Deep River Real Estate

Welcome to Deep River, Connecticut – a hidden gem nestled in the heart of Middlesex County. Known for its picturesque landscapes and tight-knit community, Deep River offers a unique blend of small-town charm and vibrant local culture. With a population that embraces its rich history and natural beauty, this quaint town is an ideal place for families, retirees, and anyone looking to escape the hustle and bustle of city life.

Deep River is beautifully situated along the Connecticut River, providing residents with stunning waterfront views and ample opportunities for outdoor recreation. From hiking and biking along scenic trails to boating and fishing on the river, nature enthusiasts will find plenty to love about this serene environment. The town is also home to several parks and recreational facilities, ensuring that there’s always something to do for residents of all ages.

The downtown area boasts a delightful mix of local shops, restaurants, and cultural attractions. Whether you’re indulging in a delicious meal at a family-owned eatery or exploring the unique boutiques that line the streets, Deep River’s vibrant community spirit is palpable. Additionally, the town hosts various events throughout the year, fostering connections among neighbors and celebrating the local culture.

Education is a cornerstone of Deep River, with access to top-notch schools that prioritize student success and community involvement. With its friendly atmosphere, strong sense of community, and beautiful surroundings, Deep River is not just a place to live – it’s a place to call home. Come explore the charm of Deep River and discover why so many are proud to be a part of this wonderful town!

Newest Listings in Deep River

$259,000

3 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ COMING SOON Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

$399,900

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 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

$2,200,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24185654 MLS

134 Meadow Woods Road is a rare Connecticut Shoreline estate property offering a custom Saltbox-style home on approximately 30 private acres in one of Deep River's most desirable locations. This 3-bedroom, 2-bath country home features approximately 1,591 square feet, hardwood and wide-plank pine flooring, a cathedral ceiling, patio, and unfinished basement. Surrounded by mature woodlands, historic stone walls, and gently rolling topography, the property offers exceptional privacy, natural beauty, and flexibility. The existing residence provides immediate value as a primary home, weekend retreat, guest house, caretaker residence, rental property, or multi-generational living opportunity. Expansive acreage creates space for outdoor recreation, hiking trails, gardening, equestrian pursuits, or the creation of a private estate, family compound, or legacy property. In addition to the existing home, the property may offer future residential subdivision potential for approximately 5-7 lots, creating a compelling investment property and residential development opportunity. Builders, developers, and investors will appreciate the combination of buildable acreage, road frontage, and potential estate sized homesites. Select future building locations may offer seasonal Connecticut River views depending on elevation and home placement. Located near Marinas, Connecticut River, Essex Village, Chester Village. Unique property combines a custom home with acreage and development potential

134 Meadow Woods Rd, Deep River

$2,200,000

ACTIVE Status ⋅ 24185650 MLS

Rare opportunity to acquire approximately 30 acres in one of Deep River's most desirable locations. This exceptional property presents a unique residential development opportunity combining privacy, natural beauty, existing improvements, and future potential. The property includes an existing Saltbox style residence and offers subdivision potential for approximately 5-7 residential lots, subject to approvals and diligence. Featuring gently rolling topography, mature woodlands, historic stone walls, and expansive acreage, this remarkable parcel is ideal for builders, developers, investors, or buyers seeking a private compound, family compound, multi generational compound, or legacy property. The land is well suited for luxury homesites, estate sized lots, custom homes, a boutique luxury subdivision, or a private estate. Select building locations may offer seasonal Connecticut River views depending on home placement and elevation. The existing Saltbox home provides immediate utility as a residence, guest house, rental property, caretaker's home, or staging area during future development. Minutes from Essex and Chester Village, the property offers convenient access to the Connecticut River, Safe Harbor Marinas, yacht clubs, the Essex Steam Train, shopping, dining, cultural attractions, and the Route 9 commuter corridor while maintaining a secluded setting. A rare Connecticut Shoreline offering combining 30 acres, residential subdivision potential, luxury homesites.

134 Meadow Woods Rd, Deep River

$650,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24185333 MLS

Nestled in the charming town of Deep River, between the villages of Essex and Chester, this beautiful Colonial offers the perfect blend of classic character and modern updates. Featuring 4 bedrooms, 2 full baths and 2 half baths, this spacious home is designed for comfortable living and entertaining. Enter through the welcoming foyer, where the dining room sits to the left, while French doors open to the formal living room on the right. The living room features hardwood floors and a cozy gas fireplace, providing a warm and inviting atmosphere. The kitchen was updated in 2023 with the finest material including a 5 burner gas range with an additional island oven, quartz and butcher block countertops and a casual eat-in area with sliders leading to the rear deck. To the right of the kitchen area is a convenient laundry closet along with a half bath and mudroom area adding to the home's functionality. Just off the kitchen is a spacious family room with its own private entrance, large windows bringing in natural light and a half bath offering endless possibilities for home office, in-home business, guest space or recreation room. The second floor features a generous primary suite complete with a walk-in closet and private bath with jacuzzi tub and separate shower. Three additional bedrooms and a full bath provide ample space for family and guests. Split-unit systems provide additional heating and cooling on both levels, offering year-round comfort and energy efficiency.

38 Main St, Deep River

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