Bay Shore Homes with Pool

Bay Shore Homes with Pool

Welcome to Bay Shore, a vibrant community nestled in the heart of Suffolk County, New York. Known for its rich history and scenic waterfront, Bay Shore is not just a place to live; it’s a place to thrive. The Bay Shore School District is a cornerstone of this community, offering an exceptional education that prepares students for success. With a commitment to academic excellence and a wide array of extracurricular activities, the district fosters a nurturing environment where children can grow, learn, and explore their potential. Families are drawn to Bay Shore not only for its stellar schools but also for its close-knit community feel and beautiful surroundings.

For those seeking a home with a touch of luxury, Bay Shore offers a stunning selection of properties featuring private pools. Imagine relaxing in your own backyard oasis, enjoying sunny afternoons by the water, or hosting memorable gatherings with friends and family. Homes with pools in Bay Shore range from charming single-family residences to more expansive estates, each providing a unique blend of comfort and style.

Living in Bay Shore means enjoying the best of both worlds: a peaceful suburban atmosphere complemented by easy access to vibrant city life. With beautiful parks, waterfront views, and a variety of shopping and dining options, this area truly has something for everyone. Whether you’re a growing family or looking to retire in comfort, Bay Shore is the perfect place to call home. Discover the allure of Bay Shore and explore the homes with pools that await you in this delightful community!

Newest Bay Shore Homes with Pool

$2,595,000
5 Beds ⋅ 3 Baths ⋅ 1049697 MLS
The Ultimate Resort Home, Just Steps from the Beach 253 Cottage Walk | Ocean Beach, NY 11770 | Fire Island Just four houses from the beach, 253 Cottage Walk sits on an oversized 6,000-square-foot lot with a huge 438-square-foot L-shaped pool, spa, sauna, outdoor kitchen, and nearly 2,000 square feet of deck space. This spacious 4+ bedroom, 3-bath home is the perfect setting to enjoy all the beauty and entertaining Fire Island has to offer. The private, fully fenced and gated grounds create a secluded oasis, featuring the incredible L-shaped sports pool with a large sun shelf for lounging, a big 7' × 7' spa that seats up to 8, and a 4-person cedar sauna. A beautiful new modern outdoor shower and full cabana bathroom complete the retreat. Whether you're grilling at the outdoor kitchen or gathering around the 12-foot outdoor bar, this home has it all. A dedicated turf area gives the kids and the games a home of their own. Inside, the two-story home offers four bedrooms plus a den with large French doors and its own closet, ideal as a home office or additional sleeping space, and three fully renovated bathrooms. Two of the bedrooms feature private en-suite baths. The renovated kitchen features custom finishes, two pantries, and views to the pool through the sliding glass doors. Beautiful renovations throughout— new flooring, paint, fixtures, and finishes — capture its true Fire Island beauty. Comfort is ensured throughout an extended season with ductless mini-split systems providing zoned climate control in every room, and a dedicated laundry room adds everyday convenience. The home also features a classic cedar shake exterior and a low flood insurance premium. With tremendous decking wrapping the first floor, plus an upper deck with partial ocean views off the primary bedroom, there is no shortage of outdoor space for dining and lounging. With the beach just steps away, a resort-style pool, deck, and yard, partial ocean views, and completely renovated interiors, 253 Cottage Walk checks every box for a truly exceptional Fire Island home!

253 Cottage Walk, Ocean Beach
$799,999
5 Beds ⋅ 2 Baths ⋅ 1045316 MLS
Welcome to this beautifully maintained 5-bedroom, 2-bath home, lovingly cared for by the same owners for many, many years! This spacious and inviting property offers a wonderful combination of charm, comfort, and versatility, with part of the home currently utilized as an Airbnb, providing an excellent opportunity for additional income potential. Inside, you’ll find beautiful wood floors, crown molding, a cozy fireplace, central air, gas heat, and a bright, inviting sunroom perfect for enjoying your morning coffee or relaxing at the end of the day. The bedrooms are generously sized and the primary accommodates king-size furniture, while the large 'granny' attic offers abundant storage. Step outside to an amazing entertaining yard featuring a sparkling inground pool, spacious deck, and plenty of room for gatherings and summer fun. The large driveway provides ample parking, complemented by a garage for additional storage and convenience. Cedar-impression vinyl siding adds attractive curb appeal with easy maintenance. Ideally located less than a mile from Main Street and the railroad station, and close to the Fire Island ferries, hospitals, shopping, dining, and transportation. Whether you’re looking for a spacious home, an entertaining oasis, or a property with income-producing potential, this well-loved home offers it all!

73 Maple Avenue, Bay Shore
$3,500,000
3 Beds ⋅ 4 Baths ⋅ 1045873 MLS
Set directly on the Atlantic in the coveted low 400s of Fire Island Pines, this contemporary oceanfront residence combines exceptional beachfront living with modern construction and year-round functionality. Built from the ground up in 2016 to post-Hurricane Sandy elevation and building standards, the fully permitted home offers three ocean-facing en-suite bedrooms, 3.5 baths, a heated saltwater pool, rooftop hot tub and private beach access via its own boardwalk. The open main living level features 11-foot ceilings, hardwood floors, expansive ocean-facing glass and a wood-burning fireplace. The kitchen is equipped with high-end appliances including a 36-inch refrigerator, gas range, wall oven, dishwasher, wine cooler and dedicated ice maker. Glass doors open directly to the oceanfront deck and heated saltwater pool, creating a seamless connection between the interior, outdoor living spaces and beach beyond. Upstairs, all three en-suite bedrooms enjoy ocean views and private balconies. Two are generously proportioned primary suites, while the rooftop terrace and hot tub offer panoramic views across the Atlantic and the Pines. Fully winterized with substantial heated storage beneath the home, recently replaced HVAC condensers and refinished hardwood floors. Extensively updated during the current ownership and offered fully furnished, excluding artwork. A turnkey oceanfront home designed for long summers, shoulder seasons and life in the Pines throughout the year.

418 Ocean Walk, Fire Island Pines
$1,599,000
6 Beds ⋅ 4 Baths ⋅ 1045401 MLS
Lovingly restored and thoughtfully enhanced by its current owners, this remarkable 1880 residence reflects years of careful stewardship And substantial investment. Every update was made to elevate everyday living while honoring the home's character and architectural integrity. Updates: 2021 : New Siding & Windows, New PVC & Aluminum Fencing. Leaf Filter on All Gutters 2021/2022 : Basement waterproofed ( Lifetime guarantee ) 2021/2022 : Pool heater & Filter 2022 : New Split Units 2023: Generator, 15 zone Sprinklers, Alarm system with 11 Cameras hooked up to Central Station, Doors 2024: New Kitchen & Appliances, Motorized Shades in Living Room 2025: New driveway, New walkway and Stoops 2026: 2.5 New Bathrooms, with Soaker tub on 2nd floor and wonderful shower on third floor 2026: Newly sealed bricks around pool and back walkway.

75 S Penataquit Avenue, Bay Shore
$1,695,000
4 Beds ⋅ 3 Baths ⋅ 1043341 MLS
Impeccably maintained, secluded Bay Walk property located eight minutes from the Waterfront. Renovated in 2025 including kitchen appliances; cabinetry; refinished hardwood floors; heated XL saltwater pool; hot tub; gas water heater; roof and fully serviced Andersen windows & doors. New furnishings throughout. Extensive mahogany decking. Wood burning fireplace and propane fire pit. Fully air conditioned. Generously proportioned primary en-suite features with additional fireplace. Three guest bedrooms (one king & two queen beds) with ample closets. Low operating expenses and $185k in 2026 gross rent; several weeks pre-booked in 2027. Straightforward mortgage financing – no open permits, violations, and conforming to zoning requirements. Being sold fully furnished & turnkey.

279 Bay Walk, Fire Island Pines
$1,650,000
3 Beds ⋅ 2 Baths ⋅ 1041244 MLS
Set amongst lush landscaping, 208 Midway Walk is a commanding presence with a storied history and architectural pedigree attributed to Bates Masi+ Architects. Cedar detailing inside and out presents 3 bedrooms and 2 full baths, double height ceilings and large windows bringing the indoors out. Extra deep lot and large pool + morning and afternoon decks, sun and shade options, makes for the ideal Fire Island retreat.

208 Midway Walk, Fire Island Pines
$2,000,000
9 Beds ⋅ 9 Baths ⋅ 1040354 MLS
Rare Waterfront Investment Opportunity On Penataquit Canal! This Exceptional Home Offers Over 180 Feet Of Prime Waterfront With 13 Private Boat Slips, Expansive Docking, And Breathtaking Views Of Fire Island. Situated At The End Of A Quiet Cul-De-Sac, This Unique Property Features A Total Of 9 Bedrooms And 9 Bathrooms, Including 5 Bedrooms With Private En-Suite Baths. Step Outside To A True Waterfront Oasis Featuring An In-Ground Pool With An In-Ground Hot Tub, A Stunning Brick Outdoor Kitchen, Expansive Paver Patio, And Swaying Palm Trees, Creating The Ultimate Resort-Style Setting For Entertaining Or Relaxing Along The Water. Whether You're Looking To Expand Your Investment Portfolio, Generate Exceptional Rental Income, Or Own A One-Of-A-Kind Waterfront Property With Endless Possibilities, This Incredible Offering Checks Every Box. A Rare Opportunity To Own A High-Income Producing Property In An Unbeatable Waterfront Location.

64 Mowbray Avenue, Bay Shore
$3,300,000
3 Beds ⋅ 3 Baths ⋅ 1038274 MLS
One of Fire Island Pines’ most recognizable residences, the Pyramid House is an extraordinary expression of the experimental modernism that came to define the Pines. Designed circa 1960 by Buenos Aires–born architect Julio Kaufman, the house was later thoughtfully reimagined while preserving Kaufman’s iconic silhouette. A monumental steel-and-glass wall opens the soaring upper-level great room to sweeping views across the protected dunes of Fire Island National Seashore toward the Atlantic and bay beyond. Set at the quiet eastern edge of the Pines and bordering protected landscape, the approximately 2,100-square-foot residence offers an unusual degree of privacy. Built to a standard uncommon to Fire Island, its robust construction includes galvanized structural steel designed to endure the island environment. The current configuration offers three bedrooms and two-and-a-half baths. The lower level is devoted principally to an expansive primary suite with dressing areas, bath and private study, opening toward the pool and dunes. Across the secluded courtyard, three smaller pyramidal forms echo the geometry of the original house, with two guest bedrooms flanking a central bath. Recent improvements include central air conditioning, significant electrical upgrades, a new saltwater pool liner and updated pool mechanicals, along with 3M Prestige 70 window film applied to the Pyramid’s monumental glazing. For its next steward, the expansive lower level presents the possibility of another chapter of reinvention, potentially accommodating two additional ensuite bedrooms and creating a five-bedroom, four-and-a-half-bath residence.* The property’s successful history as a sought-after seasonal rental adds another dimension to its versatility. More than six decades after its creation, the Pyramid House remains remarkably private and unmistakably iconic—a landmark of Fire Island modernism ready for its next chapter. *Any potential reconfiguration is subject to applicable approvals and independent verification by the purchaser.

443 Sail Walk, Fire Island Pines
$2,200,000
10 Beds ⋅ 7 Baths ⋅ 1037620 MLS
Step back in time and experience the grandeur of this extraordinary 1850 Victorian estate, a truly one-of-a-kind residence where timeless architecture, remarkable scale, and old-world craftsmanship create something rarely found today. Set on 1.64 breathtaking, park-like acres, this magnificent property offers exceptional privacy, an inground pool, and endless possibilities. From the moment you enter, soaring ceilings, intricate crown moldings, beautiful hardwood floors, and exquisite period details capture the elegance and charm of a bygone era. Three expansive floors of living space feature a magnificent living room, grand banquet-sized formal dining room, large eat-in kitchen, and an inviting den with fireplace. The main residence offers an impressive ten bedrooms, seven full baths, and a full basement, providing extraordinary space and versatility. The estate also features a separate back house offering four additional bedrooms, two full baths, and a two-car garage, adding another remarkable dimension to this unique property. Rich in history and overflowing with character, this exceptional Victorian estate presents a rare opportunity to restore, reimagine, and create something truly spectacular. From its grand interior spaces to its sprawling grounds and resort-style pool, this is more than a home. It is a piece of history waiting for its next chapter. Make this extraordinary one-of-a-kind estate yours.

45 S Penataquit Avenue, Bay Shore
$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
$2,000,000
1035730 MLS
Rare Waterfront Investment Opportunity On Penataquit Canal! This Exceptional Triplex Offers Over 180 Feet Of Prime Waterfront With 13 Private Boat Slips, Expansive Docking, And Breathtaking Views Of Fire Island. Situated At The End Of A Quiet Cul-De-Sac, This Unique Property Features A Total Of 9 Bedrooms And 9 Bathrooms, Including 5 Bedrooms With Private En-Suite Baths. Step Outside To A True Waterfront Oasis Featuring An In-Ground Pool With An In-Ground Hot Tub, A Stunning Brick Outdoor Kitchen, Expansive Paver Patio, And Swaying Palm Trees, Creating The Ultimate Resort-Style Setting For Entertaining Or Relaxing Along The Water. Whether You're Looking To Expand Your Investment Portfolio, Generate Exceptional Rental Income, Or Own A One-Of-A-Kind Waterfront Property With Endless Possibilities, This Incredible Offering Checks Every Box. A Rare Opportunity To Own A High-Income Producing Property In An Unbeatable Waterfront Location.

64 Mowbray Avenue, Bay Shore
$2,200,000
3 Beds ⋅ 3 Baths ⋅ 1033182 MLS
THE BEST THE PINES HAS TO OFFER. Gorgeous contemporary 2 bedroom, 3 bath offering seamless indoor/outdoor living. Private and luxurious the many amenities include a large heated pool & spacious deck, hot tub, central AC and heat, fireplace, television room that can be converted into a third bedroom & designer furnishings all set in beautifully landscaped gardens.

307 Shady Walk, Fire Island Pines
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