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$2,199,999

For Sale - Active
1752 Chestnut Ave, Winter Park, FL 32789
4 Beds
5 Baths
3,314 Square Feet
0.22 Acres Lot
Built in 2021
For Sale - Active
Units n/a
Checked: 23 hours ago
Updated: Sep 01, 2025 at 10:04AM

Investment Summary


Monthly Cash Flow
-$7,182
Cap Rate
2.2%
Cash-on-Cash Return
-17.0%
Debt Coverage Ratio
0.36
Internal Rate of Return (5 years)
-12.5%

Property Description


0.22 Acres Lot
Built in 2021
For Sale - Active
Units n/a

Timeless Elegance Meets Modern Comfort in Sought-After Tree Streets Welcome to this thoughtfully designed, custom-built residence in the coveted Tree Streets community of Winter Park. Boasting 4 bedrooms, 4.5 bathrooms, and over 3,300 square feet of meticulously curated living space, this one-of-a-kind home perfectly blends craftsmanship, comfort, and style. At the heart of the home, the chef-inspired kitchen showcases premium Thermador appliances, a gas range, and custom cabinetry that soars to 10-foot ceilings. The spacious butler’s pantry and built-in breakfast nook flow seamlessly into an inviting great room with custom built-ins—ideal for both everyday living and elegant entertaining. Nearby, the formal dining room features a striking drop ceiling, setting the stage for unforgettable gatherings. Designed for everyday convenience and privacy, the first floor includes both a comfortable guest suite and a luxurious primary suite, which features elegant wood beams accenting the ceiling and creates a warm, sophisticated retreat. Throughout the home, beautiful white oak floors add warmth and character, complementing the timeless design and enhancing the flow between each thoughtfully crafted space. Enjoy effortless indoor-outdoor living with an expansive covered lanai featuring a built-in summer kitchen and phantom screens, all overlooking a stunning pool and spa embraced by lush landscaping. A dedicated pool bath ensures convenience for guests enjoying the outdoor oasis. Inside, thoughtful features abound: a stylish mudroom with built-in storage, a large utility room with cabinetry and sink, and a conditioned mechanical room offering smart storage solutions. Upstairs, discover a spacious loft perfect for a media room or play area, accompanied by two generously sized bedrooms each with ensuite baths and ample closets. The Stratford-style front porch invites neighborly chats, while the private backyard provides a serene retreat. Designer-selected finishes and custom touches are evident throughout, highlighting the home's timeless elegance and modern functionality. Ideally situated just minutes from Park Avenue, residents will enjoy effortless access to fine dining, boutique shopping, charming cafes, museums, and the vibrant cultural heart of Winter Park. A rare offering that combines luxurious design, exceptional craftsmanship, and the warm character only a custom-built home can provide—this residence truly stands out in the Tree Streets.

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Location


Property Details


Parking

  • Description: Driveway, Garage Door Opener, Ground Level
  • Details: Attached
  • Garage Spaces: 2
  • Spaces Total: 0

Bedroom Information

  • # of Bedrooms: 4

Bathroom Information

  • # of Baths (Full): 4
  • # of Baths (Total): 5.0

Interior Features

  • # of Rooms: 8
  • # of Stories: 2

Exterior Features

  • Exterior Walls Materials: Stucco
  • Foundation: Slab
  • Roof Type: Gable or Hip
  • Roof Material: Metal, Shingle
  • Pool: Yes

Land Information

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

Lot Information

  • Parcel ID: 322130170802040
  • Lot Size: 9438 sqft

Property Information

  • Property Type: Single Family Residence
  • Year Built: 2021

Tax Information

  • Annual Tax: $18,024

Utilities

  • Water & Sewer: Public
  • Heating: Heat Pump
  • Cooling: Central Air

Location

  • County: Orange

Listing Details


Listed by:
Nick McKee
KELLER WILLIAMS WINTER PARK
(407) 913-0171

Source:
Stellar MLS
MLS#: O6331369
Stellar MLS

Investment Summary


Monthly Cash Flow
-$7,182
Cap Rate
2.2%
Cash-on-Cash Return
-17.0%
Debt Coverage Ratio
0.36
Internal Rate of Return (5 years)
-12.5%

Purchase Details

Find an Agent

Purchase price:
$2,199,999
Amount financed:
-$1,759,999
Down payment:
$440,000
Closing costs:
$66,000
Rehab costs:
$0
Initial cash invested:
$506,000
Square feet:
3,314
Cost per square foot:
$664
Monthly rent per square foot:
$2.44

Financing Details

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Loan amount:
$1,759,999
Loan to value ratio:
80.0%
Loan type:
Amortizing
Term:
30 years
Interest rate:
6.625%
Principal & interest:
$11,269
Property tax:
$1,502
Insurance:
$567
Private mortgage insurance (PMI):
$0
Monthly payment:
$13,338

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: (19%)
19%-$1,502-$18,025
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: (44%)
44%-$3,527-$42,325

Cash Flow


Monthly Yearly
Net operating income:
$4,087 $49,044
Mortgage payments:
-$11,269 -$135,228
Cash flow:
$7,182 $86,184