Property Description

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 cafés, 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.

Included Appliances

RangeRefrigerator

Property Details

Interior

Appliances

RangeRefrigerator

Bathrooms Total Decimal

2.5

Building Area Total

3697

Cooling

Central Air

Flooring

CarpetHardwood

Furnished

Unfurnished

Heating

CentralZoned

Interior Features

Ceiling Fan(s)

Laundry Features

Laundry Room

Living Area

2821

Rooms Total

7

Construction

Building Area Source

Public Records

Building Area Units

Square Feet

Construction Materials

Wood Frame

Direction Faces

East

Foundation Details

Concrete Perimeter

Levels

One

Living Area Source

Public Records

Living Area Units

Square Feet

Roof

Shingle

Stories Total

Yes

Year Built

1940

Site & Exterior

Covered Spaces

2

Exterior Features

Private Mailbox

Flood Zone Code

X

Garage Spaces

2

I D X Participation

Yes

Lot Size Acres

0.38

Lot Size Area

16519

Lot Size Square Feet

16519

Lot Size Units

Square Feet

Patio And Porch Features

Front PorchRear Porch

Pool Features

GuniteIn GroundScreen Enclosure

Public Survey Range

30

Public Survey Section

05

Road Responsibility

Public Maintained Road

Road Surface Type

Brick

Sewer

Public Sewer

Total Acreage

1/4 to less than 1/2

Utilities

BB/HS Internet AvailableCable AvailableElectricity ConnectedPhone AvailablePublicSewer ConnectedWater Connected

Water Source

Public

Zoning

R-1A

Financials

Calculated List Price By Calculated Sq Ft

494.51

Contract Status Change Date

2026-06-17

Current Price

1395000

Feed Types

BBO

Lease Considered

Yes

Minimum Lease

No Minimum

Owner Name

ROGER W SIMS

Ownership

Fee Simple

Parcel Number

052230850602091

Public Survey Township

22

Tax Annual Amount

6543.77

Tax Block

B

Tax Book Number

N-48

Tax Legal Description

SYLVAN LAKE SHORES N/48 THE S 1/2 OF LOT9 & LOT 10 & N 35 FT OF LOT 11 BLK B

Tax Lot

9

Tax Year

2025

Neighborhood & Lifestyle

Community & Association

M L S Area Major

32789 - Winter Park

Subdivision Name

SYLVAN LAKE SHORES

Schools

Ratings

Elementary

Brookshire Elem

Middle

Glenridge Middle

High

Winter Park High

Listing provided courtesy of STELLAR via IDX. Updated: Jun 25, 2026, 7:08am.

321 SYLVAN BOULEVARD

321 SYLVAN BOULEVARD

Property Description

Property Details

Interior

Construction

Site & Exterior

Financials

Neighborhood & Lifestyle

Community & Association

Schools

Mel Bernstein

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321 SYLVAN BOULEVARD

321 SYLVAN BOULEVARD

Property Description

Property Details

Interior

Construction

Site & Exterior

Financials

Neighborhood & Lifestyle

Community & Association

Schools

Mel Bernstein