22

Deep River, CT Homes for Sale

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  • 163 Main St, Deep River, CT 06417
    163 Main St, Deep River, CT 06417
    163 Main St, Deep River, CT 06417
    /40

    $985,000

    • 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
  • 8 Route 148, Killingworth, CT 06419
    8 Route 148, Killingworth, CT 06419
    8 Route 148, Killingworth, CT 06419
    /40

    $825,000 Open Sat 11AM - 1PM

    • 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
  • 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

    $1,395,000

    • 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
  • 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
  • 109 Hemlock Dr, Killingworth, CT 06419
    109 Hemlock Dr, Killingworth, CT 06419
    109 Hemlock Dr, Killingworth, CT 06419
    /39

    $649,000

    • 5 Beds
    • 3.5 Baths
    • 2,934 Sq Ft

    109 Hemlock Dr, Killingworth, CT 06419

    Beautiful Hemlock Drive is the setting for this lovely 5 bedroom, 3 1/2 bath Colonial. Enjoy the thoughtfully updated kitchen with ample cabinets and a huge pantry. The Family Room with a wood burning fireplace is accessible from the attached 2 car garage. Host holidays and gatherings in the bright, spacious dining room. Enjoy the convenience of a first floor office with an adjoining den/living

    Maggie Bartels Coldwell Banker Realty

    109 Hemlock Dr, Killingworth, CT 06419
  • 92 Main St Unit 214, Deep River, CT 06417
    92 Main St Unit 214, Deep River, CT 06417
    92 Main St Unit 214, Deep River, CT 06417
    /24

    $259,000

    • 2 Beds
    • 2 Baths
    • 1,122 Sq Ft

    92 Main St Unit 214, Deep River, CT 06417

    Deep River's answer to Manhattan loft living! This 2 bedroom, 2 bath condominium is located in-town so you can walk to shops, library, restaurants and bank. This building was originally a piano factory which was converted to residential condominiums in 1985. Ample off street parking in the rear and the building entrance requires a key to unlock for added security. Once in the foyer it's just a

    Richard Greene Coldwell Banker Realty

    92 Main St Unit 214, Deep River, CT 06417
  • 128 Chestnut Hill Rd, Killingworth, CT 06419
    128 Chestnut Hill Rd, Killingworth, CT 06419
    128 Chestnut Hill Rd, Killingworth, CT 06419
    /40

    $2,800,000

    • 5 Beds
    • 3.5 Baths
    • 5,327 Sq Ft

    128 Chestnut Hill Rd, Killingworth, CT 06419

    Modern Craftsman Countryside Retreat boasting 5 bedrooms, 3.5 bathrooms, an indoor and an outdoor pool, and barn. Discover your private estate in this stunning home; beautifully set on a vast twenty-seven acres in the peaceful countryside. This recently built residence offers pastoral views and a seamless blend of rustic charm and luxurious living; designed for both relaxation and entertaining.

    Scott Penna William Raveis Real Estate

    128 Chestnut Hill Rd, Killingworth, CT 06419
  • 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

    $800,000

    • 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
    /40

    $369,000

    • 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
  • 100 N Tower Hill Rd, Killingworth, CT 06419
    100 N Tower Hill Rd, Killingworth, CT 06419
    100 N Tower Hill Rd, Killingworth, CT 06419
    /20

    $385,000

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

    100 N Tower Hill Rd, Killingworth, CT 06419

    Attention investors, contractors, and dream-home seekers - this is your chance to own a hidden gem with incredible upside potential! This spacious cabin-style home sits on over 3 private acres of natural beauty, offering access to a pond and breathtaking views of a state forest preserve right across the road. Step inside and discover the home's generous footprint, featuring multiple bedrooms,

    Jason Saphire www.HomeZu.com

    100 N Tower Hill Rd, Killingworth, CT 06419
  • 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
  • 331 Route 148, Killingworth, CT 06419
    331 Route 148, Killingworth, CT 06419
    331 Route 148, Killingworth, CT 06419
    /39

    $520,000

    • 3 Beds
    • 1.5 Baths
    • 1,835 Sq Ft

    331 Route 148, Killingworth, CT 06419

    Welcome to this Historic 1,835 sf extended Cape, with 3 good sized bedroom's and 1 1/2 baths, which sits on 3.5 bucolic acres on the corner of Birch Mill Rd. where "old" meets "new". The grounds include a large barn, AND an oversized 2 car garage, a stone patio and level backyard with planting areas, beautiful gardens and forestry. The Reading Room with wide pine floors, is quaint with its

    Eileen Boulay William Pitt Sotheby's Int'l

    331 Route 148, 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

    Exquisite Shingled Traditional European Estate on the Connecticut River. Discover unparalleled elegance and waterfront serenity with this majestic 5,557 square-foot Traditional style residence, perfectly situated on a lush 2.52-acre estate with dock and beach on the CT River. Boasting 5 bedrooms and 5.5 bathrooms, this home is a testament to craftsmanship and sophisticated living. The home's

    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
  • 86 Lynn Rd, Ivoryton, CT 06442
    86 Lynn Rd, Ivoryton, CT 06442
    86 Lynn Rd, Ivoryton, CT 06442
    /40

    $599,000

    • 2 Beds
    • 2.5 Baths
    • 2,484 Sq Ft

    86 Lynn Rd, Ivoryton, CT 06442

    This stunning custom designed shingle style home boasts dynamic features such as cathedral ceilings, a 2-story staircase, skylights, 2.5 acres, the wrap around decks offer plenty of outdoor space to enjoy the private wooded lot. The separate studio/office provides a quiet space for work or creativity. The unique design elements and fabulous location make this home truly special. With a circular

    Maureen Evans William Raveis Real Estate

    86 Lynn Rd, Ivoryton, CT 06442
  • 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 Deep River

Real Estate & Homes for Sale in Deep River, CT

Why Live in Deep River

Deep River is a small New England town on the Connecticut River with just over 1,000 homes, known for its welcoming community atmosphere. The neighborhood offers a variety of housing options, including antique Colonials near downtown and newer raised ranches and Cape Cods farther out, with prices ranging from $250,000 to $650,000 for single-family homes. Condominiums are also available, priced between $100,000 and $275,000. Deep River Elementary and Valley Regional High are highly rated schools, contributing to the area's appeal for families. The town's downtown district, Deep River Center, features local staples like the Whistle Stop Café and the nonprofit Nest Coffee House. High Nine Brewing is a popular spot for socializing. Residents enjoy numerous things to do, such as attending the annual Ancient Deep River Muster Parade, visiting the Deep River Farmers Market, and enjoying summer concerts at the town green. Outdoor enthusiasts can explore Canfield Woods, a 300-acre nature preserve, or visit the Deep River Marina for boating activities. Devitt Field and Plattwood Park offer baseball fields for sports lovers. The town is about 30 miles from New Haven and 35 miles from Hartford, with River Valley Transit providing local transportation services. While the area is generally safer than the national average, potential homebuyers should be aware of the flooding risk due to the town's proximity to the Connecticut River and inquire about flood insurance.
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 $612,155.
How many homes have sold over the last 12 months in Deep River, CT?
72 homes have 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 06457, 06437, 06443, 06360 and 06405.
How much do you need to make to afford a house in Deep River?
The median home price in Deep River is $442,450. If you put a 20% down payment of $88,500 and had a 30-year fixed mortgage with an interest rate of 6.77%, your estimated principal and interest payment would be $2,300 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $99K 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 56 days on the market compared to the national average of 50 days. The median sale price for homes in Deep River, CT over the last 12 months is $453,500, up 7% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$453,500
Median Single Family Sale Price
$493,750
Median 2 Bedroom Sale Price
$210,000
Average Price Per Sq Ft
$304
Number of Homes for Sale
12
Last 12 months Home Sales
72
Months of Supply
2.00
Median List Price
$442,450
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
7%
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