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$765,000

Sold
557 Upper Grassy Hill Rd, Woodbury, CT 06798
4 Beds
4 Baths
2,791 Square Feet
0.00 Acres Lot
Built in 1999
Sold
Units n/a
Checked: 17 hours ago
Updated: Oct 25, 2025 at 12:10AM

Investment Summary


Monthly Cash Flow
-$719
Cap Rate
4.6%
Cash-on-Cash Return
-4.9%
Debt Coverage Ratio
0.80
Internal Rate of Return (5 years)
-0.8%

Property Description


0.00 Acres Lot
Built in 1999
Sold
Units n/a

This impeccably maintained Colonial home, nestled in a coveted section of Woodbury showcases three levels of living space. Begin with a grand two-story foyer graced w/ marble flooring. The 1st level has a well-appointed office with custom built-ins, bright and spacious LR & DR that spans from front to back, and an open kitchen w/ granite counters, S.S appliances, a built-in wine cooler, and a dining area w/ natural light from windows and skylights. Adjacent to the kitchen, a sunken family room features fresh hardwood floors and an efficient new pellet stove. Beyond the dining area lies a deck with distant views and abundant privacy. The 2nd level reveals 3 generously proportioned bedrooms, including a primary suite spanning three rooms. The suite boasts Trey ceilings, Hickory floors, dual walk-in closets, a cozy sitting room, and a custom en suite bathroom with W-in closet and laundry. The 2nd 3rd bedrooms provide ample closet space and share a well appointed full bath. Descending to the lower level, a space exuding warmth and natural light extends the living area by over 900 sq. Ft. 11-foot ceilings, hickory flooring, a marble bath & steam shower, kitchen area with granite countertops, a charming built-in seating nook, and a Murphy bed for guests, this floor is an inviting retreat. French doors give access to a bluestone patio, a plunge pool, and a meticulously manicured yard. Irrigation, Generator, and surround sound complete this home. 90 min to NYC and 30 min to train.

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Location


Property Details


Parking

  • Description: Garage
  • Details: Asphalt, Garage Door Opener, Private, Attached
  • Garage Spaces: 2
  • Spaces Total: 0

Bedroom Information

  • # of Bedrooms: 4

Bathroom Information

  • # of Baths (Full): 3
  • # of Baths (Partial): 1
  • # of Baths (Total): 4.0

Interior Features

  • # of Rooms: 11
  • # of Stories: 2
  • Basement Description: Partially Finished, Walk-Out Access, Full

Exterior Features

  • Exterior Walls Materials: Siding (Alum/Vinyl)
  • Foundation: Concrete Perimeter
  • Roof Type: Hip
  • Roof Material: Fiberglass

HOA

  • Has HOA: Yes
  • HOA Fee: $200

Land Information

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

Lot Information

  • Parcel ID: WOODM:062B:022LL:12
  • Lot Size: 0 sqft

Property Information

  • Property Type: Single Family Residence
  • Style: Colonial, Contemporary
  • Year Built: 1999

Tax Information

  • Annual Tax: $12,382

Utilities

  • Water & Sewer: Well
  • Heating: Fireplace Insert, Oil, Propane, Forced Air, Zoned
  • Cooling: Central Air

Location

  • County: Litchfield

Listing Details


Listed by:
Jeffrey Boucher
Drakeley Real Estate, Inc.
(203) 709-1423

Source:
SmartMLS
MLS#: 170606501
SmartMLS

Investment Summary


Monthly Cash Flow
-$719
Cap Rate
4.6%
Cash-on-Cash Return
-4.9%
Debt Coverage Ratio
0.80
Internal Rate of Return (5 years)
-0.8%

Purchase Details

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Purchase price:
$765,000
Amount financed:
-$612,000
Down payment:
$153,000
Closing costs:
$22,950
Rehab costs:
$0
Initial cash invested:
$175,950
Square feet:
2,791
Cost per square foot:
$274
Monthly rent per square foot:
$2.04

Financing Details

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Loan amount:
$612,000
Loan to value ratio:
80.0%
Loan type:
Amortizing
Term:
30 years
Interest rate:
5.875%
Principal & interest:
$3,620
Property tax:
$1,032
Insurance:
$399
Private mortgage insurance (PMI):
$0
Monthly payment:
$5,051

Operating Income

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% Rent Monthly Yearly
Gross rent:
$5,700 $68,400
Vacancy loss: (6%)
6% -$342 -$4,104
Operating income:
$5,358 $64,296

Operating Expenses


% Rent Monthly Yearly
Property taxes: (18%)
18%-$1,032-$12,382
Insurance: (7%)
7%-$399-$4,788
Property management: (8%)
8%-$456-$5,472
Repairs & maintenance: (5%)
5%-$285-$3,420
Capital expenditures: (5%)
5%-$285-$3,420
HOA fees: (n/a)
n/an/an/a
Total operating expenses: (43%)
43%-$2,457-$29,482

Cash Flow


Monthly Yearly
Net operating income:
$2,901 $34,812
Mortgage payments:
-$3,620 -$43,440
Cash flow:
-$719 -$8,628