Windham, CT Homes

• 

  

  

  /40

  $899,000 Pending

  • 3 Beds
  • 5 Baths
  • 3,600 Sq Ft

  72 Indian Spring Rd, Woodstock, CT 06281

  Motivated Sellers! Check out this four-story custom-built home blends timeless craftsmanship with luxurious modern touches. Designed to showcase breathtaking lake views and sunsets, this home features exposed beams, cathedral ceilings, and oversized windows throughout. Highlights include mahogany front stairs and porches, a stucco and stone exterior, and an on-demand heated driveway. Inside,

  

  Carol Ryniewicz

  CR Premier Properties

  (860) 264-0216

  72 Indian Spring Rd, Woodstock, CT 06281
• 

  $430,000 Sold Jul 28, 2025

  • 1,919 Sq Ft
  • $224/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1830

  324 Connecticut 169, Woodstock, CT 06281

  Charming Antique Cape in Desirable South Woodstock Step into timeless charm with this beautifully updated 1,919 sq ft antique Cape nestled in the heart of sought-after South Woodstock. This 3-bedroom - 1 on the first floor, 2 full bath home offers a perfect blend of historic character and modern convenience. Inside, you'll find two cozy fireplaces with wood stove inserts, a thoughtfully remodeled

  Diane White CR Premier Properties

  324 Connecticut 169, Woodstock, CT 06281
• 

  Est $859,131 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,614 Sq Ft

  145 Laurel Hill Dr, Woodstock Valley, CT 06282

  145 Laurel Hill Dr, Woodstock Valley, CT 06282
• 

  

  

  /39

  $450,000 Under Contract

  • 4 Beds
  • 1.5 Baths
  • 1,412 Sq Ft

  47 Little Bungee Hill Rd, Woodstock Valley, CT 06282

  Welcome home to this charming 1,412 sq ft ranch just a stone's throw from sparkling Lake Bunggee! Inside, an airy open floor plan unites a sun-splashed living room with a stylish kitchen and dining area-granite counters, generous cabinetry, and sight-lines that make entertaining a breeze. Three comfortable bedrooms plus a flexible fourth (ideal for an office, playroom, or guest room) share 1 1/2

  

  Carol Ryniewicz

  CR Premier Properties

  (860) 980-4978

  47 Little Bungee Hill Rd, Woodstock Valley, CT 06282
• 

  $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
• 

  Est $485,249 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,834 Sq Ft

  41 Crooked Trail, Wood Stock, CT 06281

  41 Crooked Trail, Wood Stock, CT 06281
• 

  

  /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
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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
• 

  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
• 

  $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 $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
• 

  $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 $299,500 Not Listed For Sale

  • 2 Beds
  • 0.5 Baths
  • 480 Sq Ft

  208 Baxter Rd, Woodstock, CT 06281

  208 Baxter Rd, Woodstock, CT 06281
• 

  

  /39

  $625,000 Pending

  • 6 Beds
  • 5 Baths
  • 4,138 Sq Ft

  45 Roseland Park Rd, Woodstock, CT 06281

  Waterfront & Waterfall views!! This unique and one-of-a-kind 1.65-acre estate features an incredible 4-bdrm and 4 full bath main house with a 2-bdrm and 1 full bath guest house!! The main house is a beautifully restored antique property offering a rare blend of historic charm, modern comforts, and unique features like built-in brick oven, slate floors, two multi-person jacuzzi tubs and more!!!

  

  Tina Lajoie

  William Raveis Real Estate

  (860) 590-4268

  45 Roseland Park Rd, Woodstock, CT 06281
• 

  $456,000 Sold Jul 24, 2025

  • 1,789 Sq Ft
  • $255/SF
  • 8 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1987

  52 Crooked Trail, Woodstock, CT 06281

  Contemporary Charm Across from Witches Woods Lake! Step into this inviting 3-bedroom, 2.5-bath contemporary home offering a bright open floor plan, soaring vaulted ceilings, and gleaming hardwood floors throughout. Fireplaced living room, applianced kitchen and breakfast bar area, first floor laundry and large deck. Very private lot across from the Witched Woods lake!!. Central air keeps the home

  Cary Marcoux RE/MAX Bell Park Realty

  52 Crooked Trail, Woodstock, CT 06281
• 

  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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  /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
• 

  $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
• 

  Est $290,603 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft

  170 Laurel Hill Dr, Woodstock Valley, CT 06282

  170 Laurel Hill Dr, Woodstock Valley, CT 06282
• 

  

  /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
• 

  $420,000 Sold Jul 18, 2025

  • 1,612 Sq Ft
  • $261/SF
  • 80 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  28 Crooked Trail, Woodstock, CT 06281

  Welcome to 28 Crooked Trail! Nestled in a tranquil setting near Witches Woods Lake, this beautifully updated contemporary cape is sure to check all your boxes. Step inside & admire a remodeled eat-in kitchen (2022) w/ subway tiles, butcher block countertops and ample cabinet space, opening into a bright and inviting living area perfect for entertaining or unwinding after a day on the water.

  Rich Jenkins Real Broker CT, LLC

  28 Crooked Trail, Woodstock, CT 06281
• 

  Est $653,623 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 3,526 Sq Ft

  3 Holmeslea Ct, Woodstock, CT 06281

  3 Holmeslea Ct, Woodstock, CT 06281
• 

  

  /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
• 

  $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 $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
• 

  

  /37

  $579,900

  • 3 Beds
  • 1 Bath
  • 1,323 Sq Ft

  1 Laurel Hill Dr, Woodstock Valley, CT 06282

  Pride of ownership shines in this wonderful year-round ranch nestled in a peaceful cove on fully recreational Lake Bungee!Whether you're looking to fish,swim,kayak,ski,or ice fish this home offers four seasons of fun right from your backyard-complete with your own private dock and stunning view of the nearby waterfall! Thoughtfully updated in 2025 the entire house was given a fresh new look!

  Pat Malek First Choice Realty

  1 Laurel Hill Dr, Woodstock Valley, CT 06282
• 

  

  /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
• 

  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
• 

  

  /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
• 

  $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 $561,564 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
• 

  

  /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
• 

  $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 $633,542 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

  $595,000

  • 4 Beds
  • 2 Baths
  • 2,160 Sq Ft

  23 Little Bungee Hill Rd, Woodstock Valley, CT 06282

  The pictures really tell the story with this one. Down a quiet road on a 1.22 acre lot within sight of Lake Bunggee, this 2160 sq ft, 4 Br, 2 Ba home has been rebuilt from the floor joists up. Rich with custom touches and all new electrical, plumbing, insulation, roofing, etc. Pull up the double wide driveway (paved in 2023) to a two car garage (575 sq ft, plus loft), where you'll never get

  Alan Berman Signature Properties of NewEng

  23 Little Bungee Hill Rd, Woodstock Valley, CT 06282
• 

  $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 $480,937 Not Listed For Sale

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

  538 Center Rd, Woodstock, CT 06281

  538 Center Rd, Woodstock, CT 06281
• 

  

  /40

  $659,999

  • 3 Beds
  • 3.5 Baths
  • 3,078 Sq Ft

  39 Grey Fox Landing, Woodstock, CT 06281

  This meticulously cared-for Colonial is nestled in a desirable neighborhood and offers the perfect blend of comfort and versatility. The spacious room above the garage has been beautifully finished, making it ideal for an in-law suite, guest space, or bonus room. The kitchen features granite countertops, stainless steel appliances(all approximately 5 years old), and flows seamlessly into the main

  Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

  39 Grey Fox Landing, Woodstock, CT 06281

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