$539,253Average Value$356Average Price per Sq Ft55Homes For Sale
Hamlet known as Long Island’s Best Kept Secret
At the top of the 20th century, Shirley was a popular getaway for a few New York City elites. “Walter T. Shirley owned this beautiful mansion there off the water, and that’s where he would entertain socialites and movie stars like Tony Bennett and Marilyn Monroe,” says Ted Gounelas, an associate broker with Coldwell Banker M&D Good Life who grew up in the area. “That happened before the Hamptons, so I don’t want to say it was the original Hamptons, but it’s basically the Hamptons that never were.” In the 1960s, Walter T. Shirley then developed the community as a collection of bayside bungalows for working-class families. Today, the hamlet on Long Island's South Shore carries on his surname — and his vision. “It’s the last affordable waterfront community,” says Tina Jahrsdoerfer, a licensed real estate salesperson at Signature Premier Properties who has lived in the neighborhood for 29 years and has sold homes here for 10 years. “You can get waterfront property for less than $1 million here, which is unheard of — and actually, a lot less than that.”
Even for those who don’t live on the water, the beach is often only a short drive or bike ride away. “People love being right by the beach,” Jahrsdoerfer says. “Shirley is kind of big. But if you live south of Montauk, you’re only 5 miles from the beach, right down the road. You can hop on your bike and ride over there, which people like because then you don’t have to pay for parking. That’s what I usually do. People who live on those canal streets, they can just walk over the bridge.” Home to just under 26,500 people, Shirley offers access to the natural beauty of Long Island and the urban amenities of New York City, about 70 miles away. The hamlet also embraces the spirit of its motto “Long Island’s Best Kept Secret.” “I tell people all the time. My mother lives in Upstate New York, that’s too little. The city, that’s too much. Long Island is just perfect,” says Andrew Chrzanowski, team leader of the Manhattan to Montauk Group with Real Broker NY.
Shirley's various neighborhoods have easy access to the water.
Wertheim National Wildlife refuge is a great place to hike and see various bird life.
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Fishing, boating and swimming in Bellport Bay and on Fire Island
Shirley embraces its waterfront location, with opportunities for fishing, boating and swimming. “Everywhere you look, we have a fishing pier,” Jahrsdoerfer says. “We never have to buy clams or crabs because if we’re in the mood for them, my husband just buys chicken legs, grabs the traps and gets them.” On the edge of Bellport Bay is Shirley Beach, which features a sandy beachfront, playground and splash pad. “I bring popsicles down there while the kids hang out and go to the splash park to cool off,” Jahrsdoerfer says. Those looking to get out on the water can head to the boat ramp at Smith Point Marina County Park. The 2,550-acre Wertheim National Wildlife Refuge stretches into the western half of Shirley and is a popular spot for hiking, wildlife watching and paddle boating on the Carmans River.
The hamlet is also home to the Long Island Skydiving Center. “I was driving down William Floyd Parkway with my daughter the other day and there were six parachuters coming down,” Jahrsdoerfer says. The Smith Point Bridge connects residents to the eastern end of Fire Island, where Smith Point County Park is a haven for beachgoers on the Atlantic Ocean. There’s also live music in the park every weekend throughout the summer at Tiki Joe’s Beach Club. After undergoing a $26.7 million renovation project, the Mastics-Moriches-Shirley Community Library reopened in 2024 and continues to support the Tri-Hamlet area with educational and recreational programming for all ages. Shirley sees all four seasons, with humid summers and relatively mild winters.
Take a boat out from Smith Point Marina through Narrow Bay or Bellport Bay en route to the Ocean
Take a boat out from Smith Point Marina through Narrow Bay or Bellport Bay en route to the Ocean
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Shirley offers comparative affordability on Long Island
A variety of architectural styles complement the hamlet’s waterfront location. “In the 1950s and ‘60s, this area was full of bungalows and summer homes for people in the city. As more people started moving to Long Island, those bungalows became full-time homes,” Chrzanowski says. “Some of the homes are still the original bungalows, and then there are also some ranch-style houses and Capes.” Those looking for newer construction will find properties built from the 2000s through the early 2020s. “There’s more space out this way, so they’re building a lot of newer homes. Most of those are Colonials,” Chrzanowski says.
Comparative affordability is a big draw for homebuyers in Shirley. The median price of single-family homes is $505,000, significantly less than the median sales price of over $700,000 across all of Long Island. “Where else are you getting that?” Jahrsdoerfer asks. “You’re not getting that anywhere else, and you’re looking right out your bedroom window at the canal. The waterfront lifestyle is here just like it is anywhere else that’s more expensive; it’s just more affordable, and the taxes are lower.” Homes right on the bay can fetch up to $1.4 million, and flood insurance is a must for residents who live along the waterfront. Shirley’s overall CAP Index crime score is 3 out of 10, lower than the national average of 4.
Plenty of dock space for your boat or jetski, right in your backyard.
Spacious ranch home on the canal.
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Top-rated school districts, nearby community college and Stony Brook University
Shirley is split between two school districts. The William Floyd Union Free School District serves the southern three-quarters of the hamlet, while the Longwood Central School District covers the northern quarter. Both school districts earn an overall grade of A-minus from Niche. Nearby options for higher education include Suffolk County Community College, which is less than 15 miles away and serves more than 20,000 students. Residents are also around 25 miles from Stony Brook University, which Niche ranks as the fourth-best public university in the state. “One of the big draws to Long Island is Stony Brook University,” Chrzanowski says. “It’s a top-rated university, and your kids can still live at home without paying for dorms and all of that stuff.” SCCC and SBU are part of the State University of New York system.
NID 537933 Longwood Sr. High School has a fairly large campus with many well maintained fields.
William Floyd High School has one of the largest school campus in the area.
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Events in the Tri-Hamlet area include the Annual Christmas Parade
Shirley, Mastic and Mastic Beach are three intertwining hamlets known together as the Tri-Hamlet area. Residents from all three communities come together for annual events hosted by the Mastics & Shirley Chamber of Commerce. Popular festivities include the Food Truck Rally & Car Show and the Annual Christmas Parade, which brings more than 6,000 people to the hamlets each year and stands out as the largest Christmas parade in the Town of Brookhaven. Locals can also join community organizations like the Tri-Hamlet Mom’s Group.
Get an early start on your Christmas shopping at the Christmas Craft Fair.
Enjoy some live music at the North Meets South Fair.
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Commercial corridors along William Floyd Parkway and Sunrise Highway
Shopping and dining are concentrated in the heart of Shirley along William Floyd Parkway and Sunrise Highway. Residents will find a mix of shopping centers, chain retailers and local restaurants lining both thoroughfares. “As far as dining goes, there’s pretty much every type of food you can think of,” Chrzanowski says. “They just put in this amazing brewery called Southpaw, and they actually fill your beer from the bottom up. It seems like the beer is just better that way.” For more shopping and dining, residents can head to the Tanger Outlets Riverhead, one of the largest outlet malls on Long Island, with more than 130 retailers.
Access to the Long Island Expressway, LIRR and NYC commutes
In addition to shopping and dining, William Floyd Parkway and Sunrise Highway are Shirley's main transportation routes. William Floyd Highway provides access to Interstate 495, which runs along the hamlet’s northern edge. Also known as the Long Island Expressway, I-495 leads about 70 miles west into New York City. Those who prefer to take public transportation can head to Mastic-Shirley station, where the Montauk Branch of the Long Island Rail Road connects commuters to Manhattan’s Penn Station in about an hour and 45 minutes. For air travel, Long Island MacArthur Airport is about 13 miles away, and USA Today ranks it as the third-best small airport in the country. The closest international airport is John F. Kennedy International Airport, about 53 miles from Shirley.
Written By
Sally Stimpson
Photography Contributed By
Joseph Popovich
Video By
Mark Tilley
Interested in learning more about homes in this area?
Reach out to
Mario Arias,
an experienced agent in this area.
GreatSchools:
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On average, homes in Shirley, NY sell after 57 days on the market compared to the national average of 55 days. The median sale price for homes in Shirley, NY over the last 12 months is $535,000, up 4% from the median home sale price over the previous 12 months.
Move right in and enjoy true peace of mind in this beautifully updated 3 bedroom, 2 bath colonial where the big-ticket items are already taken care of. Recent 2025 improvements include a new roof, gutters, windows, two fully renovated bathrooms, and a brand new oil burner with a double-walled oil tank. These are the kind of updates buyers love knowing are already done. And just when you thought
Great home quiet street great condition home offers open but formal layout hardwood floors big kitchen 3 Bedroom up with giant hallway walk in closet. Nice size yard nice front porch large Basement unfinished. Home has Oil heat Separate water tank CAC unit needs work.
New to the market is 42 Pinetop Drive in Shirley, a charming Ranch nestled back on an oversized, fully fenced flat lot with the luxury of a circular driveway. Very convenient floor plan throughout. The Primary Bedroom is tucked privately away from the main house and has it's own exclusive access to the backyard. Huge closets and storage, meticulously maintained appliances, furnace, kitchen and
Opportunity awaits in the Shirley Beach area! Welcome to this 3-bedroom, 1 bath home set on 1/3 of an acre, where coastal living meets everyday convenience. Just minutes from Smith Point Beach, you’ll love having the ocean, marina, and local favorites right at your fingertips This is a true fixer-upper and requires a full clean-out, but for the right buyer, the potential here is HUGE. Whether
Move right in and enjoy true peace of mind in this beautifully updated 3 bedroom, 2 bath colonial where the big-ticket items are already taken care of. Recent 2025 improvements include a new roof, gutters, windows, two fully renovated bathrooms, and a brand new oil burner with a double-walled oil tank. These are the kind of updates buyers love knowing are already done. And just when you thought
8 George Drive offers five bedrooms and three full bathrooms with exceptional space and versatility. The first floor features two bedrooms, two full baths, and an open-concept kitchen, dining, and living area, plus an expansive enclosed breezeway providing flexible additional living space. A fully legal accessory apartment upstairs offers ideal options for rental income or extended family.Set
Great home quiet street great condition home offers open but formal layout hardwood floors big kitchen 3 Bedroom up with giant hallway walk in closet. Nice size yard nice front porch large Basement unfinished. Home has Oil heat Separate water tank CAC unit needs work.
Cape cod with views of great sough bay, amazing sunsets, Hardwood floors, custom fenced in front and side yards, w. Tall decorative grasses pines, and paved walkways outdoor shower and oasis like large back yard with decking pavers fruit trees, pool and spa hot-tub. Outdoor TV set Pergolas, sheds and plenty of seating. Double gated driveway, and additional off street parking. Expansive open
Beautifully redone ranch featuring a spacious living room, formal dining area, and eat-in kitchen.Updated electical 200 amp service. Enjoy the convenience of an in-home washer and dryer, plus a full security system for peace of mind. This cozy and comfy home is truly move-in ready - just drop your bags and start living!!
Prime corner lot opportunity on a busy road with an average of 10,000 cars passing by each day! This .18-acre parcel offers excellent visibility and accessibility, making it ideal for a wide range of development possibilities. Whether you’re looking to build a retail space, office, or service-based business, this property provides strong exposure in a high-traffic area. Don’t miss out on this
New to the market is 42 Pinetop Drive in Shirley, a charming Ranch nestled back on an oversized, fully fenced flat lot with the luxury of a circular driveway. Very convenient floor plan throughout. The Primary Bedroom is tucked privately away from the main house and has it's own exclusive access to the backyard. Huge closets and storage, meticulously maintained appliances, furnace, kitchen and
Investor Special / Full Rehab Opportunity! 3 Bedroom, 2.5 Bathroom Expanded Cape situated on an oversized lot. This home has been completely gutted to the studs and is ready for your vision—ideal for investors, builders, or end-users looking to create a custom home from the ground up. The existing footprint includes a full basement and offers flexibility for redesign, expansion, or potential ADU
Built in 1980, this well-maintained 850 SF 2-bedroom ranch is ready to welcome its next owner. Featuring hardwood floors throughout, ductless AC units, and recessed lighting, this home offers a simple, easygoing lifestyle. A full, unfinished basement provides additional storage. Step outside to enjoy your new inviting front porch or your fully fenced backyard, perfect for the ultimate relaxation.
LIVING LUXURY In The Heart Of Shirley! Hamptons Inspired, Home Is Nestled On A Lush .21 Acre Property. Completely Renovated With A Bright, Airy, Open-Concept Layout Offering Over 1,800 Sq Ft Of Space Across Three Levels. Sleek Designer Finishes And Oversized Windows Set The Tone From The Moment You Enter. Euro-Modern Eat-In Kitchen Features Stainless Steel Appliances, Quartz Countertops. Bright
Welcome to this beautifully updated home offering modern upgrades, flexible living space, and year-round comfort.This move-in ready property features a newly renovated kitchen designed for both style and functionality, complete with sleek quartz countertops, a dedicated coffee bar, and a gas stove, perfect for everyday cooking and entertaining. The living room has been refreshed with new
Welcome to this charming cape in the heart of Mastic Beach! This 3 bedroom, 1 bathroom residence features durable vinyl flooring throughout and a functional walk-through kitchen equipped with an electric range and plenty of cabinet space. The home has been thoughtfully cared for, boasting a roof less than 5 years old, a recently serviced electrical panel, and a furnace that is serviced annually
Beautiful second-floor apartment offering two bedrooms and a full bathroom. Open N Bright - Enjoy a private driveway, front porch, private yard with shed, and modern stainless-steel appliances..
Property Id: 2353044Enjoy a relaxing stay in Shirley, NY, just minutes from Smith Point Beach This retreat features a private entrance for comfort and privacy, with quick access to sandy shores, nature trails, and the Fire Island Wilderness. After a day of sun and surf, unwind in your own space or explore local dining options like diners, sushi, and beachside spots with live music.
2 Bedroom Apartment for Rent – Shirley, NY (Available Immediately)Spacious and well-maintained 2-bedroom, 1-bath apartment located in a quiet private house in Shirley. This second-floor walk-up offers comfortable living with access to a huge shared yard, perfect for relaxing or enjoying outdoor space.Features include:+Bright 2-bedroom, 1-bath layout+Second-floor walk-up in private
Property Id: 1844318Welcome to your large master bedroom with private bathroom room in Shirley, NY! features modern amenities including a dishwasher, security system, and off-street parking. 10 Min driving to St. John’s Univ. and Suffolk CC Ideal for students or working professionals looking for a clean, quiet place near campus.Enjoy the convenience of included utilities and
This home has been updated from top to bottom and offers space and privacy. The open living room features a stunning cathedral ceiling and hardwood floors. The kitchen shines with stone countertops and stainless appliances, plus a dishwasher. You’ll also love the convenience of an in-unit washer/dryer, attic storage, and a fenced backyard that feels truly private.
Charming & Spacious Expanded Ranch – Available March 31st! Location: Shirley, NY 11967 Description:Enjoy spacious living in this beautifully expanded one-family ranch, perfectly situated on a generous half-acre lot. This home offers 1,531 square feet of interior living space, providing a comfortable and open layout for you and your family. Key Features:3 Bedrooms / 1 Full
$3,800 per month
3 Beds
1.5 Baths
1,032 Sq Ft
Welcome to this beautifully maintained ranch home located in the desirable Mastic Acres section of Shirley. This property offers comfort, functionality, and a spacious layout perfect for everyday living and entertaining.The home features a bright and open living room, an updated eat-in kitchen with island, and a dedicated dining area. The main bathroom includes a jacuzzi tub and a separate
Open and spacious, luxury rental. This year round property boasts an open floor plan, large laundry room on the main floor, custom kitchen and lots of storage. Oversized balcony from kitchen and master suite give views to the water, where there is dock access. Walk-in closets, seamless drain shower, and vaulted ceilings are just a few of this homes many upgrades. Home comes furnished
Ask About Our Outstanding Specials*. $99 Security Deposit Special. Restrictions apply* Ranch, Duplex & Villa Style Townhomes For Those 55+.Each Private Entry Home Features 2 Bedrooms & 2 Baths, Large Closets & Terraces, Gourmet Tuscany Eat In Kitchens W/SS Appl. Clubhouse With A Social Hall, Health Center & Outdoor Pool! Pet Friendly! Prices/policies subject to change without notice
Ask About Our Outstanding Specials*. $99 Security Deposit Special. Restrictions apply* Ranch, Duplex & Villa Style Townhomes For Those 55+.Each Private Entry Home Features 2 Bedrooms & 2 Baths, Large Closets & Terraces, Gourmet Tuscany Eat In Kitchens W/SS Appl. Clubhouse With A Social Hall, Health Center & Outdoor Pool! Pet Friendly! Prices/policies subject to change without notice
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