36

Homes for Sale near John Jay High School

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  • /12

    $835,000

    • 2 Beds
    • 1.5 Baths
    • 1,487 Sq Ft

    8 Hoyt St, South Salem, NY 10590

    A rare opportunity in the charming Truesdale Lake community of South Salem. This quaint cottage is in need of renovation and is being sold as-is, offering outstanding potential for restoration, investment, or new construction. Truesdale Lake is an 83-acre private lake community known for its peaceful setting, natural beauty, and long-established neighborhood character. Located in the Town of

    Jessica Lane

    Serhant LLC

    8 Hoyt St, South Salem, NY 10590
  • /42

    $2,500,000

    $200K PRICE DROP
    • 6 Beds
    • 7.5 Baths
    • 8,900 Sq Ft

    11 Lost Nations Rd, Pound Ridge, NY 10576

    Set on over two spectacular acres in a premier location in Pound Ridge, this custom built Colonial offers an extraordinary blend of scale, craftsmanship, and complete privacy. Tucked along a quiet country road, this home has exquisite architectural detail throughout that includes extensive custom millwork, gleaming hardwood floors, soaring ceilings, and spacious rooms that create an atmosphere of

    Agent Photo

    Nikki McMann

    William Raveis-New York LLC

    11 Lost Nations Rd, Pound Ridge, NY 10576
  • /36

    $2,150,000

    • 4 Beds
    • 3.5 Baths
    • 4,100 Sq Ft

    430 Harris Rd, Bedford Hills, NY 10507

    Privately sited on one of Bedford's most prestigious roads, this classic four-bedroom residence offers more than 4,000 square feet of refined space surrounded by the beauty of the Bedford countryside. Generous, light-filled family and formal rooms provide effortless living. At the heart of the home is a huge chef's kitchen with generous workspace, abundant storage, and room for everyone to

    Angela Kessel Houlihan Lawrence Inc.

    430 Harris Rd, Bedford Hills, NY 10507
  • /18

    $599,000

    • 2 Beds
    • 2.5 Baths
    • 1,451 Sq Ft

    30 Briar Ct, Cross River, NY 10518

    Welcome to this beautifully maintained two-bedroom, two-and-a-half-bathroom townhome in The Meadows of Cross River. This inviting home offers a spacious and thoughtfully designed layout with comfortable living spaces, quality finishes, and excellent community amenities.The first floor features an inviting entry foyer, a convenient powder room, and an eat-in kitchen with granite countertops, a

    Sheila Olivieri Prime Go Realty, Inc.

    30 Briar Ct, Cross River, NY 10518
  • /45

    $1,500,000

    • 3 Beds
    • 3 Baths
    • 2,964 Sq Ft

    18 Laurel Rd, South Salem, NY 10590

    Fresh, stylish, and thoughtfully designed, this exceptional new construction offers inviting spaces, abundant natural light, and carefully selected finishes. Set within a natural woodland setting, this home is well sited on a corner lot with a circular driveway approach and is nicely set back from the road. A dramatic foyer with clerestory windows welcomes you in, with extended sightlines through

    Michael Neeley William Raveis-New York LLC

    18 Laurel Rd, South Salem, NY 10590
  • /7

    $75,000

    • Land
    • 3.63 Acres
    • $20,661 per Acre

    0 Laurie Ln Unit KEY000152, Lewisboro, NY 10590

    Selling as is. Amazing opportunity to build new construction on 3.6 acres in the town of Lewisboro. Quiet neighborhood setting. Prior BOHA approval is dated 1986. Old BOHA is located in Documents

    Jayne Morelock Howard Hanna Rand Realty

    0 Laurie Ln Unit KEY000152, Lewisboro, NY 10590
  • /14

    $894,999

    • 4 Beds
    • 1.5 Baths
    • 2,500 Sq Ft

    9 Laurel Rd, South Salem, NY 10590

    Welcome to 9 Laurel Road, a spacious home set on 1.5 acres along a quiet residential street in the desirable South Salem area. Surrounded by mature trees and wooded views, the property offers a peaceful setting with plenty of privacy, a generous lawn, and expansive backyard space. The home features 4 bedrooms, hardwood floors, a spacious living room, dining area, eat-in kitchen, and a comfortable

    Blaise Nastasio Manhattan Network Inc

    9 Laurel Rd, South Salem, NY 10590
  • /23

    $915,000

    $10K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,851 Sq Ft

    17 Highview Rd, Pound Ridge, NY 10576

    This private and spacious home sits on 2.5 acres of beautiful land in Pound Ridge, and is the ideal Westchester retreat. It has that perfect mix of "peace and quiet" without being completely off the grid. With 4 bedrooms and 3 full bathrooms, you’ll have plenty of room for everyone. The versatile floor plan offers endless possibilities to make the space your own. Enjoy a bright eat-in kitchen

    Mark Boyland Keller Williams Realty Partner

    17 Highview Rd, Pound Ridge, NY 10576
  • /39

    $1,750,000

    • 4 Beds
    • 7 Baths
    • 3,738 Sq Ft

    60 Cherry St, Katonah, NY 10536

    Katonah, swim at your private oasis, this multi-functional home with in-law capacity, entertainment amenities, and office workspace is nestled on almost 3 acres of lush parklike property. Enjoy the ease of being close to town, elementary school, and Metro-North; this exceptional 3,738 sqft residence offers the perfect blend of tranquility and commuter convenience. Designed with flexible home

    Julia Lear Coldwell Banker Realty

    60 Cherry St, Katonah, NY 10536
  • /24

    $629,000

    • 2 Beds
    • 2 Baths
    • 1,468 Sq Ft

    230 Lakeside Dr, South Salem, NY 10590

    Gorgeous, completely updated, two bedroom with office and open loft/den townhome in the Katonah Lewisboro School District. The open living space is flooded with light, calming colors, soaring ceilings and a wood burning fireplace. The recently renovated eat in kitchen featuring stainless steel appliances, an enormous center island and deck access is the perfect place to entertain. A primary

    Patricia Hinkley Coldwell Banker Realty

    230 Lakeside Dr, South Salem, NY 10590
  • /32

    $4,995,000

    • 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 gated home defines the next generation ofBedford luxury real estate. Just a short, convenient jauntfrom the energy of Manhattan, 2 Barry Court provides a seamless transition from city living to serene countryside retreat, making it an idealresidence for those seeking fresh air,

    Angela Kessel Houlihan Lawrence Inc.

    2 Barry Ct, Katonah, NY 10536
  • /26

    $1,290,000

    • 4 Beds
    • 2.5 Baths
    • 2,520 Sq Ft

    5 Hampton Place, Katonah, NY 10536

    Katonah Hamlet: This classic 4 Bedroom Colonial is full of timeless charm and ready for the next owner to bring their personal touches. Featuring beautiful hardwood floors throughout, crown molding, a custom fireplace in the family room and an updated Kitchen with stainless appliances, this home offers a warm and inviting atmosphere with a traditional layout ideal for everyday living and

    Rita Carrozza Houlihan Lawrence Inc.

    5 Hampton Place, Katonah, NY 10536
  • /36

    $575,000

    • 1 Bed
    • 1.5 Baths
    • 1,451 Sq Ft

    23 Briar Ct, Cross River, NY 10518

    Welcome to your beautifully updated oasis at 23 Briar Court, nestled in The Meadows community within the Katonah-Lewisboro School District. Newly refreshed, this turnkey home features a spacious, renovated kitchen and upgraded bathrooms, highlighting a primary bath with a marble countertop, a soaking tub, and premium Italian Grohe fixtures. High-end finishes shine throughout, including new

    Michael Neeley William Raveis-New York LLC

    23 Briar Ct, Cross River, NY 10518
  • /16

    $1,875,000

    • 3 Beds
    • 2.5 Baths
    • 3,364 Sq Ft

    21 Twin Lakes Rd, South Salem, NY 10590

    Welcome to 21 Twin Lakes Road — a stunning, complete renovation that is as close to new construction as you'll find. Every detail has been thoughtfully reimagined, from the sun-filled open floor plan to the gorgeous authentic reclaimed beams that give the home instant character and warmth. A separate 1st floor bonus room and finished basement offers flexible space for a home office, playroom, or

    Juliska Martino Compass Greater NY, LLC

    21 Twin Lakes Rd, South Salem, NY 10590
  • /28

    $2,295,000

    $100K PRICE DROP
    • 3 Beds
    • 4.5 Baths
    • 2,812 Sq Ft

    137 Boway Rd, South Salem, NY 10590

    Gracious Country Colonial! Originally built in 1932 and thoughtfully renovated, this timeless antique Colonial seamlessly blends historic character with modern updates. Offering approximately 2,800 square feet of beautifully appointed living space, the home features hardwood floors, period millwork, abundant natural light, French doors, and nicely proportioned rooms throughout. Former owner Liz

    Cheryl Neuburger Ginnel Real Estate

    137 Boway Rd, South Salem, NY 10590
  • /50

    $2,750,000

    $500K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 5,575 Sq Ft

    127 Boutonville Rd, Pound Ridge, NY 10576

    Welcome to Brooke Hollow, a private and refined country estate set on over 8.7 acres along one of Pound Ridge’s most desirable roads. Tucked behind a gated entrance, the property unfolds into a quiet, beautifully composed landscape of rolling lawns, mature plantings, three serene ponds, and wooded walking paths that create a true sense of privacy and permanence.The grounds are

    Samuel Berek Serhant LLC

    127 Boutonville Rd, Pound Ridge, NY 10576
  • /27

    $1,595,000

    • 3 Beds
    • 3.5 Baths
    • 3,665 Sq Ft

    78 Old Church Ln, Pound Ridge, NY 10576

    Nestled on one of South Salem's most picturesque country lanes, 78 Old Church Lane offers a beautiful blend of privacy, comfort, and timeless style. Set on 4.6 magical, level acres surrounded by classic architecture and rolling countryside, this beautifully maintained residence is move-in-ready and designed for effortless living. Completely renovated in 2004, the home features sun-filled

    Jody Rosen Julia B Fee Sothebys Int. Rlty

    78 Old Church Ln, Pound Ridge, NY 10576
  • /22

    $809,900

    $90K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,189 Sq Ft

    98 Smith Ridge Rd, South Salem, NY 10590

    Beautifully updated and move-in ready, this 4-bedroom home is set on 2 private acres in the highly desirable Katonah-Lewisboro School District. Thoughtfully renovated throughout, the home features refinished hardwood floors, fresh neutral interiors, brand-new stainless steel appliances, 2 full bathrooms, and an updated powder room.The light-filled open layout offers comfortable everyday

    Sari Shaw Compass Greater NY, LLC

    98 Smith Ridge Rd, South Salem, NY 10590
  • /22

    $649,000

    $30K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,872 Sq Ft

    9 Stewart Rd, South Salem, NY 10590

    This lake community home has deeded access to Truesdale Lake and is located in the award-winning Katonah-Lewisboro School District. Located on a quiet cul-de-sac, this expanded cape cod-style home has good bones and great potential. Upon entering, a fireplace warms the front parlor and living room. Beyond, the kitchen opens to a dining room and an expanded family room with a stone fireplace, home

    Larry Mango Giner Real Estate Inc.

    9 Stewart Rd, South Salem, NY 10590
  • /45

    $1,695,000

    $54K PRICE DROP
    • 5 Beds
    • 6 Baths
    • 4,952 Sq Ft

    Unlisted Address

    Architecturally distinctive and beautifully connected to its natural surroundings, this custom cedar contemporary offers a refreshing alternative to the traditional colonial. Set on over 4 private acres in the heart of South Salem, the home blends dramatic volume, natural light, privacy, and flexible living spaces designed for modern living. The home’s layout flows easily from one inviting space

    Danielle Raguzin Re-Max Experience

    Unlisted Address
  • /14

    $1,150,000

    • 3 Beds
    • 2 Baths
    • 1,408 Sq Ft

    42 Gilbert St, South Salem, NY 10590

    A special opportunity to own a piece of Westchester's sought after private lake communities! Beautifully sited on 83 acre Lake Truesdale. It has a large deck and dock overlooking the water, along with a private driveway. This 1930 antique colonial is full of character - beamed ceilings, a fireplace and glass doors opening to a deck built for lakeside living. The spacious living room with

    Barbara Tremain Houlihan Lawrence Inc.

    42 Gilbert St, South Salem, NY 10590
  • /50

    $4,395,000

    $455K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 6,161 Sq Ft

    45 Pine Hill Dr, South Salem, NY 10590

    Welcome to 45 Pine Hill Drive, where modern luxury meets timeless sophistication. This fully renovated 4-bedroom, 4.5-bath residence has been transformed into a true showpiece, offering every amenity for elevated living. Inside, discover a breathtaking open-concept kitchen by Leicht (Germany) with premium electric stainless steel appliances, dual sinks, and a striking oversized island—perfect for

    Joseph Lukic Compass Greater NY, LLC

    45 Pine Hill Dr, South Salem, NY 10590
  • /2

    $583,700

    $174K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,100 Sq Ft

    1203 Old Post Rd, South Salem, NY 10590

    Looking for a great opportunity? Look no more! This property has tons of potential and is average in living space size for the neighborhood. It is located close to main roads with easy access to local amenities, such as shopping, banking, schools, and various eateries. Per our Appraisal describe the property as a SFR (colonial) built in 1980. It has a GLA of approx. 2100 and has 3 bedrooms and

    Christopher Rose REALHome Services & Solutions

    1203 Old Post Rd, South Salem, NY 10590
  • /7

    $2,250,000

    • 4 Beds
    • 3.5 Baths
    • 3,000 Sq Ft

    Lot 6 Sachem Way, South Salem, NY 10590

    A rare opportunity to own a Silvermine Preserve home where sophisticated design, exceptional craftsmanship and thoughtful technology come together. Engineered as a high-performance home, it incorporates geothermal heating and cooling along with advanced energy-efficient building systems that enhance year-round comfort, efficiency, and long-term value. Set within an exclusive enclave of

    Michael Neeley William Raveis-New York LLC

    Lot 6 Sachem Way, South Salem, NY 10590
  • /44

    $995,000

    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    139 Smith Ridge Rd, South Salem, NY 10590

    Set back approximately 600 feet from the road, this serene South Salem retreat offers a rare combination of privacy, tranquility, and convenience. Nestled on 9.47 acres, you are welcomed by beautiful flowering fruit trees and manicured landscaping. The 3-bedroom, 2.5-bath residence offers approximately 2,600 square feet of thoughtfully designed living space surrounded by natural

    Sally Walter Compass Greater NY, LLC

    139 Smith Ridge Rd, South Salem, NY 10590
  • /41

    $759,000

    • 3 Beds
    • 2.5 Baths
    • 1,672 Sq Ft

    15 Cross River Rd, Cross River, NY 10518

    Wide plank floors, an original fireplace, and a wide center staircase set the tone in this two-story 1845 Colonial, offering the kind of historic character that’s increasingly hard to find. Built in 1845 and tucked beside Ward Pound Ridge Reservation with views of Cross River Reservoir, this antique home retains its original charm while presenting a rare opportunity for restoration in a truly

    Spencer Matthews Houlihan Lawrence Inc.

    15 Cross River Rd, Cross River, NY 10518
  • /26

    $1,495,000

    • 3 Beds
    • 4 Baths
    • 3,720 Sq Ft

    257 Kitchawan Rd, South Salem, NY 10590

    Stunning post-modern contemporary w/ cathedral ceilings, private professionally landscaped back yard with mature plantings. Featuring a large deck, in-ground free form gunite pool with screened-in gazebo, fully fenced backyard with separately fenced dog-run. Large living room with a fieldstone wall, majestic raised hearth fireplace and hobnailed wood floor. Formal dining room w/ bluestone floor,

    RHONA BORK RMB & Associates

    257 Kitchawan Rd, South Salem, NY 10590
  • /38

    $1,495,000

    Open Sat 11AM - 1PM $195K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,326 Sq Ft

    2 Tommys Ln, South Salem, NY 10590

    Step inside Tommy’s Lane, where understated architecture gives way to unforgettable design. From the curb, this timeless transitional Colonial sits quietly on just shy of two flat, sun-drenched private acres with a pool. Open the dramatic custom black glass front doors, however, and the entire experience changes. A dramatic two-story foyer introduces interiors that feel as though Restoration

    Melissa Marcogliese Compass Greater NY, LLC

    2 Tommys Ln, South Salem, NY 10590
  • /8

    $2,750,000

    • 4 Beds
    • 3.5 Baths
    • 5,600 Sq Ft

    Lot 13 Sachem Way, South Salem, NY 10590

    A rare opportunity to own a custom-designed home in Silvermine Preserve, an exclusive enclave of architecturally distinctive residences in South Salem. Set on 1.33 private acres at the entrance to Sachem Way, this exceptional residence was envisioned by the builder in collaboration with acclaimed architect Teo Siguenza, inspired by the enduring character of the farmhouse and reimagined through a

    Michael Neeley William Raveis-New York LLC

    Lot 13 Sachem Way, South Salem, NY 10590
  • /24

    $545,000

    $30K PRICE DROP
    • 1 Bed
    • 1.5 Baths
    • 1,451 Sq Ft

    157 Jay Ct, Cross River, NY 10518

    Welcome to this beautifully maintained townhouse in the highly desirable Meadows community. Ideally located near shopping, restaurants, and schools, this home offers affordable living, excellent amenities, and low taxes within the sought-after Katonah-Lewisboro School District. Situated in one of the most private locations in the development, the home is just a short walk to the community pool

    Judith Collins-Turi William Raveis-New York LLC

    157 Jay Ct, Cross River, NY 10518
  • /24

    $975,000

    • 4 Beds
    • 3 Baths
    • 2,490 Sq Ft

    1 Sabbath Day Hill Rd, South Salem, NY 10590

    Nestled on a picturesque road in the heart of South Salem, this beautifully maintained 4-bedroom, 3-full-bath home offers the perfect balance of privacy, comfort, and convenience. Lovingly cared for by only its second owner, this exceptional home has been thoughtfully updated over the years while maintaining its warmth and charm. Set amid mature woodlands, the hilltop retreat offers a peaceful

    Karen Susan Savir Coldwell Banker Realty

    1 Sabbath Day Hill Rd, South Salem, NY 10590
  • /33

    $1,275,000

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,436 Sq Ft

    119 Mustato Rd, Katonah, NY 10536

    Katonah: Nestled on 2.1 private acres and directly abutting the 200 acre renowned Beaver Dam Sanctuary with access to the BRLA riding lanes, hiking trails and open spaces this pristine residence offers an exceptional blend of natural beauty, privacy and refined living. Surrounded by mature trees, rolling lawns and protected conservation land, the property enjoys a serene setting with breathtaking

    Rita Carrozza Houlihan Lawrence Inc.

    119 Mustato Rd, Katonah, NY 10536
  • /49

    $1,350,000

    • 4 Beds
    • 2.5 Baths
    • 2,918 Sq Ft

    50 Sabbath Day Hill Rd, South Salem, NY 10590

    Welcome to 50 Sabbath Day Hill Road, a warm and inviting Colonial with contemporary flair, beautifully set on more than two private acres in desirable South Salem. Thoughtfully updated inside and out, this home offers a wonderful combination of timeless character, modern finishes and comfortable everyday living.The updated exterior creates an impressive first impression and introduces a home

    Rebecca Yaun Houlihan Lawrence Inc.

    50 Sabbath Day Hill Rd, South Salem, NY 10590
  • /30

    $2,595,000

    • 4 Beds
    • 4 Baths
    • 4,182 Sq Ft

    380 Cross River Rd, Katonah, NY 10536

    INDOOR POOL! Primary on the main level. Set behind gates on more than 13 acres, with an indoor pool, this subdividable, thoughtfully renovated country property offers a rare combination of privacy, space, and convenience just minutes from the heart of Katonah. With over 4,000 square feet of updated living space, the home features a welcoming layout designed for comfortable everyday living and

    Michael Neeley William Raveis-New York LLC

    380 Cross River Rd, Katonah, NY 10536
  • /7

    $1,500,000

    • Land
    • 4.3 Acres
    • $348,837 per Acre

    0 Church Tavern Rd Unit KEY995093, South Salem, NY 10590

    Rare opportunity to build a custom estate on an exceptional property with sweeping, long-range, breathtaking sunset views. This remarkable parcel offers a stunning setting to create a home tailored to your vision. Utility services are already in place, and the Board of Health has approved the 4.3-acre parcel for a five-bedroom residence. A truly special offering with endless possibilities.

    Susan Stillman Houlihan Lawrence Inc.

    0 Church Tavern Rd Unit KEY995093, South Salem, NY 10590
  • /25

    $775,000

    • 3 Beds
    • 2 Baths
    • 1,754 Sq Ft

    3 Bouton St, South Salem, NY 10590

    Move right into the lake lifestyle! Completely renovated and thoughtfully designed, this turn-key, contemporary ranch offers the perfect blend of modern comfort and easy one-level living.Nestled in the sought-after Truesdale Lake area of South Salem, this sun-drenched three-bedroom, two-full-bath home is just a short stroll to the lake and beach. An inviting open floor plan creates an

    Mark Boyland Keller Williams Realty Partner

    3 Bouton St, South Salem, NY 10590
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