Deep River Real Estate

Deep River Real Estate

Welcome to Deep River, Connecticut – a hidden gem nestled in the picturesque Middlesex County. This charming town, steeped in history and natural beauty, offers a unique blend of small-town charm and modern convenience, making it an ideal place to call home.

Deep River is renowned for its stunning landscapes, featuring the serene Connecticut River and lush, rolling hills that invite outdoor enthusiasts to explore. With numerous parks and trails, residents can enjoy hiking, biking, and fishing, all while soaking in the breathtaking views that this region has to offer. The town’s commitment to preserving its natural beauty is evident in its well-maintained public spaces and community gardens.

Rich in history, Deep River boasts a vibrant cultural scene. The town is home to several historical landmarks, including the iconic Deep River Historical Society, which offers a glimpse into the area’s past. The local arts community thrives here, with galleries, theaters, and music festivals that bring residents together and celebrate the town’s creative spirit.

Deep River's close-knit community is one of its most appealing features. With excellent schools, friendly neighbors, and a variety of local businesses, families and individuals alike will find a welcoming atmosphere. The town hosts numerous events throughout the year, from farmers' markets to seasonal festivals, fostering a strong sense of community pride.

Conveniently located just a short drive from larger cities like Middletown and Hartford, Deep River provides easy access to urban amenities while maintaining the tranquility of a suburban lifestyle. Discover the charm of Deep River and find your perfect home in this idyllic Connecticut town!

Newest Listings in Deep River

$579,900
2 Beds ⋅ 2 Baths ⋅ 24202496 MLS
A private New England retreat where character, craftsmanship and nature come together. 2-3 bedroom, 1861 sq. ft. country cape set on 3.75 beautifully landscaped acres in Deep River's Winthrop area, 41 Glen Grove is a truly special property surrounded by stone walls, mature plantings and its own private pond. Inside, wide-board floors, exposed beams, built-ins, a slate entry and two fireplaces-one wood-burning and one gas-give the home warmth and authenticity, while the granite and stainless chef's kitchen brings modern function to its historic-inspired character. Currently two bedrooms, the floor plan offers excellent flexibility with a main-level den and a charming parlor/study adjoining the primary bedroom-ideal for guests, an office, nursery or additional private space. The septic system is sized for a 3-4 bedroom home, offering future possibilities. Stone patios extend the living outdoors, with a hot tub hookup already in place. The former stable barn, complete with stalls and tack room, could return to equestrian use with room for a paddock or become an incredible studio, workshop or hobby space. Two laundry areas, an attached two-car garage with generous storage, generator and two wells-including a separate irrigation well-complete the property. Private, peaceful and wonderfully distinctive, this is the kind of property that feels worlds away while still feeling completely like home.

41 Glen Grove Rd, Deep River
$289,900
3 Beds ⋅ 3 Baths ⋅ 24200726 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. Separate town water and sewer to each home. Ready for your updating! Electric 100 AMPS each.

1721 Winter Ave, Deep River
$635,000
4 Beds ⋅ 3 Baths ⋅ 24200419 MLS
Prominently on 1.5 private, park-like acres, this inviting four-bedroom custom Colonial offers space, comfort and a peaceful country setting just minutes from Deep River Center and Essex Village. Thoughtfully designed and beautifully maintained, the home combines classic New England character with a spacious open floor plan, designed for everyday living. The main level features gleaming hardwood floors, a bright and welcoming living room, formal dining room and a well-appointed coastal kitchen with white cabinetry, granite countertops, stainless-steel appliances and a casual dining area. Sliders lead to the private deck overlook the property's beautiful natural surroundings and is ideal for outdoor entertaining. A separate family room, centered around the fireplace, provides the perfect place to rest and relax. Upstairs, the spacious primary suite includes a private bath and walk-in closet, complemented by three additional generously sized bedrooms and a second full bath. Central air, a full basement and an attached two-car garage add convenience and abundant space for all of your storage needs. Bordered by natural plantings, beautiful rock out-croppings and a variety of stately trees, this property offers easy access to several hiking trails and nature preserves in the area. Lasting memories will be made with friends and family around the charming fire pit. 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
$399,900
3 Beds ⋅ 1 Baths ⋅ 24198403 MLS
Charming antique home. Walk to town and Post Cove. Living Room, Dining Room, and Kitchen on the first floor. 3 Bedrooms and a full bath upstairs. Covered, open front porch, and a deck in the rear. Sloped lot with level yard up top behind the house. Good Parking. 2 Car Detached garage at street level below. House is dated but appears in good condition.

49 Essex St, Deep River
$229,000
2 Beds ⋅ 1 Baths ⋅ 24198175 MLS ⋅ Ridgewood Hills BLDG.
Single level living in updated condo in Deep River! Peaceful location provides serenity, yet close to vibrant town center with everything you need including restaurants, shops, groceries, pharmacy and more! Close to Route 9 for convenience. Why rent when you can own in Deep River?!

77 Scenic View Dr Unit 17, Deep River
$675,000
3 Beds ⋅ 3 Baths ⋅ 24193845 MLS
ONLY 10 HOMES call this neighborhood home. This center hall colonial is set on a wonderful lot. Bordering the rear is open space owned by Deep River Land Trust, affording a bit more privacy to the backyard. One will appreciate the drop zone, ample closets, access to the garage, and both front and rear yards. One of the three full baths is here, too. Spacious rooms are found throughout the house, including a bonus room over the garage. Entertaining is a breeze from the kitchen to the dining areas to the deck and pool. And if the power goes out, the full-house Generac generator will keep the party going. The central air system is non-operational.

21 Sunset Rdg, 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
$429,900
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
$850,000
3 Beds ⋅ 4 Baths ⋅ 24192283 MLS
Modern style abounds in this 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
$289,900
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
$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
Essex Village is a short walk to this one-of-a-kind home, privately set on over three picturesque acres. 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
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