by Global Lifestyle Properties

See Home Value
$1,875,000
● House - Off Market

1752 CHESTNUT AVENUE

WINTER PARK, FL 32789
bedrooms
4 Beds
bathrooms
4 Baths, 1 Half Bath
square feet
3,314 Ft²
$11,298
Est. Monthly
0.78%
Cap Rate

About This Property

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.
Unit Size
3,314 Ft²
Days on Market
154 days
Land Size
0.22 acres
Price per sqft
$602
Property Type
House
Property Taxes
$1,502
HOA Dues
-
Year Built
1957

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Last updated: 10 months ago (Stellar MLS #O6331369)

Price History

Date / Event Date Event Price
Jan 1, 2026 Sold
Sold
Oct 29, 2025 Price Decreased $1,995,000
↓ $104K (5%)
Price Decreased
Sep 24, 2025 Price Decreased $2,099,000
↓ $101K (4.6%)
Price Decreased
Jul 31, 2025 Listed by KELLER WILLIAMS WINTER PARK $2,199,999
Listed by KELLER WILLIAMS WINTER PARK
Dec 8, 2021 Sold
Sold
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Property Highlights

Garage
Air Conditioning

Building Info

Overview

    General

  • Year Built: 1957
  • Effective Year Built: 1960
  • Building Count: 2
  • Bedroom Count: 4
  • Bathroom Count: 5
  • Full Bathrooms: 4
  • Partial Bathrooms: 5
  • Building Condition: 1
  • Building Quality: 1
  • Construction Type: 0
  • Building Style: 0
  • Exterior Walls Type: 7
  • Interior Walls Type: 6
  • Roof Shape Type: 7
  • Roof Cover Type: 3
  • Floor Count: 200
  • Living Units: 1
  • Floor Cover: 15
  • Basement Type: 0
  • Basement Area: 0
  • Garage Type: 1
  • Garage Square Area: 462
  • Parking Space Count: 1
  • Patio Type: 55
  • Porch Type: 126
  • Pool Type: 0

    Dimensions

  • Lot Size Square Feet: 9,438
  • Total Building Area: 4,206
  • Gross Building Area: 4,206
  • Building Area: 3,090
  • Building Area Measurement: L

    Heating and Cooling

  • Air Conditioning: 1
  • Heating: 4
  • Heated Square Feet: 3,090
  • Heating Fuel Type: 2

    Utilities

  • Sewer System: 0
  • Water Service: 0

Building

  • Building Type: 0
  • Property Class: R
  • Subdivision: CONWILL ESTS
  • Land Acres: 0000000217
  • Standard Land Use Code: 1001
  • County Land Use Code: 0104
  • State Land Use Code: 001
  • Legal Description 1: CONWILL ESTATES S/13 LOT 4 BLK B

Neighborhood

  • School District Name: Orange County School District
  • Census Tract: 015802

Zoning

  • Zoning: R-1A

Geography

  • Assessors Map Reference: 202
  • Subdivision Tract Number: 1708
  • Parcel: 32-21-30-1708-02-040
  • Block: B
  • Lot: 4
  • Meridian: SEC 32 TWN 21S RNG 30E
  • Municipality: WINTER PARK
  • Latitude: 28.6134
  • Longitude: -81.3293

    Address

  • Full Address: 1752 Chestnut Ave
  • Address - House Number: 1752
  • Address - Street Name: Chestnut
  • Address - Suffix Type: Ave
  • State: FL
  • City Name: Winter Park
  • Carrier Code: C083
  • 4-Digit Zip Code: 1610
  • Zip Code: 32789

Valuation

    Tax

  • Total Area: 3,429
  • Tax Year: 2023
  • Tax Amount: $1,740,911
  • Tax Rate Code Area: 06-WP

    Appraisal Valuation

  • Standard Deviation: 0.1706
  • Valuation Date: Jan 03, 2024
  • Confidence Score: 78
  • Final Value: 1,561,959
  • High Value: 1,828,489
  • Low Value: 1,295,429

    Market Valuation

  • Market Total Value: $1,287,506
  • Market Land Value: $320,000
  • Market Improvement Value: $967,506

    Assessments Valuation

  • Assessed Year: 2023
  • Assessed Total Value: $1,151,250

    Sales

  • Current Sale Contract Date: Dec 03, 2021
  • Current Sale Recording Date: Dec 08, 2021
  • Current Sale Price:
  • Current Sale Document Type: 71
  • Current Sale Input Document Number: 20210749745
  • Previous Sale Recording Date: Apr 23, 2020
  • Previous Sale Contract Date: Apr 20, 2020
  • Previous Sale Amount: $365,000
  • Previous Sale Document Type: 71
Data used for valuation calculations is provided by RealtyHop, and other third party sources

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

About Winter Park


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Frequently Asked Questions

When was property at 1752 Chestnut Avenue built and last sold?
The property at 1752 Chestnut Avenue was built in 1957 and last sold on Dec 3, 2021 for $1,365,000.
How much is this home worth?
The estimated value of the home located at 1752 Chestnut Avenue is $0.
What are some comparable homes to 1752 Chestnut Avenue?
There are currently no comparable homes to 1752 Chestnut Avenue.