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39 Seymour Drive, Shirley
$539,999
3 Beds ⋅ 2 Baths ⋅ 1039597 MLS
Well-maintained Victorian-style home offering 3 bedrooms and 2 full bathrooms in a convenient Shirley location. Updated in 2024, the home features a spacious kitchen with quartz countertops, shaker cabinetry, and stainless steel appliances. The main level offers comfortable living and dining spaces, including a family room with a stone fireplace and decorative molding details. Upstairs, the primary bedroom includes vaulted ceilings and generous closet space. Washer/dryer in the second floor. Additional features include central air conditioning, updated bathrooms, hardwood flooring on the first level, attached garage, in-ground sprinklers, and a fully fenced backyard with plenty of room for outdoor enjoyment. Built in 2005 and thoughtfully updated, this home is located near local shopping, dining, parks, beaches, and major roadways, offering both comfort and convenience. Move right in and make it your own.

39 Seymour Drive, Shirley

40 Greentree Court, Shirley
$530,000
2 Beds ⋅ 2 Baths ⋅ 1004153 MLS
THIS PARTICULAR UNIT BOASTS SUPERIOR CUSTOM LAY OUT AND UPGRADES BABY!!!! UPGRADES!! Welcome to The BEDFORD a desirable GROUND FLOOR model Located in The Manors at Colony Preserve! Your Ultimate Haven in the Heart of a coveted 55 and Over Community! Luxury living, meticulously crafted two-bedroom unit, Beautifully Upgraded, Including granite Counter tops, Kitchen Recessed lighting, two full bathrooms, Updated Appliances, Sliders to your Private EXPANDED CUSTOM PATIO, Beautiful tile floors and full garage with custom epoxy flooring! Enjoy upgrades such as custom cabinetry and attention to detail with crown molding, upgraded appliance package. Take note of the "two" water spickets for convenience! ! One water source in the garage and one on the patio as well! Instant hot water heater and custom closets! "This particular Bedford unit" offers the epitome of upgraded layouts LIKE NO OTHER FEATURING DESIRABLE OPEN CONCEPT! Indulge in top-of-the-line amenities including a shimmering pool, relaxing Jacuzzis! Enjoy a lifestyle of unparalleled ease, every need is met effortlessly. TIME TO DITCH THOSE SHOVELS, RAKES AND LAWN MOWERS! Those days are now over! Experience the relaxation with well-manicured bocce courts, serene walking trails around a picturesque lake, and charming gazebos scattered throughout the community. The immaculate clubhouse beckons with its state-of-the-art gym, life fitness center, game rooms, library, and inviting social events calendar! You'll be "feet in the sand" in minutes as your only 2 miles from Smith Point Beach, Tiki Joe's and the breathtaking Atlantic Ocean! Take a breath of fresh air on your private patio and soak in the tranquil surroundings. Isn't it time to experience a hassle-free lifestyle? Simply turn the key and let The Manors take care of the rest. As a dedicated realtor for 28 years, I wholeheartedly stand behind the exceptional value and lifestyle offered by this 55 and over community. In fact, I am so confident in its merits that I proudly facilitated the purchase of a home for my own parents within this esteemed Community! With top-tier amenities, a vibrant social atmosphere, and a commitment to providing residents with the utmost comfort and convenience, this community embodies everything one could desire in their golden years. I invite you to explore the countless benefits. The BEDFORD at Colony Preserve, your new home sweet home. You've been around long enough to know opportunity is not a lengthy visitor!

40 Greentree Court, Shirley

15 Maplewood Drive, Shirley
$525,000
3 Beds ⋅ 2 Baths ⋅ 990536 MLS
Welcome to this beautifully expanded Cape, offering comfort, space, and convenience in a desirable location. This well-maintained home features gleaming hardwood floors throughout and a spacious first-floor primary bedroom complete with a walk-in closet for ample storage. The full bathroom is designed for relaxation, showcasing a luxurious whirlpool tub—perfect for unwinding after a long day. The home’s thoughtful layout provides both functionality and charm, ideal for a variety of lifestyles. Brand new stainless steel appliances and open floor plan. Step outside to enjoy a fully fenced yard, offering privacy and plenty of space for outdoor entertaining, gardening, or pets. Yard equipped with your own dog run. With low taxes under $7,000, this property presents an excellent opportunity for affordable homeownership. Conveniently located close to public transportation, shopping, dining, and just a short drive to Smith Point Beach, this home combines suburban tranquility with easy access to everyday essentials and recreation. Don’t miss your chance to make this inviting home your own!

15 Maplewood Drive, Shirley

33 Greentree Court, Shirley
$510,000
2 Beds ⋅ 2 Baths ⋅ 1022293 MLS
Welcome to 33 Greentree Court, a beautifully appointed second-floor condominium in a desirable gated 55+ community offering the perfect blend of comfort, convenience, and low-maintenance living. This recently constructed home features 2 spacious bedrooms, 2 full bathrooms, a versatile bonus room, cathedral height ceilings, and an eat-in kitchen overlooking the covered terrace, perfect for enjoying your morning coffee or unwinding at the end of the day. Enjoy the convenience of an attached garage, private in-unit elevator, and in-unit laundry. Whether you’re looking to embrace a more leisurely lifestyle or need a home that accommodates an active work schedule, this residence offers modern amenities designed for ease and comfort. Residents enjoy a vibrant clubhouse with social events, a swimming pool, hot tub, bocce courts, and scenic walking trails. Ideally located near major roadways, transportation, shopping, the East End, Patriots Preserve, and Smith Point County Park, this is an exceptional opportunity to enjoy the best of Long Island living.

33 Greentree Court, Shirley

8 Halewood Drive
$509,999
3 Beds ⋅ 2 Baths ⋅ 1044873 MLS
Beautifully maintained 3-bedroom, 2-bath home at 8 Halewood Drive in Shirley, offering comfort, functionality, and an inviting backyard oasis. The spacious utility room features ample pantry shelving, a washer and dryer, and convenient storage. The home also features upgraded electrical service with an additional subpanel, a new tankless water heater, and a whole-house generator. The outdoor backyard space is designed for entertaining, featuring an expansive composite deck, a 12-foot above-ground pool with an additional composite pool deck, hot tub, established gardens and mature landscaping with sprinkler system, as well as an enclosed outdoor shower. A 21 foot by 10 foot retractable awning is included. A large detached shed/garage provides excellent storage or workspace. The driveway extends to the rear shed and comfortably accommodates at least four vehicles in the front. The home also includes a basement crawlspace and boarded attic, providing additional storage space. A separate PVC fence encloses the property, offering privacy and security. Some photos have been digitally enhanced to remove clutter.

8 Halewood Drive

55 William Floyd Parkway, Shirley
$499,999
4 Beds ⋅ 2 Baths ⋅ 998830 MLS
Welcome to this lovely 4 bedroom, 2 full bathroom home in Shirley, ideally located within walking distance to the beautiful and renowned Smith Point Beach. Originally enhanced in 1996 with a second-story addition, the home also received a new roof and new siding at that time, and all Certificates of Occupancy are in place, providing peace of mind for the next owner. Step inside to a warm and inviting layout featuring a comfortable living room that flows seamlessly into the eat-in kitchen, complete with sliding glass doors leading to the backyard. The first floor also offers two bedrooms and a full bathroom, providing convenient one-level living options. Upstairs, you'll find a generously sized primary bedroom with a spacious sitting area that can easily serve as a private retreat, reading nook, home office, or relaxation space. An additional bedroom, oversized dedicated laundry room, and full bathroom featuring both a tub and separate shower complete the second level. Outside, a storage shed provides additional space for tools, beach gear, bicycles, and seasonal items. Just a short stroll from Smith Point Beach on the Fire Island barrier beach, this location is a true haven for beach lovers and outdoor enthusiasts, offering white sandy beaches, rolling Atlantic waves, camping, fishing, scuba diving, swimming, food concessions, and the nationally recognized Smith Point lifeguard headquarters. Conveniently located near shopping, dining, and everyday amenities, with the Long Island Rail Road approximately 4 miles away, this home offers an ideal blend of relaxed coastal living and everyday convenience. Whether you're searching for a year-round residence, weekend getaway, or peaceful retreat near the shore, this home offers the opportunity to enjoy the laid-back beach lifestyle you've been dreaming of.

55 William Floyd Parkway, Shirley

35 Lombardy Drive, Shirley
$499,900
3 Beds ⋅ 2 Baths ⋅ 1051751 MLS
Welcome Home to This Beautifully Renovated Retreat, Move-In Ready and Waiting for You to Make It Your Own. This Home Has Been Extensively Renovated from Top to Bottom, Starting with a Stunning New Eat-In Kitchen Featuring Quartz Countertops, New Stainless Steel Appliances, and a Breakfast Bar Perfect for Casual Mornings or Entertaining Guests. Both Bathrooms Have Been Tastefully Updated, Offering One Full Bath and One Half Bath for Everyday Convenience. New Flooring and Carpet Flow Throughout, Complementing the Open, Light-Filled Entry That Welcomes You the Moment You Walk In. New Windows and a New Sliding Door Bring in Even More Natural Light While Adding Energy Efficiency, and a New Garage Door Rounds Out the List of Fresh, Turnkey Updates. Ideally Located Close to the Ocean Beaches, This Home Offers the Best of Low-Maintenance Coastal Living. Every Major Update Has Already Been Done. Just Bring Your Furniture and Relax.

35 Lombardy Drive, Shirley

2 Pinetop Drive, Shirley
$499,900
4 Beds ⋅ 2 Baths ⋅ 1034963 MLS
Welcome to this well-maintained four-bedroom, two-bathroom ranch situated on a corner property with a convenient location and numerous updates throughout. Offering a versatile floor plan, this home provides comfortable living with functional spaces for a variety of needs. The updated kitchen features granite countertops, stainless steel appliances, and ample cabinet space. The living room is highlighted by vaulted ceilings, a wood-burning stove, and sliding glass doors that provide access to the backyard, creating a seamless connection between indoor and outdoor living. Down the hall are four bedrooms, including a spacious primary bedroom with an en-suite bathroom. A second full bathroom serves the additional bedrooms. Other highlights include an attached garage, a large driveway offering ample parking, and a corner lot with outdoor space to enjoy. Conveniently located near shopping, dining, transportation, parks, and other local amenities, this home is ready for its next owner.

2 Pinetop Drive, Shirley

58 Appel Drive E, Shirley
$499,000
4 Beds ⋅ 2 Baths ⋅ 1049711 MLS
Welcome to Your Turnkey Coastal Masterpiece in Shirley! Nestled in the heart of Shirley, this fully renovated, 1,500 sq. ft. ranch seamlessly blends modern elegance with effortless everyday living. Step inside to a sun-drenched, open-concept floor plan accented by gorgeous new flooring and premium finishes throughout. The stunning chef’s kitchen serves as the heart of the home, showcasing sophisticated shaker-style cabinetry, luxurious quartz countertops with a matching slab backsplash, and high-efficiency stainless steel appliances. Whether you’re preparing a meal or entertaining guests, this kitchen is designed to impress. The versatile layout features 4 bedrooms, 2 full bathrooms, and a spacious 5th bonus room with endless possibilities. Use it as an additional bedroom, home office, or create a second kitchen for the potential of a mother-daughter-style setup, with proper permits. The bonus room also offers a separate entrance, providing added flexibility and convenience. Enjoy exceptional peace of mind with an extensive list of brand-new upgrades, including a new roof, siding, gutters, plumbing throughout, electric water heater, 200-amp electrical panel, renovated bathrooms, washer and dryer, and a spacious 4-car driveway. Step outside into your private backyard oasis, complete with an expansive patio perfect for summer barbecues, outdoor entertaining, relaxing , or enjoying peaceful evenings under the stars. Conveniently located just minutes from beautiful beaches, the marina, parks, and schools, with easy access to shopping and major roadways, this home combines modern comfort with Shirley’s desirable coastal charm. Additional highlights include low property taxes and no flood insurance requirement. This exceptional turnkey home is ready to welcome its next owners. Schedule your private showing today and experience coastal living at its finest!

58 Appel Drive E, Shirley

36 Schenk Drive, Shirley
$499,000
4 Beds ⋅ 2 Baths ⋅ 1037858 MLS
FOR SALE: Spacious Ranch with lots of potential on Schenk Drive! Unlock Your Dream Home in the Heart of Shirley! Welcome to 36 Schenk Drive—an exceptional opportunity to secure an over-sized ranch that is truly ready for its next chapter. Situated on a beautiful, quiet street, this home is the perfect canvas for someone looking to infuse their own personal style and make it their own. Key Highlights: Expansive Living: This over-sized ranch features a fantastic, modern open floor plan that creates a seamless flow between living areas, making it ideal for both entertaining and daily relaxation. Versatile Space: With 4 spacious bedrooms, there is plenty of room for family, guests, or a dedicated home office. Endless Possibilities: Benefit from a huge, full basement—providing incredible storage or the perfect foundation for a future finished recreational space, gym, or workshop. Value Like No Other: Priced with an uber-aggressive asking price, this home offers an unbeatable entry point into a desirable community. Prime Location: Enjoy the perfect balance of suburban tranquility and ultimate convenience. You are just moments away from everything you need: Retail & Shopping: Located near a massive selection of shopping destinations, including a Super Walmart and the popular Tanger Outlet Center for all your shopping needs. Commuter Friendly: Easy access to local mass transit makes getting around simpler than ever. Lifestyle: Experience the best of the area with proximity to local dining, parks, and all the essential amenities that make a location "worth while." Don’t miss out on this incredible opportunity to build equity and create the home of your dreams. This property is priced to move and won't last long!

36 Schenk Drive, Shirley

567 Boxwood Drive, Shirley
$489,999
3 Beds ⋅ 1 Baths ⋅ 1059350 MLS
Explore this charming home, set on an expansive property with plenty of space to enjoy the outdoors and endless potential to make it your own. Inside, a beautifully refreshed interior feels bright and welcoming, with natural light filling each room. Three bedrooms and one bathroom offer just the right amount of space, while the nicely appointed kitchen features stainless steel appliances, granite countertops, and plenty of storage in the wood cabinets. TOTAL SQUARE FOOTAGE IS 1,950, sitting on a 0.25 acre lot, with a lot of the backyard being wooded, providing a truly private oasis. Recent updates include luxury laminate flooring, granite counters, stainless steel appliances, bathroom vanity, faucets, fresh paint throughout, freshly sealed blacktop driveway, updated electric panel, boiler, and more. The home also boasts a full, unfinished basement with private, outside entrance, via the side door. This NORTH SHIRLEY Ranch is part of the LONGWOOD SCHOOL DISTRICT, and close to major highways and the Long Island Expressway, offering comfort and conveniece. Come discover 567 Boxwood Drive, a beautifully updated and move-in ready home!

567 Boxwood Drive, Shirley

127 Johns Neck Road, Shirley
$475,000
3 Beds ⋅ 2 Baths ⋅ 973453 MLS
Waterfront Living with Private Dock – Rare Opportunity! Welcome to a unique waterfront property offering the perfect blend of lifestyle, investment potential, and future expansion. Situated on an oversized 0.43-acre lot, this home features direct water access with a private dock—ideal for boating, fishing, kayaking, or simply enjoying peaceful waterfront views right from your backyard. The existing residence offers approximately 1,200+ square feet of living space with 3 bedrooms and 2 full bathrooms. Whether you’re looking to renovate, expand, or rebuild, this property presents endless possibilities to create your dream waterfront home. The expansive lot provides ample space for outdoor entertaining, storage, or future development, making it a standout opportunity for both end-users and investors alike. Located in the desirable Shirley area within the Town of Brookhaven, this home offers convenient access to beaches, marinas, parks, shopping, and major roadways while maintaining a quiet, coastal neighborhood feel. Property Highlights: • Waterfront property with private dock • Oversized 0.43-acre lot • 3 bedrooms / 2 full bathrooms • Approx. 1,284 square feet of living space • Endless renovation, expansion, or rebuild potential • Ideal for boating and outdoor lifestyle • Low taxes. Perfect for: End-users, investors, builders, or anyone seeking a waterfront lifestyle opportunity. Don’t miss this rare chance to own a waterfront property with incredible upside potential in a prime Long Island location.

127 Johns Neck Road, Shirley

154 W End Avenue, Shirley
$469,999
2 Beds ⋅ 1 Baths ⋅ 1053238 MLS
Welcome to this beautifully updated Shirley home, set on a double lot in Flood Zone X with taxes under $3,500 and an incredible amount of usable outdoor space. Major exterior updates include a new roof with all plywood replaced (March 2022), new siding and gutters (2022), front and side windows (February 2022), new front porch rafters (2022), and solar panels (2022). The interior offers a comfortable open layout with a spacious living room and dining area, abundant natural light, recessed lighting, and updated LVP flooring completed in October 2025. The kitchen features abundant cabinetry, stainless steel appliances, a center island, and a layout that opens directly into the main living space. A 4-zone mini-split system was installed in 2023/2024, with two zones currently connected and two additional zones available for future use. The basement was remodeled in April 2024, creating additional finished space for a home office, recreation area, gym, or storage. Outside, the property truly shines with a paver patio and dedicated hot tub pad completed in June 2024, hot tub added in August 2024, 12x20 shed added in 2024, full underground irrigation installed in June 2025 with seven zones plus a front-bed mister, new driveway with paver border and retaining wall completed in July 2025, and new sod installed in August 2025. The expansive backyard has been further enhanced with 2026 landscaping, vinyl fencing installed in phases throughout 2025 and 2026, multiple entertaining areas, a fire-pit area, outdoor dining space, and plenty of open lawn, providing an ideal setting for entertaining or enjoying the property year-round. Additional updates include a 2021 hot water heater, 2021 Frigidaire dishwasher, and September 2025 Samsung Bespoke refrigerator. With its oversized lot, extensive updates, finished basement, impressive outdoor setup, and low taxes, this home offers a rare opportunity in Shirley.

154 W End Avenue, Shirley

96 Trafalgar Drive, Shirley
$450,000
3 Beds ⋅ 1 Baths ⋅ 1050091 MLS
Charming Shirley Beach Cape. Welcome to this beautifully maintained Cape Cod-style home in Shirley, ideally located close to Smith Point County Park and beach. This inviting home offers timeless character and thoughtful updates throughout, including newer 200 amp electric panel with whole house surge protection, updated, plumbing, 2025 water heater, 2024 above ground oil tank and more. The living area features a wood-burning steel lined fireplace perfect for cozy evenings and beautiful wood floors, The oversized garage offers plenty of space for parking, storage, or hobbies. The beautifully landscaped grounds with wonderful curb appeal are fantastic for outdoor enjoyment! Move-in ready! This special property has never been offered for sale before! The original family has owned it since the 1940's and the pride of ownership shows throughout this lovely home. No Sandy Damage to House or Garage. Come see all that this Shirley gem has to offer!

96 Trafalgar Drive, Shirley

75 Westminster Drive, Shirley
$425,000
3 Beds ⋅ 1 Baths ⋅ 1046585 MLS
If you are looking for a home less than half a mile away from the beach, this wonderful 3-bedroom ranch is the home for you. Low taxes and modern features make for a great starter home with potential to add more living space. There are many features, including a front porch, vinyl siding, and a roof less than 10 years old. The gutters, windows, and doors have been updated. The eat-in kitchen and open floor plan will let you entertain and enjoy your home without feeling claustrophobic. Shirley Beach is .4 miles away, and a short drive will get you to a favorite area, Smith Point County Park, Beach, and Campground. If you prefer to hangout in your new home the dining area has a sliding door to a composite deck and a private yard.

75 Westminster Drive, Shirley

82 Rugby Drive, Shirley
$400,000
2 Beds ⋅ 1 Baths ⋅ 1055838 MLS
This inviting Ranch brings together warmth, comfort and easy access to the outdoors. The kitchen is the heart of the home, with beautiful butcher block countertops. stainless steel appliances, and a breakfast bar that invites you to linger. A separate dining area offers space to gather, while ductless splits cooling keeps things comfortable. Glass sliding doors opening to the deck, extending the living space toward a newly added patio and fenced backyard-an inviting setting for slow mornings and summer evening. Shirley beach and its Splash Park are a short walk away with Smith Point Beach and the Mastic-Shirley LIRR station a short drive. The whole home truly carries the relaxed, breezy feel of coastal living!

82 Rugby Drive, Shirley

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.