Woodstock, CT Homes

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  /31

  $999,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,480 Sq Ft

  19 Hiawatha Heights, Woodstock Valley, CT 06282

  Price Improvement!!! RARE PRIVATE LAKEFRONT GEM: PICTURE WINDOWS FRAME PANORAMIC VIEWS & A COVETED SECLUDED FLAT LOT! Welcome to your sanctuary on Lake Bunggee in Woodstock, CT. This 3,480 sq ft fully renovated 4BR/3BA home offers unparalleled private living. Boasting 113 ft of direct, private lake frontage and a coveted flat lot for effortless water access. Expansive picture windows frame

  

  Kimberly Amundarain

  Executive Real Estate Inc.

  (860) 370-3421

  19 Hiawatha Heights, Woodstock Valley, CT 06282
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  /20

  $1,800 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,328 Sq Ft
  • House for Rent

  100 Bradford Corner Rd, Woodstock Valley, CT 06282

  No Pets. Quaint 1800s Antique Home for Rent. Step back in time with this charming 2-bedroom, 1-bath antique home that blends character and comfort. A mini-split system on the main level provides efficient heating and cooling, and a mini-split system will also be installed on the upper level, which includes the two bedrooms. If you appreciate the warmth and charm of a true New England antique,

  

  Carol Ryniewicz

  CR Premier Properties

  (860) 718-4492

  100 Bradford Corner Rd, Woodstock Valley, CT 06282
• 

  $700,000 Sold Nov 19, 2025

  • 2,960 Sq Ft
  • $236/SF
  • 2 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1811

  170 Lyon Hill Rd, Woodstock, CT 06281

  This original 1811 Colonial, surrounded by nature's beauty, will welcome and captivate in all seasons. The perennial gardens, charming stone walls, and mature trees create a visual masterpiece. Inside will surprise and delight with masterfully renovated living space throughout. The spectacular open kitchen with quartz countertops, pantry, newer appliances, and skylights sets the stage for

  Mary Ellen Barnett William Pitt Sotheby's Int'l

  170 Lyon Hill Rd, Woodstock, CT 06281
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  /42

  Not Listed For Sale

  XO Pole Bridge Rd, Woodstock, CT 06281

  XO Pole Bridge Rd, Woodstock, CT 06281
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  /40

  $529,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,887 Sq Ft

  71 Rawson Rd, Woodstock, CT 06281

  Discover a timeless blend of history and modern comfort at 71 Rawson Road, a lovingly modernized 1800s Colonial-style farmhouse located off a serene country road in Woodstock, CT. This distinguished "gentleman's farm" encompasses 1,887 sq ft of living space with 4 well-appointed bedrooms and 2 1/2 baths-perfectly poised for today's lifestyle while retaining classical New England charm. Step

  

  James Duffer

  RISE REC

  (860) 787-8530

  71 Rawson Rd, Woodstock, CT 06281
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  /15

  $2,000 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • House for Rent

  66 Indian Spring Rd, Woodstock, CT 06281

  Single family home for rent on Woodstock Valley's Witches Woods Lake. This ranch style home offers two bedrooms and two full baths. There is a partially finished basement with its own access, living space, and two additional beds. Washer and dryer included in this rental. Enjoy life on the lake and all its beauty. This property comes fully furnished with enclosed porch, full deck, and outside

  Casey Hardell CR Premier Properties

  66 Indian Spring Rd, Woodstock, CT 06281
• 

  $150,000 Sold Nov 18, 2025

  • 888 Sq Ft
  • $169/SF
  • 23 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1951

  9 Sherman Rd, Woodstock, CT 06281

  Investor Opportunity in Woodstock! Set on a corner lot on a quiet country road, this 2-bedroom ranch offers strong potential for renovation or redevelopment. The home features a classic layout with a spacious living room, fireplace, eat-in kitchen, and full bath. A detached red barn adds charm and versatility - ideal for workshop, horse paddock, storage, or possible conversion. The interior ready

  Ryan Braunagel Keller Williams Realty Prtnrs.

  9 Sherman Rd, Woodstock, CT 06281
• 

  Est $893,767 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
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  /38

  $450,000 Under Contract

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

  211 New Sweden Rd, Woodstock, CT 06281

  Sellers are motivated! Welcome home to this classic Colonial nestled on a 2-acre country lot in desirable Woodstock! Built in 2004, this spacious 2,016 sq. ft. home offers 3 bedrooms, 2.5 baths, and a layout designed for comfortable everyday living. The main level features a bright living room, formal dining area, and a large kitchen ready for your personal touch. Upstairs, you'll find three

  

  Carol Ryniewicz

  CR Premier Properties

  (860) 590-6977

  211 New Sweden Rd, Woodstock, CT 06281
• 

  $435,000 Sold Nov 18, 2025

  • 1,210 Sq Ft
  • $360/SF
  • 9 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1997

  69 Lyon Hill Rd, Woodstock, CT 06281

  Nestled on a picturesque 1.75-acre lot in the heart of Woodstock, Connecticut, this lovingly maintained 3-bedroom, 2-bathroom Cape offers the perfect blend of country charm and modern convenience. The first-floor primary bedroom features an ensuite bath and laundry, providing ideal single-level living. Two additional bedrooms and a full bath upstairs offer ample space for family or guests. A

  Kerri Mullen CR Premier Properties

  69 Lyon Hill Rd, Woodstock, CT 06281
• 

  Est $477,230 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,950 Sq Ft

  51 Tayler Trail, Woodstock Valley, CT 06282

  51 Tayler Trail, Woodstock Valley, CT 06282
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  /5

  $290,000 Pending

  • 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

  (860) 407-5580

  10 Laurel Hill Dr, Woodstock Valley, CT 06282
• 

  $370,000 Sold Nov 17, 2025

  • 1,536 Sq Ft
  • $241/SF
  • 66 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1880

  328 County Rd, Woodstock, CT 06281

  Charming Farmhouse located on a picturesque 1.2 acre corner lot in Woodstock CT! This 3 bedroom, 2 bath home blends historic charm with modern comfort. Featuring hardwood floors throughout, a spacious living room with cozy fireplace, and a large dining room perfect for gatherings. The cozy kitchen opens to a low-maintenance Trex deck, which is ideal for relaxing or entertaining while enjoying

  Shiloh Therrien The Neighborhood Realty Group

  328 County Rd, Woodstock, CT 06281
• 

  Est $483,953 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
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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
• 

  $430,000 Sold Nov 14, 2025

  • 1,560 Sq Ft
  • $276/SF
  • 5 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1997

  15 Windswept Dr, Woodstock, CT 06281

  Welcome to this inviting 3-bedroom, 3-bathroom home nestled on a quiet cul-de-sac in Woodstock, CT. Bursting with curb appeal, this property blends comfort, character, and convenience. It's just 7 minutes to the Massachusetts border and 6 minutes to Bigelow Hollow State Park, offering the best of both privacy and easy access to nature and amenities. Inside, you'll find a welcoming layout with a

  Ashley Walker Brunet and Company Real Estate

  15 Windswept Dr, Woodstock, CT 06281
• 

  Est $663,515 Not Listed For Sale

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

  429 Child Rd, Woodstock, CT 06281

  429 Child Rd, Woodstock, CT 06281
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  /19

  $895,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,300 Sq Ft

  36 Olde Meadow Rd, Woodstock, CT 06281

  TO BE CONSTRUCTED: Welcome to Eastwood Estates - Luxury Living in the Heart of Woodstock! Discover the elegance and tranquility of Eastwood Estates. If you're looking for privacy, this 1.92 acre lot borders open space with lovely stone walls. Modern Farmhouse home design is stunning with timeless curb appeal. Some exterior features: white clapboard siding, gabled dormers, and a welcoming covered

  

  Tina Lajoie

  William Raveis Real Estate

  (860) 407-5265

  36 Olde Meadow Rd, Woodstock, CT 06281
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  $653,950 Sold Nov 12, 2025

  • 1,922 Sq Ft
  • $340/SF
  • 22 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1986

  115 Crooked Trail Extension, Woodstock, CT 06281

  This charming, year-round lake front home located at 115 Crooked Trail Ext in Woodstock, CT was built in 1986 and offers a cozy and inviting atmosphere. Located on the peaceful 70 acre Witches Wood lake in Connecticut's quiet corner offering water activities and lake life culture. With 3 bathrooms, 2 full baths and a total finished area of 1,922 sq. ft., this move in ready, fully furnished home

  Derek Greene Derek Greene

  115 Crooked Trail Extension, 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
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  /27

  $775,000

  • 2 Beds
  • 2 Baths
  • 1,575 Sq Ft

  60 Indian Spring Rd, Woodstock, CT 06281

  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 expansive views and direct frontage, the home has been thoughtfully updated in recent years with a

  Jennie Kesselman Berkshire Hathaway NE Prop.

  60 Indian Spring Rd, Woodstock, CT 06281
• 

  $415,000 Sold Nov 06, 2025

  • 1,602 Sq Ft
  • $259/SF
  • 2 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2001

  86 Lebanon Hill Rd, Woodstock, CT 06281

  Embrace the quintessential New England lifestyle in this charming 4-bedroom, 2-bathroom Cape nestled on over 4 private, wooded acres in Woodstock. Enter inside and be greeted by hardwood floors that flow throughout the home. The main level offers a bright, sunny living room that leads into the well-appointed kitchen, featuring stainless steel appliances, an electric range, and a dining area with

  Christopher Boule Lamacchia Realty

  86 Lebanon Hill Rd, Woodstock, CT 06281
• 

  Est $269,955 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
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  /37

  $560,000

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

  104 Pulpit Rock Rd, Woodstock, CT 06281

  Experience family living in this beautifully updated 4 bed & 2.5 bath Colonial, perfectly set in one of the area's most desirable and private locations! Peace of mind with a BRAND-NEW ROOF! Surrounded by a flat, expansive, and beautifully usable yard, this home offers a rare sense of serenity and estate-like presence. Hardwood floors flow throughout, complementing an updated kitchen and a warm,

  Skyla Gagnon RE/MAX Bell Park Realty

  104 Pulpit Rock Rd, Woodstock, CT 06281
• 

  $395,000 Sold Nov 03, 2025

  • 2,339 Sq Ft
  • $169/SF
  • 16 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1993

  50 Crooked Trail, Woodstock, CT 06281

  This is a large raised ranch with all 3 bedrooms on the main level. The primary bedroom has it's own full bath. The kitchen and living rooms are bright and open. The living room features a wood burning fireplace. There is a deck off the kitchen. The lower level is finished with a third full bathroom, study with access to a ground level deck, and a family room with a beautiful coal stove for added

  Lynn Converse RE/MAX Bell Park Realty

  50 Crooked Trail, Woodstock, CT 06281
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  Est $689,225 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
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  /39

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 2,952 Sq Ft

  26 Center Rd, Woodstock, CT 06281

  Tucked away on one of Woodstock's most desirable roads, this immaculate 2,952 sq. ft. home is set on 3.5 private acres at the end of a long driveway. The property includes six garage bays-ideal for those needing exceptional storage or vehicle capacity. Freshly painted and in like-new condition, it offers ideal first-floor living with a spacious primary suite and laundry on the main level. The

  John Downs Berkshire Hathaway NE Prop.

  26 Center Rd, Woodstock, CT 06281
• 

  $500,000 Sold Oct 31, 2025

  • 2,344 Sq Ft
  • $213/SF
  • 11 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2002

  31 Deer Meadow Ln, Woodstock, CT 06281

  Welcome to Deer Meadow - one of the area's most desirable cul-de-sac neighborhoods! This solid, classic Colonial sits in an open-space subdivision with a shared recreational area for everyone to enjoy. Inside, sunlight fills the inviting living room with hardwood floors and a cozy fireplace. The spacious eat-in kitchen features solid wood cabinetry, Corian counters, a center island, and sliders

  Mary Collins Berkshire Hathaway NE Prop.

  31 Deer Meadow Ln, Woodstock, CT 06281
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  Est $683,706 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,277 Sq Ft

  739 Route 171, Woodstock, CT 06281

  739 Route 171, Woodstock, CT 06281
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  /40

  $774,900

  • 4 Beds
  • 2.5 Baths
  • 3,662 Sq Ft

  189 Center Rd, Woodstock, CT 06281

  A beautifully maintained colonial nestled in one of Woodstock's most picturesque settings with many recent updates. Offering the perfect blend of traditional New England charm and modern comfort, featuring 4 bedrooms, 2.5-baths and spanning nearly 3,000 square feet. (Additional 664 sq ft in basement) Upon arrival you are greeted with a front farmers porch, step inside to discover 9' ceilings

  Mark Tetreault, II RE/MAX Bell Park Realty

  189 Center Rd, Woodstock, CT 06281
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  $325,000 Sold Oct 31, 2025

  • 852 Sq Ft
  • $381/SF
  • 8 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1960

  78 Laurel Hill Dr, Woodstock Valley, CT 06282

  OFFERS BEING REVIEWED Idyllic Lakeside Living on Lake Bungee! Escape to this charming and fully updated 1-bedroom, 1-bathroom cottage nestled in the highly desirable Lake Bungee community of Woodstock, CT. Perfect as a year-round retreat or a weekend getaway, this property offers the best of lakeside living with modern comforts. The cottage features a bright, refreshed interior with updates

  Georgi Morin S.C.E. Real Estate

  78 Laurel Hill Dr, Woodstock Valley, CT 06282
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  /39

  Est $465,392 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,644 Sq Ft

  1115 Route 169, Woodstock, CT 06281

  1115 Route 169, Woodstock, CT 06281
• 

  

  /40

  $689,000

  • 4 Beds
  • 2 Baths
  • 2,630 Sq Ft

  29 Crooked Trail Extension, Woodstock, CT 06281

  Experience the beauty of lakefront living on one of Woodstock's most sought-after destinations-Witches Woods Lake. This rare offering boasts over 200 feet of direct waterfront with a private dock and captivating views. Built in 1982 and offering more than 2,500 sq. ft. of living space, this 4-bedroom, 2-bath home is designed for both comfort and connection. The bright, open-concept main level

  Lauren Heidelberger Berkshire Hathaway NE Prop.

  29 Crooked Trail Extension, Woodstock, CT 06281
• 

  $425,000 Sold Oct 30, 2025

  • 1,412 Sq Ft
  • $301/SF
  • 136 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1988

  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

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

  Est $749,758 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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  /39

  $549,000

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

  101 Child Hill Rd, Woodstock, CT 06281

  Step back in time with this one-of-a-kind 1830 Greek Revival farmhouse, offering 2,150 sq ft of character and charm on a picturesque 0.90-acre lot surrounded by farm land. Just down the hill from historic Woodstock Hill and the Academy, this setting is as scenic as it is convenient. Inside, wide plank floors and distinctive windows frame beautiful country views, while the front entry showcases

  Kristen Kaskela Berkshire Hathaway NE Prop.

  101 Child Hill Rd, Woodstock, CT 06281
• 

  $240,000 Sold Oct 29, 2025

  • 1,390 Sq Ft
  • $173/SF
  • 30 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  1200 Route 171, Woodstock, CT 06281

  Charming circa 1900 home set on 9.05 acres, including the main 3-acre homesite and two additional separate 3-acre lots. Surrounded by woodlands, gardens, and mature landscaping with lilacs, wisteria, dawn redwoods, fruit trees, and perennial beds, the property offers natural beauty and privacy. The eat in kitchen with pantry opens to the dining and family room, with a slider leading to a 12' x

  Kris Robinson Eagle Eye Realty PLLC

  1200 Route 171, Woodstock, CT 06281
• 

  Est $666,406 Not Listed For Sale

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

  1530 Route 169, Woodstock, CT 06281

  1530 Route 169, Woodstock, CT 06281
• 

  

  /40

  $659,900

  • 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
• 

  $130,000 Sold Oct 28, 2025

  • Land
  • 3.96 Acres
  • $32,828 per Acre

  • 22 Days On Market

  0 Connecticut 169, Woodstock, CT 06281

  This parcel features over 700 feet of road frontage on Route 169. Slopes from road and flattens as you approach Bentley Sport Complex to the rear. Will need to perc test. Woodstock Hill location across from The Inn at Woodstock Hill. Nice view.

  Richard Loomis RE/MAX Bell Park Realty

  0 Connecticut 169, Woodstock, CT 06281

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