Homes for Sale in Long Island, NY with 5-Bedrooms & a Private Pool

/21
$2,850,000 Open Sun 1PM - 3PM
- 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
/32
$14,950,000
- 20 Beds
- 30 Baths
- 10,000 Sq Ft
23 Old Westbury Rd, Old Westbury, NY 11568

Welcome to 23 Old Westbury Road, an extraordinary private compound set on approximately 16 acres of fully landscaped grounds in one of Long Island’s most prestigious enclaves. At its heart stands a ~10,000 sq. ft. Mediterranean-style brick mansion of commanding presence, complemented by seven additional legal residences, 14 garages, two large barns, and a U-shaped horse stable. The estate offers

Zach Elliott Nest Seekers LLC

23 Old Westbury Rd, Old Westbury, NY 11568
/4
$5,595,000
- 7 Beds
- 7.5 Baths
- 6,600 Sq Ft
259 Majors Path, Southampton, NY 11968

Presenting an exceptional new Hamptons estate, currently under construction and slated for completion at the end of 2025. This bespoke two-story residence spans approximately 6,651 sq. ft. of masterfully crafted living space, blending timeless architectural elegance with modern luxury for the ultimate year-round retreat or seasonal escape.A dramatic double-height foyer introduces an airy,

Geoff Gifkins Nest Seekers International LLC

259 Majors Path, Southampton, NY 11968
/28
$1,195,000
- 5 Beds
- 4 Baths
- 3,463 Sq Ft
52 Matinecock Ave, East Islip, NY 11730

Welcome to this exceptional 5-bedroom, 4-bath residence in the heart of East Islip, offering 3,463 square feet of beautifully designed living space on a generous 100 x 200 property. This home blends elegance and comfort with gleaming wood floors throughout, a formal living room with a cozy fireplace, and a spacious formal dining room perfect for entertaining, and office. The chef’s kitchen and

Tammy Ramsay Eric G Ramsay Jr Assoc LLC

52 Matinecock Ave, East Islip, NY 11730
/42
$2,825,000
- 6 Beds
- 9 Baths
- 5,700 Sq Ft
66 Peters Ln, Westhampton Beach, NY 11978

Discover refined Hamptons living in this newly completed residence set on a private, thoughtfully positioned lot in the hamlet of Quiogue. Designed with a rear-yard focus to maximize privacy and outdoor enjoyment, the home offers an elegant balance of modern architecture and timeless finishes throughout. An open-concept main level features a chef’s kitchen with premium appliances, spacious dining

Amy Ball Amy J Ball

66 Peters Ln, Westhampton Beach, NY 11978
/45
$675,000
- 5 Beds
- 2 Baths
- 2,556 Sq Ft
43 Madeline Rd, Ridge, NY 11961

Welcome to 43 Madeleine Road in Ridge, a wonderful place to grow, gather, and create lasting memories. Set on a private 1-acre lot and bordering an additional 2-acre town-owned parcel, this home offers exceptional space, privacy, and room for everyone. This spacious High Ranch features a layout ideal for a large or extended family.The upper level offers a beautifully updated kitchen with a

Laura Kraker Exit Realty Achieve

43 Madeline Rd, Ridge, NY 11961
/28
$20,000,000
- 6 Beds
- 8 Baths
- 5,457 Sq Ft
19 and 33 Bridgefield Rd, Bridgehampton, NY 11932

Estate with Tennis & Buildable Lot, South of Highway, Near OceanLess than one mile from the ocean, in one of Bridgehampton South's most treasured estate settings, this offering unites two already subdivided parcels totaling two and one half acres. It is a rare opportunity to secure a presence of meaningful scale in the Hamptons, where the serenity of the present and the promise of the future

Angela Boyer Sothebys Int'l Realty Hamptons

19 and 33 Bridgefield Rd, Bridgehampton, NY 11932
/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
$829,999
- 5 Beds
- 3 Baths
- 2,435 Sq Ft
214 Pipe Stave Hollow Rd, Mount Sinai, NY 11766

Proudly offered is this builder’s custom-built residence, owned by the original owner and constructed with superior craftsmanship, including 12" on-center floor board construction. Meticulously cared for over the years, this home is ideally situated on a quiet street south of 25A. Featuring 5 bedrooms and 4 full baths, the home offers generous living space—ideal for a large or extended family, or

Linda Stowell Howard Hanna Coach

214 Pipe Stave Hollow Rd, Mount Sinai, NY 11766
/12
$2,350,000
- 5 Beds
- 3 Baths
- 4,585 Sq Ft
6 Twilight Ct, Melville, NY 11747

Welcome to this beautifully updated ranch-style home in the heart of Melville, offering 5 bedrooms, 3 full baths, and a dedicated office — perfect for today’s lifestyle. With over 4,500 sq ft of living space, this home impresses with its spacious, open kitchen layout, ideal for both everyday living and entertaining. The bright and inviting large den is perfect for gatherings, while the new

Derek Greene Greene Realty Group

6 Twilight Ct, Melville, NY 11747
/50
$5,199,988
- 5 Beds
- 5.5 Baths
- 5,875 Sq Ft
26 Saint Andrews Ct, Old Westbury, NY 11568

This all-brick New Construction home represents the height of modern luxury, perfectly situated on two acres within a quiet cul-de-sac in the Village of Old Westbury. Architectural excellence is defined by an open-concept floor plan with soaring 10-foot ceilings on the first and second floors, complemented by a massive 11-foot basement with a dedicated outside entrance. Large Anderson 400 series

Monique Serena Keller Williams Points North

26 Saint Andrews Ct, Old Westbury, NY 11568
/33
$4,495,000
- 5 Beds
- 5.5 Baths
- 5,260 Sq Ft
44 Ocean View Pkwy, Southampton, NY 11968

Just imagine pulling into your gated, stunning, traditional home in Southampton. Spread across 2.2 acres on one of the most prestigious streets in the Hamptons, the feeling you get when you arrive at the front door can be described in one word: home. This cedar-shingled traditional boasts a gated entry, private driveway, and a thoughtful layout perfect for both relaxation and entertaining.

Vincent Horcasitas Saunders & Associates

44 Ocean View Pkwy, Southampton, NY 11968
/34
$17,495,000
- 6 Beds
- 5.5 Baths
- 4,800 Sq Ft
40 Deforest Rd, Montauk, NY 11954

Never before seen, On The Break is a rare compilation of new construction luxury homes set amidst the natural landscape and vibrant cultural scene of Montauk. Encompassing two separate oceanfront lots, the enclave presents an unmatched opportunity to own in the highly sought after Ditch Plains area. One of the most iconic surf destinations on the East Coast, the break within Ditch Plains boasts

Hedgerow Exclusive Team Hedgerow Exclusive Properties

40 Deforest Rd, Montauk, NY 11954
/37
$6,995,000
- 5 Beds
- 8.5 Baths
- 6,000 Sq Ft
16 Wills Point Rd, Montauk, NY 11954

Welcome to 16 Wills Point Road in Culloden Point-where spectacular sunsets and Fort Pond Bay views become your daily backdrop. Set on 1.4 acres down a private cul-de-sac, this over 6,000 sq. ft. custom-built home features 5 bedrooms with soaring 10-foot+ ceilings and water views from nearly every room. Multiple private decks offer front-row seating to legendary Montauk sunsets. The residence is

Hedgerow Exclusive Team Hedgerow Exclusive Properties

16 Wills Point Rd, Montauk, NY 11954
/36
$28,000,000
- 7 Beds
- 13 Baths
- 25,000 Sq Ft
6 Spring Hill Ln, Old Westbury, NY 11568

This amenity-rich estate, custom built by John Kean, is situated on 7 acres of perfectly manicured grounds within the Gold Coast's most sought after gated community, Spring Hill. The handsomely appointed natural stone mansion boasts 25,000 square feet of living space, including 7 bedrooms, 13 bathrooms, an expansive indoor kitchen & a full outdoor kitchen. The residence's amenities include an

Jason Friedman Daniel Gale Sothebys Intl Rlty

6 Spring Hill Ln, Old Westbury, NY 11568
/42
$4,495,000
- 7 Beds
- 6.5 Baths
- 4,974 Sq Ft
9 Lincoln St, Sag Harbor, NY 11963

Nestled in one of Sag Harbor Village's most desirable waterfront communities, this new construction home offers an unparalleled blend of luxury and coastal charm. With 4,974 square feet of meticulously designed living space, this seven-bedroom, six-and-a-half-bathroom estate is set on a tranquil .51-acre parcel. Situated just moments from the vibrant heart of the village and a private community

Thomas Cavallo Douglas Elliman Real Estate

9 Lincoln St, Sag Harbor, NY 11963
/36
$14,500,000
- 6 Beds
- 6.5 Baths
- 6,000 Sq Ft
70 Kettle Hole Rd, Montauk, NY 11954

Experience unparalleled luxury and modern comfort in this exceptional 6-bedroom, 6.5-bathroom bayfront estate, ideally positioned on a secluded acre with direct access to a private beach. Built in 2023 by Martin Architects and meticulously crafted by 4MA, this expansive residence spans approximately 6,000 square feet, offering breathtaking water views from nearly every room. Key features include

Chris Coleman Compass

70 Kettle Hole Rd, Montauk, NY 11954
/36
$2,950,000
- 7 Beds
- 4.5 Baths
- 4,651 Sq Ft
106 Willow Rd, Woodmere, NY 11598

Welcome to this Palatial 7 Bedroom, 4.5 Bathroom Grand Brick Center Hall Colonial, designed for luxurious living and entertaining! Nestled on a stunning property, it features a circular driveway and a heated in-ground pool. This mansion like home boasts magnificent sized rooms throughout. As you enter, you are greeted by a breathtaking two-story entry hall with a circular staircase. The spacious

Irene Steiner BERKSHIRE HATHAWAY

106 Willow Rd, Woodmere, NY 11598
/28
$1,980,000 Open Sun 12:30PM - 3:30PM
- 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
/49
$14,750,000
- 5 Beds
- 8 Baths
- 5,000 Sq Ft
207 Madison St, Sag Harbor, NY 11963

Set in the heart of Sag Harbor Village, 207 Madison Street stands as both a work of architecture and a living chronicle of local history. Originally built in 1841 by Col. Henry Wentworth Hunt - publisher of The Sag Harbor Corrector, which later became The Sag Harbor Express - the house sheltered three generations of the Hunt-Johnson family before becoming a beloved gathering place for hosts Joe

Hedgerow Exclusive Team Hedgerow Exclusive Properties

207 Madison St, Sag Harbor, NY 11963
/27
$4,700,000
- 5 Beds
- 5.5 Baths
- 5,169 Sq Ft
12 Fish Cove Rd, Southampton, NY 11968

Built in 2005 and gracefully sited on 1.18 acres overlooking North Sea Harbor's peaceful Fish Cove, this 5,100± sq. ft. residence captures the essence of Hamptons waterfront living. Expansive glass windows and French doors fill the interiors with natural light and frame serene harbor views from nearly every room. The main level offers a gracious entry foyer, a generous kitchen with premium

Dawn Petrillo Sothebys Int'l Realty Hamptons

12 Fish Cove Rd, Southampton, NY 11968
/46
$5,495,000
- 8 Beds
- 7.5 Baths
- 8,109 Sq Ft
58 Country Club Dr, Southampton, NY 11968

Introducing a breathtaking masterpiece nestled in the heart of Southampton’s coveted East End. This brand-new custom estate spans an impressive 7,485 square feet on a lush half-acre, drenched in natural light and designed to enchant at every turn. With 8 luxurious bedrooms and 8.5 opulent baths, every corner of this home radiates timeless sophistication. The bespoke kitchen is a culinary dream,

Louis Bougatsos Coldwell Banker Reliable R E

58 Country Club Dr, Southampton, NY 11968
/33
$12,575,000
- 5 Beds
- 4.5 Baths
- 4,110 Sq Ft
322 Rose Hill Rd, Water Mill, NY 11976

Nestled in the heart of Water Mill South, this historic luxury estate is a rare opportunity to own a masterpiece of Shingle Style architecture. Renovated in 2007 and conceived and built in 1884 by Henry Turbell Rose, Rosemary Lodge stands as a testament to exceptional craftsmanship and enduring elegance. Just minutes from the ocean, 0.93-acre grounds featuring a 4,110-square-foot residence, pool

Steven Dorn Brown Harris Stevens Hamptons

322 Rose Hill Rd, Water Mill, NY 11976
/23
$3,349,800
- 5 Beds
- 4.5 Baths
- 4,313 Sq Ft
52 Woodland Rd, Roslyn, NY 11576

Welcome to 52 Woodland Road – Newly Renovated Luxury in Roslyn! Set on nearly half an acre in the highly rated Roslyn School District, this stunning 4,300 sq. ft. home offers 5 bedrooms and 4.5 baths with exceptional attention to detail throughout. The first floor features a spacious living room, formal dining room, and a den with fireplace. The brand-new chef’s kitchen boasts high-end

Derek Greene Greene Realty Group

52 Woodland Rd, Roslyn, NY 11576
/38
$4,995,000 Open Sun 11AM - 12:30PM
- 5 Beds
- 5.5 Baths
- 4,200 Sq Ft
166 Ferry Rd, Sag Harbor, NY 11963

Welcome to 166 Ferry Rd, a luxurious black and white batten board home nestled on .48 acres in the picturesque hamlet of North Haven, Sag Harbor. This exquisite new construction offers a total of 4,200+/-sf of thoughtfully designed living space, featuring five bedrooms and five full and one half baths. Step inside to a grand great room, complete with a wood-burning fireplace, that seamlessly

Jacalyn Worth William Raveis (Southampton)

166 Ferry Rd, Sag Harbor, NY 11963
/33
$1,799,000
- 5 Beds
- 4.5 Baths
9 Flower Hill Ct, Huntington, NY 11743

In a quiet cul-de-sac near Huntington Bay, you will find the perfect blend of elegant indoor living and outdoor beauty in this stunning 5-bedroom, 4.5 bathroom center hall colonial. The spacious living and dining rooms feature hardwood floors and custom millwork, ideal for gathering and entertaining. The gourmet eat-in kitchen includes top-tier appliances, a large island, and a side-by-side

Kacey Knauer Signature Premier Properties

9 Flower Hill Ct, Huntington, NY 11743
/30
$987,000
- 5 Beds
- 4.5 Baths
- 2,467 Sq Ft
883 Mckenna Ave, North Baldwin, NY 11510

WELL MAINTAINED SINGLE FAMILY DETACHED PROPERTY ON CORNER LOT WITH INGROUND HEATED SWIMMING POOL, XXX LARGE 2 LIVING ROOMS, SEPARATE DINNING, GOURMET CHEF KITCHEN, 5 BEDROOMS WITH 3 FULL BATHROOOMS, AND SPACIOUS BACKYARD - PERFECT FOR GATHERINGS AND BBQS., PLAY GROUND AND GARDENS (ALL IN ONE) THIS RARE FIND PROPERTY PRESENTS OPPORTUNITY TO LIVE. CATHEDRAL / VAULTED CEILINGS, HIGH HERTZ LIGHTS,

SAM AJIBOLA AJAYI Voro LLC

883 Mckenna Ave, North Baldwin, NY 11510
/22
$615,000
- 5 Beds
- 3 Baths
- 2,015 Sq Ft
7 Carnaby Ave, Coram, NY 11727

Welcome to this beautifully updated Cape Cod style residence, perfectly situated mid block on a quiet tree lined street. This inviting 5 bedroom, 3 bath home offers fresh paint throughout. The open concept kitchen and living room create an ideal space for entertaining. It features a new kitchen with stainless appliances. Sliding doors off the living room leads you to a freshly painted deck

Jean Paul Commisso Cornerstone R E Services LLC

7 Carnaby Ave, Coram, NY 11727
/33
$9,900,000
- 7 Beds
- 7.5 Baths
- 8,100 Sq Ft
18 Hicks Ln, Port Washington, NY 11050

Welcome to a legacy property for you to secure for generations to come. The 5.7 Acres are a secluded Oasis. With paths and winding drives, sitting areas and gardens. There is a cottage at the foot of the property standing sentry along the brick columns that secure the two entry drives with majestic iron gates. Please refer to the survey attached to get a representation of how well this property

Timothy Serignese BERKSHIRE HATHAWAY

18 Hicks Ln, Port Washington, NY 11050
/33
$4,295,000
- 6 Beds
- 6.5 Baths
- 5,400 Sq Ft
25 Liberty St, Westhampton Beach, NY 11978

In the heart of Westhampton Beach Village, just a short walk to boutique shopping and dining on Main Street, you'll find this brand-new construction waiting to welcome you home. Set on just under half an acre, this stunning residence offers three spacious levels of open living space with soaring ceilings, custom woodwork, and elegant detailing throughout. The home features six bedrooms and six

Colleen Graning Douglas Elliman Real Estate

25 Liberty St, Westhampton Beach, NY 11978
/34
$6,500,000
- 6 Beds
- 7.5 Baths
- 8,861 Sq Ft
4 Old Wagon Ln, Old Westbury, NY 11568

**Price Reduction $6,500,000.** Welcome to 4 Old Wagon Lane in Old Westbury, NY. The luxurious estate sits on a 4.01 acre well-manicured property with a beautiful stunning brick home of approximately 8,900 square feet. Step into the utmost of luxury in this finely detailed home. The high quality craftsmanship is evident though-out the 1st floor’s formal dining room, living room, piano room and

Anthony Garcia Cast Iron Real Estate Company

4 Old Wagon Ln, Old Westbury, NY 11568
/27
$9,100,000
- 6 Beds
- 12 Baths
- 17,500 Sq Ft
5 Longwood Rd, Port Washington, NY 11050

Custom designed and built with unparalleled quality and detail for the most discerning home buyer. Extraordinary finishes. Extravagant space. A superior complement of amenities. All of this and more make 5 Longwood Road one of Sands Point's most distinguished homes. Sited on a magnificently landscaped 2-acre property with stunning in-ground pool. You've earned it. You deserve it. What are

Maggie Keats Douglas Elliman Real Estate

5 Longwood Rd, Port Washington, NY 11050
/2
$4,200,000
- 5 Beds
- 4.5 Baths
- 5,659 Sq Ft
45 Pelican Ct, Syosset, NY 11791

Purchase As Is for $1,550,000 or Purchase 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

Nancy Davila Campo Four Seasons Realty Team

45 Pelican Ct, Syosset, NY 11791
/49
$4,900,000
- 6 Beds
- 6.5 Baths
- 8,750 Sq Ft
63 Dyke Rd, Setauket, NY 11733

Magnificent Country Waterfront Estate on shy 3 acres tucked away in Strong's Neck, Setauket..1000' on Little Bay w. private dock , Privacy with rustic elegance and designed for large family with top of the line furnishings. 5 Bedrooms 6.5 baths with grand entertainment room w. large stone Frpl and soaring ceilings, beautiful custom lighting and a full bar area, The Kitchen is outfitted with

Linda Hickey Hickey & Smith REALTORS

63 Dyke Rd, Setauket, NY 11733
/34
$4,475,000
- 6 Beds
- 4.5 Baths
- 5,480 Sq Ft
13 Lighthouse Rd, Great Neck, NY 11024

An exceptional opportunity on one of the most prestigious streets in the Village of Kings Point, this sun-filled six-bedroom ranch offers gracious proportions and an easy, elegant flow. Set on a private, level property, the residence provides approximately 5,480 square feet of total living space thoughtfully designed for both everyday living and entertaining. The main level features a

Irene Sarraf Daniel Gale Sothebys Intl Rlty

13 Lighthouse Rd, Great Neck, NY 11024
/45
$9,995,000
- 8 Beds
- 9.5 Baths
- 9,070 Sq Ft
7 Ashwood Ct, East Hampton, NY 11937

Nestled on two picturesque acres, this stunning property features a private driveway and gated entry. Constructed in 2020 by renowned builder Larry Kane, the home seamlessly blends traditional and modern elements, and is abundant with natural light throughout. Upon entering through the front door, you are greeted by a gourmet chef's kitchen boasting an expansive island for seating, complemented

Chris Coleman Compass

7 Ashwood Ct, East Hampton, NY 11937
/45
$1,699,999
- 7 Beds
- 4 Baths
- 3,864 Sq Ft
28 S Montgomery Ave, Bay Shore, NY 11706

Welcome to 28 S. Montgomery Avenue — a distinguished Dutch Colonial set on nearly an acre of waterfront property in Bay Shore. Built in 1895, this timeless home blends historic character with thoughtful modern updates. Featuring seven bedrooms and two full plus two half baths, it offers space for both elegant entertaining and comfortable daily living. The formal living room with fireplace and

Tammy Ramsay Eric G Ramsay Jr Assoc LLC

28 S Montgomery Ave, Bay Shore, NY 11706
/28
$5,995,000
- 7 Beds
- 9 Baths
- 10,585 Sq Ft
8 Barnes Ave, Northwest Harbor, NY 11937

Set amidst lush greenery in one of the Hamptons' most serene enclaves, this breathtaking 10,585-square-foot contemporary estate is a true sanctuary of modern luxury and architectural brilliance. Designed to seamlessly integrate with its natural surroundings, this seven-bedroom, seven-bathroom residence offers an unparalleled living experience, combining sophisticated design with state-of-the-art

Christopher Ritchey Compass

8 Barnes Ave, Northwest Harbor, NY 11937
/10
$12,750,000
- 7 Beds
- 8.5 Baths
- 10,000 Sq Ft
16 Arbor Path, East Hampton, NY 11937

This refined modern is unparalleled. Set on 1.67 acres within the coveted Bell Estate in Amagansett and bordering over 50 acres of reserve, the setting affords exceptional privacy and a locational advantage you will love. A perfectly positioned residence just minutes to Amagansett's Main Street, the ocean, and the bay. Meticulous execution, thoughtful design, and noticeable attention to detail

William Kuneth Brown Harris Stevens Hamptons

16 Arbor Path, East Hampton, NY 11937
/27
$1,099,000
- 5 Beds
- 4 Baths
- 3,382 Sq Ft
5 Lafayette Place, Massapequa, NY 11758

Welcome to 5 Lafayette Place in the heart of Massapequa Shores — a spacious and versatile 5-bedroom, 4-bathroom home set on an oversized 14,000+ sq ft property. This beautifully laid out residence offers a traditional and functional floor plan featuring a formal living room and formal dining room — perfect for entertaining and hosting gatherings. The generous bedroom count and full bathrooms

Nikko Hiotis BERKSHIRE HATHAWAY

5 Lafayette Place, Massapequa, NY 11758

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Homes for Sale in Long Island, NY with 5-Bedrooms & a Private Pool

5-Bedroom Homes for Sale with Private Pool in Long Island, NY

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