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38 Bay Street Unit W401, Westerly
$2,300,000
2 Beds ⋅ 2 Baths
Discover the coastal lifestyle in this beautiful two-bedroom, two-bath residence at the Watch Hill Inn, ideally located in the heart of the charming Resort Village of Watch Hill. Offering 1,000 sq ft of thoughtfully designed living space, this beautifully appointed condo features fabulous views of Watch Hill Harbor to enjoy while sipping morning coffee, afternoon cocktails, or simply taking in the ever-changing beauty of the Watch Hill Harbor. Inside showcases a coastal aesthetic with bamboo & Italian marble flooring, granite countertops, custom wood cabinetry & a beautiful open-concept living and kitchen area. Large windows bring the spectacular harbor views into the living space, creating a warm and inviting retreat that is equally suited to relaxing and entertaining. Owners have the opportunity to participate in the Ocean House Rental Program and, while in residence, enjoy access to amenities at the Ocean House Resort Hotel and Weekapaug Inn, including the Ocean House's private Atlantic Ocean beach, dining, Spa, fitness center, croquet, shuttle service, and daily housekeeping. Step outside and enjoy all that Watch Hill has to offer, from its picturesque harbor and boutique shops to the historic Flying Horse Carousel, Olympia Tea Room, Sift Bakery, St. Clair Annex, and more. A timeless coastal destination and a rare opportunity to own a coastal retreat in one of New England's most sought-after seaside villages

38 Bay Street Unit W401, Westerly

Listing courtesy of Lila Delman Compass. Contact:

16 Waters Edge Road, Westerly
$8,250,000
5 Beds ⋅ 4 Baths
A rare opportunity to own directly on the protected waters of Watch Hill Harbor. Beautifully renovated and thoughtfully updated, this classic 1905 coastal cottage offers 5BR/3.1+BA, 3,172 SF and harbor views from nearly every room. Gracious living and dining spaces, an inviting family room and well-appointed kitchen open naturally toward the water, while a covered screened porch sets the stage for slow summer mornings, relaxed dinners and unforgettable western sunsets. Set on .68 acres, the property includes a private dock and mooring - an increasingly scarce amenity offering immediate access to Stonington, Mystic, Fishers Island, Block Island, Long Island Sound and the Atlantic. Just moments from Watch Hill Village, beaches, Ocean House and the area's storied clubs, the property captures the relaxed sophistication that has defined this seaside enclave for generations. Ideally positioned between New York and Boston, Watch Hill is readily reached via I-95, Amtrak in Westerly and nearby jet-capable Westerly State Airport - offering uncommon accessibility without the travel friction of many East Coast resort destinations. Arrive for the weekend, step aboard from your own dock, and settle instantly into the rhythm of life by the water. 16 Water's Edge Road brings together timeless New England character, boating, privacy and effortless coastal living in one exceptional setting.

16 Waters Edge Road, Westerly

Listing courtesy of William Pitt Sotheby's Int'l. Contact:

19 Littlebrook Road, Westerly
$925,000
3 Beds ⋅ 4 Baths
Nestled in a peaceful, private setting with an abundance of wildlife, this striking contemporary home at 19 Littlebrook Road offers a rare blend of modern design, flexible living space, and serene views of Doc Lewis Pond, a protected parcel within the Westerly Land Preserve. The two primary living levels offer 2,169 square feet, with an additional 1,167 square feet of sunny space on the lower level offering versatility for a variety of lifestyles. The home features 3 bedrooms and 3.5 bathrooms, including a stunning primary suite with exposed wood beams, walk-in closet, and private full bathroom. Abundant windows throughout fill the home with natural light while showcasing the surrounding landscape. Architectural details include a dramatic spiral staircase, a custom built-in bookcase area, and 2 cozy wood-burning stoves. The home spans two main living levels, with access to a third-floor area leading to a private balcony, perfect to enjoy a peaceful pond and nature views. The finished lower level offers flexibility as a potential in-law area or guest retreat, complete with a full bathroom, living and dining area, and laundry. Outdoor living is equally inviting, with 3 decks and a patio overlooking the tranquil setting. The large driveway accommodates up to four vehicles, while a storage shed provides additional space for outdoor equipment. This one-of-a-kind waterfront home combines contemporary style, flexible living spaces, and a picturesque setting that's hard to find.

19 Littlebrook Road, Westerly

Listing courtesy of SERHANT.. Contact:

18 Fallon Trail, Westerly
$1,295,000
3 Beds ⋅ 2 Baths
A rare opportunity to own one of Southern Rhode Island's most distinctive custom timber frame homes, where timeless craftsmanship, modern efficiency, and effortless coastal living unite. Privately nestled on 1.5 wooded acres in an exclusive cul-de-sac just five minutes from Westerly's beaches, golf, tennis, and vibrant downtown, this exceptional three-year-old residence directly borders the 900-acre Woody Hill Management Area with over 75 miles of scenic hiking and biking trails just steps from your backyard. Wake each morning surrounded by nature and return home to a residence designed for luxury without compromise and built to enjoy not maintain. The exterior features NuCedar synthetic cedar shake siding, maintenance-free porch decking, colonial stone walls, irrigation, a rear patio with propane hookup, and a 24kW whole-house Generac generator. Inside, soaring 30-foot ceilings framed by magnificent timber beams, celestial windows, white oak floors, custom lighting, loft, 2 story stone fireplace create an unforgettable first impression. The designer kitchen offers quartz countertops, custom cabinetry, GE Caf appliances, and premium finishes. A first-floor primary suite with cathedral tongue-and-groove ceilings provides a peaceful retreat, complemented by high-efficiency HVAC, motorized skylights, epoxy-coated basement floors, and an oversized carriage-style garage. An extraordinary blend of architectural beauty, privacy, and one of coastal RI's most desirable lifestyles.

18 Fallon Trail, Westerly

Listing courtesy of Seaport Real Estate Services. Contact:

325 Post Road, Westerly
$3,500,000
5 Beds ⋅ 7 Baths
Perched 150 feet above sea level on one of Westerly's highest elevations and views of Block Island the Odiseya Estate is a 4.73-acre coastal sanctuary where Mediterranean grandeur meets rugged New England beauty. Centered around a meticulously renovated 4,300-square-foot villa, this private retreat offers an unparalleled blend of artisanal craftsmanship and modern sustainability. Inside, the home features luminous Venetian plaster walls, soaring cedar cathedral ceilings, and rich cherry and teak flooring. The gourmet kitchen boasts custom Amish cabinetry and an authentic wood-fired stone pizza oven, creating an unforgettable setting for culinary gatherings. A luxurious primary suite serves as an intimate sanctuary, complete with a private balcony for sipping morning coffee while taking in distant water views and ocean breezes. Updated with triple-pane windows and high-efficiency systems, the villa ensures exceptional comfort in every season. Outdoors, the estate unfolds into both an active recreational haven and a working agricultural paradise, featuring a private tennis court, a heated greenhouse, and a thriving orchard with over fifty fruit trees and active honeybee hives. Located just minutes from the world-class beaches, shops, and dining of Watch Hill, Odiseya Estate stands as an extraordinary coastal sanctuary, an eco-luxury haven, or a lucrative turn-key opportunity for a premier Airbnb rental.

325 Post Road, Westerly

Listing courtesy of William Pitt Sotheby's Int'l. Contact:

2 Olive Grove Lane, Westerly
$1,189,000
4 Beds ⋅ 3 Baths
Welcome to this stunning 2019 Colonial! Perfect for entertaining and day-to-day living, this home offers a bright, open floor plan featuring a spacious kitchen with a large center island, granite countertops, and beautiful hardwood floors throughout. The kitchen seamlessly flows into the inviting living room with sliders that open directly onto the rear deck and private backyard. Upstairs, the primary suite features a walk-in closet and a full private bath, complemented by three additional bedrooms and a full guest bath. Additional comforts include two-zone central A/C and gas heat, along with a 2-car attached garage. The outdoor oasis is designed for relaxation and gatherings, complete with a front porch, a pergola, a hot tub, meticulous gardens, a huge fire pit, and ample parking. Enjoy your own private pickleball court with an adjoining entertaining area and stairs leading to the top of the hill with seasonal winter water views. A versatile 1,020 sq. ft. detached outbuilding/ADU includes a workshop, separate utility structure with a new roof, and its own public water connection ideal for a guest suite, workshop, or ultimate family hangout. Tucked away in a peaceful, secluded setting near Shelter Harbor Golf Course, local beaches, and shops, where you can relax and watch local wildlife right from your yard. Main house is serviced by well water with a whole-house filtration system.

2 Olive Grove Lane, Westerly

Listing courtesy of RE/MAX South County. Contact:

22 South Drive, Westerly
$850,000
3 Beds ⋅ 3 Baths
Custom-Built Home with Exceptional Indoor & Outdoor Living. Welcome to this beautifully designed custom home, set on a spacious .34-acre lot and ideally located for both year-round living and summer enjoyment. Offering three bedrooms and two-and-a-half baths, this thoughtfully designed home features a desirable first-floor primary suite and an open, spacious layout. The inviting living room is highlighted by a dramatic cathedral ceiling and gas fireplace, creating a comfortable and welcoming gathering space. A formal dining room with hardwood flooring flows seamlessly into the bright, eat-in kitchen, making entertaining and everyday living effortless. Sliding doors lead from the main living area to a charming sunroom and rear deck, overlooking the private backyard. Beautiful natural stone walls add character and enhance the property's outdoor appeal. The second floor offers two additional bedrooms, a full bath, and an exceptionally large den/office, providing flexible space for a home office, guest area, media room, or additional living space. Additional features include a two-car garage, whole-house generator, sprinkler system, central air conditioning, and oil heat. Conveniently located near the hospital and just minutes from area beaches, this home offers the ideal combination of comfort, convenience, and versatility. Whether you're looking for a peaceful year-round residence or the perfect summer retreat, this custom home is ready to welcome you.

22 South Drive, Westerly

Listing courtesy of RE/MAX South County. Contact:

14 Mary Lou Avenue, Westerly
$1,250,000
4 Beds ⋅ 4 Baths
This custom built home offers 4 bedrooms and 4 baths. As you enter into the foyer you will see a vaulted ceiling with beautiful finish work and a staircase leading to the 2nd floor to the right and a 1st floor bedroom or office with a full bath just outside the door to the left. Down the hallway there is an open kitchen, living and dining area. Gorgeous, gleaming hardwood floors throughout. . Center island in the kitchen with gas cook top, double ovens, refrigerator, dishwasher and microwave. Solid wood cabinets and pantry closet. Then into the laundry room. Across the way is a beautiful formal living room/sunroom with a door to the rear deck and patio area. Beautiful antique mantle above the fireplace in the living room , then onto the primary bedroom with tray ceilings, full bath with tile floor, heated towel bar, large soaking tub and separate shower. Upstairs has 2 bedrooms, 1 bath, a family room or office area with balcony overlooking the Pawcatuck river. There is a large storage area that could be finished into extra square footage should you need more living area. The lower level has a large family room and full bath with a walk out door to side yard. And the remaining space is storage and mechanicals. There is a 2 car garage, outside shower and beautiful landscaping. City water and sewer and propane for heating along with central air. This one is a beauty and one you should not miss.

14 Mary Lou Avenue, Westerly

Listing courtesy of Coldwell Banker Coastal Homes. Contact:

377 Atlantic Avenue, Westerly
$4,395,000
4 Beds ⋅ 3 Baths
Close your eyes and imagine your dream beach house. Breathe in the salt air. Listen to the rhythmic sound of waves breaking along the shore. Take in the panoramic views from Block Island to Long Island and watch boats drift across the distant horizon. Now open your eyes and make that dream a reality in this spectacular oceanside retreat. Situated on Misquamicut's famous five-mile stretch of uninterrupted sandy beach, you can walk to one of the many shoreline venues for dining or cocktails. Completed in 2026 by Tier1 Construction, this home blends coastal elegance with modern craftsmanship and superior shoreline engineering. The main level features an open concept plan anchored by a dramatic floating staircase and a state-of-the-art kitchen with quartz counters, custom cabinetry, and premium stainless appliances. Dine in elegance with panoramic ocean views. The living area flows to an expansive deck for seamless indoor-outdoor living. Shiplap Paneling and White Oak floors add warmth and texture. A private guest suite with full bath and pocket door completes the main level. The luxurious Master suite offers a sitting area, full bath with multi head shower, walk in closet, laundry and a private balcony. Two additional bedrooms share a full bath and enjoy Salt Pond vistas. The ground level provides a two-car garage, generous storage, and elevator access to all floors. Everything you've always wanted in a beach house is waiting for you. Start living the Salt Life today.

377 Atlantic Avenue, Westerly

Listing courtesy of REMAX Revolution. Contact:

111 Avondale Road, Westerly
$6,950,000
4 Beds ⋅ 5 Baths
Nestled on Colonel Willie Cove in the heart of Avondale, this extraordinary waterfront residence is a masterclass in luxury coastal living. Surrounded by professionally designed landscaping w/ a private tidal channel bordering the property, every square inch has been thoughtfully curated to maximize the connection to the water, natural light, & outdoor living. Offered fully furnished & professionally designed by Watson Elsberry Designs, the home feels straight from the pages of a coastal design magazine. Impeccably finished across 3 levels, the residence blends sophisticated craftsmanship w/ warm, livable elegance. Walls of glass, multiple balconies, a trellised deck, enclosed sunroom, & expansive gathering spaces create seamless indoor/outdoor living w/ water views from nearly every room. The main level showcases a stunning chef's kitchen open to expansive dining & living areas designed for entertaining, while separate family rooms & private guest suites provide exceptional flexibility for multi-generational living or hosting. The upper-level primary suite is a true retreat w/ panoramic water views, spa-inspired bath, & custom walk-in closet. Luxury amenities include geothermal heating, whole-house generator, curated furnishings, & a 2-car garage. Located within the Watch Hill Fire District, just minutes to both historic Watch Hill & downtown Westerly, Rhode Island, this is a rare high-end offering tailored for the buyer seeking a turnkey luxury waterfront lifestyle.

111 Avondale Road, Westerly

Listing courtesy of Schilke Realty. Contact:

88 Old Post Road Unit 6, Westerly
$349,000
2 Beds ⋅ 1 Baths
Welcome to your Westerly retreat! Less than two miles from Weekapaug and Atlantic Avenue and close to Westerly's popular summer attractions, this updated, move-in-ready cottage offers an ideal combination of location, convenience, and flexibility. Offered furnished, this standalone unit is ready to enjoy from day one whether you're looking for a year-round residence, weekend getaway, or income-producing investment. Completely renovated from top to bottom, the home features a bright, modern interior with hardwood floors throughout, energy-efficient updates, and an open layout that makes excellent use of every square foot. Small in size but big on appeal, the home feels comfortable, stylish, and surprisingly spacious. Enjoy the ease of condo living with the privacy of a standalone home. Unlike a traditional condominium. The homeowners association handles lawn maintenance, leaf cleanup, and snow removal, allowing you to spend more time enjoying Westerly and less time on upkeep. Monthly fees also include septic and town water, helping simplify ongoing expenses. Residents also enjoy access to a large shared field for recreation and community use. The property has a strong rental history and has previously been operated as a short-term rental. The seller can provide a prior guest list upon request. Turnkey, furnished, low-maintenance, and close to the beach this is a rare opportunity to own your own Westerly retreat.

88 Old Post Road Unit 6, Westerly

Listing courtesy of Century 21 Guardian Realty. Contact: 401-515-5531

5 Water's Edge Road, Westerly
$14,200,000
6 Beds ⋅ 7 Baths
Here is the property you have been waiting for! Featuring an extraordinary waterfront setting, this legacy coastal estate offers thrilling sunsets, exceptional privacy and timeless architecture. A private deep-water dock and two moorings set the stage for sunset sails! Outdoor, a beautiful yet private in-ground pool with a pool house and the waterfront bluestone terrace provides ample areas for large scale entertaining and dining. Set on a secluded lane, this property offers a rare sense of tranquility without sacrificing convenience. Sea breezes and views create an atmosphere of remarkable peace and privacy yet steps away from the village of Watch Hill. The home's location is outside the flood zone; house has a recently updated elevation certificate. Designed for gracious living, the residence offers 6 bedrooms, and office, 5 full baths, and 2 powder rooms and a lower level play room and wine cellar. Of its 13 principal rooms, 11 enjoy captivating water views! Inside, a welcoming foyer, gracious living and dining rooms, a spacious kitchen, a sunroom with bar and an all-season sitting room serves as an oceanfront observatory. From the third story, steps lead to the rooftop deck with stunning views of Fisher's Island and Stonington! Above the garage is an office or den. Every detail of this property has been thoughtfully composed to celebrate its remarkable setting while delivering the comfort, privacy, and effortless elegance that define the very heartbeat of coastal living.

5 Water's Edge Road, Westerly

Listing courtesy of Mott & Chace Sotheby's Intl.. Contact:

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IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed. © 2026 State-Wide Multiple Listing Service. All rights reserved. Data Last Updated:

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