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

$749,900

4 Beds ⋅ 3 Baths ⋅ 24205311 MLS

Nestled on a private cul-de-sac overlooking Pratt Read Reservoir, this 4-bedroom, 2.5-bath Colonial offers 3,143 square feet of living space, 200 feet of waterfront frontage, updated bathrooms, and a newer HVAC system. The spacious eat-in kitchen with large pantry opens to a welcoming family room with a gas fireplace, while formal living and dining rooms provide flexible space for entertaining, a home office, or den. A dramatic two-story foyer creates a grand first impression. The primary suite offers generous storage with dual walk-in closets, and a bathroom with a soaking tub, and large walk-in shower. Enjoy year-round water views and outdoor recreation right from your backyard. Kayak, canoe, fish, or simply relax on the oversized deck overlooking the reservoir with direct water access. The walkout lower level is filled with natural light and offers endless possibilities for future expansion. Located on a private cul-de-sac near a popular pick-your-own orchard and just minutes from highly rated Valley Regional High School, this exceptional home offers the perfect blend of privacy, nature, and community.

77 Falls Landing Rd, Deep River

$585,000

4 Beds ⋅ 2 Baths ⋅ 24205608 MLS

Generous proportions, versatile living spaces and exceptional outdoor amenities define this beautifully appointed four-bedroom, two-bath split-level ranch. The open-concept kitchen, living and dining areas feature hardwood floors, creating an inviting and connected main living space. A fireplace anchors the living room, while the kitchen features stainless steel appliances, including a Sub-Zero refrigerator/freezer. The expansive family room is enhanced by exposed beams and opens directly to a covered patio overlooking the private backyard. Additional rooms provide outstanding flexibility for home offices, a den, fitness room, playroom or other uses. An impressive multi-level deck extends the living space outdoors, offering a beautiful setting for entertaining and relaxing. Set on 1.2 private acres, the property also features a three-car garage with abundant parking and storage. Ideally positioned in an established neighborhood near the Connecticut River, with downtown Deep River and Essex just minutes away, this property offers a wonderful balance of privacy, convenience and quintessential Connecticut River Valley living.

24 Long Hill Rd, Deep River

$999,900

4 Beds ⋅ 4 Baths ⋅ 24205606 MLS

Set on nearly six beautifully landscaped acres, this distinctive four-bedroom, three-and-a-half-bath estate blends timeless character with thoughtfully designed living spaces. A welcoming foyer with brick flooring sets the tone, with custom details throughout including wide-board floors, exposed beams, french doors, detailed millwork and four fireplaces. The kitchen is anchored by an impressive oversized fireplace spanning nearly an entire wall, fitted with a gas insert, and a large center island that creates a natural gathering place. The expansive great room features soaring ceilings, custom windows, built-ins, beautiful woodwork and a fireplace, with french doors opening to a covered rear porch overlooking the grounds. The private primary suite encompasses the entire third floor, creating a true retreat. Beyond the home, stone patios and walls create inviting spaces around the saltwater inground pool and pool house. A professionally engineered pond offers swimming and fishing in warmer months and skating in winter. A substantial barn, additional two-car barn/garage and mature landscaping complete this exceptional private estate.

141 Cedar Swamp 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

$359,900

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

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