Skip to content
×
Pro Members Get
Full Access!
Get off the sidelines and take action in real estate investing with BiggerPockets Pro. Our comprehensive suite of tools and resources minimize mistakes, support informed decisions, and propel you to success.
Advanced networking features
Market and Deal Finder tools
Property analysis calculators
Landlord Command Center
ANNUAL Save 16%
$32.50 /mo
$390 billed annualy
MONTHLY
$39 /mo
billed monthly
7 day free trial. Cancel anytime
Copied
Photo
Copied
Photo
Photo
Photo
Photo
See all photos

$1,795,000

Sale Pending
37 Giles Hill Rd, Redding, CT 06896
5 Beds
4 Baths
6,101 Square Feet
0.00 Acres Lot
Built in 1985
Sale Pending
Units n/a
Checked: 7 hours ago
Updated: Aug 14, 2025 at 06:55AM

Investment Summary


Monthly Cash Flow
-$4,017
Cap Rate
3.0%
Cash-on-Cash Return
-11.7%
Debt Coverage Ratio
0.53
Internal Rate of Return (5 years)
-7.3%

Property Description


0.00 Acres Lot
Built in 1985
Sale Pending
Units n/a

More than a home, this soulful country estate is a living, breathing sanctuary-a place to reconnect with nature, beauty, and what matters most. This quintessential CT farmhouse is like new in every way, but steeped in New England tradition with split rail fencing, over a dozen stone walls, charming front porch, rolling lawn, plus mature flowering trees/gardens. Set back from the road on nearly 5 private acres along one of Redding's most scenic stretches, this exceptional estate offers a rare blend of timeless elegance, modern comfort, and bucolic privacy. Inside, over 6,000 sf of beautifully updated living space unfolds. The soaring great room and chef's kitchen-anchored by double islands, Viking and Sub-Zero appliances-form the true heart of the home. An inviting double fireplace opens to both the kitchen & living room. Five spacious bedrooms offer comfort & privacy, including a serene primary suite with vaulted ceilings & peaceful views. A finished 3rd floor adds flexibility for guests or creative pursuits. Above the detached 3 car garage, a private studio/gym offers endless possibilities for wellness, work, or quiet retreat. Step outside and you're immersed in nature: terraced gardens, a saltwater pool, sport court, and a two-tiered mahogany deck with sunset views over rolling ridgelines and neighboring horse farms. The landscape has been intentionally planted with native, pollinator-friendly species, welcoming butterflies, hummingbirds, and songbirds. Truly special.

Build Your Team


Quickly find investor-friendly professionals who can help you succeed in real estate investing at any stage of the investing journey.

Avatar
Avatar
Avatar

Agents

Match with investor-friendly agents who can help you find, analyze, and close your next deal

Find an Agent
Avatar
Avatar
Avatar

Lenders

Get the best funding…find investor-friendly lenders who specialize in your deal strategy

Find a Lender
Avatar
Avatar
Avatar

Property Managers

Transition to passive investing. Find a trusted property management partnership that lasts.

Find a Property Manager
Avatar
Avatar
Avatar

Tax Pros & Accountants

Taxes and financial reporting made easy—find experts to create tax savings strategies, file taxes, and more

Find a Tax Pro

Location


Property Details


Parking

  • Description: Garage
  • Garage Spaces: 3
  • Spaces Total: 0

Bedroom Information

  • # of Bedrooms: 5

Bathroom Information

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

Interior Features

  • # of Rooms: 13
  • Basement: Yes
  • Basement Description: Full, Finished, Storage Space
  • Fireplace: Yes

Exterior Features

  • Foundation: Concrete Perimeter
  • Roof Material: Asphalt
  • Pool: Yes

Land Information

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

Lot Information

  • Parcel ID: REDDM:31L:94
  • Lot Size: 0 sqft

Property Information

  • Property Type: Single Family Residence
  • Style: Colonial, Farm House
  • Year Built: 1985

Tax Information

  • Annual Tax: $27,416

Utilities

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

Location

  • County: Fairfield

Listing Details


Listed by:
Laura Ancona
William Pitt Sotheby's Int'l
(203) 438-9531

Source:
SmartMLS
MLS#: 24110300
SmartMLS

Investment Summary


Monthly Cash Flow
-$4,017
Cap Rate
3.0%
Cash-on-Cash Return
-11.7%
Debt Coverage Ratio
0.53
Internal Rate of Return (5 years)
-7.3%

Purchase Details

Find an Agent

Purchase price:
$1,795,000
Amount financed:
-$1,436,000
Down payment:
$359,000
Closing costs:
$53,850
Rehab costs:
$0
Initial cash invested:
$412,850
Square feet:
6,101
Cost per square foot:
$294
Monthly rent per square foot:
$1.61

Financing Details

Find a Lender

Loan amount:
$1,436,000
Loan to value ratio:
80.0%
Loan type:
Amortizing
Term:
30 years
Interest rate:
5.875%
Principal & interest:
$8,494
Property tax:
$2,285
Insurance:
$686
Private mortgage insurance (PMI):
$0
Monthly payment:
$11,465

Operating Income

Find a Property Manager

% Rent Monthly Yearly
Gross rent:
$9,800 $117,600
Vacancy loss: (6%)
6% -$588 -$7,056
Operating income:
$9,212 $110,544

Operating Expenses


% Rent Monthly Yearly
Property taxes: (23%)
23%-$2,285-$27,416
Insurance: (7%)
7%-$686-$8,232
Property management: (8%)
8%-$784-$9,408
Repairs & maintenance: (5%)
5%-$490-$5,880
Capital expenditures: (5%)
5%-$490-$5,880
HOA fees: (n/a)
n/an/an/a
Total operating expenses: (48%)
48%-$4,735-$56,816

Cash Flow


Monthly Yearly
Net operating income:
$4,477 $53,724
Mortgage payments:
-$8,494 -$101,928
Cash flow:
$4,017 $48,204