Lewisboro, NY Homes for Sale with Acreage

HIDEOUT HILL. Part of South Salem’s rich history. Circa 1740 Antique Colonial and one of the area’s oldest homes. Brimming with period details including wide board floors, two fireplaces and period moldings. Tastefully renovated in 2020 carefully marrying the old with the new. 3200 square feet of living space with beautifully proportioned rooms rich in detailing. Exceptionally appointed interior

Lisa Fitz Ginnel Real Estate

From the moment you turn down the long, secluded driveway toward 1 Sabbath Day Hill Rd, the feeling is unmistakable: this is a retreat built for those who prize privacy, elevation, and quiet grandeur. Perched atop its own hill and surrounded by mature trees, the home sits back from the road with views visible from the wide front porch—a space that feels like your own private veranda overlooking

Alex Mashkin Keller Williams Realty Partner

Nestled in a desirable South Salem lakefront enclave, this masterfully renovated Craftsman-style residence represents a rare opportunity for the discerning buyer. Spanning 1,852 square feet, the three-bedroom, two-and-a-half-bath home has been thoroughly reimagined, artfully balancing timeless charm with upscale refinement.The heart of the home is a chef-caliber kitchen equipped with stone

Anthony Ardino William Raveis Real Estate

Welcome to South Salem! Nestled on a picturesque 1.09 acre, this inviting split-level home offers the perfect combination of privacy, and everyday convenience on a spacious private lot.The main level features a bright and open design with a modern eat-in kitchen, dining area, and a living room anchored by a fireplace — creating the ideal setting for both quiet evenings and effortless

Carine Nowak Compass Greater NY, LLC

Nestled on a private, picturesque 1-acre property, this move-in-ready home offers the perfect blend of comfort, convenience, and natural beauty. Freshly painted throughout, the home features newly refinished hardwood floors that shine with warmth and character. The spacious interior boasts two fireplaces, creating inviting gathering spaces for every season, while a beautiful bay window fills the

Maria Tomaselli Howard Hanna Rand Realty

Welcome to 5 Diane Court, a thoughtfully updated Colonial nestled on a quiet cul-de-sac with views and access to a private, tranquil lake. This 6-bedroom, 3 full bath home provides an exceptional lifestyle both inside and out. The heart of the home is the updated kitchen, featuring a Sub-Zero refrigerator, a Viking 6-burner stove, and sliding doors that open directly to a deck. The main level

Patricia Hinkley Coldwell Banker Realty

Nestled on a serene, tree-lined cul-de-sac in a wonderful neighborhood setting, this light-filled 4-bedroom, 2.1-bath Contemporary home is privately set on 2 beautiful acres within the award-winning Katonah-Lewisboro School District. Offering the perfect balance of tranquility and convenience, this move-in ready home features an open-concept layout designed for comfortable everyday living.

Cindy Glynn Compass Greater NY, LLC

This home truly stands apart. A turnkey five-bedroom Colonial set on nearly three private acres, privately located at the end of a quiet cul-de-sac. Thoughtfully expanded from its original design, the home features an exceptional layout with remarkable versatility, perfect for entertaining, working from home, play areas, all designed to meet your lifestyle. At the heart of the home is a custom,

Melissa Frank Lutz Douglas Elliman Real Estate

Welcome to 31 Spring Street South in beautiful South Salem, NY — a lovingly maintained expanded ranch being offered for the first time in decades. Nestled on a private, sun-drenched property with mature landscaping and estate-like grounds, this special residence offers the perfect blend of tranquility, space, and opportunity. Featuring 4 bedrooms/2 full bathrooms, this picturesque property also

Kathryn Norman Market Match Real Estate Corp

Welcome to 158 Mead Street — offered for the first time, this custom-designed sanctuary is nestled in the heart of Waccabuc and lives like four bedrooms (4 bedroom septic). Privately sited on over four park-like acres, this elegant residence is surrounded by mature trees, creating a serene retreat just minutes from town, train, and everyday conveniences. Inside, the home seamlessly blends rustic

Amy Smith Sroka Julia B Fee Sothebys Int. Rlty

Welcome to Pepper Ridge Farm! Rarely does an opportunity like this come along. Tucked away on nearly 5 private acres, this classic Mid-Century ranch offers the chance to create exactly the lifestyle you've been imagining. Whether you're looking for a manageable country retreat, a renovation project with room to grow, or the ideal setting for a custom estate home, this property delivers the

Debi Orr Keller Williams Prestige Prop

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

Elegant Retreat tucked in the heart of South Salem nestled on nearly 3 acres of scenic countryside. This beautifully maintained center hall Colonial offers the perfect blend of space, comfort, and modern convenience. Classic style with all 4 generous bedrooms on the second level, this home boasts a recently updated country kitchen & all new hardwood floors throughout. Dual fireplace with vaulted

Giancarlo Pecora eXp Realty

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

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.

Perfect as a year-round residence or a private weekend retreat, this charming home offers comfortable living in a super convenient location. It sits on a quiet country road surrounded by nature, yet it is close to the highway (7 miles to I-684); train (8 miles to Katonah MTA Metro North station with direct trains to Grand Central), schools, and other everyday conveniences. This well-loved home

Natasha Pazdzerskaia Coldwell Banker Realty

This move-in-ready colonial offers a functional layout for everyday living and entertaining in a serene setting. Hardwood floors throughout, brand-new HVAC, updated kitchen, and bath. Bay windows provide leafy views of the woodsy property, pond, and old stone walls. A large family room with a cozy fireplace has sliders to enjoy outdoor living on a large deck. Upstairs are four quiet bedrooms. The

Larry Mango Giner Real Estate Inc.

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

A rare, design-forward opportunity to build a modern, mid-century inspired residence in a thoughtfully planned enclave of similar new construction homes. Set on a beautiful one-acre lot along a private gated road in peaceful South Salem, this single-level design emphasizes clean lines, natural light, and seamless indoor-outdoor living. Walls of glass and an open layout bring the surrounding

Michael Neeley William Raveis-New York LLC

STEP INTO THE PAST. Part of South Salem’s rich history. Charming Antique Farmhouse, circa 1775, once a general store and post office. Rocking Chair Porch. Original Front Parlor. Country Kitchen. Warm and inviting Living Room with vaulted ceiling and doors to rear deck. Two Bedrooms and Two Baths. Separate Barn with garage bay and second floor heated Studio with vaulted ceiling. Picture book

Mary Anne Condon Ginnel Real Estate

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

Nikki McMann William Raveis-New York LLC

Welcome to 3 Old Shop Road, a beautifully updated farmhouse that perfectly captures the essence of relaxed country living in a highly coveted Cross River address. Set on a picturesque, park-like parcel with sweeping lawns and mature trees, this five-bedroom, five-bath residence offers a seamless blend of historic character, modern comfort, and premium amenities. Designed for both effortless

Jody Rosen Julia B Fee Sothebys Int. Rlty

RIVERBEND FARM. Remarkable frontage on the rushing Waccabuc River. The original Adams Dairy Farm--an absolutely breathtaking property with level lawns lined by old stone walls, specimen trees and vibrant flowering perennials. Incredible gardens of Daffodils, Tulips, Iris, wild Roses, Lilac, Wysteria, Allium, and Peonies along with fragrant and flowering Magnolia, Apple, and Viburnum. Raised bed,

Jennie Doukas Ginnel Real Estate

Nestled on a private cul-de-sac in the heart of Katonah, this beautifully updated Contemporary Colonial offers the perfect blend of space, natural light, and tranquility. Set on over an acre of park-like property, the home enjoys a serene setting surrounded by mature trees, expansive lawns, and picturesque views. Featuring four bedrooms, two-and-a-half baths, and over 2,500 square feet of living

Cord Stahl Julia B Fee Sothebys Int. Rlty

Welcome to 15 Flat Rock Drive; an irresistible opportunity to live on a highly sought after **cul-de-sac street** just moments from Ridgefield's vibrant village center. This prime location delivers the best of both worlds: a peaceful neighborhood setting paired with unbeatable convenience close to town, the NY border, and top NYC commuting options. Inside, the home shines with a bright, flowing

Michele Isenberg Coldwell Banker Realty

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 thoughtfully

Samuel Berek Serhant LLC

First time on the market from the original owner, 80 Hack Green Road is privately set on almost three impeccably landscaped and flat acres between Scotts Corner and New Canaan. This distinguished brick and stucco colonial Tudor offers approximately 4,000 square feet of exceptional craftsmanship and timeless architectural character. Built by a professional contractor well beyond standard

Natalia Wixom Compass Greater NY, LLC

Location is everything-and this one delivers. Nestled on a quiet cul-de-sac in the sought-after West Lane section of Ridgefield, this property offers the ultimate combination of privacy, neighborhood charm, and unmatched convenience. Just 15 minutes to the Katonah Metro-North line, one hour to NYC by car, minutes to downtown New Canaan, Ridgefield & nearby NY/CT state parks, this is one of the

Kyle Neumann Houlihan Lawrence