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

$3,625,000

5 Beds ⋅ 5 Baths ⋅ 24191233 MLS

Tucked away from the road and set above the CT river on over three acres, this amazing waterfront home is also a secluded personal resort, complete with a pool, spa, and private beach. Designed to showcase river views from every vantage point, the home features high ceilings, floor to ceiling windows, and an expansive open-concept floor plan that brings in an abundance of natural light. A living room with a fireplace, formal dining area, and family room all lead out to a large deck, which offers plenty of room for outdoor entertaining or just admiring the scenic waterfront setting. A well-appointed chef's kitchen with a center island and plenty of storage space faces the family room. A first- floor primary bedroom offers an office/sitting area with another fireplace, a generous ensuite bathroom with both a soaking tub and walk-in shower. A spacious laundry/mud room leads from the kitchen to the three-car garage. A sunroom overlooks the pool deck, which includes a gunite in-ground pool, a large patio area, and a fantastic outdoor kitchen with a built-in grill and bar area perfect for al fresco dining. The second-floor landing is open to the first floor below, and has two bedrooms both with ensuite bathrooms, and sitting area. The finished walk-out lower level leads to another patio area overlooking the private beach. A large family room, a full kitchen, two more bedrooms and a full bathroom complete the lower floor, offering plenty of room for visitors.

409 River Rd, Deep River

$449,900

2 Beds ⋅ 1 Baths ⋅ 24179608 MLS

Welcome to 58 Union Street in the heart of charming Deep River! Just moments from the vibrant downtown, this beautifully updated home offers the perfect blend of character, comfort, and modern efficiency. Inside, you'll find hardwood floors, timeless architectural charm, and a thoughtfully renovated interior featuring a remodeled kitchen with all-new stainless-steel appliances, an updated bathroom with new fixtures, plumbing and a newly created first-floor laundry room converted from the former utility space for added convenience. The electric was upgraded to 200 amps & new energy-efficient mini-split systems provide year-round heating and cooling, while solar panels help keep utility costs low. Step outside to enjoy the newly installed backyard patio-an inviting space for relaxing or entertaining. Garden enthusiasts will appreciate the unique outdoor sink with both hot and cold water, making gardening projects and outdoor cleanup easier than ever. Located just a short stroll from the center of town, you'll love the convenience of Deep River's charming shops, restaurants, parks, and community events. Experience the best of small-town living, including the nationally recognized annual Deep River Ancient Muster, one of the area's most celebrated traditions. This move-in-ready home is the perfect opportunity to enjoy comfort, efficiency, and an unbeatable in-town location. A great condo alternative or second home.

58 Union St, Deep River

$259,000

3 Beds ⋅ 3 Baths ⋅ 24194515 MLS

This one owner home is tucked away on a private street in the heart of Deep River. Opportunity abounds with a large kitchen, dining room and living room... ready for you to make the design decisions suiting your needs and style. With two bedrooms on the second floor and an additional third bedroom on the first floor you'll feel instantly at home. The lower level is partially finished and is currently used as an apartment. Lovely newer deck with stairs and a whole house generator. Easy access to the many shops and restaurants and experience the welcoming community of Deep River. This home is sold AS-IS. Seller to make no repairs. Buyer to do their own due diligence.

72 Winter Ave, Deep River

$850,000

3 Beds ⋅ 4 Baths ⋅ 24192283 MLS

Contemporary 3-bedroom, 2 full bath, 2 half bath home offering exceptional flexibility, character, and entertaining space. The open-concept main level features vaulted ceilings, dramatic architectural lines, and seamless flow between the kitchen, dining, and living areas. A striking firebox anchors the living room, while the four-season sunroom opens through French doors to a private tiered deck complete with a custom stone fireplace-perfect for outdoor gatherings year-round. The second floor offers two bedrooms plus a spacious primary suite with cathedral ceilings and a truly one-of-a-kind spa bath inspired by a traditional retreat, featuring custom tilework and natural stone accents for a serene, luxurious experience. The finished lower level includes a recreation room and custom-designed bar, creating the ideal space for entertaining. A two-car garage is complemented by a third attached bay leading to a professional woodworking shop with French door access to the beautifully landscaped backyard. Set on picturesque grounds with a gentle stream along the eastern boundary, the property also features mature fruit trees and a productive vegetable garden. Whether you're an entertainer, hobbyist, home-based business owner, or seeking potential in-law living space, this unique property offers endless possibilities and versatile living in a truly special setting.

170 Bushy Hill Rd, Deep River

$325,000

2 Beds ⋅ 2 Baths ⋅ 24192157 MLS

A unique opportunity, 2 Homes on 1 Lot. Plus a barn/garage. First Home has 2 bedrooms and is 1,061 sqft. Second Home has one bedroom and is 350 sqft. Separte town water and sewer to each home. Ready for your updating! Electric 100 AMPS each.

17 & Ave, Deep River

$850,000

4 Beds ⋅ 3 Baths ⋅ 24193089 MLS

An oasis of privacy, peace and elegance awaits you here at one of Deep River's most desirable locations. Spring and summer song birds serenade you from the refurbished deck nestled among mature trees covering 3.21 acres of gently sloping land. As you enter through colorful gardens professionally landscaped for minimal maintenance, you'll be greeted by rich Brazilian Cherry hardwood floors that organically flow from room to room. A spacious open concept will lead you to the hearth of this home, an impressive kitchen that will delight the most discriminating chef. Cherry cabinets, granite counters, center island, SS appliances and a layout that allows for prep, cooking and cleanup to occur simultaneously. Entertaining is a must as your guests greet one another in the storybook family room complete with woodburning fireplace and cathedral ceiling, opening to a 600 sq ft deck where you can enjoy coffee in the morning, wine in the evening, shared meals or the peace of communing with this natural habitat. 4 bedrooms and 2.5 baths include a primary suite with a spa-like jacuzzi bath, dual sinks, shower and a walk in closet sure to accommodate the fashionista in you. 3 additional bedrooms can also be used for office space, a playroom, exercise space or craft room. The hardwood floors gleam in the abundance of sunlight that enters through every corner of this home. And a full basement with meticulously maintained mechanics provides plenty of storage or is ready for your finishing

78 Meadow Woods Rd, Deep River

$1,150,000

8 Beds ⋅ 6 Baths ⋅ 24193614 MLS

VC Property Group is proud to present a rare two-parcel assemblage in Deep River, Connecticut, featuring a newer construction single-family residence, a five-unit mixed-use building with four residential apartments and one retail unit, and a contiguous 0.30-acre vacant parcel. Located in the highly desirable Lower Connecticut River Valley, the property is just 0.4 miles from Downtown Deep River and approximately 1 mile from Downtown Chester, providing convenient access to acclaimed restaurants, boutique shopping, marinas, and the region's historic village centers. Deep River continues to benefit from strong residential demand driven by limited housing inventory and spillover from neighboring Chester and Essex. The assemblage offers immediate cash flow with meaningful long-term upside, including the potential for a municipal lot line adjustment to combine the vacant parcel with the single-family residence, creating a premium residential asset, or to retain the parcel for future single-family development. Combining stabilized income, intrinsic residential value, and embedded development optionality, this offering presents a compelling investment opportunity in one of Connecticut's most desirable river communities.

87 Main St, Deep River

$1,065,000

3 Beds ⋅ 2 Baths ⋅ 24192002 MLS

Privately set on over three picturesque acres in Deep River, just moments from the Essex town line, this extraordinary custom home is the result of an exceptional architectural transformation, blending timeless New England character with thoughtful, high-end design. Enjoy a peaceful, private setting while being just minutes from the charming village centers of Deep River and Essex, with their acclaimed restaurants, boutique shops, marinas, yacht clubs, the Connecticut River Museum, and the historic Griswold Inn. A comprehensive redesign of the home's exterior was completed by renowned architect Christopher Arelt, featuring all-new windows, structural insulated panels for enhanced energy efficiency, cedar shingle siding, copper gutters, Azek trim, a 4-zone heating system, an expansive Ipe deck and stairs, a bluestone patio, and a private outdoor shower. A brand-new well, drilled in May, and a whole-house generator powered by a 500-gallon underground propane tank provide year-round comfort and peace of mind. The home's showpiece is the spectacular four-season sunroom. This breathtaking space features a coffered beadboard ceiling, rich Brazilian cherry flooring, walls of windows, a wood-burning stove, custom built-in seating, and French doors opening onto the expansive Ipe deck, creating an extraordinary setting for year-round living and entertaining.

106 Meadow Woods Rd, Deep River

$3,950,000

5 Beds ⋅ 6 Baths ⋅ 24192020 MLS

Here is your opportunity to own an extraordinary Connecticut River waterfront estate complete with a deep-water dock! This exceptional 5 bedroom, 5.5 bath residence offers unparalleled privacy and stunning panaromic views across protected conservation land, creating a setting of remarkable beauty and tranquility. Thoughtfully designed to embrace its spectacular surroundings, every room is filled with natural light and captures river views, seamlessly blending the ever-changing beauty of the water with miles of pristine, undeveloped landscape. Whether watching boats glide along the river, bald eagles and ospreys soar overhead, or vibrant sunsets reflect across the water, the connection to nature is simply unrivaled. The luxurious primary suite is a private sanctuary, perfectly positioned to showcase the breathtaking riverfront setting and spectacular sunset views. Inside, three fireplaces create warmth and ambiance, offering intimate gathering spaces for cozy evenings and seasonal get-togethers. This unique Deep River property is conveniently located to Essex Village, which is recognized as one of America's "Best Small Towns" where one can enjoy boutique shopping, restaurants, marinas and quintessential New England charm, all while returning to the peace and privacy of your own waterfront retreat. This stunning property is situated two hours from Boston and New York City, and offers convenient access to airports in New haven, Hartford and Providence.

323 River Rd, Deep River

$205,000

1 Beds ⋅ 1 Baths ⋅ 24192095 MLS ⋅ Georgetown Woods BLDG.

Welcome to one of Deep River's hidden treasures! Ideally located in the heart of the beautiful Connecticut River Valley, this inviting condominium offers comfortable, low-maintenance living in a well-maintained 50-unit community with easy access to Routes 9 and I-95.Enjoy the convenience of nearby Main Street, where you'll find a grocery store, liquor store, charming shops, restaurants, marinas, and yacht clubs just minutes away. Freshly painted throughout, this upper level ranch unit is light-filled and features recently replaced living room flooring, a new stainless refrigerator, oven/range, and attractive new carpeting in the bedroom, making it truly move-in ready. The laundry and storage area are located on the lower level. The property includes one assigned parking space plus ample visitor parking. The HOA covers trash removal, lawn maintenance, and snow removal, allowing you to enjoy carefree living year-round. Whether you're looking for a full-time residence, a weekend getaway, or an investment in one of Connecticut's most picturesque Connecticut River towns, this condo is an outstanding opportunity. Complex borders Canfield Woods Nature Preserve with walking trails. Just a few miles from the historic villages of Essex and Old Saybrook, you will enjoy easy access to boating, beaches, dining, shopping, and all the charm of the Connecticut shoreline. You'll love calling Deep River home!

391 Main St Unit 134, Deep River

$475,000

3 Beds ⋅ 2 Baths ⋅ 24189405 MLS

Welcome to 365 Winthrop Road in Deep River, where historic charm meets thoughtful updates. This beautifully maintained 3-bedroom, 2-bathroom home offers timeless character alongside the conveniences of modern living. The spacious main level features a large kitchen, formal dining room, inviting living room, cozy den, and a stunning great room with French doors leading to the backyard, perfect for entertaining or everyday living. Upstairs, you'll find a convenient laundry room, two bedrooms and a generous primary suite filled with natural light, featuring cathedral ceilings, exposed post-and-beam construction, ample closet space, and an en suite bathroom. Step outside to enjoy a picturesque setting with beautiful stonework, mature gardens, and a charming gazebo. A storage shed and a separate workshop with electricity and heating/cooling provide endless possibilities for hobbies, projects, or additional workspace. Recent improvements include hot water heater (December 2025) a new roof and well pump (April 2026). Don't miss this unique opportunity to own a home that seamlessly blends historic character and exceptional outdoor living in Deep River.

365 Winthrop Rd, Deep River

$399,900

2 Beds ⋅ 1 Baths ⋅ 24179607 MLS

Move right into this Deep River home just moments from the Connecticut River and the charming village and town center. Since purchasing the property, the current owner has completed numerous valuable improvements, including a brand-new roof, new furnace, new oil tank, a tastefully remodeled kitchen, and an updated full bathroom. The main level offers inviting living spaces that blend character and functionality. The living room on first floor is presently used as a bedroom. The laundry is conveniently located off the eat in kitchen and there is a large pantry for storage. The finished upper-level features hardwood floors and provides exceptional flexible living space, while also offering exciting potential for future expansion to create additional bedrooms, a spacious primary suite, home office, or craft room. Additional highlights include updated 200-amp electrical service, and the home is generator-ready, providing added convenience and peace of mind. With public water and public sewer, the property offers both ease of maintenance and flexibility for future growth. Ideally located just minutes from downtown Deep River, you'll enjoy easy access to local restaurants, unique shops, marinas, parks, and the scenic Connecticut River. Whether you're searching for your first home, looking to downsize, or seeking a property with room to grow, this well-maintained home offers the perfect blend of thoughtful updates, future possibilities, and a highly desirable location.

79 River St, Deep River

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