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Lewisboro, NY Homes for Sale with Garage

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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
  • /47

    $950,000

    • 3 Beds
    • 2.5 Baths
    • 2,650 Sq Ft

    14 Mark Mead Rd, Cross River, NY 10518

    Welcome to 14 Mark Mead Road — a picture-perfect Cape Cod Colonial tucked on a quiet cul-de-sac in desirable Cross River. This beautifully maintained home blends timeless style with thoughtful modern updates, offering a warm, comfortable atmosphere and exceptional attention to detail. The sunlit main level flows effortlessly from the great room with a wood-burning fireplace to the granite eat-in

    Christopher Motta Real Broker NY LLC

    14 Mark Mead Rd, Cross River, NY 10518
  • /21

    $389,000

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft

    50 S Shore Dr, South Salem, NY 10590

    Charming lake-area cottage offering an inviting retreat in the heart of South Salem. It lives like a two-bedroom, with two bonus rooms that can serve as an office, guest space, or creative studio. Enjoy lake rights with access to a private dock—perfect for relaxing, kayaking, or soaking in the serene water views. The property includes a carport and a driveway accommodating two to three cars,

    Mark Boyland Keller Williams Realty Partner

    50 S Shore Dr, South Salem, NY 10590
  • /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
  • /2

    $667,300

    • 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
  • /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

    $1,750,000

    • 2 Beds
    • 3.5 Baths
    • 3,778 Sq Ft

    33 Truesdale Lake Dr, South Salem, NY 10590

    Welcome to a unique sanctuary that marries expert design with masterful craftsmanship in every detail. This lakefront home greets you with a welcoming lodge-style entry, leading to an open and flexible floor plan that epitomizes resort-style living. Architectural highlights include exposed structural wood beams, vaulted ceilings, walls of windows, French doors, reclaimed dark wood flooring, and

    Jonathan Gineo Jonathan D. Gineo

    33 Truesdale Lake Dr, 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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