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$13,500,000

For Sale - Active
1190 Chestnut Ridge Rd, Dover Plains, NY 12522
5 Beds
8 Baths
5,867 Square Feet
21.43 Acres Lot
Built in 2006
For Sale - Active
Units n/a
Checked: 11 hours ago
Updated: Sep 02, 2025 at 07:42PM

Investment Summary


Monthly Cash Flow
-$66,784
Cap Rate
0.1%
Cash-on-Cash Return
-25.8%
Debt Coverage Ratio
0.02
Internal Rate of Return (5 years)
-20.9%

Property Description


21.43 Acres Lot
Built in 2006
For Sale - Active
Units n/a

Privately sited at the end of a tree-lined drive, this architectural estate enjoys panoramic views over the Hudson Valley and Catskill Mountains. Designed by AD100 architect Gil Schafer, with landscape architecture by Warren Byrd, the home is a Greek Revival masterpiece that blends timeless elegance with modern sophistication. As featured in Elle Decor, the interiors showcase meticulous craftsmanship and richly layered detail. A dramatic double-height entry gallery centers around a sculptural spiral staircase, offering a striking introduction to the home. From there, a 36' x 24' Great Room unfolds with 11'+ ceilings, two wood-burning fireplaces, and French doors leading to an expansive covered porch that captures stunning sunset views. The kitchen is outfitted with top-of-the-line appliances, hand-hewn beams, dual pantries, and an inviting lounge area, perfect for gathering and entertaining. A large-scale wet bar connects the kitchen and great room, while the adjacent dining area opens to a beautifully landscaped pool terrace. A heated breezeway leads to private guest quarters, offering two en-suite bedrooms and a comfortable sitting room. In the west wing, a richly paneled library with fireplace sits beside the serene primary suite, which includes dual dressing rooms, luxurious bathrooms, and views of an English garden and the rolling landscape beyond. Upstairs, two additional bedroom suites each feature private sitting areas and discreet breakfast bars, creating refined and restful retreats. An extraordinary offering where architectural pedigree, design excellence, and natural beauty converge.

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Location


Property Details


Parking

  • Description: 3+ Cars, Attached
  • Garage Spaces: 3
  • Spaces Total: 0

Bedroom Information

  • # of Bedrooms: 5

Bathroom Information

  • # of Baths (Full): 6
  • # of Baths (Total): 8.0

Interior Features

  • # of Rooms: 9
  • # of Stories: 2
  • Basement: Yes
  • Basement Description: Full
  • Fireplace: Yes

Exterior Features

  • Exterior Walls Materials: Wood
  • Pool: Yes

Land Information

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

Lot Information

  • Parcel ID: 1358896864008882100000
  • Lot Size: 933491 sqft

Property Information

  • Property Type: Single Family Residence
  • Style: Estate
  • Year Built: 2006

Tax Information

  • Annual Tax: $49,319

Utilities

  • Water & Sewer: Private, Well
  • Heating: Oil
  • Cooling: Central Air

Location

  • County: Dutchess

Listing Details


Listed by:
Oliver L. Brown
Houlihan Lawrence Inc.
(917) 680-8933

Source:
OneKey MLS
MLS#: 893630
OneKey MLS

Investment Summary


Monthly Cash Flow
-$66,784
Cap Rate
0.1%
Cash-on-Cash Return
-25.8%
Debt Coverage Ratio
0.02
Internal Rate of Return (5 years)
-20.9%

Purchase Details

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Purchase price:
$13,500,000
Amount financed:
-$10,800,000
Down payment:
$2,700,000
Closing costs:
$405,000
Rehab costs:
$0
Initial cash invested:
$3,105,000
Square feet:
5,867
Cost per square foot:
$2,301
Monthly rent per square foot:
$1.38

Financing Details

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Loan amount:
$10,800,000
Loan to value ratio:
80.0%
Loan type:
Amortizing
Term:
30 years
Interest rate:
6.500%
Principal & interest:
$68,263
Property tax:
$4,110
Insurance:
$567
Private mortgage insurance (PMI):
$0
Monthly payment:
$72,940

Operating Income

Find a Property Manager

% Rent Monthly Yearly
Gross rent:
$8,100 $97,200
Vacancy loss: (6%)
6% -$486 -$5,832
Operating income:
$7,614 $91,368

Operating Expenses


% Rent Monthly Yearly
Property taxes: (51%)
51%-$4,110-$49,319
Insurance: (7%)
7%-$567-$6,804
Property management: (8%)
8%-$648-$7,776
Repairs & maintenance: (5%)
5%-$405-$4,860
Capital expenditures: (5%)
5%-$405-$4,860
HOA fees: (n/a)
n/an/an/a
Total operating expenses: (76%)
76%-$6,135-$73,619

Cash Flow


Monthly Yearly
Net operating income:
$1,479 $17,748
Mortgage payments:
-$68,263 -$819,156
Cash flow:
$66,784 $801,408