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$2,000,000

Sale Pending
50 Overlook Dr, Chappaqua, NY 10514
6 Beds
6 Baths
5,234 Square Feet
1.20 Acres Lot
Built in 1929
Sale Pending
Units n/a
Checked: 13 hours ago
Updated: Sep 03, 2025 at 10:06AM

Investment Summary


Monthly Cash Flow
-$7,768
Cap Rate
1.4%
Cash-on-Cash Return
-20.3%
Debt Coverage Ratio
0.23
Internal Rate of Return (5 years)
-15.6%

Property Description


1.20 Acres Lot
Built in 1929
Sale Pending
Units n/a

50 Overlook Drive, an elegant 6-bedroom colonial Tudor set in a quiet, tree-lined neighborhood. With fresh upgrades completed this month, including interior repainting, carpet-removal to expose wood floors. This one-of-a-kind home is a must see. Meticulously maintained heating and cooling systems, brick exterior, and a classic-tile roof are some of the exceptional features this home can offer. Homes built to this quality are a rare find. Constructed in 1929, the home is also graced with soaring ceilings, intricate period moldings, and expansive sunlit interiors. Designed for both grand entertaining and comfortable living, this spacious home is roaring with charm and can suit a variety of tastes and living styles. The first floor offers a living room with fireplace, an all seasons sunroom, a bright and airy dining room, a kitchen with pantry and wet-bar, a half bath, and an in-law or au pair suite with a full bath. Upstairs features 5 bedrooms and 3 full baths, a grand hallway, and attic access. Additional recreational space is provided in the finished basement, with a family room, a gym, and large mudroom, a half-bath, and a utility room. The beautifully landscaped 1.2-acre lot boasts stunning specimen plantings and a private stone patio adjacent to the all-seasons sunroom. There is also a charming bridge, designed by renowned architect Ned Baldwin, leading to a park-like setting in the backyard. This is an incredible opportunity to own a truly distinguished home in one of Chappaqua’s most desirable neighborhoods. Experience the perfect balance of classic architecture and modern luxury in this extraordinary residence, in a home that is built to stand the test of time.

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Location


Property Details


Parking

  • Description: Attached, Driveway
  • Details: Attached, Driveway
  • Garage Spaces: 2
  • Spaces Total: 0

Bedroom Information

  • # of Bedrooms: 6

Bathroom Information

  • # of Baths (Full): 4
  • # of Baths (Partial): 2
  • # of Baths (Total): 6.0

Interior Features

  • # of Rooms: 15
  • # of Stories: 2
  • Basement: Yes
  • Basement Description: Full, Partially Finished, Storage Space
  • Fireplace: Yes

Exterior Features

  • Exterior Walls Materials: Brick

Land Information

  • Land Use: Residential
  • Land Use Subtype: Single Family Residential

Lot Information

  • Parcel ID: 55360093.1743
  • Lot Size: 52272 sqft

Property Information

  • Property Type: Single Family Residence
  • Style: Colonial, Tudor
  • Year Built: 1929

Tax Information

  • Annual Tax: $47,202

Utilities

  • Water & Sewer: Public
  • Heating: Hot Water, Steam, Radiant Floor
  • Cooling: Central Air

Location

  • County: Westchester

Listing Details


Listed by:
Wendy Nolan
Houlihan Lawrence Inc.
(914) 610-6334

Source:
OneKey MLS
MLS#: 877002
OneKey MLS

Investment Summary


Monthly Cash Flow
-$7,768
Cap Rate
1.4%
Cash-on-Cash Return
-20.3%
Debt Coverage Ratio
0.23
Internal Rate of Return (5 years)
-15.6%

Purchase Details

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Purchase price:
$2,000,000
Amount financed:
-$1,600,000
Down payment:
$400,000
Closing costs:
$60,000
Rehab costs:
$0
Initial cash invested:
$460,000
Square feet:
5,234
Cost per square foot:
$382
Monthly rent per square foot:
$1.74

Financing Details

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Loan amount:
$1,600,000
Loan to value ratio:
80.0%
Loan type:
Amortizing
Term:
30 years
Interest rate:
6.500%
Principal & interest:
$10,113
Property tax:
$3,934
Insurance:
$637
Private mortgage insurance (PMI):
$0
Monthly payment:
$14,684

Operating Income

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% Rent Monthly Yearly
Gross rent:
$9,100 $109,200
Vacancy loss: (6%)
6% -$546 -$6,552
Operating income:
$8,554 $102,648

Operating Expenses


% Rent Monthly Yearly
Property taxes: (43%)
43%-$3,934-$47,202
Insurance: (7%)
7%-$637-$7,644
Property management: (8%)
8%-$728-$8,736
Repairs & maintenance: (5%)
5%-$455-$5,460
Capital expenditures: (5%)
5%-$455-$5,460
HOA fees: (n/a)
n/an/an/a
Total operating expenses: (68%)
68%-$6,209-$74,502

Cash Flow


Monthly Yearly
Net operating income:
$2,345 $28,140
Mortgage payments:
-$10,113 -$121,356
Cash flow:
$7,768 $93,216