Lewisboro, NY Homes

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  /30

  $1,795,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 5,960 Sq Ft

  2 Bluestone Ln, South Salem, NY 10590

  This modern 4BR Colonial reimagines classic country living with an effortless work/lifebalance. Privately sited with easy access to shopping, dining, culture and transportation inboth Connecticut and New York, the 3.48-acre property includes a personal trailhead to 7+miles of maintained hiking paths on 370 adjacent Westchester Land Trust and Leon LevyPreserve acres! Bluestone Lane

  Susan Stillman Houlihan Lawrence Inc.

  2 Bluestone Ln, South Salem, NY 10590
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  /13

  $7,000 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

  57 Truesdale Lake Dr, South Salem, NY 10590
• 

  $1,510,000 Sold Mar 03, 2026

  136 Elmwood Rd, South Salem, NY 10590

  • 5 Beds
  • 5.5 Baths
  • 5,687 Sq Ft
  • Built 1873

  Last Sold Summary

  • 1% Above List Price
  • $266/SF
  • 32 Days On Market

  Current Estimated Value $1,500,800

  Last Listing Agent Mark Boyland Keller Williams Realty Partner

  136 Elmwood Rd, South Salem, NY 10590
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  Est $952,993 Not Listed For Sale

  39 Deerfield Rd, Katonah, NY 10536

  • 3 Beds
  • 3 Baths
  • 1,889 Sq Ft
  • Built 1973

  39 Deerfield Rd, Katonah, NY 10536

  Last Sold Summary

  • 27% Above List Price
  • $397/SF
  • 13 Days On Market

  • Last Sold Price $750,000
  • Mar 12, 2024

  Last Listing Agent Patricia Hinkley Coldwell Banker Realty
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  /33

  $1,795,000

  • 4 Beds
  • 3.5 Baths
  • 3,736 Sq Ft

  78 Old Church Ln, Pound Ridge, NY 10576

  Magnificent home set on 4.6 acres of land offering privacy with panoramic views and a pristine modern interior. The first floor of this home features a custom Poggenpohl kitchen with center island and high end appliances that flows to a casual dining and sitting area with a fireplace. The family room boasts a tray ceiling with sliding glass doors to an expansive deck overlooking the beautiful

  Joseph Stilo Julia B Fee Sothebys Int. Rlty

  78 Old Church Ln, Pound Ridge, NY 10576
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  /29

  $2,300 Per Month

  • 1 Bed
  • 1 Bath
  • 675 Sq Ft
  • Property for Rent

  10 Wild Oaks Rd Unit 124, Goldens Bridge, NY 10526

  Beautiful one bedroom in Goldens Bridge in Wild Oaks area. Gut renovation and ready to go! Kitchen which opens up to large living area. Available June 1. Easy app process must be done with board .. Short walk to parking. Looks upon nice courtytard , includes heat, hot water, and parking. Small balcony.

  Joan Cotrone ERA Insite Realty Services

  10 Wild Oaks Rd Unit 124, Goldens Bridge, NY 10526
• 

  $590,000 Sold Aug 20, 2025

  158 Jay Ct Unit 158C, Cross River, NY 10518

  • 1 Bed
  • 2.5 Baths
  • 1,751 Sq Ft
  • Built 1988

  Last Sold Summary

  • 2% Below List Price
  • $337/SF
  • 30 Days On Market

  Current Estimated Value $589,153

  Last Listing Agent James Garcia Coldwell Banker Realty

  158 Jay Ct Unit 158C, Cross River, NY 10518
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  Est $1,074,415 Not Listed For Sale

  48 Schoolhouse Rd, Waccabuc, NY 10597

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft
  • Built 1964

  48 Schoolhouse Rd, Waccabuc, NY 10597

  Last Sold Summary

  • 25% Above List Price
  • $410/SF
  • 172 Days On Market

  • Last Sold Price $860,000
  • Jul 28, 2023

  Last Listing Agent Heather Crabtree Coldwell Banker Realty
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  /25

  $995,000

  • 3 Beds
  • 2.5 Baths
  • 2,865 Sq Ft

  11 Manor Dr, Goldens Bridge, NY 10526

  Cozy private setting to this wonderful Contemporary/Split, with soaring ceilings and an abundance of natural light. Newer driveway with plenty of guest parking. Nice specimen plantings, rock outcroppings, open and wooded spaces. Bonus room/Loft . Partially covered exterior deck, and fire pit seating. A whole house generator, propane powered in case of emergency. In the highly esteemed

  Gerry Weil Keller Williams Realty Partner

  11 Manor Dr, Goldens Bridge, NY 10526
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  /41

  $5,200 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,568 Sq Ft
  • Townhouse for Rent

  280 Boulder Ridge Rd Unit 2F, South Salem, NY 10590

  Tucked into a picturesque wooded hillside in sought after South Salem, NY, this pet friendly, immaculate, upgraded townhouse style condo with 2 bedrooms plus an office/den offers and large storage room offers a rare blend of tranquility, style, and modern convenience. Built in 2017 and set within a beautifully landscaped, park-like community, the residence is surrounded by nature creating a true

  Amy Wilhelm Corcoran Baer & McIntosh

  280 Boulder Ridge Rd Unit 2F, South Salem, NY 10590
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  $419,000 Sold Sep 29, 2025

  52 Bittersweet Ln, South Salem, NY 10590

  • 2 Beds
  • 1 Bath
  • 1,070 Sq Ft
  • Built 1981

  Last Sold Summary

  • 2% Below List Price
  • $392/SF
  • 27 Days On Market

  Current Estimated Value $427,083

  Last Listing Agent Eric Staub Keller Williams NY Realty

  52 Bittersweet Ln, South Salem, NY 10590
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  Est $387,448 Not Listed For Sale

  15 Bishop Park Rd, Pound Ridge, NY 10576

  • 1 Bed
  • 1 Bath
  • 807 Sq Ft
  • Built 1934

  15 Bishop Park Rd, Pound Ridge, NY 10576

  Last Sold Summary

  • 52% Above List Price
  • $316/SF
  • 265 Days On Market

  • Last Sold Price $255,000
  • Jun 25, 2024

  Last Listing Agent Eric Rosenfeld William Raveis-New York LLC
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  /45

  $949,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,120 Sq Ft

  11 Billingsley Trail, Goldens Bridge, NY 10526

  A beautifully maintained and updated home offering 3 bedrooms and 3 bathrooms plus an office situated on lower level near full bathroom making it ideal for a guest/4th bedroom. This brick & cedar shake exterior home is set beautifully on one acre of property, located on a quiet cul-de-sac, offering amazing privacy with level back yard. A unique split-level home features a stunning sunroom

  Bill Reilly Billingsley Realty

  11 Billingsley Trail, Goldens Bridge, NY 10526
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  $600,000 Sold Oct 29, 2025

  59 Grandview Rd, South Salem, NY 10590

  • 3 Beds
  • 1.5 Baths
  • 1,360 Sq Ft
  • Built 1977

  Last Sold Summary

  • 14% Below List Price
  • $441/SF
  • 133 Days On Market

  Current Estimated Value $618,352

  Last Listing Agent Andres Sarmiento RE/MAX Distinguished Hms.&Prop

  59 Grandview Rd, South Salem, NY 10590
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  Est $958,729 Not Listed For Sale

  15 S Shore Dr, South Salem, NY 10590

  • 2 Beds
  • 1 Bath
  • 1,515 Sq Ft
  • Built 1920

  15 S Shore Dr, South Salem, NY 10590

  Last Sold Summary

  • 13% Above List Price
  • $560/SF
  • 102 Days On Market

  • Last Sold Price $849,000
  • Aug 18, 2023

  Last Listing Agent Gina Cooney Giner Real Estate Inc.
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  /24

  $1,100,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,476 Sq Ft

  12 Skytop Dr, Katonah, NY 10536

  Live the Lake Katonah life in this spacious, fully renovated mid-century modern with incredible views. This house embraces open concept living at its best. The great room has direct access out to the spectacular screened porch from both the living and dining rooms and a brand new deck is directly off of the huge eat-in-kitchen. Enjoy the lovely level backyard for great outdoor activities. Walk to

  Angela Kessel Houlihan Lawrence Inc.

  12 Skytop Dr, Katonah, NY 10536
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  $750,000 Sold Aug 25, 2025

  17 Kingswood Way, South Salem, NY 10590

  • 3 Beds
  • 2 Baths
  • 1,690 Sq Ft
  • Built 1974

  Last Sold Summary

  • 6% Above List Price
  • $444/SF
  • 35 Days On Market

  Current Estimated Value $756,579

  Last Listing Agent Maureen Connolly Coldwell Banker Realty

  17 Kingswood Way, South Salem, NY 10590
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  Est $493,749 Not Listed For Sale

  43 S Shore Dr, South Salem, NY 10590

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft
  • Built 1910

  43 S Shore Dr, South Salem, NY 10590

  Last Sold Summary

  • 15% Above List Price
  • $614/SF
  • 48 Days On Market

  • Last Sold Price $430,000
  • Aug 06, 2024

  Last Listing Agent Patricia Hinkley Coldwell Banker Realty
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  /25

  $699,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,620 Sq Ft

  75 Park Rd Extension, Goldens Bridge, NY 10526

  Experience a blend of refined modern living and serene countryside tranquility in this ultra chic townhome situated in ‘THE GLEN’ an enclave characterized by mature plantings, a flowering tree-lined street, and direct access to The Golden’s Bridge Nature Preserve. Located within the award winning Katonah-Lewisboro School District, this sun-drenched and sophisticated 3+ story home is packed with

  Hannah Yates Giner Real Estate Inc.

  75 Park Rd Extension, Goldens Bridge, NY 10526
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  $950,000 Sold Jun 26, 2025

  1 Harriet Ln, Goldens Bridge, NY 10526

  • 3 Beds
  • 2 Baths
  • 2,750 Sq Ft
  • Built 1953

  Last Sold Summary

  • 13% Above List Price
  • $345/SF
  • 9 Days On Market

  Current Estimated Value $960,777

  Last Listing Agent Patricia Hinkley Coldwell Banker Realty

  1 Harriet Ln, Goldens Bridge, NY 10526
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  Est $830,860 Not Listed For Sale

  10 Tommys Ln, South Salem, NY 10590

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • Built 1960

  10 Tommys Ln, South Salem, NY 10590

  Last Sold Summary

  • 6% Above List Price
  • $556/SF
  • 62 Days On Market

  • Last Sold Price $783,000
  • Jul 15, 2024

  Last Listing Agent Melissa Marcogliese Compass Greater NY, LLC
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  /42

  $619,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 2,626 Sq Ft

  10 Guilford Cir, Goldens Bridge, NY 10526

  Rare opportunity in desirable Katonah Close in Goldens Bridge—units here seldom come to market, so don’t miss this one. This bright, tri-level contemporary end-unit townhome offers space, privacy, and convenient living.The main level welcomes you with a two-story entry, hardwood floors and recessed lighting. Very spacious rooms throughout. Enjoy a large eat-in kitchen with a peninsula, formal

  Debra DeMelis Coldwell Banker Realty

  10 Guilford Cir, Goldens Bridge, NY 10526
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  $999,999 Sold Jun 20, 2025

  6 Manor Dr, Goldens Bridge, NY 10526

  • 4 Beds
  • 3 Baths
  • 2,476 Sq Ft
  • Built 1979

  Last Sold Summary

  • 10% Above List Price
  • $404/SF
  • 15 Days On Market

  Current Estimated Value $1,010,681

  Last Listing Agent Julia Klagsbrun Corcoran Legends Realty

  6 Manor Dr, Goldens Bridge, NY 10526
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  Est $1,212,035 Not Listed For Sale

  9 Tommys Ln, South Salem, NY 10590

  • 4 Beds
  • 3.5 Baths
  • 3,389 Sq Ft
  • Built 1976

  9 Tommys Ln, South Salem, NY 10590

  Last Sold Summary

  • 15% Above List Price
  • $311/SF
  • 12 Days On Market

  • Last Sold Price $1,053,000
  • Jun 06, 2023

  Last Listing Agent Mark Boyland Keller Williams Realty Partner
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  /31

  $779,000

  • 3 Beds
  • 2.5 Baths
  • 2,132 Sq Ft

  8 Debbie Ln Unit 6, Cross River, NY 10518

  Welcome to this charming home nestled on a 1.24-acre lot on a quiet cul-de-sac in desirable Cross River, within the Town of Lewisboro and the award-winning Katonah-Lewisboro School District. This beautifully maintained residence offers three bedrooms, 2.5 baths, and flexible living space, perfect for today’s lifestyle. Gleaming hardwood floors throughout and abundant natural light enhance the

  Jessica Cunningham

  8 Debbie Ln Unit 6, Cross River, NY 10518
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  $900,000 Sold Jul 31, 2025

  123 East St, South Salem, NY 10590

  • 4 Beds
  • 3.5 Baths
  • 2,950 Sq Ft
  • Built 1979

  Last Sold Summary

  • 5% Below List Price
  • $305/SF
  • 17 Days On Market

  Current Estimated Value $919,447

  Last Listing Agent Giuseppe 'Joe' Melillo William Raveis Real Estate

  123 East St, South Salem, NY 10590
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  Est $412,250 Not Listed For Sale

  274 Maplewood Dr Unit 32274, South Salem, NY 10590

  • 1 Bed
  • 1 Bath
  • 970 Sq Ft
  • Built 1994

  274 Maplewood Dr Unit 32274, South Salem, NY 10590

  Last Sold Summary

  • 13% Above List Price
  • $376/SF
  • 40 Days On Market

  • Last Sold Price $365,000
  • Aug 31, 2023

  Last Listing Agent Alex Mashkin Keller Williams Realty Partner
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  /27

  $799,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,160 Sq Ft

  3 Mark Mead Rd, Cross River, NY 10518

  Welcome to 3 Mark Mead Road, a sunlit, incredibly spacious home in the adorable hamlet of Cross River. This fully renovated, 2160sq ft home lives much larger than a typical 3 bedroom, 2 bathroom home. The first floor bedroom, 2 second floor bedrooms, and 2 second floor offices/dens ensure there is plenty of space for everyone! The renovated kitchen, with breakfast area featuring whitewashed

  Patricia Hinkley Coldwell Banker Realty

  3 Mark Mead Rd, Cross River, NY 10518
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  $504,000 Sold Oct 28, 2025

  99 Fox Run, South Salem, NY 10590

  • 2 Beds
  • 1 Bath
  • 1,364 Sq Ft
  • Built 1981

  Last Sold Summary

  • 2% Above List Price
  • $370/SF
  • 20 Days On Market

  Current Estimated Value $498,213

  Last Listing Agent Cate Hegarty Compass Greater NY, LLC

  99 Fox Run, South Salem, NY 10590
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  Est $394,512 Not Listed For Sale

  244 Deer Hill Unit 27244, South Salem, NY 10590

  • 1 Bed
  • 1 Bath
  • 994 Sq Ft
  • Built 1988

  244 Deer Hill Unit 27244, South Salem, NY 10590

  Last Sold Summary

  • 10% Above List Price
  • $362/SF
  • 45 Days On Market

  • Last Sold Price $360,000
  • Dec 28, 2023

  Last Listing Agent Alex Mashkin Keller Williams Realty Partner
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  /27

  $2,295,000

  • 4 Beds
  • 3.5 Baths
  • 3,324 Sq Ft

  12 E Ridge Rd, Waccabuc, NY 10597

  Privately set on 4.5 acres along coveted East Ridge Road in the heart of Waccabuc, this beautifully updated residence offers an exceptional balance of tranquility, comfort, and refined country living.Sunlight fills the home’s open, inviting layout, designed for both relaxed everyday living and effortless entertaining. The residence features four bedrooms and three-and-a-half baths,

  Angela Kessel Houlihan Lawrence Inc.

  12 E Ridge Rd, Waccabuc, NY 10597
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  $5,400,000 Sold Jun 16, 2025

  76 E Ridge Rd, Waccabuc, NY 10597

  • 6 Beds
  • 8 Baths
  • 6,211 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $869/SF
  • 23 Days On Market

  Current Estimated Value $4,874,709

  Last Listing Agent Benjamin Ginnel Ginnel Real Estate

  76 E Ridge Rd, Waccabuc, NY 10597
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  Est $573,133 Not Listed For Sale

  230 Lakeside Dr, South Salem, NY 10590

  • 2 Beds
  • 2 Baths
  • 1,468 Sq Ft
  • Built 1987

  230 Lakeside Dr, South Salem, NY 10590

  Last Sold Summary

  • 4% Above List Price
  • $375/SF
  • 6 Days On Market

  • Last Sold Price $550,000
  • Jun 20, 2024

  Last Listing Agent Amanda Goldberg William Raveis-New York, LLC
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  $349,000

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft

  102 Lake Kitchawan Dr, South Salem, NY 10590

  Sold as is, house needs total renovation. Cash buyers only. Backs up to the Leon Levy Preserve, access to Lake Kitchawan Lake. Tucked away along the quiet shoreline of Lake Kitchawan, this modest cape presents a rare chance to reimagine a home in one of Northern Westchester most natural settings. Set on a small parcel that backs directly onto the protected woodlands of the Leon Levy Preserve. The

  Cecilia Heller Houlihan Lawrence Inc.

  102 Lake Kitchawan Dr, South Salem, NY 10590
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  $1,229,900 Sold Jun 18, 2025

  40 Gilbert St, South Salem, NY 10590

  • 3 Beds
  • 4 Baths
  • 2,161 Sq Ft
  • Built 1950

  Last Sold Summary

  • 5% Below List Price
  • $569/SF
  • 46 Days On Market

  Current Estimated Value $1,275,442

  Last Listing Agent Patty Wagner Compass Greater NY, LLC

  40 Gilbert St, South Salem, NY 10590
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  Est $254,633 Not Listed For Sale

  224 Lakeside Dr, South Salem, NY 10590

  • 1 Bed
  • 1 Bath
  • 637 Sq Ft
  • Built 1986

  224 Lakeside Dr, South Salem, NY 10590

  Last Sold Summary

  • 22% Above List Price
  • $329/SF
  • 14 Days On Market

  • Last Sold Price $209,532
  • Dec 10, 2024

  Last Listing Agent Teresa Rivers Coldwell Banker Realty
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  /19

  $695,000

  • 3 Beds
  • 2 Baths
  • 1,393 Sq Ft

  95 Main St, South Salem, NY 10590

  Western View. Over one park-like acre with rolling lawns, flowering plantings and towering trees. First time listed in years, distinctive Country House with elements of a classic deck house. Warm interior spaces with hardwood floors and vaulted ceilings finished in wood. Sun-filled Living Room with fireplace and doors to front deck, ideal for relaxation. Dining Room with vaulted ceiling. Country

  Peter Michaelis Ginnel Real Estate

  95 Main St, South Salem, NY 10590
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  $2,700,000 Sold Jul 29, 2025

  23 Rock Shelter Rd, Waccabuc, NY 10597

  • 5 Beds
  • 9 Baths
  • 8,552 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $316/SF
  • 29 Days On Market

  Current Estimated Value $2,749,003

  Last Listing Agent Angela Kessel Houlihan Lawrence Inc.

  23 Rock Shelter Rd, Waccabuc, NY 10597
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  Est $376,392 Not Listed For Sale

  219 Lakeside Dr, South Salem, NY 10590

  • 1 Bed
  • 1 Bath
  • 994 Sq Ft
  • Built 1987

  219 Lakeside Dr, South Salem, NY 10590

  Last Sold Summary

  • 14% Above List Price
  • $332/SF
  • 32 Days On Market

  • Last Sold Price $330,000
  • Oct 01, 2024

  Last Listing Agent Mark Boyland Keller Williams Realty Partner
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  /49

  $2,250,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 6,622 Sq Ft

  241 N Salem Rd, Waccabuc, NY 10597

  Set on over five private acres in Waccabuc, this custom colonial offers a well-designed layout with quality finishes throughout. A dramatic two-story entry with sweeping staircase leads to gracious formal and casual living spaces featuring 10-foot ceilings, hardwood floors, detailed millwork, and three wood-burning fireplaces. The kitchen is equipped with high-end appliances including a Wolf

  Lindsay Matthews Houlihan Lawrence Inc.

  241 N Salem Rd, Waccabuc, NY 10597

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