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Deep River, CT Houses for Sale

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  • 593 Route 148, Killingworth, CT 06419
    593 Route 148, Killingworth, CT 06419
    593 Route 148, Killingworth, CT 06419
    /39

    $599,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 3.5 Baths
    • 2,564 Sq Ft

    593 Route 148, Killingworth, CT 06419

    This home will not disappoint and is a pleasure to show!!! Charming Renovated Farmhouse on Nearly 5 Acres. A timeless classic reimagined with modern comforts, this beautifully renovated vintage farmhouse blends character and charm with thoughtful updates throughout. The stunning chef's kitchen features GE Cafe appliances, abundant cabinetry, a center island, and a delightful breakfast nook. A

    Agent Photo

    Cathy Lynch

    Coldwell Banker Realty

    (860) 650-5323

    593 Route 148, Killingworth, CT 06419
  • 10 & 12 Firetower Rd, Killingworth, CT 06419
    10 & 12 Firetower Rd, Killingworth, CT 06419
    10 & 12 Firetower Rd, Killingworth, CT 06419
    /39

    $2,750,000

    • 10 Beds
    • 8.5 Baths
    • 4,734 Sq Ft

    10 & 12 Firetower Rd, Killingworth, CT 06419

    Turn into the driveway and the stunning surroundings will melt your stress away. A rare find of two properties on 20+ acres of exquisite grounds bordered by Chatfield Hollow Park and includes a private residence, caretaker's dwelling, and a cabin that feels like you're miles away in a wilderness lodge. The primary residence, a 5 bedroom, 3 bath mid-century modern with an infinity-edge pool that

    Agent Photo

    Betsy Anderson

    William Pitt Sotheby's Int'l

    (860) 431-3151

    10 & 12 Firetower Rd, Killingworth, CT 06419
  • 95 Shailer Pond Rd, Deep River, CT 06417
    95 Shailer Pond Rd, Deep River, CT 06417
    95 Shailer Pond Rd, Deep River, CT 06417
    /40

    $1,017,000 Open Sun 12PM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 4,341 Sq Ft

    95 Shailer Pond Rd, Deep River, CT 06417

    Modern Contemporary Cape with Panoramic Water Views in Deep River and Chester, bordering Connecticut's second-largest forest and surrounded by hundreds of acres of protected land, this striking modern Cape offers the perfect blend of privacy, natural beauty, and upscale living. Perched to take full advantage of stunning panoramic views over Shailer Pond, this home brings the outdoors in from

    Rachel Welch William Raveis Real Estate

    95 Shailer Pond Rd, Deep River, CT 06417
  • 14 Ely Ln, Killingworth, CT 06419
    14 Ely Ln, Killingworth, CT 06419
    14 Ely Ln, Killingworth, CT 06419
    /40

    $1,389,000

    • 4 Beds
    • 3.5 Baths
    • 4,072 Sq Ft

    14 Ely Ln, Killingworth, CT 06419

    Killingworth CT-Stunning 4072 sf 4 bedroom, 3 1/2 bath masterfully built Colonial. This beyond compare property must be seen. Owners have created an outstanding wellness retreat. Tour it by appointment to understand the PRIVACY, joy of nature + obvious lifestyle amenities: Gunite salt water heated pool, several patio areas, beautiful fenced in established gardens plus an additional fenced in area

    Laurie McCann William Pitt Sotheby's Int'l

    14 Ely Ln, Killingworth, CT 06419
  • 180 Green Hill Rd, Killingworth, CT 06419
    180 Green Hill Rd, Killingworth, CT 06419
    180 Green Hill Rd, Killingworth, CT 06419
    /40

    $1,499,900

    • 4 Beds
    • 4 Baths
    • 4,154 Sq Ft

    180 Green Hill Rd, Killingworth, CT 06419

    Step into timeless elegance at this magnificent 1760 Colonial estate, beautifully restored to blend historic charm with modern comfort. Nestled on 8.2 acres of picturesque land, this 4,300 sq. ft. home features four spacious bedrooms and four full bathrooms, including a stunning primary suite with a fireplace, sitting room, and dressing area. Enjoy the warmth of six working fireplaces, a newly

    James Luth HERE Realty

    180 Green Hill Rd, Killingworth, CT 06419
  • 0 Glen Grove Rd, Deep River, CT 06417
    0 Glen Grove Rd, Deep River, CT 06417
    0 Glen Grove Rd, Deep River, CT 06417
    /7

    $899,999 New Construction

    • 4 Beds
    • 2.5 Baths
    • 3,300 Sq Ft

    0 Glen Grove Rd, Deep River, CT 06417

    Introducing an opportunity to build your dream home on a secluded 3-acre interior lot in beautiful Deep River. Located off scenic Glen Grove Road, this custom-designed Modern Farmhouse offers over 3,300 sq ft of thoughtfully planned living space, blending timeless architecture with the flexibility to tailor finishes to your vision. This to-be-built home features 4 bedrooms, 2.5 bathrooms, and a

    Wes Jenks Jenks Realty

    0 Glen Grove Rd, Deep River, CT 06417
  • 95 Cedar Swamp Rd, Chester, CT 06412
    95 Cedar Swamp Rd, Chester, CT 06412
    95 Cedar Swamp Rd, Chester, CT 06412
    /40

    $1,017,000

    • 4 Beds
    • 3.5 Baths
    • 4,341 Sq Ft

    95 Cedar Swamp Rd, Chester, CT 06412

    Modern Contemporary Cape with Panoramic Water Views in Deep River and Chester. Bordering Connecticut's second-largest forest and surrounded by hundreds of acres of protected land, this striking modern Cape offers the perfect blend of privacy, natural beauty, and upscale living. Perched to take full advantage of stunning views over Shailer Pond, this home brings the outdoors in from every angle.

    Rachel Welch William Raveis Real Estate

    95 Cedar Swamp Rd, Chester, CT 06412
  • 88 Winthrop Rd, Chester, CT 06412
    88 Winthrop Rd, Chester, CT 06412
    88 Winthrop Rd, Chester, CT 06412
    /4

    $985,000

    • 2 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    88 Winthrop Rd, Chester, CT 06412

    The charming 3 bedroom colonial with a large attached garage and 2 outbuildings overlooks a lovely 5 acre pond. The home features a large kitchen and 2 1/2 baths with laundry on the second floor. Highlighting the living room is a 30 ft. Cathedral ceiling. Master bedroom includes an interior balcony, overlooking the living area. Generous windows and sliders afford beautiful open views of the

    Peter Walsh Re/Max Valley Shore

    88 Winthrop Rd, Chester, CT 06412
  • 17 Lookout Hill, Essex, CT 06426
    17 Lookout Hill, Essex, CT 06426
    17 Lookout Hill, Essex, CT 06426
    /37

    $1,349,000

    • 5 Beds
    • 6 Baths
    • 5,364 Sq Ft

    17 Lookout Hill, Essex, CT 06426

    An impressive and enchanting private retreat set on 1.51 acres atop a quiet cul-de-sac minutes from Essex village and the CT river. The perfect sanctuary for those seeking tranquility with room to entertain family and friends. Recent updates include new skylights, a freshly painted interior, and refinished wide-board hardwood flooring. 4,714 SF - PLUS a very useful 650 SF walk-out lower level

    Rick Weiner William Pitt Sotheby's Int'l

    17 Lookout Hill, Essex, CT 06426
  • 193 Emanuel Church Rd, Killingworth, CT 06419
    193 Emanuel Church Rd, Killingworth, CT 06419
    193 Emanuel Church Rd, Killingworth, CT 06419
    /9

    $420,000

    • 2 Beds
    • 1 Bath
    • 1,004 Sq Ft

    193 Emanuel Church Rd, Killingworth, CT 06419

    Charming Horse Property on 6.9 Acres with 7-Stall Barn! Step back in time with this classic center chimney Cape, noted in town records as early as 1710 - rich with history and character. Set on a beautiful, level 6.9-acre lot, the property is ideal for equestrian use and features a 7-stall barn equipped with electricity. You'll find open pastures and original stone walls adding to the timeless

    Al Melotto Total Realty Services LLC

    193 Emanuel Church 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
  • 8 Route 148, Killingworth, CT 06419
    8 Route 148, Killingworth, CT 06419
    8 Route 148, Killingworth, CT 06419
    /40

    $799,000

    • 4 Beds
    • 3 Baths
    • 3,864 Sq Ft

    8 Route 148, Killingworth, CT 06419

    Tucked away in complete privacy, this stunning post and beam home offers a rare opportunity to live in harmony with nature. Situated on 6.4 acres of wooded serenity, the property is a true retreat and offers many outside features including a tranquil pond, ample space for gardens, hobbies, or simply room to roam. The home itself showcases timeless craftsmanship with exposed beams, soaring

    Kara Bell J.M. REALTY

    8 Route 148, Killingworth, CT 06419
  • 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
  • 538 Winthrop Rd Unit 5, Deep River, CT 06417
    538 Winthrop Rd Unit 5, Deep River, CT 06417
    538 Winthrop Rd Unit 5, Deep River, CT 06417
    /39

    $363,900

    • 1 Bed
    • 1 Bath
    • 786 Sq Ft

    538 Winthrop Rd Unit 5, Deep River, CT 06417

    Welcome to 538 Winthrop Rd - a beautifully maintained and elegantly updated bungalow. This charming 1-bedroom, 1-bath home offers 786 sq ft of cozy living space, perfect for a weekend retreat or year-round residence. Step into the spacious kitchen featuring Italian marble countertops with a large island, solid wood white cabinetry, and a stainless steel French-door refrigerator. Just off the

    Santo Gulino William Raveis Real Estate

    538 Winthrop Rd Unit 5, Deep River, CT 06417
  • 131 Burr Hill Rd, Killingworth, CT 06419
    131 Burr Hill Rd, Killingworth, CT 06419
    131 Burr Hill Rd, Killingworth, CT 06419
    /40

    $3,250,000

    • 11 Beds
    • 15 Baths
    • 14,110 Sq Ft

    131 Burr Hill Rd, Killingworth, CT 06419

    Nestled amidst 14.4 acres of idyllic beauty, this magnificent country estate is not just a residence; It's a lifestyle, a retreat that transcends the ordinary. Upon entering, you are greeted by a grand foyer that sets the tone of exquisite craftsmanship and luxury that carries throughout the home. The first floor flows seamlessly upon 10 inch oak floors with original antique nailing. The

    Melanie Scull William Pitt Sotheby's Int'l

    131 Burr Hill Rd, Killingworth, CT 06419
  • 323 River Rd, Deep River, CT 06417
    323 River Rd, Deep River, CT 06417
    323 River Rd, Deep River, CT 06417
    /35

    $4,495,000

    • 5 Beds
    • 5.5 Baths
    • 5,557 Sq Ft

    323 River Rd, Deep River, CT 06417

    Rare opportunity to own this gorgeous waterfront estate on the prestigious River Road. Less than three miles to Essex Village, this custom architected dream home is situated on the property to have water views from every room. A deep water electric dock overlooks hundreds of acres of spectacular conservation land across the Connecticut River. Discover unparalleled elegance and waterfront

    Colette Harron William Pitt Sotheby's Int'l

    323 River Rd, Deep River, CT 06417
  • 464 Roast Meat Hill Rd, Killingworth, CT 06419
    464 Roast Meat Hill Rd, Killingworth, CT 06419
    464 Roast Meat Hill Rd, Killingworth, CT 06419
    /37

    $489,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,189 Sq Ft

    464 Roast Meat Hill Rd, Killingworth, CT 06419

    Antique 3 bedroom home on 1 acre lot in Killingworth, surrounded on three sides by state land and a lovely babbling brook. Built in 1890, property was once the site of a Grist Mill. The foundation still visible. Home has been totally remodeled to todays standards, keeping all the charm of days past. Newer kitchen, roof, windows and includes a full house generator. Central air and detached garage.

    Deborah Pach Compass Connecticut, LLC

    464 Roast Meat Hill Rd, Killingworth, CT 06419
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 113 days on the market compared to the national average of 70 days. The median sale price for homes in Deep River, CT over the last 12 months is $752,500, down 28% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$752,500
Median Single Family Sale Price
$1,017,000
Average Price Per Sq Ft
$314
Number of Homes for Sale
1
Last 12 months Home Sales
1
Months of Supply
12.00
Median List Price
$1,017,000
Median Change From 1st List Price
14%
Median Home Sale Price YoY Change
-28%
How to Buy a Home How to Finance a Home How to Sell a Home

In Deep River, there are currently 17 houses for sale, offering an array of options for potential buyers. With houses priced between $329,875 to $4,495,000, there's a range to accomodate every budget. As of August, 2025 the median home price in Deep River is $1,017,000, while the average sale price is $752,500, offering insights into the local housing market. On average, houses spend 113 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.

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.

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