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$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
$439,990
3 Beds ⋅ 1 Baths ⋅ 1044617 MLS
Welcome to 7 Wellwood Drive, a charming 3-bedroom, 1-bath ranch offering updated exterior features, a great outdoor setup and plenty of future potential. Inside, you’ll find a comfortable single-level layout along with a full basement featuring an outside entrance—ideal for creating additional living or recreational space, with potential rental possibilities subject to proper permits. The home features a newer roof, windows and siding, brand-new exterior doors and front railings, a Roth oil tank and in-ground sprinklers. Outside, the beautiful paver driveway adds standout curb appeal, while the fully PVC-fenced yard and private patio create the perfect setting for relaxing, entertaining and summer gatherings. Just a short distance from Smith Point Beach and its swimming, fishing, camping and outdoor recreation, this home offers a lifestyle you’ll enjoy year-round. With low annual taxes of only $7,726, 7 Wellwood Drive is a wonderful opportunity for buyers looking for value, versatility and room to grow.

7 Wellwood Drive, Shirley
$849,000
3 Beds ⋅ 4 Baths ⋅ 1042321 MLS
Live, Work And Thrive In One Exceptional Property!! This One Of A Kind Versatile Property Offers A Unique Opportunity For Those Seeking The Perfect Combination Of Comfortable Residential Living And Dedicated Professional Office Space. The Thoughtfully Designed Layout Provides The Convenience Of Having A Professional Workspace Right On The Property-Ideal For An Entrepreneur, Business Owner, Professional, Or Anyone Looking To Eliminate The Commute While Maintaining A Clear Separation Between Home And Work. The Professional Office Area Offers An Impressive And Functional Setting For Meeting Clients, Conducting Business, Or Operating A Home-Based Professional Practice, While The Residential Portion Provides The Comfort And Privacy Of Home. Situated On William Floyd Pkwy. WIth Convenient Access To Major Roadways, Shopping, Dining, Ocean Beaches, Marinas And Everyday Amenities, This Property Offers Exceptional Flexibility And Potential. Professional Office Includes Two Exam Rooms/Offices, Receptionist/Office/Waiting Room, Full Bathroom, A Separate Dedicated Entrance And Plenty Of Parking. Don't Have A Business-Easily Convert This Space To Additional Bedrooms Or Living Space!! Expanded Home Features Full Formal Dining Room, Updated Eat In Kitchen With Island, Custom Cabinetry, Granite Counters, KitchenAid Stainless Steel Appliances, Gas Cooking, 2 Ovens, Formal Living Room With Vaulted Ceilings, Skylights And Gas Fireplace, Oversized 1st Floor Primary Bedroom With Ensuite Bathroom And Walk In Closet, 2 Large Additional Bedrooms On 2nd Level, Updated Roof, Siding, Andersen 400 Series Windows, Buderis Boiler, Ductless CAC, In Addition This Home's Backyard Is An Entertainers Paradise!!! Lovely Bright And Airy Mahogany & Bamboo Screened In Porch Provides The Entryway To A Huge Paver Patio With Inground Pool, Custom Outside Bar, Outside Bathroom, Tiki Bar, Custom Ipe Decking With Seating, Gas Fire Pit And Gas Tiki Torches, Custom Covered Pavilion, Large Shed, Fully Landscaped Property, Huge 3 Car Attached Garage WIth 2nd Story Loft That Has Endless Possibilities, Full Finished Basement, 2 Driveways, This Immaculate, Custom Home Can Be Yours!!!

283 William Floyd Parkway, Shirley
$439,900
3 Beds ⋅ 1 Baths ⋅ 1042243 MLS
Welcome to 24 Trafalgar Drive! This inviting 3-bedroom, 1-bath home offers an updated kitchen and several valuable improvements, including the roof and siding updated approximately two years ago, a re-insulated attic, new back sliding door and leased solar panels designed to help reduce electric costs. Step outside onto the beautiful back deck-an ideal space for relaxing, barbecuing, and outdoor entertaining. The basement features a French drain system, providing additional space and peace of mind. Enjoy a convenient coastal lifestyle just a short walk or bike ride from Shirley Beach and its splash pad. Smith Point County Park is also only a quick drive or bike ride away, offering ocean swimming, music, fishing, camping, four-wheel-drive beach access, and more. With construction recently underway on the beautiful new Smith Point Bridge, this is a wonderful opportunity to own a home near some of Long Island's best outdoor recreation!

24 trafalgar Drive, Shirley
$499,000
3 Beds ⋅ 1 Baths ⋅ 1035203 MLS
Welcome to 4 Beechwood Drive! This Charming 3 Bedroom Hi-Ranch Home Is A Fantastic Opportunity For Those Seeking Space, Flexibility, & LOW TAXES. Situated On A Desirable Double Lot, The Property Offers Ample Room For Outdoor Entertaining, & Potential Extended Family Or M/D with Proper Permits. Inside, Enjoy An Updated Kitchen Along With Newer Roof And Newer Siding. Ideally Located Near Shopping, Brookhaven National Lab, Smith Point Beach, Parks, Camping, Fishing, & Recreation With Convenient Access To Major Highways & The Long Island Railroad. Enjoy All That The South Shore Has To Offer While Making This Home Your Own!

4 Beechwood Drive, Shirley
$539,000
4 Beds ⋅ 2 Baths ⋅ 1036276 MLS
Beautifully maintained ranch nestled in a desirable Shirley neighborhood! This inviting property features a spacious layout with four comfortable bedrooms, including a generous second floor primary suite complete with private full bathroom and two large closets. The main floor offers a living area perfect for entertaining, paired with a bright eat-in kitchen and a dedicated laundry room, plus three bedrooms and a full bathroom. Step outside to enjoy a fully fenced yard with beautiful landscaping and a newly installed deck. Centrally located with easy access to local parks, beaches, and shopping. Don't miss the chance to make this move-in ready gem your own!

9 Robinson Drive, Shirley
$389,000
3 Beds ⋅ 1 Baths ⋅ 1037450 MLS
Are You a First Time Home Buyer, Looking to Downsize or an Investor? Don’t Miss Out on this 3 Bedroom, 1 Bathroom Ranch – Priced Well with Low Taxes and with Some TLC and Updating, this Could Be the Perfect Home to Start Your Next Chapter In. Additional Home Features and Updates Include: Living Room, Dining Room, Eat-in Kitchen, Three Season Room, Brand New 100 Amp Electrical Service, New Oil Tank, Fenced Backyard and Multi-Car Driveway. Desirably Located - Just Minutes from Local Beaches, Marina, Parks, Preserves, Shopping, Restaurants and Roughly 20 Minutes from the Hamptons and 60 Minutes to New York City. Award Winning William Floyd School District. Call Today to Schedule Your Private Showing. Located in a Flood Zone - No Damage from Sandy.

92 Lombardy Drive, Shirley
$569,998
3 Beds ⋅ 2 Baths ⋅ 1036116 MLS
Bring your vision to this charming 3-bedroom, 2-full-bath Cape, beautifully positioned on a double lot with captivating water views and unforgettable sunsets. There is something special about a home with a setting like this—and the possibilities are truly exciting. Transform this property into something uniquely your own. The double lot offers wonderful potential for future expansion, subject to proper permits and approvals. Enjoy the beauty of the water, spectacular sunsets, a fantastic location, and the added benefit of low annual taxes of approximately $6,500. A wonderful opportunity to create the home you've been envisioning in a setting that's hard to duplicate. *The home was originally configured as a 4-bedroom, 1-bath residence and is reflected as such in the Town of Brookhaven property records. The current layout offers the potential to reconfigure the space and restore the additional bedroom, subject to buyer verification and any required permits or approvals. The double lot also provides wonderful potential for future expansion, subject to proper permits and approvals. Home is being sold as-is. *Roof, windows & electric were all updated in 2019. Water views and sunsets for eternity!!!

21 Grandview Drive, Shirley
$469,000
3 Beds ⋅ 2 Baths ⋅ 1033028 MLS
Siding, roof, windows, patio, peak and columns updated in 2011. Boiler and water heater (2010). Cesspool is 10 yrs old (2016). This property is one block from the Bellport Bay and Shirley Beach with a Splash Park and playground. Close to the marina, shopping, highways and Smith's Point Beach.

13 Manor Drive, Shirley
$449,000
3 Beds ⋅ 2 Baths ⋅ 1020948 MLS
Great space, great layout, and an awesome location - just 1.5 miles from Smith Point ocean beach, and less than a half mile from "Shirley Beach" and splash park, which overlooks Bellport Bay and faces directly west with some of the most breathtaking sunsets on Long Island. This home features central AC, vaulted ceilings and hardwood floors throughout entire first floor. If you enjoy entertaining, you'll love the spacious formal dining room with large bay window, open kitchen with stainless steel appliances, and a living room which flows into the separate den/sitting area with sliding glass doors to first floor deck, plus a cozy wood-burning fireplace at the center of it all. Half bath/powder room on lower floor and a large full bathroom on upper level with Jack & Jill entrance from primary bedroom. Samsung washer and dryer just 2 years young. Giant driveway with plenty of room for a boat, and an oversized 1-car garage with attic above, plus crawl space with concrete floors and approx 3 feet of head room for lots of storage and access to insulated oil tank. Roof is approx 10 years. Just under a quarter acre, fully fenced with newer PVC. Decking needs some love but large decks both from first floor and on upper level with sliding glass doors from primary bedroom. Property has significant elevation making flood insurance affordable. Ask me about the brand new bridge to Smith Point beach set to begin construction soon, or Brookhaven Town's planned and approved Downtown Revitalization Project, also set to begin construction soon just 2 miles away.

62 Lombardy Drive, 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
$549,900
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
$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
$155,000
1022018 MLS
Residential vacant land. Size 0.14 AC. Variance approved.

Trafalgar Drive, Shirley
$425,000
2 Beds ⋅ 2 Baths ⋅ 1018240 MLS
Enjoy resort-style living in this beautifully maintained 2-bedroom, 2-full-bath condominium located in a sought-after 55+ retreat-style community. Designed for comfort and convenience, this spacious home features a granite eat-in kitchen with sliders leading to a private balcony, perfect for enjoying your morning coffee or relaxing outdoors. The thoughtfully designed floor plan offers a spacious living room, separate den, and formal dining room, providing plenty of space for entertaining and everyday living. The generous primary suite serves as a private retreat, complete with a full en-suite bathroom and two walk-in closets. A well-appointed second bedroom and full guest bath provide comfort and privacy for family and guests. The convenience of in-unit laundry adds to the ease of everyday living. Beyond your front door, enjoy an exceptional lifestyle with outstanding community amenities. The stunning clubhouse features a state-of-the-art fitness center, library, business office, and an elegant banquet room complete with a private kitchen and bar, perfect for social gatherings and community events. Outdoors, residents can relax by the heated pool, enjoy scenic views of the lake, take advantage of paddle boating, or participate in the wide variety of activities and social events offered throughout the year. This is more than a home—it's a lifestyle. Don't miss the opportunity to enjoy luxury, convenience, and an active community in one exceptional package.

22 Cricket Court, Shirley
$190,000
1006388 MLS
Rare opportunity to own a spectacular bayfront property featuring 90 feet of direct waterfront frontage and private water access. Enjoy breathtaking panoramic views, stunning sunsets, and the tranquility of waterfront living. Whether you're looking to build your dream home, create a vacation retreat, or invest in a premier waterfront location, this property offers endless possibilities. With direct access to the bay, boating, kayaking, paddleboarding, fishing, and other water activities are just steps from your door. The generous waterfront frontage provides ample space to maximize views and take full advantage of the property's exceptional setting. Experience the beauty of coastal living with easy access to nearby beaches, marinas, dining, and local amenities.

VL Johns Neck Road, Shirley
$750,000
8 Beds ⋅ 3 Baths ⋅ 1001013 MLS
Expanded and versatile 8-bedroom, 3-bath home offering endless possibilities for extended family living or investment potential! Designed with a layout similar to a duplex this unique property features spacious living areas, beautiful wood floors, and gas cooking. This home was built with truss construction, giving you incredible flexibility to reimagine the layout and customize the floor plan to fit your needs. Whether you want open-concept living, expanded bedrooms, or a completely new flow, the possibilities are endless. The oversized primary bedroom offers a full-size hot tub, brand new updated bathroom creating a private retreat right at home. A full basement 12ft ceilings with 2 separate entrance provides exceptional storage and future potential. Generous room sizes, flexible floor plan, and ample space throughout make this property truly one of a kind. Conveniently located near shopping, transportation, parks, and major roadways. A 3 car detached garage ample storage and work space.Property being sold as-is Incredible opportunity with unlimited potential!

46 Brushwood Drive, Shirley
$499,999
4 Beds ⋅ 2 Baths ⋅ 998830 MLS
Check out this lovely 4 bedroom, 2 full bathroom home in Shirley, located within walking distance to the beautiful Smith Point Beach. In 1996, the home was enhanced with a second story addition, along with a new roof and new siding, and all Certificates of Occupancy are in place, offering peace of mind to the next owner. Step inside to find 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 for added convenience. Upstairs, you'll find a generously sized primary bedroom with a spacious sitting area, perfect for a private retreat, reading nook, home office, or relaxation space. An additional bedroom, a dedicated oversized laundry room, and a full bathroom featuring both a tub and a separate shower complete the second level. Outside, there is a storage shed providing additional space for tools, beach gear, and seasonal items. Enjoy the opportunity to live just a short walk from the renowned Smith Point Beach on the Fire Island barrier beach. A true haven for surfers, beachgoers, and outdoor enthusiasts, Smith Point offers white sandy beaches, rolling Atlantic waves, camping, fishing, scuba diving, swimming, food concessions, and a nationally recognized lifeguard headquarters. Ideally situated near shopping, dining, and everyday conveniences, with the Long Island Rail Road just 4 miles away, this home offers the perfect balance of coastal living and convenience. Whether you're looking for a year round residence or a peaceful retreat near the shore, you'll love the relaxed lifestyle, scenic surroundings, and welcoming atmosphere that make coming home a true pleasure.

55 William Floyd Parkway, Shirley
$499,000
3 Beds ⋅ 2 Baths ⋅ 990819 MLS
Welcome to this well maintained ranch style home located at 162 Parkwood Dr in Shirley, offering comfort, convenience, and a functional layout. This home features 3 bedrooms and 2 full bathrooms, a bright eat-in kitchen, and laminate flooring throughout the main living areas. Enjoy the warmth of a cozy fireplace and the convenience of an in unit washer and dryer. The property also includes a unfinished partial basement for storage or future potential, oil baseboard heating, and an attached garage. Step outside to a patio and a fully fenced yard, perfect for relaxing or entertaining. Conveniently located near shopping, schools, and the train station, making commuting and everyday living easy. A great opportunity to own a comfortable home in a desirable Shirley location, don’t miss it!

162 Parkwood 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
$1,439,900
3 Beds ⋅ 3 Baths ⋅ 975912 MLS
Welcome To Shirley NY. Come Live in Paradise... A Wonderful Beach Community .. Just 2 Minutes Away From The Famous Smiths Point Beach And Park offering Spectacular Sunrises with Spectacular Westerly Sunsets in your Back Yard... This is a Rehab that has been Completed better than New Construction... Seller welcomes Any Home Inspections... New 300 Amp Electric.. 4 Zone Air Conditioning and 4 Zone Heating... Home has been Converted to Propane... All new walls and floors which include Most floor joists and framing Studs being replaced. Most of the house is Spray in insulation... Garage is Extra Large with a little more with and depth with insulated Garage door... Crawl Space is poured Concrete with French drain. Off the Beautiful Front Porch you enter A Spacious Entry Hall with large Closet and Large 1/2 Bath... Expansive Kitchen comes with a Coffee Bar, 4 foot 7 Burner Gas Cook with Pot Filler. entertainers 19 Island with Wine Cooler, Trash Compactor and seating Area ... Spacious Master Bath is a Steam Shower Soaking Tub and Dual Vanities .... Home Has All CO's In Place. Everything was do with town Permits There is Wayyyyy to many upgrades to List. The Home is A Must See. .. Seller Will Hold A 1st Mortgage with 50% Down (at Market Rates) ....

72 Grandview Drive, Shirley
$485,000
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
$399,990
3 Beds ⋅ 1 Baths ⋅ 973025 MLS
Calling All Investors! 3 bedroom home with over 15 year tenant in place that would love to stay! Low taxes and all rental permits in place.. Be the 1st!

123 St George Drive E, Shirley
$649,000
4 Beds ⋅ 3 Baths ⋅ 967458 MLS
New Construction still time to pick colors and upgrades. Close to beach - shopping and much more. Property tax is vac land full assessment TBD

37-39 Harrison Road, Shirley
$89,999
942458 MLS
Residential vacant land.

Commack Road, Shirley
$89,999
L3579231 MLS
Design your dream home on this cleared 50x100 lot in a prime neighborhood! Enjoy the convenience of being just minutes from beaches, parks, shopping centers, and major highways. The property is sold as-is, without contingencies or building permits. Located next to 8 Maplewood Drive, Shirley, this is your chance to build in a sought-after location! All personal items will be removed upon closing.

Maplewood 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.