321 SYLVAN BOULEVARD Winter Park, FL $ 1,395,000
321 SYLVAN BOULEVARD
$ 1,395,000
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321 SYLVAN BOULEVARD

Winter Park, FL, 32789
$ 1,395,000
Bedrooms3 Baths2.1 Sq 2,821

Monthly Estimate*

$ 8,589

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Single Family Home for sale in Winter Park, FL

for $1,395,000 with 3 bedrooms and 2 full baths, 1 half bath. This 2,821 square foot home was built in 1940 on a lot size of 0.38.

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.

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Single Family Coming Soon

Price

$ 1,395,000

Bedrooms

3

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 6,543

Style

Single Family Residence

Lot Size

0.38

Year Built

1940

Town/City

Winter Park

County/Region

Orange

MLS | Web ID

O6417674

Features
General
Sewer Public Sewer
Heating Central Zoned
Cooling Central Air
Utilities BB/HS Internet Available Cable Available Electricity Connected Phone Available Public Sewer Connected Water Connected
Roof Shingle
Appliances Range Refrigerator
Zoning R-1A
Garage Spaces 2
Patio/Porch Features Front Porch Rear Porch
Pool Features Gunite In Ground Screen Enclosure
Construction Materials Wood Frame
Year Built 1940
Levels One
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
County Orange
New Construction false
Property Type Residential
Attached Garage false
Subdivision Name SYLVAN LAKE SHORES
Facing Direction East
Garage Y/N true
Total Rooms 7
Full Baths 2
Status Coming Soon
Directions From Park Ave E on Aloma Ave R on Sylvan Blvd.
High School Winter Park High
City WINTER PARK
Senior Community Y/N false
MLS Area 32789 - Winter Park
Lot Size Units Square Feet
Lot Size Square Feet 16519
Carport Y/N false
Listing Terms Cash Conventional
Elementary School Brookshire Elem
Land Lease Y/N false
Tax Annual Amount 6543.77
Middle/Junior High School Glenridge Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Coming Soon
Occupancy Type Vacant
Tax Lot 9
Legal Description SYLVAN LAKE SHORES N/48 THE S 1/2 OF LOT9 & LOT 10 & N 35 FT OF LOT 11 BLK B
Minimum Lease No Minimum
Water Access Y/N false
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities Ceiling Fan(s)
Flooring Carpet Hardwood
Furnished Y/N Unfurnished
Total Stories 1
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 1
Laundry Features Laundry Room
Total Bedrooms 3
Total Baths 3
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Exterior
Exterior Amenities Private Mailbox
Water Source Public
Lot Size Area 16519
Foundation Details Concrete Perimeter
Building Area Total 3697
Lot Size Acres 0.38
Road Surface Type Brick
Private Pool true
Waterfront Y/N false
Covered Spaces 2
Road Responsibility Public Maintained Road
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* Excluded Features
List By
MEL@LuxuriousHomes.com

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Affordability Calculator

$9,135
Per Month
94%
6%
0%
Monthly Principal & Interest
$8,589
Monthly Property Taxes
$545
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% 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.
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Nearby
0 Elementary School
0 Middle School
Winter Park High High School High School
Pricing History
DatePricePrice ChangeDescription
6/17/2026$1,395,000 Listed Price

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321 SYLVAN BOULEVARD, Winter Park, FL, 32789 is a Single Family Home for sale at $1,395,000 with 2,821 sqft and a lot size of 0.38. 321 SYLVAN BOULEVARD has 3 bedrooms, 2.1 baths, and was built in 1940. The property's zip code is 32789 which is in Winter Park, FL