Homes for Sale in Oyster Bay, NY with 5-Bedrooms & a Private Pool

/44
$5,699,000
- 5 Beds
- 5.5 Baths
- 6,157 Sq Ft
8 Serenite Ln, Syosset, NY 11791

Welcome to this European-inspired estate in the heart of Muttontown, where old-world craftsmanship meets modern luxury. Set on over two private acres, this picturesque property is introduced by a long, tree-lined driveway that leads to a stunning brick carriage house—complete with its own 2-bedroom apartment, ideal for multigenerational living or passive rental income. The main residence offers 5

Joe Scavo Douglas Elliman Real Estate

8 Serenite Ln, Syosset, NY 11791
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/50
$2,798,000
- 5 Beds
- 5.5 Baths
- 4,300 Sq Ft
45 Carriage Ct, Syosset, NY 11791

Situated On A Cul de Sac Location,Step Into Contemporary Luxury With This Completely Updated Home,A True Entertainer's Dream,Boasting An Open Concept Design That Seamlessly Blends Sleek Modern Finishes With Warm,Inviting Spaces.Sun Drenched Living Area Flows Effortlessly Into Den With Fireplace And State Of The Art Kitchen,Miele Appliances,Spacious Island Perfect For Gatherings. Retreat To The

Batul Morbi Compass Greater NY LLC

45 Carriage Ct, Syosset, NY 11791
/48
$3,298,000
- 5 Beds
- 5.5 Baths
- 5,181 Sq Ft
15 Pironi Ct, Woodbury, NY 11797

Architecturally distinguished and extensively updated, this stately custom Colonial set on nearly one acre of private cul-de-sac property in the heart of Woodbury. Offering 5,181 square feet of refined living space, this residence reflects timeless design, superior craftsmanship, and meticulous attention to detail. The home presents with a fresh, like-new aesthetic, highlighted by a fully

Steven Shaughnessy Charles Rutenberg Realty Inc

15 Pironi Ct, Woodbury, NY 11797
/21
$2,850,000
- 5 Beds
- 3.5 Baths
- 4,421 Sq Ft
10 Dorchester Dr, Glen Head, NY 11545

Set on a distinguished two-acre property in the heart of Muttontown, New York, and nestled within a beautiful, sprawling neighborhood, this expansive ranch residence exudes privacy, scale, and timeless sophistication. Tucked well back from the road and surrounded by meticulously maintained landscaping, the home welcomes guests through a double-door entrance to an oversized foyer that immediately

Jason Friedman Daniel Gale Sothebys Intl Rlty

10 Dorchester Dr, Glen Head, NY 11545
/27
$4,699,000
- 6 Beds
- 11 Baths
- 6,662 Sq Ft
8 Brookville Ln S, Glen Head, NY 11545

Located in one of Brookville’s most sought-after locations, this exceptional brick Colonial offers almost 7,000 square feet of timeless architecture, modern updates, and effortless elegance.Light-filled interiors and beautifully scaled rooms create a seamless flow ideal for both grand entertaining and comfortable everyday living. Classic design details blend beautifully with a fresh,

Karen Sharf Daniel Gale Sothebys Intl Rlty

8 Brookville Ln S, Glen Head, NY 11545
/40
$1,799,000
- 6 Beds
- 2.5 Baths
- 3,391 Sq Ft
5 Pine St, Plainview, NY 11803

Where luxury meets legacy! This isn't just a house; it’s the lifestyle upgrade you’ve been waiting for.The Grand Entrance: Step into a masterpiece of design where soaring high ceilings and a shimmering statement chandelier set the stage for a home that breathes elegance and scale.A Chef’s Sanctuary: The heart of the home features a massive center island (seating for four!), premium

Michael Pascullo Douglas Elliman Real Estate

5 Pine St, Plainview, NY 11803
/33
$2,299,000
- 5 Beds
- 6.5 Baths
- 4,685 Sq Ft
530 S Centre Island Rd, Oyster Bay, NY 11771

Welcome to 530 Centre Island Rd, Centre Island — One of the most exclusive top private islands for your home. This massive center-hall brick Colonial sits on a 3-acre lot. Home improvements were partially completed in 2024. With 4,685 sq. ft. of interior space, it provides 5 bedrooms (all 5 BR are en-suites), 6.5 baths, a formal dining room, family room, living room, office, sunroom, two-car

Chuan Wang Chen E Realty International Corp

530 S Centre Island Rd, Oyster Bay, NY 11771
/27
$3,950,000
- 5 Beds
- 4.5 Baths
- 5,000 Sq Ft
42 Clock Tower Ln, Old Westbury, NY 11568

OLD WESTBURY | HISTORIC GRANDEUR. TIMELESS PRESTIGE. REFINED MODERN LIVING. 42 Clocktower Lane stands as a timeless testament to Gilded Age architecture and estate living on Long Island. Designed by the renowned architect Stanford White — a key figure behind many of America’s most celebrated turn-of-the-century landmarks — this distinguished residence was originally part of the expansive Morgan

Maria Babaev Douglas Elliman Real Estate

42 Clock Tower Ln, Old Westbury, NY 11568
/29
$2,199,999
- 6 Beds
- 3.5 Baths
- 5,103 Sq Ft
9 Chicken Valley Rd, Glen Head, NY 11545

Sprawling Brick Expanded Ranch in Prestigious Old Brookville! Welcome to this impressive custom-expanded ranch, rebuilt in 2001 and nestled on 2.2 flat acres in the heart of Old Brookville. Offering over 5,100 sq ft of living space, this 6-bedroom, 3.5-bath home combines generous scale with a versatile open floor plan—perfect for both everyday living and entertaining. Highlights include a large

Katherine Koniecko Signature Premier Properties

9 Chicken Valley Rd, Glen Head, NY 11545
/42
$3,850,000
- 7 Beds
- 6.5 Baths
- 8,242 Sq Ft
11 Danton Ln N, Locust Valley, NY 11560

In the exclusive private enclave Lands End in the Village of Lattingtown, this exceptional newer estate is set on four beautifully landscaped acres and built to the highest standards of craftsmanship and design. The stately all brick colonial is introduced by a long paver driveway leading to an elegant courtyard and dramatic portico entry - creating a striking and memorable arrival. Inside,

Michael Stanco Compass Greater NY LLC

11 Danton Ln N, Locust Valley, NY 11560
/50
$9,807,230
- 6 Beds
- 12 Baths
- 16,500 Sq Ft
660 Chicken Valley Rd, Locust Valley, NY 11560

Nestled on 5.33 acres of pristine landscape, this stunning 2003 estate embodies sophisticated living at its finest. With approximately 16,500 square feet of meticulously designed interiors, this home offers a harmonious blend of grandeur and functionality. Featuring 6 spacious bedrooms, 9 full bathrooms, and 3 half bathrooms, this residence perfectly balances opulence with functionality. The

Huailing Deng Daniel Gale Sothebys Intl Rlty

660 Chicken Valley Rd, Locust Valley, NY 11560
/42
$1,225,000
- 7 Beds
- 3.5 Baths
- 3,400 Sq Ft
166 Daniel Rd N, Massapequa, NY 11758

Rare opportunity to own a truly one-of-a-kind colonial in the highly reputable Plainedge School District. Originally a ranch, this home was thoughtfully expanded into a beautiful colonial, with the entire upper level newly constructed within the last few years—creating a spacious and flexible layout rarely found in the area. Offering 7 bedrooms and 3.5 bathrooms, including 3 bedrooms on the main

Jason Krawitz Jason W Krawitz

166 Daniel Rd N, Massapequa, NY 11758
/37
$8,750,000
- 6 Beds
- 9 Baths
- 8,000 Sq Ft
30 Wood Acres Rd, Glen Head, NY 11545

Introducing a newly constructed custom Brookville Colonial crowned with a stunning slate roof, offering an extraordinary blend of classic architecture and elevated designer finishes. Privately set behind an electric gate on over 2.53 fully landscaped acres, this exceptional estate, constructed in 2020, has been thoughtfully designed for both grand-scale entertaining and refined everyday living. A

Jason Friedman Daniel Gale Sothebys Intl Rlty

30 Wood Acres Rd, Glen Head, NY 11545
/34
$5,495,000
- 6 Beds
- 6.5 Baths
- 6,885 Sq Ft
63 Fruitledge Rd, Glen Head, NY 11545

Set on two private acres in the heart of Brookville and located within the Locust Valley School District, 63 Fruitledge Road offers refined luxury living on Long Island’s prestigious Gold Coast. This newly completed 6,880 Sq ft residence features a striking modern Colonial exterior with expansive windows and 10-foot ceilings throughout, creating an airy, light-filled atmosphere and large-scale

Melanie Cogan Compass Greater NY LLC

63 Fruitledge Rd, Glen Head, NY 11545
/41
$10,750,000
- 9 Beds
- 12 Baths
- 13,058 Sq Ft
393 Mill River Rd, Oyster Bay, NY 11771

Tucked behind a private gated drive and set across over eight pristine acres, this iconic 1916 manor estate has been comprehensively restored and strategically enhanced to meet the expectations of today’s most discerning buyer. Historic architecture remains intact, while modern systems, technology, and amenities have been elevated to a truly exceptional level. Grand formal living and dining rooms

Shawn Elliott Nest Seekers LLC

393 Mill River Rd, Oyster Bay, NY 11771
/32
$3,888,880
- 6 Beds
- 5.5 Baths
- 5,353 Sq Ft
47 Valley Rd, Old Westbury, NY 11568

JERICHO SCHOOL AND OLD WESTBURY. This Gorgeous Colonial Is Approached By A Long Circular Drive Offering Beautiful Landscaping.The House Features An Open And Airy Floor Plan Exhibiting Classic Moldings, Gleaming Hardwood Floors, Soaring Ceilings, Central A/C And Spacious Rooms. Total Six Bedrooms With Five Full Bath And One Powder Room, A Gorgeous First Floor Master Suite, Formal Dinning Room,

Yanting Yang Welhome Realty Inc

47 Valley Rd, Old Westbury, NY 11568
/26
$8,500,000
- 6 Beds
- 7.5 Baths
- 7,047 Sq Ft
200 Centre Island Rd, Oyster Bay, NY 11771

Overlooking picturesque Oyster Bay Harbor, this stately waterfront Manor home is located on 1.71 acres and boasts 245 feet of water frontage. Featuring 6 large bedrooms with walk-in closets and 7.5 baths with high-end fixtures and fittings, this magnificent property has an idyllic master retreat on the main floor with incredible views across the Harbor, 2 spacious walk-in closets with center

John Messina Daniel Gale Sothebys Intl Rlty

200 Centre Island Rd, Oyster Bay, NY 11771
/25
$5,995,000
- 9 Beds
- 9 Baths
- 11,382 Sq Ft
15 High Ridge Ln, Oyster Bay, NY 11771

Experience timeless elegance and grand-scale living in this extraordinary residence offering over 13,000 square feet of luxurious living space, perfectly set on more than 5 acres of manicured grounds. Enter through the impressive dual staircase foyer that sets the tone for this stately home, featuring 9 bedrooms and 9 bathrooms designed for comfort and sophistication. The main level boasts

John Kim NEXTHOME PLATINUM PROPERTIES

15 High Ridge Ln, Oyster Bay, NY 11771
/50
$5,495,000
- 6 Beds
- 9 Baths
- 9,534 Sq Ft
6 La Colline Dr, Mill Neck, NY 11765

An extraordinary life begins here - A true luxury masterpiece, this extraordinary estate offers over 12,000 square feet of impeccably finished living space, gracefully positioned on five acres of private, manicured grounds. Designed for those who demand excellence, the residence blends timeless architectural elegance with modern amenities of the highest caliber, creating a lifestyle of

Michael Pesce BERKSHIRE HATHAWAY

6 La Colline Dr, Mill Neck, NY 11765
/25
$2,480,000
- 5 Beds
- 3.5 Baths
- 3,959 Sq Ft
4 Norgate Rd, Glen Head, NY 11545

Exquisite 5-bedroom residence on a private cul-de-sac set within the highly-regarded Jericho School District. This home features approximately 3,959 sq ft of living space on a flat, pristine 2-acre parcel. Built in 1952 and lovingly maintained, the property offers timeless appeal with modern comforts — two fireplaces, central air-conditioning, and a fully finished lower level. Outdoors, enjoy a

Mark Jia United Real Estate Fortune

4 Norgate Rd, Glen Head, NY 11545
/8
$4,988,000
- 6 Beds
- 6.5 Baths
- 7,049 Sq Ft
7 the Rise, Woodbury, NY 11797

Modern Luxury to be built in The Gates of Woodbury. Welcome to 7 The Rise, a breathtaking custom-designed residence located in one of Woodbury’s most prestigious and sought-after neighborhoods. Set on a full one-acre property, this custom built masterpiece offers exceptional craftsmanship, refined architectural detail, and a lifestyle of elevated comfort. Inside, you’ll find soaring ceilings,

Stephen Gaon Real Broker NY LLC

7 the Rise, Woodbury, NY 11797
/13
$7,900,000
- 5 Beds
- 7.5 Baths
- 8,600 Sq Ft
Lot A High Point Ct, Brookville, NY 11545

High Point Court / Parcel A – BrookvilleA rare opportunity to create a custom luxury estate in one of the North Shore’s most prestigious settings. Plans designed by Steven E.Homburger AIA withGallagher Homburger Group ,Architects, PLLC. He is known for many Gold Coast Mansions designs. This private cul-de-sac parcel is offered with full architectural estate plans, allowing the buyer to

Luis Laino Gold Coast Real Estate Group

Lot A High Point Ct, Brookville, NY 11545
/49
$1,750,000
- 5 Beds
- 3.5 Baths
- 2,603 Sq Ft
28 Elm St, Woodbury, NY 11797

Elegant Move-In-Ready Ranch with Pool, Office, and Full Finished Basement in the Syosset School District.Welcome to 28 Elm Street, a beautifully renovated five-bedroom, three-bath ranch offering the perfect combination of modern design, functionality, and timeless comfort. Located on a quiet, tree-lined street in one of Woodbury’s most desirable neighborhoods, this home is ideal for everyday

Sima Levy Nest Seekers LLC

28 Elm St, Woodbury, NY 11797
/28
$1,899,000 Open Sat 12PM - 3PM
- 5 Beds
- 5 Baths
- 3,700 Sq Ft
65 Mellow Ln, Jericho, NY 11753

This stunning expanded split-level home features 5 bedrooms and 5 full baths, thoughtfully designed to blend elegance, comfort, and exceptional functionality across five distinct levels. Follow the beautiful open staircase to the upper living area ,a custom movie theater and a private guest suite with a full bath—perfect for entertainment and overnight stays. This upper living area where you’ll

Hong Lu Passerina LLC

65 Mellow Ln, Jericho, NY 11753
/29
$5,995,000
- 6 Beds
- 6.5 Baths
- 7,488 Sq Ft
178 Brookville Rd, Glen Head, NY 11545

Timeless Elegance in the Heart of Muttontown. Set along a long, gated private drive in coveted Muttontown, this distinguished six-bedroom Brick Colonial offers an extraordinary blend of classic architecture and modern sophistication. Every detail of this grand residence reflects masterful craftsmanship—custom millwork, rich hardwood floors, designer finishes and five fireplaces create an

Elyse Gropper Daniel Gale Sothebys Intl Rlty

178 Brookville Rd, Glen Head, NY 11545
/27
$2,750,000
- 5 Beds
- 4.5 Baths
- 3,739 Sq Ft
6 Clearmeadow Ct, Woodbury, NY 11797

Welcome to 6 Clearmeadow Ct, located in Hunters Run a premier 24-hour gated community within the highly sought-after Woodbury enclave and the Syosset School District. This residence, set on a beautifully landscaped .65-acre lot, seamlessly blends timeless charm with modern sophistication.Originally built in 1987 and updated in 2025, the home offers 5 bedrooms and 4.5 bathrooms. A grand foyer

Lanna Weisfeld W Brothers Brokerage LLC

6 Clearmeadow Ct, Woodbury, NY 11797
/44
$3,850,000 Open Sat 12PM - 2PM
- 6 Beds
- 4.5 Baths
- 6,100 Sq Ft
735 Remsens Ln, Oyster Bay, NY 11771

Welcome to Orchard Fields set on over 2 acres of beautifully flat and private grounds, this stunning 6-bedroom, 5-bathroom Colonial blends timeless elegance with modern comfort in one of Upper Brookville’s most prestigious enclaves. Completely and tastefully renovated, this home offers an effortless indoor-outdoor lifestyle perfect for both everyday living and entertaining.The thoughtfully

Nicholas Conti Compass Greater NY LLC

735 Remsens Ln, Oyster Bay, NY 11771
/17
$2,998,000
- 5 Beds
- 4.5 Baths
- 5,500 Sq Ft
96 Calvin Ave, Syosset, NY 11791

A rare opportunity in the heart of North Syosset: a brand-new LUXURY residence TO BE BUILT on a flat half-acre property with IN-GROUND POOL. MODEL HOME AVAILABLE FOR VIEWING. This center hall colonial will offer approximately 5000 square feet of living space, featuring 5 bedrooms, 4.5 bathrooms, and an expansive open layout ideal for entertaining and everyday living. Exterior metal roof, Ceilings

Patricia Pascullo Salegna Douglas Elliman Real Estate

96 Calvin Ave, Syosset, NY 11791
/43
$12,800,000
- 10 Beds
- 15 Baths
- 20,000 Sq Ft
53 Simonson Rd, Glen Head, NY 11545

Situated behind two private gates, in one of Long Island’s most prestigious enclaves, this newly constructed 10 bedroom, 15 bathroom modern estate is a masterclass in elevated design and luxurious living. Set on an expansive, meticulously landscaped property, the residence pairs timeless architectural grandeur with sleek, contemporary finishes to create a rare and refined sanctuary. A striking

Jason Friedman Daniel Gale Sothebys Intl Rlty

53 Simonson Rd, Glen Head, NY 11545
/36
$1,895,000
- 5 Beds
- 2.5 Baths
- 3,298 Sq Ft
43 Oak Point Dr N, Bayville, NY 11709

Direct waterfront property high above sea level in the Village of Bayville within the highly sought after of Oak Neck Point private community. Sweeping panoramic views over the Long Island Sound, this property features steps down to a blue stone patio, additional sun deck and a private beach. Sea wall in great condition. Water views upon immediately entering the home and from the backyard,

Michael Stanco Compass Greater NY LLC

43 Oak Point Dr N, Bayville, NY 11709
/46
$3,788,000
- 6 Beds
- 9 Baths
- 7,887 Sq Ft
12 Ridge Ct, Glen Head, NY 11545

Welcome to 12 Ridge Ct, located in the heart of Old Brookville in the Brookville Meadows. This is your window of opportunity to live in the Gold Coast on 3.4 acres of flat land. From the moment you turn on to the tree-lined street (White Gate Dr.) entering Brookville Meadows, you will feel the caliber of luxury you are about to enter. This home boasts over 7,800 sq feet, the open layout will give

Richard Brazzano BERKSHIRE HATHAWAY

12 Ridge Ct, Glen Head, NY 11545
/41
$6,995,000
- 5 Beds
- 6.5 Baths
- 9,000 Sq Ft
26 Tennis Court Rd, Oyster Bay, NY 11771

Experience the ultimate in waterfront living with this extraordinary 9,000+ sq. ft. estate set on two sweeping acres with 200 feet of private shoreline in Oyster Bay. Designed for both grand entertaining and everyday comfort, the residence offers 5 bedrooms, 6.5 baths, and 4 fireplaces, all supported by modern essentials including a full-house generator and security system.Step inside the

Liza Bendett Compass Greater NY LLC

26 Tennis Court Rd, Oyster Bay, NY 11771
/49
$3,429,000
- 5 Beds
- 4.5 Baths
- 6,751 Sq Ft
12 Parish Dr, Locust Valley, NY 11560

Hydrangea House-A luxurious retreat offers the perfect blend of elegance and luxury living. With exclusive access to Lattingtown Harbor Beach and Clubhouse, enjoy all the amenities of boating, community gatherings, fishing, kayaking, swimming and a floating dock, just minutes from your front door. Spanning 6,751 sq. ft., this 10-room grand home is designed for both entertaining and peaceful

Regina Rogers Douglas Elliman Real Estate

12 Parish Dr, Locust Valley, NY 11560
/47
$5,698,000
- 6 Beds
- 9 Baths
- 6,921 Sq Ft
5 Farmwoods Ln, Glen Head, NY 11545

This gorgeous Brick Colonial, located in Upper Brookville, is a beautiful and elegant estate that sits on 2.53 acres. Built in 2007, this residence offers an impressive 6 bedrooms and 7 bathrooms within its expansive 6,921 square feet of living space. Step inside to find a home designed for both grand entertaining and comfortable living. The first floor features a formal living room, a formal

Batul Morbi Compass Greater NY LLC

5 Farmwoods Ln, Glen Head, NY 11545
/22
$3,500,000
- 6 Beds
- 9 Baths
- 7,500 Sq Ft
5 Carol Ln, Glen Head, NY 11545

Elegance redefined in this stunning gem that blends an eclectic mix of mid-century modern design with a touch of contemporary sophistication, nestled on two lush, gated acres in Upper Brookville. From the moment you enter, the home captivates your imagination with its soaring 30-foot ceilings and dramatic windows and wood architectural elements. Clean lines, warm textures, and artful finishes

Ken Deutsch Deutsch Realty Inc

5 Carol Ln, Glen Head, NY 11545
/50
$7,999,999
- 6 Beds
- 8 Baths
- 8,600 Sq Ft
8 Dogwood Hill, Glen Head, NY 11545

Brookville | An immaculate modern colonial has made its debut in Brookville. Sitting on 2.57 acres and totaling over 8,600 sq.ft. of living space, welcome to 8 Dogwood Hill - a newly completed luxury residence located on a lengthy, picturesque street just off of Cedar Swamp Road. Beyond the stone pillar entrance at the end of the driveway are two courtyards with belgium block accents that lead to

Joe Scavo Douglas Elliman Real Estate

8 Dogwood Hill, Glen Head, NY 11545
/2
$4,200,000
- 5 Beds
- 4.5 Baths
- 5,659 Sq Ft
45 Pelican Ct, Syosset, NY 11791

This Extraordinary New Construction Estate Offering Over 5,600 Sq Ft of Refined Living Space Poised on a coveted .46 Acre parcel. This 'to-be-built' architectural gem promises exceptional craftsmanship and timeless sophistication.The first floor welcomes you with a dramatic grand entryway foyer leading to a gourmet chef’s eat-in kitchen, complete with premium appliances, custom cabinetry, and

Nancy Davila Campo Four Seasons Realty Team

45 Pelican Ct, Syosset, NY 11791
/40
$6,500,000
- 5 Beds
- 7 Baths
- 7,479 Sq Ft
4 Clock Tower Ln, Old Westbury, NY 11568

Welcome to 4 Clock Tower Lane – A Private Estate in Prestigious Old WestburyNestled on 7.96 beautifully landscaped acres, this extraordinary estate offers the ultimate in luxury, privacy, and resort-style living. The elegant main residence features 5 spacious bedrooms and 5 full bathrooms, 2 powder rooms, designed with timeless sophistication and modern functionality. The primary bedroom

Andrea Levine Keller Williams Rty Gold Coast

4 Clock Tower Ln, Old Westbury, NY 11568
/46
$3,999,998 Open Sun 1:30PM - 3PM
- 5 Beds
- 5.5 Baths
- 5,200 Sq Ft
32 Pine Rd, Syosset, NY 11791

One Acre New Build of 5200 plus square feet in Private & Serene Country Setting with Big Sky Views in the Heart of North Syosset! Stunning Masterpiece of Modern Luxury Living by Prominent North Shore Builder! Beautiful Hampton Style Center Hall Colonial in a lush tree lined neighborhood. You are greeted with a formal 2 story entry that showcases elegance and sophistication on one acre of tranquil

Valerie Rosenblatt Daniel Gale Sothebys Intl Rlty

32 Pine Rd, Syosset, NY 11791
/37
$7,300,000
- 9 Beds
- 12 Baths
- 17,587 Sq Ft
60 Piping Rock Rd, Glen Head, NY 11545

Welcome to GRAY HORSE FARM - Just Updated & Renovated for 2025 luxury living! Recently transformed with a gut-renovated Top of the line chef's kitchen with new cabinets, countertops, backsplash, floor, and high-end appliances. There are six new designer bathrooms, all-new recessed lighting throughout, upgraded 800-AMP electric and utility systems. This grand estate seamlessly blends timeless

Aileen Murstein Compass Greater NY LLC

60 Piping Rock Rd, Glen Head, NY 11545

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