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Lewisboro, NY Homes for Rent

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  • /42

    $20,000 Per Month

    • 6 Beds
    • 7.5 Baths
    • 8,900 Sq Ft
    • House for Rent

    11 Lost Nations Rd, Pound Ridge, NY 10576

    Offered for rent or for sale. 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

    Agent Photo

    Nikki McMann

    William Raveis-New York LLC

    11 Lost Nations Rd, Pound Ridge, NY 10576
  • /23

    $5,900 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,896 Sq Ft
    • House for Rent

    1 Branch St, Goldens Bridge, NY 10526

    Enjoy a perfect weekend escape or year-round lake living! This 3-bedroom contemporary, artist-owned cottage is nestled in the heart of Goldens Bridge Colony, surrounded by 17 acres with lake rights, swimming, clubhouse, summer camp, hiking trails, and so much more. This home offers a perfect blend of modern design with a tranquil cabin charm. Features include: high-pitched ceilings, working

    Peter Giner Giner Real Estate Inc.

    1 Branch St, Goldens Bridge, NY 10526
  • /20

    $6,950

    Total Monthly Price

    • 4 Beds
    • 3 Baths
    • 1,558 Sq Ft
    • House for Rent

    38 Bishop Park Rd, Pound Ridge, NY 10576

    ***1/2 Month Broker Fee***Magical park-like setting on crystal-clear Lake Kitchawan! This beautifully expanded ranch offers an exceptionally rare opportunity to enjoy private lakefront living in a tranquil, resort-like setting on a quiet country lane, while remaining easily commutable to New York City. The thoughtfully designed floor plan features a gorgeous kitchen, three bedrooms, and

    38 Bishop Park Rd, Pound Ridge, NY 10576
  • /33

    $15,000 Per Month

    • 4 Beds
    • 3 Baths
    • 3,476 Sq Ft
    • House for Rent

    50 Cove Rd, South Salem, NY 10590

    Enjoy this beautifully furnished 4+ Bedroom home on Lake Waccabuc just in time for the fall foliage. Nestled on one of Northern Westchester’s most sought-after lakes, this inviting retreat offers the perfect blend of comfort, relaxation, and breathtaking waterfront views.Wake up to lake views throughout the home and spend your days swimming, kayaking, paddle boarding, fishing, or simply

    Gina Cooney Giner Real Estate Inc.

    50 Cove Rd, South Salem, NY 10590
  • /8

    $2,495

    Total Monthly Price

    • Studio
    • 1 Bath
    • 550 Sq Ft
    • House for Rent

    23 Spring St S, South Salem, NY 10590

    1 MONTH BROKER FEE, NO STOVE, COOKTOP, HALF FRIDGE, SMALL DOGS/NO CATS, 1 PERSON ONLYOpen-concept alcove studio cottage for rent in a private and peaceful setting, completely updated with new appliances and modern finishes. This charming studio rental offers total privacy, a dedicated driveway and private parking area, while the owner resides on-site in a separate residence.

    23 Spring St S, South Salem, NY 10590
  • /26

    $9,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • House for Rent

    24 Cove Rd, South Salem, NY 10590

    Come and enjoy Lake views all year round. With fall and winter coming what better way to wake up with a view of Lake Waccabuc and a cozy fire. This newly renovated home on Lake Waccabuc is just steps to your private dock and beautiful lake community on Cove Rd. This home lends itself to water views throughout the house. Cozy open floor plan downstairs with beautiful kitchen and fireplace. 1st

    Gina Cooney Giner Real Estate Inc.

    24 Cove Rd, South Salem, NY 10590
  • /10

    $2,300 Per Month

    • 1 Bed
    • 1 Bath
    • 450 Sq Ft
    • Apartment for Rent

    18 Hall Ave, Goldens Bridge, NY 10526

    Welcome to The Colony at Goldens Bridge, a charming lake community offering a unique lifestyle in a picturesque setting. This bright and private 1-bedroom apartment features its own separate entrance, full bathroom, one assigned parking space, and access to a flat, tree-lined yard perfect for relaxing outdoors. Heat and water are included in the rent, providing added value and

    Teresa Chang Houlihan Lawrence Inc.

    18 Hall Ave, Goldens Bridge, NY 10526
  • /35

    $5,500 Per Month

    • 3 Beds
    • 1 Bath
    • 1,300 Sq Ft
    • House for Rent

    9 S Shore Dr, South Salem, NY 10590

    Booked May 19, 2026 - October 20, 2026Lakeside Retreat - where you can get away from it all! Relax with the family at this peaceful fully furnished home. This is a 3 Bedroom that features a newly renovated open floor plan of kitchen, den, fireplace and living room with lake views and a beautiful back deck overlooking Lake Waccabuc. Enjoy the water views from your private dock on the lake.

    Gina Cooney Giner Real Estate Inc.

    9 S Shore Dr, South Salem, NY 10590
  • /36

    $4,900 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,101 Sq Ft
    • House for Rent

    53 Cove Rd, South Salem, NY 10590

    Enjoy Waccabuc Lake! Escape to an exceptional year-round retreat in this beautifully renovated 2-bedroom cottage, where timeless charm meets modern comfort in one of Westchester’s most desirable lake communities on Lake Waccabuc. Thoughtfully redesigned this enchanting home offers the perfect balance of relaxation, recreation, and refined country living.At the heart of the home a warm and

    Gina Cooney Giner Real Estate Inc.

    53 Cove Rd, South Salem, NY 10590
  • /50

    $10,999 Per Month

    • 4 Beds
    • 3.5 Baths
    • 4,649 Sq Ft
    • House for Rent

    27 Gideon Reynolds Rd, Cross River, NY 10518

    Discover this elegant 4-bedroom, 3.5-bath retreat nestled in the coveted Cross River, NY community. Rich hardwood floors flow throughout the main level, setting a warm and sophisticated tone from the moment you walk in. A classic wood-burning fireplace anchors the living area, creating an inviting space to gather year-round. Upstairs and in the lower level, plush carpet adds comfort underfoot in

    Frank Norwood DC & SF Inc

    27 Gideon Reynolds Rd, Cross River, NY 10518
  • /13

    $6,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,350 Sq Ft
    • House for Rent

    57 Truesdale Lake Dr, South Salem, NY 10590

    Beautifully sited on lovely Lake Truesdale! Charming and very private! It features 3 bedrooms, 2 baths, an open living room, dining room area and beautifully appointed kitchen with a wall of windows leading to the new deck which spans the length of the house. There are doors out from the basement to the patio which has a path that leads down to the lake for your morning swim. From gorgeous

    Barbara Tremain Houlihan Lawrence Inc.

    57 Truesdale Lake Dr, South Salem, NY 10590
  • /26

    $15,000 Per Month

    • 5 Beds
    • 4.5 Baths
    • 4,530 Sq Ft
    • House for Rent

    22 Waccabuc River Ln, South Salem, NY 10590

    Sited with a commanding presence on eight plus acres of open meadows and views of lush woodlands this distinctive sophisticated residence offers the perfect tranquil environment. The recently completed renovation highlights the open flow and light filled rooms. Imbued with warmth, two fireplaces, oversized windows and high quality finishes reflecting the epitome of ease and comfort. Easy flow to

    Susan Stillman Houlihan Lawrence Inc.

    22 Waccabuc River Ln, South Salem, NY 10590
  • /25

    $3,200 Per Month

    • 1 Bed
    • 1.5 Baths
    • 1,451 Sq Ft
    • Townhouse for Rent

    46 Winterberry Cir, Cross River, NY 10518

    Rare opportunity to rent a spacious townhouse in The Meadows at Cross River. Tucked away in a quiet location within this desirable community, this 1-bedroom, 1.5 bathroom home offers comfortable living, abundant storage, and is just a short walk to the community pool, fitness room, and tennis courts.The main level features a bright, eat-in kitchen with new appliances, an open living room and

    Mark Boyland Keller Williams Realty Partner

    46 Winterberry Cir, Cross River, NY 10518
  • /28

    $5,900 Per Month

    • 2 Beds
    • 3 Baths
    • 2,100 Sq Ft
    • House for Rent

    5 Shore Trail, South Salem, NY 10590

    Perfectly set on nearly an acre of beautifully landscaped grounds, this fully furnished retreat offers exceptional privacy. A chic paradise, the home features soaring cathedral ceilings, exposed beams, chef's kitchen, dining room, hardwood floors, two fireplaces, water views, and thoughtfully designed living spaces that seamlessly blend comfort and sophistication. A generator provides peace of

    Karen Ferris Houlihan Lawrence Inc.

    5 Shore Trail, South Salem, NY 10590
  • /39

    $6,250 Per Month

    • 3 Beds
    • 3.5 Baths
    • 3,640 Sq Ft
    • House for Rent

    161 Goldens Bridge Rd, Katonah, NY 10536

    New York City Tribeca loft meets serene suburban living in this uniquely designed contemporary home, set in the desirable Katonah Ridge community sitting on over 2.4 acres! Perfectly situated just minutes from downtown Katonah, with easy access to the Metro North with a short hour commute to NYC. Privately set back from the road with a long driveway and plenty of space for multiple vehicles, this

    Michael Clemente DeSimone Real Estate

    161 Goldens Bridge Rd, Katonah, NY 10536

Why Live in Lewisboro

Lewisboro, New York, located 57 miles from New York City, is a town known for its natural beauty and highly rated schools. The Katonah-Lewisboro School District serves the area, with Increase Miller Elementary, Meadow Pond Elementary, John Jay Middle, and John Jay High all receiving high ratings. The town features several parks and preserves, including Lewisboro Town Park, which offers walking trails, a playground, and sports courts, and Onatru Farm Town Park, known for its hiking trails and sports fields. The Ward Pound Ridge Reservation spans over 4,300 acres and includes hiking trails, campsites, and a nature museum, while the Wolf Conservation Center in South Salem focuses on wolf preservation and education. Housing in Lewisboro consists of single-family homes and townhouses, often set among dense forests of oak, maple, and ash trees. Colonial Revival and farmhouse styles are common, with some homes over 100 years old. Commuters can access New York City via the Saw Mill River Parkway or the Metro-North Railroad from Goldens Bridge station. Local amenities include Gossett’s Farmers Market in South Salem, the Orchard Square at Cross River shopping center, and various dining and shopping options in nearby Ridgefield, Connecticut. Community events and programs are hosted by the Lewisboro Library, and the town also celebrates the annual Lewisboro Library Fair and Holidays on the Hill Train Show at Lasdon Park & Arboretum.

Frequently Asked Questions

What neighborhoods in Lewisboro, NY are best for renting a home?
The best neighborhood for renting in Lewisboro, NY depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a home include North Stamford, Cranbury, West Norwalk and Springdale, each with its own character and price range.
How to Rent a Home