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77 Scenic View Dr Unit 17, Deep River
$210,000
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
141 Cedar Swamp Rd, Deep River
$1,005,000
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
391 Main St Unit 134, 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 with low monthly HOA of $272 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
33 Acorn Rd, Deep River
$250,000
3 Beds ⋅ 1 Baths ⋅ 24208779 MLS
Due to multiple offerings --Highest & Best, Due By: Wednesday 5PM, September 30, 2026 **INVESTOR * CONTRACTOR * HANDYMAN OPPORTUNITY COMING SOON - Welcome to 33 Acorn Road, Deep River- a property with plenty of potential for the buyer ready to roll up their sleeves and bring their vision to life. This is a true handyman/renovation opportunity. The property needs work and updating, but the asking price reflects the condition and the improvements needed, giving the right buyer an opportunity to add value and create a home tailored to their own vision. Whether you're a contractor looking for your next project, an investor seeking a renovation opportunity, or a buyer looking to personalize a property from the ground up, this property is worth a look - it has great bones featuring a lovely big yard, lots of privacy and trees as a backdrop to enjoy you're evenings around the fire pit roasting marshmallows and making family memories.. Situated in a desirable Deep River location and established neighborhood, this property offers the opportunity to renovate, improve, and make it your own. **Bring your ideas, your contractor, and your vision!** Cash purchase or renovation loan may be preferred. Property is being sold in its current condition. AS IS / WHERE AS

33 Acorn Rd, Deep River
49 Essex St, Deep River
$315,000
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
27 Beechwood Dr, Deep River
$451,000
3 Beds ⋅ 2 Baths ⋅ 24208860 MLS
First time offered in over 50 years! Set on over an acre at the end of a cul-de-sac, this three-bedroom, one-and-a-half-bath home offers a wonderful combination of space, privacy, and potential. Step inside the foyer, where the home opens to two levels of living space. Upstairs, you'll find the main living area along with three bedrooms, including a primary bedroom with its own half bath. The lower level features a spacious family room with a fireplace, providing additional room to relax, entertain, or create a flexible living space. One of the home's standout features is the expansive covered deck spanning the back of the house, overlooking a beautiful backyard with plenty of room to enjoy the outdoors. Additional features include a dedicated laundry room, ample storage, and a one-car garage. Lovingly held by the same seller for more than five decades, this home presents a special opportunity to make it your own and begin its next chapter.

27 Beechwood Dr, Deep River
58 Union St, 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
41 Glen Grove Rd, Deep River
$610,000
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
16 Jones Ln, Deep River
$378,000
2 Beds ⋅ 1 Baths ⋅ 24201808 MLS
Great Deep River opportunity in the most charming neighborhood 1/2 mile to downtown, little over a mile to Deep River Landing and approx 2-minute drive to Route 9 access! Storybook 1900's home adorned with absolutely beautiful plantings, trees and shrubbery with something always blooming during growing seasons! Energy conscious home is packed with value. Rare offering of geothermal combined with solar panels offer no fossil fuel usage needed and most of year monthly cost of $129 for heat, hot water, electricity and central air! Local to area company in Essex installed geothermal and full write-up on how this fabulous system works available upon request. In addition to this, blown in insulation has been added to walls along with extra attic insulation. New roof 2019! Beautiful recent full kitchen renovation w/quartz counters and high-end cabinetry. 8-year-old stone lined hot water heater, some updated appliances, oversized 2 car garage. Spacious sunny rooms! Plenty of room in the secluded lot for barefeet and BBQ's! Don't miss!

16 Jones Ln, Deep River
78 Meadow Woods Rd, Deep River
$845,000
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
29 Union St, Deep River
$745,000
4 Beds ⋅ 3 Baths ⋅ 24196639 MLS
Built Circa 1765 as a home for the village blacksmith Benjamin Handy, this home retains the character, detail, and history of the original house with the addition of an amazing modern rear wing that includes an open floor plan kitchen, dining, and family room -- offering the best of the old and the new. The new addition also includes a spacious pantry/laundry, mudroom, full bath, and access to a side porch that is screened and heated for year-round enjoyment. The remainder of the lower level contains two bedrooms, a powder room, and a living room with the original fireplace now converted to gas. Upstairs has two bedrooms and another full bath. Enhancing this village charmer is a serene, custom-fenced private retreat offering beautiful, low-maintenance landscaping perfect for outdoor entertaining and relaxing. The centerpiece of the outdoor hardscape is a custom-built stone fireplace with wood storage and plenty of room to gather around the fire on chilly evenings. The barn/garage has recently been tastefully remodeled to add a second car garage bay and a heated upstairs loft that could serve as a hobby or workout room, office, or studio. New hardscaping and landscaping have also been added to unify the outbuilding with the exterior of the main house. The secluded rear of the property is a lush greenscape with mature trees and plantings, and offering a view of the waterfall.

29 Union St, Deep River
409 River Rd, Deep River
$3,650,000
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
21 Sunset Rdg, Deep River
$650,000
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
79 River St, Deep River
$380,000
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
13 Platt Ln, Deep River
$475,000
4 Beds ⋅ 2 Baths ⋅ 24173119 MLS
Welcome to 13 Platt Lane in Deep River a charming multi-family home. Built in 1840, this property blends classic New England character with great investment or owner-occupied potential. Conveniently located near downtown shops, restaurants, parks, and the Connecticut River, with access to schools. The property offers a spacious yard with plenty of room to relax, entertain, garden or enjoy outdoor activities.

13 Platt Ln, Deep River
252 River Rd, Deep River
$5,850,000
5 Beds ⋅ 7 Baths ⋅ 24143703 MLS
A WORLD-CLASS PRIVATE ESTATE SET ON 9.31 GATED ACRES. Nestled behind a private gated entry, this extraordinary CT River Valley estate is a rare luxury compound of architectural distinction, solitude, & resort-caliber amenities. Thoughtfully composed across 5 distinct structures, the property blends modern luxury, European influences, & timeless craftsmanship amid curated landscapes, stone pathways, terraces, & over 6,000sf of refined outdoor living space. This is a truly exceptional, once-in-a-lifetime offering. A long winding driveway gradually reveals an exclusive enclave where the outside world fades away. Stucco structures, cedar shake roofs, & copper gutters emerge in sequence, unified by professionally landscaped grounds, irrigation, & exterior lighting that enhances the estate's serene atmosphere. Completely rebuilt in 2012, & finished in 2015, the Main Residence is a masterclass in quality & livability. Rich millwork, custom cabinetry, radiant-heated hardwood floors, transom windows, & skylights define interiors that feel both elegant & inviting. A boutique-style coat room & jewel-box powder room immediately signal the home's uncompromising level of finish. The show-stopping kitchen features high-gloss bespoke cabinetry, nickel hardware, & a sculptural range hood beneath tall silver-leaf detailed ceilings. A substantial Calacatta marble island integrates a 2nd sink, butcher block, & concealed storage. Chef-grade appliances include SubZero, Wolf, & Miele. *CONTINUED*

252 River Rd, Deep River
77 Scenic View Dr Unit 4, Deep River
$230,000
2 Beds ⋅ 2 Baths ⋅ 24185812 MLS ⋅ Ridgewood Hills BLDG.
Welcome to your new home-a spacious townhouse-style condominium nestled in a peaceful wooded setting in desirable Deep River. This 2-bedroom, 1.5-bath home offers over 1,200 square feet of comfortable living space, featuring an open and functional layout, central air, and abundant natural light throughout. Enjoy your morning coffee on the private balcony or relax on the patio overlooking the tranquil wooded backdrop. Conveniently located just minutes from downtown Deep River, local restaurants, shopping, and Route 9, this home offers the perfect balance of privacy and accessibility. Whether you're a first-time homebuyer, downsizing, or looking for a low-maintenance lifestyle, this move-in-ready condo is an opportunity you won't want to miss

77 Scenic View Dr Unit 4, Deep River
497 Winthrop Rd, Deep River
$640,000
4 Baths ⋅ 24094162 MLS
Small strip plaza consisting of 3 retail spaces, two garages(rented separately) a single family ranch with garage/storage (rented separately). all situated on 4 acres. Two of the spaces have longer term leases and the single family is yearly. Two beautiful ponds with picnic tables to enjoy your lunch and watch the beautiful blue heron at their nest in the rear of the property. Property is located on a state road which has a good traffic count per day. Many updates and renovations have been done to the property within the past 6 years. Units all have separated heat, hot water and electric. Come visit.

497 Winthrop Rd, Deep River
92 Main St Unit 107, Deep River
$205,000
1 Beds ⋅ 1 Baths ⋅ 24197364 MLS ⋅ The Piano Works BLDG.
Step into a loft-style townhouse in the historic Piano Works building that blends vintage charm with modern living. With its own private entrance and location in a 4-unit outbuilding, this home offers peace and privacy-no upstairs or downstairs neighbors to worry about! With its impressive 9-foot-plus ceilings and exposed ductwork, this home exudes a chic, industrial vibe. Right outside your door, your assigned parking space awaits, while the main building offers thoughtful amenities like private storage, two shared laundry areas, a fitness center, and a community room with a kitchen. The outdoor spaces are perfect for relaxing or gathering, with landscaped patios, grills, fire pits, and a fenced dog area.

92 Main St Unit 107, Deep River
16 Glen Grove Rd, Deep River
$850,000
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
89 Falls Landing Rd, Deep River
$826,000
4 Beds ⋅ 3 Baths ⋅ 24183620 MLS
Welcome to 89 Falls Landing Road, a beautifully cared-for, one-owner Cape situated on 1.8 acres on a quiet cul-de-sac. The community is conveniently located close to schools and the center of town. Blending comfort, versatility, and privacy, this home is perfectly suited for gathering with family and friends, working from home, or simply enjoying everyday life. Set on a sunny, thoughtfully landscaped lot, the property offers a peaceful retreat while remaining close to shoreline amenities. The open floor plan is ideal for entertaining, with the family room-featuring a wood-burning stove-flowing seamlessly into a newly remodeled, spacious kitchen complete with quartz countertops, built-in banquette seating, and custom lockers leading to the garage. The kitchen and family room open to a deck overlooking the backyard, creating an inviting indoor-outdoor connection. Just off the kitchen, you'll find a convenient laundry room and pantry. The main-level primary suite offers ease and comfort, featuring a beautifully renovated bath. Upstairs, there are three generously sized bedrooms, a spacious loft area, and a full bath. Above the attached two-car garage, a large finished room provides flexible space for a family room, guest retreat, or home office. The finished basement adds even more living space, including a recreation room, an additional gathering area, and a separate office or guest space. A sliding glass door leads out to a beautiful stone patio, garden, and expansive lawn.

89 Falls Landing Rd, Deep River
72 Winter Ave, Deep River
$320,000
3 Beds ⋅ 3 Baths ⋅ 24194515 MLS
Per seller request, HIGHEST & BEST offers DUE TUESDAY 8/4 at 1PM. 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
365 Winthrop Rd, Deep River
$568,000
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
92 Main St Unit 405, Deep River
$263,000
2 Beds ⋅ 2 Baths ⋅ 24186149 MLS ⋅ The Piano Works BLDG.
Welcome to Unit 405 at the historic Piano Works building in Deep River. This well-maintained 2-bedroom, 2-bath condominium offers spacious living, high ceilings, and timeless character in one of the area's most unique residential communities. Residents enjoy access to a fitness center and community room, along with convenient proximity to downtown shops, restaurants, marinas, and the Connecticut River. Experience low-maintenance living and historic charm in the town proudly known as the home of the Fife & Drum Corps.

92 Main St Unit 405, Deep River
15 Cloverdale Cir, Deep River
$480,000
3 Beds ⋅ 1 Baths ⋅ 24179845 MLS
Welcome to 15 Cloverdale Circle, a spacious and versatile home set on a quiet corner lot in one of Deep River's most desirable neighborhoods. Offering 3 bedrooms, 3 full bathrooms with limitless flexibility this property is ideal for single-level living, multi-generational households, guests, or those seeking additional living and work-from-home space. The main level features a large open kitchen with dining area, generous living spaces, hardwood floors, a wood burning fireplace, two full bathrooms, and direct access to an expansive two-level deck perfect for entertaining, outdoor dining, or relaxing in the peaceful setting. The recently remodeled walk-out lower level offers exceptional flexibility with both interior and private exterior access. This inviting space includes a large living area, kitchenette with dining space, a separate room used as a bedroom, and a beautifully updated full bathroom, creating an ideal setup for extended family, guests, recreation, or a home office. Adding to the property's unique character, the historic Essex Steam Train travels through the area, offering a charming connection to one of Connecticut's most beloved attractions. Walk to Deep River Center just a mile away, 2.5 miles to Chester and only 6 miles to Essex! You'll enjoy easy access to award-winning restaurants, boutique shopping, galleries, marinas, farmers markets, & year-round community events. Beautifully maintained & updated, newer roof, siding, public sewer & water!

15 Cloverdale Cir, Deep River
56 Shailer Pond Rd, Deep River
$730,000
3 Beds ⋅ 3 Baths ⋅ 24177265 MLS
Nestled in one of Deep River's most coveted neighborhoods, this sophisticated Colonial offers the perfect balance of timeless character, privacy, and flexible living space. Featuring 3 spacious bedrooms and a bonus room on every level, the home's versatile floor plan can easily accommodate a home office, guest suite, hobby room, or potential in-law arrangement. Start your day on the relaxing back porch, host gatherings on the sun-drenched deck, and enjoy the beautifully maintained grounds that showcase exceptional pride of ownership. Bordering state forest, the property provides a rare sense of seclusion and natural beauty while remaining part of a desirable community within an excellent school district. Residents enjoy HOA access to two waterfront locations-one on Shailer Pond and another on Cedar Swamp Road-offering opportunities for recreation and outdoor enjoyment. There is also trail access at the adjoining street to Cockaponset State Forest. Combining comfort, functionality, and outstanding curb appeal, this inviting home is a wonderful opportunity to enjoy all that Deep River has to offer with easy access to i95 and Route 9. Flexible living, scenic surroundings, and a premier location make this property truly special.

56 Shailer Pond Rd, Deep River
391 Main St Unit 308, Deep River
$245,000
2 Beds ⋅ 2 Baths ⋅ 24182590 MLS ⋅ Georgetown Woods BLDG.
Welcome to Unit 308 at Georgetown Woods. This 2 bedroom unit has many upgrades. The first floor features an updated kitchen w/butcher block counters, newer cabinet doors, new refrigerator and large pantry. The living room has a brick hearth & chimney that used to have a working wood stove. The Anderson Thermopane slider opens to the 9'x17' patio, which gives you a private spot to enjoy the outdoors. There is a remodeled half bath on this floor too. The upstairs is home to a remodeled primary bedroom w/hardwood floors and lots of closet space. The spacious second bedroom has a large walk-in closet the current owner is using as an office. The full bath on this floor can be accessed directly from the primary bedroom or the hallway. It is spacious and has newer flooring, vanity and 5ft. walk-in shower. This unit is energy efficient and has thermopane windows & a front storm door. Other upgrades include a 100-amp electric panel and professionally installed laminate floors throughout the first floor. A quick trip into the village center of Deep River for shops, groceries, pharmacy and restaurants or to the boat launch on the CT River, this complex is just a short drive to Rte. 9 making commuting a breeze. Nature lovers can access the 300-acre Canfield Woods Nature Preserve with a 3.7-mile walking trail. The HOA dues provide ground maintenance, snow removal, garbage pickup and professional management. Live a carefree lifestyle in this move in ready unit

391 Main St Unit 308, Deep River
12 Maritone Ln, Deep River
$687,500
3 Beds ⋅ 3 Baths ⋅ 24157763 MLS
Offered for the first time by its original owner, this turn-key, one-level home at 12 Maritone Lane offers total peace of mind, complete with A BRAND-NEW ROOF, central A/C, and a whole-house backup generator. The bright and inviting floor plan features a spacious eat-in kitchen with sliding glass doors to a deck (with a retractable awning) and a welcoming living room centered by a floor-to-ceiling fireplace. The layout includes three comfortable bedrooms, highlighted by a private primary suite with an oversized walk-in closet. Another key feature is the massive walk-up attic, which currently offers incredible storage and endless potential for future expansion, such as a bonus suite or home office. The exterior is a true sanctuary, featuring a beautifully private, easy-care yard. Ample parking is provided by a garage and a stone driveway perfect for a boat, trailer, or extra vehicle. Situated atop the lane in a peaceful setting, the location offers ultimate privacy and picturesque views of the Connecticut River when walking the neighborhood. This is a rare opportunity for a meticulously maintained home in a premium location.

12 Maritone Ln, Deep River
8 Prospect Hl, Deep River
$345,000
2 Beds ⋅ 1 Baths ⋅ 24182196 MLS
Tucked away on a private .41-acre lot just a short walk from the heart of historic Deep River, this adorable 2-bedroom, 1-bath ranch offers charm, convenience, and endless potential. Built in 1957 and featuring 912 square feet of comfortable one-floor living, this home is the perfect opportunity for first-time buyers, downsizers, investors, or anyone looking to create their own vision. Inside, you'll find a functional layout ready for your personal updates and design ideas-an open canvas waiting for your special touches. Recent improvements include a new roof and new mechanicals, providing peace of mind and a solid foundation for future enhancements. A detached 2-car garage with workshop space offers plenty of room for vehicles, hobbies, storage, or projects. Enjoy the best of both worlds with easy access to shopping, dining, schools, and major routes while returning home to your own quiet hideaway. Whether you're looking for a starter home, a weekend retreat, or an investment opportunity, this charming ranch is full of possibilities and ready for its next chapter.

8 Prospect Hl, Deep River
15 Grove St, Deep River
$415,000
4 Beds ⋅ 2 Baths ⋅ 24173578 MLS
Discover the charm of Deep River! Situated on a quiet cul-de-sac, this well-maintained 3-bedroom, 1.5-bath home features comfortable living, flexible space, and beautiful outdoor surroundings on .49 acres. A welcoming foyer greets you upon entry and leads to a well-planned interior filled with warmth and versatility. Just off the living room, the sun-drenched three-season porch provides the perfect retreat for relaxing, enjoying nature, or growing plants with its abundant natural light. The centerpiece of the kitchen is a spacious center island, featuring a durable countertop and classic beadboard paneling that adds a touch of cottage charm. With ample storage beneath, the island serves as both a practical workspace for meal preparation and a gathering spot for casual conversations. The open layout seamlessly connects the kitchen to the dining area, making it ideal for entertaining and everyday living. The finished lower level adds valuable living space and features a dedicated home office along with plenty of room for a media or theater area, playroom, gym, or additional entertaining space. Outside, the manicured yard showcases lovely garden areas, open green space, and a peaceful backyard setting ideal for quiet enjoyment or gatherings with family and friends. This home offers the charm of small-town living with convenient access to local shops, restaurants, marinas, and the scenic Connecticut River Valley.

15 Grove St, Deep River

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