Refine Search
Map
Sort by
$1,065,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24192002 MLS
Privately set on over three picturesque acres in Deep River, just moments from the Essex town line, this extraordinary custom home is the result of an exceptional architectural transformation, blending timeless New England character with thoughtful, high-end design. Enjoy a peaceful, private setting while being just minutes from the charming village centers of Deep River and Essex, with their acclaimed restaurants, boutique shops, marinas, yacht clubs, the Connecticut River Museum, and the historic Griswold Inn. A comprehensive redesign of the home's exterior was completed by renowned architect Christopher Arelt, featuring all-new windows, structural insulated panels for enhanced energy efficiency, cedar shingle siding, copper gutters, Azek trim, a 4-zone heating system, an expansive Ipe deck and stairs, a bluestone patio, and a private outdoor shower. A brand-new well, drilled in May, and a whole-house generator powered by a 500-gallon underground propane tank provide year-round comfort and peace of mind. The home's showpiece is the spectacular four-season sunroom. This breathtaking space features a coffered beadboard ceiling, rich Brazilian cherry flooring, walls of windows, a wood-burning stove, custom built-in seating, and French doors opening onto the expansive Ipe deck, creating an extraordinary setting for year-round living and entertaining.

106 Meadow Woods Rd, Deep River
$450,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24192206 MLS
Welcome to this inviting 3-bedroom split-level ranch, ideally situated within walking distance to the heart of Chester Village. Designed for comfortable living and entertaining, the home features a spacious family room with sliders leading to a large deck overlooking the inground pool. The backyard is an outdoor retreat complete with a pool house, gazebo with electricity, mature fruit trees, and a large open yard offering endless possibilities. Inside, you'll find two fireplaces-one in the living room and another in the lower-level recreation room-creating warm and welcoming spaces throughout the seasons. The remodeled kitchen features granite countertops, ample cabinetry, and a functional layout for everyday living. The primary bedroom includes a private half bath, and the two-car attached garage provides plenty of storage and convenience. Recent upgrades include a newer boiler, central air condenser, and garage doors, providing added value and peace of mind. Just a short walk from Chester Village, you'll enjoy convenient access to art galleries, locally owned restaurants, unique boutiques, and seasonal community events. This home offers a wonderful opportunity to add your personal touches while enjoying a spacious property, exceptional outdoor amenities, and all that Chester has to offer.

22 Goose Hill Rd, Chester
$1,650,000
2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24191007 MLS
Spectacular South Cove views, contemporary design, and effortless one-level living define this exceptional ranch in the heart of historic Essex. Perched above the tranquil waters of South Cove, this beautifully appointed home offers more than 3,000 square feet* of light-filled living space, where expansive windows frame ever-changing water views and create a seamless connection between indoors and out. The open floor plan is ideal for entertaining and everyday living. A spacious deck overlooks beautifully landscaped grounds and the sparkling waters of South Cove-perfect for morning coffee, alfresco dining, or evening cocktails. At the entrance, a welcoming stone terrace with a fire pit creates an inviting space to gather with family and friends. Lush, thoughtfully designed, low-maintenance landscaping enhances the home's privacy and natural beauty. Just minutes from historic Essex, recently named Yankee Magazine's Best Small Town in New England, the village has also earned national recognition as the top-ranked community in The 100 Best Small Towns in America and was celebrated as "The Perfect Small American Town" in 1,000 Places to See Before You Die. Discover charming boutiques, acclaimed restaurants, marinas, the Connecticut River Museum, and the iconic Griswold Inn. *Fantastic potential for primary or in-law suite on 1,200 SF lower level. Area not included on town card.

24 Mallard Point Rd, Essex
$465,000
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24190169 MLS ⋅ Heritage Cove BLDG.
Stunning end unit, second floor, peaceful views of the Falls River with a warming fireplace to be cozy on cooler days are just a few of the unique features of this completely updated home at Heritage Cove. The living and dining area offer a bright open floor plan, two bedrooms, one large remodeled bath, updated kitchen with butcher board countertop, private balcony with stairs as a separate private entrance with water views from living room to the kitchen. Meander from this home on sidewalks to all things Essex Village! Shops, restaurants, boutiques, marinas, yacht clubs and more. This is a fabulous opportunity for waterfront carefree living in Essex.

85 River Rd Unit M5, Essex
$399,900
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 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
$849,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24182027 MLS
16 Glen Grove Road....a stunning custom built 2023 Colonial privately set on 4.53 acres in desirable Deep River. Tucked well off the road and surrounded by beautiful stone walls, this property offers exceptional privacy and endless possibilities to enjoy the outdoors, from garden areas & gorgeous rock walls, to creating your own walking trails throughout the wooded landscape. Inside, you'll find approximately 2,782 square feet of thoughtfully designed living space. The bright, open kitchen is the heart of the home, featuring a center island, gorgeous Narragansett green cabinetry, elegant gold fixtures, and seamless flow into the spacious family room with a fireplace and sliders leading to the rear deck. A formal dining room, additional living room, and convenient half bath complete the main level, offering flexible spaces for both everyday living and entertaining. Upstairs, the primary suite features a spacious walk-in closet and private ensuite bath. Three additional bedrooms and a full bath in the hallway provide plenty of room for family, guests, or home office needs. This home offers the benefits of newer construction along with an energy-efficient heat pump system providing both heating and cooling. Move right in and enjoy modern comfort, privacy, and room to grow.

16 Glen Grove Rd, Deep River
$659,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24170783 MLS
Good design is all about the details and this well maintained custom Colonial is just what you have been looking for in the perfect shoreline home. Recently updated, the current owner's signature style has magically taken this charming home from ordinary to extraordinary with her colorful design. From the warm and welcoming entrance, to the well-appointed kitchen or the cozy family room centered around the fireplace, this home offers a lifestyle that embraces quality and comfort. Ideal for entertaining and special occasions, the formal living room and dining room offer guests the perfect balance of relaxed and refined. Upstairs you'll find the primary suite with a walk-in-closet and private bathroom, along with three lovely guest bedrooms with a shared bath. A spacious two-car attached garage offers extra storage and is perfect for all your gardening needs. Enjoy abundant wildlife while savoring the sunshine from your own private deck over-looking park-like grounds; lasting memories will be made with friends and family around a charming fire pit. Prominently set on 1.5 acres, this special home is bordered natural plantings, beautiful rock out-croppings and a variety of stately trees that adorn the property. Located close to Essex Village and Deep River Center this property also offers easy access to several hiking trails and nature preserves in the area. Whether you are looking for a full-time residence or the ideal weekend retreat it's the perfect place to call home.

73 Long Hill Rd, Deep River
$750,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24160737 MLS
Set in a serene Essex setting, this lovely contemporary home offers a rare opportunity to enjoy waterfront living on Tiffany Pond. Surrounded by beautifully landscaped grounds, the property provides a peaceful retreat with beautiful natural views in every direction. Designed for both comfort and style, the home features 3 spacious bedrooms and 2.5 baths, including a desirable first-floor primary bedroom for easy living. The sunken living room is filled with natural light and enhanced by elegant French doors, creating a warm and inviting space perfect for relaxing or entertaining. A double-sided fireplace seamlessly connects the living room and dining room, creating a warm ambiance ideal for gatherings, while a second fireplace adds additional charm and comfort. A mid-century inspired kitchen with an eat-in area and stainless steel appliances provides a functional space. Step outside and enjoy direct access to the pond-perfect for kayaking, canoeing, or simply taking in the tranquil surroundings. Whether you're looking for a year-round residence or a weekend escape, this exceptional property offers a unique blend of modern design and nature's beauty.

199 Westbrook Rd, Essex
$209,900
1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24168235 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
$3,150,000
4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24166793 MLS
Set along a coveted stretch of the Connecticut River, this stunning, turnkey waterfront compound offers a rare convergence of privacy, protected views, and deep water access-just over one mile from the heart of Chester Village. Encompassing 2.65 acres with 285 feet of direct river frontage, the property unfolds as a true waterfront retreat. Manicured grounds lead seamlessly from the residence and terrace to a deepwater dock designed for serious boating enthusiasts, and onward to a beach-creating an immersive riverfront experience rarely found in the CT River Valley. Rooted in historic design and masterfully renovated in 2010, the residence reflects timeless New England architecture while incorporating modern livability. The result is a home that feels both enduring and refined. A standout feature for collector/hobbyists are six garage bays, offering exceptional space for auto enthusiasts, boating and recreational storage. Designed to accommodate a range of lifestyles, this offering is equally compelling as a luxury weekend retreat or a multi-generational compound, with space and setting that invite both privacy and gathering. Despite its seclusion, the estate remains connected to the vibrant charm of Chester Village. Adding to the setting's unique appeal, the seasonal Connecticut Valley Railroad introduces a nostalgic dimension, reflecting the rich area history. A rare offering where protected waterfront, architectural integrity and lifestyle converge. Welcome to East View.

288 Middlesex Ave, Chester
$6,500,000
5 Beds ⋅ 7 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24143703 MLS
A WORLD-CLASS PRIVATE ESTATE SET ON 9.31 GATED ACRES. Nestled behind a private gated entry, this extraordinary CT River Valley estate is a rare luxury compound of architectural distinction, solitude, & resort-caliber amenities. Thoughtfully composed across 5 distinct structures, the property blends modern luxury, European influences, & timeless craftsmanship amid curated landscapes, stone pathways, terraces, & over 6,000sf of refined outdoor living space. This is a truly exceptional, once-in-a-lifetime offering. A long winding driveway gradually reveals an exclusive enclave where the outside world fades away. Stucco structures, cedar shake roofs, & copper gutters emerge in sequence, unified by professionally landscaped grounds, irrigation, & exterior lighting that enhances the estate's serene atmosphere. Completely rebuilt in 2012, & finished in 2015, the Main Residence is a masterclass in quality & livability. Rich millwork, custom cabinetry, radiant-heated hardwood floors, transom windows, & skylights define interiors that feel both elegant & inviting. A boutique-style coat room & jewel-box powder room immediately signal the home's uncompromising level of finish. The show-stopping kitchen features high-gloss bespoke cabinetry, nickel hardware, & a sculptural range hood beneath tall silver-leaf detailed ceilings. A substantial Calacatta marble island integrates a 2nd sink, butcher block, & concealed storage. Chef-grade appliances include SubZero, Wolf, & Miele. *CONTINUED*

252 River Rd, Deep River

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.