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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
  • /20

    $5,185 Per Month

    • 3 Beds
    • 3 Baths
    • 2,433 Sq Ft
    • Townhouse for Rent

    1 The Meadows, Cross River, NY 10518

    Property Id: 492831 Townhouse 3BR / 2.5 bath 2433 sq ft Recently Renovated w finished basement - Pets are welcome! Townhouse / condo in "The Meadows" Katonah - Lewisboro schools Increase Miller elementary John Jay MS John Jay HS New wide plank HW oak flooring throughout New "soft close" cabinets in kitchen w quartz countertops w subway tile

    1 The Meadows, Cross River, NY 10518
  • /23

    $6,500 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
  • /18

    $3,150 Per Month

    • 1 Bed
    • 1 Bath
    • 1,112 Sq Ft
    • Condo for Rent

    62 Fox Run Unit 262, South Salem, NY 10590

    Welcome to Oakridge Condominiums. This sophisticated condo offers a spacious living room with a fireplace, built-ins, and a high ceiling; an updated kitchen with granite counters and a dining area; a large bedroom; and a full bathroom on the main level. There is a spiral staircase to an open loft on the upper level that can serve as an office or guest room. Some special features include high-tech

    Lucille Ettere Houlihan Lawrence Inc.

    62 Fox Run Unit 262, South Salem, NY 10590
  • /33

    $28,000 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, available just in time for summer! 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
  • /26

    $18,000 Per Month

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

    24 Cove Rd, South Salem, NY 10590

    Summer is coming! And what better place to spend it than at Waccabuc Lake. Enjoy this newly renovated home on Lake Waccabuc. 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 floor also offers a full bathroom. Side deck with lake view off of

    Gina Cooney Giner Real Estate Inc.

    24 Cove Rd, South Salem, NY 10590
  • /40

    $15,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,866 Sq Ft
    • House for Rent

    34 Twin Lakes Rd, South Salem, NY 10590

    Fully Furnished Seasonal Rental available Sept 1-Oct. 31.Enjoy your summer on the lake in this remarkable waterfront single-family home. Offering the perfect combination of space, comfort, and timeless charm, this property provides an idyllic lakefront experience. The home features three bedrooms plus a den/office, with sliders that open to a spacious deck overlooking the water—perfect for

    Patty Wagner Compass Greater NY, LLC

    34 Twin Lakes Rd, South Salem, NY 10590
  • /32

    $6,100 Per Month

    • 3 Beds
    • 2 Baths
    • 1,986 Sq Ft
    • House for Rent

    5 Howe St, South Salem, NY 10590

    Charming architectural retreat offering the perfect open-concept flow for effortless entertaining. The heart of the home is an expansive Great Room boasting soaring vaulted wood ceilings with exposed beams, rich hardwood floors, and a dramatic stone wood-burning fireplace with a raised hearth. An expansive wall of glass doors floods the space with natural light and opens seamlessly to a

    Paul Tollefson William Raveis-New York LLC

    5 Howe St, South Salem, NY 10590
  • /21

    $3,700 Per Month

    • 1 Bed
    • 1 Bath
    • 863 Sq Ft
    • House for Rent

    114 Lake Kitchawan Dr, South Salem, NY 10590

    Enjoy peaceful lake area living in this charming reverse living home, ideally located near Lake Kitchawan. This unique layout offers the kitchen and dining area on the lower level, creating a comfortable separation between entertaining and living spaces.Originally designed as a two bedroom home, it has been converted into a spacious one bedroom with an open and airy feel. The home features

    Cindy Aqeel William Raveis-New York LLC

    114 Lake Kitchawan Dr, South Salem, NY 10590
  • /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, 2026 Lakeside 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
  • /10

    $2,850 Per Month

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Apartment for Rent

    205 Waccabuc Rd Unit 7, Goldens Bridge, NY 10526

    Beautifully updated private two bedroom apartment. New kitchen with door out to peaceful yard. Hardwood floors. Lots of closets. One assigned parking space with additional parking available upon request. Laundry room for complex available.

    Zef Vataj Houlihan Lawrence Inc.

    205 Waccabuc Rd Unit 7, Goldens Bridge, NY 10526
  • /25

    $6,950 Per Month

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

    38 Bishop Park Rd, Pound Ridge, NY 10576

    Magical park-like setting! Beautiful expanded ranch located directly on crystal-clear Lake Kitchawan, offering an exceptionally unique and tranquil resort-like lifestyle on a quiet country lane yet easily commutable to New York City. Well laid out floor plan features a gorgeous kitchen, 3 bedrooms, and 2 full baths on the main level, which opens to a large deck perfect for al fresco dining and

    Paul Tollefson William Raveis-New York LLC

    38 Bishop Park Rd, Pound Ridge, NY 10576
  • /18

    $5,500 Per Month

    • 3 Beds
    • 2 Baths
    • 2,400 Sq Ft
    • House for Rent

    35 Quincy Ct S, Goldens Bridge, NY 10526

    Welcome to this newly updated, sun-filled, 3 bedroom, 2 full bath attached ranch that lives like a much larger home. This home features flexible spaces across two levels to accommodate a variety of lifestyles. The main level is comprised of a first floor bedroom, a brand new eat in kitchen, a living room, a playroom or den and a full bathroom. The fully finished, walk-out lower level adds

    Patricia Hinkley Coldwell Banker Realty

    35 Quincy Ct S, Goldens Bridge, NY 10526
  • /36

    $5,500 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
  • /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
  • /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, chefs 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

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, Back Country Greenwich, Cranbury, West Norwalk and Springdale, each with its own character and price range.
How to Rent a Home