Windham, CT Homes

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  /40

  $649,900

  • 4 Beds
  • 2.5 Baths
  • 2,682 Sq Ft

  37 Pulpit Rock Rd, Woodstock, CT 06281

  Location, location, location! Tucked away on a quiet scenic road just steps from historic Woodstock Hill and Woodstock Academy, this classic Colonial offers 2,682 sq. ft. of timeless charm on 1.6 acres-one of the most desirable and private settings in Woodstock. Inside, wide-plank oak floors, exposed beams, and two fireplaces create a warm and inviting atmosphere. The open kitchen and dining

  

  Carol Ryniewicz

  CR Premier Properties

  (860) 854-3110

  37 Pulpit Rock Rd, Woodstock, CT 06281
• 

  Explore Outlying Woodstock

• 

  $250,000 Sold Jul 25, 2025

  • 1,954 Sq Ft
  • $128/SF
  • 3 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1979

  298 Child Rd, Woodstock, CT 06281

  Great property for Investor or Flipper this home has potential galore. The home sits on a spacious 2.4 acre lot. This home is going to need renovation and will not qualify for VA or Government financing unless it is a renovation loan. This home is in year 6 of a 25 year solar lease which will need to be transferred to buyer. The home is being sold "As Is" "Where Is". The estate has no funds to

  Rich Marouski Weichert,REALTORS-Four Corners

  298 Child Rd, Woodstock, CT 06281
• 

  Not Listed For Sale

  0 Shields Rd, Woodstock, CT 06281

  0 Shields Rd, Woodstock, CT 06281
• 

  

  

  /12

  $235,000

  • Land
  • 5 Acres
  • $45,988 per Acre

  00 Joy Rd, Woodstock, CT 06281

  "Life is a Joy on Joy Road" Nestled in the heart of Woodstock, CT, this stunning 5.11-acre building lot offers the perfect balance of peaceful seclusion and easy access to modern conveniences. Surrounded by lush woodlands and gently rolling terrain, this property provides an idyllic setting for your dream home, offering privacy, natural beauty, and a connection to nature. Despite its serene

  

  Elizabeth Scranton

  Kazantzis Real Estate, LLC

  (860) 846-4563

  00 Joy Rd, Woodstock, CT 06281
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  /38

  $677,000 Sold Jul 25, 2025

  • 2,132 Sq Ft
  • $318/SF
  • 9 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1978

  696 Connecticut 197, Woodstock, CT 06281

  Scenic Retreat Property with Stunning Landscaping - Discover this beautifully maintained horse property set on 19.9 acres of lush, landscaped grounds. Enjoy mature trees, colorful gardens, and peaceful outdoor spaces, perfect for relaxing or entertaining. The charming 2-bedroom, 2.5-bathroom home offers modern comforts, stunning craftsmanship, open living spaces with oversized windows and

  The Schlesman Realty Group ERA Key Realty Services

  696 Connecticut 197, Woodstock, CT 06281
• 

  Est $690,955 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,076 Sq Ft

  429 Child Rd, Woodstock, CT 06281

  429 Child Rd, Woodstock, CT 06281
• 

  

  /40

  $683,500 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,140 Sq Ft

  115 Center Rd, Woodstock, CT 06281

  Nestled on a picturesque 3.7-acre corner parcel, this well-maintained 2000-built ranch provides 2,140 sq ft of single-level living. A cathedral-ceiling great room unites the floor plan with continuous hardwood flooring and a striking floor-to-ceiling brick fireplace. The kitchen showcases quartz counters and stainless-steel appliances and opens to a generous dining area that blends seamlessly

  

  Carol Ryniewicz

  CR Premier Properties

  (860) 809-5700

  115 Center Rd, Woodstock, CT 06281
• 

  $325,000 Sold Jul 25, 2025

  • 1,296 Sq Ft
  • $251/SF
  • 8 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1982

  1534 Route 171, Woodstock Valley, CT 06282

  LOCATION, LOCATION! Right on Mass line and. Close to RI sits this PRIVATE COUNTRY CAPE on 5 ACRES! OVERSIZED 1 car garage (18 x 24) w/ attached breezeway w/ laundry room next to BRIGHT open appliance kitchen w/ BRAND NEW GRANITE counters, skylight for natural light in dining area leads to large 12 x 18 deck for entertaining. HARDWOOD floors in spacious living room w/ wood stove for second source

  Christine Johnson RE/MAX One

  1534 Route 171, Woodstock Valley, CT 06282
• 

  Est $628,572 Not Listed For Sale

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

  170 Lyon Hill Rd, Woodstock, CT 06281

  170 Lyon Hill Rd, Woodstock, CT 06281
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  /11

  $925,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 3,500 Sq Ft

  0 Joy Rd, Woodstock, CT 06281

  Luxury Ranch-Style Home To Be Built by DHS Copeland Builders - Woodstock, Ct Offered on a Private 5-Acre Parcel - Bring Your Plans or Use Ours! Discover the perfect blend of elegance and tranquility with this to-be-built luxury ranch-style home by the renowned DHS Copeland Builders. Centrally located in the heart of Woodstock, CT, this rare 5-acre parcel offers the ideal canvas for your dream

  

  Elizabeth Scranton

  Kazantzis Real Estate, LLC

  (860) 813-2921

  0 Joy Rd, Woodstock, CT 06281
• 

  $677,000 Sold Jul 25, 2025

  • 2,132 Sq Ft
  • $318/SF
  • 7 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1978

  696 Route 197, Woodstock, CT 06281

  Scenic Retreat Property with Stunning Landscaping - Discover this beautifully maintained horse property set on 19.9 acres of lush, landscaped grounds. Enjoy mature trees, colorful gardens, and peaceful outdoor spaces, perfect for relaxing or entertaining. The charming 2-bedroom, 2.5-bathroom home offers modern comforts, stunning craftsmanship, open living spaces with oversized windows and

  The Schlesman Realty Group ERA Key Realty Services

  696 Route 197, Woodstock, CT 06281
• 

  Est $698,135 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,832 Sq Ft

  28 Prospect St, Woodstock, CT 06281

  28 Prospect St, Woodstock, CT 06281
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  /16

  $895,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 3,356 Sq Ft

  36 Olde Meadow Rd, Woodstock, CT 06281

  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

  

  Tina Lajoie

  William Raveis Real Estate

  (860) 374-2832

  36 Olde Meadow Rd, Woodstock, CT 06281
• 

  $587,000 Sold Jul 21, 2025

  • 3,456 Sq Ft
  • $170/SF
  • 200 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1740

  50 Perrin Rd, Woodstock, CT 06281

  Set on a beautiful and quiet New England roadway, this 1740 antique home is a game changer for those looking for a property that can accommodate small animals! Currently the home for incredibly happy alpacas, sheep, and chickens! The 9 acres are mostly open and include a back pasture and a fenced area, run in and hay barn. There is an inground pool and detached 2-car garage, plus a small building

  Stephanie Gosselin CR Premier Properties

  50 Perrin Rd, Woodstock, CT 06281
• 

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,450 Sq Ft

  1656 Route 171, Woodstock Valley, CT 06282

  1656 Route 171, Woodstock Valley, CT 06282
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  /8

  $597,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,212 Sq Ft

  0 Rr 197 Rd, Woodstock, CT 06281

  Brand New Construction at an amazingly affordable price! This 4 bedroom 2.5 Colonial will be set on a knoll in the meadows in the picturesque Town of Woodstock. It is private and secluded, yet minutes away from the interstate with easy access to Boston, Worcester and Hartford. The home will have gleaming hardwood oak floors throughout the first floor with an open concept plan. The kitchen will

  

  Morris Lewis

  Northeast Realty

  (860) 943-4776

  0 Rr 197 Rd, Woodstock, CT 06281
• 

  $565,000 Sold Jul 18, 2025

  • 1,952 Sq Ft
  • $289/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1991

  222 Route 197, Woodstock, CT 06281

  Tucked away on nearly five acres of natural beauty, this Cape Cod charmer invites you to slow down, breathe deeply, and savor the life you've dreamed about. With 3 bedrooms, 2 full baths, and over 1,950 square feet that live far larger, this home offers the perfect blend of comfort and space to stretch out-both inside and out. Wake up with coffee on the oversized deck as morning light filters

  Brooke Gelhaus Compass Connecticut, LLC

  222 Route 197, Woodstock, CT 06281
• 

  Est $494,452 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,944 Sq Ft

  21 Deer Meadow Ln, Woodstock, CT 06281

  21 Deer Meadow Ln, Woodstock, CT 06281
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  /40

  $715,000

  • 4 Beds
  • 3.5 Baths
  • 4,536 Sq Ft

  101 Center Rd, Woodstock, CT 06281

  This beautiful sprawling custom colonial is set on 9 acres of land at the end of a winding long driveway and surrounded by open area. Grand living spaces with cathedral ceilings and a floor to ceiling fireplace, tons of natural light, 4 bedrooms & 3.5 bathrooms, a 1500 sqft in-law suite with additional bedroom, new appliances, spacious 2 car garage, and an out building with electricity and

  Jeff Valentine William Pitt Sotheby's Int'l

  101 Center Rd, Woodstock, CT 06281
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  /24

  $49,900 Sold Jul 13, 2025

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

  • 58 Days On Market

  1340B 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 Dr. LAND

  1340B Connecticut 169, Woodstock, CT 06281
• 

  Est $540,093 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,740 Sq Ft

  593 Brickyard Rd, Woodstock, CT 06281

  593 Brickyard Rd, Woodstock, CT 06281
• 

  

  /40

  $599,900

  • 5 Beds
  • 3.5 Baths
  • 4,172 Sq Ft

  4 Perrin Rd, Woodstock, CT 06281

  Welcome to the exquisite Ebenezer Stoddard house built in 1800 once an inn for travelers on an early state route. This 4100 sq ft home is filled with character, history and updates for modern convenience, while saving the historic charm! The home resides on an 1.2 acre lot, mostly cleared with plenty of room for family gatherings of any size! Entering the home into an official mudroom - leave

  Kerri Mullen CR Premier Properties

  4 Perrin Rd, Woodstock, CT 06281
• 

  $476,500 Sold Jul 11, 2025

  • 2,125 Sq Ft
  • $224/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1832

  18 Perrin Rd, Woodstock, CT 06281

  OPEN HOUSE CHANGED TO SUNDAY JUNE 1 11-1 Charming Antique Home on 2.7 manicured acres in Woodstock. Step into timeless elegance with this beautifully maintained home. Bursting with character and modern comforts, this 3 bedroom, 2 full bath residence offers an inviting blend of old world charm and thoughtful updates. Inside, you'll find a graceful flow of living spaces, including a formal living

  Amy Archambault CR Premier Properties

  18 Perrin Rd, Woodstock, CT 06281
• 

  Est $407,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  538 Center Rd, Woodstock, CT 06281

  538 Center Rd, Woodstock, CT 06281
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  /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
• 

  $500,000 Sold Jul 07, 2025

  • 2,266 Sq Ft
  • $221/SF
  • 92 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1850

  519 Route 169, Woodstock, CT 06281

  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

  Stephanie Gosselin CR Premier Properties

  519 Route 169, Woodstock, CT 06281
• 

  Est $642,500 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,920 Sq Ft

  214 Woodstock Rd, Woodstock, CT 06281

  214 Woodstock Rd, Woodstock, CT 06281
• 

  

  /40

  $679,000

  • 3 Beds
  • 2 Baths
  • 2,669 Sq Ft

  402 Perrin Rd, Woodstock, CT 06281

  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

  Kelly Ryan William Raveis Real Estate

  402 Perrin Rd, Woodstock, CT 06281
• 

  $670,000 Sold Jun 30, 2025

  • 2,722 Sq Ft
  • $246/SF
  • 7 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2003

  133 Calkins Rd, Woodstock, CT 06281

  133 Calkins Road, Woodstock, offers a unique blend of classic charm and modern updates. This 3-bedroom, 2.5-bathroom home sits on a picturesque 2.14-acre lot, providing ample space for outdoor enjoyment. The exterior presents a traditional colonial style, while the interior reveals a custom design that sets it apart from typical homes in the area. The property's meticulous landscaping is

  Jennifer Jackson Berkshire Hathaway NE Prop.

  133 Calkins Rd, Woodstock, CT 06281
• 

  Est $389,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,516 Sq Ft

  30 Windswept Dr, Woodstock, CT 06281

  30 Windswept Dr, Woodstock, CT 06281
• 

  

  /40

  $799,000 Pending

  • 3 Beds
  • 4 Baths
  • 2,323 Sq Ft

  223 Barlow Cemetery Rd, Woodstock, CT 06281

  Discover modern luxury living in this stunning 2011-built Colonial. Perfectly situated on a picturesque waterfront lot with privately owned pond frontage, this thoughtfully designed home offers a lifestyle of elegance and comfort. The home offers 3 bedrooms, two full baths, and two half baths. You will love the classic oak flooring, crown molding, and light-filled living spaces. The finished

  John Downs Berkshire Hathaway NE Prop.

  223 Barlow Cemetery Rd, Woodstock, CT 06281
• 

  $400,000 Sold Jun 20, 2025

  • 1,452 Sq Ft
  • $275/SF
  • 2 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1981

  53 Andrews Rd, Woodstock, CT 06281

  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

  Kristen Kaskela Berkshire Hathaway NE Prop.

  53 Andrews Rd, Woodstock, CT 06281
• 

  Est $429,679 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,522 Sq Ft

  107 Barber Rd, Woodstock, CT 06281

  107 Barber Rd, Woodstock, CT 06281
• 

  

  /40

  $998,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,797 Sq Ft

  40 Shields Rd, Woodstock, CT 06281

  Welcome to 40 Shields Road, an exquisite reproduction nestled in the heart of desirable Woodstock, Connecticut. This stunning property seamlessly blends timeless craftsmanship with modern efficiency, offering perfect one-floor living. The home features wide pine floors throughout, custom hand-crafted built-ins, and a beautiful cherry and soapstone Brunarhans kitchen with high-end appliances.

  John Downs Berkshire Hathaway NE Prop.

  40 Shields Rd, Woodstock, CT 06281
• 

  $28,500 Sold Jun 17, 2025

  • 920 Sq Ft
  • $31/SF
  • 49 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1990

  25 Connecticut 197, Woodstock, CT 06281

  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,

  Melanie Taylor Berkshire Hathaway NE Prop.

  25 Connecticut 197, Woodstock, CT 06281
• 

  Est $387,973 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,310 Sq Ft

  31 Rawson Rd, Woodstock, CT 06281

  31 Rawson Rd, Woodstock, CT 06281
• 

  

  /36

  $638,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,880 Sq Ft

  18 Jeans Ct, Woodstock, CT 06281

  Fox Run Estates is a cul-de-sac neighborhood established in 2005. There are restrictive covenants, but no HOA fee. Jeans Court is a town maintained road. This Colonial, The Elmwood, is 2880sqft of living space. The main level has hardwood flooring throughout (except the bathroom). Open kitchen has an island that will seat 4, granite counters, and sliders to the newly expanded deck. The kitchen

  Lynn Converse RE/MAX Bell Park Realty

  18 Jeans Ct, Woodstock, CT 06281
• 

  $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
• 

  Est $1,024,993 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,590 Sq Ft

  39 Town Farm Rd, Woodstock, CT 06281

  39 Town Farm Rd, Woodstock, CT 06281
• 

  

  /7

  $699,999 Pending

  • 4 Beds
  • 3 Baths
  • 3,168 Sq Ft

  1991 Connecticut 198, Woodstock, CT 06281

  Are you tired of high energy bills and a drafty home? Welcome to this rare opportunity to live in a modern farmhouse built with ICF (Insulated concrete forms). This simple, open-concept farmhouse is situated on 3.41 acres and features a fully finished walk-out basement with 9-foot ceilings. We've maximized your investment by offering the most conditioned space possible, whether for a large family

  Steven Koleno Beycome of Connecticut

  1991 Connecticut 198, Woodstock, CT 06281

Showing Results 1 - 40, Page 1 of 18