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$1,075,000
2 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 2 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:

$1,780,000
3 Beds ⋅ 3 Baths
Experience Misquamicut Beach living with this lovely home set on over an acre of prime coastal land. Located between the exclusive enclaves of Watch Hill and Weekapaug, this home offers breathtaking, panoramic views of the 476-acre Winnapaug Pond and its serene marshlands, which stretch toward the breach way to the Atlantic Ocean. Whether you're launching a kayak from your backyard path or enjoying the private access to Misquamicut Fire District beaches, this is a water-lover's paradise. Inside, the home is bathed in natural light across three expansive levels. The main floor features an open-concept layout centered around a 2024-renovated kitchen, complete with an 8-foot island and a dedicated wine/coffee bar. Step out onto the full-length deck to take in explosive water views. This level also includes two comfortable bedrooms and a full bath. The upper-level primary suite is a true sanctuary, featuring vaulted ceilings, a private sunrise deck, and a charming "captain's nook" perfect for children. The ground-level walkout provides a third bathroom, two flexible office spaces, and a two-car garage. With a brand-new roof (2026), updated siding, mini-splits, new furnace, irrigation system and a strong rental history, this home is as much a smart investment as it is a dream retreat.

408 Atlantic Avenue, Westerly

Listing courtesy of Lila Delman Compass. Contact:

$18,775,000
6 Beds ⋅ 8 Baths
Rarely does an estate of this caliber become available in the heart of Watch Hill. Privately set on 15 extraordinary acres, this 6-bedroom, 7 full and 1 half bath residence offers unparalleled privacy, breathtaking water views, and timeless architectural character. Designed to capture sweeping vistas of Block Island, Montauk, Long Island, and the Misquamicut Golf Course, the home seamlessly blends historic craftsmanship with modern coastal living. Distinctive features include reclaimed architectural elements, stained and leaded glass, cypress ceilings, imported stone and tile finishes, and an octagonal study inspired by classic Watch Hill architecture. Multiple gathering spaces throughout the home create an ideal setting for both grand entertaining and intimate living. The resort-style outdoor amenities are equally impressive, featuring a pool and spa with waterfall, pool cabana with full bath and changing area, two fenced gardens, and a fully equipped outdoor kitchen. The expansive grounds provide a rare sense of seclusion while remaining moments from all that Watch Hill has to offer. A truly exceptional coastal estate where land, views, privacy, and craftsmanship converge to create one of Southern Rhode Island's most remarkable offerings.

18 E Hills Road, Westerly

Listing courtesy of Flagship Real Estate Advisors. Contact:

$1,425,000
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:

$12,650,000
6 Beds ⋅ 8 Baths
Extraordinary Watch Hill Estate -- Where Modern Luxury Meets Timeless Elegance. This extraordinary estate seamlessly overlays a 2026 custom-built modern luxury home onto the timeless character of the original 1890 built Lion Gate Inn, providing the perfect balance of contemporary sophistication and history. Set in the heart of Watch Hill and positioned on 1.45 impeccably landscaped acres in one of the area's most coveted neighborhoods, the property offers the rare combination of privacy and proximity, just under a mile from vibrant Bay Street and an easy walk to East Beach. Spanning an impressive 7,442 square feet, the home showcases a refined open floor plan designed for both grand entertaining and comfortable everyday living. A dramatic double-height entry with 10 to 12- foot ceilings sets the tone, while expansive floor-to-ceiling windows bathe the interiors in natural light, highlighting the home's clean lines and contemporary elegance. At the heart of the home is a chef's kitchen outfitted with top-tier appliances. The residence offers exceptional flexibility with two luxurious primary suites located on both the first and second floors, complemented by three spacious double bedrooms designed for family living. The walk-out lower level is a destination of its own, featuring a state-of-the-art media room, a beautifully appointed wine cellar, a full laundry area, and a private guest suite. Every detail of this spectacular home has been crafted to the highest standard.

4 Foster Cove Road, Westerly

Listing courtesy of Residential Properties, Ltd.. Contact:

$2,650,000
3 Beds ⋅ 3 Baths
This custom-built Contemporary home designed by the world-famous Centerbrook Architects offers an exclusive retreat in the gated No Bottom Pond community. Highlights include open space, 2 tennis courts, and protected privacy by a small hill with a stone terrace and fire pit to take in the beautiful starry night sky. With 3 bedrooms, 2.5 baths, plus 3,213 sq. ft. of living space on a sprawling 1-acre lot, this residence is an ideal coastal retreat! The living room, media room, dining room, and kitchen feature cathedral ceilings, while the soaring stone fireplace creates an inviting, open atmosphere. The primary suite & bath are secluded on the main level as well for ease and comfort. An integral 2- car garage includes water facilities adjacent to rough plumbing for a possible full 4th bath. Across the driveway find a large separate outbuilding with another 2-car garage, workspace, a loft, & storage area lending to another possible living space! The property is equally located between Westerly, with it's municipal facilities including a state run airport( jet accessible), an Amtrak train station, & 95, plus the quaint village of Watch Hill, with it's iconic shops & restaurants and of course beautiful beaches right on the Atlantic Ocean! Please make an appointment to see this very special offering.!

13 NO BOTTOM Ridge, Westerly

Listing courtesy of Residential Properties, Ltd.. Contact:

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