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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.

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

$899,999

Introducing an opportunity to build your dream home on a secluded 3-acre interior lot in beautiful Deep River. Located off scenic Glen Grove Road, this custom-designed Modern Farmhouse offers over 3,300 sq ft of thoughtfully planned living space, blending timeless architecture with the flexibility to tailor finishes to your vision. This to-be-built home features 4 bedrooms, 2.5 bathrooms, and a smart, open-concept layout ideal for modern living. The main level boasts expansive gathering spaces filled with natural light, with seamless flow between the kitchen, dining, and living areas-perfect for everyday living or entertaining. The oversized primary suite is privately situated upstairs above the 3-car garage, offering a quiet retreat with ample space and views of the surrounding woods. Three additional bedrooms upstairs provide space for family, guests, or a home office. Highlights include: Interior 3-acre lot offering privacy and natural beauty 3-car garage with direct access to mudroom and laundry High-efficiency construction and energy-conscious systems Covered porch and flexible outdoor living potential Full customization of layout and finishes available Enjoy the charm of Deep River living-just minutes from downtown, the Connecticut River, and the shops and restaurants of the shoreline. This is a rare opportunity to create a fully custom home in a peaceful, sought-after location.

4 Beds ⋅ 3 Baths ⋅ 24098210 MLS

Introducing an opportunity to build your dream home on a secluded 3-acre interior lot in beautiful Deep River. Located off scenic Glen Grove Road, this custom-designed Modern Farmhouse offers over 3,300 sq ft of thoughtfully planned living space, blending timeless architecture with the flexibility to tailor finishes to your vision. This to-be-built home features 4 bedrooms, 2.5 bathrooms, and a smart, open-concept layout ideal for modern living. The main level boasts expansive gathering spaces filled with natural light, with seamless flow between the kitchen, dining, and living areas-perfect for everyday living or entertaining. The oversized primary suite is privately situated upstairs above the 3-car garage, offering a quiet retreat with ample space and views of the surrounding woods. Three additional bedrooms upstairs provide space for family, guests, or a home office. Highlights include: Interior 3-acre lot offering privacy and natural beauty 3-car garage with direct access to mudroom and laundry High-efficiency construction and energy-conscious systems Covered porch and flexible outdoor living potential Full customization of layout and finishes available Enjoy the charm of Deep River living-just minutes from downtown, the Connecticut River, and the shops and restaurants of the shoreline. This is a rare opportunity to create a fully custom home in a peaceful, sought-after location.

Glen Grove Road, Deep River

$699,900

This Stunning, completely remodeled ranch style home is truly move in ready! With an open concept living area, perfect for entertaining or everyday living. There is pleanty of kitchen space with an island, new cabinets & quartz countertops and new appliances, living room area with gas fireplace and dining space. High ceilings and plenty of window to let in the natural light. On one side of the house you have the Master bedroom with two walk-in closets & private master bath. The Laundry room and half bath. On the other side of the house are two additional bedrooms & a full bath. Enjoy the privacy of your back deck accessable from both the living room and master bedroom. The lot is just over two acres, surrounded by private lightly wooded land. With over 1700 sq ft of living space there is still room for expansion over the attached two car garage. With entrances from both the garage or outside, this space has been started for an in-law apartment. Frame work, electric & plumbing have been started. Additional photos will be added soon.

3 Beds ⋅ 3 Baths ⋅ 24208142 MLS

This Stunning, completely remodeled ranch style home is truly move in ready! With an open concept living area, perfect for entertaining or everyday living. There is pleanty of kitchen space with an island, new cabinets & quartz countertops and new appliances, living room area with gas fireplace and dining space. High ceilings and plenty of window to let in the natural light. On one side of the house you have the Master bedroom with two walk-in closets & private master bath. The Laundry room and half bath. On the other side of the house are two additional bedrooms & a full bath. Enjoy the privacy of your back deck accessable from both the living room and master bedroom. The lot is just over two acres, surrounded by private lightly wooded land. With over 1700 sq ft of living space there is still room for expansion over the attached two car garage. With entrances from both the garage or outside, this space has been started for an in-law apartment. Frame work, electric & plumbing have been started. Additional photos will be added soon.

103 Bushy Hill Rd, Deep River

$699,900

MAJOR PRICE REDUCTION!! An exceptional opportunity to own over 3,100 square feet w/ waterfront frontage at an incredible value! Offering 4 bedrooms, 2.5 baths & 3,143 square feet of living space, this spacious Colonial is tucked away on a private cul-de-sac overlooking Pratt Read Reservoir w/ approximately 200 feet of waterfront frontage. The home features all-new plumbing, updated bathrooms & a newer HVAC system, with just a few remaining updates offering the next owner an opportunity to add their own style & finishing touches. The spacious eat-in kitchen w/ a large pantry opens to a welcoming family room w/ a gas fireplace, while formal living & dining rooms provide flexible space for entertaining, a home office or den. A dramatic two-story foyer creates an impressive entrance. Upstairs, the primary suite features dual walk-in closets & a spacious bath with a soaking tub & large walk-in shower. The walkout lower level is filled w/ natural light & offers tremendous potential for additional finished living space. Enjoy beautiful water views & recreation right from your backyard-kayak, canoe, fish or simply relax on the oversized deck overlooking the reservoir w/ direct water access. Conveniently located near a popular pick-your-own orchard & just minutes from Valley Regional High School. At $699,900, finding a home with more than 3,000 square feet, waterfront access & this much potential in town is a rare opportunity. Bring your finishing touches & make it yours!!

4 Beds ⋅ 3 Baths ⋅ 24205311 MLS

MAJOR PRICE REDUCTION!! An exceptional opportunity to own over 3,100 square feet w/ waterfront frontage at an incredible value! Offering 4 bedrooms, 2.5 baths & 3,143 square feet of living space, this spacious Colonial is tucked away on a private cul-de-sac overlooking Pratt Read Reservoir w/ approximately 200 feet of waterfront frontage. The home features all-new plumbing, updated bathrooms & a newer HVAC system, with just a few remaining updates offering the next owner an opportunity to add their own style & finishing touches. The spacious eat-in kitchen w/ a large pantry opens to a welcoming family room w/ a gas fireplace, while formal living & dining rooms provide flexible space for entertaining, a home office or den. A dramatic two-story foyer creates an impressive entrance. Upstairs, the primary suite features dual walk-in closets & a spacious bath with a soaking tub & large walk-in shower. The walkout lower level is filled w/ natural light & offers tremendous potential for additional finished living space. Enjoy beautiful water views & recreation right from your backyard-kayak, canoe, fish or simply relax on the oversized deck overlooking the reservoir w/ direct water access. Conveniently located near a popular pick-your-own orchard & just minutes from Valley Regional High School. At $699,900, finding a home with more than 3,000 square feet, waterfront access & this much potential in town is a rare opportunity. Bring your finishing touches & make it yours!!

77 Falls Landing Rd, Deep River

$695,000

Welcome home to 26 Spring Street, c. 1830. Originally the residence of Asahel and Adelia Watrous, this story-book Antique has been thoughtfully and lovingly restored by its present owners. The first floor welcomes you with a beautifully remodeled eat-in kitchen, where stone countertops, a farmhouse sink, stainless appliances, and vaulted tin ceilings create an atmosphere that feels both timeless and enchanting. At the heart of the home lies a gracious family room, encircled by inviting spaces: a generous pantry, a cozy living room with wood stove, a charming library with built-in bookcases, a small study, and a full bathroom. The library, with its intimate character, could easily serve as a first-floor bedroom. In the light-filled upstairs there are two to three tranquil bedrooms, a spa-like full bathroom, convenient laundry, and a spacious walk-in closet. The property includes an electrified two-car garage that is architecturally harmonious with the house as well as a utility shed. Outdoors, a beautifully fenced patio-complete with a bespoke garden created for feline companions-opens onto a large, serene, and very private yard, a setting that evokes the feeling of a sheltered retreat, while being just steps from Deep River's quaint center of and a short walk to the Connecticut River Landing.

4 Beds ⋅ 2 Baths ⋅ 24215262 MLS

Welcome home to 26 Spring Street, c. 1830. Originally the residence of Asahel and Adelia Watrous, this story-book Antique has been thoughtfully and lovingly restored by its present owners. The first floor welcomes you with a beautifully remodeled eat-in kitchen, where stone countertops, a farmhouse sink, stainless appliances, and vaulted tin ceilings create an atmosphere that feels both timeless and enchanting. At the heart of the home lies a gracious family room, encircled by inviting spaces: a generous pantry, a cozy living room with wood stove, a charming library with built-in bookcases, a small study, and a full bathroom. The library, with its intimate character, could easily serve as a first-floor bedroom. In the light-filled upstairs there are two to three tranquil bedrooms, a spa-like full bathroom, convenient laundry, and a spacious walk-in closet. The property includes an electrified two-car garage that is architecturally harmonious with the house as well as a utility shed. Outdoors, a beautifully fenced patio-complete with a bespoke garden created for feline companions-opens onto a large, serene, and very private yard, a setting that evokes the feeling of a sheltered retreat, while being just steps from Deep River's quaint center of and a short walk to the Connecticut River Landing.

26 Spring St, Deep River

$650,000

Waterfront home on Tower Hill Lake. Main house has 3 bedrooms and 2 full baths. The lower level with its own separate entrance would make a great in-law/ Au-pair apartment or ADU. Views from most rooms. 2 separate Driveways. The house sits on .5 acres with a 2nd .25 acre waterfront lot. Beautiful lake for quiet enjoyment. No power boats allowed on lake. **Photos are edited with items removed from the rooms, items are not removed.***

3 Beds ⋅ 3 Baths ⋅ 24210795 MLS

Waterfront home on Tower Hill Lake. Main house has 3 bedrooms and 2 full baths. The lower level with its own separate entrance would make a great in-law/ Au-pair apartment or ADU. Views from most rooms. 2 separate Driveways. The house sits on .5 acres with a 2nd .25 acre waterfront lot. Beautiful lake for quiet enjoyment. No power boats allowed on lake. **Photos are edited with items removed from the rooms, items are not removed.***

32 Tower Hill Lake Rd, Deep River

$599,900

Walking distance to Downtown and a brand new roof! Welcome to 240 Main Street. Full of character and warm appeal, this 3-bedroom, 2-full-bath home offers a unique combination of indoor comfort and a prime outdoor setting. Step inside to discover a beautiful, well-appointed kitchen outfitted with a professional Jade stove-perfect for culinary enthusiasts-with views opening out to a beautifully landscaped, private backyard retreat. Built-ins and original details continue throughout the entire home, while thoughtful updates maximize the use of living space. With lots of flex space in the barn, the first floor hosts amazing space for a gym, second office, hobby room or a billiard room. Upstairs, a private office provides a quiet work-from-home setup. Outdoors, the peaceful, tree-lined yard includes a charming potting shed and abuts a serene church field for maximum privacy. Positioned right across the street from the local park, playground, and baseball fields, you'll enjoy front-row access to community recreation while maintaining your own private oasis. Schedule your private tour today!

3 Beds ⋅ 2 Baths ⋅ 24200740 MLS

Walking distance to Downtown and a brand new roof! Welcome to 240 Main Street. Full of character and warm appeal, this 3-bedroom, 2-full-bath home offers a unique combination of indoor comfort and a prime outdoor setting. Step inside to discover a beautiful, well-appointed kitchen outfitted with a professional Jade stove-perfect for culinary enthusiasts-with views opening out to a beautifully landscaped, private backyard retreat. Built-ins and original details continue throughout the entire home, while thoughtful updates maximize the use of living space. With lots of flex space in the barn, the first floor hosts amazing space for a gym, second office, hobby room or a billiard room. Upstairs, a private office provides a quiet work-from-home setup. Outdoors, the peaceful, tree-lined yard includes a charming potting shed and abuts a serene church field for maximum privacy. Positioned right across the street from the local park, playground, and baseball fields, you'll enjoy front-row access to community recreation while maintaining your own private oasis. Schedule your private tour today!

240 Main St, Deep River

$499,000

Imagine strolling along charming brick sidewalks to your favorite downtown restaurant, browsing local gift shops, or enjoying the tradition of Deep River's beloved historic Muster in July right from your front porch! Built in 1918, this well-maintained Colonial offers a wonderful opportunity to experience the character, history, and welcoming community that make this Connecticut river town so special. Step inside this traditional New England home and craftsmanship shines through from the rich wood molding to the spacious foyer with an amazing staircase with classic box newel post. With four bedrooms, 1.5 baths, first floor laundry, expansive kitchen and cozy family room, the home offers an inviting layout filled with timeless character and everyday functionality. The enclosed front porch is a dream come true (BYOR-Bring Your Own Rocker!), while the large side deck provides space for outdoor dining and entertaining. The walk-up attic is a real surprise, measuring 26' x 24' with a high ceiling. One can easily image finishing this space into a primary suite or additional living space! Recent updates include a new boiler, newer roof, and connection to city sewer. If you are looking for a walkable, in-town location, this is it! Recreation fields and a well-equipped playground are across the street while restaurants, gift shops, the public library, the Deep River Historical Society, hiking trails, seasonal farmers' market, supermarket, pharmacy, and 24-hour gym are close by.

4 Beds ⋅ 2 Baths ⋅ 24214902 MLS

Imagine strolling along charming brick sidewalks to your favorite downtown restaurant, browsing local gift shops, or enjoying the tradition of Deep River's beloved historic Muster in July right from your front porch! Built in 1918, this well-maintained Colonial offers a wonderful opportunity to experience the character, history, and welcoming community that make this Connecticut river town so special. Step inside this traditional New England home and craftsmanship shines through from the rich wood molding to the spacious foyer with an amazing staircase with classic box newel post. With four bedrooms, 1.5 baths, first floor laundry, expansive kitchen and cozy family room, the home offers an inviting layout filled with timeless character and everyday functionality. The enclosed front porch is a dream come true (BYOR-Bring Your Own Rocker!), while the large side deck provides space for outdoor dining and entertaining. The walk-up attic is a real surprise, measuring 26' x 24' with a high ceiling. One can easily image finishing this space into a primary suite or additional living space! Recent updates include a new boiler, newer roof, and connection to city sewer. If you are looking for a walkable, in-town location, this is it! Recreation fields and a well-equipped playground are across the street while restaurants, gift shops, the public library, the Deep River Historical Society, hiking trails, seasonal farmers' market, supermarket, pharmacy, and 24-hour gym are close by.

8 Southworth St, Deep River

$325,000

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

$289,900

A Unique opportunity, 2 Homes on 1 Lot. Plus a barn/garage. First Home has 2 bedrooms and is 1,061 sqft. Second Home has one bedroom and is 350 sqft. Separate town water and sewer to each home. Ready for your updating! Electric 100 AMPS each.

3 Beds ⋅ 3 Baths ⋅ 24200726 MLS

A Unique opportunity, 2 Homes on 1 Lot. Plus a barn/garage. First Home has 2 bedrooms and is 1,061 sqft. Second Home has one bedroom and is 350 sqft. Separate town water and sewer to each home. Ready for your updating! Electric 100 AMPS each.

1721 Winter Ave, Deep River

$289,900

A unique opportunity, 2 Homes on 1 Lot. Plus a barn/garage. First Home has 2 bedrooms and is 1,061 sqft. Second Home has one bedroom and is 350 sqft. Separte town water and sewer to each home. Ready for your updating! Electric 100 AMPS each.

2 Beds ⋅ 2 Baths ⋅ 24192157 MLS

A unique opportunity, 2 Homes on 1 Lot. Plus a barn/garage. First Home has 2 bedrooms and is 1,061 sqft. Second Home has one bedroom and is 350 sqft. Separte town water and sewer to each home. Ready for your updating! Electric 100 AMPS each.

17 & Ave, Deep River

$281,200

Investors take notice. Ranch-style home located in Deep River with lots of potential. Great lot and location. Property sits on over an acre of land, close to schools and parks. Property needs work and will not qualify for government financing. Property will be offered for sale. Buyers must sign up and place bids through Xome. All auction properties are subject to a purchaser's premium pursuant to the event, and auction assignments & conditions minimums will apply. Buyers and buyer's agent to verify any and all info.

3 Beds ⋅ 2 Baths ⋅ 24153759 MLS

Investors take notice. Ranch-style home located in Deep River with lots of potential. Great lot and location. Property sits on over an acre of land, close to schools and parks. Property needs work and will not qualify for government financing. Property will be offered for sale. Buyers must sign up and place bids through Xome. All auction properties are subject to a purchaser's premium pursuant to the event, and auction assignments & conditions minimums will apply. Buyers and buyer's agent to verify any and all info.

97 Bushy Hill Rd, Deep River

$229,000

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?!

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

$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

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