Woodstock, CT Homes

• 

  $395,000

  Sold Nov 03, 2025

  50 Crooked Trail, Woodstock, CT 06281

  • 3 Beds
  • 3 Baths
  • 2,339 Sq Ft
  • Built 1993

  Last Sold Summary

  • 6% Below List Price
  • $169/SF
  • 16 Days On Market

  Current Estimated Value $424,186

  Last Listing Agent Lynn Converse RE/MAX Bell Park Realty

  50 Crooked Trail, Woodstock, CT 06281
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• 

  Est $671,017

  Not Listed For Sale

  1530 Route 169, Woodstock, CT 06281

  • 4 Beds
  • 2.5 Baths
  • 2,960 Sq Ft
  • Built 2005

  1530 Route 169, Woodstock, CT 06281

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Kristen Kaskela Berkshire Hathaway NE Prop.
• 

  

  

  /5

  $99,000

  • Land
  • 3.5 Acres
  • $28,286 per Acre

  Lot 03-2 New Sweden Rd, Woodstock, CT 06281

  This site is well off the road, and ready to go. The driveway is owned, and the neighbor has a right of way over it. Once past the neighbors property, rise up to the building site. The site is level and open, and the lot then slopes down to the south and west. This portion of the land is wooded. Conduit for power is in place. Agent related to seller.

  Lynn Converse RE/MAX Bell Park Realty

  Lot 03-2 New Sweden Rd, Woodstock, CT 06281
• 

  $26,000

  Sold Oct 08, 2025

  25 Route 197 Unit Lot 40, Woodstock, CT 06281

  • 1 Bed
  • 1 Bath
  • 300 Sq Ft
  • Built 1995

  Last Sold Summary

  • 42% Below List Price
  • $87/SF
  • 168 Days On Market

  Last Listing Agent Keri Roy Kazantzis Real Estate, LLC

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

  Est $581,506

  Not Listed For Sale

  593 Brickyard Rd, Woodstock, CT 06281

  • 3 Beds
  • 2.5 Baths
  • 2,740 Sq Ft
  • Built 2003

  593 Brickyard Rd, Woodstock, CT 06281

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Brooke Gelhaus Compass Connecticut, LLC
• 

  

  /19

  $329,000

  $21K PRICE DROP Under Contract

  • 2 Beds
  • 1.5 Baths
  • 1,894 Sq Ft

  133 Route 198, Woodstock Valley, CT 06282

  This sprawling country style ranch home has plenty of space! Over 1800 sq.ft of living space all on one level. Street card states 2 bedrooms but the house is arranged and used as a 3-4 bedroom. Cozy eat in kitchen with built in dining area. Formal living room has a stone fireplace and hardwood flooring. Formal dining room. Family room is huge but currently used as the seller's primary bedroom,

  Robin Smith RE/MAX Bell Park Realty

  133 Route 198, Woodstock Valley, CT 06282
• 

  $700,000

  Sold Nov 19, 2025

  170 Lyon Hill Rd, Woodstock, CT 06281

  • 3 Beds
  • 2.5 Baths
  • 2,960 Sq Ft
  • Built 1811

  Last Sold Summary

  • 3% Above List Price
  • $236/SF
  • 2 Days On Market

  Current Estimated Value $705,516

  Last Listing Agent Mary Ellen Barnett William Pitt Sotheby's Int'l

  170 Lyon Hill Rd, Woodstock, CT 06281
• 

  Est $446,284

  Not Listed For Sale

  538 Center Rd, Woodstock, CT 06281

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1974

  538 Center Rd, Woodstock, CT 06281

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Brooke Coughlin Lamacchia Realty
• 

  

  /9

  $45,000

  • 1 Bed
  • 1 Bath
  • 510 Sq Ft

  25 Route 197 Unit 29, Woodstock, CT 06281

  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

  Margaret Young CR Premier Properties

  25 Route 197 Unit 29, Woodstock, CT 06281
• 

  $559,000

  Sold Feb 02, 2026

  23 Little Bungee Hill Rd, Woodstock Valley, CT 06282

  • 4 Beds
  • 2 Baths
  • 2,160 Sq Ft
  • Built 1960

  Last Sold Summary

  • 11% Below List Price
  • $259/SF
  • 198 Days On Market

  Current Estimated Value $564,522

  Last Listing Agent Alan Berman Signature Properties of N.E.

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

  Est $746,637

  Not Listed For Sale

  50 Lake View Dr, Woodstock, CT 06281

  • 2 Beds
  • 2 Baths
  • 2,124 Sq Ft
  • Built 1998

  50 Lake View Dr, Woodstock, CT 06281

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Carol Ryniewicz CR Premier Properties
• 

  

  /25

  $489,900

  Open Sat 1PM - 3PM $10K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 2,014 Sq Ft

  21 Fairfield Dr, Woodstock, CT 06281

  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

  Patricia Scarpa Marino Realty LLC

  21 Fairfield Dr, Woodstock, CT 06281
• 

  $204,000

  Sold Aug 15, 2025

  000 Green Rd, Woodstock, CT 06281

  • Land
  • 19 Acres
  • $10,737 per Acre

  Last Sold Summary

  • 5% Below List Price
  • 350 Days On Market

  Last Listing Agent Dennis Duga Northeast Realty

  000 Green Rd, Woodstock, CT 06281
• 

  Est $520,614

  Not Listed For Sale

  1157 Route 169, Woodstock, CT 06281

  • 3 Beds
  • 2.5 Baths
  • 1,924 Sq Ft
  • Built 2001

  1157 Route 169, Woodstock, CT 06281

  Last Sold Summary

  • 49 Days On Market

  Last Listing Agent Patrick Sweeney RE/MAX Professional Associates
• 

  

  /27

  $450,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  83 Dodge Rd, Woodstock, CT 06281

  Set in the charming town of Woodstock and minutes from the Massachusetts line, this 3-bedroom, 2.5-bath home offers space, flexibility, and a layout ideal for both everyday living .The home includes two primary suites- rare find! Inside, you'll find a spacious living room with vaulted ceilings and a propane fireplace, creating a warm and inviting focal point. The large kitchen features abundant

  Skyla Gagnon RE/MAX Bell Park Realty

  83 Dodge Rd, Woodstock, CT 06281
• 

  $327,000

  Sold Jun 09, 2026

  170 Smith Rd, Woodstock, CT 06281

  • 3 Beds
  • 2 Baths
  • 1,754 Sq Ft
  • Built 1973

  Last Sold Summary

  • 7% Below List Price
  • $186/SF
  • 8 Days On Market

  Last Listing Agent John Downs Berkshire Hathaway NE Prop.

  170 Smith Rd, Woodstock, CT 06281
• 

  Est $392,487

  Not Listed For Sale

  610 Route 197, Woodstock, CT 06281

  • 3 Beds
  • 1.5 Baths
  • 1,368 Sq Ft
  • Built 1953

  610 Route 197, Woodstock, CT 06281

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Sheena Ruggirello Real Broker CT, LLC
• 

  

  /40

  $1,450,000

  • 4 Beds
  • 5.5 Baths
  • 6,394 Sq Ft

  1374 Route 171, Woodstock Valley, CT 06282

  Set on 10.3 private acres in desirable Woodstock Valley, "Blue Heron Glade" offers a rare blend of privacy, natural beauty, and thoughtfully designed living spaces in Connecticut's Quiet Corner. A long private driveway with a charming cobblestone bridge leads to this exceptional property surrounded by stone walls, abundant wildlife, and a large pond frequented by blue herons. The main residence

  Kristen Kaskela Berkshire Hathaway NE Prop.

  1374 Route 171, Woodstock Valley, CT 06282
• 

  $385,000

  Sold Feb 26, 2026

  56 Laurel Hill Dr, Woodstock Valley, CT 06282

  • 3 Beds
  • 1.5 Baths
  • 1,008 Sq Ft
  • Built 1981

  Last Sold Summary

  • 45% Below List Price
  • $382/SF
  • 268 Days On Market

  Current Estimated Value $383,362

  Last Listing Agent Vivian Kozey CR Premier Properties

  56 Laurel Hill Dr, Woodstock Valley, CT 06282
• 

  Est $167,014

  Not Listed For Sale

  6 Old Sawmill Rd, Woodstock, CT 06281

  • 2 Beds
  • 0.5 Baths
  • 728 Sq Ft
  • Built 1960

  6 Old Sawmill Rd, Woodstock, CT 06281

  Last Sold Summary

  • 90 Days On Market

  Last Listing Agent Debra Burns Berkshire Hathaway NE Prop.
• 

  

  /39

  $520,000

  $29K PRICE DROP

  • 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
• 

  $415,000

  Sold Feb 24, 2026

  33 Playground Dr, Woodstock, CT 06281

  • 2 Beds
  • 2 Baths
  • 1,544 Sq Ft
  • Built 2005

  Last Sold Summary

  • 9% Above List Price
  • $269/SF
  • 6 Days On Market

  Current Estimated Value $415,092

  Last Listing Agent Joshua Somers P&H Property Consulting, Inc.

  33 Playground Dr, Woodstock, CT 06281
• 

  Est $414,399

  Not Listed For Sale

  32 Beech St, Woodstock, CT 06281

  • 3 Beds
  • 2 Baths
  • 1,526 Sq Ft
  • Built 1960

  32 Beech St, Woodstock, CT 06281

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Lynn Converse RE/MAX Bell Park Realty
• 

  /2

  $179,000

  • Land
  • 2.85 Acres
  • $62,807 per Acre

  0 Child Dome Rd Unit 24183816, Woodstock, CT 06281

  Rare opportunity to own a large buildable lot in Woodstock, CT. this serene rear lot is located on one of the highest points in Woodstock. Surrounded by Conservatory farmland, the views are for miles. The ride to this property, through sparsely populated countryside, will definitely give you feel of the natural surroundings. Although located "far from the crowd" you are centrally located to

  Bob Seele Coldwell Banker Realty

  0 Child Dome Rd Unit 24183816, Woodstock, CT 06281
• 

  $510,000

  Sold Dec 19, 2025

  71 Rawson Rd, Woodstock, CT 06281

  • 4 Beds
  • 2.5 Baths
  • 1,887 Sq Ft
  • Built 1800

  Last Sold Summary

  • 7% Below List Price
  • $270/SF
  • 81 Days On Market

  Current Estimated Value $527,168

  Last Listing Agent James Duffer RISE REC

  71 Rawson Rd, Woodstock, CT 06281
• 

  Est $509,000

  Not Listed For Sale

  35 Valley View Rd, Woodstock Valley, CT 06282

  • 3 Beds
  • 2.5 Baths
  • 2,184 Sq Ft
  • Built 1965

  35 Valley View Rd, Woodstock Valley, CT 06282

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Kristen Kaskela Berkshire Hathaway NE Prop.
• 

  

  /40

  $375,000

  Pending

  • 4 Beds
  • 1 Bath
  • 3,070 Sq Ft

  1210 Route 169, Woodstock, CT 06281

  Better than ever is what could be said about this pristine 1760 antique colonial home! With Muddy Brook winding through the property and conserved land located next door, what you see is what you get here: peace and serenity on 2.54 acres in desirable Woodstock, CT! With a new cedar roof, a rebuilt and sealed chimney and all new sills put in place years ago this classic will continue sitting

  Stephanie Gosselin Berkshire Hathaway NE Prop.

  1210 Route 169, Woodstock, CT 06281
• 

  $130,000

  Sold Oct 28, 2025

  0 Connecticut 169, Woodstock, CT 06281

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

  Last Sold Summary

  • 13% Below List Price
  • 22 Days On Market

  Last Listing Agent Richard Loomis RE/MAX Bell Park Realty

  0 Connecticut 169, Woodstock, CT 06281
• 

  Est $396,251

  Not Listed For Sale

  70 Red Cedar Rd, Woodstock Valley, CT 06282

  • 3 Beds
  • 2 Baths
  • 1,685 Sq Ft
  • Built 1992

  70 Red Cedar Rd, Woodstock Valley, CT 06282

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Diane White Berkshire Hathaway NE Prop.
• 

  

  /15

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft

  40 Crooked Trail, Woodstock, CT 06281

  This 3-bedroom Cape Cod has a ton of potential! Located in a peaceful lake neighborhood, and within walking distance of a beach, this property offers plenty of opportunity to get outside and enjoy the outdoors. If you need a break from the water, enjoy the large private back deck that's perfect for relaxing, hosting, and more. The plumbing system did not hold pressure at time of winterization,

  Ryan King Aspen Realty Group

  40 Crooked Trail, Woodstock, CT 06281
• 

  $715,000

  Sold Oct 21, 2025

  64 May Brook, Woodstock, CT 06281

  • 4 Beds
  • 5 Baths
  • 3,795 Sq Ft
  • Built 2003

  Last Sold Summary

  • 1% Below List Price
  • $188/SF
  • 35 Days On Market

  Current Estimated Value $759,631

  Last Listing Agent Jared Meehan RE/MAX Bell Park Realty

  64 May Brook, Woodstock, CT 06281
• 

  Est $438,900

  Not Listed For Sale

  209 Crystal Pond Rd, Woodstock Valley, CT 06282

  • 3 Beds
  • 3 Baths
  • 2,492 Sq Ft
  • Built 2001

  209 Crystal Pond Rd, Woodstock Valley, CT 06282

  Last Sold Summary

  • 61 Days On Market

  Last Listing Agent Jennifer Pagan RE/MAX One
• 

  

  /38

  $699,000

  $76K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,855 Sq Ft

  60 Indian Spring Rd, Woodstock, CT 06281

  Perched above the shoreline of private Witches Woods Lake, this fully furnished waterfront retreat offers breathtaking water views, exceptional privacy, and a rare sense of tranquility. Brand-new multi-level TimberTech decks spanning roughly 800 square feet create an expansive outdoor living experience, perfectly positioned for entertaining, relaxing, or simply taking in the beauty of the lake

  Jennie Kesselman Berkshire Hathaway NE Prop.

  60 Indian Spring Rd, Woodstock, CT 06281
• 

  $1,000,000

  Sold Jun 10, 2026

  33 Meehan Rd, Woodstock, CT 06281

  • 3 Beds
  • 4 Baths
  • 4,190 Sq Ft
  • Built 1993

  Last Sold Summary

  • $239/SF
  • 9 Days On Market

  Last Listing Agent John Downs Berkshire Hathaway NE Prop.

  33 Meehan Rd, Woodstock, CT 06281
• 

  Not Listed For Sale

  30 Windswept Dr, Woodstock, CT 06281

  • 3 Beds
  • 2 Baths
  • 2,516 Sq Ft
  • Built 1998

  30 Windswept Dr, Woodstock, CT 06281

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Anna Sava Namnoum William Raveis Real Estate
• 

  

  /40

  $599,000

  $51K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 2,393 Sq Ft

  511 Perrin Rd, Woodstock, CT 06281

  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

  John Downs Berkshire Hathaway NE Prop.

  511 Perrin Rd, Woodstock, CT 06281
• 

  $500,000

  Sold Oct 31, 2025

  31 Deer Meadow Ln, Woodstock, CT 06281

  • 3 Beds
  • 2.5 Baths
  • 2,344 Sq Ft
  • Built 2002

  Last Sold Summary

  • 5% Below List Price
  • $213/SF
  • 11 Days On Market

  Current Estimated Value $530,661

  Last Listing Agent Mary Collins Berkshire Hathaway NE Prop.

  31 Deer Meadow Ln, Woodstock, CT 06281
• 

  Est $718,511

  Not Listed For Sale

  133 Calkins Rd, Woodstock, CT 06281

  • 3 Beds
  • 3 Baths
  • 2,722 Sq Ft
  • Built 2003

  133 Calkins Rd, Woodstock, CT 06281

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Jennifer Jackson Berkshire Hathaway NE Prop.
• 

  

  /19

  $74,900

  Open Sun 11AM - 12PM

  • 2 Beds
  • 1 Bath
  • 450 Sq Ft

  25 Route 197 Unit 70, Woodstock, CT 06281

  Motivated seller.. Book your tour today easy to show.. 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

  KAREN MILHEM Media Realty Group Inc.

  25 Route 197 Unit 70, Woodstock, CT 06281
• 

  $1,450,000

  Sold Aug 26, 2025

  6 & 8 Stone Bridge Rd, Woodstock, CT 06281

  • 6 Beds
  • 6 Baths
  • 4,517 Sq Ft
  • Built 1769

  Last Sold Summary

  • 9% Below List Price
  • $321/SF
  • 133 Days On Market

  Last Listing Agent John Downs Berkshire Hathaway NE Prop.

  6 & 8 Stone Bridge Rd, Woodstock, CT 06281

Showing Results 41 - 80, Page 2 of 18