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Deep River, CT Homes for Sale

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  • 14 Kenilworth Dr, Killingworth, CT 06419
    14 Kenilworth Dr, Killingworth, CT 06419
    14 Kenilworth Dr, Killingworth, CT 06419
    /32

    $649,900 Open Sat 10AM - 1PM

    • 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 approximately 4000 sq ft of 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

    Agent Photo

    Eric Bergers

    William Raveis Real Estate

    (860) 775-6542

    14 Kenilworth Dr, Killingworth, CT 06419
  • 262 Connecticut 81, Killingworth, CT 06419
    262 Connecticut 81, Killingworth, CT 06419
    262 Connecticut 81, Killingworth, CT 06419
    /11

    $259,900

    • Land
    • 2.66 Acres
    • $97,707 per Acre

    262 Connecticut 81, Killingworth, CT 06419

    Discover the perfect setting to build your dream home on this exceptional 2.66-acre parcel, ideally situated for both privacy and convenience. Tucked away from the road, this lot offers complete seclusion while being just minutes from local amenities and attractions, this property is truly turnkey for those looking to design and construct a custom residence. Over $100,000 has already been

    Agent Photo

    Gene Pica

    RE/MAX Alliance

    (860) 854-3783

    262 Connecticut 81, 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
  • 163 Main St, Deep River, CT 06417
    163 Main St, Deep River, CT 06417
    163 Main St, Deep River, CT 06417
    /40

    $935,000

    • 3 Beds
    • 2 Baths
    • 4,184 Sq Ft

    163 Main St, Deep River, CT 06417

    EXCITING NEWS, ARV has increased to $1.7 MILLION!!! We met with the town's building inspector and fire marshal for an on-site assessment, and they have expressed interest in seeing the 3rd Floor "Penthouse" get developed into rentable living space. The town needs about 30 days from application and submission of site plans to review the addition for approval. Pre-existing zoning regulations have

    Connor Wenchell VC Property Group, LLC

    163 Main St, Deep River, CT 06417
  • 32 Pinewood Trail, Deep River, CT 06417
    32 Pinewood Trail, Deep River, CT 06417
    32 Pinewood Trail, Deep River, CT 06417
    /40

    $869,000

    • 4 Beds
    • 3.5 Baths
    • 3,697 Sq Ft

    32 Pinewood Trail, Deep River, CT 06417

    Set on 3.54 private acres in Winthrop, 32 Pinewood Trail offers a farm-to-table lifestyle with plenty of room for a flourishing vegetable garden, a chicken coop, or simply open space to enjoy the seasons. The home itself is thoughtfully designed for flexibility, featuring an IN-LAW APARTMENT with a separate entrance on the lower level, ideal for extended family, or guests. Large windows fill the

    Erin Borruso William Pitt Sotheby's Int'l

    32 Pinewood Trail, Deep River, CT 06417
  • 275 Route 148, Killingworth, CT 06419
    275 Route 148, Killingworth, CT 06419
    275 Route 148, Killingworth, CT 06419
    /35

    $949,000

    • 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
  • 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

    • 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 Open Sat 12PM - 2PM

    • 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
  • 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
  • 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
  • 464 Roast Meat Hill Rd, Killingworth, CT 06419
    464 Roast Meat Hill Rd, Killingworth, CT 06419
    464 Roast Meat Hill Rd, Killingworth, CT 06419
    /38

    $489,000

    • 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
  • 29 Bridlepath Trail, Killingworth, CT 06419
    29 Bridlepath Trail, Killingworth, CT 06419
    29 Bridlepath Trail, Killingworth, CT 06419
    /13

    $249,900

    • 2 Beds
    • 2 Baths
    • 1,460 Sq Ft

    29 Bridlepath Trail, Killingworth, CT 06419

    Move right into this Active Adult 55+ community in lovely Killingworth. This home is one of the largest available and includes a sunroom, carport and outdoor shed. Featuring a large eat in kitchen with island and breakfast bar, formal dining and living room. Primarly bedroom suite includes a walk in closet and a bath with handicap accessible renovated shower. The community offers a clubhouse with

    Waneta Lenk Carl Guild & Associates

    29 Bridlepath Trail, Killingworth, CT 06419
  • 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
  • 45 Castle Heights, Deep River, CT 06417
    45 Castle Heights, Deep River, CT 06417
    45 Castle Heights, Deep River, CT 06417
    /6

    $50,999

    • Land
    • 0.83 Acre
    • $61,445 per Acre

    45 Castle Heights, Deep River, CT 06417

    Discover this wooded 0.83-acre lot located just minutes from Deep River Landing and all the charm of downtown Deep River. With no HOA restrictions, this property offers flexibility and privacy. A newly installed 300'+ driveway is already in place, and engineering for a 4-bedroom home and septic system is on file-saving you time and money. Enjoy convenient access to shopping, restaurants, and

    Joel Hinckley PLTC, LLC

    45 Castle Heights, Deep River, CT 06417
  • 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
  • 92 Main St Unit 102, Deep River, CT 06417
    92 Main St Unit 102, Deep River, CT 06417
    92 Main St Unit 102, Deep River, CT 06417
    /14

    $179,900

    • Studio
    • 1 Bath
    • 474 Sq Ft

    92 Main St Unit 102, Deep River, CT 06417

    Small Studio Condo in Piano Works. Central Air and High Ceilings. Association Common Room. Gym. Walk to town & CT River.

    Craig Milton Re/Max Valley Shore

    92 Main St Unit 102, Deep River, CT 06417
  • 134 Meadow Woods Rd, Deep River, CT 06417
    134 Meadow Woods Rd, Deep River, CT 06417
    134 Meadow Woods Rd, Deep River, CT 06417
    /16

    $2,000,000

    • Land
    • 30 Acres
    • $66,667 per Acre

    134 Meadow Woods Rd, Deep River, CT 06417

    Incredible development opportunity in Deep River, CT-30 sprawling acres overlooking the scenic Connecticut River. With access from three main roads and the potential for up to 16 approved lots (per town guidance), this property offers a rare chance for an experienced developer to bring a vision to life. A house currently sits on the land and will convey in as-is condition. Whether you're looking

    Nicholas Burrus Santana Realty Group LLC

    134 Meadow Woods 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
  • 156 Main St, Deep River, CT 06417
    156 Main St, Deep River, CT 06417
    156 Main St, Deep River, CT 06417
    /8

    $750,000

    • 2 Baths
    • 5,460 Sq Ft

    156 Main St, Deep River, CT 06417

    This is a rare opportunity to acquire a fully stabilized retail asset in Downtown Deep River. Additional income generation is possible by monetizing 800sqft of unrented commercial space. Inside the past 5 years the owner has replaced the entire roof, upgraded the electrical service and replaced all of the furnaces. Upon leasing up the existing units along with the 800sqft space in the rear of

    Connor Wenchell VC Property Group, LLC

    156 Main St, Deep River, CT 06417
  • 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
  • 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
  • 115 Hemlock Dr, Killingworth, CT 06419
    115 Hemlock Dr, Killingworth, CT 06419
    /2

    $84,900

    • Land
    • 2.70 Acres
    • $31,444 per Acre

    115 Hemlock Dr, Killingworth, CT 06419

    2.7 Acre Lot located on the corner of Hemlock Drive + Route 80. Not far from the circle and Chatfield Hollow. Previously approved for a 2-3 Bedroom home. Test hole data and previous house plan available.

    Craig Milton Re/Max Valley Shore

    115 Hemlock Dr, Killingworth, CT 06419
  • 179 Route 81, Killingworth, CT 06419
    179 Route 81, Killingworth, CT 06419
    179 Route 81, Killingworth, CT 06419
    /13

    $649,999 Coming Soon

    • 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
  • 88 Winthrop Rd, Chester, CT 06412
    88 Winthrop Rd, Chester, CT 06412
    /2

    $985,000

    • Land
    • 34 Acres
    • $28,996 per Acre

    88 Winthrop Rd, Chester, CT 06412

    The wooded 33.97 acre site has extensive open water views with frontage on Winthrop Road (Rt 145) and Butter Jones Road. The property abuts Deep River and Killingworth with convenient access to charming shopping areas. Also, the Chester Airport is within walking distance. A long driveway winds through the spacious, park-like setting, ideal for a planned unit development.

    Peter Walsh Re/Max Valley Shore

    88 Winthrop Rd, Chester, CT 06412
Connecticut Middlesex County Deep River

Real Estate & Homes 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

Frequently Asked Questions

What is the average home price in Deep River, CT?
Homes for sale in Deep River, CT have an average home price of $993,333.
Are home prices dropping in Deep River?
Yes, home prices in Deep River are down 28% in the last 12 months.
How many homes have sold over the last 12 months in Deep River, CT?
1 home has sold in Deep River, CT over the last 12 months.
What are the most popular zip codes in Deep River, CT?
The most popular zip codes in Deep River, CT include 06417, 06442, 06412, 06409 and 06426.
How much do you need to make to afford a house in Deep River?
The median home price in Deep River is $1,017,000. If you put a 20% down payment of $203,400 and had a 30-year fixed mortgage with an interest rate of 6.63%, your estimated principal and interest payment would be $5,210 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $223K a year to afford the median home price in Deep River.
How are the schools in Deep River, CT?
Deep River, CT has highly rated public and private schools. Some of the best schools in Deep River based on Niche Grades are Lyme-Old Lyme High School, Haddam-Killingworth High School and Lyme-Old Lyme Middle School. Browse all the schools in Deep River, CT to learn more.

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%
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