Browse All Islip City NY Properties with Pool for Sale

Charming Islip home with an incredible backyard oasis! This beautifully maintained property features gorgeous hardwood floors, a stunning custom kitchen with rich wood cabinetry, granite countertops, stainless steel appliances and oversized center island. Warm architectural details include crown molding, recessed lighting and stylish barn-door accents. The spacious bedrooms offers generous closet space. Outside, enjoy a private, lushly landscaped yard with a sparkling in-ground pool, huge garage, and an expansive paver patio - perfect for entertaining, relaxing and making summer memories. A truly special home in a desirable Islip location! Don't miss your chance to own a truly unique home.

60 Jaycox Avenue, Islip

$749,999

4 Beds ⋅ 2 Baths ⋅ 1047602 MLS

Welcome to 41 Richmond Street, a beautifully updated 4-bedroom, 2-bathroom Hi-Ranch situated on a fully fenced 8,276-square-foot lot in a highly desirable Islip neighborhood. Built in 1967 and offering 1,698 square feet of versatile living space, this property perfectly blends modern interior finishes with fantastic indoor-outdoor functionality. The bright and airy upper level greets you with gleaming hardwood floors, recessed lighting, and abundant natural light that flows seamlessly through the open-concept living and dining areas. The updated eat-in kitchen is designed for both daily life and entertaining, featuring crisp white cabinetry, stainless steel appliances, quartz countertops, and a classic subway tile backsplash. Three generously sized bedrooms and a fully renovated full bathroom with a modern vanity complete the main floor. The lower level significantly expands your living space, showcasing a large den anchored by a classic brick fireplace—ideal for cozying up during the colder months. This level also houses the fourth bedroom and a second full bathroom, offering maximum flexibility for guests, an in-law setup, or a dedicated home office. From the lower level, step outside to your private backyard retreat. The fully fenced yard features a spacious patio with brick accents and an above-ground pool, creating the perfect setting for summer barbecues and relaxation. Complete with central air conditioning, efficient oil heating, and an attached one-car garage, this home delivers comfort and convenience year-round. Conveniently located near schools, local shopping, dining, parks, and major roadways, this turnkey property is ready for you to call it home.

41 Richmond Street, Islip

$2,149,000

8 Beds ⋅ 6 Baths ⋅ 1042189 MLS

Step into a piece of Islip history with this extraordinary 1850s Colonial, a remarkable three-story residence offering approximately 5,145 square feet of living space, 8 bedrooms, 5 full bathrooms, 1 half bath and three separate staircases. Rich in architectural character and thoughtfully updated with modern amenities, this distinctive home beautifully blends historic craftsmanship with contemporary luxury. A grand entryway and sweeping staircase introduce an impressive interior showcasing original details, exposed wood beams, hardwood floors and multiple fireplaces. The formal living room features a wood-burning fireplace, while the chef’s kitchen is appointed with top-of-the-line appliances, a striking 10-foot island, exposed beams and an original fireplace converted to gas. An adjacent pantry and laundry area add convenience. The main level continues with a dramatic family room featuring soaring cathedral ceilings and a gas fireplace, along with a spacious office or optional bedroom with its own fireplace. A custom rear staircase leads to the serene primary suite overlooking the picturesque park-like grounds. The luxurious en-suite bath features a freestanding soaking tub, oversized walk-in shower with multiple body sprays and a custom walk-in closet. Additional bedrooms, full bathrooms and a second laundry area complete the second level. Ascend the home’s original winding staircase to the third story, where additional bedrooms and a spacious recreation room offer exceptional versatility, complemented by abundant closets and a finished storage room. Outside, expansive park-like grounds create a private outdoor oasis highlighted by a beautifully designed, fully fenced heated saltwater in-ground pool. A dedicated pool house/cabana with a changing room and full bathroom enhances the resort-style setting, while an additional shed provides convenient storage. The detached two-car garage is equipped with a Tesla Universal Wall Connector for EV charging. A rare opportunity to experience the history, craftsmanship and architectural character of an 1850s residence beautifully enhanced for modern living in the heart of Islip.

61 Ocean Avenue, Islip

$949,000

4 Beds ⋅ 4 Baths ⋅ 1039534 MLS

Welcome to 1536 Wingan-Hauppauge Road, a beautifully updated home tucked away on a quiet dead-end street, offering the perfect combination of privacy, space, and resort-style living. As you step inside, you’re welcomed by a bright, open layout that’s perfect for both everyday living and entertaining. Hardwood floors flow throughout the main living areas, leading to the heart of the home — an incredible custom chef’s kitchen. Featuring an oversized center island, abundant cabinetry, multiple prep and serving areas, and high-end appliances, this is truly a kitchen designed for gathering. The kitchen opens seamlessly to the dining and living spaces, where two fireplaces add warmth and character. Upstairs, the spacious primary suite features a vaulted ceiling and a beautifully renovated spa-like bath. Three additional generously sized bedrooms and convenient second-floor laundry complete this level. The home offers 3 full bathrooms and 1 half bath, providing plenty of space and functionality. The fully finished lower level adds even more living space and flexibility, with its own separate entrance, a full bathroom, an additional room perfect for guests or a home office, and plenty of storage. It’s a great space for extended living, entertaining, working from home, or simply having extra room to spread out. And then there’s the backyard — your own private retreat. Enjoy a heated saltwater in-ground pool, hot tub, expansive patio, BBQ area, and plenty of space for outdoor dining, entertaining, or just relaxing by the pool. Mature landscaping and the peaceful setting make the backyard feel private and secluded. Additional features include a brand-new roof, newer heating system, two-zone central air, attached 1.5-car garage, and a spacious driveway. This beautiful home offers the space, privacy, updates, and incredible indoor-outdoor lifestyle that make this home truly special.

1536 Winganhauppauge Road, Islip

$699,999

5 Beds ⋅ 3 Baths ⋅ 1029500 MLS

Welcome to 22 Manitton Court, where comfort, space, and easy living come together. This well maintained and inviting 5 bedroom, 2.5 bath home offers room for everyone, featuring a versatile bonus room with oversized windows, perfect for a home office, playroom, or guest space. Enjoy cozy evenings by the wood-burning fireplace and the timeless beauty of hardwood floors. Step outside to your private backyard retreat with a stunning 40' x 20' inground Gunnite pool, spacious new paver patio, and convenient poolside half bath, perfect for entertaining or simply relaxing all summer long. Additional features include a breakfast bar, French doors, mini-split cooling, a 2 car attached garage, and an unfinished basement with garage access. Conveniently located near shopping, restaurants, parks, and the train station. This won't last long!

22 Manitton Court, Islip

$799,000

4 Beds ⋅ 3 Baths ⋅ 1012712 MLS

Welcome to 269 Brookville Avenue, Islip! This beautifully maintained custom expanded ranch offers the perfect blend of comfort, functionality, and outdoor enjoyment. Featuring 4 spacious bedrooms and 3 full bathrooms, including a private primary suite with a walk-in closet and en-suite bath, this home provides ample space for today’s lifestyle. The heart of the home is the large chef’s kitchen, showcasing custom cabinetry, granite countertops, stainless steel appliances, and abundant workspace for cooking and entertaining. Bamboo hardwood flooring, recessed lighting, and thoughtful updates throughout add warmth and style. The generous bonus room above the garage offers endless possibilities for a home office, guest space, recreation room, or extended living area. Stay comfortable year-round with six mini-split air conditioning units, oil heat, oil hot water, a Lennox pellet stove, and a new hot water heater. Step outside to your private backyard retreat featuring a 14’ x 28’ in-ground pool surrounded by a custom paver patio—perfect for relaxing or entertaining family and friends. Additional amenities include a one-car garage and a 10-zone in-ground sprinkler system. A truly special property offering space, versatility, and exceptional outdoor living. Don’t miss this must-see home!

269 Brookville Avenue, Islip

$2,990,000

5 Beds ⋅ 5 Baths ⋅ 1011344 MLS

Experience exceptional waterfront living in coveted Bayberry Point with this custom-built cedar Colonial offering approximately 6,000 square feet of beautifully designed living space on a deep-water canal. Built with quality 2x6 construction, this impressive residence welcomes you with soaring ceilings, sun-drenched living spaces, and an open-concept floor plan designed for both everyday living and grand-scale entertaining. The gourmet chef’s kitchen features custom cabinetry, granite countertops, premium stainless steel appliances, oversized center island, and seamless flow into the dining area and spectacular great room with fireplace and walls of windows overlooking the resort-style backyard. The luxurious first-floor primary suite serves as a private retreat, complete with a fireplace, spa-inspired bath, steam shower, and generous walk-in closets. A first-floor guest suite with private bath and step-in shower offers ideal accommodations for family and visitors. Additional bedrooms are spacious and beautifully appointed, while a dedicated theater/media room provides the perfect setting for movie nights and entertaining. The home also features elegant formal dining spaces, multiple updated baths, custom millwork, hardwood flooring, a wet bar, and an incredible finished bonus area/man cave above the oversized three-car garage with private office space. Step outside to your own waterfront resort. The professionally landscaped grounds showcase a heated 20' x 40' saltwater pool surrounded by expansive paver patios, a pool house, outdoor stone fireplace, and multiple entertaining areas designed to take full advantage of the stunning canal views. Boaters will appreciate the 101-foot deep-water dock with easy access to the Great South Bay. A rare offering that combines luxury, quality craftsmanship, waterfront lifestyle, and resort-style amenities in one of the South Shore’s most desirable locations.

65 W Bayberry Road, Islip

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Islip City Homes with Pool

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