1752 CHESTNUT AVENUE Winter Park, FL $ 1,995,000
1752 CHESTNUT AVENUE
$ 1,995,000
Share Save

1752 CHESTNUT AVENUE

Winter Park, FL, 32789
$ 1,995,000
Bedrooms4 Baths4.1 Sq 3,314

Monthly Estimate*

$ 12,446

1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 1
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 2
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 3
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 4
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 5
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 6
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 7
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 8
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 9
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 10
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 11
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 12
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 13
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 14
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 15
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 16
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 17
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 18
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 19
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 20
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 21
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 22
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 23
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 24
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 25
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 26
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 27
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 28
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 29
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 30
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 31
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 32
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 33
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 34
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 35
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 36
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 37
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 38
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 39
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 40
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 41
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 42
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 43
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 44
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 45
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 46
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 47
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 48
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 49
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 50
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 51
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 52
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 53
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 54
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 55
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 56
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 57
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 58
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 59
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 60
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 61
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 62
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 63
1752 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 64
View a Virtual Tour

Single Family Home for sale in Winter Park, FL

for $1,995,000 with 4 bedrooms and 4 full baths, 1 half bath. This 3,314 square foot home was built in 2021 on a lot size of 0.22.

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.

See more

Single Family Pending

Price

$ 1,995,000

Bedrooms

4

Full Bath

4

Half Bath

1

Property Type

Single Family

Taxes

$ 18,024

Style

Single Family Residence

Lot Size

0.22

Year Built

2021

Town/City

Winter Park

County/Region

Orange

MLS | Web ID

O6331369

Features
General
Sewer Public Sewer
Heating Heat Pump
Cooling Central Air
Utilities BB/HS Internet Available Cable Available Electricity Connected Phone Available Public Sewer Connected Street Lights Water Connected
Roof Metal Shingle
Appliances Convection Oven Dishwasher Disposal Exhaust Fan Microwave Range Range Hood Refrigerator Tankless Water Heater Wine Refrigerator
Zoning R-1A
Garage Spaces 2
Pool Features Heated In Ground Lighting
Construction Materials Block Brick Stucco
Year Built 2021
Levels Two
Property Subtype Single Family Residence
Tax Year 2024
Ownership Fee Simple
County Orange
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name CONWILL ESTATES
Facing Direction North
Garage Y/N true
Total Rooms 8
Full Baths 4
Status Pending
Directions From Aloma Avenue head North on Phelps Avenue. Follow Phelps to Chestnut Avenue turn right on Chestnut Avenue the house is ahead on the right.
City WINTER PARK
Senior Community Y/N false
MLS Area 32789 - Winter Park
Lot Size Units Square Feet
Lot Size Square Feet 9438
Carport Y/N false
Listing Terms Cash Conventional VA Loan
Spa Features Heated In Ground
Land Lease Y/N false
Tax Annual Amount 18024.79
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/O6331369
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Pending
Occupancy Type Owner
Tax Lot 4
Legal Description CONWILL ESTATES S/13 LOT 4 BLK B
Minimum Lease No Minimum
Water Access Y/N false
Water View Y/N false
Flood Zone Code X
See more
Interior
Interior Amenities Built-in Features Crown Molding High Ceilings Open Floorplan Primary Bedroom Main Floor Solid Wood Cabinets Split Bedroom Stone Counters Thermostat Walk-In Closet(s)
Flooring Engineered Hardwood Tile
Total Stories 2
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N false
Half Baths 1
Laundry Features Laundry Room
Total Bedrooms 4
Total Baths 5
See more
Exterior
Exterior Amenities Irrigation System Lighting Outdoor Kitchen Outdoor Shower Rain Gutters Sliding Doors
Water Source Public
Lot Size Area 9438
Foundation Details Slab
Spa true
Building Area Total 4286
Lot Size Acres 0.22
Road Surface Type Asphalt
Private Pool true
Waterfront Y/N false
Covered Spaces 2
See more
* Excluded Features
List By
Keller Williams Winter Park

Broker

nickmckee@kw.com

Email

Affordability Calculator

$13,948
Per Month
89%
11%
0%
Monthly Principal & Interest
$12,446
Monthly Property Taxes
$1,502
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
4827338 Elementary School
4827337 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
12/19/2025$1,995,000 Listed Price

Map


See all

1752 CHESTNUT AVENUE, Winter Park, FL, 32789 is a Single Family Home for sale at $1,995,000 with 3,314 sqft and a lot size of 0.22. 1752 CHESTNUT AVENUE has 4 bedrooms, 4.1 baths, and was built in 2021. The property's zip code is 32789 which is in Winter Park, FL