4,413

Woodstock, CT Homes

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  • 56 Laurel Hill Dr, 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 $387,860

    Last Listing Agent Vivian Kozey CR Premier Properties

    56 Laurel Hill Dr, Woodstock Valley, CT 06282
    • 538 Center Rd, Woodstock, CT 06281

      Est $447,587 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

      • 12% Above List Price
      • $308/SF
      • 5 Days On Market

      Last Sold Price $400,000

      Last Listing Agent Brooke Coughlin Lamacchia Realty

  • 23 Pine Crest Ridge, Woodstock, CT 06281
    23 Pine Crest Ridge, Woodstock, CT 06281
    23 Pine Crest Ridge, Woodstock, CT 06281
    /29

    $4,320,000 Under Contract

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

    23 Pine Crest Ridge, Woodstock, CT 06281

    Pinecrest Apartments is a meticulously maintained 14-unit residential community situated on 5.5 acres in Woodstock, CT, reflecting clear pride of ownership, durable construction, and sustained tenant demand. Built in 1989, the property is 100% occupied and offers a highly desirable mix of 13 townhome-style units and one ranch-style residence. The unit mix includes: (2) 1BR/1BA, (9) 2BR/1.5BA, (1)

    Lisa Cozzi Century 21 AllPoints Realty

    23 Pine Crest Ridge, Woodstock, CT 06281
  • 33 Playground Dr, 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 $403,310

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

    33 Playground Dr, Woodstock, CT 06281
    • 5 Loyola Road Extension, Woodstock, CT 06281

      Not Listed For Sale

      5 Loyola Road Extension, Woodstock, CT 06281

      • 2 Beds
      • 1 Bath
      • 766 Sq Ft
      • Built 1950
      5 Loyola Road Extension, Woodstock, CT 06281

      Last Sold Summary

      • 6% Above List Price
      • $477/SF
      • 6 Days On Market

      Last Sold Price $365,000

      Last Listing Agent Dave Nielson Keller Williams Realty Leading Edge

  • 1669 Route 169, Woodstock, CT 06281
    1669 Route 169, Woodstock, CT 06281
    1669 Route 169, Woodstock, CT 06281
    /39

    $1,250,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 2,340 Sq Ft

    1669 Route 169, Woodstock, CT 06281

    Welcome to Hilltop Meadows-a one-of-a-kind, 60-acre luxury hay farm nestled in Connecticut's scenic "Quiet Corner." Set high above Route 169 in North Woodstock, this breathtaking property offers rolling meadows, mature forests, and serene privacy just 60 miles from Boston and 150 from Manhattan. The heart of the property is a newly updated 2-bed, 2-bath, 2,340 sq ft farmhouse blending historic

    Ryan De Lello William Pitt Sotheby's International Realty

    1669 Route 169, Woodstock, CT 06281
  • 71 Rawson Rd, 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 $512,400

    Last Listing Agent James Duffer RISE REC

    71 Rawson Rd, Woodstock, CT 06281
    • 214 Woodstock Rd, Woodstock, CT 06281

      Not Listed For Sale

      214 Woodstock Rd, Woodstock, CT 06281

      • 5 Beds
      • 3.5 Baths
      • 3,920 Sq Ft
      • Built 1776
      214 Woodstock Rd, Woodstock, CT 06281

      Last Sold Summary

      • 7% Above List Price
      • $153/SF
      • 10 Days On Market

      Last Sold Price $600,000

      Last Listing Agent Wendy McDonald Century 21 AllPoints Realty

  • 25 Woodstock Meadows, Woodstock, CT 06281
    25 Woodstock Meadows, Woodstock, CT 06281
    25 Woodstock Meadows, Woodstock, CT 06281
    /10

    $238,000

    • 2 Beds
    • 1.5 Baths
    • 1,080 Sq Ft

    25 Woodstock Meadows, Woodstock, CT 06281

    Charming 2-bedroom, 1.5-bath home in the heart of Woodstock Meadows! Bright, open living spaces with a cozy layout perfect for relaxing or entertaining. Kitchen offers ample storage and easy flow to the dining area. Enjoy the private yard, ideal for outdoor gatherings and gardening. Convenient location close to local amenities and scenic Connecticut charm.

    Derek Greene Derek Greene

    25 Woodstock Meadows, Woodstock, CT 06281
  • 25 Connecticut 197, Woodstock, CT 06281

    $28,500 Sold Jun 17, 2025

    25 Connecticut 197, Woodstock, CT 06281

    • 2 Beds
    • 1 Bath
    • 920 Sq Ft
    • Built 1990

    Last Sold Summary

    • 59% Below List Price
    • $31/SF
    • 49 Days On Market

    Last Listing Agent Melanie Taylor Berkshire Hathaway NE Prop.

    25 Connecticut 197, Woodstock, CT 06281
    • 50 Lake View Dr, Woodstock, CT 06281

      Est $749,867 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

      • 15% Above List Price
      • $306/SF
      • 3 Days On Market

      Last Sold Price $650,000

      Last Listing Agent Carol Ryniewicz CR Premier Properties

  • 94 Little Pond Rd, Woodstock, CT 06281
    94 Little Pond Rd, Woodstock, CT 06281
    94 Little Pond Rd, Woodstock, CT 06281
    /20

    $369,900 Open Sat 12PM - 1:30PM

    • 3 Beds
    • 1 Bath
    • 1,118 Sq Ft

    94 Little Pond Rd, Woodstock, CT 06281

    Welcome home to this beautifully maintained 3-bedroom, 1-bath residence nestled on a generous half-acre lot. Perfectly situated for privacy and room to roam, the expansive yard offers endless possibilities-whether you dream of a lush garden, a fire-pit or gathering spot. Step inside and be greeted by warm hardwood floors that flow seamlessly throughout the entire home, creating a bright, cohesive

    Jessica Deojay RE/MAX Bell Park Realty

    94 Little Pond Rd, Woodstock, CT 06281
  • 0 Connecticut 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
    • 1157 Route 169, Woodstock, CT 06281

      Est $490,905 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

      • 1% Above List Price
      • $252/SF
      • 49 Days On Market

      Last Sold Price $485,000

      Last Listing Agent Patrick Sweeney RE/MAX

  • 1200 Route 171, Woodstock, CT 06281
    1200 Route 171, Woodstock, CT 06281
    1200 Route 171, Woodstock, CT 06281
    /21

    $249,900 Pending

    • 3 Beds
    • 1 Bath
    • 1,390 Sq Ft

    1200 Route 171, Woodstock, CT 06281

    Adorable Country home on 3.22 acres with remodeled appliance eat in kitchen with large breakfast bar and pantry. Slider leads to wrap around deck. First floor has a living room and a primary bedroom, full bathroom. Upper level has two bedrooms and an office. This home is 100 years old. It is not shiny and new. There is room for one vehicle in the front and the rest of the parking is behind the

    Christine Johnson RE/MAX One

    1200 Route 171, Woodstock, CT 06281
  • 00 Child Rd, Woodstock, CT 06281

    $109,001 Sold May 09, 2025

    00 Child Rd, Woodstock, CT 06281

    • Land
    • 2.06 Acres
    • $52,913 per Acre

    Last Sold Summary

    • 9% Above List Price
    • 12 Days On Market

    Last Listing Agent Britt Miglietta Berkshire Hathaway NE Prop.

    00 Child Rd, Woodstock, CT 06281
    • 610 Route 197, Woodstock, CT 06281

      Est $378,230 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

      • 2% Below List Price
      • $281/SF
      • 6 Days On Market

      Last Sold Price $385,000

      Last Listing Agent Sheena Ruggirello Real Broker CT, LLC

  • 0 Center Rd, Woodstock, CT 06281
    0 Center Rd, Woodstock, CT 06281
    0 Center Rd, Woodstock, CT 06281
    /7

    $49,900 Pending

    • Land
    • 1.5 Acres
    • $33,267 per Acre

    0 Center Rd, Woodstock, CT 06281

    Lovely 1.5 wooded acres with spring fed pond with over 200 feet of road frontage. Beautiful area of town. Property was perc'd at one time, but hasn't been done in years. Build your dream house in the Woodstock school district. Buyer and buyers agent to due their due diligence.

    Diane White Berkshire Hathaway NE Prop.

    0 Center Rd, Woodstock, CT 06281
  • 64 May Brook, 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 $733,624

    Last Listing Agent Jared Meehan RE/MAX Bell Park Realty

    64 May Brook, Woodstock, CT 06281
    • 6 Old Sawmill Rd, Woodstock, CT 06281

      Est $153,254 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

      • 67% Above List Price
      • $126/SF
      • 90 Days On Market

      Last Sold Price $92,000

      Last Listing Agent Debra Burns Berkshire Hathaway Home Services

  • 95 Underwood Rd, Woodstock, CT 06281
    95 Underwood Rd, Woodstock, CT 06281
    95 Underwood Rd, Woodstock, CT 06281
    /30

    $399,000 Pre-Foreclosure

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    95 Underwood Rd, Woodstock, CT 06281

    Welcome to this beautifully updated 3-bedroom, 1-bath ranch nestled on a scenic 1-acre open lot in desirable Woodstock, CT. This move-in ready home offers comfortable one-level living with modern updates throughout and a bright, inviting layout perfect for everyday living and entertaining. The partially finished basement provides valuable additional living space-ideal for a family room, home

    Kirsten Deorsey CR Premier Properties

    95 Underwood Rd, Woodstock, CT 06281
  • 31 Deer Meadow Ln, 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 $510,246

    Last Listing Agent Mary Collins Berkshire Hathaway NE Prop.

    31 Deer Meadow Ln, Woodstock, CT 06281
    • 32 Beech St, Woodstock, CT 06281

      Est $389,410 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

      • 3% Below List Price
      • $262/SF
      • 5 Days On Market

      Last Sold Price $400,000

      Last Listing Agent Lynn Converse RE/MAX

  • 0 Aplin Hill Ln, Woodstock, CT 06282
    0 Aplin Hill Ln, Woodstock, CT 06282
    0 Aplin Hill Ln, Woodstock, CT 06282
    /7

    $85,000

    • Land
    • 0.88 Acre
    • $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
  • 6 & 8 Stone Bridge Rd, 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
    • 23 Walnut Rd, Woodstock, CT 06281

      Est $463,636 Not Listed For Sale

      23 Walnut Rd, Woodstock, CT 06281

      • 3 Beds
      • 2 Baths
      • 1,482 Sq Ft
      • Built 2005
      23 Walnut Rd, Woodstock, CT 06281

      Last Sold Summary

      • 16% Above List Price
      • $270/SF
      • 8 Days On Market

      Last Sold Price $400,000

      Last Listing Agent Pat Malek First Choice Realty

  • 00 Ide Perrin Rd, Woodstock, CT 06281
    00 Ide Perrin Rd, Woodstock, CT 06281
    00 Ide Perrin Rd, Woodstock, CT 06281
    /28

    $349,900

    • Land
    • 79 Acres
    • $4,429 per Acre

    00 Ide Perrin Rd, Woodstock, CT 06281

    On a private road with Unspoiled Splendor - 79 Acres with 2 brooks on the property. Lebanon Brook on the west side and Porter Pond brook on the east. Some wetlands mixed with some highlands and lots of trees. Absolute seclusion possibe with enough lumber to build and heat your home forever. Carve your homestead out of the Wilderness amongst other large acreage parcels. 300' Road Frontage on Ide

    Catherine Howard Berkshire Hathaway NE Prop.

    00 Ide Perrin Rd, Woodstock, CT 06281
  • 54 Rawson Rd, Woodstock, CT 06281

    $331,500 Sold Apr 25, 2025

    54 Rawson Rd, Woodstock, CT 06281

    • 3 Beds
    • 1.5 Baths
    • 1,583 Sq Ft
    • Built 1895

    Last Sold Summary

    • 1% Above List Price
    • $209/SF
    • 94 Days On Market

    Current Estimated Value $358,614

    Last Listing Agent Margaret Young CR Premier Properties

    54 Rawson Rd, Woodstock, CT 06281
    • 35 Valley View Rd, Woodstock Valley, CT 06282

      Est $463,452 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

      • 7% Above List Price
      • $198/SF
      • 13 Days On Market

      Last Sold Price $432,000

      Last Listing Agent Kristen Kaskela Berkshire Hathaway Home Services

  • 00 Route 171, Woodstock, CT 06281
    00 Route 171, Woodstock, CT 06281
    /2

    $69,900 Pending

    • Land
    • 3.07 Acres
    • $22,769 per Acre

    00 Route 171, Woodstock, CT 06281

    Welcome to Woodstock where you can Build 2 houses side by side! 2 lots available! Ready mid April and build this SUMMER! This 3 acre lot has a shared driveway, but offers plenty of privacy!

    Christine Johnson RE/MAX One

    00 Route 171, Woodstock, CT 06281
  • 223 Barlow Cemetery Rd, Woodstock, CT 06281

    $799,000 Sold Sep 17, 2025

    223 Barlow Cemetery Rd, Woodstock, CT 06281

    • 3 Beds
    • 4 Baths
    • 2,323 Sq Ft
    • Built 2011

    Last Sold Summary

    • 6% Below List Price
    • $344/SF
    • 40 Days On Market

    Current Estimated Value $788,821

    Last Listing Agent John Downs Berkshire Hathaway NE Prop.

    223 Barlow Cemetery Rd, Woodstock, CT 06281
    • 70 Red Cedar Rd, Woodstock Valley, CT 06282

      Est $423,662 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

      • 30% Above List Price
      • $193/SF
      • 2 Days On Market

      Last Sold Price $325,000

      Last Listing Agent Diane White Berkshire Hathaway Home Services

  • 1346 Route 169, Woodstock, CT 06281
    1346 Route 169, Woodstock, CT 06281
    1346 Route 169, Woodstock, CT 06281
    /29

    $265,000 Pending

    • 4 Beds
    • 1.5 Baths
    • 1,440 Sq Ft

    1346 Route 169, Woodstock, CT 06281

    Charming Colonial offering 4 bedrooms, 1.5 bathrooms, and 1,440 square feet of well-designed living space. The main level showcases wide-plank hardwood floors, classic built-ins, and abundant natural light throughout. The kitchen features ample cabinet and counter space and flows seamlessly into the spacious living room. A sliding glass door off the living room leads to the rear deck - ideal for

    John Oliveri Property Works New England

    1346 Route 169, Woodstock, CT 06281
  • 42 Woodstock Meadows Unit 42, Woodstock, CT 06281

    $342,000 Sold Dec 03, 2025

    42 Woodstock Meadows Unit 42, Woodstock, CT 06281

    • 2 Beds
    • 2 Baths
    • 1,541 Sq Ft
    • Built 1985

    Last Sold Summary

    • 1% Above List Price
    • $222/SF
    • 7 Days On Market

    Current Estimated Value $283,599

    Last Listing Agent Derek Greene Derek Greene

    42 Woodstock Meadows Unit 42, Woodstock, CT 06281
    • 209 Crystal Pond Rd, Woodstock Valley, CT 06282

      Est $423,153 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

      • 9% Above List Price
      • $157/SF
      • 61 Days On Market

      Last Sold Price $390,000

      Last Listing Agent Jennifer Pagan RE/MAX

  • 0-1 Connecticut 171, Woodstock, CT 06281
    0-1 Connecticut 171, Woodstock, CT 06281
    /2

    $69,900 Pending

    • Land
    • 2.62 Acres
    • $26,679 per Acre

    0-1 Connecticut 171, Woodstock, CT 06281

    2.62 acres next to a 3 acre lot! Build 2 homes at the same time! These lots are in beautiful Woodstock on the Mass. Line and have a shared driveway and approval will be ready in mid April. You can start building for summer! Both lots are in photos for viewing.

    Christine Johnson RE/MAX One

    0-1 Connecticut 171, Woodstock, CT 06281
  • 1015 Route 198, Woodstock, CT 06281

    $445,000 Sold Jun 10, 2025

    1015 Route 198, Woodstock, CT 06281

    • 3 Beds
    • 1.5 Baths
    • 1,708 Sq Ft
    • Built 1960

    Last Sold Summary

    • 7% Below List Price
    • $261/SF
    • 92 Days On Market

    Current Estimated Value $441,571

    Last Listing Agent Amy Vinal Pine Knoll Real Estate

    1015 Route 198, Woodstock, CT 06281
    • 30 Windswept Dr, 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

      • 4% Below List Price
      • $161/SF
      • 2 Days On Market

      Last Sold Price $405,000

      Last Listing Agent Anna Sava Namnoum William Raveis Real Estate

  • 80 Bungay Hill Rd, Woodstock, CT 06281
    80 Bungay Hill Rd, Woodstock, CT 06281
    80 Bungay Hill Rd, Woodstock, CT 06281
    /39

    $2,500,000

    • 3 Beds
    • 4.5 Baths
    • 4,655 Sq Ft

    80 Bungay Hill Rd, Woodstock, CT 06281

    Welcome to this 80 acre Connecticut Estate, tucked into the rolling hills of Woodstock Ct. This exceptional 4,655 sq ft contemporary home offers a unique living experience with its own privately owned public FAA approved commercial grade airport. The property is a pilot's paradise, featuring a spacious hangar that not only accommodates multiple small planes and helicopters but also offers ample

    Cary Marcoux RE/MAX Bell Park Realty

    80 Bungay Hill Rd, Woodstock, CT 06281
  • 28 Crooked Trail, 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 $443,393

    Last Listing Agent Rich Jenkins Real Broker CT, LLC

    28 Crooked Trail, Woodstock, CT 06281

Showing Results 41 - 80, Page 2 of 18

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