Homes for Sale in Westchester County NY with 5-Bedrooms & a Private Pool

/47
$5,195,500
- 6 Beds
- 8 Baths
- 7,772 Sq Ft
1 Garden Rd, Scarsdale, NY 10583

Magnificent stone and clapboard Colonial set on over an acre of beautifully landscaped, level property with heated in-ground saltwater pool. Offering approximately 7,772 square feet of interior living space (not including attic and basement), this solidly constructed residence combines classic architecture with exceptional craftsmanship and modern comfort. Highlights include 9-foot ceilings on

Mark Nadler Berkshire Hathaway HS NY Prop

1 Garden Rd, Scarsdale, NY 10583
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/48
$4,500,000
- 5 Beds
- 7 Baths
- 7,608 Sq Ft
150 Old Farm Rd N, Chappaqua, NY 10514

1906 Grandeur. 2026 Luxury: The Ultimate Gated Sanctuary. Perched majestically atop a private hilltop, this gated 7,800-square-foot, five-bedroom estate presents a rare convergence of Gilded Age prestige and contemporary luxury. Believed to have been commissioned in 1906 for railroad magnate A.H. Smith, the residence has been masterfully renovated to honor its historic soul, featuring original

Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

150 Old Farm Rd N, Chappaqua, NY 10514
/42
$12,400,000
- 5 Beds
- 5.5 Baths
- 7,447 Sq Ft
3031 Purchase St, Purchase, NY 10577

A Contemporary Estate Shaped by Light and Wood on 3.5 Serene AcresAn exquisite modern compound designed for expansive living, this residence is distinguished by its rare collection of purpose-built structures and amenities: a custom-designed Japanese tea house, separate party barn, dedicated pottery/art studio, European KLAFS sauna suite, in-ground pool, and serene Zen-inspired grounds — all

Wendy Alper Julia B Fee Sothebys Int. Rlty

3031 Purchase St, Purchase, NY 10577
/49
$2,775,000
- 5 Beds
- 6.5 Baths
- 7,052 Sq Ft
496 Long Ridge Rd, Bedford, NY 10506

Welcome to an incredible retreat in beautiful Bedford, NY! This stunning 5-bedroom, 6.5-bath home spans over 10,000 square feet of elegant living space on nearly two acres of private land. From the moment you arrive, you will feel the warmth and sophistication of this well-designed residence.Step inside to find a gracious formal living and dining room that sets the tone for memorable

Robin Bartholomew Berkshire Hathaway HS NE Prop.

496 Long Ridge Rd, Bedford, NY 10506
/34
$2,495,000
- 5 Beds
- 5.5 Baths
- 6,054 Sq Ft
4 Hageman Ct, Katonah, NY 10536

Now Offered at an Improved Price! Set behind a gated entrance, this elegant Colonial blends timeless architecture with modern luxury and thoughtful updates throughout. The home offers an open, well-designed layout with a chef’s kitchen featuring an oversized granite island, breakfast area, and high-end professional appliances seamlessly connecting to the dining room and great room with a

Irina Baskakova Compass Greater NY, LLC

4 Hageman Ct, Katonah, NY 10536
/38
$3,895,000 Open Sun 11AM - 1PM
- 6 Beds
- 3.5 Baths
- 6,663 Sq Ft
54 Lincoln Ave, Rye Brook, NY 10573

Set on 3.19 acres of tranquil woodland in a coveted Rye Brook enclave, this exceptional contemporary residence offers privacy and seamless indoor-outdoor living. Thoughtfully renovated to blend modern luxury with its Frank Lloyd Wright-inspired design, the 6,663 sq ft home with 6 bedrooms and 4 baths showcases dramatic open spaces, clean architectural lines, and natural materials throughout. An

Wendy Alper Julia B Fee Sothebys Int. Rlty

54 Lincoln Ave, Rye Brook, NY 10573
/8
$1,645,000
- 5 Beds
- 5 Baths
- 4,091 Sq Ft
11 Florence Dr, Mahopac, NY 10541

Welcome to Somers Estates, one of Somers newest subdivisions. Custom designed Farm House where value meets Luxury. Situated on over a two acre level lot with space for a pool. Front covered porch with standing seam roof. Dramatic Front Foyer, entry, and Family room with fireplace. Formal dining room, Chefs Kitchen, living room, office, bath, and mudroom on first floor that leads to the three car

Mario Sclafani RE/MAX Classic Realty

11 Florence Dr, Mahopac, NY 10541
/42
$5,499,000
- 5 Beds
- 8 Baths
- 10,114 Sq Ft
16 Wrights Mill Rd, Armonk, NY 10504

Set within Armonk’s most prestigious enclave, Wrights Mill Estates, this custom Hamptons chic, stone and shingle Colonial is a masterwork of timeless elegance and resort-style living. Bespoke interiors unfold with 10-foot ceilings, quarter-sawn oak floors, fine cashmere wall coverings and extensive millwork. The white Peacock style kitchen, with 2" Calacatta Gold counters, exemplify style and

Brian Milton Compass Greater NY, LLC

16 Wrights Mill Rd, Armonk, NY 10504
/30
$1,850,000 Open Sun 1PM - 3PM
- 5 Beds
- 3.5 Baths
- 2,650 Sq Ft
15 Hillside Rd, Bronxville, NY 10708

This upgraded turn-key home is ideal for permanent residence or for weekend escapes! Situated in picture perfect Elmsmere Estates, with a sprawling backyard ready for entertaining plus a full size pool. All this under $2M !! Boasting a total of 5 bedrooms, 3.5 baths, a bonus room and a fabulous pool and backyard area, complete with a playset. Enter the welcoming foyer, and you will find a

Patricia Benna Houlihan Lawrence Inc.

15 Hillside Rd, Bronxville, NY 10708
/44
$9,950,000
- 6 Beds
- 9 Baths
- 7,792 Sq Ft
106 Premium Point, New Rochelle, NY 10801

A rare and distinguished waterfront offering, located just 30 minutes from Manhattan, set within the exclusive, gated enclave of Premium Point. Masterfully crafted by Thompson-Raissis Architects, the home was created to capture breathtaking water views from nearly every room, featuring balconies and floor-to-ceiling retractable windows, all executed with the highest caliber of finishes. A

Jessica Sigmund Compass Greater NY, LLC

106 Premium Point, New Rochelle, NY 10801
/50
$6,000,000
- 5 Beds
- 7 Baths
- 8,624 Sq Ft
109 Mamaroneck Rd, Scarsdale, NY 10583

An Iconic Georgian Colonial in Scarsdale’s Estate Section. This residence is more than just a home—it’s a legacy property and a sanctuary for those who appreciate the very best in life! This exceptional estate offers an unparalleled lifestyle with resort-style amenities, timeless elegance and unmatched privacy. This exquisite Brick Georgian Colonial, perched at the highest elevation in Scarsdale,

Liz Widulski Julia B Fee Sothebys Int. Rlty

109 Mamaroneck Rd, Scarsdale, NY 10583
/36
$4,575,000
- 6 Beds
- 9.5 Baths
- 9,463 Sq Ft
23 Pheasant Dr, Rye, NY 10580

This is the home that you have been waiting for! A genuine summer retreat that is a true testament to grandeur, privacy, and refined living. Set on 1.47 meticulously landscaped acres in coveted Rye PO, this remarkable estate offers both seclusion and convenience, located on a quiet road adjacent to the prestigious Westchester Country Club, just 1.6 miles from the Rye Metro-North train station and

Annalise Stack Compass Greater NY, LLC

23 Pheasant Dr, Rye, NY 10580
/35
$6,995,000
- 6 Beds
- 10 Baths
- 10,627 Sq Ft
21 Lincoln Ln, Purchase, NY 10577

A Westchester masterpiece perfectly combining high end newer construction with A+ location. Set behind stone pillars, with impressive approach, courtyard and incredible curb appeal, this sophisticated, all stone, newer built estate is like no other on the market in this price range, with understated elegance, classic design and enhancement by sleek/modern amenities. Set majestically toward the

Louis Katsoris Julia B Fee Sothebys Int. Rlty

21 Lincoln Ln, Purchase, NY 10577
/35
$7,495,000
- 8 Beds
- 9 Baths
- 13,554 Sq Ft
99 Mamaroneck Rd, Scarsdale, NY 10583

This meticulously renovated Murray Hill Estate welcomes sophisticated living and lavish entertaining on 1.76 acres of lush, park-like grounds. The sprawling 1910 colonial has been elevated with designer interiors, upgraded mechanicals, hardwood floors, custom wall coverings and new designer lighting throughout. A grand entry hall opens to a massive living room with fireplace, terrace, family room

Heather Harrison Compass Greater NY, LLC

99 Mamaroneck Rd, Scarsdale, NY 10583
/47
$2,149,000
- 6 Beds
- 5 Baths
- 5,940 Sq Ft
27 Cat Ridge Rd, North Salem, NY 10560

Welcome to 27 Cat Ridge Road—an elegant 6-bedroom estate featuring 3 full baths and 2 powder rooms, gracefully set on 4.5 private, picturesque acres in the heart of North Salem. This exceptional property offers the perfect balance of comfort, sophistication, and convenience. Ideally located just 8 minutes from the Goldens Bridge Metro-North Station and I-684, it provides an easy approximately

Jeliana Melendez Christie's Int. Real Estate

27 Cat Ridge Rd, North Salem, NY 10560
/38
$3,500,000
- 7 Beds
- 7 Baths
- 5,502 Sq Ft
83 Somerstown Rd, Ossining, NY 10562

Steeped in local history and once owned by the Gilded Age Van Cortlandt family, gracious Rose Lodge is an inviting and beautifully restored historic estate—not landmarked—offering modern living and exceptional privacy on 17.9 acres. The property enjoys sweeping views across a perfectly sited in-ground pool, terraced gardens, expansive flat croquet lawn, and private lake, creating a serene country

Dalia Valdes Julia B Fee Sothebys Int. Rlty

83 Somerstown Rd, Ossining, NY 10562
/50
$4,220,000
- 5 Beds
- 4.5 Baths
- 4,796 Sq Ft
415 Grace Church St, Rye, NY 10580

EXTRAORDINARY RYE ESTATE; 2 HOMES on 5 SPRAWLING ACRES.....A RARE FIND! 5BR / 4.5Bth STATELY COLONIAL incl nearly 5000SF of Living Space + Modern 3BR / 3Bth 1600+SF GUESTHOUSE. MAIN HOUSE offers Grand Entry Foyer, Formal Dining Room, Livingroom w/ Wood-Burning Fireplace & Study. Eat-in kitchen w/ Lg Center Island, Stainless Steel Appliances + Terrace with Scenic Views. Adjoining Warm & Inviting

Dana Topper ERA Insite Realty Services

415 Grace Church St, Rye, NY 10580
/9
$5,695,000
- 6 Beds
- 8.5 Baths
- 9,147 Sq Ft
15 Stone Bridge Rd, Purchase, NY 10577

Stunning new home at "Sarosca Farm Estates", this home is at the end of the cul-de-sac on Stone Bridge Road on 1.7 acres, and has all the amenities you can ask for. The 1st floor features an open floor plan including kitchen with top of the line appliances, large center island, breakfast area, family room with fireplace, private office with a full bath, spacious dining room, back stairs and mud

Joseph Stilo Julia B Fee Sothebys Int. Rlty

15 Stone Bridge Rd, Purchase, NY 10577
/41
$5,995,000
- 5 Beds
- 6.5 Baths
- 8,059 Sq Ft
2 Barry Ct, Katonah, NY 10536

Tucked away on a tranquil cul-de-sac in the prestigious Town of Bedford, this masterfully reimagined estate defines the next generation of Bedford luxury real estate—while offering a rare opportunity as the perfect summer escape from New York City. Just a short, convenient journey from the energy of Manhattan, 2 Barry Court provides a seamless transition from city living to serene countryside

Margaret Grasso Berkshire Hathaway HS NY Prop

2 Barry Ct, Katonah, NY 10536
/40
$1,298,000
- 5 Beds
- 5.5 Baths
- 3,764 Sq Ft
5 Forkland Ln, Dobbs Ferry, NY 10522

Tucked away in the picturesque village of Dobbs Ferry, this expansive residence effortlessly combines comfort, flexibility, and timeless appeal. Encompassing more than 3,700 sq ft on nearly one private acre, this property is a rare opportunity to create your forever home in one of Westchester’s most sought-after Rivertowns. Inside, you’ll find five spacious bedrooms, five full baths, and a

Iris Kalt Berkshire Hathaway HS NY Prop

5 Forkland Ln, Dobbs Ferry, NY 10522
/4
$1,199,000
- 7 Beds
- 5 Baths
- 2,930 Sq Ft
26 Glen Ave, Port Chester, NY 10573

Come view this massive three story; 7 bed, 5 bathroom home, on a corner lot with a full size swimming pool and furnished basement. Located in the heart of beautiful Port Chester. This historic home has all the original details and charm from the early 1900's. Amazing oversized corner lot.

Matthew Bizzarro Bizzarro Agency, LLC

26 Glen Ave, Port Chester, NY 10573
/47
$5,195,000
- 5 Beds
- 6.5 Baths
- 8,366 Sq Ft
10 Cooper Rd, Scarsdale, NY 10583

Experience resort-style living in this stunning 8,366 sq ft Mediterranean-inspired colonial, perfectly situated on 1.22 acres in Scarsdale’s prestigious Murray Hill Estate area. Designed for both grand entertaining and comfortable everyday living, this architectural masterpiece features soaring ceilings, walls of windows, and exquisite millwork throughout. Step into a dramatic marble foyer with a

Alisa Kaplan Julia B Fee Sothebys Int. Rlty

10 Cooper Rd, Scarsdale, NY 10583
/33
$17,500,000
- 8 Beds
- 13 Baths
- 17,160 Sq Ft
Unlisted Address

This spectacular limestone French Manor estate sits on 10+ acres on Converse Lake with 100'+ of lakefront in the beautiful and secluded Conyers Farm, a guard gated community with private security. Custom designed for the current owners by architect James Davis, this meticulous home features impressive attention to detail. The main & garden level of the home are ideal for entertaining with an

Danielle Claroni Sotheby's International Realty

Unlisted Address
/50
$30,000,000
- 8 Beds
- 12 Baths
- 14,680 Sq Ft
2525 Purchase St, Purchase, NY 10577

Symbolically built for the founding family of Purchase, this iconic estate presents an exclusive opportunity to acquire one of the most significant and unique New York residential real estate properties available in recent years. The epitome of a true suburban compound, this grand residence is uniquely situated within quick reach of New York City, water and golf amenities, and all means of

Louis Katsoris Julia B Fee Sothebys Int. Rlty

2525 Purchase St, Purchase, NY 10577
/35
$2,975,000
- 6 Beds
- 8 Baths
- 5,436 Sq Ft
9 Oregon Rd, Bedford Corners, NY 10549

Rare Estate Compound. Surrounded by bucolic countryside, nearly seven acres in an area of foremost country homes and estates. Verdant rolling lawns lined by old stone walls, specimen trees, apple orchard and beautifully flowering shrubs. Rambling Country Colonial, circa 1925, the former home of actor EG Marshall. Completely updated with nicely proportioned rooms, substantial moldings, extensive

Mary Dowdle Ginnel Real Estate

9 Oregon Rd, Bedford Corners, NY 10549
/33
$8,500,000
- 7 Beds
- 6.5 Baths
- 8,602 Sq Ft
149 Narrows Rd, Bedford Hills, NY 10507

Skyland Farm. Set on one of the most prestigious country lanes, this Bedford estate sits on over 25 acres of spectacular property with rolling land, scenic views and gorgeous landscape. The up-to-the minute, beautifully executed 5 bedroom main residence has a spectacular great room as its focal point with a fieldstone fireplace, barn beam ceilings and an open style designer kitchen extending to

Angela Kessel Houlihan Lawrence Inc.

149 Narrows Rd, Bedford Hills, NY 10507
/49
$3,175,000
- 5 Beds
- 5.5 Baths
- 5,958 Sq Ft
1 St Marys Convent, Peekskill, NY 10566

Perched high above the Hudson River, 1 St. Mary’s Convent—also known as St. Joseph’s House—is a distinguished 5-bedroom, 5.5-bath luxury manor offering nearly 6,000 square feet of living space on 4.7 private acres. Originally designed by renowned architect Henry Martin Congdon for the first Episcopalian Order in the United States, this remarkable home is rich with history as part of Fort Hill, a

Andrew Rogovic Christie's Int. Real Estate

1 St Marys Convent, Peekskill, NY 10566
/36
$3,650,000
- 6 Beds
- 10.5 Baths
- 12,872 Sq Ft
40 Polly Park Rd, Rye, NY 10580

Major reduction . Home owner wishes to move on. Nestled on over two acres of secluded, picturesque grounds, this exceptional, one-of-a-kind contemporary estate is a rare opportunity for luxury living. It boasts a stunning pool with hot tub ,waterfall, a pavilion with full bath and changing rooms, and a tennis court. The striking architecture seamlessly blends indoor and outdoor living. Expansive

Alix Prince Julia B Fee Sothebys Int. Rlty

40 Polly Park Rd, Rye, NY 10580
/40
$7,450,000
- 6 Beds
- 10 Baths
- 14,000 Sq Ft
284 W Patent Rd, Mount Kisco, NY 10549

Just one hour from Manhattan, this extraordinary Bedford Corners estate offers the ultimate in privacy, scale, and resort-style living. Encompassing 14,000 square feet of custom design on 11.27 gated acres, the residence combines timeless sophistication with every modern amenity. Perfect for either a primary or weekend residence. A Retreat for Living, Working and EntertainingThe

Harlene Friedman Corcoran MH, LLC

284 W Patent Rd, Mount Kisco, NY 10549
/35
$3,450,000
- 6 Beds
- 5.5 Baths
- 8,200 Sq Ft
20 Bessel Ln, Chappaqua, NY 10514

Nestled in breathtaking natural surroundings, this modern architectural masterpiece by renowned designer Myron Goldfinger offers three levels of striking contemporary design. The residence features a soaring three-story curved ceiling, a dramatic floating staircase, and expansive open-plan living and entertaining spaces that frame the home’s private setting. The main-level primary suite provides

Tianying Xu Houlihan Lawrence Inc.

20 Bessel Ln, Chappaqua, NY 10514
/48
$5,500,000
- 7 Beds
- 5.5 Baths
- 5,700 Sq Ft
433 Arcady Rd, Ossining, NY 10562

Old Dam Farm — A Rare Hudson Valley Legacy Set on nearly 40 pristine acres bordered by over 100 acres of protected New York City watershed land, Old Dam Farm offers an unparalleled combination of natural beauty, history, and lifestyle. This remarkable estate overlooks the sparkling Croton Reservoir, creating a backdrop of breathtaking views in every season. At its heart stands a spectacular

Nancy Kennedy

433 Arcady Rd, Ossining, NY 10562
/50
$3,300,000
- 5 Beds
- 7 Baths
- 7,931 Sq Ft
36 Revolutionary Rd, Briarcliff Manor, NY 10510

The Essence of Westchester Luxury. A Grand Briarcliff Manor Estate sited on 3.83 Private Acres. Perfectly positioned between the Hudson River and Sleepy Hollow Country Club. World-class dining, shopping and Metro North train are nearby, blending convenience with serene privacy. The stately home boasts five spacious ensuite bedrooms, including a spectacular primary suite with a cozy fireplace, a

Elaine Wasserman Houlihan Lawrence Inc.

36 Revolutionary Rd, Briarcliff Manor, NY 10510
/49
$4,495,000
- 7 Beds
- 10 Baths
- 13,923 Sq Ft
7 Rockledge Rd, Rye, NY 10580

$15 Million Dollar value being sold in an estate sale for an amazing price! Unrivaled grandeur with an idyllic Tuscan-countryside vibe! Introducing one of Westchester County’s most magnificent Estates, beautifully situated high on an exquisite tree-lined rise just minutes from Rye. This private sanctuary is nestled on 5.2 acres of manicured grounds with distant water views of Long Island Sound.

Wendy Alper Julia B Fee Sothebys Int. Rlty

7 Rockledge Rd, Rye, NY 10580
/48
$5,500,000
- 9 Beds
- 4.5 Baths
- 8,329 Sq Ft
57 Cobb Ln, Tarrytown, NY 10591

Perched above the Hudson River on 3.5 gated acres in the heart of Tarrytown is a stunninghome historically known as “Whitehall.” Built in 1929, this grand residence offers sweeping,unobstructed views of the river and Mario Cuomo Bridge—and all the timeless charm of aEuropean manor, just 36 minutes from Grand Central.The property is a world unto itself: a fenced-in pool and hot tub

Christopher Cawley Corcoran Legends Realty

57 Cobb Ln, Tarrytown, NY 10591
/8
$6,650,000
- 7 Beds
- 7.5 Baths
- 8,943 Sq Ft
21 Autenrieth Rd, Scarsdale, NY 10583

This fully rebuilt, renovated and expanded brick Colonial sits proudly on a half-acre of level, private property with a luxurious pool house and pool. Perfectly located just a stone’s throw from Scarsdale Village and train, this home blends timeless architectural details with today’s most sought-after amenities. The first floor impresses with high ceilings, rich millwork, and a seamless flow for

Randi Culang Compass Greater NY, LLC

21 Autenrieth Rd, Scarsdale, NY 10583
/37
$12,000,000
- 5 Beds
- 5.5 Baths
- 7,538 Sq Ft
48 Raafenberg Rd, Tarrytown, NY 10591

Historic Winterburn Farm is a spectacular 42 acre estate compound with sweeping views of the Hudson and Palisades beyond. Located in Westchester's bucolic hamlet of Pocantico Hills, the property offers the beauty and serenity of the country within 30 miles of Manhattan. The main residence, designed for Rodman Rockefeller by Architect Richard P. Donahue, is mid century modern. The home's central

David Turner Compass Greater NY, LLC

48 Raafenberg Rd, Tarrytown, NY 10591
/41
$16,000,000 Open Sun 2PM - 4PM
- 8 Beds
- 13 Baths
- 13,481 Sq Ft
104 Premium Point Rd, New Rochelle, NY 10801

The Bluffs at Premium Point introduces ultra-luxury living at the absolute pinnacle of the Premium Point market, setting a new standard within Mamaroneck’s most exclusive, guard-gated peninsula. One of only the coveted “Big Four” landmark estates in this 24/7 secured enclave, this brand-new architectural masterpiece occupies a rare 1.3-acre waterfront sanctuary with horizon-level views found

Wendy Alper Julia B Fee Sothebys Int. Rlty

104 Premium Point Rd, New Rochelle, NY 10801
/36
$17,500,000
- 8 Beds
- 13 Baths
- 17,160 Sq Ft
17 Cowdray Park Dr, Armonk, NY 10504

This spectacular limestone French Manor estate sits on 10+ acres on Converse Lake with 100'+ of lakefront in exclusive Conyers Farm, a guard gated community with private security. Custom designed for the current owners by architect James Davis, this meticulous home features impressive attention to detail. The main & garden level of the home are ideal for entertaining with an oversized great room,

Danielle Claroni Sotheby's International Realty

17 Cowdray Park Dr, Armonk, NY 10504
/34
$1,850,000 Coming Soon
- 5 Beds
- 5.5 Baths
- 3,736 Sq Ft
3 Penny Ln, Scarsdale, NY 10583

Three Penny Lane is a beautiful, gracious colonial with a circular driveway - on a lovely street in the Edgemont school district. This house is perfectly well maintained, with every room exceptionally large and sunny. The master bedroom is huge and features a cathedral ceiling, sitting room, dressing room, and a luxurious bath. The heated pool is landscaped for privacy and the deck, which

Marilyn Berman Julia B Fee Sothebys Int. Rlty

3 Penny Ln, Scarsdale, NY 10583
/42
$4,900,000 Coming Soon
- 6 Beds
- 5.5 Baths
- 6,000 Sq Ft
161 Buxton Rd, Bedford Hills, NY 10507

Buxton Pond Farm, tucked quietly along a country Lane just minutes from the train, shops and schools of Bedford Hills, is a rare offering. Set on 11 pastoral acres surrounded by historic stone walls with sweeping lawns, mature trees, established gardens that grow food and flowers, and open pastures for animals, this beautiful farm offers a lifestyle rooted in nature, security, and sustainable

Kristine Blake Sotheby's International Realty

161 Buxton Rd, Bedford Hills, NY 10507

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