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$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
$699,000
3 Beds ⋅ 2 Baths ⋅ 1042181 MLS
Welcome to this beautifully maintained high-ranch home in a Bay Shore neighborhood. This spacious property features Three bedrooms, two full bathrooms, two living rooms, extra rooms in basement and two separate entrances. The flexible layout offers excellent potential for a mother-daughter setup with proper permits. Conveniently located near major highways, shopping, schools, and transportation. Move-in ready and a must-s

1127A Bay Shore Avenue Unit #A, Bay Shore
$649,990
3 Beds ⋅ 1 Baths ⋅ 1041496 MLS
Definition of a Turnkey Home: A Home that is in Pristine Condition and is Ready To Move Right in Without Doing Any Updates * Come Fall in Love With This Spectacular Ranch With A Full Finished Basement * Updates Include a Clean White Quartz Kitchen, a Center Island, New Stainless Steel Appliances and Beautiful Tile Backsplash * Anderson Windows * Crown Molding * Chair Rail * Vaulted Ceilings * Central Air Conditioning * Gas Heating System * Vinyl Plank Flooring * An Electric Fireplace * New Electric Panel with 150 Amp Service and an Additional 60 Amp Sub-Panel * New Doors Throughout * A New Bathroom with a Jetted Soaking Tub with a Separate Stall Shower * This Home Also Features an Amazing Back Yard with 2 Gazebos * TimberTech Deck * Pavers * An Above Ground Pool * A Dog Pen * New Driveway * New Roof * Sewers * Basement has Low-Line Septic For a Future Bathroom * Front Yard Sprinklers

133 Missouri Avenue, Bay Shore
$349,000
1041048 MLS
This vacant land sits right in the heart of Cherry Grove on lovely, Holly Walk. Close to all the Grove has to offer and of course, steps to the most beautiful beach on the Atlantic Coast.

185 Holly Walk, Cherry Grove
$875,000
2 Beds ⋅ 1 Baths ⋅ 1041035 MLS
Tucked away on the desirable West Side, this charming two-bedroom home offers privacy, comfort, and the relaxed lifestyle that makes Cherry Grove so special. The home features generous living and dining areas with an easy, open feel, along with two comfortable bedrooms. Outdoors, a private deck creates the perfect setting for entertaining, relaxing in the sun, or enjoying quiet summer evenings, complemented by a private outdoor shower. Ideally located just steps from the ocean, this inviting home offers the perfect combination of privacy and proximity to the beach. A wonderful opportunity to own your own piece of Cherry Grove and make it your personal Fire Island retreat.

200 Surf Walk, Cherry Grove
$995,000
3 Beds ⋅ 2 Baths ⋅ 1040771 MLS
Contemporary beach house featuring an inviting open-concept layout designed for easy, relaxed living. The bright and airy interior flows seamlessly into a modern, well-appointed kitchen, creating a comfortable space for both everyday living and entertaining. The grand primary bedroom is a wonderful private retreat, featuring sliding glass doors that open directly onto its own private deck—an ideal spot for morning coffee, quiet afternoons, or enjoying the ocean air. Ideally located just three houses from the beach, this home offers the perfect combination of style, comfort, and proximity to the ocean. Outside, a lovely garden and serene backyard setting create a peaceful, private atmosphere, perfect for relaxing, outdoor dining, and enjoying long summer days and evenings. A wonderful opportunity to own a stylish and tranquil beach retreat just steps from the ocean.

101 Greene Walk, Cherry Grove
$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
$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
$600,000
3 Beds ⋅ 1 Baths ⋅ 1037368 MLS
This Ranch Style Home Features 3 Bedrooms, Full Bath, Formal Dining Room, Eat In Kitchen & 1 Car Garage. The information provided is estimated to the best of our abilities at this time.

19 Chapman Place, Bay Shore
$875,000
2 Beds ⋅ 1 Baths ⋅ 1036541 MLS
Tucked away on the desirable West Side, this charming two-bedroom home offers privacy, comfort, and the relaxed lifestyle that makes Cherry Grove so special. The home features generous living and dining areas with an easy, open feel, along with two comfortable bedrooms. Outdoors, a private deck creates the perfect setting for entertaining, relaxing in the sun, or enjoying quiet summer evenings, complemented by a private outdoor shower. Ideally located just steps from the ocean, this inviting home offers the perfect combination of privacy and proximity to the beach. A wonderful opportunity to own your own piece of Cherry Grove and make it your personal Fire Island retreat.

200 Surf, Cherry Grove
$975,000
3 Beds ⋅ 2 Baths ⋅ 1036096 MLS
A quintessential Cherry Grove cottage, cozy and unfussy, perfect for a relaxing beach vacation. There are three bedrooms and two bathrooms (the primary bedroom is en suite), Entertaining is easy with the kitchen open to the living area as well as the dining area. And the house features a spacious deck for outside dining, sunbathing, and lounging by the pool. Refresh yourself with an invigorating outdoor shower. Located in a quiet neighborhood, but still convenient to the nightlife and restaurants, the beach is just 4 houses off the beach, as is the trail through the Sunken Forest. The heated pool completes this lovely property.

259 East Walk, Cherry Grove
$699,999
4 Beds ⋅ 2 Baths ⋅ 1035636 MLS
Welcome to this beautifully updated home, perfectly situated on a quiet, tree-lined cul-de-sac in Bay Shore. This move-in-ready property offers 4 spacious bedrooms, 2 full bathrooms, and central air conditioning for year-round comfort. The home features Andersen windows, elegant oak flooring throughout, LED lighting, and a modern kitchen with stainless steel appliances. Step outside to enjoy a large deck overlooking the generous .25-acre property—perfect for entertaining, relaxing, or outdoor gatherings. Conveniently located just 10 minutes from downtown Bay Shore and the Fire Island ferries, you'll enjoy easy access to shopping, dining, entertainment, and the waterfront.

48 Ellen Street, 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
$775,000
2 Beds ⋅ 1 Baths ⋅ 1035396 MLS
Discover the timeless charm of this delightful cottage, tucked away on an oversized, private lot where peace and tranquility surround you. This quiet retreat offers the perfect blend of seclusion and classic Cherry Grove character. Inside, you'll find two comfortable bedrooms, a full bath, and a sleeping loft that provides additional space for guests. An indoor washer and dryer add everyday convenience, while the inviting interior captures the warmth and simplicity of a true beach cottage. Whether you're seeking a serene weekend escape or a place to create unforgettable summer memories, this quaint hideaway is full of character and possibilities. Rarely does a property with this much privacy and charm become available. A true Cherry Grove gem waiting to be yours.

86 Gerard Walk, Cherry Grove
$269,900
1 Beds ⋅ 1 Baths ⋅ 1035193 MLS
This Home is the one you have been waiting for. Main-level living, tranquil setting, back patio with plenty of green space. Uodates Include, a New Heating System, New Central Air, an updated Kitchen and Bath, Vinyl Flooring, and plenty of Closet Space. Easy access to major Hwys, LIRR, Shopping and Beautiful Beaches. Bay Shore offers a lively downtown area for dining and shopping.

66 Pinebrook Place Unit #66, 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
$500,000
5 Beds ⋅ 2 Baths ⋅ 1030527 MLS
This Colonial style home features 5 bedrooms and 2 baths, 1,488 sq ft of living space on a 4,792 sq ft lot. Needs work, priced to sell.

6 Hansen Street, Bay Shore
$500,000
3 Beds ⋅ 1 Baths ⋅ 1025441 MLS
Opportunity awaits with this 3 Bedroom, 1 Bath Colonial full of potential and ready for your vision. Featuring a living room with a fireplace, formal dining room, and a functional layout, this home offers a great foundation to make it your own. Outside, enjoy a fully fenced yard, an oversized driveway, and a detached garage that has been converted into a versatile hangout and storage space. Being sold as is, this is an excellent opportunity for buyers looking to add their own personal touches and build equity.

117 N Clinton Avenue, Bay Shore
$824,900
2 Beds ⋅ 1 Baths ⋅ 1025002 MLS
This beautifully maintained Cherry Grove home offers the perfect combination of comfort and style. Step inside to discover beautiful wood flooring throughout, soaring vaulted ceilings, and an abundance of natural light from the skylight and thermal double-pane windows. The inviting living room features a wood-burning fireplace, creating the perfect atmosphere for cozy evenings in every season. The updated kitchen and bathroom showcase granite countertops, new appliances, and modern finishes designed for effortless living. This adorable cottage includes central air conditioning and heat, and a newly insulated crawl space with heat tracing for added efficiency and peace of mind. Outdoor living is just as impressive, with two spacious decks ideal for entertaining, dining, or relaxing in the sun. Additional features include a hot and cold outdoor shower, privacy fencing, and a large cedar storage shed. Inside, you’ll appreciate the washer and dryer, large closets, and a loft for additional storage, providing plenty of room for all your beach essentials. Whether you’re searching for a weekend retreat, a summer getaway, or a home to enjoy throughout the summer and then some, this exceptional Cherry Grove property is ready to welcome you. Features Include: Beautiful wood floors throughout Central air conditioning and heat for year round comfort Wood-burning fireplace Thermal double-pane windows Newly insulated under-house area with heat tracing Updated kitchen and bathroom Granite countertops New appliances New decking Two large outdoor living spaces Vaulted ceilings Skylights Large outdoor cedar shed Loft storage Large closets Washer and dryer Hot and cold outdoor shower Privacy fencing This home is a rare opportunity to own a thoughtfully updated, move-in-ready property in the heart of Cherry Grove

169 Main Walk, Cherry Grove
$2,500,000
4 Beds ⋅ 5 Baths ⋅ 1017237 MLS
Brand New Oceanfront Home with Pool! This stunning newly constructed residence offers the perfect blend of luxury, comfort, and breathtaking natural beauty. Featuring four spacious bedrooms, including two private primary ensuite retreats, and three-and-a-half beautifully appointed bathrooms, the home is designed for effortless coastal living. The bright and airy open-concept living, dining, and kitchen area is ideal for entertaining, with seamless indoor-outdoor flow and spectacular water views. Step outside to enjoy the fabulous new swimming pool and stylish cabana, creating your own private resort by the sea. Crowning this exceptional property is an expansive roof deck showcasing panoramic vistas of both the Atlantic Ocean and the Great South Bay—an unforgettable setting for sunrise coffee, sunset cocktails, and stargazing. A rare opportunity to own a brand-new oceanfront sanctuary in an incomparable location.

52 Lewis Walk, Cherry Grove
$1,750,000
7 Beds ⋅ 8 Baths ⋅ 1017133 MLS
Wisteria is a one-of-a-kind luxury retreat in Cherry Grove, Fire Island, completely rebuilt in 2020. This exceptional property features seven private en-suite bedrooms, including two poolside suites, a stunning open-concept living area with chef’s kitchen, and resort-style amenities throughout. Enjoy a solar-heated pool, meditation garden, covered outdoor dining pavilion, and a separate studio with full bath. The spectacular rooftop deck offers panoramic views from the Atlantic Ocean to the Great South Bay. A rare opportunity to experience the ultimate in Fire Island luxury and privacy

37 Bayview Walk, Cherry Grove
$350,000
1013890 MLS
Build your dream home on this prime oceanfront corner lot located on the coveted East End of Cherry Grove. Perched behind a high protective dune, this exceptional property offers a rare combination of privacy, elevation, and direct access to one of the most beautiful beaches on the East Coast. Enjoy breathtaking ocean views, the soothing sound of the surf, and endless possibilities for creating your ideal coastal retreat. Just steps from the sand, this unique parcel presents a remarkable opportunity to own a piece of Fire Island's spectacular shoreline. Oceanfront lots of this caliber are seldom available.

54A Lewis Walk, Cherry Grove
$1,350,000
4 Beds ⋅ 2 Baths ⋅ 1015727 MLS
This is truly a one-of-a-kind opportunity! An extraordinary, expansive ocean front property in Cherry Grove, featuring a rare double lot with stunning ocean frontage. It has never been offered before, and the possibilities here are truly endless. What sets this property apart is the land itself and the boundless potential it holds. A great location on the East end of the Grove, perched atop a high dune with breathtaking ocean views. This oceanfront home offers a rare opportunity to own a piece of timeless charm. Lovingly built in the early 1950s and maintained by the same owners for generations, this unique property is simply a must-see. Four spacious bedrooms, including a primary bedroom on the main floor and three additional bedrooms on the lower level. 1.5 bathrooms plus the added convenience of an outdoor shower perfect for rinsing off after a day at the beach. The main Floor is designed with the open-concept: living, dining, and kitchen areas creating a seamless flow for entertaining or enjoying quiet moments.

54 Lewis Walk, Cherry Grove
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 1014328 MLS
Experience coastal living at its finest in this exceptional 3-bedroom, 3-bathroom home featuring stunning bay views from multiple levels and some of the most breathtaking panoramas in Cherry Grove. Relax on the spacious rear deck as you watch ferries glide across the bay and enjoy the ever-changing waterfront scenery. The primary suite opens to a charming Juliette balcony, offering a private retreat with picturesque bay views. For truly unforgettable sunsets and sweeping water vistas, the rooftop deck provides one of the area's most spectacular vantage points. The first floor features a bright, open-concept layout designed for effortless entertaining, with a spacious living room, dining area, and well-appointed kitchen, all accented by beautiful hardwood floors. This level also includes a comfortable guest bedroom, a full bath, and a convenient laundry/utility room. On the second floor, the primary suite offers a private en suite bath and direct access to the Juliette balcony overlooking the bay as well as a 3rd bedroom. At the top of the spiral staircase is a third full bath, along with a versatile loft-style space featuring a desk area and room for a pull-out sofa, creating additional sleeping accommodations for guests or work space. With its thoughtfully designed layout, multiple outdoor living spaces, and spectacular bay views from nearly every level, this remarkable home offers the perfect blend of comfort, style, and waterfront charm.

118 Bayview Walk, Cherry Grove
$525,000
3 Beds ⋅ 1 Baths ⋅ 1007567 MLS
Ranch, updated 3 bedrooms, 1 bath, living room, dining room, kitchen with good countertop. Updates include new floor, lighting, roof, new driveway.Natural gas heating and detached garage and nice yard. Conveniently located near shopping, dining , parks, and transportation. Move-in-ready.

146 Penataquit Avenue, Bay Shore
$795,000
2 Beds ⋅ 2 Baths ⋅ 996848 MLS
Charming original cottage situated directly on the Great South Bay, featuring two bedrooms and two full bathrooms, plus an outdoor shower and ample space for a large pool. The open-concept living and dining area boasts vaulted ceilings and a cozy fireplace, creating a bright and inviting atmosphere. The primary bedroom features sliding glass doors that open directly onto the bayside deck, offering stunning water views and easy outdoor access. Additional highlights include an updated kitchen, an indoor washer and dryer, and a spacious corner lot. This unique waterfront property combines classic cottage charm with modern conveniences, making it the perfect bayside retreat.

71 Bayview Walk, Cherry Grove
$859,000
6 Beds ⋅ 3 Baths ⋅ 1001272 MLS
Spacious multi-generational high ranch offering excellent flexibility and potential. This home features a rear two-level addition Many updates have been completed within the last two years, including the roof, siding, driveway, walkways, and fencing. The primary kitchen, updated, offers a modern open layout enhanced by a large skylight that brings in abundant natural light. The first floor has a private entrance and includes a bedroom, living room, dining area, full bathroom, and additional room, making it ideal for extended living arrangements. The property can easily be converted back to a 6-bedroom single-family residence while keeping the existing two-car garage. Move-in ready with generator hookup and in-ground sprinklers. Interior features include hardwood floors and hot water heating. STAR eligible. Buyer may qualify for property tax savings, subject to eligibility. Seller concessions may be considered.”

58 Oakridge Drive, 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
$219,000
1 Beds ⋅ 1 Baths ⋅ 975726 MLS
Vacant 1 Bedroom first floor with separate office

5A Hemlock Drive, 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.