Kapusta Navick Properties LLC

  577 Route 197, Woodstock, CT 06281
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• 

  Est $354,504 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,340 Sq Ft

  80 Barlow Cemetery Rd, Woodstock Valley, CT 06282

  80 Barlow Cemetery Rd, Woodstock Valley, CT 06282
• 

  

  

  /15

  $299,999

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft

  566 Route 197, Woodstock, CT 06281

  Welcome to this charming home! This recently renovated home is move in ready! Sitting on a small, but usable, 0.2 acre fenced-in lot, this 3 bedroom, 1.5 bathroom home is ready for immediate occupancy. The home is approximately 1,400 sq. ft. with spacious rooms & bedrooms. On the first floor, you'll find kitchen has been tastefully updated with updated cabinets, countertops, backsplash &

  Skyla Gagnon RE/MAX Bell Park Realty

  566 Route 197, Woodstock, CT 06281
• 

  $330,000 Sold Jun 12, 2025

  • 1,300 Sq Ft
  • $254/SF
  • 39 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1960

  27 Meehan Rd, Woodstock, CT 06281

  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

  Jamie Meadows William Raveis Real Estate

  27 Meehan Rd, Woodstock, CT 06281
• 

  Est $641,605 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,316 Sq Ft

  189 New Sweden Rd, Woodstock, CT 06281

  189 New Sweden Rd, Woodstock, CT 06281
• 

  

  /34

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 2,362 Sq Ft

  359 Barlow Cemetery Rd, Woodstock, CT 06281

  Welcome to 359 Barlow Cemetery Rd - a truly one-of-a-kind property set on 3.2 scenic acres that lead to the peaceful waters of Bungee Brook. This spacious home offers a versatile layout, featuring a large primary bedroom suite, two additional bedrooms, and a generous supplemental room on the upper level-perfect for a home office, gym, or guest space. The fully finished basement is an

  Adam Gumula Kazantzis Real Estate, LLC

  359 Barlow Cemetery Rd, Woodstock, CT 06281
• 

  $49,900 Sold Jun 12, 2025

  • Land
  • 3.60 Acres
  • $13,861 per Acre

  • 305 Days On Market

  XOXO Connecticut 169, Woodstock, CT 06281

  Approved oversized 3.6 acre subdivision lot features privacy & room to roam! For space & protection, this land boasts 396' of road frontage (36' longer than the length of a football field including both end zones)! Horses & ATVs OK. Road frontage boundaries are flagged with ribbons, bordering homes 1310 RT 169, the neighbor to the south, at the corner of stonewall, which further runs west as this

  Dennis Duga Northeast Realty

  XOXO Connecticut 169, Woodstock, CT 06281
• 

  Est $484,467 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,658 Sq Ft

  398 Brickyard Rd, Woodstock, CT 06281

  398 Brickyard Rd, Woodstock, CT 06281
• 

  

  /5

  $299,000 Open Sun 11AM - 1PM

  • 2 Beds
  • 1.5 Baths
  • 1,196 Sq Ft

  10 Laurel Hill Dr, Woodstock Valley, CT 06282

  LOCATION, LOCATION, LOCATION!!!! This cozy 2-3 bedroom ranch is nestled on .40 of an acre lot with views of Lake Bunggee. Lake Bunggee is a private lake association for residents only. Access to the beach and boat launch is across the street. The roof is only 10 years old, electrical was updated and new wood decks on each side of the home. One floor living including a woodburning fireplace for

  Simonne Corriveau KW Legacy Partners

  10 Laurel Hill Dr, Woodstock Valley, CT 06282
• 

  $445,000 Sold Jun 10, 2025

  • 1,708 Sq Ft
  • $261/SF
  • 92 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1960

  1015 Route 198, Woodstock, CT 06281

  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,

  Amy Vinal Pine Knoll Real Estate

  1015 Route 198, Woodstock, CT 06281
• 

  Est $364,136 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,874 Sq Ft

  3 Route 197, Woodstock, CT 06281

  3 Route 197, Woodstock, CT 06281
• 

  

  /31

  $1,250,000

  • 3 Beds
  • 2.5 Baths
  • 3,983 Sq Ft

  584 Prospect St, Woodstock, CT 06281

  For those who belong to the land. Over 100 acres of private, usable terrain at the CT/MA line, Bear Hill Estate is a fully realized lifestyle retreat for the discerning equestrian or outdoor enthusiast, with effortless access to I-395, I-84, and the Mass Pike. At its heart sits a 3 bed, 2.5 bath custom log home-crafted from white pine logs hand-felled in Nova Scotia, where the bespoke cabinetry

  Jennie Kesselman Berkshire Hathaway NE Prop.

  584 Prospect St, Woodstock, CT 06281
• 

  $280,000 Sold Jun 09, 2025

  • 1,098 Sq Ft
  • $255/SF
  • 48 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1985

  26 Woodstock Meadows, Woodstock, CT 06281

  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.

  Mark Benard Brunet and Company Real Estate

  26 Woodstock Meadows, Woodstock, CT 06281
• 

  Est $433,738 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft

  45 Center Rd, Woodstock, CT 06281

  45 Center Rd, Woodstock, CT 06281
• 

  

  /39

  $1,250,000

  • 2 Beds
  • 2 Baths
  • 2,340 Sq Ft

  1669 Route 169, Woodstock, CT 06281

  Welcome to Hilltop Meadows-a one-of-a-kind, 60-acre luxury hay farm nestled in Connecticut's scenic "Quiet Corner." Set high above Route 169 in North Woodstock, this breathtaking property offers rolling meadows, mature forests, and serene privacy just 60 miles from Boston and 150 from Manhattan. The heart of the property is a newly updated 2-bed, 2-bath, 2,340 sq ft farmhouse blending historic

  Ryan De Lello William Pitt Sotheby's Internatiomal Realty

  1669 Route 169, Woodstock, CT 06281
• 

  $305,000 Sold Jun 04, 2025

  • 2,086 Sq Ft
  • $146/SF
  • 153 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2003

  1796 Route 197 Unit A, Woodstock, CT 06281

  Back on market & price reduced below appraised value! Most affordable living in Woodstock, CT! The unit is in fantastic condition and at less than $150 a sf, offers more value than an any detached home. Discover the perfect blend of comfort and nature in this 3 bed/2.5 bath half duplex home. Featuring gleaming hardwood floors throughout the first floor, a cozy wood burning fireplace, & large

  Valerie MacNeil Kazantzis Real Estate, LLC

  1796 Route 197 Unit A, Woodstock, CT 06281
• 

  Est $467,826 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,938 Sq Ft

  14 Applewood Dr, Woodstock, CT 06281

  14 Applewood Dr, Woodstock, CT 06281
• 

  

  /30

  $64,900

  • 2 Beds
  • 1 Bath
  • 450 Sq Ft

  91 Meadowside Rd, Woodstock, CT 06281

  Welcome to Beautiful Meadowside of Woodstock Campground, your home away from home! This is a rare opportunity to own your very own campsite along with the 1991 Mallard 38' x 140" x 12' Model with a Custom built sunroom attached located in the back of the campground. Enjoy the peace and serenity of nature. The camper is made up of 2 full/queen beds, the full bathroom is spacious with a tub, toilet

  Kerri Mullen CR Premier Properties

  91 Meadowside Rd, Woodstock, CT 06281
• 

  $670,000 Sold May 30, 2025

  • 2,970 Sq Ft
  • $226/SF
  • 33 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1990

  234 Route 197, Woodstock, CT 06281

  Set on a peaceful and private nearly 3-acre lot, this custom-built home is absolutely stunning-with a truly remarkable story. Thoughtfully designed and built by Richard "Butch" Johnson-five-time Olympian and member of the U.S. archery teams that brought home gold-this property is a testament to high-end craftsmanship and care. Beautiful hardwood floors and cathedral ceilings flow throughout,

  Trisha White Rosehaven Real Estate, LLC

  234 Route 197, Woodstock, CT 06281
• 

  Est $521,111 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,196 Sq Ft

  932 Route 169, Woodstock, CT 06281

  932 Route 169, Woodstock, CT 06281
• 

  

  /27

  $285,000

  • 2 Beds
  • 1 Bath
  • 1,125 Sq Ft

  28 Oak Dr, Woodstock Valley, CT 06282

  LAKE LIFE IN WOODSTOCK. This charming year-round home in Woodstock, CT, offers a unique opportunity to embrace a peaceful lake lifestyle. Built in 1955, the residence sits on a generous 1.1-acre multi-tiered lot, providing ample privacy and seasonal lake views. KEY FEATURES: Deeded Beach Rights: Enjoy direct access to Bungee Lake with deeded beach rights, including access to association beaches

  Donna Copeland William Raveis Real Estate

  28 Oak Dr, Woodstock Valley, CT 06282
• 

  $88,000 Sold May 29, 2025

  • Land
  • 2.37 Acres
  • $37,131 per Acre

  • 56 Days On Market

  00 Child Rd, Woodstock, CT 06281

  Build your dream house on this beautiful, treed lot, sloped to Chamberlin Pond. Direct, waterfront access to pond, which is a non-motorized body of water. Some light grading work required to create a level building lot overlooking a natural and remote lake.

  Gary Pruitt Century 21 Classic Homes

  00 Child Rd, Woodstock, CT 06281
• 

  Est $560,582 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,960 Sq Ft

  896 Route 198, Woodstock, CT 06281

  896 Route 198, Woodstock, CT 06281
• 

  

  /37

  $559,000

  • 4 Beds
  • 2.5 Baths
  • 2,150 Sq Ft

  101 Child Hill Rd, Woodstock, CT 06281

  Welcome to this beautiful & idyllic colonial, sitting off of Woodstock Hill! The views are outstanding! This home is known as the " White House" by the locals and in walking distance to the Academy!Drive up the long paved driveway and walk up the stairs to an expansive NEW TREX decking overlooking the countryside. Step inside the remodeled kitchen where you have an inset window seat, with higher

  Skyla Gagnon RE/MAX Bell Park Realty

  101 Child Hill Rd, Woodstock, CT 06281
• 

  $650,000 Sold May 27, 2025

  • 2,952 Sq Ft
  • $220/SF
  • 20 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1996

  26 Center Rd, Woodstock, CT 06281

  Oversized Colonial home with recent central air installation, freshly painted and gleaming hardwood floors is move in ready. This home offers all hobbyists the best space and storage. There is 3 car massive garage with an additional walk-up attic storage space as well as an additional garage bay for all the yard equipment. The home offers plenty of privacy with it's 3.5 acre wooded lot. The

  Conrad Allen RE/MAX Professional Associates

  26 Center Rd, Woodstock, CT 06281
• 

  Est $446,695 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,946 Sq Ft

  320 Pulpit Rock Rd, Woodstock, CT 06281

  320 Pulpit Rock Rd, Woodstock, CT 06281
• 

  

  /36

  $575,000

  • 4 Beds
  • 2.5 Baths
  • 2,016 Sq Ft

  104 Pulpit Rock Rd, Woodstock, CT 06281

  This 4 Bedroom 2.5 bath meticulously maintained Colonial style home offers a seamless blend of classic charm and modern comfort creating an inviting and functional living environment. High ceilings and abundant natural light illuminate the rich engineered wood floors and detailed crown molding throughout. Enjoy this beautiful kitchen featuring custom Brunarhans cabinetry and granite countertops,

  Belinda Culp Berkshire Hathaway NE Prop.

  104 Pulpit Rock Rd, Woodstock, CT 06281
• 

  $419,000 Sold May 19, 2025

  • 1,688 Sq Ft
  • $248/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1964

  235 Senexet Rd, Woodstock, CT 06281

  Life is better near the lake! Look no further than this well-built and maintained ranch with 3 bedrooms and 2 full bathrooms just down the street from Roseland Lake. Cozy up to the wood-burning fireplace in the living room, or entertain in the amazing sunroom with high ceilings, exposed beams, ceiling fan, and a wood stove; this space is an absolute joy! The back yard is equally as suited to

  Chad Glucksman KW Legacy Partners

  235 Senexet Rd, Woodstock, CT 06281
• 

  Est $621,288 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,270 Sq Ft

  228 County Rd, Woodstock, CT 06281

  228 County Rd, Woodstock, CT 06281
• 

  

  /39

  $1,986,000

  • 4 Beds
  • 3.5 Baths
  • 5,104 Sq Ft

  175 Pulpit Rock Rd, Woodstock, CT 06281

  A once-in-a-generation opportunity. Please visit this stunning Georgian estate situated on 55 hilltop acres in desirable Woodstock, CT. Enjoy breathtaking long views all the way to Rhode Island! A few of the exceptional assets offered include an elegant in-law apartment, a large 6 stall horse barn with office, an inviting in-ground pool, and 25 acres of fenced open pasture. As you approach the

  John Downs Berkshire Hathaway NE Prop.

  175 Pulpit Rock Rd, Woodstock, CT 06281
• 

  $331,500 Sold Apr 25, 2025

  • 1,583 Sq Ft
  • $209/SF
  • 94 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1895

  54 Rawson Rd, Woodstock, CT 06281

  1890"s colonial on a quiet road in Woodstock. Updated bathrooms and kitchen. New carpet in living room and hardwood floors have been refinished. New gas furnace and baseboard radiators. New roof and electrical panel.Waiting for your finishing touches.

  Margaret Young CR Premier Properties

  54 Rawson Rd, Woodstock, CT 06281
• 

  Est $462,524 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,275 Sq Ft

  4 Barber Rd, Woodstock, CT 06281

  4 Barber Rd, Woodstock, CT 06281
• 

  

  /23

  $29,900

  • 1 Bed
  • 1 Bath
  • 300 Sq Ft

  25 Route 197 Unit Lot 40, Woodstock, CT 06281

  Price Improvement! 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

  Keri Roy Kazantzis Real Estate, LLC

  25 Route 197 Unit Lot 40, Woodstock, CT 06281
• 

  $430,000 Sold Apr 17, 2025

  • 1,920 Sq Ft
  • $224/SF
  • 11 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  855 Brickyard Rd, Woodstock, CT 06281

  This home is a transformed Saltbox into a "modern Farmhouse style" show piece! Kitchen has all the bells and whistles of granite to shiplap ceilings. Black windows accent the white kitchen walls, ornate tiles, and open shelving. Whitewashed fireplace is a focal point in the open dining room. New flooring throughout flows giving a grand feel to the open space. Large living room with a second

  Amy Brunet Brunet and Company Real Estate

  855 Brickyard Rd, Woodstock, CT 06281
• 

  Est $428,617 Not Listed For Sale

  • 8 Beds
  • 4 Baths
  • 2,904 Sq Ft

  189 Paine District Rd, Woodstock, CT 06281

  189 Paine District Rd, Woodstock, CT 06281
• 

  /2

  $99,900

  • Land
  • 12 Acres
  • $8,325 per Acre

  00 Prospect St, Woodstock, CT 06281

  Discover the perfect canvas for your dream home or private retreat on this stunning 12-acre parcel located in scenic Woodstock, Connecticut. This unique piece of land offers a peaceful setting with a blend of rolling topography, mature trees, and a beautiful pond-ideal for nature lovers, homesteaders, or anyone seeking privacy and serenity. The land features varied elevations, providing

  Mateusz Chojnicki CR Premier Properties

  00 Prospect St, Woodstock, CT 06281
• 

  $440,000 Sold Apr 11, 2025

  • 2,086 Sq Ft
  • $211/SF
  • 38 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2013

  47 Tayler Trail, Woodstock Valley, CT 06282

  A classic farmer's porch welcomes you home to this BETTER than new construction with a first floor primary BR in idyllic Woodstock! Tucked away on just over a 3/4 acre lot, virtually every inch of this property has been updated. Enter to a sunplashed open floorplan with gleaming hardwood floors and fresh paint. Brand new, high-style kitchen with granite peninsula, chic blue cabinetry, and new S/S

  Tommy Connors Redfin Corporation

  47 Tayler Trail, Woodstock Valley, CT 06282
• 

  Est $438,021 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,962 Sq Ft

  417 Dugg Hill Rd, Woodstock, CT 06281

  417 Dugg Hill Rd, Woodstock, CT 06281
• 

  /2

  $99,000

  • Land
  • 10 Acres
  • $10,270 per Acre

  0 Rt 198, Woodstock, CT 06281

  This beautiful laurel-rich hard and soft wood land has wide frontage on CT 198 and on town road Pole Bridge Road, making this an easily accessible home sites. Property is sold AS-IS, contingent on clear title. There is a special permit for a commercial Building. Septic plan and building design are at the Town Hall. Please note: there is not yet driveway access to this property.

  Nicole Gleason CR Premier Properties

  0 Rt 198, Woodstock, CT 06281
• 

  $1,075,000 Sold Mar 24, 2025

  • 5,264 Sq Ft
  • $204/SF
  • 44 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1994

  40 Town Farm Rd, Woodstock, CT 06281

  Private and tranquil, compound on 6.92 Acres this Country Style Estate is Extraordinary! A tree-lined private driveway sets the serene tone for this exceptional property. The main living areas are dramatic yet comfortable and all have a connection to each other as well as the outdoor living spaces, which include a koi pond and waterfall, patios, decks and outdoor living spaces. Recent upgrades

  Kevin Brignole Spaulding Realty Group, LLC

  40 Town Farm Rd, Woodstock, CT 06281

Showing Results 41 - 80, Page 2 of 18