Shirley Real Estate

Welcome to Shirley, New York – a hidden gem nestled in the heart of Suffolk County. With its serene landscapes and vibrant community spirit, Shirley offers the perfect blend of suburban charm and natural beauty, making it an ideal place to call home.

Shirley is conveniently located on Long Island's South Shore, providing residents with easy access to stunning beaches, picturesque parks, and a plethora of recreational activities. The nearby Smith Point County Park is a local favorite, offering miles of sandy shoreline and opportunities for outdoor adventures such as hiking, fishing, and bird watching. Whether you’re soaking up the sun or enjoying a peaceful stroll along the shore, this area is a nature lover's paradise.

The community of Shirley is known for its friendly atmosphere and strong sense of belonging. With a variety of local shops, restaurants, and cafes, residents enjoy a laid-back lifestyle that emphasizes connection and camaraderie. Families will appreciate the excellent schools and community programs that foster growth and engagement for children of all ages.

For those who commute, Shirley offers convenient access to major highways and the Long Island Rail Road, making it easy to reach New York City and other destinations. This accessibility, combined with the town's charming residential neighborhoods, makes it a desirable location for both young professionals and families alike.

In Shirley, you’ll discover not just a place to live, but a community that welcomes you with open arms. Come explore the beauty and warmth of Shirley, where the perfect home awaits!

Newest Listings in 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

$799,000

4 Beds ⋅ 4 Baths ⋅ 1027999 MLS

Welcome to this beautifully renovated colonial 4 Bedrooms, 4 Bathrooms, Located in the highly of Shirley within the Longwood School District. Designed with versatility in mind, this exceptional home is perfect for growing or multigenerational. The professionally finished basement features its own private entrance, an expansive living area, a stylish full bathroom with a glass-enclosed shower, designer finishes, and a secondary kitchen, making it ideal for extended family, guests, a home office, or potential accessory use with proper permits. Set on a beautifully landscaped half-acre property, this home offers outstanding curb appeal and an incredible backyard built for entertaining. The oversized patio provides the perfect setting for summer gatherings, and outdoor relaxation while offering plenty of room to enjoy the surrounding privacy. Inside, the main level showcases rich bamboo flooring throughout, updated lighting, and an exceptionally large family room-a rare feature for this style of home. The custom-built media wall creates a stunning focal point, while oversized slider windows fill the space with natural light and offer peaceful backyard views. The formal dining room is equally impressive, featuring a beautiful modern fixtures and 2nd large sliding glass doors that seamlessly connect indoor and outdoor living. A conveniently located first-floor half bath also includes custom vanity & storage cabinets along with washer & dryer. At the heart of the home is a beautifully appointed chef's kitchen featuring custom cabinetry, soft close drawers, quartz countertop, a tile backsplash, pot filler, premium Kohler fixtures, and a full suite of brand-new stainless-steel appliances, including a refrigerator, range, wall oven, and built-in microwave. Offers a full deep pantry/storage cabinet right next to kitchen. Designed for both everyday living and entertaining, the kitchen offers abundant workspace and timeless style. The second level is highlighted by an inviting primary suite with vaulted ceilings, a private en-suite bath, an oversized walk-in closet, two additional closets, and a charming built-in window bench—perfect for enjoying your morning coffee or unwinding in the evening. Three additional generously sized bedrooms each feature dual closets with a beautifully updated hall bathroom, beautiful bamboo flooring throughout second floor too and elegant base and crown moldings complete the upper level. Additional features include central air conditioning, in-ground sprinklers, stylish PVC privacy fencing, new windows & slider doors throughout, custom door and window moldings and an attached two-car garage complete with custom shoe storage and built-in cabinetry. Energy-efficient features include first-floor ductless units that create a separate heating and cooling zone, allowing you to condition the main living area without running the entire home. Solar panels help keep electric costs exceptionally low, while natural gas heating (rare in the area) provides year-round comfort and efficiency. Every detail of this home reflects pride of ownership and quality craftsmanship, offering the perfect combination of comfort, functionality, and upscale finishes. Move-in ready and meticulously maintained, Close to highways and railroad.

397 Lockwood 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

$615,000

4 Beds ⋅ 2 Baths ⋅ 1025072 MLS

Welcome to this beautifully maintained 4-bedroom, 2-bathroom home that perfectly combines comfort, style, and functionality. The spacious primary bedroom is conveniently located on the main floor for easy accessibility. The heart of the home is the chef's kitchen, featuring a gas stove, abundant workspace, and durable tile flooring—ideal for preparing everyday meals or entertaining guests. Rich hardwood floors flow throughout the main living areas, while the upstairs features attractive laminate flooring for easy maintenance. Outside, you'll find a stunning in-ground saltwater pool surrounded by a beautiful paver patio, creating the perfect space for summer entertaining. Enjoy peace of mind knowing the pool filter was replaced in 2024 and the saltwater system was updated in 2025. Additional updates include a new roof. Need extra space? The full basement offers endless possibilities for storage, recreation, or future finishing. Car enthusiasts, hobbyists, and contractors will appreciate the impressive 2.5-car garage complete with a full second-story storage area, a dedicated electrical panel, and a camper outlet—truly a mechanic's dream. This property also features two separate driveways, providing ample parking and making it easy to accommodate a boat, camper, trailer, or multiple vehicles. This exceptional home offers the perfect blend of modern updates, versatile spaces, and resort-style outdoor living. Don't miss your opportunity to make this one-of-a-kind property your next home!

14 Tudor Road, 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

$589,990

4 Beds ⋅ 2 Baths ⋅ 1024739 MLS

Welcome to 25 Heston Rd, Shirley—a spacious 4-bedroom, 2-bath home featuring a full finished basement with the potential for a legal accessory apartment (with permits). Highlights include refinished hardwood floors, a large Chefs kitchen, Central AC, cathedral ceilings, double wide driveway, covered front porch and a 1-car garage. Enjoy a fully fenced PVC backyard, ideal for entertaining or relaxing. A versatile home offering space, comfort, and future potential. Photos may include virtual staging and digital enhancements for illustrative purposes only.

25 Heston Road, 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.