OneKey® MLS
  • Buy
  • Rent
  • Commercial
  • Find an Agent
  • Fair Housing Notices
  • Language
    Price range
    $
    $
    Bedrooms
    Bathrooms
    Home type
    Square feet
    Lot size
    Heating
    Cooling
    Parking spots
    Garage
    Basement
    Year built
    Max HOA
    Down payment assistanceDown payment assistance
    Tours
    View
    More amenities
    1 home
    1 home available
    Pending
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    $7,950,000
    6beds
    6 full, 3 halfbath
    15,000sqft
    5.12acres
    House for Sale

    38 Chestnut Hill Drive, Upper Brookville, NY 11771

    Listing by: Nest Seekers LLC
    1 - 1 of 1 results
    Copyright © 2025 OneKey® MLS LLC
    Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
    Equal opportunity
    Membio
    OneKey® MLS
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    38 Chestnut Hill Drive, Upper Brookville, NY 11771
    Pending
    $7,950,000
    6beds
    6full,3half bath
    15,000sqft
    5.12acres

    38 Chestnut Hill Drive, Upper Brookville, NY 11771

    City/Town:Upper Brookville   Post Office: Upper Brookville     

    House for Sale by Shawn R. ElliottNest Seekers LLC.

    Data checked -. Listing last updated 5 days ago.
    1. Overview
    2. Details
    3. More 

    Nestled in the cul-de-sac of Chestnut Hill Estates, one of Upper Brookville’s most sought-after developments, this 15,000 sq. ft. estate redefines luxury living on over 5 acres of impeccably manicured grounds. A grand 30-foot marble-floored foyer with twin floating staircases makes an unforgettable first impression, highlighting masterful craftsmanship with intricate plaster moldings and marble flooring throughout. The first floor is designed for both grand entertaining and intimate gatherings, featuring a 65-ft formal living room, formal dining room, sitting room, and family room — each with elegant marble fireplaces. The chef’s kitchen is a masterpiece with radiant heat, a Sub-Zero refrigerator and freezer, 60” Viking range, three Bosch dishwashers, and a butler’s pantry complete with a warming oven and additional dishwasher. A luxurious junior primary suite provides privacy and convenience, complemented by a full bath. Nearby, a dedicated spa area with a sauna offers the ultimate in relaxation. The second-floor primary suite is a private sanctuary with a fireplace, 14-ft coffered ceilings, a kitchenette, office, and his-and-hers walk-in closets. Four additional en-suite bedrooms, each with walk-in closets, complete the upper level. This estate’s 20x50 indoor/outdoor pool with a retractable roof, jacuzzi, and spa is a standout feature, seamlessly merging indoor luxury with outdoor tranquility. A media room on the main level and a state-of-the-art fitness center add to the home’s impressive amenities. The 6,500 sq. ft. finished lower level, with marble flooring, features three guest suites and expansive gathering areas. Outside, formal gardens in the rear of the property provide a serene escape, enhancing the estate’s grandeur. Additional highlights include an elevator servicing all three levels, a 10-car garage, and a third-floor cupola with breathtaking 360° views. Located in one of Upper Brookville’s premier enclaves, this estate offers a rare blend of timeless elegance and cutting-edge design.

    Details
      Property type
    Residential
      Year built
    1998
      Heating
    Baseboard
      Cooling
    Central Air
      Total rooms
    15
      Garage
    Yes (10 space)
      City/Town
    Upper Brookville
      Post Office
    Upper Brookville
      Parking spots
    -
    811272
    MLS ID
    Pending
    Status
    01/09/2025
    On Market Date
      Laundry features
      Flooring
      Fireplace
    Yes
      Pets allowed
      Architectural Style
    Colonial
      View
    Interior features
    Chefs Kitchen, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, High Ceilings, Primary Bathroom, Master Downstairs, Walk-In Closet(s)
    Exterior features
    Lot features
    Appliances included
    Dishwasher, Dryer, Oven, Refrigerator
    Construction materials
    Brick, Stucco
    Monthly taxes
    $7,068
    Yearly taxes
    $84,811
    Community Features
    -
    School district
    Locust Valley
    Schools
    Contact Agent, Locust Valley Middle School, Locust Valley High School
    Senior community
    No
    Common Charges
    -
    Maintenance
    -
    Additional Fees
    -
    Open Houses
    In-Person
    No upcoming in-person open houses
    Virtual
    No upcoming virtual open houses
    Contact Agent
    Listing By:
    Shawn R. Elliott
    Shawn R. Elliott
    Shawn R. Elliott
    Zachary Elliott
    Shawn R. Elliott
    Shawn R. Elliott
    Real Estate Salesperson, Nest Seekers LLC
    Direct Number 
     
    Shawn R. Elliott
    Zachary Elliott
    Real Estate Salesperson, Nest Seekers LLC
    Direct Number 
     
    Location
    For Sale Nearby
    19 Pine Street, Port Jervis, NY 12771
    $400,000
    3beds
    2bath
    1,668sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    19 Pine Street, Port Jervis, NY 12771

    Listing by: Realty Executives Exceptional
    41 Grandview Avenue, Port Jervis, NY 12771
    $19,900
    acres
    Land for Sale

    41 Grandview Avenue, Port Jervis, NY 12771

    Listing by: Century 21 Geba Realty
    135 Peenpack Trail, Huguenot, NY 12746
    $125,000
    3beds
    2bath
    2,457sqft
    acres
    House for Sale

    135 Peenpack Trail, Huguenot, NY 12746

    Listing by: John J Lease REALTORS Inc
    9 New Street, Port Jervis, NY 12771
    $217,000
    4beds
    2bath
    1,656sqft
    acres
    House for Sale

    9 New Street, Port Jervis, NY 12771

    Listing by: LBH Real Estate
    300 E Main Street, Port Jervis, NY 12771
    $145,000
    3beds
    1bath
    1,392sqft
    acres
    House for Sale

    300 E Main Street, Port Jervis, NY 12771

    Listing by: Coldwell Banker Realty
    741 Mountain Road, Port Jervis, NY 12771
    $650,000
    4beds
    3bath
    2,708sqft
    acres
    House for Sale

    741 Mountain Road, Port Jervis, NY 12771

    Listing by: Keller Williams Realty
    17 Painted Apron Terrace, Port Jervis, NY 12771
    $370,000
    3beds
    2bath
    1,400sqft
    acres
    House for Sale

    17 Painted Apron Terrace, Port Jervis, NY 12771

    Listing by: Keller Williams Hudson Valley
    12 Kellogg Avenue, Port Jervis, NY 12771
    $285,000
    3beds
    1.5bath
    1,176sqft
    acres
    House for Sale

    12 Kellogg Avenue, Port Jervis, NY 12771

    Listing by: RE/MAX Benchmark Realty Group
    1100 Macintosh Way, Other, PA 18336
    $450,000
    2beds
    2.5bath
    2,200sqft
    acres
    Condo for Sale
    Down payment assistanceDown Payment Help

    1100 Macintosh Way, Other, PA 18336

    Listing by: Century 21 Geba Realty
    12 Hasbrouck Street, Port Jervis, NY 12771
    $425,000
    4beds
    2.5bath
    2,172sqft
    acres
    House for Sale

    12 Hasbrouck Street, Port Jervis, NY 12771

    Listing by: RE/MAX Town & Country
    Recently Sold
    Closed Apr 11
    19 Pine Street, Port Jervis, NY 12771
    $400,000
    3beds
    2bath
    6,199sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    19 Pine Street, Port Jervis, NY 12771

    Listing by: Realty Executives Exceptional
    Closed Apr 9
    41 Grandview Avenue, Port Jervis, NY 12771
    $19,900
    acres
    Land for Sale

    41 Grandview Avenue, Port Jervis, NY 12771

    Listing by: Century 21 Geba Realty
    Closed Apr 8
    135 Peenpack Trail, Huguenot, NY 12746
    $125,000
    3beds
    2bath
    87,120sqft
    acres
    House for Sale

    135 Peenpack Trail, Huguenot, NY 12746

    Listing by: John J Lease REALTORS Inc
    Closed Apr 3
    9 New Street, Port Jervis, NY 12771
    $217,000
    4beds
    2bath
    4,250sqft
    acres
    House for Sale

    9 New Street, Port Jervis, NY 12771

    Listing by: LBH Real Estate
    Closed Apr 2
    300 E Main Street, Port Jervis, NY 12771
    $145,000
    3beds
    1bath
    11,615sqft
    acres
    House for Sale

    300 E Main Street, Port Jervis, NY 12771

    Listing by: Coldwell Banker Realty
    Closed Apr 2
    741 Mountain Road, Port Jervis, NY 12771
    $650,000
    4beds
    3bath
    206,910sqft
    acres
    House for Sale

    741 Mountain Road, Port Jervis, NY 12771

    Listing by: Keller Williams Realty
    Closed Apr 1
    17 Painted Apron Terrace, Port Jervis, NY 12771
    $370,000
    3beds
    2bath
    24,750sqft
    acres
    House for Sale

    17 Painted Apron Terrace, Port Jervis, NY 12771

    Listing by: Keller Williams Hudson Valley
    Closed Mar 31
    12 Kellogg Avenue, Port Jervis, NY 12771
    $285,000
    3beds
    1.5bath
    3,800sqft
    acres
    House for Sale

    12 Kellogg Avenue, Port Jervis, NY 12771

    Listing by: RE/MAX Benchmark Realty Group
    Closed Mar 31
    1100 Macintosh Way, Other, PA 18336
    $450,000
    2beds
    2.5bath
    2,614sqft
    acres
    Condo for Sale
    Down payment assistanceDown Payment Help

    1100 Macintosh Way, Other, PA 18336

    Listing by: Century 21 Geba Realty
    Closed Mar 28
    12 Hasbrouck Street, Port Jervis, NY 12771
    $425,000
    4beds
    2.5bath
    31,250sqft
    acres
    House for Sale

    12 Hasbrouck Street, Port Jervis, NY 12771

    Listing by: RE/MAX Town & Country
    38 Chestnut Hill Drive, Upper Brookville, NY 11771, is a 6 bedroom, 6 bathroom, 15000 sqft. Single Family Residence built in 1998. This property is currently available for sale and was listed on OneKey® MLS on 1-9-2025. The MLS# for this Single Family Residence is MLS# 811272.
    Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
    Copyright ©2025
    BESbswy