Shirley Real Estate

Welcome to Shirley, New York – a hidden gem nestled in the heart of Suffolk County. This charming town, located on the picturesque South Shore of Long Island, offers a unique blend of suburban tranquility and vibrant community spirit. With its rich history and scenic landscapes, Shirley is an ideal place for families, retirees, and anyone looking to enjoy the best of coastal living.

Shirley boasts a variety of recreational opportunities, with nearby beaches, parks, and nature reserves. The stunning Smith Point County Park, just a stone’s throw away, offers pristine sandy shores and a perfect spot for swimming, fishing, and picnicking. For those who enjoy outdoor adventures, the Wertheim National Wildlife Refuge provides a serene backdrop for hiking and birdwatching, allowing you to immerse yourself in nature’s beauty.

The town is also known for its strong sense of community, with local events and festivals that bring residents together throughout the year. From farmers' markets to holiday celebrations, there’s always something happening in Shirley, fostering connections among neighbors and friends.

Education is a priority in Shirley, with access to quality schools that cater to the needs of families. The town’s convenient location provides easy access to major highways and the Long Island Rail Road, making commuting to New York City a breeze.

With its affordable housing options, friendly atmosphere, and abundance of recreational activities, Shirley, NY, is not just a place to live; it's a place to thrive. Discover the charm of Shirley and find your perfect home in this delightful community!

Newest Listings in Shirley

$928,888

1032063 MLS

Welcome to 1 Grandview Drive, Shirley — a rare legal two-family home offering incredible versatility and beautiful Great South Bay water views directly across the street. This unique property features two oil tanks, two oil burners, and two electric meters, making it ideal for both homeowners and investors. The first-floor unit offers 2 bedrooms, 1 and a half baths, and two sunrooms, while the second-floor unit features 2 bedrooms and 2 full baths. Enjoy the peace of mind knowing this home does not require flood insurance while still providing the coastal lifestyle you've been looking for. Located just minutes from Smith Point Beach, shopping, dining, and the train station, and only steps away from a community beach area featuring a seasonal spray park, playground, picnic areas, restrooms, and breathtaking Bellport Bay views. Live in one unit while enjoying rental income from the other — or make this your own waterfront-view retreat. Wake up every day feeling like you're on vacation. Come see for yourself!

1 Grandview Drive, Shirley

$760,000

4 Beds ⋅ 2 Baths ⋅ 1031018 MLS

Picture waking up to the sound of water lapping just beyond your bedroom balcony, coffee in hand, watching the sun rise over the horizon, this is everyday life in this one-of-a-kind waterfront Cape Cod, nestled right on the border of Brookhaven in the sought-after William Floyd school district. This 4-bedroom, 2-bathroom home welcomes you with a bright, open floor plan filled with natural light, offering the perfect canvas for your next chapter, while outside, a spacious backyard and screened-in porch set the stage for unforgettable summer gatherings, quiet evenings, and front-row sunsets over the water. Hop on your bike or take a short stroll to the beach, where the charm of Shirley — proudly known as "Long Island's Best Kept Secret" — comes alive with fishing, boating, and swimming just steps from your door. Cross the Smith Point Bridge and you're on Fire Island, where Smith Point County Park delivers Atlantic Ocean beach days and live music echoing through the park all summer long. Waterfront homes like this, in this condition and at this price, simply don't come around often and they don't last. This isn't just a house, it's the lifestyle you've been waiting for.

62 Grandview Drive, Shirley

$499,000

3 Beds ⋅ 1 Baths ⋅ 1031060 MLS

Welcome home to this charming three bedroom, one bath ranch in Shirley, set on an oversized property that gives you room to breathe, play, and grow. Step inside to a bright, comfortable layout with easy single level living. The converted garage adds flexible bonus space perfect for a den, home office, gym, or extra living area while the basement provides valuable storage or future potential. Outside, the expansive yard invites entertaining, gardening, and outdoor fun in every season. Conveniently located near local shops, dining, parks, and major roadways. This home blends suburban comfort with everyday convenience. Ready for your next chapter? Come see the possibilities.

61 W End Avenue, Shirley

$659,000

3 Beds ⋅ 2 Baths ⋅ 1030459 MLS

COMING SOON!!! Professional pictures to come!! This charming single-family home is set on a spacious half-acre property in the heart of Shirley. Offering approximately 1,440 square feet of living space, this 3-bedroom, 1.5 bath residence provides a comfortable layout with plenty of room for everyday living and entertaining. The expansive backyard offers endless possibilities for outdoor enjoyment with an above-ground, a large yard that can accomodate gardening, recreation, and future enhancements. Whether you're a first-time homebuyer, looking to rightsize, or searching for an investment opportunity, this property combines space, privacy, and potential. Conveniently located near shopping, restaurants, schools, parks, beach with bridge access to the Fire Island National Seashore, train station and major roadways, this home provides easy access to everything the area has to offer while maintaining the tranquility of a residential neighborhood. Don't miss the opportunity to make this property your own.

565 Starlight Drive, Shirley

$650,000

5 Beds ⋅ 3 Baths ⋅ 1030193 MLS

Welcome to 38 Appel Drive in Shirley! This spacious Colonial offers 5 bedrooms, 2.5 bathrooms, and a 2-car garage. The main level features a large living room, formal dining room, and a spacious eat-in kitchen with granite countertops and stainless steel appliances. Upstairs, hardwood floors run throughout the second level, and the primary bedroom features a recently updated private bathroom. Generously sized rooms and a functional layout provide plenty of space for everyday living and entertaining. Conveniently located close to shopping, dining, parks, transportation, and local beaches, this home offers a great combination of space, comfort, and convenience.

38 Appel Drive E, Shirley

$569,900

3 Beds ⋅ 2 Baths ⋅ 1029794 MLS

Gorgeous colonial style home with contemporary flare, updated with amazing craftsmanship and magnificent attention to detail. This beauty boasts a full basement with OSE, a large and beautiful backyard and plenty of windows for the warmth and comfort of exceptional sunlight. This property has close proximity to parks, schools, transportation, shopping, eateries, and other neighborhood conveniences.

65 Westminster Drive, Shirley

$475,000

3 Beds ⋅ 3 Baths ⋅ 1029049 MLS

Welcome to this charming 3-bedroom, 2.5-bath ranch offering comfortable one-level living with plenty of extra space! Hardwood floors flow throughout the main level, complemented by newer windows that fill the home with natural light. Relax in the inviting screened-in porch overlooking the backyard—perfect for morning coffee or entertaining. The full basement offers a finished living area, a separate laundry room, and an abundance of storage space to fit all your needs. With low taxes and a layout that's ideal for first-time buyers, down-sizers, or anyone looking for easy living, make sure to catch this home!

152 Parkwood Drive, Shirley

$169,900

1028758 MLS

Fully cleared lot with both Board of Health and ZBA Variance approvals in hand for a 1,500 sq. ft. residence + 1 car garage. Water, electric, and cable are all in the street and ready to hook up. Offered strictly with current approvals in place—perfect for a builder or investor looking for a hassle-free project!

37 Seymour Drive, Shirley

$424,999

3 Beds ⋅ 1 Baths ⋅ 1026337 MLS

Welcome to this beautiful 3 bedroom home offering comfort, style, and an unbeatable location just minutes from the beach. The bright and inviting interior features wood floors throughout and an open concept kitchen complete with granite countertops and brand new stainless steel appliances. major improvements include a high efficiency Navien heating system providing peace of mind for years to come. Whether you're looking for a year-round residence or the perfect weekend retreat, this home offers the ideal blend of convenience and coastal living. Located close to local restaurants, shopping, parks, and all the amenities the South Shore has to offer, you'll enjoy easy access to nearby beaches and everything Shirley has to offer.

7 Edwards Drive, Shirley

$549,900

4 Beds ⋅ 2 Baths ⋅ 1025731 MLS

Welcome to this beautifully maintained ranch offering the perfect blend of comfort, style, and versatility. The main level features 3 spacious bedrooms, 1 full bathroom, an updated kitchen with stainless steel appliances, skylights that fill the home with natural light, central air conditioning, baseboard heat, and updated hardwood floors throughout the living room, dining room, and hallway. The fully finished basement provides exceptional additional living space with a separate outside entrance, a bedroom, office, large recreation area, and a full bathroom—ideal for extended family, guests, a home office, or potential accessory living with proper permits. Outside, enjoy a fully fenced backyard designed for entertaining, complete with a brick patio, fire pit, and in-ground sprinkler system. Additional highlights include a one-car garage, an all-brick double-wide driveway, and excellent curb appeal. Situated on a quiet street, this home offers the perfect combination of peaceful living and convenient access to shopping, restaurants, parks, and transportation. Don't miss this move-in-ready opportunity with flexible living space both inside and out!

31 Westwood Drive, Shirley

$919,000

4 Beds ⋅ 4 Baths ⋅ 988791 MLS

Located in the desirable Woodland Estates section of Shirley, this beautifully updated 5-bedroom, 3½-bath corner property is situated on an expansive 0.8-acre lot and offers an open floor plan with cathedral ceilings, hardwood and ceramic tile flooring, recessed lighting, a wood-burning fireplace, and central air conditioning. The eat-in kitchen features designer cabinetry, granite countertops, stainless steel appliances, and opens seamlessly to the main living areas, while a formal dining room adds to the home's functional layout. A full finished basement with an outside entrance provides a large recreation area and ample storage. Outside, enjoy a beautifully maintained backyard with a spacious deck, BBQ area, and large in-ground pool. Additional features include a fully insulated two-car garage currently being used as a game room with an electric vehicle charging hookup, a newly expanded driveway, and quality updates throughout, making this exceptional home move-in ready.

12 Deer Path, Shirley

$539,000

3 Beds ⋅ 3 Baths ⋅ 1024992 MLS

Welcome to 269 Carleton Dr E. Nice ranch located in a quiet street it has 3 Brs. and 2.5 bath. And finished basement. Great conditions. Fully Available~!!!!!

269 Carleton Drive E, Shirley

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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.