5,007

Woodbury, CT Homes

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  • 339 Main St S, Woodbury, CT 06798
    339 Main St S, Woodbury, CT 06798
    339 Main St S, Woodbury, CT 06798
    /39

    $874,900

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

    339 Main St S, Woodbury, CT 06798

    One of Woodbury's last remaining homes built in the late 1600s. This charming residence offers a unique blend of historic character and modern convenience, ideally situated for those who appreciate easy access to local shops, parks, and restaurants. The interior of the home boasts a rich history with exposed wooden beams, 4 fireplaces, and classic hardwood floors, creating an inviting and warm

    Agent Photo

    Marian Van Egas

    Berkshire Hathaway NE Prop.

    339 Main St S, Woodbury, CT 06798
  • 33 Washington Ave, Woodbury, CT 06798
    33 Washington Ave, Woodbury, CT 06798
    33 Washington Ave, Woodbury, CT 06798
    /31

    $3,750 Per Month

    • 2 Beds
    • 2 Baths
    • 1,968 Sq Ft
    • House for Rent

    33 Washington Ave, Woodbury, CT 06798

    AVAILABLE SEPT 2026 FOR $3,750/MONTH. Stunning over-sized Cape on serene, park-like grounds adjacent to a nature preserve. Fully furnished, this inviting 2 bedroom home has been lovingly renovated with a great eye for detail. Quiet street centrally located in historic Woodbury. Newly finished hardwood oak flooring throughout. Two full bathrooms. The large living room with fireplace also includes

    Agent Photo

    Rebecca Doh

    W. Raveis Lifestyles Realty

    33 Washington Ave, Woodbury, CT 06798
  • 225 Old Sherman Hill Rd, Woodbury, CT 06798

    $1,700,000

    Sold Jan 20, 2026

    225 Old Sherman Hill Rd, Woodbury, CT 06798

    • 4 Beds
    • 4.5 Baths
    • 4,517 Sq Ft
    • Built 1969

    Last Sold Summary

    • 19% Below List Price
    • $376/SF
    • 345 Days On Market

    Current Estimated Value $1,625,322

    Last Listing Agent Maria Taylor Klemm Real Estate Inc

    225 Old Sherman Hill Rd, Woodbury, CT 06798
  • 17 Carriage Ln, Woodbury, CT 06798
    17 Carriage Ln, Woodbury, CT 06798
    17 Carriage Ln, Woodbury, CT 06798
    /40

    $774,900

    $25K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,607 Sq Ft

    17 Carriage Ln, Woodbury, CT 06798

    Center Hall Colonial with Full In-Law! This majestic brick facing home flaunts its location atop a private lot overlooking sprawling scenic views. Main level features a two-story foyer, formal dining room w/hardwoods & pocket doors leading to a high-end kitchen w/stainless steel appliances including a gas stove. The kitchen delivers with granite tops, upscale cabinetry, breakfast bar, & eat-in

    Agent Photo

    Shane Kropo

    RE/MAX RISE

    17 Carriage Ln, Woodbury, CT 06798
  • 302 Tuttle Rd, Woodbury, CT 06798
    302 Tuttle Rd, Woodbury, CT 06798
    302 Tuttle Rd, Woodbury, CT 06798
    /35

    Starting at $1,599 Plus Fees

    • Studio - 2 Beds

    302 Tuttle Rd, Woodbury, CT 06798

    Welcome to Woodbury Knoll Apartments, where modern comfort meets tranquil, lakeside living. Life unfolds at a different pace here — mornings are inspired by nature's quiet beauty, and evenings unwind in serene surroundings. In our apartments in Woodbury, CT, you'll discover a lifestyle that's vibrant yet peaceful, perfectly balanced, and endlessly welcoming.

    Woodbury Knoll

    302 Tuttle Rd, Woodbury, CT 06798
  • 13 Park Ln, Woodbury, CT 06798

    $650,000

    Sold May 28, 2026

    13 Park Ln, Woodbury, CT 06798

    • 3 Beds
    • 2.5 Baths
    • 2,264 Sq Ft
    • Built 1955

    Last Sold Summary

    • $287/SF
    • 0 Days On Market

    Current Estimated Value $635,149

    Last Listing Agent Michael Wright RE/MAX Right Choice

    13 Park Ln, Woodbury, CT 06798
  • 38 Mountain Rd, Woodbury, CT 06798
    38 Mountain Rd, Woodbury, CT 06798
    38 Mountain Rd, Woodbury, CT 06798
    /33

    $494,000

    • 3 Beds
    • 2.5 Baths
    • 1,704 Sq Ft

    38 Mountain Rd, Woodbury, CT 06798

    Welcome to 38 Mountain Road, a perfect blend of functional living space and privacy while still offering a close proximity to town. Upon entering you are greeted with a warm and welcoming living room. This space flows into the dining room which is right next to the remodeled kitchen making dinner hosting a breeze! The kitchen offers a view of your private back yard from the window and beautiful

    Agent Photo

    Tami Hoxhallari

    Lotus Realty Group, LLC.

    38 Mountain Rd, Woodbury, CT 06798
  • 495 Main St S Unit C, Woodbury, CT 06798
    495 Main St S Unit C, Woodbury, CT 06798
    495 Main St S Unit C, Woodbury, CT 06798
    /14

    $1,650

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 525 Sq Ft
    • Condo for Rent

    495 Main St S Unit C, Woodbury, CT 06798

    Enjoy the charm and convenience of living in the heart of Woodbury’s Historic District. This delightful 1 bed/1 bath is ideally situated on Main Street yet set back from the road in a private wooded location, offering both accessibility and tranquility. The cottage features an open living/dining room, a cozy bedroom with bonus space, a 3 piece bathroom, and a charming kitchen with a back

    495 Main St S Unit C, Woodbury, CT 06798
  • 145 Cat Swamp Rd, Woodbury, CT 06798

    $480,000

    Sold Nov 04, 2025

    145 Cat Swamp Rd, Woodbury, CT 06798

    • 3 Beds
    • 1.5 Baths
    • 1,792 Sq Ft
    • Built 1961

    Last Sold Summary

    • 4% Above List Price
    • $268/SF
    • 51 Days On Market

    Current Estimated Value $489,818

    Last Listing Agent Nancy Langrock William Raveis Real Estate

    145 Cat Swamp Rd, Woodbury, CT 06798
  • 76 Cowles Rd, Woodbury, CT 06798
    76 Cowles Rd, Woodbury, CT 06798
    76 Cowles Rd, Woodbury, CT 06798
    /37

    $1,800,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 2,072 Sq Ft

    76 Cowles Rd, Woodbury, CT 06798

    Rare opportunity to own a spectacular 40-acre estate designed for exceptional horse care, training, and country living-while also offering the flexibility to create a private escape tucked away from it all. This remarkable property features a 150' x 80' indoor riding arena with excellent lighting and three overhead doors, along with an immaculate 9-stall barn complete with concrete floors and

    Agent Photo

    Pam Famiglietti

    William Raveis Real Estate

    76 Cowles Rd, Woodbury, CT 06798
  • 31 Pilgrim Trail Unit 31-5 PILGRIM TRAIL, Woodbury, CT 06798
    31 Pilgrim Trail Unit 31-5 PILGRIM TRAIL, Woodbury, CT 06798
    31 Pilgrim Trail Unit 31-5 PILGRIM TRAIL, Woodbury, CT 06798
    /43

    $1,600

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    31 Pilgrim Trail Unit 31-5 PILGRIM TRAIL, Woodbury, CT 06798

    Impeccable large 2nd floor end unit, bright, cheerful and safe location with beautiful views. Freshly painted and professionally cleaned with new carpeting throughout. Rent includes heat, hot water and appliances. Tenant pays electric, cable/internet, renters insurance. Trash and recycling services and all grounds maintenance also included. New mini blinds throughout. Neighborhood is quiet and

    31 Pilgrim Trail Unit 31-5 PILGRIM TRAIL, Woodbury, CT 06798
  • 158 Hazel Plain Rd, Woodbury, CT 06798

    $424,950

    Sold Oct 23, 2025

    158 Hazel Plain Rd, Woodbury, CT 06798

    • 4 Beds
    • 2.5 Baths
    • 2,085 Sq Ft
    • Built 1974

    Last Sold Summary

    • $204/SF
    • 32 Days On Market

    Current Estimated Value $459,801

    Last Listing Agent Michael Ferris eXp Realty

    158 Hazel Plain Rd, Woodbury, CT 06798
  • 20 Stagecoach Rd, Woodbury, CT 06798
    20 Stagecoach Rd, Woodbury, CT 06798
    20 Stagecoach Rd, Woodbury, CT 06798
    /40

    $629,000

    • 4 Beds
    • 2.5 Baths
    • 2,157 Sq Ft

    20 Stagecoach Rd, Woodbury, CT 06798

    Summer opportunity in a highly sought-after neighborhood featuring a private inground pool and backyard retreat. This one checks all the boxes-from cul-de-sac living to privacy and a great setting. Spacious 4-bedroom Colonial with hardwood floors, fireplace, and a partially finished walkout lower level. Sold strictly as-is and priced aggressively for a quick sale. Sellers have secured their next

    Agent Photo

    Robert Leonard

    William Raveis Real Estate

    20 Stagecoach Rd, Woodbury, CT 06798
  • 14 Arrowhead Way Unit 3, Woodbury, CT 06798
    14 Arrowhead Way Unit 3, Woodbury, CT 06798
    14 Arrowhead Way Unit 3, Woodbury, CT 06798
    /61

    $1,500

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    14 Arrowhead Way Unit 3, Woodbury, CT 06798

    Heat and hot water are included with this immaculate first floor condo. Freshly painted and professionally cleaned, this unit is bright and cheerful offering spectacular views. In a small complex on a dead end road with beautifully landscaped grounds. Also included are: fridge, stove/oven, lockable basement storage, snow removal and year round grounds maintenance, trash and recycling services,

    14 Arrowhead Way Unit 3, Woodbury, CT 06798
  • 142 Washington Rd, Woodbury, CT 06798

    $390,000

    Sold Mar 31, 2026

    142 Washington Rd, Woodbury, CT 06798

    • 2 Beds
    • 1 Bath
    • 1,340 Sq Ft
    • Built 1955

    Last Sold Summary

    • 3% Above List Price
    • $291/SF
    • 44 Days On Market

    Current Estimated Value $383,111

    Last Listing Agent Mary Ann Bennett Drakeley Real Estate, Inc.

    142 Washington Rd, Woodbury, CT 06798
  • 54 Clubhouse Dr Unit 54, Woodbury, CT 06798
    54 Clubhouse Dr Unit 54, Woodbury, CT 06798
    54 Clubhouse Dr Unit 54, Woodbury, CT 06798
    /24

    $288,990

    $21K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,916 Sq Ft

    54 Clubhouse Dr Unit 54, Woodbury, CT 06798

    Welcome to this light-filled and beautifully maintained townhome in the highly sought-after Woodlake community in Woodbury. Spanning three levels, this inviting home offers a rare blend of space, comfort, and seasonal views of Wood Lake. The main level features a spacious living and dining area anchored by a striking floor-to-ceiling fireplace, enhanced with a wood-burning insert (2021). Sliding

    Henrik K Kjaer Keller Williams Realty

    54 Clubhouse Dr Unit 54, Woodbury, CT 06798
  • 128 Old Town Farm Rd, Woodbury, CT 06798
    128 Old Town Farm Rd, Woodbury, CT 06798
    128 Old Town Farm Rd, Woodbury, CT 06798
    /32

    $3,900

    Total Monthly Price

    • 4 Beds
    • 3.5 Baths
    • 2,800 Sq Ft
    • House for Rent

    128 Old Town Farm Rd, Woodbury, CT 06798

    Step into serenity with this rare chance to live in this wonderful Woodbury colonial, tucked gently into the trees and surrounded by nature. This 4 bed, 3.5 bath home offers the perfect blend of comfort, character, and modern upgrades.Sip your morning coffee on the elevated porch, watch the seasons change across the river and your private yard, or end the day with a soak in the hot tub.

    128 Old Town Farm Rd, Woodbury, CT 06798
  • 38 Barnhill Rd, Woodbury, CT 06798

    $660,000

    Sold Feb 05, 2026

    38 Barnhill Rd, Woodbury, CT 06798

    • 3 Beds
    • 2.5 Baths
    • 2,835 Sq Ft
    • Built 1986

    Last Sold Summary

    • 5% Below List Price
    • $233/SF
    • 134 Days On Market

    Current Estimated Value $674,130

    Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

    38 Barnhill Rd, Woodbury, CT 06798
  • 819 Main St N, Woodbury, CT 06798
    819 Main St N, Woodbury, CT 06798
    819 Main St N, Woodbury, CT 06798
    /34

    $1,675,000

    $250K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,992 Sq Ft

    819 Main St N, Woodbury, CT 06798

    Open Meadow Farm, a beautifully maintained property offering a blend of rural charm and modern conveniences. Set on 9.88 picturesque acres, this property features three fenced fields, ideal for horses or other livestock and a two-story barn equipped with four stalls, a tack room, gravel storage area and a gleaming concrete main floor. Recent updates include a paved driveway with turnaround, back

    Sindy Butkus Klemm Real Estate Inc

    819 Main St N, Woodbury, CT 06798
  • 28 Leavenworth Rd, Woodbury, CT 06798
    28 Leavenworth Rd, Woodbury, CT 06798
    28 Leavenworth Rd, Woodbury, CT 06798
    /37

    $30,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 3,282 Sq Ft
    • House for Rent

    28 Leavenworth Rd, Woodbury, CT 06798

    STUNNING MEMORIAL DAY - LABOR DAY RENTAL with POOL and TENNIS COURT (with lights). Enjoy a month or all summer at this resort-style escape with newly renovated interior and incredible entertaining space indoors and out. Extraordinary cook's kitchen with breakfast nook opens into an expansive sun-filled room overlooking lawns, tennis court and pool. Updated bedrooms and bathrooms provide a

    Diana Bisselle William Pitt Sotheby's Int'l

    28 Leavenworth Rd, Woodbury, CT 06798
  • 306 Upper Grassy Hill Rd, Woodbury, CT 06798

    $350,000

    Sold Aug 08, 2025

    306 Upper Grassy Hill Rd, Woodbury, CT 06798

    • 3 Beds
    • 2 Baths
    • 1,936 Sq Ft
    • Built 1964

    Last Sold Summary

    • $181/SF
    • 6 Days On Market

    Current Estimated Value $380,667

    Last Listing Agent Shawna Mucherino Coldwell Banker Realty

    306 Upper Grassy Hill Rd, Woodbury, CT 06798
  • 0 Carmel Hill Rd, Woodbury, CT 06798
    0 Carmel Hill Rd, Woodbury, CT 06798
    /2

    $179,900

    Under Contract
    • Land
    • 4 Acres
    • $44,975 per Acre

    0 Carmel Hill Rd, Woodbury, CT 06798

    Discover your own private sanctuary on this enchanting ~4-acre parcel of pristine land perched along scenic Carmel Hill Road in historic Woodbury, CT. Nestled in the heart of Litchfield County's rolling countryside, this remarkable property captivates with mesmerizing views of a sparkling waterfall and the gentle flow of a serene river-nature's own symphony right at your doorstep. Imagine

    Melissa Gordon Coldwell Banker Realty

    0 Carmel Hill Rd, Woodbury, CT 06798
  • 34 Arrowhead Way Unit A1, Woodbury, CT 06798
    34 Arrowhead Way Unit A1, Woodbury, CT 06798
    34 Arrowhead Way Unit A1, Woodbury, CT 06798
    /13

    $1,600 Per Month

    • 1 Bed
    • 1 Bath
    • 546 Sq Ft
    • House for Rent

    34 Arrowhead Way Unit A1, Woodbury, CT 06798

    Well-maintained first-floor end unit featuring a bright living room with beautiful built-in bookshelves, a cozy galley kitchen, and a spacious bedroom. Rent includes heat, hot water, and electricity for added convenience. Located in the Quassuk Heights community, this home offers easy living with plenty of parking, on-site laundry, lower-level storage, and easy walkways from parking to unit.

    Tim Drakeley Drakeley Real Estate, Inc.

    34 Arrowhead Way Unit A1, Woodbury, CT 06798
  • 3 Inwood Ln, Woodbury, CT 06798

    $765,000

    Sold Jul 29, 2025

    3 Inwood Ln, Woodbury, CT 06798

    • 4 Beds
    • 4 Baths
    • 3,330 Sq Ft
    • Built 1986

    Last Sold Summary

    • 13% Below List Price
    • $230/SF
    • 58 Days On Market

    Current Estimated Value $791,366

    Last Listing Agent Elizabeth Newnham William Pitt Sotheby's Int'l

    3 Inwood Ln, Woodbury, CT 06798
  • 48 Coach Light Dr, Woodbury, CT 06798
    48 Coach Light Dr, Woodbury, CT 06798
    48 Coach Light Dr, Woodbury, CT 06798
    /39

    $1,599,000

    $300K PRICE DROP Pending
    • 4 Beds
    • 4.5 Baths
    • 5,216 Sq Ft

    48 Coach Light Dr, Woodbury, CT 06798

    Gloriously Peaceful, Private, Magnificent views...This exceptional residence among similar spectacular homes welcomes you with a dramatic two-story entry - designed for both refined entertaining and comfortable living. The heart of the home is a beautifully appointed chef's kitchen featuring porcelain countertops with waterfall island and slab backsplash. New 48' Sub-Zero refrigerator & a

    Nan Jane Keough William Pitt Sotheby's Int'l

    48 Coach Light Dr, Woodbury, CT 06798
  • 17 Pleasant St, Woodbury, CT 06798
    17 Pleasant St, Woodbury, CT 06798
    17 Pleasant St, Woodbury, CT 06798
    /9

    $2,200 Per Month

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft
    • House for Rent

    17 Pleasant St, Woodbury, CT 06798

    This darling little cottage style cape is in the center of Woodbury's Historic District. Recently painted inside and out, new roof, No smokers, no pets. Good credit a must!(700 FICO) Year lease. Landlord maintains lawn care and snow removal. Tenant pays all utilities!

    Sindy Butkus Klemm Real Estate Inc

    17 Pleasant St, Woodbury, CT 06798
  • 54 Bear Run, Woodbury, CT 06798

    $750,000

    Sold Jun 15, 2026

    54 Bear Run, Woodbury, CT 06798

    • 4 Beds
    • 2.5 Baths
    • 2,849 Sq Ft
    • Built 1998

    Last Sold Summary

    • 7% Above List Price
    • $263/SF
    • 46 Days On Market

    Current Estimated Value $695,019

    Last Listing Agent Becky Hood William Pitt Sotheby's Int'l

    54 Bear Run, Woodbury, CT 06798
  • 5 Kimberly Ln, Woodbury, CT 06798
    5 Kimberly Ln, Woodbury, CT 06798
    5 Kimberly Ln, Woodbury, CT 06798
    /36

    $470,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 1,732 Sq Ft

    5 Kimberly Ln, Woodbury, CT 06798

    Welcome to this beautifully maintained 3-bedroom, 3-bath high ranch nestled in the picturesque New England town of Woodbury. This inviting home offers a perfect blend of comfort, functionality, and modern updates. The upper level features gleaming hardwood floors throughout and an updated kitchen that flows seamlessly into an open-concept dining and living area-ideal for both everyday living and

    Heather Crabtree RE/MAX RISE

    5 Kimberly Ln, Woodbury, CT 06798
  • 300 Railtree Rd, Woodbury, CT 06798
    300 Railtree Rd, Woodbury, CT 06798
    300 Railtree Rd, Woodbury, CT 06798
    /7

    $2,100 Per Month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    300 Railtree Rd, Woodbury, CT 06798

    1-2 BR one bath completely renovated. Laundry in unit, private off street parking. Plowing and lawn maitenance included tenant shovels walk way. Credit check required no smoking or pets

    Doug Rose Scalzo Real Estate

    300 Railtree Rd, Woodbury, CT 06798
  • 31 McVeigh Rd, Woodbury, CT 06798

    $530,000

    Sold May 01, 2026

    31 McVeigh Rd, Woodbury, CT 06798

    • 4 Beds
    • 2.5 Baths
    • 2,256 Sq Ft
    • Built 1987

    Last Sold Summary

    • 12% Below List Price
    • $235/SF
    • 211 Days On Market

    Current Estimated Value $561,003

    Last Listing Agent Jennifer Bundock Coldwell Banker Realty

    31 McVeigh Rd, Woodbury, CT 06798

Showing Results 1 - 40, Page 1 of 18

Connecticut Litchfield County Woodbury

Real Estate & Homes

Home Prices in Woodbury, CT

The median home sale price in Woodbury, CT is $489,500, up 10% year-over-year. Homes in Woodbury sell in 72 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$489,500
Median Single Family Sale Price
$647,450
Median Townhouse Sale Price
$332,500
Median 2 Bedroom Sale Price
$288,995
Median 1 Bedroom Sale Price
$129,250
Average Price Per Sq Ft
$287
Number of Homes for Sale
38
Last 12 months Home Sales
128
Months of Supply
3.60
Median List Price
$542,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
10%
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