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Lewisboro, NY Homes for Sale with Acreage

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  • /30

    $1,365,000

    • 4 Beds
    • 4.5 Baths
    • 4,078 Sq Ft

    1 Canaan Cir, South Salem, NY 10590

    Elegantly updated Modern Colonial with majestic curb appeal on a quiet country cul-de-sac. Ten minutes to Wilton/New Canaan (Connecticut) train stations. Picture perfect corner lot in gorgeous Northern Westchester, A grand foyer with double height ceilings ushers you into generously sized rooms with three cozy wood burning fireplaces. Eight French doors from three welcoming rooms open out onto a

    Juergen Hess Five Corners Properties Inc

    1 Canaan Cir, South Salem, NY 10590
  • /50

    $5,450,000

    • 4 Beds
    • 3.5 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, 3.5-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
  • /9

    $750,000

    • Land
    • 9.09 Acres
    • $82,508 per Acre

    6 Duffys Bridge Rd, Lewisboro, NY 10536

    A rare find at a great price. Ready to go! Unique parcel of amazing privacy on over 9 acres of improved land in desirable Katonah location. Drilled 330' well with 50 gpm and septic installed for four bedroom home. This wooded hilltop homesite is approved for a single-family home by the Town of Lewisboro. Land is cleared, graded and has Belgian block-lined gravel driveway and stone

    Nancy Tuccillo Coldwell Banker Realty

    6 Duffys Bridge Rd, Lewisboro, NY 10536
  • /36

    $2,950,000

    • 6 Beds
    • 5.5 Baths
    • 6,344 Sq Ft

    133 Boway Rd, South Salem, NY 10590

    The Quintessential Getaway. Long, gated drive through spectacular grounds to ultimate privacy and seclusion. Twenty glorious acres with level lawns, ancient trees, ornamental shrubs and flowering perennials. Fenced grounds with woodland walking trails throughout. Absolutely breathtaking backdrop for the perfect country lifestyle. Fabulous raised terrace overlooking the stunning swimming pool.

    Mary Anne Condon Ginnel Real Estate

    133 Boway Rd, South Salem, NY 10590
  • /39

    $1,280,000

    • 4 Beds
    • 3 Baths
    • 2,447 Sq Ft

    46 Ridgefield Ave, South Salem, NY 10590

    Exquisitely renovated, this 4-bedroom, 3-bath residence showcases a timeless elegance with every detail thoughtfully reimagined. The first-floor primary suite offers the ease of single-level living, while the chef’s kitchen—complete with a peninsula and bar seating—serves as a stylish gathering place. Graceful living and dining rooms, each with its own fireplace and enhanced by soaring ceilings,

    Monica Webster Douglas Elliman Real Estate

    46 Ridgefield Ave, South Salem, NY 10590
  • /34

    $1,295,000

    • 2 Beds
    • 3 Baths
    • 1,955 Sq Ft

    39 Knapp Rd, South Salem, NY 10590

    Magical lakefront retreat! Spectacular well maintained contemporary home located on Lake Oscaleta with 146 feet of direct lake access. Bright three level VIEW home. Soaring ceilings, skylights, floor to ceiling windows, wood-burning fireplace, and private setting. Wrap around view deck. Flexible floor plan. Main floor with kitchen, spacious living room/dining area, den, bedroom, and full bath.

    Paul Tollefson William Raveis-New York LLC

    39 Knapp Rd, South Salem, NY 10590
  • /31

    $779,000

    • 4 Beds
    • 2.5 Baths
    • 2,921 Sq Ft

    212 Elmwood Rd, South Salem, NY 10590

    Tucked away on a quiet, wooded lane, this contemporary retreat is all about the setting - private, peaceful, and naturally dramatic. Set against a backdrop of exposed rock formations and mature trees, the backyard is a true sanctuary. Whether you're entertaining on the expansive deck, relaxing in the in-ground pool and jacuzzi, or enjoying a quiet morning coffee surrounded by nature, this outdoor

    Igor Krasnoperov Rising Star Realty

    212 Elmwood Rd, South Salem, NY 10590
  • /42

    $2,700,000

    • 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

    Nikki McMann William Raveis-New York LLC

    11 Lost Nations Rd, Pound Ridge, NY 10576
  • /16

    $735,000

    • 3 Beds
    • 1.5 Baths
    • 2,085 Sq Ft

    247 Smith Ridge Rd, South Salem, NY 10590

    Discover this charming South Salem farmhouse nestled on two beautiful acres. It features three bedrooms and an open concept chefs kitchen. Enjoy cozy times in front of the fireplace in this warm and inviting ambience. The property offers the perfect blend of country living and modern comfort. With two first floor bedrooms and an open floor plan this home provides ample space for family gatherings

    Cyndi David William Raveis-New York, LLC

    247 Smith Ridge Rd, South Salem, NY 10590
  • /50

    $1,100,000

    • 5 Beds
    • 4.5 Baths
    • 3,648 Sq Ft

    1196 Route 35, South Salem, NY 10590

    A Timeless Retreat with Modern Luxury in LewisboroTucked away on 5.33 private acres, this extraordinary Cape Cod-Split Ranch is a seamless fusion of classic elegance and modern sophistication. Thoughtfully redesigned and fully upgraded in the past five years, this 5-bedroom, 4.5-bathroom estate spans 3,648 sq. ft., offering an unparalleled living experience. With five-zone heating and

    Zulleyma Alvarez Compass Greater NY, LLC

    1196 Route 35, South Salem, NY 10590
  • /40

    $7,000,000

    • 6 Beds
    • 7 Baths
    • 7,541 Sq Ft

    384 West Ln, Ridgefield, CT 06877

    Welcome to 384 West Lane, an exceptional Estate Property that defines timeless Connecticut luxury across 13 exquisite, park-like acres- straddling Westchester County & just an hour from NYC. At its heart stands a classic Georgian Manor-7,500 SqFt of architectural mastery where perfectly scaled rooms, soaring ceilings, and refined millwork create an atmosphere of enduring elegance. Designed by the

    Karla Murtaugh Compass Connecticut, LLC

    384 West Ln, Ridgefield, CT 06877
  • /33

    $1,374,000

    • 5 Beds
    • 3.5 Baths
    • 3,938 Sq Ft

    381 W Mountain Rd, Ridgefield, CT 06877

    Perched atop a hill in the sought after West Mountain neighborhood of Ridgefield, this 1898 farmhouse tells a story that's been shaped, expanded, and perfected over time. What began as the original farmhouse on the hill now blends antique character with the ease of modern living, set on 3.21 private acres and bordered by 12 acres of protected land to the east. Inside, 5 bedrooms and 3.5 baths

    Ryan Kundrat Keller Williams Prestige Prop

    381 W Mountain Rd, Ridgefield, CT 06877
  • /39

    $3,250,000

    • 4 Beds
    • 4.5 Baths
    • 5,575 Sq Ft

    127 Boutonville Rd, Pound Ridge, NY 10576

    Sophisticated & Serene. The perfect country retreat. Over eight, peaceful acres along a desirable country road. Gated drive to private oasis with gorgeous plantings, three ponds, rolling lawns and woodland walking paths. Infinity edge salt-water swimming pool with spa and your own tennis court. Meticulous stone and shingle Country House with 5500 square feet of sun-filled living space. Fabulous

    Mary Anne Condon Ginnel Real Estate

    127 Boutonville Rd, Pound Ridge, NY 10576
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