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31 Whittlesey Brook Rd, Deep River
$630,000
3 Beds ⋅ 3 Baths ⋅ 24137121 MLS
Extremely rare - one owner home. A picture-perfect and pristine cape tucked away on a quiet tree-lined street ending in a cul-de-sac. As you enter the foyer through the front door you will appreciate thoughtful architectural details and gleaming hardwood floors. The updated kitchen features upscale stainless appliances, Corian countertops, a tile backsplash, a bumped-out window behind the sink, and a breakfast nook. The breakfast nook leads to an impressive solarium at the back of the house overlooking the private back yard, and is a perfect spot for savoring both morning coffee and winding down with evening cocktails. The light and bright solarium has French doors that open out to a gracious patio in the back yard. There is also a cozy den with gas stove, a formal dining room, living room with wood burning fireplace, a half bath/laundry room, and an oversized two-car garage on the first floor. Upstairs you will find a master bedroom with an updated ensuite bath and plenty of closet space. There are also two more bedrooms and another updated full bathroom on the second floor. The finished walk-out basement features a family room area with built-in cabinetry, another fireplace, and plenty of extra space for a pool table, exercise equipment, workshop, or crafting area.

31 Whittlesey Brook Rd, Deep River

87 Rattling Valley Rd, Deep River
$525,000
3 Beds ⋅ 3 Baths ⋅ 24134107 MLS
For the first time on the market, this enchanting 4.6 acre property invites you to live immersed in nature - where wooded trails, abundant wildlife, and water access are part of everyday life. Sharing a property line with the pristine Pratt Cove, a protected wetland alive with birdlife and native plants, this home is a true sanctuary for outdoor enthusiasts. Launch a canoe from your backyard and paddle through the cove's tranquil waters all the way to the Connecticut River, or simply enjoy the ever-changing sights, sounds and colors of the seasons from your deck. Inside, an open floor plan connects the living and dining areas, designed for both everyday comfort and memorable gatherings. The dining space centers around a striking stone fireplace with a wood-burning insert, creating a warm, romantic backdrop for winter meals. Vaulted ceilings and skylights, overside sliders fill the home with natural light, while a wrap-around deck offers seamless indoor-outdoor living and a perfect vantage point for watching deer, foxes, and migrating birds. Downstairs, the expansive basement provides even more flexibility, with a finished room ideal for a home office, gym, or media space - plus ample storage to keep everything organized and out of sight. With 3 bedrooms and 2 full bathrooms (1 half), there's space for friends and guests alike- whether you envision this as your year-round residence or a peaceful weekend retreat. Every window offers a glimpse of the surrounding natural beauty.

87 Rattling Valley Rd, 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

24 Elm St, Deep River
$454,000
5 Beds ⋅ 4 Baths ⋅ 24130599 MLS
Ideally located in the heart of Deep River, this charming and versatile residence offers convenience, character, and room to grow. A sidewalk-lined street provides easy access to village shopping, dining, and Route 9, while the home itself enjoys a peaceful setting along the Deep River stream, which connects Rogers Pond and Keyboard Pond. Inside, a spacious floor plan features a first-floor primary suite with private bath, a large living room with fireplace, formal dining room, and an inviting eat-in kitchen. Multiple living spaces include a first-floor office, an upstairs den, and four to five bedrooms, providing flexibility for work, guests, or hobbies. The home is filled with natural light and has been recently refreshed and painted throughout. Outdoor living is equally inviting, with a screened porch accessed from both the living room and kitchen, and a broad brick patio overlooking a long, level lawn-perfect for games, entertaining, or simply relaxing under a shade tree. A handsome post-and-beam barn offers two garage bays plus abundant space for a workshop, storage or future renovation. Combining period charm with modern comfort, this Deep River gem offers endless possibilities in a truly convenient and scenic setting.

24 Elm 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

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

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

32 Pinewood Trl, Deep River
$825,000
4 Beds ⋅ 4 Baths ⋅ 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

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