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$875,000
2 Beds ⋅ 1 Baths ⋅ 1041035 MLS
Tucked away on the desirable West Side, this charming two-bedroom home offers privacy, comfort, and the relaxed lifestyle that makes Cherry Grove so special. The home features generous living and dining areas with an easy, open feel, along with two comfortable bedrooms. Outdoors, a private deck creates the perfect setting for entertaining, relaxing in the sun, or enjoying quiet summer evenings, complemented by a private outdoor shower. Ideally located just steps from the ocean, this inviting home offers the perfect combination of privacy and proximity to the beach. A wonderful opportunity to own your own piece of Cherry Grove and make it your personal Fire Island retreat.

200 Surf Walk, Cherry Grove
$995,000
3 Beds ⋅ 2 Baths ⋅ 1040771 MLS
Contemporary beach house featuring an inviting open-concept layout designed for easy, relaxed living. The bright and airy interior flows seamlessly into a modern, well-appointed kitchen, creating a comfortable space for both everyday living and entertaining. The grand primary bedroom is a wonderful private retreat, featuring sliding glass doors that open directly onto its own private deck—an ideal spot for morning coffee, quiet afternoons, or enjoying the ocean air. Ideally located just three houses from the beach, this home offers the perfect combination of style, comfort, and proximity to the ocean. Outside, a lovely garden and serene backyard setting create a peaceful, private atmosphere, perfect for relaxing, outdoor dining, and enjoying long summer days and evenings. A wonderful opportunity to own a stylish and tranquil beach retreat just steps from the ocean.

101 Greene Avenue, Cherry Grove
$875,000
2 Beds ⋅ 1 Baths ⋅ 1036541 MLS
Tucked away on the desirable West Side, this charming two-bedroom home offers privacy, comfort, and the relaxed lifestyle that makes Cherry Grove so special. The home features generous living and dining areas with an easy, open feel, along with two comfortable bedrooms. Outdoors, a private deck creates the perfect setting for entertaining, relaxing in the sun, or enjoying quiet summer evenings, complemented by a private outdoor shower. Ideally located just steps from the ocean, this inviting home offers the perfect combination of privacy and proximity to the beach. A wonderful opportunity to own your own piece of Cherry Grove and make it your personal Fire Island retreat.

200 Surf, Cherry Grove
$975,000
3 Beds ⋅ 2 Baths ⋅ 1036096 MLS
A quintessential Cherry Grove cottage, cozy and unfussy, perfect for a relaxing beach vacation. There are three bedrooms and two bathrooms (the primary bedroom is en suite), Entertaining is easy with the kitchen open to the living area as well as the dining area. And the house features a spacious deck for outside dining, sunbathing, and lounging by the pool. Refresh yourself with an invigorating outdoor shower. Located in a quiet neighborhood, but still convenient to the nightlife and restaurants, the beach is just 4 houses off the beach, as is the trail through the Sunken Forest. The heated pool completes this lovely property.

259 East Walk, Cherry Grove
$775,000
2 Beds ⋅ 1 Baths ⋅ 1035396 MLS
Discover the timeless charm of this delightful cottage, tucked away on an oversized, private lot where peace and tranquility surround you. This quiet retreat offers the perfect blend of seclusion and classic Cherry Grove character. Inside, you'll find two comfortable bedrooms, a full bath, and a sleeping loft that provides additional space for guests. An indoor washer and dryer add everyday convenience, while the inviting interior captures the warmth and simplicity of a true beach cottage. Whether you're seeking a serene weekend escape or a place to create unforgettable summer memories, this quaint hideaway is full of character and possibilities. Rarely does a property with this much privacy and charm become available. A true Cherry Grove gem waiting to be yours.

86 Gerard Walk, Cherry Grove
$875,000
2 Beds ⋅ 1 Baths ⋅ 1025002 MLS
This beautifully maintained Cherry Grove home offers the perfect combination of comfort and style. Step inside to discover beautiful wood flooring throughout, soaring vaulted ceilings, and an abundance of natural light from the skylight and thermal double-pane windows. The inviting living room features a wood-burning fireplace, creating the perfect atmosphere for cozy evenings in every season. The updated kitchen and bathroom showcase granite countertops, new appliances, and modern finishes designed for effortless living. This adorable cottage includes central air conditioning and heat, and a newly insulated crawl space with heat tracing for added efficiency and peace of mind. Outdoor living is just as impressive, with two spacious decks ideal for entertaining, dining, or relaxing in the sun. Additional features include a hot and cold outdoor shower, privacy fencing, and a large cedar storage shed. Inside, you’ll appreciate the washer and dryer, large closets, and a loft for additional storage, providing plenty of room for all your beach essentials. Whether you’re searching for a weekend retreat, a summer getaway, or a home to enjoy throughout the summer and then some, this exceptional Cherry Grove property is ready to welcome you. Features Include: Beautiful wood floors throughout Central air conditioning and heat for year round comfort Wood-burning fireplace Thermal double-pane windows Newly insulated under-house area with heat tracing Updated kitchen and bathroom Granite countertops New appliances New decking Two large outdoor living spaces Vaulted ceilings Skylights Large outdoor cedar shed Loft storage Large closets Washer and dryer Hot and cold outdoor shower Privacy fencing This home is a rare opportunity to own a thoughtfully updated, move-in-ready property in the heart of Cherry Grove

169 Main Walk, Cherry Grove
$4,850,000
4 Beds ⋅ 4 Baths ⋅ 1021398 MLS
We are proud to introduce Crest House, one of Cherry Grove's most extraordinary oceanfront estates. Commanding 120 feet of direct Atlantic Ocean frontage on a rare double lot spanning 0.37 acres. Built in 2012 and maintained with meticulous attention to detail, this 7,130 square foot post-and-beam residence rises three stories above the dunes and delivers an unmatched Fire Island living experience. Four bedrooms, three full baths, a powder room, soaring vaulted ceilings, three fireplaces, and a fully furnished interior make this a true turn-key retreat. The open-plan main level flows seamlessly into over 4,700 square feet of outdoor living - expansive decks, a heated pool, covered porch, and private courtyard - all framed by endless ocean views. Central air, forced air heat, and four zones of climate control ensure comfort in every season. Car-free Cherry Grove offers the rarest combination of privacy and community on the East End. Exit the ferry and enter a world where you're surrounded by nothing but the sounds of the ocean and the breeze. Properties of this caliber - this size, this position, this craftsmanship - simply do not come to market often.

55 Lewis Walk, Cherry Grove
$2,500,000
4 Beds ⋅ 5 Baths ⋅ 1017237 MLS
Brand New Oceanfront Home with Pool! This stunning newly constructed residence offers the perfect blend of luxury, comfort, and breathtaking natural beauty. Featuring four spacious bedrooms, including two private primary ensuite retreats, and three-and-a-half beautifully appointed bathrooms, the home is designed for effortless coastal living. The bright and airy open-concept living, dining, and kitchen area is ideal for entertaining, with seamless indoor-outdoor flow and spectacular water views. Step outside to enjoy the fabulous new swimming pool and stylish cabana, creating your own private resort by the sea. Crowning this exceptional property is an expansive roof deck showcasing panoramic vistas of both the Atlantic Ocean and the Great South Bay—an unforgettable setting for sunrise coffee, sunset cocktails, and stargazing. A rare opportunity to own a brand-new oceanfront sanctuary in an incomparable location.

52 Lewis Walk, Cherry Grove
$1,750,000
7 Beds ⋅ 8 Baths ⋅ 1017133 MLS
Wisteria is a one-of-a-kind luxury retreat in Cherry Grove, Fire Island, completely rebuilt in 2020. This exceptional property features seven private en-suite bedrooms, including two poolside suites, a stunning open-concept living area with chef’s kitchen, and resort-style amenities throughout. Enjoy a solar-heated pool, meditation garden, covered outdoor dining pavilion, and a separate studio with full bath. The spectacular rooftop deck offers panoramic views from the Atlantic Ocean to the Great South Bay. A rare opportunity to experience the ultimate in Fire Island luxury and privacy

37 Bayview Walk, Cherry Grove
$1,350,000
4 Beds ⋅ 2 Baths ⋅ 1015727 MLS
This is truly a one-of-a-kind opportunity! An extraordinary, expansive ocean front property in Cherry Grove, featuring a rare double lot with stunning ocean frontage. It has never been offered before, and the possibilities here are truly endless. What sets this property apart is the land itself and the boundless potential it holds. A great location on the East end of the Grove, perched atop a high dune with breathtaking ocean views. This oceanfront home offers a rare opportunity to own a piece of timeless charm. Lovingly built in the early 1950s and maintained by the same owners for generations, this unique property is simply a must-see. Four spacious bedrooms, including a primary bedroom on the main floor and three additional bedrooms on the lower level. 1.5 bathrooms plus the added convenience of an outdoor shower perfect for rinsing off after a day at the beach. The main Floor is designed with the open-concept: living, dining, and kitchen areas creating a seamless flow for entertaining or enjoying quiet moments.

54 Lewis Walk, Cherry Grove
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 1014328 MLS
Experience coastal living at its finest in this exceptional 3-bedroom, 3-bathroom home featuring stunning bay views from multiple levels and some of the most breathtaking panoramas in Cherry Grove. Relax on the spacious rear deck as you watch ferries glide across the bay and enjoy the ever-changing waterfront scenery. The primary suite opens to a charming Juliette balcony, offering a private retreat with picturesque bay views. For truly unforgettable sunsets and sweeping water vistas, the rooftop deck provides one of the area's most spectacular vantage points. The first floor features a bright, open-concept layout designed for effortless entertaining, with a spacious living room, dining area, and well-appointed kitchen, all accented by beautiful hardwood floors. This level also includes a comfortable guest bedroom, a full bath, and a convenient laundry/utility room. On the second floor, the primary suite offers a private en suite bath and direct access to the Juliette balcony overlooking the bay as well as a 3rd bedroom. At the top of the spiral staircase is a third full bath, along with a versatile loft-style space featuring a desk area and room for a pull-out sofa, creating additional sleeping accommodations for guests or work space. With its thoughtfully designed layout, multiple outdoor living spaces, and spectacular bay views from nearly every level, this remarkable home offers the perfect blend of comfort, style, and waterfront charm.

118 Bayview Walk, Cherry Grove
$1,645,000
3 Beds ⋅ 3 Baths ⋅ 1011905 MLS
Timeless Waterfront Retreat on the Great South Bay - Steeped in history and dating back to circa 1909, this exceptional waterfront home offers a rare opportunity to own a truly special property with a rich and storied past. Nestled along the shores of the Great South Bay, the residence features 3 bedrooms and 2.5 bathrooms, showcasing breathtaking sunset views and the unique charm of watching the ferry arrive each day. Beautifully remodeled while preserving its historic character, the home boasts gleaming hardwood floors, a stunning fieldstone fireplace, central air conditioning, satellite TV, and high-speed Wi-Fi. The inviting interior blends classic elegance with modern comfort, creating an ideal setting for year-round living or a seasonal escape. Outside, enjoy a heated swimming pool surrounded by mature gardens and established plantings that provide beauty and privacy. Additional amenities include an enclosed outdoor shower and a separate washer/dryer shed, enhancing the relaxed waterfront lifestyle. Offering unmatched scenery, character, and comfort, this remarkable property is a rare gem on the Great South Bay.

209 Bayview Walk, Cherry Grove
$799,000
4 Beds ⋅ 1 Baths ⋅ 1010527 MLS
Tucked away in the west end of Cherry Grove, 236. Sea Walk offers the perfect blend of privacy, charm and natural beauty. Situated on one of Cherry Grove‘s, most peaceful and picturesque walks this queen cottage is surrounded by lush, landscaping and serene outdoor spaces that capture the essence of Cherry Grove living. Inside the home features four bedrooms, one full bathroom and an open floor plan concept that creates a comfortable and inviting atmosphere for entertaining and relaxing. A wood-burning stove serves as the centerpiece of the living area.

236 Sea Walk, Cherry Grove
$795,000
2 Beds ⋅ 2 Baths ⋅ 996848 MLS
Charming original cottage situated directly on the Great South Bay, featuring two bedrooms and two full bathrooms, plus an outdoor shower and ample space for a large pool. The open-concept living and dining area boasts vaulted ceilings and a cozy fireplace, creating a bright and inviting atmosphere. The primary bedroom features sliding glass doors that open directly onto the bayside deck, offering stunning water views and easy outdoor access. Additional highlights include an updated kitchen, an indoor washer and dryer, and a spacious corner lot. This unique waterfront property combines classic cottage charm with modern conveniences, making it the perfect bayside retreat.

71 Bayview Walk, Cherry Grove
$1,200,000
4 Beds ⋅ 2 Baths ⋅ 986343 MLS
"Valhalla" on lovely Doctor's Walk in Cherry Grove. This charming four bedroom encompasses all the amenities of a fine summer home. Large living room with wood-burning fireplace, two large master bedrooms with vaulted ceilings, large galley kitchen and wonderful solarium with views of the "English" garden and pond which has a collection of various types of lilies, seedum and ivy. Roof deck for evening sunsets and a deck with a charming gazebo complete this exceptional home. AND, just 4 houses off the beach!!

146 Doctors Walk, Cherry Grove
$1,350,000
7 Beds ⋅ 7 Baths ⋅ 971902 MLS
Welcome to an exceptional opportunity in the heart of Cherry Grove, where spacious accommodations, outstanding outdoor living, and breathtaking Great South Bay views come together in one remarkable three-story property. Featuring 7 bedrooms and 6½ baths, this generously proportioned home offers an ideal combination of privacy, comfort, and entertaining space. Whether envisioned as a private vacation retreat, an investment property, or a high-demand rental opportunity, the home's versatile layout provides ample room for family and guests to gather while still offering plenty of space to unwind. The top-floor living level is the true showpiece of the residence, offering spectacular views of the Great South Bay through its elevated vantage point. A wraparound balcony extends the living space outdoors, creating an exceptional setting for morning coffee, sunset cocktails, entertaining, or simply enjoying the distinctive beauty of the surrounding landscape. Inside, the upper level features soaring ceilings and tile floors, creating an open, airy atmosphere. A wood-burning stove adds warmth and character, while the dedicated media room provides an inviting space for movie nights, watching the game, or relaxing with family and friends. The combination of expansive living areas, high ceilings, abundant outdoor space, and panoramic water views makes this level particularly well suited to entertaining. The home includes a spacious primary suite, along with six additional bedrooms, providing substantial flexibility for hosting guests, accommodating extended family, or maximizing rental potential. With 6½ baths, the property is exceptionally well equipped for larger groups and extended stays. Outdoor living is equally impressive. Multiple decks provide numerous areas for dining, lounging, and entertaining, while the property's fully fenced grounds offer added privacy and security. An outdoor shower provides a welcome convenience after a day at the beach, allowing everyone to rinse off before returning indoors. Additional storage and utility sheds offer practical space for gardening equipment, beach gear, and seasonal belongings. Location is another defining feature. The property is situated just steps from Cherry Grove's vibrant town center, placing restaurants, shops, nightlife, and the community's lively atmosphere within easy reach. At the same time, the home is conveniently located near one of New York's most beautiful ocean beaches, making it easy to enjoy long beach days, swimming, sunbathing, and the natural beauty of the barrier island. An outstanding choice for investment, vacation living, or rental income potential, this distinctive property offers the space and location to make the most of the Cherry Grove lifestyle. OneKey MLS #971902 This property is also available thru D.Katen Fire Island Properties.

154 Doctors Walk, Cherry Grove
$1,725,000
4 Beds ⋅ 4 Baths ⋅ 965259 MLS
Spacious OCEANFRONT home - This is a fantastic opportunity to own a well-maintained property in on the Ocean in Cherry Grove. The listing features modern amenities, spacious living areas, and is move-in ready! Great investment opportunity. Don’t miss your chance to make this wonderful space yours! It has Open living/dining room with amazing views of the Atlantic Ocean. Two floors, four bedrooms, four full bathrooms, air-conditioning, cathedral ceilings. Gorgeous plunge pool and hot tub surrounded by mahogany decks - fenced for privacy

300 Lewis Walk, Cherry Grove

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