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Set on 3.54 private acres in Winthrop, 32 Pinewood Trail offers a farm-to-table lifestyle with plenty of room for a flourishing vegetable garden and a spacious yard to enjoy the seasons. The home itself is thoughtfully designed for flexibility, featuring an IN-LAW APARTMENT with a separate entrance on the lower level, ideal for extended family, or guests. Large windows fill the living spaces with natural light, and the tranquil surroundings create a sense of retreat just minutes from Deep River's charming town center. The interior boasts 4 bedrooms, an open concept kitchen and living room with vaulted ceilings, and a fabulous multi-purpose room above the garage. Elevated details include three separate fireplaces, custom masonry, and hardwood floors throughout. Car enthusiasts and hobbyists will appreciate the ample garage space, perfect for multiple vehicles, equipment, or workshop needs, while the classic barn adds character and endless possibilities for storage, creative projects, or small-scale farming. Enjoy pond views from the spacious deck, and a swimming pool in the warmer months. Whether you envision mornings spent tending a garden, evenings gathered around the firepit, or weekends working on projects in the barn, this property offers the space and setting to make it happen. 32 Pinewood Trail isn't just a home-it's an opportunity to live the lifestyle you've been dreaming of!

4 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 24118253 MLS

Set on 3.54 private acres in Winthrop, 32 Pinewood Trail offers a farm-to-table lifestyle with plenty of room for a flourishing vegetable garden and a spacious yard to enjoy the seasons. The home itself is thoughtfully designed for flexibility, featuring an IN-LAW APARTMENT with a separate entrance on the lower level, ideal for extended family, or guests. Large windows fill the living spaces with natural light, and the tranquil surroundings create a sense of retreat just minutes from Deep River's charming town center. The interior boasts 4 bedrooms, an open concept kitchen and living room with vaulted ceilings, and a fabulous multi-purpose room above the garage. Elevated details include three separate fireplaces, custom masonry, and hardwood floors throughout. Car enthusiasts and hobbyists will appreciate the ample garage space, perfect for multiple vehicles, equipment, or workshop needs, while the classic barn adds character and endless possibilities for storage, creative projects, or small-scale farming. Enjoy pond views from the spacious deck, and a swimming pool in the warmer months. Whether you envision mornings spent tending a garden, evenings gathered around the firepit, or weekends working on projects in the barn, this property offers the space and setting to make it happen. 32 Pinewood Trail isn't just a home-it's an opportunity to live the lifestyle you've been dreaming of!

32 Pinewood Trl, Deep River

$750,000

Welcome to your next chapter at 51 Witch Hazel Drive, a beautifully maintained Cape tucked away at the end of a quiet cul-de-sac. Offering the perfect blend of comfort, flexibility, and privacy, this home is ideal for gathering with loved ones, working from home, or simply enjoying everyday life. Set on a sunny lot with beautifully curated landscaping, the property provides a peaceful retreat while remaining convenient to shoreline amenities. Inside, the thoughtfully designed floor plan is perfect for everyday living and entertaining. The living room features a wood-burning fireplace framed by custom built-ins, while the formal dining room flows seamlessly into the spacious kitchen with granite countertops, abundant cabinetry, and a walk-in pantry. French doors open to a three-season porch overlooking the backyard. The main level also includes a home office, spacious mudroom and full bathroom. Above the attached two-car garage, a large finished room offers flexible space for a family room, or guest retreat. Upstairs are three generously sized bedrooms, including a light-filled primary suite with a sitting area, newly remodeled bathroom, and oversized walk-in closet. An updated full bath and second-floor laundry complete the upper level. Outside, enjoy a Brazilian walnut Ipe deck, three-season porch, in-ground saltwater pool, pool house, fire pit area, and open lawn space for gardening, entertaining, or relaxing. This home truly checks all the boxes! Offers by 6pm Monday

3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24178223 MLS

Welcome to your next chapter at 51 Witch Hazel Drive, a beautifully maintained Cape tucked away at the end of a quiet cul-de-sac. Offering the perfect blend of comfort, flexibility, and privacy, this home is ideal for gathering with loved ones, working from home, or simply enjoying everyday life. Set on a sunny lot with beautifully curated landscaping, the property provides a peaceful retreat while remaining convenient to shoreline amenities. Inside, the thoughtfully designed floor plan is perfect for everyday living and entertaining. The living room features a wood-burning fireplace framed by custom built-ins, while the formal dining room flows seamlessly into the spacious kitchen with granite countertops, abundant cabinetry, and a walk-in pantry. French doors open to a three-season porch overlooking the backyard. The main level also includes a home office, spacious mudroom and full bathroom. Above the attached two-car garage, a large finished room offers flexible space for a family room, or guest retreat. Upstairs are three generously sized bedrooms, including a light-filled primary suite with a sitting area, newly remodeled bathroom, and oversized walk-in closet. An updated full bath and second-floor laundry complete the upper level. Outside, enjoy a Brazilian walnut Ipe deck, three-season porch, in-ground saltwater pool, pool house, fire pit area, and open lawn space for gardening, entertaining, or relaxing. This home truly checks all the boxes! Offers by 6pm Monday

51 Witch Hazel Dr, Deep River

$610,000

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.

2 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 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

$600,000

Natures kaleidoscope defining this serenely & secluded 4.88 acre property nestled in a private sanctuary of which is incomparably resistant to the external world. The Messerschmidt Brook flows freely through the property, embracing soothing sounds. Driving down the driveway you will be captivated by the framework scenery of unspoiled forestry & the open sunny lot. This magical property is close to the 73 acre Messerschmidt state park known for bass fishing w/ boat launch within walking distance. The 3 bedroom cape style house is a beautiful transition to rustic charm & fine detail. Upon entering the front door to the dining rm you will notice the unique rough milled wood work mantle on the masonry fireplace. The oversized Great rm to the left will be the main gathering area with a stunning 2nd masonry fireplace w/ a gorgeous granite stone face! The Great room is open to the newer updated gourmet kit. & dining rm including stainless, granite, newer cabinets, tile backsplash & propane oven range. You will be drawn to the pretty picturesque view from the great rm to natures serenity. Upstairs to the left is a cozy master suite w/ bath. To the right are 2 bedrms & full bath. Updates include: Great rm add.,2 car gar. remodeled kit, new plumbing, electrical, 3 mini splits (only 2 splits needed).Special hand cut woodwork from trees harvested on the property. All updates are town approved. The oversized garage is 30 x40 ft w/12x12 doors, 14 ft ceilings, concrete flrs. run in shed

3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24156110 MLS

Natures kaleidoscope defining this serenely & secluded 4.88 acre property nestled in a private sanctuary of which is incomparably resistant to the external world. The Messerschmidt Brook flows freely through the property, embracing soothing sounds. Driving down the driveway you will be captivated by the framework scenery of unspoiled forestry & the open sunny lot. This magical property is close to the 73 acre Messerschmidt state park known for bass fishing w/ boat launch within walking distance. The 3 bedroom cape style house is a beautiful transition to rustic charm & fine detail. Upon entering the front door to the dining rm you will notice the unique rough milled wood work mantle on the masonry fireplace. The oversized Great rm to the left will be the main gathering area with a stunning 2nd masonry fireplace w/ a gorgeous granite stone face! The Great room is open to the newer updated gourmet kit. & dining rm including stainless, granite, newer cabinets, tile backsplash & propane oven range. You will be drawn to the pretty picturesque view from the great rm to natures serenity. Upstairs to the left is a cozy master suite w/ bath. To the right are 2 bedrms & full bath. Updates include: Great rm add.,2 car gar. remodeled kit, new plumbing, electrical, 3 mini splits (only 2 splits needed).Special hand cut woodwork from trees harvested on the property. All updates are town approved. The oversized garage is 30 x40 ft w/12x12 doors, 14 ft ceilings, concrete flrs. run in shed

272 Westbrook Rd, Deep River

$568,000

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.

3 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 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

$451,000

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.

3 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 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

$393,000

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.

2 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 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

$385,000

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.

3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 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

$316,000

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!

3 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 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

$300,000

Beautiful 2 bedroom right on Star lake with 50 foot of lake frontage is ready for new owners! This property features natural beauty along with modern living interior finishes. Enjoy your viewing!

2 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 24106404 MLS

Beautiful 2 bedroom right on Star lake with 50 foot of lake frontage is ready for new owners! This property features natural beauty along with modern living interior finishes. Enjoy your viewing!

538 Winthrop Rd, Deep River

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