Deep River Real Estate

Deep River Real Estate

Welcome to Deep River, Connecticut—a hidden gem nestled in the heart of Middlesex County. This picturesque town, with its charming New England vibe, boasts a rich history that dates back to the 17th century. Known for its stunning landscapes and vibrant community spirit, Deep River is the perfect blend of small-town charm and modern conveniences.

As you stroll through the quaint streets, you’ll be captivated by the historic architecture and the warm, welcoming atmosphere that defines this close-knit community. Deep River is renowned for its beautiful parks and outdoor recreational opportunities, including the scenic Connecticut River, where residents and visitors alike can enjoy kayaking, fishing, and picnicking along the picturesque banks.

The town is also home to a variety of local shops, restaurants, and cultural attractions that celebrate its artistic heritage. Don’t miss the chance to explore the Deep River Historical Society, where you can delve into the town's storied past or visit one of the many art galleries showcasing local talent.

Families will appreciate the excellent schools and community programs that foster a nurturing environment for children. With its top-notch educational institutions, Deep River is an ideal place to raise a family while enjoying the tranquility of suburban living.

Conveniently located just a short drive from Hartford and New Haven, Deep River offers easy access to urban amenities while maintaining its serene, rural charm. Whether you’re looking to settle down, retire, or find a weekend retreat, Deep River is a delightful place to call home. Come discover the beauty and warmth of this enchanting town!

Newest Listings in Deep River

147 River St, Deep River
$299,900
4 Beds ⋅ 1 Baths ⋅ 24217621 MLS
Antique 4 Bedroom colonial just steps to the CT River and a short walk to town. First floor bedroom and full bath. Small manageble yard. 1 Car Detached oversized garage. Distance from school. Great potential. Generator hook up. Needs work. Ready for your updating!

147 River St, Deep River
206 W Elm St, Deep River
$358,900
2 Beds ⋅ 2 Baths ⋅ 24217309 MLS
Brimming with quintessential New England charm, this cozy yet surprisingly versatile Cape Cod offers a unique blend of character, privacy, and natural beauty. Conveniently located near downtown Deep River, neighboring shoreline communities, and local beaches, the property also offers nearby access to state forest trails leading toward Pine Ledge. Originally built in 1950 and relocated to its current setting during the construction of Route 9 in the 1960s, this distinctive home has a history as interesting as its surroundings. Nestled along a lightly wooded hillside on approximately three-quarters of an acre, the home features two bedrooms, a full bathroom with radiant floor heating, a kitchen, dining area, inviting living room with a wood-burning fireplace, and an additional half bath. A bonus space on the main level showcases sweeping views of Pratt Read Reservoir and the surrounding woodlands, offering a peaceful place to enjoy the beauty of New England's changing seasons. The outdoor spaces are equally distinctive, with a secure poultry enclosure, fish pond, play structure, and open lawn area. An upper-level driveway provides access to a secluded picnic area and a second storage shed. Ample parking is available at the main level, while a separate private driveway below the home leads to an enclosed single-car garage, workspace, storage and interior staircase to the main floor of the home.

206 W Elm St, Deep River
56 Witch Hazel Dr, Deep River
$615,000
4 Beds ⋅ 3 Baths ⋅ 24217205 MLS
Welcome to your peaceful retreat in desirable Witch Hazel estates! This 4 bedroom, 2.5 bathroom home sits on a quiet cul-de-sac and offers a peaceful and tranquil setting. Tastefully updated and beautifully maintained, this home is great for everything from relaxing with your morning coffee to strolling down the sleepy street to entertaining on your expansive deck overlooking your private backyard. Falls River Sanctuary is a stone's throw from your front yard, adding to the serene setting. Extensive updates include a new roof (2021), remodeled kitchen with quartz countertops, updated bathrooms, refinished hardwoods floors throughout the main level, newer covered deck, new bulkhead door, and landscaping.

56 Witch Hazel Dr, Deep River
92 Main St Unit 410, Deep River
$299,500
1 Beds ⋅ 2 Baths ⋅ 24216953 MLS ⋅ The Piano Works BLDG.
Completely & tastefully remodeled end unit located on the 4th floor overlooking the greenery & brook at historic Piano Works. The unit faces westerly & is filled with ambient light through six oversized windows! This bright & airy single level home truly epitomizes the term "Move In Ready"! If you're looking for in-town living, a newly renovated unit & want the closest parking spot in the building, then this is your opportunity to own a magnificent property. Located in the heart of Deep River village, you're just steps to restaurants, boutiques, a membership gym & everything else that this historic community has to offer. The numerous improvements include the completely remodeled kitchen featuring all new appliances, renovated bathrooms, new hardwood flooring & carpeting, custom closets, custom lighting, oversized windows, Hunter Douglas custom window treatments and much, much more! Community amenities include an on-site gym, a common room which is great for events, laundry on two levels & storage on the entry level. This truly is a one of a kind, so don't let it pass you by!

92 Main St Unit 410, Deep River
8 Southworth St, Deep River
$499,000
4 Beds ⋅ 2 Baths ⋅ 24214902 MLS
Imagine strolling along charming brick sidewalks to your favorite downtown restaurant, browsing local gift shops, or enjoying the tradition of Deep River's beloved historic Muster in July right from your front porch! Built in 1918, this well-maintained Colonial offers a wonderful opportunity to experience the character, history, and welcoming community that make this Connecticut river town so special. Step inside this traditional New England home and craftsmanship shines through from the rich wood molding to the spacious foyer with an amazing staircase with classic box newel post. With four bedrooms, 1.5 baths, first floor laundry, expansive kitchen and cozy family room, the home offers an inviting layout filled with timeless character and everyday functionality. The enclosed front porch is a dream come true (BYOR-Bring Your Own Rocker!), while the large side deck provides space for outdoor dining and entertaining. The walk-up attic is a real surprise, measuring 26' x 24' with a high ceiling. One can easily image finishing this space into a primary suite or additional living space! Recent updates include a new boiler, newer roof, and connection to city sewer. If you are looking for a walkable, in-town location, this is it! Recreation fields and a well-equipped playground are across the street while restaurants, gift shops, the public library, the Deep River Historical Society, hiking trails, seasonal farmers' market, supermarket, pharmacy, and 24-hour gym are close by.

8 Southworth St, Deep River
2 Pinewood Trl, Deep River
$685,000
3 Beds ⋅ 4 Baths ⋅ 24212188 MLS
Discover this dramatic modern Cape-style living in this beautifully appointed 3-bedroom, 3-bath home nestled in the scenic Connecticut River Valley. Set on a peaceful dead-end street, with your own private pond, this exceptional property blends contemporary design, inviting spaces, and picturesque natural surroundings. Hardwood floors and a soaring cathedral ceiling create an impressive, open first-floor living area centered around a cozy fireplace. The modern kitchen features stainless steel appliances and flows seamlessly into the main living and entertaining spaces. A desirable first-floor primary suite offers comfort and convenience, while two additional bedrooms on the upper floor provide flexible accommodations for family, guests, or a home office. The fully finished lower level expands your living space with an above-grade walkout, creating the perfect setting for recreation, relaxation, or entertaining. Step outside to enjoy professionally landscaped grounds and the inviting outdoor firepit-ideal for gathering with friends or unwinding under the stars. A two-car garage adds everyday convenience and storage. Enjoy the serenity of a beautiful natural setting and experience the best of Historic Connecticut River Valley!

2 Pinewood Trl, Deep River
92 Main St Unit 205, Deep River
$275,000
2 Beds ⋅ 2 Baths ⋅ 24215276 MLS ⋅ The Piano Works BLDG.
Available at historic Piano Works! This townhouse is one of a few that offers a large private patio for your warm weather enjoyment. Well maintained and updated, this 2 bedroom, 2 full bath unit is ideal for in-town living. Both levels include 9'+ ceilings, exposed brick accent walls, wood beams and wood ceilings. The lower level features updated kitchen cabinets w/stainless steel appliances and tiled backsplash which opens up to the dining & living room areas. Adjacent to the living room you'll find your private patio. Rounding out the lower level you will find a primary bedroom suite with an updated full bath and loft area that is perfect for extra storage. The upper level offers the entry foyer, a 2nd updated full bath, wall of closets for storage, and a 2nd spacious bedroom. This unit also comes with a storage space in the basement. Off the main lobby area you will find an exercise room, community area, and unit mailboxes. Elevators from the lobby/foyer take you to all floors. Shared coin-operated laundry rooms are located on two different levels. Assigned parking is located in the upper lot with plenty of visitor spaces in the upper as well as lower lots. Enjoy all that the Deep River Village has to offer to include restaurants, shopping, gym, library and more! Pets are welcome at this wonderful community!

92 Main St Unit 205, Deep River
42 Laurel Wood Dr, Deep River
$849,000
3 Beds ⋅ 3 Baths ⋅ 24209952 MLS
Welcome to The Grand Gathering at Laurel Wood, where every occasion becomes a special occasion! Beautifully situated on 1.17 landscaped acres at the end of a peaceful Deep River cul-de-sac. This impressive Cape Cod has a huge two story detached three-car garage its incredible and has extra parking on the side for large vehicles / vessels / trailers etc. This home was made for entertaining and has plenty of abundant paved parking for guest. The spectacular great room steals the show with its soaring ceiling, enormous windows, hardwood floors, and generous gathering space. The inviting family room has a handsome brick wall fireplace, another great space. The well-appointed kitchen features abundant cabinetry, stainless steel appliances and eat in area. The formal dining room has french doors to the deck. The main level primary suite is all part of this unique floor plan. Upstairs is a wonderful two bedroom Jack and Jill. To much to list. The basement is huge too. Step outside through through french doors from the great room to the expansive composite deck which offers multiple seating and dining areas, a relaxing hot tub and a walkway to the swimming pool. A super quiet whole-house Kohler generator and a Trane central air-conditioning system are both top notch and provide added comfort and peace of mind. Beautiful lawns, mature trees, and attractive landscaping create a wonderful setting for outdoor enjoyment at The Grand Gathering at Laurel Wood. Explore Deep River today.

42 Laurel Wood Dr, Deep River
216 River Rd, Deep River
$286,000
24214611 MLS
1.63 acres of undeveloped residential land on River Road in Deep River, in the R-80 low-density zone and a short distance from the Connecticut River. A narrow, irregular wedge of about 71,000 square feet, outside the FEMA flood hazard area (Zone X) and within the town's Coastal Boundary. Electric and cable are at the street; there is no public water or sewer, so a private well and an engineer-designed septic system would be required. The parcel is below the R-80 minimum lot area: neither seller nor broker represents that the lot is buildable or that any use is permitted, and buyers should confirm buildability, setbacks and any Gateway Conservation Zone requirements directly with Deep River Planning & Zoning and the Connecticut River Area Health District before purchase. Sold as land; survey, soils and percolation testing are the buyer's responsibility. A seller's land disclosure and a property research summary are available on request.

216 River Rd, Deep River
240 Main St, Deep River
$599,900
3 Beds ⋅ 2 Baths ⋅ 24200740 MLS
Walking distance to Downtown and a brand new roof! Welcome to 240 Main Street. Full of character and warm appeal, this 3-bedroom, 2-full-bath home offers a unique combination of indoor comfort and a prime outdoor setting. Step inside to discover a beautiful, well-appointed kitchen outfitted with a professional Jade stove-perfect for culinary enthusiasts-with views opening out to a beautifully landscaped, private backyard retreat. Built-ins and original details continue throughout the entire home, while thoughtful updates maximize the use of living space. With lots of flex space in the barn, the first floor hosts amazing space for a gym, second office, hobby room or a billiard room. Upstairs, a private office provides a quiet work-from-home setup. Outdoors, the peaceful, tree-lined yard includes a charming potting shed and abuts a serene church field for maximum privacy. Positioned right across the street from the local park, playground, and baseball fields, you'll enjoy front-row access to community recreation while maintaining your own private oasis. Schedule your private tour today!

240 Main St, Deep River
73 Long Hill Rd, Deep River
$625,000
4 Beds ⋅ 3 Baths ⋅ 24208355 MLS
Make your appointment to see 73 Long Hill Road, tucked away in the heart of charming Deep River, one of Connecticut's most beloved river towns. This 4-bedroom home offers small-town character combined with unbeatable convenience - historic Essex and Chester town centers are less than 5 minutes away, offering waterfront dining, boutique shopping, art galleries, and a vibrant year-round community. Outdoor enthusiasts will love the nearby walking and nature trails, perfect for morning hikes or peaceful weekend strolls. A wonderful opportunity to enjoy the best of the lower Connecticut River Valley lifestyle!

73 Long Hill Rd, Deep River
103 Bushy Hill Rd, Deep River
$699,900
3 Beds ⋅ 3 Baths ⋅ 24208142 MLS
This Stunning, completely remodeled ranch style home is truly move in ready! With an open concept living area, perfect for entertaining or everyday living. There is pleanty of kitchen space with an island, new cabinets & quartz countertops and new appliances, living room area with gas fireplace and dining space. High ceilings and plenty of window to let in the natural light. On one side of the house you have the Master bedroom with two walk-in closets & private master bath. The Laundry room and half bath. On the other side of the house are two additional bedrooms & a full bath. Enjoy the privacy of your back deck accessable from both the living room and master bedroom. The lot is just over two acres, surrounded by private lightly wooded land. With over 1700 sq ft of living space there is still room for expansion over the attached two car garage. With entrances from both the garage or outside, this space has been started for an in-law apartment. Frame work, electric & plumbing have been started. Additional photos will be added soon.

103 Bushy Hill Rd, Deep River
Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

How much is your home worth?

Get instant property value now!