Woodstock, CT Homes

• 

  

  

  /27

  $450,000

  • 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
• 

  $420,000

  Sold Jul 18, 2025

  28 Crooked Trail, Woodstock, CT 06281

  • 3 Beds
  • 2 Baths
  • 1,612 Sq Ft
  • Built 1984

  Last Sold Summary

  • 5% Below List Price
  • $261/SF
  • 80 Days On Market

  Current Estimated Value $440,336

  Last Listing Agent Rich Jenkins Real Broker CT, LLC

  28 Crooked Trail, Woodstock, CT 06281
• 

  Est $404,248

  Not Listed For Sale

  33 Oak Dr, Woodstock Valley, CT 06282

  • 3 Beds
  • 2.5 Baths
  • 1,943 Sq Ft
  • Built 1986

  33 Oak Dr, Woodstock Valley, CT 06282

  Last Sold Summary

  • 5 Days On Market
• 

  

  

  /40

  $1,450,000

  • 3 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
• 

  $460,000

  Sold Dec 11, 2025

  33 Bassett Hill Rd, Woodstock, CT 06281

  • 3 Beds
  • 1.5 Baths
  • 2,258 Sq Ft
  • Built 1941

  Last Sold Summary

  • 10% Above List Price
  • $204/SF
  • 14 Days On Market

  Current Estimated Value $454,774

  Last Listing Agent Jonathan Bolano eXp Realty

  33 Bassett Hill Rd, Woodstock, CT 06281
• 

  Est $740,492

  Not Listed For Sale

  249 Barlow Cemetery Rd, Woodstock, CT 06281

  • 4 Beds
  • 2.5 Baths
  • 2,922 Sq Ft
  • Built 2005

  249 Barlow Cemetery Rd, Woodstock, CT 06281

  Last Sold Summary

  • 30 Days On Market
• 

  

  /15

  $200,000

  Pending

  • 2 Beds
  • 1 Bath
  • 1,024 Sq Ft

  259 Old Hall Rd, Woodstock, CT 06281

  Pretty lot in South Woodstock, that abuts the Mill Brook on the west, and has a pretty view over fields to the east. The property has been as cleaned up as it will be, and is being sold as-is. The last occupancy was 3 years ago, however the house and property have been cared for by the current owners. The previous owner was there for decades. There has been no heat or hot water turned on since

  Lynn Converse RE/MAX Bell Park Realty

  259 Old Hall Rd, Woodstock, CT 06281
• 

  $490,000

  Sold Oct 03, 2025

  25 Barlow Cemetery Rd, Woodstock Valley, CT 06282

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • Built 1996

  Last Sold Summary

  • 1% Above List Price
  • $284/SF
  • 4 Days On Market

  Current Estimated Value $483,537

  Last Listing Agent Carol Ryniewicz CR Premier Properties

  25 Barlow Cemetery Rd, Woodstock Valley, CT 06282
• 

  Est $848,339

  Not Listed For Sale

  20 Herindeen Landing, Woodstock, CT 06281

  • 4 Beds
  • 2.5 Baths
  • 3,217 Sq Ft
  • Built 2004

  20 Herindeen Landing, Woodstock, CT 06281

  Last Sold Summary

  • 1 Day On Market
• 

  

  /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
• 

  $75,000

  Sold Oct 06, 2025

  0 Rt 198, Woodstock, CT 06281

  • Land
  • 9.64 Acres
  • $7,780 per Acre

  Last Sold Summary

  • 24% Below List Price
  • 198 Days On Market

  Last Listing Agent Nicole Gleason CR Premier Properties

  0 Rt 198, Woodstock, CT 06281
• 

  Est $397,148

  Not Listed For Sale

  11 Red Cedar Rd, Woodstock Valley, CT 06282

  • 3 Beds
  • 1.5 Baths
  • 1,955 Sq Ft
  • Built 1978

  11 Red Cedar Rd, Woodstock Valley, CT 06282

  Last Sold Summary

  • 2 Days On Market
• 

  /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
• 

  $268,000

  Sold Dec 10, 2025

  17 Woodstock Meadows, Woodstock, CT 06281

  • 1 Bed
  • 1 Bath
  • 768 Sq Ft
  • Built 1985

  Last Sold Summary

  • 3% Above List Price
  • $349/SF
  • 36 Days On Market

  Current Estimated Value $260,136

  Last Listing Agent Tracie Gagnon Berkshire Hathaway NE Prop.

  17 Woodstock Meadows, Woodstock, CT 06281
• 

  Est $392,918

  Not Listed For Sale

  80 Barlow Cemetery Rd, Woodstock Valley, CT 06282

  • 2 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 1979

  80 Barlow Cemetery Rd, Woodstock Valley, CT 06282

  Last Sold Summary

  • 5 Days On Market
• 

  

  /33

  $665,000

  Under Contract

  • 3 Beds
  • 3 Baths
  • 2,250 Sq Ft

  239 Barlow Cemetery Rd, Woodstock, CT 06281

  Enjoy this beautiful, like-new, well-cared for 2250 square foot 3 bedroom, 3 full bath home in picturesque Woodstock setting. Private but yet convenient to major routes. Home features hardwood floors on main level with an open floor plan. Eat in Kitchen has stainless steel appliances, granite countertops, tile backsplash and a gas range. Kitchen also features Cubitac white shaker style cabinets.

  Brad Favreau RE/MAX Bell Park Realty

  239 Barlow Cemetery Rd, Woodstock, CT 06281
• 

  $150,000

  Sold Nov 18, 2025

  9 Sherman Rd, Woodstock, CT 06281

  • 2 Beds
  • 1 Bath
  • 888 Sq Ft
  • Built 1951

  Last Sold Summary

  • 21% Below List Price
  • $169/SF
  • 23 Days On Market

  Last Listing Agent Ryan Braunagel Keller Williams Realty Prtnrs.

  9 Sherman Rd, Woodstock, CT 06281
• 

  Est $387,594

  Not Listed For Sale

  927 Brickyard Rd, Woodstock, CT 06281

  • 3 Beds
  • 1.5 Baths
  • 1,480 Sq Ft
  • Built 1989

  927 Brickyard Rd, Woodstock, CT 06281

  Last Sold Summary

  • 2 Days On Market
• 

  

  /40

  $375,000

  • 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
• 

  $210,000

  Sold Oct 10, 2025

  00 Joy Rd, Woodstock, CT 06281

  • Land
  • 5.11 Acres
  • $41,096 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 180 Days On Market

  Last Listing Agent Elizabeth Scranton Kazantzis Real Estate, LLC

  00 Joy Rd, Woodstock, CT 06281
• 

  Est $522,670

  Not Listed For Sale

  75 Valley View Rd, Woodstock Valley, CT 06282

  • 3 Beds
  • 2.5 Baths
  • 1,954 Sq Ft
  • Built 2005

  75 Valley View Rd, Woodstock Valley, CT 06282

  Last Sold Summary

  • 30 Days On Market
• 

  

  /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
• 

  $45,000

  Sold Jul 03, 2025

  00 Red Cedar Rd, Woodstock, CT 06281

  • Land
  • 17,424 Sq Ft
  • $112,500 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 46 Days On Market

  Last Listing Agent Jennifer Holt Coldwell Banker Realty

  00 Red Cedar Rd, Woodstock, CT 06281
• 

  Est $301,666

  Not Listed For Sale

  1796 Route 197 Unit A, Woodstock, CT 06281

  • 3 Beds
  • 2.5 Baths
  • 2,086 Sq Ft
  • Built 2003

  1796 Route 197 Unit A, Woodstock, CT 06281

  Last Sold Summary

  • 153 Days On Market
• 

  

  /15

  $74,900

  • Land
  • 17,424 Sq Ft
  • $187,250 per Acre

  182 Baxter Rd, Woodstock, CT 06281

  Imagine waking each morning to shimmering lake views and the peaceful sounds of nature. Tucked away on a quiet dead-end road in Woodstock's coveted Quassett Lake community, this exceptional homesite offers the rare opportunity to create a custom retreat in one of northeastern Connecticut's most treasured settings. Perched above the road with a gentle rise in elevation, the property enjoys

  Jennie Kesselman Berkshire Hathaway NE Prop.

  182 Baxter Rd, Woodstock, CT 06281
• 

  $125,000

  Sold Sep 29, 2025

  0 Rocky Hill Rd Unit 24123768, Woodstock, CT 06281

  • Land
  • 7.5 Acres
  • $16,667 per Acre

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Sheena Ruggirello Real Broker CT, LLC

  0 Rocky Hill Rd Unit 24123768, Woodstock, CT 06281
• 

  Est $471,626

  Not Listed For Sale

  109 Tripp Rd, Woodstock, CT 06281

  • 4 Beds
  • 2.5 Baths
  • 2,617 Sq Ft
  • Built 1975

  109 Tripp Rd, Woodstock, CT 06281

  Last Sold Summary

  • 4 Days On Market
• 

  

  /38

  $595,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,464 Sq Ft

  1393 Route 169, Woodstock, CT 06281

  Set far off the road down a beautifully paved driveway, this classic New England Colonial offers the perfect blend of privacy, charm, and desirable location. Nestled on 2.2 picturesque acres in sought-after Woodstock-just a short distance from the Massachusetts line-this beautiful home welcomes you with timeless curb appeal, ample parking, and a peaceful setting that feels like your own private

  Skyla Gagnon RE/MAX Bell Park Realty

  1393 Route 169, Woodstock, CT 06281
• 

  $3,900,000

  Sold Apr 24, 2026

  23 Pine Crest Ridge, Woodstock, CT 06281

  • 9 Beds
  • 8 Baths
  • 14,103 Sq Ft
  • Built 1987

  Last Sold Summary

  • 10% Below List Price
  • $277/SF
  • 128 Days On Market

  Current Estimated Value $3,218,795

  Last Listing Agent Lisa Cozzi Century 21 AllPoints Realty

  23 Pine Crest Ridge, Woodstock, CT 06281
• 

  Est $359,415

  Not Listed For Sale

  7 Hemlock Dr, Woodstock Valley, CT 06282

  • 3 Beds
  • 1 Bath
  • 1,608 Sq Ft
  • Built 1971

  7 Hemlock Dr, Woodstock Valley, CT 06282

  Last Sold Summary

  • 19 Days On Market
• 

  

  /7

  $85,000

  • Land
  • 38,332 Sq Ft
  • $96,591 per Acre

  0 Aplin Hill Ln, Woodstock, CT 06282

  The perfect blend of privacy and community. Lot 4 is the only rear lot in this quiet Woodstock Valley cul-de-sac, a rare chance to build in a growing neighborhood while enjoying the privacy of a wooded .88-acre setting. Conservation land borders the northern and eastern edges, creating a natural buffer that sets this lot apart from the rest. With construction now underway on neighboring Lots 3, 5

  Kristen Kaskela Berkshire Hathaway NE Prop.

  0 Aplin Hill Ln, Woodstock, CT 06282
• 

  $415,000

  Sold Feb 17, 2026

  381 Bungay Hill Rd, Woodstock, CT 06281

  • 4 Beds
  • 1.5 Baths
  • 1,904 Sq Ft
  • Built 1993

  Last Sold Summary

  • 7% Below List Price
  • $218/SF
  • 130 Days On Market

  Current Estimated Value $422,836

  Last Listing Agent Anna Marsh BHHS Realty Professionals

  381 Bungay Hill Rd, Woodstock, CT 06281
• 

  Est $404,644

  Not Listed For Sale

  59 Oak Dr, Woodstock Valley, CT 06282

  • 3 Beds
  • 1.5 Baths
  • 1,306 Sq Ft
  • Built 1992

  59 Oak Dr, Woodstock Valley, CT 06282

  Last Sold Summary

  • 14 Days On Market
• 

  

  /40

  $1,275,000

  • 4 Beds
  • 3.5 Baths
  • 3,868 Sq Ft

  95 Pole Bridge Rd, Woodstock, CT 06281

  This extraordinary waterfront estate on Chamberlain Lake offers a lifestyle rarely found in Connecticut. With 200ft of private lake frontage, this custom post-and-beam Cape was thoughtfully crafted using timber milled directly from trees harvested on the property, creating a residence that is as authentic as it is remarkable. A dramatic center chimney anchors the home, while wide-board pine

  Kate Lombardi Coccomo Real Estate LLC

  95 Pole Bridge Rd, Woodstock, CT 06281
• 

  $208,000

  Sold Sep 15, 2025

  326 Route 169, Wood Stock, CT 06281

  • 3,008 Sq Ft
  • Built 1833

  Last Sold Summary

  • 4% Above List Price
  • $69/SF
  • 13 Days On Market

  Last Listing Agent Diane White Berkshire Hathaway NE Prop.

  326 Route 169, Wood Stock, CT 06281
• 

  Est $688,487

  Not Listed For Sale

  189 New Sweden Rd, Woodstock, CT 06281

  • 5 Beds
  • 4 Baths
  • 3,316 Sq Ft
  • Built 1989

  189 New Sweden Rd, Woodstock, CT 06281

  Last Sold Summary

  • 59 Days On Market
• 

  

  /38

  $499,900

  $5K PRICE DROP Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,700 Sq Ft

  35 Lebanon Hill Rd, Woodstock, CT 06281

  MOTIVATED SELLER...Welcome to 35 Lebanon Hill Road, a beautifully maintained home nestled in one of Woodstock's most sought-after areas. This property offers the perfect blend of rural charm and modern updates, set against the peaceful backdrop that makes Woodstock such a desirable place to make your home. Significant recent improvements provide both value and peace of mind, including a brand new

  Joshua Patraw eXp Realty

  35 Lebanon Hill Rd, Woodstock, CT 06281
• 

  $410,000

  Sold Dec 11, 2025

  278 Child Rd, Woodstock, CT 06281

  • 3 Beds
  • 2.5 Baths
  • 1,094 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Above List Price
  • $375/SF
  • 6 Days On Market

  Current Estimated Value $411,095

  Last Listing Agent Heather Armbruster Lamacchia Realty

  278 Child Rd, Woodstock, CT 06281
• 

  Est $368,831

  Not Listed For Sale

  15 Wainwright Dr, Woodstock, CT 06281

  • 3 Beds
  • 1 Bath
  • 1,276 Sq Ft
  • Built 1950

  15 Wainwright Dr, Woodstock, CT 06281

  Last Sold Summary

  • 17 Days On Market
• 

  

  /40

  $635,000

  $25K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 2,604 Sq Ft

  63 May Brook, Woodstock, CT 06281

  First time offered, original owner & WBA built 2,600 sq. ft. Ranch located in a desired area of Woodstock. This home features 3 bedrooms, 2.5 bathrooms, first floor laundry, designated office space, 2 car oversized garage, along with a finished walk-up second floor bonus room over the garage. The kitchen has plenty of working space, granite counters, along with an eating space overlooking the

  Ryan LaJoie Johnston & Associates Real Estate, LLC

  63 May Brook, Woodstock, CT 06281

Showing Results 81 - 120, Page 3 of 18