Woodstock, CT Homes

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  /39

  $699,000

  Open Sat 11AM - 1:30PM

  • 3 Beds
  • 3 Baths
  • 2,702 Sq Ft

  29 Braaten Hill Rd, Woodstock, CT 06281

  Welcome to the Top of Connecticut's Last Green Valley. Views sweep across the east and soak up the sunrise every day from the peak of 12 acres that are exclusively yours. Peaceful adventure and native wildflowers beckon you to embrace it all. Step inside your renovated New England Farmhouse and let the home guide you: hand-hewn beams, wide-plank floors, leaded-glass windows, and a cozy working

  

  Stephen Daly

  KW Legacy Partners

  29 Braaten Hill Rd, Woodstock, CT 06281
• Explore Woodstock

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  /18

  $1,700 Per Month

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • House for Rent

  1129 Route 169, Woodstock, CT 06281

  Spacious 3-bedroom, 1-bath second-floor apartment located in a well-maintained mixed-use building. This unit offers a large, open layout featuring a bright kitchen with ample cabinet space, a combined dining area, and an expansive living room with plenty of natural light. Three bedrooms and a full bath completes the space. Private entrance with exterior stairs leading to the unit. Off-street

  

  Carol Ryniewicz

  CR Premier Properties

  1129 Route 169, Woodstock, CT 06281
• 

  $400,000

  Sold Jun 24, 2026

  50 Old Sawmill Rd, Woodstock, CT 06281

  • 3 Beds
  • 2.5 Baths
  • 1,632 Sq Ft
  • Built 1968

  Last Sold Summary

  • 1% Above List Price
  • $245/SF
  • 26 Days On Market

  Current Estimated Value $400,746

  Last Listing Agent Darius Baturo Berkshire Hathaway NE Prop.

  50 Old Sawmill Rd, Woodstock, CT 06281
• 

  Est $402,143

  Not Listed For Sale

  53 Andrews Rd, Woodstock, CT 06281

  • 4 Beds
  • 3 Baths
  • 1,452 Sq Ft
  • Built 1981

  53 Andrews Rd, Woodstock, CT 06281

  Last Sold Summary

  • 2 Days On Market
• 

  

  

  /10

  $79,700

  • Land
  • 1.92 Acres
  • $41,510 per Acre

  36 Olde Meadow Rd, Woodstock, CT 06281

  Rare opportunity to secure the last premium homesite in one of Woodstock's most desirable areas, Eastwood Estates. This approved building lot is being offered as part of a custom home package with a local established builder. It is not being offered for sale as "land only" and requires a build contract with the designated builder, PMR Home Design and Expansion. Buyers may choose from thoughtfully

  

  Tina Lajoie

  Signature Properties of N.E.

  36 Olde Meadow Rd, Woodstock, CT 06281
• 

  

  /20

  $3,500 Plus Fees

  • 4 Beds
  • 2.5 Baths
  • 1,680 Sq Ft
  • House for Rent

  96 Indian Spring Rd, Woodstock, CT 06281

  Stunning remodeled 4 bedroom, 2.5 bath lakefront home available for rent! This spacious residence boasts modern updates throughout, including a fully renovated kitchen with stainless steel appliances, stylish bathrooms, and fresh flooring. Enjoy breathtaking lake views from the largeopen floor plan and the screened in and open deck-perfect for relaxing or entertaining. With ample natural light, a

  96 Indian Spring Rd, Woodstock, CT 06281
• 

  $625,000

  Sold Sep 22, 2025

  37 Pulpit Rock Rd, Woodstock, CT 06281

  • 4 Beds
  • 2.5 Baths
  • 2,682 Sq Ft
  • Built 1968

  Last Sold Summary

  • 7% Below List Price
  • $233/SF
  • 129 Days On Market

  Last Listing Agent Carol Ryniewicz CR Premier Properties

  37 Pulpit Rock 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

  Last Sold Summary

  • 10 Days On Market
• 

  

  /39

  $299,900

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,229 Sq Ft

  349 Route 197, Woodstock, CT 06281

  Bring your vision to this 3-bedroom, 2-bath Cape set on a 2.5-acre corner lot in Woodstock. Offering a functional layout, hardwood floors throughout much of the home, an attached garage, enclosed porch, and rear deck overlooking the private backyard, this property presents an excellent opportunity for buyers looking to build equity through updates and improvements. The home features a spacious

  

  Carol Ryniewicz

  CR Premier Properties

  349 Route 197, Woodstock, CT 06281
• 

  $524,000

  Sold Oct 20, 2025

  36 Dunleavy Dr, Woodstock, CT 06281

  • 3 Beds
  • 2 Baths
  • 2,036 Sq Ft
  • Built 1960

  Last Sold Summary

  • 5% Below List Price
  • $257/SF
  • 62 Days On Market

  Current Estimated Value $523,435

  Last Listing Agent Diane White Berkshire Hathaway NE Prop.

  36 Dunleavy Dr, Woodstock, CT 06281
• 

  Est $901,630

  Not Listed For Sale

  145 Laurel Hill Dr, Woodstock Valley, CT 06282

  • 3 Beds
  • 2.5 Baths
  • 2,614 Sq Ft
  • Built 2011

  145 Laurel Hill Dr, Woodstock Valley, CT 06282

  Last Sold Summary

  • 2 Days On Market
• 

  

  /25

  $355,000

  $24K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 888 Sq Ft

  57 Beaver Dam Rd, Woodstock Valley, CT 06282

  Adorable year-round home on Lake Bunggee, ideally located across from a private beach with stunning lake views. The main level features vaulted ceilings and an open-concept layout connecting the living room, dining area, and kitchen. There are two bedrooms on the main floor, along with a finished room on the lower level for added space. Enjoy not only the beautiful lake views but also a private

  

  Carol Ryniewicz

  CR Premier Properties

  57 Beaver Dam Rd, Woodstock Valley, CT 06282
• 

  $413,000

  Sold Mar 09, 2026

  250 Child Rd, Woodstock, CT 06281

  • 3 Beds
  • 2 Baths
  • 2,326 Sq Ft
  • Built 1981

  Last Sold Summary

  • 18% Above List Price
  • $178/SF
  • 2 Days On Market

  Current Estimated Value $412,384

  Last Listing Agent Joseph Murphy CR Premier Properties

  250 Child Rd, Woodstock, CT 06281
• 

  Est $459,231

  Not Listed For Sale

  51 Tayler Trail, Woodstock Valley, CT 06282

  • 3 Beds
  • 2.5 Baths
  • 1,950 Sq Ft
  • Built 2016

  51 Tayler Trail, Woodstock Valley, CT 06282

  Last Sold Summary

  • 4 Days On Market
• 

  

  /38

  $645,500

  • 3 Beds
  • 2.5 Baths
  • 2,478 Sq Ft

  429 New Sweden Rd, Woodstock, CT 06281

  Step back in time and discover the charm of this beautifully preserved 2,400 sq. ft. farmhouse, originally built in 1805. Rich in character and timeless appeal, this property offers the perfect blend of country living and modern convenience. Whether you dream of cultivating extensive gardens, raising animals, creating a self-sustaining homestead, or simply enjoying wide-open spaces, this property

  

  Elizabeth Scranton

  Kazantzis Real Estate, LLC

  429 New Sweden Rd, Woodstock, CT 06281
• 

  $450,000

  Sold Jun 24, 2026

  53 Prospect St, Woodstock, CT 06281

  • 3 Beds
  • 2.5 Baths
  • 1,736 Sq Ft
  • Built 1956

  Last Sold Summary

  • 6% Above List Price
  • $259/SF
  • 14 Days On Market

  Current Estimated Value $423,990

  Last Listing Agent Skyla Gagnon RE/MAX Bell Park Realty

  53 Prospect St, Woodstock, CT 06281
• 

  Est $499,818

  Not Listed For Sale

  41 Crooked Trail, Wood Stock, CT 06281

  • 4 Beds
  • 2 Baths
  • 1,834 Sq Ft
  • Built 1972

  41 Crooked Trail, Wood Stock, CT 06281

  Last Sold Summary

  • 41 Days On Market
• 

  

  /17

  $75,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 592 Sq Ft

  69 Meadowside Rd, Woodstock, CT 06281

  Your seasonal escape is waiting at Meadowside of Woodstock - a private, gated 100-site co-op campground in Connecticut's Quiet Corner. Lot 69 features TWO structures: a 1999 40-foot Retreat park model with central air, new refrigerator, new deck, and new grill, PLUS a 12x16 log cabin on a concrete slab with electric fireplace and AC. Sleeps 6 total. Fully furnished including brand new sofa.

  

  Robbie Greene Santos

  RE/MAX One

  69 Meadowside Rd, Woodstock, CT 06281
• 

  $476,500

  Sold Jul 11, 2025

  18 Perrin Rd, Woodstock, CT 06281

  • 3 Beds
  • 2 Baths
  • 2,125 Sq Ft
  • Built 1832

  Last Sold Summary

  • 6% Above List Price
  • $224/SF
  • 3 Days On Market

  Current Estimated Value $488,194

  Last Listing Agent Amy Archambault Berkshire Hathaway NE Prop.

  18 Perrin Rd, Woodstock, CT 06281
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  Not Listed For Sale

  00 Child Rd, Woodstock, CT 06281

  00 Child Rd, Woodstock, CT 06281

  Last Sold Summary

  • 56 Days On Market
• 

  

  /40

  $440,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 1,728 Sq Ft

  608 English Neighborhood Rd, Woodstock, CT 06281

  OPEN HOUSE IS CANCELED. Welcome to this spacious Colonial set on a peaceful 1.21-acre lot in the heart of Woodstock's scenic countryside. Offering 4 bedrooms, 3 bathrooms, and over 1,700 square feet of living space, this home is move in ready with all new interior paint. Built in 1987, the property features generous living areas, a primary en-suite, an attached garage, fireplace, and the charm of

  

  Corey Turer

  Real Broker CT, LLC

  608 English Neighborhood Rd, Woodstock, CT 06281
• 

  $565,000

  Sold Jul 18, 2025

  222 Route 197, Woodstock, CT 06281

  • 3 Beds
  • 2 Baths
  • 1,952 Sq Ft
  • Built 1991

  Last Sold Summary

  • $289/SF
  • 8 Days On Market

  Current Estimated Value $568,792

  Last Listing Agent Brooke Gelhaus Compass Connecticut, LLC

  222 Route 197, Woodstock, CT 06281
• 

  Est $729,528

  Not Listed For Sale

  429 Child Rd, Woodstock, CT 06281

  • 3 Beds
  • 4 Baths
  • 3,076 Sq Ft
  • Built 2008

  429 Child Rd, Woodstock, CT 06281

  Last Sold Summary

  • 7 Days On Market
• 

  

  /40

  $425,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  20 Crooked Trail, Woodstock, CT 06281

  Enjoy lake living in this charming Woodstock retreat located directly across the street from Witches Woods Lake, a fully recreational lake offering boating, fishing, swimming, kayaking, and year-round enjoyment. Set on a beautifully landscaped and oversized .60-acre lot with mature gardens, fruit trees, and peaceful outdoor spaces, this property perfectly blends relaxation, recreation, and

  

  Carol Ryniewicz

  CR Premier Properties

  20 Crooked Trail, Woodstock, CT 06281
• 

  

  /24

  $49,900

  Sold Jul 13, 2025

  1340B Connecticut 169, Woodstock, CT 06281

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

  Last Sold Summary

  • 58 Days On Market

  Last Listing Agent Dennis Duga Dr. LAND

  1340B Connecticut 169, Woodstock, CT 06281
• 

  Not Listed For Sale

  208 Baxter Rd, Woodstock, CT 06281

  • 2 Beds
  • 0.5 Baths
  • 480 Sq Ft
  • Built 1947

  208 Baxter Rd, Woodstock, CT 06281

  Last Sold Summary

  • 5 Days On Market
• 

  

  /24

  $595,000

  • Land
  • 100 Acres
  • $5,950 per Acre

  259 Quarry Rd, Woodstock, CT 06281

  Discover the possibilities on this exceptional 100-acre parcel on Quarry Road in scenic Woodstock, Connecticut. Boasting approximately 1,900 feet of road frontage, this expansive property offers a rare combination of privacy, natural beauty, and development potential. The current owner has already cleared three beautiful potential building sites, each positioned to take advantage of the

  

  Carol Ryniewicz

  CR Premier Properties

  259 Quarry Rd, Woodstock, CT 06281
• 

  $357,000

  Sold Jun 26, 2026

  894 Route 169, Woodstock, CT 06281

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft
  • Built 1975

  Last Sold Summary

  • 8% Above List Price
  • $372/SF
  • 3 Days On Market

  Current Estimated Value $344,084

  Last Listing Agent Valerie MacNeil Kazantzis Real Estate, LLC

  894 Route 169, Woodstock, CT 06281
• 

  Est $634,483

  Not Listed For Sale

  3 Holmeslea Ct, Woodstock, CT 06281

  • 5 Beds
  • 2.5 Baths
  • 3,526 Sq Ft
  • Built 1850

  3 Holmeslea Ct, Woodstock, CT 06281

  Last Sold Summary

  • 4 Days On Market
• 

  

  /40

  $674,000

  $16K PRICE DROP Pre-Foreclosure

  • 3 Beds
  • 2.5 Baths
  • 2,626 Sq Ft

  23 Senexet Rd, Woodstock, CT 06281

  Welcome to this stunning 2022-built Colonial set on 2.42 private acres in desirable Woodstock! Tucked back from the road and surrounded by nature, this beautifully maintained 3-bedroom, 2.5-bath home offers the perfect blend of modern comfort and peaceful country living. Step inside to an inviting open-concept layout featuring gleaming hardwood floors, recessed lighting, and abundant natural

  

  Carol Ryniewicz

  CR Premier Properties

  23 Senexet Rd, Woodstock, CT 06281
• 

  $789,000

  Sold Aug 15, 2025

  43 Hiawatha Heights, Woodstock Valley, CT 06282

  • 2 Beds
  • 2 Baths
  • 1,918 Sq Ft
  • Built 1988

  Last Sold Summary

  • $411/SF
  • 42 Days On Market

  Current Estimated Value $795,011

  Last Listing Agent Jennie Kesselman Berkshire Hathaway NE Prop.

  43 Hiawatha Heights, Woodstock Valley, CT 06282
• 

  Est $667,397

  Not Listed For Sale

  739 Route 171, Woodstock, CT 06281

  • 3 Beds
  • 2 Baths
  • 2,277 Sq Ft
  • Built 1977

  739 Route 171, Woodstock, CT 06281

  Last Sold Summary

  • 20 Days On Market
• 

  

  /13

  $799,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,900 Sq Ft

  36 Olde Meadow Rd, Woodstock, CT 06281

  TO BE CONSTRUCTED | Starting at $799,900 Welcome to Eastwood Estates, where luxury living meets the natural beauty and tranquility of Woodstock. Set on a picturesque 1.92-acre homesite bordering protected open space and framed by classic New England stone walls, this offering provides a rare opportunity to BUILD a custom home in one of the area's most desirable neighborhoods. Partner with an

  

  Tina Lajoie

  Signature Properties of New England

  36 Olde Meadow Rd, Woodstock, CT 06281
• 

  $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 $427,257

  Last Listing Agent Lynn Converse RE/MAX Bell Park Realty

  50 Crooked Trail, Woodstock, CT 06281
• 

  

  /39

  Est $508,096

  Not Listed For Sale

  1115 Route 169, Woodstock, CT 06281

  • 3 Beds
  • 2 Baths
  • 2,644 Sq Ft
  • Built 1986

  1115 Route 169, Woodstock, CT 06281

  Last Sold Summary

  • 214 Days On Market
• 

  

  /40

  $375,000

  Pending

  • 2 Beds
  • 1 Bath
  • 1,274 Sq Ft

  140 Tripp Rd, Woodstock, CT 06281

  This residence offers a rare opportunity to inhabit a piece of Woodstock's history. Originally commissioned in 1840 and crafted by William Hammond of Woodstock Hill, the structure served as the Harrisville District School, educating the youth of Pomfret, Thompson, and Woodstock for eight decades. After closing its doors as a place of learning in 1920, it has been meticulously preserved and

  Heather Sawyer William Pitt Sotheby's Int'l

  140 Tripp 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 $651,981

  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
• 

  

  /34

  $749,900

  Pending

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

  234 Pole Bridge Rd, Woodstock, CT 06281

  Here's your chance to own you personal private oasis! Nestled way back away off the beaten path, this property comes with over 25 acres, multiple level clearings with ample opportunity, heart shaped pond, abundance of wildlife, amazing sunsets, etc. This truly is a property of a lifetime! If you want privacy and love the outdoors, this is a dream come true. At the same time, it's perfect for

  Matthew Huberdault Byrnes Real Estate Company

  234 Pole Bridge Rd, Woodstock, CT 06281
• 

  $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 $683,497

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

  170 Lyon Hill Rd, Woodstock, CT 06281

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