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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

47 Plains Rd, Deep River
$450,000
3 Beds ⋅ 2 Baths ⋅ 24124474 MLS
Charming Cape Cod home offering desirable first-floor living, nestled on a scenic, spacious, and private lot in a farm like setting. This property features beautifully cleared land perfect for gardening, outdoor entertaining, or simply enjoying the peace and quiet of nature. Step inside to discover a bright, open-concept layout with thoughtful updates including a refreshed kitchen boasting maple cabinets and a large granite island. Flowing seamlessly into the living and dining areas. The main floor offers convenience and charm with 2 bedrooms, a full bath and laundry, while the unique second level boasts a true primary suite complete with a walk-in closet, sitting area, and a roughed-in full bath-ready for your finishing touches. While there's no basement, the large attic space provides plenty of storage, and a detached, distressed barn offers exciting potential. Keep the existing footprint for a rustic look or reimagine it as a garage, workshop, or studio space. Enjoy the tranquility of a private road with direct access to walking trails that lead into the expansive Cockaponset State Forest-ideal for hiking. Don't miss this rare opportunity to own a move-in ready home, with room to improve, in one of Deep River's most peaceful and picturesque settings.

47 Plains Rd, Deep River

120 Warsaw St, Deep River
$441,000
3 Beds ⋅ 2 Baths ⋅ 24142996 MLS
Charming home set on approximately 2.5 acres with a tranquil private pond-an ideal setting for those seeking peace, nature, and outdoor enjoyment. Relax and watch wildlife visit the pond morning or evening. The sunny, spacious living room features gleaming hardwood floors and a fireplace that adds warmth and ambiance during cooler months. A country style kitchen offers a generous dining area, abundant cabinetry, excellent counter space, and charming open shelving-perfect for today's casual lifestyle. The main level includes three spacious bedrooms, all with hardwood floors and ample closet space, along with a full bath to complete the main level. The finished lower level provides wonderful additional living space with a recreation room highlighted by a second fireplace and walkout access to the backyard-ideal for entertaining or simply enjoying the peaceful pond view. A space to use a gaming room, pool or ping pong table for entertainment. This level also includes a half bath, laundry room, and extra storage space. Additional features include a 2car attached garage, breezeway/three season porch, and plenty of outdoor space for gardening, ATV use, or other hobbies. Purchase of this home is subject to a suitable housing contingency.

120 Warsaw St, 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

25 Union St, Deep River
$426,000
3 Beds ⋅ 2 Baths ⋅ 24158671 MLS
***HIGHEST AND BEST HAS TO BE IN AT WEDNESDAY MARCH 25TH AT NOON***Charming antique home, once the church parsonage, rich with history and original character. Many period details remain, including original doors, trim, hardware, and wood floors throughout. The home features three fireplaces (two decorative) that add to its classic New England charm. Set on a lovely yard with mature plantings and conveniently walkable to town, this property offers both character and location. A new roof in 2024 provides added value and peace of mind. The property also includes a two story barn and garage, perfect for storage, hobbies, or workshop space. With its historic charm and great bones, this home is ready for thoughtful updating to make it truly shine.

25 Union St, Deep River

2 Crescent St, Deep River
$421,000
4 Beds ⋅ 2 Baths ⋅ 24134877 MLS
Welcome to this timeless 1907 Victorian, perched high above Crescent Street with enchanting views of Main Street and Keyboard Pond. Just steps from Deep River Village, this home is both tucked away in privacy and close to town, offering a rare blend of historic character and modern comfort. A storybook front porch invites you to enjoy glowing sunsets, while a private back patio with Jacuzzi feels like a secret retreat surrounded by perennial gardens in full bloom. Inside, natural light pours through tall windows, illuminating gracious living spaces with 9-foot ceilings, detailed moldings, and a warm gas fireplace. The main level features a spacious dining room, a light-filled living room with a cozy nook perfect for unwinding with a good book, a country kitchen with abundant storage and a skylight, and a half bath. Upstairs, you'll find four comfortable bedrooms and a full bath, with treetop views from most windows. A walk-up attic awaits your imagination, whether for a studio, playroom, or creative haven. The detached two-car garage provides ample space, and the home itself has been extremely well maintained with thoughtful updates, including a newer roof, cedar shingles, and repainted exterior, all of which enhance the beauty and longevity of this cherished property. Just a short stroll from Deep River's charming Main Street, you'll enjoy boutique shops, cafes, restaurants, the historic library, and the Connecticut River at Deep River Landing. Entrance on Prospect Hill.

2 Crescent St, Deep River

92 Warsaw St, Deep River
$419,588
2 Beds ⋅ 1 Baths ⋅ 24141344 MLS
Open House Cancelled. Delightful 2 bedroom ranch located on approx. 5 acres brimming with character and much future potential! Step inside to beautiful hardwood floors, a generous-sized living room complete with a quirky corner fireplace, sure to be a conversation starter. Natural light pours into the spacious sun room, an ideal spot for morning coffee, afternoon reading or indoor plants that thrive in sunshine. The kitchen, central in location offers good countertop space, great cabinet space, a built-in corner cupboard and a pantry closet. Currently an office, the cozy dining room offers an intimate setting for meals and gatherings with great views of the rear yard. You can't beat the flexibility in the floor plan. Two bedrooms and a full bath complete this level. The lower level is currently an unfinished, walk-out basement that provides a blank canvas for future finished space. Outdoors, you will find a detached two-car garage and lots of parking! And the land .... Do you have ATV's, snowmobiles? Love to garden on a large scale? Need room for your pups? This property is for you! The land on the far side of the garage offers the possibility of adding a future barn, workshop, etc (as town of DR allows) also potential in the large back section of the property for gardens/farming and perfect for outdoor gatherings! Don't miss this opportunity -- a welcoming home on nice acreage with close proximity to town, shopping, schools, commuting routes

92 Warsaw St, 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

69 High St, Deep River
$407,000
2 Beds ⋅ 2 Baths ⋅ 24135035 MLS
Charming New England Colonial in the Heart of Deep River. Welcome to this classic New England Colonial, beautifully situated on High Street across from Deep River Elementary School. This well-maintained home features two bedrooms, with a flexible office space that includes a closet and two windows. This office space offers the possibility to convert into a third bedroom to suit your needs. The interior boasts timeless hardwood floors throughout, adding warmth and character to every room. Just off the kitchen, enjoy the convenience of a main floor laundry and a half bath, perfect for busy daily living. In 2025, a brand-new roof was installed, providing peace of mind and enhancing the home's value. Additionally, the large walk-up attic has been recently reinsulated, offering a generous raw space full of opportunity, ideal for storage, a creative studio, or future expansion. Step outside to a level, open yard surrounded by mature trees and shrubs along the perimeter, providing both privacy and a beautiful natural backdrop. Enjoy a prime location, just minutes away from local favorites such as the Essex Steam Train station, Deep River Ferry stops, and the town's boat launch, all within a short distance of less than 1 mile. This home combines charm, flexibility, and location, ready to welcome its next chapter.

69 High St, Deep River

12 Jones Ln, Deep River
$393,000
2 Beds ⋅ 1 Baths ⋅ 24130074 MLS
Welcome to 12 Jones Lane, a 1,200 sq. ft. Cape Cod in Deep River with recent updates and plenty of charm. The home features a remodeled bathroom, main-level laundry, and a newly enclosed front porch for year-round enjoyment. The yard has been freshly landscaped, and you'll also enjoy a back deck that's perfect for outdoor dining or relaxing. A garage with a breezeway in between adds convenience and extra storage. Driveway was recently paved in The second floor offers the potential to be finished for additional living area, giving you room to grow. Just minutes from the Connecticut River, you'll have easy access to boating, kayaking, and relaxing by the water. Check out that VR Tour! We are always here to help.

12 Jones Ln, Deep River

179 Bushy Hill Rd, Deep River
$385,000
3 Beds ⋅ 3 Baths ⋅ 24119825 MLS
Charming 3 Bedroom, 2.5 Bath Cape Cod with 2,179 sq. ft., set on 1.6 peaceful acres. Built in 1957 and lovingly maintained by the same owner for over 50 years, this home offers timeless character and comfortable living. The first floor features a spacious living room with propane fireplace, formal dining room, eat-in kitchen, versatile bedroom, full bath, and a cozy den with wood stove. A screened porch and back deck overlook the private yard, perfect for outdoor enjoyment. Upstairs includes two bedrooms, including a large primary suite with full bath, dressing area, and ample closets. Convenient main-level laundry hook-ups. Located in a sought-after area just minutes from Deep River town center, local schools, and the scenic Connecticut shoreline, this property offers the perfect blend of privacy and accessibility.

179 Bushy Hill Rd, 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

152 Union St, Deep River
$379,000
3 Beds ⋅ 1 Baths ⋅ 24129656 MLS
Experience the perfect blend of modern updates and classic charm in this delightful three-bedroom farmhouse, ideally situated in the heart of Deep River Village. The home features beautiful hardwood floors throughout, creating a warm and inviting atmosphere. The spacious kitchen is a chef's delight, complete with a large walk-in pantry for ample storage. The primary bedroom includes a dressing room, providing a functional and stylish space. An exciting feature of this property is the full walk-up attic, offering the potential for additional finished living space to suit your needs. Step outside to the open backyard, which provides plenty of room for gardening and outdoor activities, perfect for enjoying the serene surroundings. A detached one-car garage adds convenience for parking and extra storage. Enjoy the ease of being within walking distance to a variety of restaurants, shops, library, a grocery store, and the scenic Connecticut River Landing. Embrace the vibrant community of Deep River and all it has to offer!

152 Union St, 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

5 Mitchell Ln, Deep River
$366,000
2 Beds ⋅ 2 Baths ⋅ 24139126 MLS
With front porch charm, blooming perennial gardens, and that unmistakable storybook feeling, this home instantly captures your heart. Lovingly cared for over the years, it offers the perfect balance of comfort and character. The updated kitchen opens to a sunlit dining and family area, creating a welcoming space for gatherings. A cozy reading nook and an inviting office and half bath makes the first floor both functional and full of personality. Upstairs, two tranquil bedrooms and a full bath offer a peaceful retreat, all enhanced by hardwood floors. Thoughtful updates include fresh exterior paint, a repointed and repainted chimney, new front porch railings, and refreshed interior walls. A walk-up attic adds generous storage, and all mechanical systems have been diligently maintained. Best of all, you're just a short walk from the town center and the picturesque Town Landing on the Connecticut River - where neighbors gather, boats launch, and sunsets are best enjoyed from the gazebo.

5 Mitchell 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

22 Sylvan Ter, Deep River
$340,000
2 Beds ⋅ 1 Baths ⋅ 24126999 MLS
Welcome to this charming two-bedroom home nestled in a delightful neighborhood! Step onto the inviting covered front porch and into a warm living room featuring hardwood floors and a cozy fireplace. The kitchen opens to a private back deck, ideal for summer evenings or entertaining. There is a dining room off the kitchen which is open to the sunroom with Anderson windows. Garden enthusiasts will love the spacious lot, thoughtfully landscaped with hostas, hydrangeas, & numerous perennials and highlighted by a whimsical frog fountain. With city sewer, some newer windows, and abundant storage throughout, the home offers both comfort and convenience. A pulldown attic & a large basement offer plenty of storage space. Additional perks include a one-car garage tucked underneath and easy access to everything the area has to offer.

22 Sylvan Ter, Deep River

8 Phelps Ln, Deep River
$331,500
2 Beds ⋅ 1 Baths ⋅ 24185691 MLS
Welcome to 8 Phelps Lane, a wonderful opportunity in Deep River's sought after Tri-Town and located in the Landing Neighborhood. With a new roof and new siding already completed, this home offers peace of mind and a solid foundation for future improvements. Inside, the open concept living room, dining area, and kitchen create a bright, functional space ideal for everyday living and entertaining. Move in ready, the home also offers the chance to add your own updates and personal touches to create the ranch retreat you've envisioned. Two wood stoves provide efficient supplemental heat and a warm, inviting atmosphere. The walkout basement offers abundant storage and potential for additional finished living space. Outside, enjoy an oversized deck overlooking the yard, perfect for relaxing or entertaining. An oversized detached garage/workshop with electricity and an additional storage shed provide exceptional space for hobbies, storage, or projects. Enjoy an unbeatable location less than 4 minutes from Deep River Landing for boating, fishing, river access, and watch the historic Essex Steam Train pass. Main Street is approximately a 12 minute walk away, offering local restaurants, ice cream, and charming shops. The elementary school is also within walking distance. Combining location, potential, and value in one of the shoreline area's most desirable communities, this is a rare opportunity to make Deep River home. Sold as is/where is.

8 Phelps Ln, Deep River

102 W Bridge St, Deep River
$325,000
3 Beds ⋅ 3 Baths ⋅ 24165524 MLS
Discover a rare mid-century modern gem offering true one-floor living on 1.5 acres of privacy-yet just a short walk to Deep River's charming village center. This 1950 original is filled with natural light, clean architectural lines, and the warm character that defines the era. The main level features an open living/dining space anchored by a classic fireplace, three bedrooms, and three full baths. A finished lower-level apartment with walkout and separate entrance provides exceptional flexibility for guests, multigenerational living, or future income potential. The home needs renovations and is being sold in as-is condition, making it an outstanding opportunity for buyers with vision. Possible 203K or Home Style Reno mortgages are best if considering financing options. With its private setting, walk-to-town convenience, and strong architectural bones, this property offers tremendous potential to create a stunning modern retreat in one of the Connecticut River Valley's most desirable small towns.

102 W Bridge St, 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

347 Main St, Deep River
$316,000
3 Beds ⋅ 2 Baths ⋅ 24130663 MLS
Discover this inviting ranch-style home, perfectly positioned just minutes from the historic Essex Steam Train along the scenic Connecticut River. Boasting just over 1,200 square feet of living space, this residence features 3 bedrooms, 2 full bathrooms, and a 1-car attached garage. A partially finished walk-out basement adds valuable additional space, ideal for a home office, recreation area, or storage. Step outside to a covered rear deck overlooking a spacious backyard on just under half an acre-perfect for family gatherings, entertaining, or simply enjoying the outdoors. Located just beyond the popular Main Street village area, this property offers a serene setting with convenient access to local shops, dining, and riverfront attractions. While the home is in need of some TLC, it presents a fantastic opportunity to add your personal touches and create your dream space. Don't miss out-schedule a showing today!

347 Main St, Deep River

92 Main St Unit 202, Deep River
$292,000
2 Beds ⋅ 2 Baths ⋅ 24165941 MLS ⋅ The Piano Works BLDG.
Located in the iconic Piano Works Factory, this condo offers easy access from the main street entrance while placing you right in the heart of Deep River's lively village center. Although this is Unit #202, it is actually on the main floor & located just steps from the building's Main St entrance, making daily access simple & convenient. Step into a unique blend of historic charm & modern comfort in this beautifully updated 2-bedroom, 2-full-bath home. Soaring ceilings, exposed brick walls & original beams create an unforgettable loft-style atmosphere. This unit benefits from a wider main-floor layout, allowing space for a small office or reading nook, while also expanding the kitchen into a more open, functional design, rather than a galley dead-end. Two spacious bedrooms provide comfort & privacy, each with its own full bath, ideal for guests, roommates or a dedicated home-office setup. The updated kitchen features granite countertops, ceramic tile flooring, new refrigerator, updated cabinetry & a breakfast bar; this is perfect for cooking & entertaining. New carpeting & fresh paint throughout make this truly 'MOVE IN READY". The building offers 2 laundry rooms (1st & 3rd floors), but you'll appreciate the convenience of the IN-UNIT washer/dryer combo. Deep River is home to the world-famous DRAM (Deep River Ancient Muster, the largest fife & drum gathering in the world, held each year on the 3rd Saturday in July. From this location, you can enjoy

92 Main St Unit 202, Deep River

92 Main St Unit 206, Deep River
$280,000
2 Beds ⋅ 2 Baths ⋅ 24164537 MLS ⋅ The Piano Works BLDG.
Historic Charm Meets Modern Luxury at The Piano Works building. Once the heart of the 19th-century ivory industry, the iconic Piano Works building-now featured on the National Register of Historic Places is home to this stunning, move-in-ready townhouse. This 2 bedroom, 2-bathroom townhouse condominium perfectly balances industrial heritage with 2025 luxury. Inside, you'll find stunning exposed brick, hand-hewn beams, and industrial metal ductwork. In 2025 the Kitchen had a complete renovation featuring granite countertops with a honed finish, brand new cabinets, a new bar top, and premium stainless steel appliances. A convenient first-floor bedroom and tiled full bath offer flexibility, while the upper level opens into a soaring living and dining space anchored by brand-new flooring. On-site amenities include exercise room, community room, dedicated storage locker, outside bike storage and a community grilling area. Located in the heart of Deep River's "Center," you are steps away from a vibrant, walkable town known for its artistic soul and charming Main Street. You can stroll to local boutiques or unwind at Deep River Landing for breathtaking views of the Connecticut River.

92 Main St Unit 206, Deep River

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