Deep River Homes for Sale

Welcome to Deep River, Connecticut – a hidden gem nestled in the heart of Middlesex County. This charming town, steeped in history and natural beauty, offers a perfect blend of small-town charm and modern conveniences. Known for its picturesque landscapes, Deep River is bordered by the scenic Connecticut River, providing residents with breathtaking views and ample opportunities for outdoor activities such as hiking, boating, and fishing.

Deep River is not just about stunning scenery; it’s a community that thrives on connection and camaraderie. With a vibrant downtown area filled with unique shops, delightful eateries, and local art galleries, you’ll find plenty to explore. The town also hosts a variety of events throughout the year, from farmers' markets to seasonal festivals, making it easy to engage with neighbors and create lasting memories.

For those considering a move, Deep River offers an array of homes for sale that cater to various lifestyles and budgets. Whether you’re looking for a cozy cottage, a charming colonial, or a spacious family home, the real estate options here are as diverse as the community itself. Many properties boast lovely yards, modern amenities, and proximity to local schools and parks, making it an ideal place for families and individuals alike.

Living in Deep River means enjoying a tranquil lifestyle while being just a short drive away from larger cities like Middletown and Old Saybrook. With its rich history, community spirit, and beautiful homes for sale, Deep River is not just a place to live, but a place to call home. Come discover the warmth and charm of Deep River – your dream home awaits!

Newest Deep River Homes for Sale

$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

$1,065,000

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

$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

$2,200,000

3 Beds ⋅ 2 Baths ⋅ 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

$650,000

4 Beds ⋅ 4 Baths ⋅ 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

$849,900

4 Beds ⋅ 3 Baths ⋅ 24182027 MLS

16 Glen Grove Road....a stunning custom built 2023 Colonial privately set on 4.53 acres in desirable Deep River. Tucked well off the road and surrounded by beautiful stone walls, this property offers exceptional privacy and endless possibilities to enjoy the outdoors, from garden areas & gorgeous rock walls, to creating your own walking trails throughout the wooded landscape. Inside, you'll find approximately 2,782 square feet of thoughtfully designed living space. The bright, open kitchen is the heart of the home, featuring a center island, gorgeous Narragansett green cabinetry, elegant gold fixtures, and seamless flow into the spacious family room with a fireplace and sliders leading to the rear deck. A formal dining room, additional living room, and convenient half bath complete the main level, offering flexible spaces for both everyday living and entertaining. Upstairs, the primary suite features a spacious walk-in closet and private ensuite bath. Three additional bedrooms and a full bath in the hallway provide plenty of room for family, guests, or home office needs. This home offers the benefits of newer construction along with an energy-efficient heat pump system providing both heating and cooling. Move right in and enjoy modern comfort, privacy, and room to grow.

16 Glen Grove Rd, Deep River

$659,900

4 Beds ⋅ 3 Baths ⋅ 24170783 MLS

Good design is all about the details and this well maintained custom Colonial is just what you have been looking for in the perfect shoreline home. Recently updated, the current owner's signature style has magically taken this charming home from ordinary to extraordinary with her colorful design. From the warm and welcoming entrance, to the well-appointed kitchen or the cozy family room centered around the fireplace, this home offers a lifestyle that embraces quality and comfort. Ideal for entertaining and special occasions, the formal living room and dining room offer guests the perfect balance of relaxed and refined. Upstairs you'll find the primary suite with a walk-in-closet and private bathroom, along with three lovely guest bedrooms with a shared bath. A spacious two-car attached garage offers extra storage and is perfect for all your gardening needs. Enjoy abundant wildlife while savoring the sunshine from your own private deck over-looking park-like grounds; lasting memories will be made with friends and family around a charming fire pit. Prominently set on 1.5 acres, this special home is bordered natural plantings, beautiful rock out-croppings and a variety of stately trees that adorn the property. Located close to Essex Village and Deep River Center this property also offers easy access to several hiking trails and nature preserves in the area. Whether you are looking for a full-time residence or the ideal weekend retreat it's the perfect place to call home.

73 Long Hill Rd, Deep River

$1,199,999

9 Beds ⋅ 9 Baths ⋅ 24179935 MLS

Quintessential New England living in the heart of Deep River. This exceptional Antique home was masterfully expanded in 1987, seamlessly doubling its size while capturing the essence of a classic Colonial-offering the space, flow, and functionality for today's living. The home's design celebrates period-inspired architecture including custom-milled woodwork, wide-plank pumpkin pine floors, and carefully selected reproduction details creating warmth and authenticity. Multiple living and dining spaces unfold effortlessly, anchored by six fireplaces, including an impressive 12' natural stone Rumford. With seven spacious bedrooms-each with its own private bath-the home is uniquely suited for multi-generational living, hosting, or continued hospitality use. The third-floor suite offers a private retreat with a wood-burning fireplace, perfect for extended family or guests. A new kitchen addition further enhances flexibility, easily accommodating in-law living or private guest quarters. Curated perennial gardens, a white oak pergola, and a beautifully crafted stone terrace create a setting designed for gathering and relaxation. Enjoy evenings by the fire pit, surrounded by timeless landscape design. This property offers style, comfort and charm all amidst the local shops, restaurants, marinas, and nearby shoreline destinations-all within two hours of both NY and Boston. Previously, an Award-Winning Bed & Breakfast, and currently featuring two Airbnb guest suites with private access.

209 Main St, Deep River

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