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Deep River, CT Houses for Sale

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

    $2,500,000

    • 10 Beds
    • 8.5 Baths
    • 6,588 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) 517-8016

    10 & 12 Firetower Rd, Killingworth, CT 06419
  • 14 Kenilworth Dr, Killingworth, CT 06419
    14 Kenilworth Dr, Killingworth, CT 06419
    14 Kenilworth Dr, Killingworth, CT 06419
    /29

    $649,900

    • 5 Beds
    • 3.5 Baths
    • 2,970 Sq Ft

    14 Kenilworth Dr, Killingworth, CT 06419

    Spacious Raised Ranch on 4.4 Acres with In-Law set up. Oversized Garage Loft! Welcome to your private retreat! Nestled on 4.4 scenic acres, this impressive raised ranch offers flexible living space perfect for multigenerational living, entertaining, or working from home. Step inside to discover a main home featuring bright, open-concept living, generous bedrooms, and a large kitchen with plenty

    Agent Photo

    Eric Bergers

    William Raveis Real Estate

    (860) 775-6542

    14 Kenilworth Dr, Killingworth, CT 06419
  • 62 River St, Deep River, CT 06417
    62 River St, Deep River, CT 06417
    62 River St, Deep River, CT 06417
    /4

    $799,000

    • 4 Beds
    • 2 Baths
    • 1,970 Sq Ft

    62 River St, Deep River, CT 06417

    STEP INSIDE AND PRVIEW THIS UP TO DATE VICTORIAN. Easy to show this remodeled two family HOME, could be converted to single family. move in condition, all new appliances. CLOSE TO TOWN, DRUG STORE, GROCERY AND RESTAURANTS.

    Mim Beardsley Houlihan Lawrence WD

    62 River St, 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
  • 275 Route 148, Killingworth, CT 06419
    275 Route 148, Killingworth, CT 06419
    275 Route 148, Killingworth, CT 06419
    /35

    $879,500

    • 3 Beds
    • 1.5 Baths
    • 2,039 Sq Ft

    275 Route 148, Killingworth, CT 06419

    Tucked away on 20 spectacular acres, this 3-bedroom, 1.5-bath ranch offers the perfect blend of privacy, functionality, and natural beauty. Whether you're looking for a peaceful retreat, a place to start a hobby farm or a place to build your dream home, this property offers endless opportunities. The existing home could even serve as a charming caretaker's cottage, guest house, or temporary

    Shelly Cumpstone Coldwell Banker Realty

    275 Route 148, Killingworth, CT 06419
  • 14 Ely Ln, Killingworth, CT 06419
    14 Ely Ln, Killingworth, CT 06419
    14 Ely Ln, Killingworth, CT 06419
    /40

    $1,349,000

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

    14 Ely Ln, Killingworth, CT 06419

    Killingworth CT - Stunning Colonial of 4072 sf. This 4 bedroom, 3 1/2 baths, masterfully built home is beyond compare. Owners have created an outstanding sanctuary. PRIVACY prevails amidst the joy of nature, + impressive lifestyle amenities: In-ground Gunite salt water heated pool, several patio areas, beautifully fenced in established gardens, plus an additional fenced in area for your family or

    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
  • 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
  • 21 River Ln, Deep River, CT 06417
    21 River Ln, Deep River, CT 06417
    21 River Ln, Deep River, CT 06417
    /39

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 2,018 Sq Ft

    21 River Ln, Deep River, CT 06417

    Remodeled from the ground up this home is ready for new owners to move right in and enjoy! Centrally located to the village center & the CT River, gives you easy access to the town center where you find small shops, grocery store, pharmacy, library, town green & more. In the other direction you are close to the Connecticut River where there is boating, water skiing, kayaking & more. The exterior

    Brian Jermainne Team Jermainne Real Estate Services, LLC

    21 River Ln, Deep River, CT 06417
  • 100 N Tower Hill Rd, Killingworth, CT 06419
    100 N Tower Hill Rd, Killingworth, CT 06419
    100 N Tower Hill Rd, Killingworth, CT 06419
    /19

    $455,000

    • 5 Beds
    • 2 Baths
    • 2,090 Sq Ft

    100 N Tower Hill Rd, Killingworth, CT 06419

    Escape to the country in peaceful Killingworth! Set on 3+ acres with a pool, pond, and horse-friendly zoning, this property offers privacy, nature, and endless potential. Enjoy a quiet setting across from a tree reserve. Recent updates include a new septic system, working well, newer roof sections, and solid furnace. Ideal for buyers ready to customize and create their dream home. Sold AS IS -

    Jason Saphire www.HomeZu.com

    100 N Tower 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
    /39

    $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
  • 46 Hemlock Dr, Deep River, CT 06417
    46 Hemlock Dr, Deep River, CT 06417
    46 Hemlock Dr, Deep River, CT 06417
    /40

    $419,900

    • 4 Beds
    • 1.5 Baths
    • 1,688 Sq Ft

    46 Hemlock Dr, Deep River, CT 06417

    Charming home located just out of town. Nicely laid out for entertaining in and out. Large living room with fireplace and cathedral ceiling. 2 Bedrooms and a full bath on the main floor. 11x20 Eat In Kitchen with granite counter tops. Second floor has a sitting/play area, 2 bedrooms and a 1/2 bath. Rear screened porch overlooks the terraced backyard. Large 13x34 deck steps down to the inground

    Craig Milton Re/Max Valley Shore

    46 Hemlock Dr, 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
  • 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
  • 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
  • 25 Roast Meat Hill Rd, Killingworth, CT 06419
    25 Roast Meat Hill Rd, Killingworth, CT 06419
    25 Roast Meat Hill Rd, Killingworth, CT 06419
    /10

    $879,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 3,554 Sq Ft

    25 Roast Meat Hill Rd, Killingworth, CT 06419

    Country and Convenience! Welcome to 25 Roast Meat Hill. This spacious 4-bedroom, 2.5-bath home offers 3,554 sq. ft. of living space plus over 800 sq. ft. in a finished walk-out lower level, all set on 2.9 acres of peaceful countryside. Enjoy the perfect balance of privacy and convenience, just minutes from local amenities and shoreline attractions. Enter the property via a driveway flanked by

    Claire Kilmer Coldwell Banker Realty

    25 Roast Meat Hill Rd, Killingworth, CT 06419
  • 5 Mitchell Ln, Deep River, CT 06417
    5 Mitchell Ln, Deep River, CT 06417
    5 Mitchell Ln, Deep River, CT 06417
    /30

    $319,900 Open Sun 12PM - 3PM

    • 2 Beds
    • 1.5 Baths
    • 1,081 Sq Ft

    5 Mitchell Ln, Deep River, CT 06417

    With front porch charm, blooming perennial gardens, and that unmistakable storybook feeling, this home instantly captures your heart. Lovingly cared for over the years, it offers the perfect balance of comfort and character. The updated kitchen opens to a sunlit dining and family area, creating a welcoming space for gatherings. A cozy reading nook and an inviting office and half bath makes the

    Nancy Leonard William Raveis Real Estate

    5 Mitchell Ln, Deep River, CT 06417
  • 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
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 58 days on the market compared to the national average of 53 days. The median sale price for homes in Deep River, CT over the last 12 months is $455,000, up 8% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$455,000
Median Single Family Sale Price
$493,750
Average Price Per Sq Ft
$322
Number of Homes for Sale
8
Last 12 months Home Sales
48
Months of Supply
2.00
Median List Price
$449,950
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 19 houses for sale, offering an array of options for potential buyers. With houses priced between $319,900 to $2,500,000, there's a range to accomodate every budget. As of November, 2025 the median home price in Deep River is $449,950, while the average sale price is $514,917, offering insights into the local housing market. On average, houses spend 58 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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