by Global Lifestyle Properties

See Home Value
$1,300,000
● House - Off Market

321 SYLVAN BOULEVARD

WINTER PARK, FL 32789
bedrooms
3 Beds
bathrooms
2 Baths, 1 Half Bath
square feet
2,821 Ft²
$7,395
Est. Monthly

About This Property

Set on a rare double lot in one of Winter Park's most coveted locations, this charming 1940 Craftsman-style residence presents an extraordinary opportunity to enjoy one of Central Florida's most celebrated lifestyles while envisioning the future. Just moments from the Winter Park Chain of Lakes, the boutiques and acclaimed dining of Park Avenue, and the timeless beauty of Rollins College, the property offers a setting that few locations can rival.

The existing residence features approximately three bedrooms, two-and-a-half bathrooms, and generously proportioned living spaces filled with warmth and character. Lovingly maintained over the years, the home provides a comfortable foundation for renovation, restoration, or reimagination. Outdoors, a screened pool creates a private retreat for year-round enjoyment, while a detached two-car garage and separate studio shed offer exceptional flexibility for hobbies, creative pursuits, a home office, fitness space, or guest accommodations.

What truly distinguishes this offering is the double lot itself. Opportunities of this scale within the heart of Winter Park are increasingly rare, providing the space and flexibility to construct a custom estate tailored to your vision while preserving ample room for outdoor living, gardens, and recreation.

Life here extends far beyond the property lines. Enjoy morning walks beneath majestic oak canopies, afternoons on the Chain of Lakes, outdoor concerts, art festivals, sidewalk cafes, and some of Florida's most picturesque streetscapes. Whether renovating the existing residence or creating the home of your dreams, this exceptional property represents a rare chance to secure a legacy homesite in one of the most desirable addresses in Central Florida.
Unit Size
2,821 Ft²
Days on Market
22 days
Land Size
0.38 acres
Price per sqft
$495
Property Type
House
Property Taxes
$545
HOA Dues
-
Year Built
1940

Payment Calculator

Cap Rate Calculator

Last updated: 3 months ago (Stellar MLS #O6417674)

Price History

Date / Event Date Event Price
Jul 24, 2026 Sold
Sold
Jul 3, 2026 In contract -
In contract
Jun 17, 2026 Listed by PREMIER SOTHEBYS INT'L REALTY $1,395,000
Listed by PREMIER SOTHEBYS INT'L REALTY

Property Highlights

Air Conditioning
Fireplace

Building Info

Overview

    General

  • Year Built: 1940
  • Effective Year Built: 1970
  • Building Count: 1
  • Bedroom Count: 3
  • Bathroom Count: 3
  • Full Bathrooms: 2
  • Partial Bathrooms: 3
  • Building Condition: 2
  • Building Quality: 10
  • Construction Type: 0
  • Building Style: 0
  • Exterior Walls Type: 17
  • Interior Walls Type: 3
  • Roof Shape Type: 7
  • Roof Cover Type: 3
  • Floor Count: 100
  • Living Units: 1
  • Floor Cover: 15
  • Basement Type: 0
  • Basement Area: 0
  • Garage Type: 4
  • Garage Square Area: 690
  • Parking Space Count: 2
  • Patio Type: 55
  • Porch Type: 35
  • Pool Type: 8

    Dimensions

  • Lot Size Square Feet: 16,519
  • Total Building Area: 3,697
  • Gross Building Area: 3,697
  • Building Area: 2,800
  • Building Area Measurement: L

    Heating and Cooling

  • Fireplace Count: 1
  • Air Conditioning: 1
  • Heating: 4
  • Heated Square Feet: 2,800
  • Heating Fuel Type: 2

    Utilities

  • Sewer System: 0
  • Water Service: 0

Building

  • Building Type: 0
  • Property Class: R
  • Subdivision: SYLVAN LAKE SHORES
  • Land Acres: 0000000379
  • Standard Land Use Code: 1001
  • County Land Use Code: 0100
  • State Land Use Code: 001
  • Legal Description 1: SYLVAN LAKE SHORES N/48 THE S 1/2 OF LOT 9 & LOT 10 & N 35 FT OF LOT 11 BLK B

Neighborhood

  • School District Name: Orange County School District
  • Census Tract: 016002

Zoning

  • Zoning: R-1A

Geography

  • Assessors Map Reference: 205
  • Subdivision Tract Number: 8506
  • Parcel: 05-22-30-8506-02-091
  • Block: B
  • Lot: 9-11,
  • Meridian: SEC 05 TWN 22S RNG 30E
  • Municipality: WINTER PARK
  • Latitude: 28.5993
  • Longitude: -81.337

    Address

  • Full Address: 321 Sylvan Blvd
  • Address - House Number: 321
  • Address - Street Name: Sylvan
  • Address - Suffix Type: Blvd
  • State: FL
  • City Name: Winter Park
  • Carrier Code: C083
  • 4-Digit Zip Code: 4047
  • Zip Code: 32789

Valuation

    Tax

  • Total Area: 3,152
  • Tax Year: 2023
  • Tax Amount: $603,498
  • Tax Rate Code Area: 06-WP

    Appraisal Valuation

  • Standard Deviation: 0.154
  • Valuation Date: Jan 03, 2024
  • Confidence Score: 81
  • Final Value: 1,157,139
  • High Value: 1,335,435
  • Low Value: 978,843

    Market Valuation

  • Market Total Value: $786,767
  • Market Land Value: $400,000
  • Market Improvement Value: $386,767

    Assessments Valuation

  • Assessed Year: 2023
  • Assessed Total Value: $404,187
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


Similar Homes for Sale

Currently no similar homes around

Nearby Rentals

Unit for rent at 301 W Comstock Avenue, WINTER PARK, FL, 32789

$6,000 /mo

  • 2 Beds
  • 2 Baths
  • 1,500 ft²
301 W Comstock Avenue, WINTER PARK, FL, 32789 Listing by Sydney Brownlee
Unit for rent at 4230 Lower Park Road, ORLANDO, FL, 32814

$9,500 /mo

  • 5 Beds
  • 4 Baths
  • 4,018 ft²
4230 Lower Park Road, ORLANDO, FL, 32814 Listing by Meg Dolan
Unit for rent at 1760 Alabama Drive, WINTER PARK, FL, 32789

$9,500 /mo

  • 4 Beds
  • 2 Baths
  • 2,841 ft²
1760 Alabama Drive, WINTER PARK, FL, 32789 Listing by Drew Henner


Frequently Asked Questions

When was property at 321 Sylvan Boulevard built and last sold?
The property at 321 Sylvan Boulevard was built in 1940 and last sold on Jan 1, 1970 for $0.
How much is this home worth?
The estimated value of the home located at 321 Sylvan Boulevard is $1,410,760.
What are some comparable homes to 321 Sylvan Boulevard?
There are currently no comparable homes to 321 Sylvan Boulevard.