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$3,999,000
3 Beds ⋅ 3 Baths ⋅ 1032772 MLS
SPECTACULAR 2.75-ACRE WATERFRONT CONTEMPORARY ESTATE A truly rare opportunity to own an extraordinary privately gated 3,800 sq. ft. waterfront estate set on 2.75 breathtaking acres with over 1,000 feet of bulkhead and spectacular water views. Step through the grand double glass doors into a stunning open-concept interior featuring soaring windows, beautiful ceramic flooring, and a magnificent chandelier overlooking the water. The home offers 3 bedrooms, 3 bathrooms, a second-floor loft, dining room, living room with fireplace, and a 3-car garage.The fabulous chef’s kitchen features custom wood cabinetry, a large granite island, and professional Wolf and Verona stainless-steel appliances. The luxurious primary en-suite offers a spa bath, walk-in closet, glass doors with balcony and deck with bay views, elevator access, along with a convenient second-floor laundry room. The waterfront lifestyle is truly exceptional, offering over 1,000 feet of bulkhead, a large boat slip accommodating two 65-foot yachts, a boat ramp, and a dedicated cut-out for multiple jet skis. A spacious boathouse and waterfront gazebo provide the perfect setting for enjoying the water, while a beautiful patio and pergola create an ideal space for outdoor entertaining and relaxation. Take in breathtaking sunsets with picturesque views of the Robert Moses Bridge. Additional amenities include a full-house generator, 27-zone sprinkler system, and an on-demand tankless hot water heater. Perfectly positioned approximately 60 minutes by LIRR to NYC for world-class dining, entertainment and shows, and approximately 60 minutes to the Hamptons and its renowned wineries. From your own home or the nearby local ferries, enjoy a quick 20 minute ride to Fire Island's Ocean Beach and other sought after destinations, where you can spend the day exploring charming shops, enjoying waterfront dining and live music, or relaxing on the beautiful white sand beaches. It's the perfect blend of waterfront living, convenience, and the quintessential Fire Island lifestyle. Conveniently located near shopping, transportation and everyday amenities. A magnificent waterfront estate. An extraordinary lifestyle. A rare opportunity. Call today for your private showing.

170 S Penataquit Avenue, Bay Shore
$1,599,000
6 Beds ⋅ 4 Baths ⋅ 1045401 MLS
Lovingly restored and thoughtfully enhanced by its current owners, this remarkable 1880 residence reflects years of careful stewardship And substantial investment. Every update was made to elevate everyday living while honoring the home's character and architectural integrity. Updates: 2021 : New Siding & Windows, New PVC & Aluminum Fencing. Leaf Filter on All Gutters 2021/2022 : Basement waterproofed ( Lifetime guarantee ) 2021/2022 : Pool heater & Filter 2022 : New Split Units 2023: Generator, 15 zone Sprinklers, Alarm system with 11 Cameras hooked up to Central Station, Doors 2024: New Kitchen & Appliances, Motorized Shades in Living Room 2025: New driveway, New walkway and Stoops 2026: 2.5 New Bathrooms, with Soaker tub on 2nd floor and wonderful shower on third floor 2026: Newly sealed bricks around pool and back walkway.

75 S Penataquit Avenue, Bay Shore
$2,000,000
9 Beds ⋅ 9 Baths ⋅ 1040354 MLS
Rare Waterfront Investment Opportunity On Penataquit Canal! This Exceptional Home Offers Over 180 Feet Of Prime Waterfront With 13 Private Boat Slips, Expansive Docking, And Breathtaking Views Of Fire Island. Situated At The End Of A Quiet Cul-De-Sac, This Unique Property Features A Total Of 9 Bedrooms And 9 Bathrooms, Including 5 Bedrooms With Private En-Suite Baths. Step Outside To A True Waterfront Oasis Featuring An In-Ground Pool With An In-Ground Hot Tub, A Stunning Brick Outdoor Kitchen, Expansive Paver Patio, And Swaying Palm Trees, Creating The Ultimate Resort-Style Setting For Entertaining Or Relaxing Along The Water. Whether You're Looking To Expand Your Investment Portfolio, Generate Exceptional Rental Income, Or Own A One-Of-A-Kind Waterfront Property With Endless Possibilities, This Incredible Offering Checks Every Box. A Rare Opportunity To Own A High-Income Producing Property In An Unbeatable Waterfront Location.

64 Mowbray Avenue, Bay Shore
$1,788,000
5 Beds ⋅ 6 Baths ⋅ 1038627 MLS
Welcome to 16 S Montgomery Ave, a spacious and beautifully designed home offering 5 bedrooms and 5.5 bathrooms. The first-floor features 1 bedroom and 1.5 bathrooms, along with a kitchen, living room, and dining area. The second floor offers 4 bedrooms and 4 full bathrooms, providing exceptional space and privacy. Additional highlights include central heating and cooling, generous room sizes, abundant natural light, and a functional layout ideal for everyday living and entertaining. A wonderful opportunity for buyers seeking space, comfort, and convenience.

16 S Montgomery Avenue, Bay Shore
$1,200,000
4 Beds ⋅ 3 Baths ⋅ 1032680 MLS
Welcome to this exceptional 4 bedroom, 2.5 bath Colonial, fully renovated to offer a sophisticated blend of modern luxury, thoughtful design, and effortless living south of Montauk. Built in 2013, the home features radiant heat flooring throughout, including the oversized one-car garage, along with two gas fireplaces that bring warmth and character to the living spaces. The main level offers a beautifully designed layout with a bedroom, separate den and living room, and an impressive kitchen appointed with high-end appliances and finishes, including two ovens for effortless entertaining. Upstairs, the king-sized primary bedroom is a true retreat, complete with its own gas fireplace, a beautifully appointed full primary bathroom, and an exceptionally spacious custom closet offering abundant storage. Two additional bedrooms complete the second level, providing plenty of space for all. Outdoors, enjoy a natural gas BBQ setup ideal for summer entertaining, along with the added privacy of having no backyard neighbors. Every element of this home has been carefully considered, from its elevated finishes and generous room sizes to the comfort and functionality of its floor plan. Ideally situated south of Montauk, this stunning residence delivers exceptional quality, privacy, and a refined South Shore lifestyle.

121 Bayway Avenue, Bay Shore
$2,200,000
10 Beds ⋅ 7 Baths ⋅ 1037620 MLS
Step back in time and experience the grandeur of this extraordinary 1850 Victorian estate, a truly one-of-a-kind residence where timeless architecture, remarkable scale, and old-world craftsmanship create something rarely found today. Set on 1.64 breathtaking, park-like acres, this magnificent property offers exceptional privacy, an inground pool, and endless possibilities. From the moment you enter, soaring ceilings, intricate crown moldings, beautiful hardwood floors, and exquisite period details capture the elegance and charm of a bygone era. Three expansive floors of living space feature a magnificent living room, grand banquet-sized formal dining room, large eat-in kitchen, and an inviting den with fireplace. The main residence offers an impressive ten bedrooms, seven full baths, and a full basement, providing extraordinary space and versatility. The estate also features a separate back house offering four additional bedrooms, two full baths, and a two-car garage, adding another remarkable dimension to this unique property. Rich in history and overflowing with character, this exceptional Victorian estate presents a rare opportunity to restore, reimagine, and create something truly spectacular. From its grand interior spaces to its sprawling grounds and resort-style pool, this is more than a home. It is a piece of history waiting for its next chapter. Make this extraordinary one-of-a-kind estate yours.

45 S Penataquit Avenue, Bay Shore
$2,000,000
1035730 MLS
Rare Waterfront Investment Opportunity On Penataquit Canal! This Exceptional Triplex Offers Over 180 Feet Of Prime Waterfront With 13 Private Boat Slips, Expansive Docking, And Breathtaking Views Of Fire Island. Situated At The End Of A Quiet Cul-De-Sac, This Unique Property Features A Total Of 9 Bedrooms And 9 Bathrooms, Including 5 Bedrooms With Private En-Suite Baths. Step Outside To A True Waterfront Oasis Featuring An In-Ground Pool With An In-Ground Hot Tub, A Stunning Brick Outdoor Kitchen, Expansive Paver Patio, And Swaying Palm Trees, Creating The Ultimate Resort-Style Setting For Entertaining Or Relaxing Along The Water. Whether You're Looking To Expand Your Investment Portfolio, Generate Exceptional Rental Income, Or Own A One-Of-A-Kind Waterfront Property With Endless Possibilities, This Incredible Offering Checks Every Box. A Rare Opportunity To Own A High-Income Producing Property In An Unbeatable Waterfront Location.

64 Mowbray Avenue, Bay Shore
$1,099,999
3 Beds ⋅ 3 Baths ⋅ 1032442 MLS
Enjoy Luxury Living in this 2222 Square foot (approx.) meticulously maintained Ranch home with its own deeded dock slip, that can fit a 10' Beam, perfectly located directly across the street. With convenient water access and water views, this is must see property. This home has been raised and sits on a spacious .46-acre lot in a quiet cul-de-sac, with beautifully landscaped front and side yards. This home features comfortable one level living with water views from some rooms and the spacious Trex deck with an electric awning and deck speaker. Upon entering the front door, just off the main foyer, the home features a dedicated pub room with sink and beverage refrigerator, creating the perfect space for entertaining. The very spacious 420' (approx.) chefs kitchen features radiant heat flooring, a commercial grade DCS, 5-burner gas range, a very large center island, a pantry, plenty of counter space and cabinets, two sinks w/garbage disposal, a drawer microwave, double drawer dishwasher and stainless appliances. There is a spacious living room with a gas fireplace and built in ceiling speakers. Adjoining, is a beautiful sun room with entrance to the deck. Down the hallway is the Laundry nook, two bedrooms and a redone full bath. At the end of hallway is the redone ensuite, shiplap wall in the primary, with a full bath and a step-in closet. There are High Hat lights throughout most of home. An additional feature is a young 2-car detached heated garage, with a 200amp electric panel, a workbench and sink. A circular driveway was just top coated and sealed. The house features a whole house generator with an automatic transfer switch. The generous deck backyard offers plenty of room for outdoor gatherings, gardening, or future enhancements. Interior highlights include hardwood flooring, bright living spaces, and a functional floor plan that provides both comfort and flexibility. Sip your beverage on the deck or at the kitchen table…while your mind is afloat, gazing at the water, where your boat slip is! Do not miss this rare opportunity for premier Long Island living.

6 Montgomery Lane, Bay Shore
$2,400,000
1032073 MLS
Prime Location in Downtown Bay Shore, Commercial Mixed-Use Building Approx. 14,000 sq ft, on a Half-acre Lot, Zoned BD with many uses. First Floor Open Space with Office and Bathroom. Second Floor, 3 Large Bedrooms, Living Room, Kitchen, 2 Full Baths. 3rd Floor Huge Open Attic Space, Fenced Property.

193 W Main, Bay Shore
$1,349,000
4 Beds ⋅ 3 Baths ⋅ 1018121 MLS
A rare opportunity to own a piece of Long Island’s South Shore history! This 4 bedroom, 2.5 bath Dutch Colonial was originally a carriage house for one of the large estates on the South Saxon peninsula and was built in 1900. Property offers complete privacy on park-like grounds and is perfect for entertaining in all seasons. Original flooring, original wood-burning fireplace and beautiful touches such as large Anderson windows, wide moldings, paneled wooden doors, antique hardware and custom window treatments. Spacious kitchen features custom cabinetry, butcher block countertops, a Sub Zero refrigerator, new dishwasher, and a Wolf commercial gas stove with a Viking exhaust hood. The large formal living and dining rooms offer cozy spaces for gatherings with family and friends. The family room features large Anderson sliding doors leading to the outdoor area. The primary suite features a vaulted ceiling with large picture windows leading to a small deck with a mechanical awning. The ensuite bathroom features a stall shower and a large soaking tub. All bedrooms have spacious closets. The outdoor area features a large brick patio, an in-ground saltwater pool, beautiful perennial gardens and a full outdoor shower. Detached two-car garage has a complete room upstairs with heat and A/C. Brand new driveway, gas heating system and updated roofing. A true gem!

10 Boyd Avenue, Bay Shore
$1,500,000
2 Beds ⋅ 2 Baths ⋅ 1011815 MLS
Welcome to Admiralty, a luxury gated community this beautifully appointed waterfront residence, where boating, private beach access, and resort-style living creates an exclusive coastal lifestyle.This beautifully appointed 2-bedroom residence showcases elegant imported flooring, soaring cathedral ceilings, and a breathtaking living room centered around a warm and inviting fireplace. The spacious gourmet kitchen is designed for both everyday living and entertaining, featuring premium stainless-steel appliances, a stylish bar area, and an open, sophisticated layout. The primary suite offers a private spa-like bathroom and with two walk-in closets, while additional features include a washer and dryer, ample storage, a spacious garage, and attic space. Step outside to your private patio, perfect for hosting family gatherings or enjoying peaceful outdoor living. Boating enthusiasts will appreciate the deep-water marina with private dockage and direct access to the Great South Bay. Situated within a meticulously maintained 158-acre waterfront community, residents enjoy an unparalleled lifestyle with 24/7 gated security, a newly renovated clubhouse, fitness center with Pilates and other wellness classes, three tennis courts, a pickleball court, private gardens, kayaking, a private beach, and a resort-style swimming pool with lifeguards. Perfectly positioned across from Fire Island’s Kismet and Ocean Beach and just a short drive to the Hamptons, this rare offering delivers the ultimate blend of luxury, recreation, and waterfront elegance. It includes snow removal, grass mowing and outside maintenance.Conveniently located near public transportation and supermarkets for easy everyday living.Just minutes from Bay Shore, offering access to shopping, dining, waterfront parks,less than two miles from ferry terminals to fire island and only one hour from NYC via LIRR. Don't miss out. https://theadmiraltyhoa.org

202 Captains Way, Bay Shore
$2,100,000
1007856 MLS
Bayfront lot plus boat basin With Brand New Bulkheading. Taxes are $6805.60 for bayfront lot (.73 Acres) and $3062.52 for Boat Basin (.46 Acres) Total $9868.12

Lot 4 and Lot 11 Overlea Court, Bay Shore
$1,600,000
1007846 MLS
Bayfront Lot With Brand New Bulkheading.

Lot 5 Overlea Court, Bay Shore
$1,800,000
1007814 MLS
1.22 Acre Bayfront lot with Brand New Bulkheading

Lot 6 Overlea Court, Bay Shore
$1,499,990
5 Beds ⋅ 4 Baths ⋅ 1001324 MLS
Nestled on Long Island’s coveted South Shore in desirable Bay Shore, this stunning five-bedroom ranch offers luxury living with a true resort-style feel. Beautifully landscaped grounds create a private backyard oasis featuring an Olympic-size swimming pool, expansive patio for entertaining, and a lighted professional tennis court for day or evening play. Inside, the home blends comfort and sophistication with an oversized family room ideal for gatherings, a sunroom showcasing panoramic yard views, and a chef’s kitchen featuring premium appliances, including a full-size Sub-Zero refrigerator and separate full-size Sub-Zero freezer with abundant storage. Recent upgrades include a Brand New sprinkler system, owned solar panels, a renovated double shower in the primary suite, updated heating and A/C in the kitchen, and a newly installed 5-ton central A/C unit. An upper-level bedroom with a private roof deck overlooks the pool and tennis court, completing this exceptional Bay Shore retreat. A rare opportunity to enjoy luxury, recreation, and effortless South Shore living.

9 Dove Lane, Bay Shore
$1,200,000
4 Beds ⋅ 3 Baths ⋅ 993496 MLS
West Bay Shore new construction! Shy 2,800’ sq. 4 bedroom colonial. All oak floors in large rooms. Shaker style / stainless kitchen w/ breakfast bar. Rainforest shower in large en-suite. Gas heat, central air. In ground sprinklers. Huge walkout basement. Nothing to do but move in. Taxes reflect partial assessment. See attached link for pics. https://sites.allmediatours.com/mls/245140546

969 Manor Lane, Bay Shore
$1,875,000
9 Beds ⋅ 5 Baths ⋅ 944725 MLS
Step into timeless elegance with this stately 9 bedroom 4.5 bath Federal Style home encompassing over 5,646 square feet of living space. Built in 1890, this grand home is steeped in rich history- once owned by George Macy, the famed tea importer. This architectural gem showcases classic period details including four fireplaces, intricate woodwork and moldings, high ceilings, and generously proportioned rooms. The gracious formal living and dining room are ideal for inside entertaining, while a specious deck allows for fabulous outdoor entertaining. This home sits on an expansive 1.4 acre lot and includes a 3-car detached garage, mature landscaping, and a commanding presence that reflects its storied past. With nine spacious bedrooms and four and a half baths, this is a rare opportunity to own a piece of history in an area known for it's prestigious homes and legacy properties.

35 S Penataquit Avenue, Bay Shore
$2,700,000
977463 MLS
Discover an exceptional industrial property in 11 Pine Aire Drive, Bay Shore, New York 11706. This versatile property offers 10,000 SF of industrial space on a generous 0.65-acre lot, all in a prime IND 1 zoning location. With the flexibility to be delivered fully vacant, this property presents a rare owner-user opportunity. Conveniently situated in Bay Shore, NY, the building features three drive-ins, ample parking, and a partially HVAC equipped interior with 12'6 ceiling heights.

11 Pineaire Drive, Bay Shore
$3,350,000
5 Beds ⋅ 5 Baths ⋅ 973534 MLS
To-be-built remarkable colonial on one of the most beautiful and sought-after streets in Bay Shore, set on just shy of 1.5 acres with stunning water views of the Great South Bay from the second level. This exceptional 5-bedroom, 4 full bath, 1 half bath residence will feature thoughtfully designed living space and the rare opportunity for full customization, allowing the buyer to tailor every detail to their taste and lifestyle. Proposed features include 10ft first floor ceilings, a state-of-the-art chef's kitchen connecting to a formal dining room through the butler's pantry, additional breakfast room, family room with gas fireplace, spacious great room with gas fireplace- perfect for everyday living and entertaining. A stunning sunroom filled with abundant natural light creates the perfect place to relax while enjoying the surrounding beauty. The home will also feature a charming second-floor balcony overlooking the bay attached to a large master suite with his and her closets, walk in closets in the additional bedrooms, a laundry room on the second level, and beautiful carport, perfect for bringing in groceries, and a detached two-car garage. A truly unique opportunity to build your dream home in a premier Bay Shore location.

100 Awixa Avenue, Bay Shore
$1,300,000
6 Beds ⋅ 5 Baths ⋅ 970268 MLS
Great South Bay lifestyle, resort style backyard, multigenerational flexibility, and easy access to NYC. This expansive 6 bedroom, 4.5 bath Colonial offers incredible space and versatility. The main residence features 3 bedrooms, 2.5 baths, generous living areas, and an upstairs office, while the legal accessory dwelling unit offers 2 bedrooms, 2 full baths, and a separate entrance, ideal for multigenerational living, extended family, or guests. Step outside to your private backyard retreat with an in ground pool, spacious patio, and bocce court, perfect for entertaining or relaxing at home. With 2 zone gas heating, 300 amp electric service, ample parking, proximity to the Great South Bay, LIRR, and NYC, this home offers the space, flexibility, and lifestyle you’ve been looking for. More space. More possibilities. One incredible Bay Shore lifestyle.

108 Awixa Avenue, Bay Shore
$1,500,000
967346 MLS
Nestled on picturesque Manatuck Lake within the private Oakney Estates homeowners association, This exceptional lakefront residential property offers the potential to be divided into two separate parcel while maintaining a single residential home- a rare and flexible opportunity.

2 Garner Lane, Bay Shore
$1,400,000
951712 MLS
This offering features three structures on one deeded lot in the heart of Bay Shore’s Business District. Seventy Park Ave is a 2,600 sq ft commercial building with a current CO allowing the first floor apartment to be used as a Personal Service business and residence, and the second floor as a separate apartment. The current owner is using both floors as a one family residence with a Personal Service business. The property offers parking for 5 to 7 vehicles and includes many updates throughout including the kitchen, three full bathrooms, and a full roof replacement completed approximately six years ago. Additional building features include natural gas hook up in house for cooking, an oil heating system and exterior cellar access to a full unfinished basement. The property is connected to sewers and public water, has commercial dumpster service for rubbish removal, and contains three electrical meters: two residential panels for the first and second floors and one commercial panel servicing the basement and garage. There is also a 400 sq ft detached two car garage and an additional 1100 sq ft building at 1636 and 1636A Union Blvd, CO’d as a legal two family dwelling with a studio and a one bedroom apartment. These units are separately metered for electric, with the studio operating on electric heat and the one bedroom having its own gas heating system. Both units are currently vacant. The property presents an opportunity to reposition multiple units at once, resolve outstanding violations, and capitalize on strong rental demand for studio, one bedroom, and two bedroom apartments in the area. With flexible layouts, on site parking, and significant upside through renovation and potential expansion, this asset is well suited for investors seeking value add potential and long term income growth.

70 Park Avenue, Bay Shore
$3,499,000
L3383141 MLS
Professional investment property portfolio for sale featuring Suites #8, #12, and #28 in Building 375, along with the Building 381. These properties are fully occupied with triple-net (NNN) leases, offering stable income and minimal landlord responsibilities. The properties also offer ample parking for tenants and visitors. In addition, three other investment properties are available in Bay Shore, Commack, and East Patchogue. Each property may be purchased individually or as part of a bundled portfolio. Comprehensive due diligence materials, including property profiles, lease abstracts, and rent schedules, are provided in the attached documents.

375-381. #8,11,12,26,28. East Main Street, Bay Shore

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.