4,428

Woodstock, CT Homes

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  • /11

    $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

    Agent Photo

    Tina Lajoie

    Signature Properties of N.E.

    36 Olde Meadow Rd, Woodstock, CT 06281
  • 140 Tripp Rd, Woodstock, CT 06281

    $360,000

    Sold Jun 26, 2026

    140 Tripp Rd, Woodstock, CT 06281

    • 2 Beds
    • 1 Bath
    • 1,274 Sq Ft
    • Built 1840

    Last Sold Summary

    • 4% Below List Price
    • $283/SF
    • 3 Days On Market

    Current Estimated Value $362,741

    Last Listing Agent Heather Sawyer William Pitt Sotheby's Int'l

    140 Tripp Rd, Woodstock, CT 06281
    • 21 Old Sawmill Rd, Woodstock, CT 06281

      Est $495,173

      Not Listed For Sale

      21 Old Sawmill Rd, Woodstock, CT 06281

      • 3 Beds
      • 2 Baths
      • 1,564 Sq Ft
      • Built 2007
      21 Old Sawmill Rd, Woodstock, CT 06281

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Devin Alicea-Bailey Byrnes Real Estate Company

  • /14

    $199,900

    Under Contract
    • 2 Beds
    • 1 Bath
    • 832 Sq Ft

    12 Fawn Ridge, Woodstock, CT 06281

    Welcome to this beautifully renovated 832 sq. ft. end-unit condo in Woodstock, CT, offering an inviting opportunity to trade renting for owning and start building equity of your own. Freshly updated with new paint and flooring, this home provides a clean, comfortable setting that's ready for you to make your own. As an end unit, the home offers added privacy and a desirable layout. Whether you're

    Agent Photo

    Elizabeth Scranton

    Kazantzis Real Estate, LLC

    12 Fawn Ridge, Woodstock, CT 06281
  • 234 Pole Bridge Rd, Woodstock, CT 06281

    $715,000

    Sold Aug 11, 2026

    234 Pole Bridge Rd, Woodstock, CT 06281

    • 4 Beds
    • 2 Baths
    • 2,016 Sq Ft
    • Built 2010

    Last Sold Summary

    • 5% Below List Price
    • $355/SF
    • 54 Days On Market

    Current Estimated Value $741,454

    Last Listing Agent Matthew Huberdault Byrnes Real Estate Company

    234 Pole Bridge Rd, Woodstock, CT 06281
    • 37 Pulpit Rock Rd, Woodstock, CT 06281

      Not Listed For Sale

      37 Pulpit Rock Rd, Woodstock, CT 06281

      • 4 Beds
      • 2.5 Baths
      • 2,682 Sq Ft
      • Built 1968
      37 Pulpit Rock Rd, Woodstock, CT 06281

      Last Sold Summary

      • 129 Days On Market

      Last Listing Agent Carol Ryniewicz CR Premier Properties

  • /22

    $299,900

    • Land
    • 79 Acres
    • $3,796 per Acre

    00 Ide Perrin Rd, Woodstock, CT 06281

    On a private road surrounded by unspoiled natural beauty, this remarkable 79-acre property offers exceptional privacy and endless potential. Two brooks enhance the landscape - Lebanon Brook along the western boundary and Porter Pond Brook to the east. The land features a mix of wetlands and highlands, heavily wooded with abundant timber resources. Create your secluded homestead in the wilderness

    Agent Photo

    Catherine Howard

    Berkshire Hathaway NE Prop.

    00 Ide Perrin Rd, Woodstock, CT 06281
  • 50 Old Sawmill Rd, 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 $417,276

    Last Listing Agent Darius Baturo Berkshire Hathaway NE Prop.

    50 Old Sawmill Rd, Woodstock, CT 06281
    • 584 Prospect St, Woodstock, CT 06281

      Not Listed For Sale

      584 Prospect St, Woodstock, CT 06281

      • 3 Beds
      • 2.5 Baths
      • 3,983 Sq Ft
      • Built 2004
      584 Prospect St, Woodstock, CT 06281

      Last Sold Summary

      • 60 Days On Market

      Last Listing Agent Jennie Kesselman Berkshire Hathaway NE Prop.

  • /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

    Agent Photo

    Tina Lajoie

    Signature Properties of New England

    36 Olde Meadow Rd, Woodstock, CT 06281
  • 36 Dunleavy Dr, 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 $552,136

    Last Listing Agent Diane White Berkshire Hathaway NE Prop.

    36 Dunleavy Dr, Woodstock, CT 06281
    • 1026 Route 171, Woodstock, CT 06281

      Est $458,395

      Not Listed For Sale

      1026 Route 171, Woodstock, CT 06281

      • 3 Beds
      • 2 Baths
      • 1,728 Sq Ft
      • Built 1998
      1026 Route 171, Woodstock, CT 06281

      Last Sold Summary

      • 74 Days On Market

      Last Listing Agent Daniel Deojay RE/MAX Bell Park Realty

  • /38

    $349,999

    $25K PRICE DROP Pending
    • 2 Beds
    • 1.5 Baths
    • 864 Sq Ft

    70 Hawkins Rd, Woodstock Valley, CT 06282

    Welcome to this charming 2-bedroom, 1.5-bath home that offers the perfect blend of comfort and convenience. Ideal for empty nesters, downsizers, or anyone looking for a fantastic condo alternative, this home provides the privacy of single-family living without the hassle HOA. Step inside and enjoy a warm and inviting layout with comfortable living spaces that make the home feel instantly

    Joyce Teixeira Dream Living Realty, LLC

    70 Hawkins Rd, Woodstock Valley, CT 06282
  • 250 Child Rd, Woodstock, CT 06281

    $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 $463,894

    Last Listing Agent Joseph Murphy CR Premier Properties

    250 Child Rd, Woodstock, CT 06281
    • 72 Lake View Dr, Woodstock, CT 06281

      Est $636,261

      Not Listed For Sale

      72 Lake View Dr, Woodstock, CT 06281

      • 2 Beds
      • 2 Baths
      • 1,338 Sq Ft
      • Built 1970
      72 Lake View Dr, Woodstock, CT 06281

      Last Sold Summary

      • 93 Days On Market

      Last Listing Agent Alexcia Merritt RE/MAX Bell Park Realty

  • /37

    $549,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,230 Sq Ft

    61 Red Cedar Rd, Woodstock Valley, CT 06282

    There's something special about being the first to call a brand-new home your own! Set within a desirable Bunggee lake community in Woodstock Valley, this new construction Cape offers approximately 2,230 sq. ft. of finished living space across three levels with 3 bedrooms and 2.5 baths. The main level features an expansive wraparound kitchen, sliders leading to the back deck, and two separate

    Sheena Ruggirello Real Broker CT, LLC

    61 Red Cedar Rd, Woodstock Valley, CT 06282
  • 53 Prospect St, 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 $436,919

    Last Listing Agent Skyla Gagnon RE/MAX Bell Park Realty

    53 Prospect St, Woodstock, CT 06281
    • 78 Peake Brook Rd, Woodstock, CT 06281

      Est $335,822

      Not Listed For Sale

      78 Peake Brook Rd, Woodstock, CT 06281

      • 3 Beds
      • 2 Baths
      • 1,340 Sq Ft
      • Built 1959
      78 Peake Brook Rd, Woodstock, CT 06281

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Charolotte Cook Berkshire Hathaway NE Prop.

  • /4

    $74,900

    $10K PRICE DROP Pending
    • Land
    • 21,780 Sq Ft
    • $149,800 per Acre

    0 Baxter Rd Unit 24177023, Woodstock, CT 06281

    Build your dream home near the lake! This unique offering includes two adjoining parcels being sold together for a combined total of approximately 0.7 acres. The primary 0.5-acre parcel features a beautiful cleared and level homesite with open grassy space, ideal for new construction. Previous perc testing and a site development plan in 2008 outlines proposed home placement, septic system, and

    Donna Bertram Signature Properties of N.E.

    0 Baxter Rd Unit 24177023, Woodstock, CT 06281
  • 40 Old Sawmill Rd, Woodstock, CT 06281

    $340,000

    Sold Jul 25, 2026

    40 Old Sawmill Rd, Woodstock, CT 06281

    • 3 Beds
    • 1.5 Baths
    • 960 Sq Ft
    • Built 1988

    Last Sold Summary

    • 3% Below List Price
    • $354/SF
    • 44 Days On Market

    Current Estimated Value $340,709

    Last Listing Agent John Downs Berkshire Hathaway NE Prop.

    40 Old Sawmill Rd, Woodstock, CT 06281
    • /2

      Not Listed For Sale

      326 Route 169, Wood Stock, CT 06281

      • 3 Beds
      • 3 Baths
      • 3,008 Sq Ft
      • Built 1833
      326 Route 169, Wood Stock, CT 06281

  • /40

    $245,000

    $105K PRICE DROP Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,640 Sq Ft

    1250 Route 171, Woodstock, CT 06281

    Welcome to this charming colonial with stenciled details that add character & style! This delightful antique property is the perfect fixer upper and features 3 bedrooms, 1 and a 1/2 bathrooms, and a clapboard exterior. Situated on a 0.9 acre lot, this home boasts a garden in the side yard and a large backyard, perfect for outdoor enjoyment. Additionally, a shed provides convenient storage for

    Kara Mazzola First Choice Realty

    1250 Route 171, Woodstock, CT 06281
  • 894 Route 169, 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 $361,855

    Last Listing Agent Valerie MacNeil Kazantzis Real Estate, LLC

    894 Route 169, Woodstock, CT 06281
    • 223 Barlow Cemetery Rd, Woodstock, CT 06281

      Est $823,728

      Not Listed For Sale

      223 Barlow Cemetery Rd, Woodstock, CT 06281

      • 3 Beds
      • 4 Baths
      • 2,323 Sq Ft
      • Built 2011
      223 Barlow Cemetery Rd, Woodstock, CT 06281

      Last Sold Summary

      • 40 Days On Market

      Last Listing Agent John Downs Berkshire Hathaway NE Prop.

  • /11

    $499,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,912 Sq Ft

    8-2 Tayler Trail, Woodstock, CT 06281

    To be built 6.5 room Colonial Home in a cozy neighborhood in Woodstock, At this price, this home will go quick! You have time to make several customized selections. Located on a fairly level and private lot, Tayler Tr is a quiet 20 year old open space subdivision (all homes less 20 years old) located on the Union town line off Tayler Rd, of which the remaining 27.77 acres of the original 44 acres

    Morris Lewis Northeast Realty

    8-2 Tayler Trail, Woodstock, CT 06281
  • 1226 Route 169, Wood Stock, CT 06281

    $199,900

    Sold Jul 24, 2026

    1226 Route 169, Wood Stock, CT 06281

    • 2 Beds
    • 1 Bath
    • 1,248 Sq Ft
    • Built 1890

    Last Sold Summary

    • $160/SF
    • 57 Days On Market

    Current Estimated Value $195,902

    Last Listing Agent Amy Vinal Pine Knoll Real Estate

    1226 Route 169, Wood Stock, CT 06281
    • 65 Hemlock Dr, Woodstock Valley, CT 06282

      Est $441,000

      Not Listed For Sale

      65 Hemlock Dr, Woodstock Valley, CT 06282

      • 3 Beds
      • 2 Baths
      • 1,263 Sq Ft
      • Built 2018
      65 Hemlock Dr, Woodstock Valley, CT 06282

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Valerie MacNeil Kazantzis Real Estate, LLC

  • /26

    $125,000

    • Land
    • 13.6 Acres
    • $9,191 per Acre

    0 Lyon Hill Rd Unit 24202057, Woodstock, CT 06281

    Woodstock 13.60-Acre Residential Home Lot With 643-FT Frontage. Soil Testing, Perc Test Done. Septic Design / Engineering Done Health Dept.Approved. Proposed Site Plan With 4-Bedroom, 2-Car Attached Garage, And Nice Size 30' X 40' Outbuilding / Shop / Detached Garage As Well Done And Ready To Go. Most Of The Property Frontage And Both Driveway Aprons Are On Rte-197 (Old Turnpike Rd) And Continues

    Robert Arute Arute Realty Group LLC

    0 Lyon Hill Rd Unit 24202057, Woodstock, CT 06281
  • 16 Walnut Rd, Woodstock, CT 06281

    $409,900

    Sold Jul 31, 2026

    16 Walnut Rd, Woodstock, CT 06281

    • 3 Beds
    • 2 Baths
    • 1,242 Sq Ft
    • Built 2006

    Last Sold Summary

    • 3% Above List Price
    • $330/SF
    • 5 Days On Market

    Current Estimated Value $411,376

    Last Listing Agent Conrad Allen RE/MAX Professional Associates

    16 Walnut Rd, Woodstock, CT 06281
    • 51 Tayler Trail, Woodstock Valley, CT 06282

      Est $482,674

      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

      Last Listing Agent Nathan Daniel Boston MetroWest, LLC

  • /32

    $164,900

    • Land
    • 22 Acres
    • $7,495 per Acre

    XO Pole Bridge Rd, Woodstock, CT 06281

    Enjoy quiet and privacy out in the boonies! 22 acres on the discontinued portion of Pole Bridge Rd. Discontinued means legal access & legally buildable but access is for property owners only, no public access. Subdivisions are only allowed on town owned & maintained roads so this extremely unique area of 2,000+ acres loaded with wildlife galore will remain natural large parcels. The land is

    Dennis Duga Northeast Realty

    XO Pole Bridge Rd, Woodstock, CT 06281
  • 50 Crooked Trail, 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 $461,268

    Last Listing Agent Lynn Converse RE/MAX Bell Park Realty

    50 Crooked Trail, Woodstock, CT 06281
    • 41 Crooked Trail, Wood Stock, CT 06281

      Est $472,517

      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

      Last Listing Agent Sandie Terenzi KW Legacy Partners

  • /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
  • 25 Route 197 Unit Lot 40, 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
    • 00 Child Rd, Woodstock, CT 06281

      Not Listed For Sale

      00 Child Rd, Woodstock, CT 06281

      00 Child Rd, Woodstock, CT 06281

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Gary Pruitt Century 21 Classic Homes

  • /38

    $600,000

    Open Sat 12PM - 1PM
    • 4 Beds
    • 3 Baths
    • 2,072 Sq Ft

    47 Sherman Rd, Woodstock, CT 06281

    Modern amenities meet unmatched seclusion in this 2,000+ sq ft colonial. A mostly level lot offers abundant green space, fruiting plants, and perennials, while the side deck and yard open to a beautiful natural view of the Still River-ideal for outdoor entertaining or quiet, serene living. Inside, gleaming maple floors lead to a first-floor bedroom with attached pass-through bath, a modern eat-in

    Austin Miglin Realty Negotiations LLC

    47 Sherman Rd, Woodstock, CT 06281
  • 170 Lyon Hill 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 $730,183

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

    170 Lyon Hill Rd, Woodstock, CT 06281
    • 429 Child Rd, Woodstock, CT 06281

      Est $703,038

      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

      Last Listing Agent Jared Meehan RE/MAX Bell Park Realty

  • /37

    $379,000

    Open Sun 12PM - 2PM
    • 3 Beds
    • 1.5 Baths
    • 1,824 Sq Ft

    1619 Route 171, Woodstock Valley, CT 06282

    Move in ready ranch offering updated one level living, a finished walkout basement, and a private, level yard, all in the desirable town of Woodstock! The open concept main floor features hardwood floors, abundant natural light, and an updated kitchen with upgraded cabinetry, countertops, center island, and eat-in area. The kitchen opens to the living room, creating an inviting space for everyday

    Stephanie Lachapelle Compass Connecticut, LLC

    1619 Route 171, Woodstock Valley, CT 06282

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$425,000
Median Single Family Sale Price
$462,000
Median 2 Bedroom Sale Price
$340,000
Median 1 Bedroom Sale Price
$338,500
Average Price Per Sq Ft
$287
Number of Homes for Sale
4,428
Last 12 months Home Sales
98
Months of Supply
2.30
Median List Price
$449,250
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-11%
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