New Castle, NY Homes

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  /34

  $1,150,000 Pending

  • 5 Beds
  • 2.5 Baths
  • 2,621 Sq Ft

  28 Barnes Rd, Ossining, NY 10562

  Introducing ROCKDALE c. 1830 — a one-of-a-kind, captivating 5-bedroom historic Colonial farmhouse and barn set on 1.32 bucolic acres. The perfect full-time residence or weekend retreat for those who seek charm, originality, and significance. Proudly listed on the New Castle Historic Registry, this quintessential landmark is rich in history and character. Beautifully situated on a quiet country

  Cindy Glynn Compass Greater NY, LLC

  28 Barnes Rd, Ossining, NY 10562
• 

  $1,679,000 Sold Sep 18, 2025

  10 Carriage Ln Unit 85, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 3,269 Sq Ft
  • Built 2025

  Last Sold Summary

  • $514/SF
  • 137 Days On Market

  Last Listing Agent Andrea Martone Houlihan Lawrence Inc.

  10 Carriage Ln Unit 85, Chappaqua, NY 10514
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  Est $3,188,818 Not Listed For Sale

  3 Trails End, Chappaqua, NY 10514

  • 5 Beds
  • 5.5 Baths
  • 6,083 Sq Ft
  • Built 1994

  3 Trails End, Chappaqua, NY 10514

  Last Sold Summary

  • 12% Above List Price
  • $469/SF
  • 29 Days On Market

  • Last Sold Price $2,850,000
  • Aug 09, 2023

  Last Listing Agent Jennifer Harris Compass Greater NY, LLC
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  /24

  $1,155,000

  • 4 Beds
  • 3 Baths
  • 2,606 Sq Ft

  54 Allapartus Rd, Ossining, NY 10562

  Welcome to your dream home! This bright 4-bedroom, 3-bathroom Ranch offers 1-level living on a serene and private two-acre lot. The property boasts abundant natural light throughout, creating an inviting atmosphere. Step into the expansive, renovated chef's kitchen with professional stainless steel appliances and a center island, which seamlessly flows into the great room with a vaulted ceiling,

  Hope Brasesco Compass Greater NY, LLC

  54 Allapartus Rd, Ossining, NY 10562
• 

  $1,715,408 Sold May 16, 2025

  3 Dewitt Dr Unit 77, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 3,269 Sq Ft
  • Built 2024

  Last Sold Summary

  • 5% Above List Price
  • $525/SF
  • 39 Days On Market

  Current Estimated Value $1,754,796

  Last Listing Agent Thomas Jacovino Toll Brothers Real Estate Inc.

  3 Dewitt Dr Unit 77, Chappaqua, NY 10514
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  Est $2,775,676 Not Listed For Sale

  6 Trails End, Chappaqua, NY 10514

  • 5 Beds
  • 7 Baths
  • 7,624 Sq Ft
  • Built 1994

  6 Trails End, Chappaqua, NY 10514

  Last Sold Summary

  • 12% Above List Price
  • $325/SF
  • 164 Days On Market

  • Last Sold Price $2,480,000
  • May 10, 2024

  Last Listing Agent Yaxing Zhang Houlihan Lawrence Inc.
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  /39

  $795,000

  • 3 Beds
  • 1.5 Baths
  • 1,612 Sq Ft

  101 Spring Valley Rd, Ossining, NY 10562

  Historic farmhouse-style home with original character and some modern updatesSet on a nearly half-acre lot in a quiet, wooded area , detached barn adds flexibility (garage, storage, workshop).Includes large front porch and scenic, “bucolic” surroundings, Hardwood flooring throughout. Located near the Teatown Lake Reservation and major commuter routes, low taxes

  Ted Thompson Christie's Int. Real Estate

  101 Spring Valley Rd, Ossining, NY 10562
• 

  $1,402,970 Sold Jun 23, 2025

  8 Dewitt Dr Unit 66, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 2,945 Sq Ft
  • Built 2024

  Last Sold Summary

  • 5% Above List Price
  • $476/SF
  • 142 Days On Market

  Last Listing Agent Thomas Jacovino Toll Brothers Real Estate Inc.

  8 Dewitt Dr Unit 66, Chappaqua, NY 10514
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  Est $3,124,407 Not Listed For Sale

  6 Paula Place, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 5,272 Sq Ft
  • Built 2005

  6 Paula Place, Chappaqua, NY 10514

  Last Sold Summary

  • 238% Above List Price
  • $175/SF
  • 85 Days On Market

  • Last Sold Price $925,000
  • Dec 11, 2024

  Last Listing Agent Joe Hasselt Joe Hasselt Real Estate
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  /42

  $2,650,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,975 Sq Ft

  3 Pondfield Dr S, Chappaqua, NY 10514

  Welcome to an exceptional move-in ready home located in a highly desirable Chappaqua neighborhood known for its award-winning schools & sought-after lifestyle. Perfectly positioned at the end of a quiet cul-de-sac, this stunning & chic property offers privacy, space & luxury living at its finest. Step inside & you'll find a bright, open-concept floor plan with natural light & high-end finishes

  Lori Meringolo Houlihan Lawrence Inc.

  3 Pondfield Dr S, Chappaqua, NY 10514
• 

  $1,125,000 Sold Jul 21, 2025

  16 Garey Dr, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 1,888 Sq Ft
  • Built 1958

  Last Sold Summary

  • 25% Above List Price
  • $596/SF
  • 18 Days On Market

  Current Estimated Value $1,159,569

  Last Listing Agent Sherry Wiggs Houlihan Lawrence Inc.

  16 Garey Dr, Chappaqua, NY 10514
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  Est $826,391 Not Listed For Sale

  15 Paula Place, Chappaqua, NY 10514

  • 2 Beds
  • 1 Bath
  • 1,160 Sq Ft
  • Built 1952

  15 Paula Place, Chappaqua, NY 10514

  Last Sold Summary

  • 17% Above List Price
  • $608/SF
  • 32 Days On Market

  • Last Sold Price $705,000
  • Jun 28, 2024

  Last Listing Agent Lauren Zaccaria Houlihan Lawrence Inc.
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  /21

  $649,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,292 Sq Ft

  221 N Greeley Ave, Chappaqua, NY 10514

  Fantastic opportunity just steps from downtown Chappaqua. Only a short three minute walk to the heart of town, this property sits on a generous lot with great outdoor space and endless potential. Currently used as a single family home, the Business Retail zoning allows for a variety of uses whether you are an investor, looking for a live work setup, or considering a residential conversion. An

  Robert Dellaero Julia B Fee Sothebys Int. Rlty

  221 N Greeley Ave, Chappaqua, NY 10514
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  $1,320,000 Sold Dec 11, 2025

  41 Valley Ln, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 2,034 Sq Ft
  • Built 1972

  Last Sold Summary

  • 2% Above List Price
  • $649/SF
  • 10 Days On Market

  Current Estimated Value $1,327,741

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

  41 Valley Ln, Chappaqua, NY 10514
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  Est $2,230,139 Not Listed For Sale

  345 Roaring Brook Rd, Chappaqua, NY 10514

  • 4 Beds
  • 4.5 Baths
  • 5,668 Sq Ft
  • Built 1965

  345 Roaring Brook Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 16% Above List Price
  • $340/SF
  • 24 Days On Market

  • Last Sold Price $1,925,000
  • Aug 01, 2024

  Last Listing Agent Sena Baron William Raveis-New York, LLC
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  $3,400,000 Pending

  • 4 Beds
  • 5 Baths
  • 4,236 Sq Ft

  12 Haights Cross Rd, Chappaqua, NY 10514

  Experience the art of living well in this extraordinary private retreat overlooking Heaptaugua Lake. Set on just under five acres, the property offers total serenity while remaining just minutes from Chappaqua’s quaint downtown, restaurants, Metro-North, and shopping. Enter through the gates and follow the sweeping driveway as it curves past the pool house and pool, passing a sweeping lawn before

  Amy Via Houlihan Lawrence Inc.

  12 Haights Cross Rd, Chappaqua, NY 10514
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  $1,502,500 Sold Jun 09, 2025

  60 Cross Ridge Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 2,426 Sq Ft
  • Built 1960

  Last Sold Summary

  • 16% Above List Price
  • $619/SF
  • 6 Days On Market

  Current Estimated Value $1,501,674

  Last Listing Agent Stacy Levey William Raveis-New York, LLC

  60 Cross Ridge Rd, Chappaqua, NY 10514
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  Est $2,402,936 Not Listed For Sale

  15 Kerry Ln, Chappaqua, NY 10514

  • 4 Beds
  • 4 Baths
  • 5,534 Sq Ft
  • Built 1935

  15 Kerry Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 20% Above List Price
  • $361/SF
  • 128 Days On Market

  • Last Sold Price $2,000,000
  • Aug 23, 2024

  Last Listing Agent Janine Marino Houlihan Lawrence Inc.
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  $3,695,000

  • 5 Beds
  • 6.5 Baths
  • 6,500 Sq Ft

  115 Old Roaring Brook Rd, Mount Kisco, NY 10549

  New construction in the highly sought-after Chappaqua Schools within the Town of New Castle! Set on 11+ private acres, this exceptional Westchester estate property offers the ultimate luxury living, privacy, and convenience. Built by a well-known local builder, this 6,500 sq ft home features 3 finished levels, 5 bedrooms, and a walk-out lower level. Highlights include 10’ ceilings on the main

  Sharon Bodnar Briskman Houlihan Lawrence Inc.

  115 Old Roaring Brook Rd, Mount Kisco, NY 10549
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  $2,825,000 Sold Oct 20, 2025

  5 Club Way, Mount Kisco, NY 10549

  • 5 Beds
  • 7 Baths
  • 6,673 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Above List Price
  • $423/SF
  • 44 Days On Market

  Current Estimated Value $2,880,809

  Last Listing Agent Barbara Pagliuca Houlihan Lawrence Inc.

  5 Club Way, Mount Kisco, NY 10549
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  Est $2,030,236 Not Listed For Sale

  28 McKesson Hill Rd, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,541 Sq Ft
  • Built 1967

  28 McKesson Hill Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 6% Above List Price
  • $539/SF
  • 12 Days On Market

  • Last Sold Price $1,909,000
  • Jul 12, 2023

  Last Listing Agent Amanda Acard Nestedge Realty
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  /35

  $2,990,000

  • 6 Beds
  • 5.5 Baths
  • 8,200 Sq Ft

  20 Bessel Ln, Chappaqua, NY 10514

  Nestled in breathtaking natural surroundings, this modern architectural masterpiece by renowned designer Myron Goldfinger offers three levels of striking contemporary design. The residence features a soaring three-story curved ceiling, a dramatic floating staircase, and expansive open-plan living and entertaining spaces that frame the home’s private setting. The main-level primary suite provides

  Tianying Xu Houlihan Lawrence Inc.

  20 Bessel Ln, Chappaqua, NY 10514
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  $1,747,995 Sold Sep 19, 2025

  2 Carriage Ln Unit 81, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 3,269 Sq Ft
  • Built 2024

  Last Sold Summary

  • $535/SF
  • 235 Days On Market

  Current Estimated Value $1,762,682

  Last Listing Agent Thomas Jacovino Toll Brothers Real Estate Inc.

  2 Carriage Ln Unit 81, Chappaqua, NY 10514
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  Est $1,882,057 Not Listed For Sale

  1 Round Hill Rd, Chappaqua, NY 10514

  • 4 Beds
  • 3 Baths
  • 3,164 Sq Ft
  • Built 1963

  1 Round Hill Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 8% Above List Price
  • $553/SF
  • 52 Days On Market

  • Last Sold Price $1,750,000
  • Oct 03, 2024

  Last Listing Agent Elaine Wasserman Houlihan Lawrence Inc.
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  /30

  $799,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,692 Sq Ft

  550 Saw Mill River Rd, Millwood, NY 10546

  Chappaqua Schools. The Pride of Homeownership Starts Here. Tucked away in the highly sought-after Chappaqua School District, this meticulously maintained Raised Ranch blends comfort, style, and functionality in all the right ways. Step inside to find a bright and open layout—perfect for everyday living and entertaining. The spacious living room flows effortlessly into the dining room with sliding

  Yara Annechiarico At Home With Yara Realty

  550 Saw Mill River Rd, Millwood, NY 10546
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  $770,000 Sold Jul 24, 2025

  23 Pineview Rd, Mount Kisco, NY 10549

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft
  • Built 1976

  Last Sold Summary

  • 13% Above List Price
  • $430/SF
  • 8 Days On Market

  Current Estimated Value $814,884

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  23 Pineview Rd, Mount Kisco, NY 10549
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  Est $2,062,371 Not Listed For Sale

  2 Sunset Dr, Chappaqua, NY 10514

  • 4 Beds
  • 6 Baths
  • 5,474 Sq Ft
  • Built 1986

  2 Sunset Dr, Chappaqua, NY 10514

  Last Sold Summary

  • 17% Above List Price
  • $322/SF
  • 6 Days On Market

  • Last Sold Price $1,760,000
  • Jun 10, 2024

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC
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  /24

  $1,299,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,892 Sq Ft

  56 Cross Ridge Rd, Chappaqua, NY 10514

  Bright and inviting, this 4-bedroom, 2.5-bath Colonial is ideally located with easy access to downtown Chappaqua, Metro-North, shops, dining, and local schools, offering the perfect balance of convenience and neighborhood charm. Thoughtfully designed for both everyday living and entertaining, the main level features a well-designed and functional layout with an open kitchen that flows seamlessly

  Sari Shaw Compass Greater NY, LLC

  56 Cross Ridge Rd, Chappaqua, NY 10514
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  $1,391,022 Sold Oct 23, 2025

  6 Algonquin Dr, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,776 Sq Ft
  • Built 1952

  Last Sold Summary

  • 16% Above List Price
  • $368/SF
  • 30 Days On Market

  Current Estimated Value $1,435,083

  Last Listing Agent Lindsay Rothman Compass Greater NY LLC

  6 Algonquin Dr, Chappaqua, NY 10514
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  Est $1,445,086 Not Listed For Sale

  12 Seven Bridges Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 2,543 Sq Ft
  • Built 1950

  12 Seven Bridges Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 2% Above List Price
  • $554/SF
  • 13 Days On Market

  • Last Sold Price $1,410,000
  • Apr 15, 2025

  Last Listing Agent Brendan Preston Houlihan Lawrence Inc.
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  /21

  $2,850,000 Pending

  • 4 Beds
  • 7 Baths
  • 5,536 Sq Ft

  211 Bedford Rd, Chappaqua, NY 10514

  Exciting and new state-of-the-art expansion and renovation by highly recognized local developer, Tavo Development teaming with noted architect Teo Seguenza. Ready for occupancy in Spring 2026. Meticulous attention to detail, years of experience and master craftsmanship are combined in this new offering, encompassing 5,536 sq ft, 4 bedrooms, 5 full and 2 half baths, a finished walk-out lower level

  Brian Milton Compass Greater NY, LLC

  211 Bedford Rd, Chappaqua, NY 10514
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  $732,500 Sold Dec 15, 2025

  30 Rambling Brook Rd, Chappaqua, NY 10514

  • 2 Beds
  • 2.5 Baths
  • 1,244 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Below List Price
  • $589/SF
  • 24 Days On Market

  Current Estimated Value $734,761

  Last Listing Agent Amanda Acard Nestedge Realty

  30 Rambling Brook Rd, Chappaqua, NY 10514
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  Est $1,243,961 Not Listed For Sale

  610 Quaker Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 2,022 Sq Ft
  • Built 1954

  610 Quaker Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 107% Above List Price
  • $297/SF
  • 2 Days On Market

  • Last Sold Price $600,000
  • Dec 07, 2023

  Last Listing Agent Igor Krasnoperov Rising Star Realty
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  $1,549,000

  • 2 Beds
  • 3.5 Baths
  • 3,040 Sq Ft

  125 Cross River Rd, Mount Kisco, NY 10549

  Welcome to 125 Cross River Road, an exceptional, sun-filled home that truly delivers a “wow” from the moment you enter. Thoughtfully renovated, this light-filled two-bedroom, 3.5-bath residence offers exceptional versatility beyond its stated bedroom count. Multiple finished rooms and flexible living areas provide a variety of options for today’s lifestyle needs, including home offices, guest

  Catherine O'Connor Houlihan Lawrence Inc.

  125 Cross River Rd, Mount Kisco, NY 10549
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  $1,530,000 Sold Sep 12, 2025

  31 Wynnewood Rd, Chappaqua, NY 10514

  • 4 Beds
  • 3 Baths
  • 2,420 Sq Ft
  • Built 1928

  Last Sold Summary

  • 22% Above List Price
  • $632/SF
  • 9 Days On Market

  Current Estimated Value $1,491,259

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  31 Wynnewood Rd, Chappaqua, NY 10514
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  Est $1,583,799 Not Listed For Sale

  15 Suzanne Ln, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,032 Sq Ft
  • Built 1965

  15 Suzanne Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 21% Above List Price
  • $431/SF
  • 14 Days On Market

  • Last Sold Price $1,307,000
  • Jun 14, 2023

  Last Listing Agent MaryAnn Bayer Compass Greater NY, LLC
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  $2,050,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 5,792 Sq Ft

  114 Random Farms Dr, Chappaqua, NY 10514

  Spectacular and turnkey center hall Colonial in the desirable Random Farms community within the highly coveted Chappaqua School District. Perched atop a hill, this home enjoys sweeping views and breathtaking sunsets from a private setting. Boasting 5 spacious bedrooms and 4.1 baths across three beautifully finished levels, this home offers 5,792 sq ft of beautifully designed living space, filled

  Cindy Glynn Compass Greater NY, LLC

  114 Random Farms Dr, Chappaqua, NY 10514
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  $1,780,018 Sold Apr 25, 2025

  83 Indian Hill Rd, Mount Kisco, NY 10549

  • 4 Beds
  • 4.5 Baths
  • 4,102 Sq Ft
  • Built 1982

  Last Sold Summary

  • 19% Above List Price
  • $434/SF
  • 7 Days On Market

  Current Estimated Value $1,838,061

  Last Listing Agent Sena Baron William Raveis-New York, LLC

  83 Indian Hill Rd, Mount Kisco, NY 10549
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  Est $1,288,198 Not Listed For Sale

  619 Quaker Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft
  • Built 1961

  619 Quaker Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 22% Above List Price
  • $564/SF
  • 33 Days On Market

  • Last Sold Price $1,055,000
  • Jun 16, 2023

  Last Listing Agent Karin Kimtis Compass Greater NY, LLC
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  $1,750,000

  • Land
  • 12.92 Acres
  • $135,449 per Acre

  767 King St, Chappaqua, NY 10514

  Extremely rare and ultra-private 12.92 acres of waterfront land in the Whippoorwill Lake enclave of Chappaqua. An exceptionally private canvas for a one-of-a-kind secluded getaway compound. Beyond the gate, a long private drive ascends to a concealed building site with sweeping lake and woodland vistas, plus natural water features including a waterfall and bridge. Near Whippoorwill Park,

  Sena Baron William Raveis-New York, LLC

  767 King St, Chappaqua, NY 10514

Showing Results 161 - 200, Page 5 of 18