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321 Sylvan Boulevard, Winter Park, FL

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$1,395,000

($495/sqft)

List Status: Coming Soon
321 Sylvan Boulevard
Winter Park, FL 32789


3 beds
2 baths
2821 living sqft
Top Features
  • Subdivision: Sylvan Lake Shores
  • Built in  1940
  • Single Family Residence
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.
Property Details
Property Features
Property Sub Type
Single Family Residence
Pool
Screen Enclosure, Gunite, In Ground
County
Orange
Subdivision
SYLVAN LAKE SHORES
Additional Information
Additional Parcels YN
false
Alternate Key Folio Num
302205850602091
Appliances
Range, Refrigerator
Association YN
false
Attached Garage YN
false
Available For Lease YN
1
Bathrooms Total Integer
3
Building Area Source
Public Records
Building Area Total
3697
Building Area Total Srch SqM
343.46
Building Area Units
Square Feet
Calculated List Price By Calculated SqFt
494.51
Carport YN
false
Construction Materials
Frame
Cooling
Central Air
Country
US
Current Price
1395000.00
Direction Faces
East
Elementary School
Brookshire Elem
Exterior Features
Private Mailbox
Fireplace YN
true
Flood Zone Code
X
Flood Zone Date
2009-09-25
Flood Zone Panel
12095C0255F
Flooring
Carpet, Wood
Foundation Details
Concrete Perimeter
Furnished
Unfurnished
Garage Spaces
2
Garage YN
true
Heating
Central, Zoned
High School
Winter Park High
Homestead YN
1
Interior Features
Ceiling Fans(s)
Internet Address Display YN
true
Internet Automated Valuation Display YN
false
Internet Consumer Comment YN
false
Internet Entire Listing Display YN
true
Laundry Features
Laundry Room
Levels
One
List AOR
Orlando Regional
Living Area Meters
262.08
Living Area Source
Public Records
Living Area Units
Square Feet
Lot Size Acres
0.38
Lot Size Square Feet
16519
Lot Size Square Meters
1535
Middle Or Junior School
Glenridge Middle
Minimum Lease
No Minimum
Modification Timestamp
2026-06-17T16:27:10.348Z
New Construction YN
false
Occupant Type
Vacant
Ownership
Fee Simple
Parcel Number
05-22-30-8506-02-091
Patio And Porch Features
Front Porch, Rear Porch
Pool Private YN
true
Postal Code Plus 4
4047
Public Survey Range
30
Public Survey Section
05
RATIO Current Price By Calculated SqFt
494.51
Road Responsibility
Public Maintained Road
Road Surface Type
Brick
Roof
Shingle
Room Count
7
Senior Community YN
false
Sewer
Public Sewer
Showing Requirements
ShowingTime
Status Change Timestamp
2026-06-17T15:54:42.000Z
Stories Total
1
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
Total Acreage
1/4 to less than 1/2
Total Annual Fees
0.00
Total Monthly Fees
0.00
Township
22
Universal Property Id
US-12095-N-052230850602091-R-N
Unparsed Address
321 SYLVAN BLVD
Utilities
BB/HS Internet Available, Cable Available, Electricity Connected, Phone Available, Public, Sewer Connected, Water Connected
Water Source
Public
Waterfront YN
false
Zoning
R-1A
Neighborhood Map
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MLS #MFRO6417674 Listing courtesy of Premier Sothebys Int'l Realty provided by Stellar MLS.

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All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independent verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. The source of the listing data is as follows: Stellar MLS (updated 6/17/26 7:20 PM) |

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Wendy Morris LLC

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BK 3146762
16797 Broadwater Avenue
Winter Garden, Florida 34787

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