$541,685Average Value$359Average Price per Sq Ft60Homes 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?
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GreatSchools:
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On average, homes in Shirley, NY sell after 59 days on the market compared to the national average of 54 days. The median sale price for homes in Shirley, NY over the last 12 months is $535,000, up 6% from the median home sale price over the previous 12 months.
This spacious Colonial offers 4 Bedrooms with A bonus room ( could be used as office or 5th bedroom) and 2 Full baths. This home features A semi open floor plan, Kitchen with oak cabinets and Stainless steel appliances, Central Air and a ductless split, Anderson windows, Ceiling fans, In ground sprinklers, Beautifully landscaped fenced front and back yard, Shed with electric, beautiful brick
A rare layout designed with intention! This 3-bedroom, 2-full-bath Cape offers privacy, flow, and spaces that truly make sense for everyday life. From the moment you step inside, the bright, open living and dining area welcomes you with hardwood floors and recessed lighting, creating a warm, comfortable place to relax or gather with friends and family. The updated kitchen is the heart of the
This welcoming beach and boating community located two blocks away from the public bay beach and park is also near the famous Smiths Point Ocean Beach, Park, Fishing, Marina and Boat Ramp. When you arrive, pull right into the brand-newly paved asphalt double driveway with PVC gated access. The gate allows you to pull your vehicle, boat, or RV, right into the spacious backyard. There you will find
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
This spacious Colonial offers 4 Bedrooms with A bonus room ( could be used as office or 5th bedroom) and 2 Full baths. This home features A semi open floor plan, Kitchen with oak cabinets and Stainless steel appliances, Central Air and a ductless split, Anderson windows, Ceiling fans, In ground sprinklers, Beautifully landscaped fenced front and back yard, Shed with electric, beautiful brick
Welcome to this remarkable 3 bedrooms and 1.5 baths Center Hall Colonial featuring a comfortable and functional layout. The main level offers a large living room, formal dining room, eat-in kitchen with ample cabinet and counter space, and a cozy den with hardwood floors and a wood-burning fireplace. The second level features three bedrooms and a full bath. Additional highlights include a one-car
A rare layout designed with intention! This 3-bedroom, 2-full-bath Cape offers privacy, flow, and spaces that truly make sense for everyday life. From the moment you step inside, the bright, open living and dining area welcomes you with hardwood floors and recessed lighting, creating a warm, comfortable place to relax or gather with friends and family. The updated kitchen is the heart of the
Charming & Bright 2-Bedroom Home with Modern Upgrades!!! Step into this beautifully renovated 2-bedroom, 1-bathroom home, where natural light and modern comforts blend seamlessly. The inviting living room flows effortlessly into the updated kitchen, complete with a ductless AC/heating unit for year-round comfort. The first-floor bedroom offers flexibility as a home office, featuring a deep
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
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
Rare Lot, in North Shirley, you want to buy this house at 135 Forrest Avenue. A park-like property, beautifully updated 3-bed, 1-bath ranch on a generous 0.38-acre lot in the heart of Shirley. At 1,032 sq ft, this home blends modern upgrades with comfort and value, making it ideal for first-time buyers, downsizers, or anyone seeking a move-in-ready Long Island home with exceptionally low taxes.
Indulge in refined coastal living in this exceptional waterfront residence, fully renovated in 2024 and offering a private boat dock with direct access to the Great South Bay. This elegant 3-bedroom, 2.5-bath home seamlessly blends modern sophistication with timeless waterfront charm. The interior features expansive living spaces filled with natural light, including a gracious living room
Brand-new custom Cape Cod home offering East End living with a modern touch. Featuring hardwood floors throughout, a cozy living room with fireplace, and an eat-in kitchen complete with soft-close cabinetry, quartz countertops, stainless steel appliances, and a center island. The first floor includes a bedroom and full bath. Upstairs offers two additional bedrooms, a full bathroom, and a
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: 2208162Welcome to 469 Auborn Ave, a beautifully maintained 3-bedroom, 1.5-bath home offering comfort, convenience, and modern living in the heart of Shirley, NY. With approximately 1,400 sq. ft. of living space — including a versatile finished basement — this home provides plenty of room for relaxation, work, and entertainment.Step inside to find a bright and inviting
Welcome to this 3-bedroom, 1-bath ranch featuring an open floor plan with an eat-in kitchen and new stainless-steel appliances. Enjoy modern touches throughout, including a completely updated bathroom, new luxury vinyl wood flooring in the kitchen, hallways and bath, new carpet throughout and fresh interior paint from top to bottom. The home offers a spacious fenced in yard and a private driveway.
100% Fully Renovated 4 Bedroom 3 Bath House with Washer/Drying, Full Kitchen with Dishwasher and Separate Dining Room, Central Air, Oil Heat and One Car Garage on Large 3/4 Acre Fully Fenced in Lot. Located just off William Floyd, South of LIE and North of Sunrise Highway. Easy access to all Main Highways. Utilities, Oil and Landscaping Not Included. Interested Parties Only and NO Broker or
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.
Renovated 4-Bedroom Home for Rent in Mastic, NY at $3,995 a month, INCLUDES all utilities.House does not qualify for housing assistance programs. A renovated, move-in-ready single-family home offering 4 bedrooms and 1 full bathroom across approximately 1,078 square feet. This freshly painted residence blends modern updates with practical layouts to provide a welcoming space for
Cozy Cottage on 160 x 100 property which is including extra 40 x 100 lot .. basement great for storage and has washer/dryer hookup! .. gorgeous property! Be the 1st!, Additional information: Appearance:cozy,Interior Features:Lr/Dr,Separate Hotwater Heater:yes .. Owner requires credit report and proof of resources to pay rent.. Also landlord reference if possible.. Please do not disturb current
Small 2 bedroom house for rent. Fully renovated interior with a large fenced yard. Full unfinished basement. Finished attic space, good for a playroom or just for storage. Washer/Dryer hookup in the kitchen area. Owner will be taking care of the yard maintenance. Please have a credit report available with proof of resources to pay the rent and a landlord reference letter if possible. Tenant pays
Amy SchulerYour Team D&G Realty Ltd
$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
Walk Score® measures the walkability of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
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