10

Deep River, CT Houses for Sale

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  • 30 Chestnut Hill Rd, Killingworth, CT 06419
    30 Chestnut Hill Rd, Killingworth, CT 06419
    30 Chestnut Hill Rd, Killingworth, CT 06419
    /38

    $340,000

    • 4 Beds
    • 1 Bath
    • 1,756 Sq Ft

    30 Chestnut Hill Rd, Killingworth, CT 06419

    ** A Unique Opportunity at 30 Chestnut Hill Road, Killingworth** Step into a piece of history with this charming antique home, circa 1820-now available from a seasoned preservationist and architect with decades of experience restoring historic homes and barns. This property has already undergone critical structural repairs and has a watertight roof, setting the stage for the next phase of

    Nutan Pawar DreamHomes Realty LLC

    30 Chestnut Hill Rd, Killingworth, CT 06419
  • 112 Cedar Swamp Rd, Deep River, CT 06417
    112 Cedar Swamp Rd, Deep River, CT 06417
    112 Cedar Swamp Rd, Deep River, CT 06417
    /38

    $625,000

    • 4 Beds
    • 3 Baths
    • 2,969 Sq Ft

    112 Cedar Swamp Rd, Deep River, CT 06417

    Welcome to your dream home at 112 Cedar Swamp Road, Deep River, CT! This charming Cape Cod-style residence, originally built in 1940, has been beautifully renovated to blend classic charm with modern efficiency. With 4 spacious bedrooms and 3 full bathrooms, this home has +/- 2,900 square feet of living space, providing ample room for all your lifestyle needs. Step inside to discover a bright and

    Gigi Giordano Taylor Compass Connecticut, LLC

    112 Cedar Swamp Rd, Deep River, CT 06417
  • 214 Green Hill Rd, Killingworth, CT 06419
    214 Green Hill Rd, Killingworth, CT 06419
    214 Green Hill Rd, Killingworth, CT 06419
    /40

    $899,000

    • 3 Beds
    • 2.5 Baths
    • 2,945 Sq Ft

    214 Green Hill Rd, Killingworth, CT 06419

    Discover the perfect blend of historic New England charm and modern comfort in this 1825 farmhouse set on nearly 8 acres of open fields, mature landscape, and a serene stream fed pond. This 4 bed, 3.5 bath home offers an inviting farmhouse style with thoughtfully updated spaces, original architectural details, and room to live, work, and play. A new custom country kitchen serves as the heart of

    Angela Ruel Berkshire Hathaway NE Prop.

    214 Green Hill Rd, Killingworth, CT 06419
  • 538 Winthrop Rd, Deep River, CT 06417
    538 Winthrop Rd, Deep River, CT 06417
    538 Winthrop Rd, Deep River, CT 06417
    /11

    $329,875

    • 2 Beds
    • 1 Bath
    • 650 Sq Ft

    538 Winthrop Rd, Deep River, CT 06417

    Beautiful 2 bedroom right on Star lake with 50 foot of lake frontage is ready for new owners! This property features natural beauty along with modern living interior finishes. Enjoy your viewing!

    Mikail Naska Eagle Eye Realty PLLC

    538 Winthrop Rd, Deep River, CT 06417
  • 50 Beckwith Rd, Killingworth, CT 06419
    50 Beckwith Rd, Killingworth, CT 06419
    50 Beckwith Rd, Killingworth, CT 06419
    /23

    $449,900 Pre-Foreclosure

    • 4 Beds
    • 3 Baths
    • 2,328 Sq Ft

    50 Beckwith Rd, Killingworth, CT 06419

    Imagine coming home to 3.3 wooded acres, where the only thing you hear first is the wind in the trees and the quiet edge of Chatfield Hollow State Park. This spacious 4-bedroom, 3-bath Colonial offers over 2,600 sq ft of living space, plus a ready to finish walk-out room perfect for a home office, play area, or whatever your next chapter calls for. The contemporary layout has hardwood floors,

    Steven Rivkin Planet Realty, LLC

    50 Beckwith Rd, Killingworth, CT 06419
  • 272 Westbrook Rd, Deep River, CT 06417
    272 Westbrook Rd, Deep River, CT 06417
    272 Westbrook Rd, Deep River, CT 06417
    /38

    $539,000

    • 3 Beds
    • 2.5 Baths
    • 1,728 Sq Ft

    272 Westbrook Rd, Deep River, CT 06417

    Natures kaleidoscope defining this serenely & secluded 4.88 acre property nestled in a private sanctuary of which is incomparably resistant to the external world. The Messerschmidt Brook flows freely through the property, embracing soothing sounds. Driving down the driveway you will be captivated by the framework scenery of unspoiled forestry & the open sunny lot. This magical property is close

    Jodi Miller Lisitano Eagle Eye Realty PLLC

    272 Westbrook Rd, Deep River, CT 06417
  • 209 Main St, Deep River, CT 06417
    209 Main St, Deep River, CT 06417
    209 Main St, Deep River, CT 06417
    /40

    $1,199,999

    • 9 Beds
    • 9 Baths
    • 4,982 Sq Ft

    209 Main St, Deep River, CT 06417

    Experience the timeless beauty of New England living! This meticulously restored 1854 Colonial blends historic charm with modern comfort in the heart of Deep River. Every detail has been thoughtfully preserved or reimagined-from the gleaming pumpkin pine wide-plank floors and custom-milled woodwork to carefully selected reproduction hardware that speaks to its heritage. Six fireplaces grace the

    Diane Devries William Pitt Sotheby's Int'l

    209 Main St, Deep River, CT 06417
  • 179 Route 81, Killingworth, CT 06419
    179 Route 81, Killingworth, CT 06419
    179 Route 81, Killingworth, CT 06419
    /13

    $599,999

    • 3 Beds
    • 2 Baths
    • 1,143 Sq Ft

    179 Route 81, Killingworth, CT 06419

    DO NOT ENTER PRIVATE DRIVE - AGENT MUST accompany You - Private drive brings you to 2.9 beautiful acres. House is being sold AS IS, but the value is in the land. The property includes a raised ranch house, a two car garage and another out building, a wonderful pond with bridge. Location very convenient to Route 81.

    John Izzo William Raveis Real Estate

    179 Route 81, Killingworth, CT 06419
  • 252 River Rd, Deep River, CT 06417
    252 River Rd, Deep River, CT 06417
    252 River Rd, Deep River, CT 06417
    /40

    $6,500,000

    • 5 Beds
    • 7 Baths
    • 7,697 Sq Ft

    252 River Rd, Deep River, CT 06417

    A WORLD-CLASS PRIVATE ESTATE SET ON 9.31 GATED ACRES. Nestled behind a private gated entry, this extraordinary CT River Valley estate is a rare luxury compound of architectural distinction, solitude, & resort-caliber amenities. Thoughtfully composed across 5 distinct structures, the property blends modern luxury, European influences, & timeless craftsmanship amid curated landscapes, stone

    Kiara Rusconi William Raveis Real Estate

    252 River Rd, Deep River, CT 06417
  • 134 River Rd, Essex, CT 06426
    134 River Rd, Essex, CT 06426
    134 River Rd, Essex, CT 06426
    /39

    $2,495,000

    • 5 Beds
    • 7.5 Baths
    • 7,405 Sq Ft

    134 River Rd, Essex, CT 06426

    Commanding one of the highest and most breathtaking viewpoints in Essex, Eagles Peak offers this custom-built Georgian Colonial where elevated Connecticut River and Long Island Sound views take center stage. Privately sited on 9.26 acres, this exceptional estate offers rare seclusion, architectural distinction, and extraordinary water views visible from many principal rooms. Encompassing

    Shawn Atkinson William Pitt Sotheby's Int'l

    134 River Rd, Essex, CT 06426
Connecticut Middlesex County Deep River

Houses for Sale in Deep River, CT

Why Live in Deep River

Deep River, CT is a small New England town with just over 1,000 homes, situated along the Connecticut River. Known for its community-centered atmosphere, residents often encounter familiar faces while enjoying local parks and businesses. The downtown district, Deep River Center, features beloved establishments like the Whistle Stop Café and The Nest Coffee House, a nonprofit employing adults with developmental challenges. High Nine Brewing offers a popular patio for socializing, while Bennett Books provides a community refrigerator for those in need. Housing options range from antique Colonials with modern updates near downtown to newer raised ranches and Cape Cods further out, with prices between $250,000 and $650,000 for single-family homes and $100,000 to $275,000 for condos. Deep River Elementary and Valley Regional High are highly rated schools, contributing to the town's appeal for families. The annual Ancient Deep River Muster Parade and summer farmers market are notable events, adding to the list of things to do. Outdoor enthusiasts can explore Canfield Woods' 300-acre nature preserve or enjoy facilities at Devitt Field and Plattwood Park. The Deep River Marina offers amenities for boating enthusiasts. River Valley Transit provides transportation services, and major cities like New Haven and Hartford are within a 35-mile drive. Potential homebuyers should consider flood insurance due to the town's low-lying areas and proximity to the river.

Learn more about living in Deep River

Home Trends in Deep River, CT

On average, homes in Deep River, CT sell after 55 days on the market compared to the national average of 54 days. The median sale price for homes in Deep River, CT over the last 12 months is $450,000, up 8% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$450,000
Median Single Family Sale Price
$483,625
Average Price Per Sq Ft
$300
Number of Homes for Sale
6
Last 12 months Home Sales
50
Months of Supply
1.40
Median List Price
$462,450
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
8%
How to Buy a Home How to Finance a Home How to Sell a Home

In Deep River, there are currently 10 houses for sale, offering an array of options for potential buyers. With houses priced between $329,875 to $6,500,000, there's a range to accomodate every budget. As of March, 2026 the median home price in Deep River is $462,450, while the average sale price is $490,660, offering insights into the local housing market. On average, houses spend 55 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Deep River, CT and find the perfect place to call home.

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