4

Woodstock, CT Homes for Sale under $500,000

Section Image Section Image
  • 20 Crooked Trail, Woodstock, CT 06281
    20 Crooked Trail, Woodstock, CT 06281
    20 Crooked Trail, Woodstock, CT 06281
    /40

    $425,000

    • 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

    Agent Photo

    Carol Ryniewicz

    CR Premier Properties

    (860) 255-2882

    20 Crooked Trail, Woodstock, CT 06281
  • 83 Dodge Rd, Woodstock, CT 06281
    83 Dodge Rd, Woodstock, CT 06281
    83 Dodge Rd, Woodstock, CT 06281
    /25

    $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
  • 35 Lebanon Hill Rd, Woodstock, CT 06281
    35 Lebanon Hill Rd, Woodstock, CT 06281
    35 Lebanon Hill Rd, Woodstock, CT 06281
    /38

    $499,900

    $5K PRICE DROP
    • 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
  • 1063 Lebanon Hill Rd, Southbridge, MA 01550
    1063 Lebanon Hill Rd, Southbridge, MA 01550
    1063 Lebanon Hill Rd, Southbridge, MA 01550
    /28

    $414,900

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,132 Sq Ft

    1063 Lebanon Hill Rd, Southbridge, MA 01550

    This sprawling 3 bed, 2 bath ranch has been cherished for many years, and is ready for its next chapter. Filled with warmth and character, this home offers generously sized living spaces perfect for both everyday living and entertaining. Two fireplaces create cozy gathering spots, adding charm and comfort throughout.A standout feature is the potential in-law setup, complete with its own kitchen,

    Lexie Brunet Brunet & Company Real Estate LLC

    1063 Lebanon Hill Rd, Southbridge, MA 01550
Connecticut Windham County Woodstock

Real Estate & Homes in Woodstock, CT under $500,000

Home Trends in Woodstock, CT

On average, homes in Woodstock, CT sell after 43 days on the market compared to the national average of 58 days. The median sale price for homes in Woodstock, CT over the last 12 months is $460,000, up 9% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$460,000
Median Single Family Sale Price
$500,000
Median 1 Bedroom Sale Price
$268,000
Average Price Per Sq Ft
$280
Number of Homes for Sale
16
Last 12 months Home Sales
99
Months of Supply
1.90
Median List Price
$475,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
9%
How to Buy a Home How to Finance a Home How to Sell a Home

In Woodstock, you'll encounter a variety of homes and houses for sale priced under $500,000, providing affordable options for potential buyers. With 4 listings available, there's a wide selection to explore, from charming bungalows to contemporary townhouses. These properties offer an opportunity to enter the real estate market or diversify your investment portfolio without exceeding your budget. Discover the range of homes for sale under 500k in Woodstock, CT and find the perfect fit for your homeownership goals.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group