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25 Captains Drive, Westerly
$719,000
2 Beds ⋅ 3 Baths
OPEN HOUSE SATURDAY 10/31, 11AM-12PM. Offering the feel of a single-family home with the ease of condo living, this beautifully updated 2BR, 2.5BA townhome in coveted Captain's Watch Condominiums is a rare find! The true showstopper is the spectacular private backyard oasis, an exceptionally private retreat featuring an expansive stone patio, lush lawn, mature trees & beautifully landscaped grounds. Whether entertaining guests, dining alfresco or simply unwinding in the peaceful surroundings, this outdoor sanctuary offers a level of privacy rarely found in condo living. Inside, stylish finishes & inviting living spaces create a warm, welcoming atmosphere. A comfortable living room features a handsome stone fireplace, while the beautifully appointed kitchen boasts white cabinetry, granite countertops, stainless appliances & a breakfast bar. A sun-filled dining area overlooks the picturesque grounds with sliding doors opening to the patio, seamlessly connecting indoor & outdoor living. A stylish half bath & convenient laundry complete the main level. Upstairs, the spacious primary suite features a beautifully renovated bath with tiled walk-in shower & an adjoining versatile space ideal for a variety of uses. A generous 2nd bedroom with its own full bath provides added comfort. Additional highlights include central air & an attached garage. Enjoy a short stroll to the Pawcatuck River & minutes to historic downtown Westerly, Watch Hill & beautiful beaches!

25 Captains Drive, Westerly

Listing courtesy of Schilke Realty. Contact:

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:

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
20 Winnapaug Road Unit B3, Westerly
$306,000
1 Beds ⋅ 1 Baths
OWN YOUR MIQUAMICUT BEACH GETAWAY WITH INCOME POTENTIAL Imagine having your own place in Miquamicut where you can spend summer weekends at the beach, walk to nearby restaurants, enjoy your own assigned parking, and still have the ability to generate rental income when you're not using it. This unique condotel opportunity offers the best of both worlds: a personal coastal retreat and an income-producing investment. Located within an easy walk of the beach, these residences offer beach parking and access rights, two assigned parking spaces, and trash included with MFD taxes. For the investment-minded buyer, projected cap rates exceed 10% on the four units currently available, providing an opportunity to enter the Misquamicut vacation market at an attractive price point. Buyers can choose the unit that best fits their goals or explore the opportunity to acquire multiple units. Whether you're looking for a summer getaway, a second home that helps offset its own expenses, or a dedicated vacation-rental investment, this is an opportunity to own in one of Westerly's most recognizable beach destinations. Walk to the beach. Walk to restaurants. Park at the beach. Generate income. Enjoy Miquamicut. Four units currently available. Inquire for individual pricing, projected income, expenses, and cap-rate information.

20 Winnapaug Road Unit B3, Westerly

Listing courtesy of Stanton Realty, Inc.. Contact:

20 Winnapaug Road Unit B6, Westerly
$299,000
1 Beds ⋅ 1 Baths
OWN YOUR MISQUAMICUT BEACH GETAWAY WITH INCOME POTENTIAL Imagine having your own place in Misquamicut where you can spend summer weekends at the beach, walk to nearby restaurants, enjoy your own assigned parking, and still have the ability to generate rental income when you're not using it. Unit B6 is a unique condotel opportunity, offering the best of both worlds: a personal coastal retreat and an income-producing investment. Located within an easy walk of the beach, these residences offer beach parking and access rights, two assigned parking spaces, and trash included with MFD taxes. For the investment-minded buyer, projected cap rates exceed 10% on the four units currently available, providing an opportunity to enter the Misquamicut vacation market at an attractive price point. Buyers can choose the unit that best fits their goals or explore the opportunity to acquire multiple units. Whether you're looking for a summer getaway, a second home that helps offset its own expenses, or a dedicated vacation-rental investment, this is an opportunity to own in one of Westerly's most recognizable beach destinations. Walk to the beach. Walk to restaurants. Park at the beach. Generate income. Enjoy Misquamicut. Four units currently available. Inquire for individual pricing, projected income, expenses, and cap-rate information.

20 Winnapaug Road Unit B6, Westerly

Listing courtesy of Stanton Realty, Inc.. Contact:

20 Winnapaug Road Unit B7, Westerly
$350,000
1 Beds ⋅ 1 Baths
OWN YOUR MISQUAMICUT BEACH GETAWAY WITH INCOME POTENTIAL. Imagine having your own place in Misquamicut where you can spend summer weekends at the beach, walk to nearby restaurants, enjoy your own assigned parking, and still have the ability to generate rental income when you're not using it. This unique condo-tel opportunity offers the best of both worlds: a personal coastal retreat and an income-producing investment. Located within an easy walk of the beach, these residences offer beach parking and access rights, two assigned parking spaces, and trash included with MFD taxes. For the investment-minded buyer, projected cap rates exceed 10% on the four units currently available, providing an opportunity to enter the Misquamicut vacation market at an attractive price point. Whether you're looking for a summer getaway, a second home that helps offset its own expenses, or a dedicated vacation-rental investment, this is an opportunity to own in one of Westerly's most recognizable beach destinations. Walk to the beach. Walk to restaurants. Park at the beach. Generate income. Enjoy Misquamicut. Four units currently available. Inquire for individual pricing, projected income, expenses, and cap-rate information.

20 Winnapaug Road Unit B7, Westerly

Listing courtesy of Stanton Realty, Inc.. Contact:

31 Butterfly Drive, Westerly
$879,900
2 Beds ⋅ 2 Baths
Welcome home to this beautiful stand-alone condo!! Butterfly Estates is ideally situated on 5 acres within minutes to beaches, downtown, train station, Westerly Hospital, fabulous eateries and shopping all on a quiet cul-de-sac. The minute you walk in the Brazilian cherry floors capture your eye with 9-foot ceilings throughout and large windows allowing plenty of natural light...this home offers crown molding, a lovely screened in porch to relax in, gas fireplace, a den perfect for home office, reading or extra guests. Primary suite has beautiful, coffered ceiling along with double walk-in closets, soaking jacuzzi style tub and tiled walk-in shower. The secondary bedroom is located on the other side offering plenty of privacy. Another amazing feature is the possibility for future expansion upstairs!! The 2-car garage leads into a mudroom with laundry and head downstairs to the large basement perfect for finishing or storing all your treasures!! Did I mention the location??

31 Butterfly Drive, Westerly

Listing courtesy of Coldwell Banker Coastal Homes. Contact:

140 High Street Unit 304, Westerly
$240,000
1 Beds ⋅ 1 Baths
Welcome to the Maples- A wonderful residence in the heart of Westerly! #304 is a bright 1 bedroom, 1 bath unit located on the 3rd floor of the building. Natural light abounds through multiple large windows spilling into the living space. Meticulous and clean! Gorgeous cherry wood cabinetry are featured in the kitchen. The spacious bedroom has double closets and tons of light. A washer/ dryer is conveniently located in the walk-in utility closet. Easy access is provided to the unit from the main entrance elevator. The parking lot has plenty of parking with extra spaces for visitors. Storage units are located in the lower level. Rental rules per rules and regulations as follows: "No member shall rent, let, lease or license for use of occupancy by others than the owners thereof except to persons for a thirty day term or more, who have first been approved in writing and the lease has been approved by the Maples Board of Directors. Owner must occupy unit for a limited time of 1 year before renting is allowed" A minute walk to attractions in downtown Westerly and the Amtrak train station. Move right in and start enjoying a carefree Westerly lifestyle!

140 High Street Unit 304, Westerly

Listing courtesy of BHHS New England Properties. Contact:

12 Canal Street Unit 206, Westerly
$345,000
1 Beds ⋅ 1 Baths
Wow! Fantastic, adorable 1-bath studio condos in downtown Westerly don't come around often! Have you been searching for the ultimate launchpad where your social life and low-maintenance living collide? This property is officially at the center of the universe! Step into a bright, cleverly optimized layout that proves you don't need Sheldon Cooper's IQ to maximize spatial efficiency. Perfectly engineered for comfort. The main living area features large windows that flood the space with natural light, a sleek kitchen setup ideal for whipping up your favorite takeout or home-cooked meals, and a modern, pristine full bathroom. It's the ultimate cozy retreat after a busy day though we can't promise anyone won't try to claim your exact spot on the couch! Located right in the heart of dynamic downtown Westerly, you are just steps away from local favorites: Park, Cafe's, Restaurants, breweries, shopping, theaters, gyms and train station. Whether you are looking for a carefree primary residence, a coastal getaway, or a smart investment property, this condo represents an incredibly rare opportunity. Leave the car keys behind and immerse yourself in the best nightlife, culture, and coastal living Rhode Island has to offer. Don't wait for a shifting of tectonic plates to miss out on this one. Schedule your showing today BAZINGA!!

12 Canal Street Unit 206, Westerly

Listing courtesy of Fantastic Real Estate & Invest. Contact:

319 Atlantic Avenue Unit 13, Westerly
$949,000
2 Beds ⋅ 2 Baths
Rare Oceanfront Condo in the Heart of Misquamicut Beach! Wake up to breathtaking sunrises and experience the very best of seaside living in this top-floor oceanfront condominium Located in an intimate six-unit association, this bright and open two-bedroom, two-bath residence offers spectacular 360-degree views of the Atlantic Ocean and Winnapaug Pond from every room. Designed to maximize its incredible waterfront setting, the home features four private balconies plus a back deck, providing endless opportunities to relax, entertain, or simply take in the panoramic coastal scenery. Step outside your back door for direct access to your private beach, or enjoy the association's indoor pool and hot tub after a day on the sand. Inside, the thoughtfully designed floor plan is filled with natural light and showcases a modern kitchen with granite countertops, stainless steel appliances, and seamless flow into the ocean-facing living and dining areas. Ideally situated within walking distance of Misquamicut's popular restaurants, caf s, and entertainment, this home offers the perfect combination of relaxation and convenience. The Misquamicut Fire District is a family-friendly beach community nestled between the prestigious coastal villages of Watch Hill and Weekapaug.

319 Atlantic Avenue Unit 13, Westerly

Listing courtesy of Lila Delman Compass. Contact:

44 Bay Street Unit B105/B205, Westerly
$2,500,000
2 Beds ⋅ 2 Baths
Townhouse 5 (Units B105/B205) - 44 Bay Street - a combined upper and lower level townhouse with two assigned covered parking spaces consisting of two bedrooms / two baths completely furnished residence located in the Bayside Building. it is a participating Villa Residence in the Ocean House Management Rental Program. Private upper and lower decks with direct sunset and ocean views overlooking Little Narragansett Bay, the Watch Hill Yacht Club, the Connecticut coastline, and centered in the historic village of Watch Hill. Owners who opt into the Rental Program by Ocean House Management the hospitality manager will have access to the Ocean House Resort Hotel amenities package when in occupancy , which includes their Atlantic Ocean private beach,restaurants, spa, gym, indoor lap pool, croquet court,and several dining experiences. WHP Property Manager, is located on-site of the gated community Full kitchen (electric range, refrigerator, microwave, oven, exhaust hood), dining area for 6, two full upper & lower level private bathrooms each with 6' tub and shower, Italian tile floors. Upper level living area with lower level - sleeping accommodations with one private Master Bedroom with king size bed, private en-suite full bath, and 9x16 private deck, and one double twin bed room with separate television. Located on Bay Street with unobstructed views with walking distance to local shops, historic Watch Hill Carousel, and three pristine beaches.

44 Bay Street Unit B105/B205, Westerly

Listing courtesy of WATCH HILL PROPERTIES. Contact:

38 Bay Street Unit W301, Westerly
$2,800,000
2 Beds ⋅ 2 Baths
A fully renovated two-bedroom, two-bath residence in the historic Watch Hill Inn, a Relais & Ch teaux property. This residence boasts a magnificent 12-by-32-foot outdoor deck furnished with chaise lounges and an outdoor dining table that seats six. Enjoy spectacular sunset and ocean views from the direct southwestern exposure overlooking Little Narragansett Bay and the Watch Hill Yacht Club, all from the heart of historic Watch Hill Village. Enjoy a fully equipped kitchen with an electric range, refrigerator, microwave, oven, and exhaust hood, dining area, two tiled full bathrooms, and a contemporary decorative fireplace in the living room. Accommodates up to 6 guests with 2 on-site parking spaces. An on-site property manager maintains the common areas of this gated community. It is fully furnished & participates in the Ocean House Rental Program. Participation is optional, allowing the owner to occupy the residence or generate rental income when it is not in use. Owners who participate in the program, operated by Ocean House Management as the hospitality manager, have access to Ocean House amenities during their stays. These amenities include a private Atlantic Ocean beach, spa, fitness center, indoor lap pool, croquet court, shuttle service, and several dining venues. Located on Bay Street, offering unobstructed views and is within walking distance of local shops, the historic Watch Hill Carousel, a famous ice cream shop, and three pristine beaches.

38 Bay Street Unit W301, Westerly

Listing courtesy of WATCH HILL PROPERTIES. Contact:

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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