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MLS ID KEY1041275Last updated Sep 25, 2026

Single Family

556 Windsor Avenue

Pending · Islip · Suffolk County, NY 11718

Bedrooms
4 Beds
Bathrooms
2 Baths
Year built
1902
Est. monthly taxes
$1,524.17
Property gallery0 / 49
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About this home

Welcome to 556 N Windsor Avenue, a gracious 1902 Colonial offering exceptional space, character and versatility in the heart of Brightwaters Village. From the moment you enter the charming entry parlor and continue into the welcoming foyer with its grand staircase, the home immediately draws you in with its warmth, character and inviting sense of space. Designed with entertaining and everyday living in mind, the main level offers beautifully proportioned spaces throughout. The oversized living room provides plenty of room for multiple seating areas and is anchored by a wood-burning fireplace with a beautiful mantel and custom built-ins. Crown and base molding, recessed lighting and architectural details add to the room's character, while multiple openings create an easy connection to the adjoining wraparound den. Filled with windows and natural light, the enclosed wraparound den offers an inviting space to relax and entertain and features built-ins, a bar area with wine refrigerator, an integrated sound system and direct access to the backyard. At the heart of the home is the spacious chef's kitchen with radiant heated floors, rich cherry cabinetry, quartz countertops, stainless steel appliances, a breakfast bar with pendant lighting and a six-burner Viking range with center grill and oversized hood vented to the exterior. The kitchen opens to the large dining room with hardwood floors, a bay window, tray ceiling and sliding glass doors to the deck and yard. Just off the kitchen, a convenient mudroom with radiant-heated tile flooring provides direct backyard access and incorporates a perfectly placed laundry nook with additional storage. Completing the main level is a beautifully updated full bath with a classic clawfoot tub, pedestal sink and timeless tilework, along with a generously sized office with extensive closet storage. Currently used as a home office, this versatile room also offers the flexibility of a possible fifth-bedroom or comfortable guest space. Upstairs are four bedrooms, including a spacious primary bedroom with separate sleeping and sitting areas, generous closet space and a decorative fireplace mantel. An oversized updated full bath with tiled shower completes the second level and pull-down stairs from the hallway provide convenient access to the attic for additional storage. The partial basement provides even more storage and includes a cedar closet and workshop area. Outdoors, the home's inviting living spaces continue with a wood deck, paver patio, large fenced yard and established organic vegetable and flower gardens, creating a wonderful setting for outdoor dining, entertaining, gardening or simply relaxing. A newly repaved Belgian block-lined driveway provides abundant parking and leads to the detached two-car garage. Additional features include central air conditioning, two-zone natural gas heat, public sewers and a multi-room sound system with indoor and outdoor speakers. Offering four bedrooms plus a flexible first-floor office/possible fifth bedroom and two full baths, this move-in-ready home brings together exceptional space, character and the sought-after Brightwaters Village lifestyle. Enjoy close proximity to Wohseepee Park, Village shopping and dining, schools and major roadways, along with resident amenities including the Village beach, canal docking, Brightwaters lakes, tennis, dog park, private garbage collection and snow removal. Just minutes from Downtown Bay Shore, the Fire Island Ferries and Robert Moses State Park, 556 N Windsor Avenue offers the opportunity to enjoy all that Brightwaters and the Great South Bay lifestyle have to offer.

Listing snapshot

Days on site
49 days
Listed on MLS
Sep 3, 2026
Full baths
2
Half baths
0
Annual property tax (MLS)
$18,290
Tax year
2026
Area source (MLS)
Public Records
Listing brokerage
Signature Premier Properties
MLS ID
KEY1041275
Last updated
Sep 25, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
1902
Garage
Yes
Garage spaces
2
Parking
Driveway, Garage, Private
Water source
Public
Sewer
Public Sewer
Utilities
Cable Available, Electricity Connected, Natural Gas Connected, Phone Connected, Sewer Connected, Trash Collection Private, Water Connected

Interior features

Basement
Crawl Space, Partial, Storage Space
Heating
Natural Gas, Radiant Floor
Cooling
Central Air
Interior
First Floor Bedroom, First Floor Full Bath, Built-in Features, Chefs Kitchen, Crown Molding, Eat-in Kitchen, Entrance Foyer, Formal Dining, Open Kitchen, Sound System, Speakers, Storage, Tray Ceiling(s), Washer/Dryer Hookup, Wired for Sound
Appliances
Dishwasher, Dryer, Exhaust Fan, Freezer, Gas Oven, Gas Range, Refrigerator, Stainless Steel Appliance(s), Washer, Gas Water Heater
Flooring
Carpet, Ceramic Tile, Tile, Wood
Fireplace
Yes
Fireplaces
1

Exterior features

Architectural style
Colonial
Construction materials
Shingle Siding
Exterior
Garden
Private pool
No

Schools (MLS)

Elementary school
Mary G Clarkson School
Elementary school district
Bay Shore
Middle school
Bay Shore Middle School
Middle school district
Bay Shore
High school
Bay Shore Senior High School
High school district
Bay Shore

School information is provided by the MLS. Confirm attendance eligibility with the school district.

Recent activity

  1. Listing updated from MLS
  2. MLS status changed
  3. First seen on this site

Location

Islip · Suffolk County, NY 11718Show interactive map
556 Windsor Avenue

Islip · Suffolk County, NY 11718

Google Maps directions

Estimate monthly payment

Loan detailsFixed-rate, fully amortizing loan. Edit the assumptions below; no market rate is supplied.
Property expenses (USD)
MLS amounts are prefilled when available and can be edited. Confirm what fees include. Unknown fee frequencies cannot be converted automatically.Property expenses: MLS values where available; missing values stay blank.

Estimated monthly principal & interest—

Monthly property taxNot provided

Monthly association / maintenance feesNot provided

Estimated monthly total of entered costs—

Excludes insurance, mortgage insurance, special assessments and lender fees. MLS taxes may reflect abatements or exemptions and can change.

Listing data is supplied by the MLS and may change without notice.