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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.

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

$320,000

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.

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

$315,000

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.

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

$292,000

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

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

$280,000

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.

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

$263,000

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.

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

$250,000

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

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

$245,000

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

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

$240,000

Welcome to Apt. #504 at Georgetown Woods, a 2-bedroom townhouse-style condominium offering a convenient Deep River location. The main level features a kitchen, half bath, and living room with sliding door access to a private patio-perfect for outdoor dining, container gardening, or relaxing among the peaceful surroundings. Beyond the patio, enjoy lawn and open space with the property backing directly to the scenic Canfield Woods Nature Preserve. Upstairs, the home offers a primary bedroom, secondary bedroom, and a full bath. Ideally located near the shops, restaurants, and attractions of Deep River village, with easy access to nearby Centerbrook, Ivoryton, and Essex, including the historic Essex Steam Train and Ivoryton Playhouse. Convenient access to Route 9 provides an easy commute north to Middletown and Hartford or south to the shoreline and I-95 for travel to Boston or New York.

2 Beds ⋅ 2 Baths ⋅ 24174803 MLS ⋅ Georgetown Woods BLDG.

Welcome to Apt. #504 at Georgetown Woods, a 2-bedroom townhouse-style condominium offering a convenient Deep River location. The main level features a kitchen, half bath, and living room with sliding door access to a private patio-perfect for outdoor dining, container gardening, or relaxing among the peaceful surroundings. Beyond the patio, enjoy lawn and open space with the property backing directly to the scenic Canfield Woods Nature Preserve. Upstairs, the home offers a primary bedroom, secondary bedroom, and a full bath. Ideally located near the shops, restaurants, and attractions of Deep River village, with easy access to nearby Centerbrook, Ivoryton, and Essex, including the historic Essex Steam Train and Ivoryton Playhouse. Convenient access to Route 9 provides an easy commute north to Middletown and Hartford or south to the shoreline and I-95 for travel to Boston or New York.

391 Main St Unit 504, Deep River

$235,000

Experience loft-style living in this rare top-floor, partial end unit at the historic Piano Works building. Featuring soaring 9+ foot ceilings, exposed ductwork, and stunning plank ceilings, this condo offers a distinctive character you won't find in typical units. Natural light pours into the spacious living area, enhanced by an additional window unique to this unit. Enjoy the peace and privacy of top-floor living with no neighbors above. Residents have access to a wide range of amenities, including a private storage locker, two common laundry areas, a fully equipped fitness center, and a community room with kitchen. Additional features include bike storage, a fenced dog area, secure entry, and outdoor patio spaces complete with grills and fire pits-perfect for relaxing or entertaining.

2 Beds ⋅ 2 Baths ⋅ 24166622 MLS ⋅ The Piano Works BLDG.

Experience loft-style living in this rare top-floor, partial end unit at the historic Piano Works building. Featuring soaring 9+ foot ceilings, exposed ductwork, and stunning plank ceilings, this condo offers a distinctive character you won't find in typical units. Natural light pours into the spacious living area, enhanced by an additional window unique to this unit. Enjoy the peace and privacy of top-floor living with no neighbors above. Residents have access to a wide range of amenities, including a private storage locker, two common laundry areas, a fully equipped fitness center, and a community room with kitchen. Additional features include bike storage, a fenced dog area, secure entry, and outdoor patio spaces complete with grills and fire pits-perfect for relaxing or entertaining.

92 Main St Unit 417, Deep River

$230,000

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

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

$205,000

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.

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

$205,000

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!

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

$175,000

This is a great location to build your dream home or just use it as the current owners have for a horse pasture. Multiple options for driveway with lots of road frontage and very little, if any rock. Worth a look, the real estate sign goes up next week but you can find the property on GIS as follows: https://www.axisgis.com/Deep_RiverCT/KGzzFuxsLuec

24175827 MLS

This is a great location to build your dream home or just use it as the current owners have for a horse pasture. Multiple options for driveway with lots of road frontage and very little, if any rock. Worth a look, the real estate sign goes up next week but you can find the property on GIS as follows: https://www.axisgis.com/Deep_RiverCT/KGzzFuxsLuec

Cedar Swamp Rd, Deep River

$35,000

Discover the perfect canvas for your dream home at 33 Castle Heights Dr, Deep River. This expansive 36,000 sq ft lot brings a rare opportunity to build in a prime location, conveniently situated near downtown. With an approved septic plan, you can seamlessly bring your vision to life. Bring your builder and explore the possibilities of this exceptional property. Don't miss out on this prime piece of real estate; reach out today to learn more! Please do not walk the property without an agent present. Personal property on the lot conveys.

24166136 MLS

Discover the perfect canvas for your dream home at 33 Castle Heights Dr, Deep River. This expansive 36,000 sq ft lot brings a rare opportunity to build in a prime location, conveniently situated near downtown. With an approved septic plan, you can seamlessly bring your vision to life. Bring your builder and explore the possibilities of this exceptional property. Don't miss out on this prime piece of real estate; reach out today to learn more! Please do not walk the property without an agent present. Personal property on the lot conveys.

33 Castle Hts, Deep River

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