Date
Details
Price
Change
Source
7/02/2026
Listed
$1,395,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$1,395,000 Just Listed
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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.
Full Property Details
Full Property Details for 321 Sylvan Blvd
General
- Price: $1,395,000
- Taxes: $6,543 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6417674
- Updated: Today (7/2/2026)
- Added to Site: Today
Rental Information
- Min. Lease: No Minimum
Interior
- Number of Rooms: 7
- Interior Features: Ceiling Fan(s)
- Fireplace: Yes
- Appliances: Range, Refrigerator
- Furnishings: Unfurnished
- Flooring: Carpet, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Laundry Room
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Gunite, In Ground, Screen Enclosure
Exterior
- Exterior Features: Private Mailbox
- Deck/Patio: Front Porch, Rear Porch
- Porch/Patio/Deck: Front Porch, Rear Porch
Parking
- Garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
Location
- Area: 32789 - Winter Park
- County: Orange
- Development Name: 32789 - Winter Park
- Subdivision: SYLVAN LAKE SHORES
- Driving Directions: From Park Ave, E on Aloma Ave, R on Sylvan Blvd.
- Direction Faces: East
School Information
- Elementary School: Brookshire Elem
- Middle School: Glenridge Middle
- High School: Winter Park High
Community
- Community Name: 32789 - Winter Park
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Zoned
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Phone Available, Public, Sewer Connected, Water Connected
Structural Information
- Exterior Const.: Wood Frame
- Roof: Shingle
- Stories/Levels: One
- Square Feet: 2,821
- Sq. Ft. Source: Public Records
- Year Built: 1940
Lot Features
- Lot Size (Acres): 0.38
- Lot Size (Sq. Ft.): 16,519
- Lot Size: 16519
- Street/Road Desc.: Brick
Financial Considerations
- Tax Amount: $6,543.77
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: SYLVAN LAKE SHORES N/48 THE S 1/2 OF LOT9 & LOT 10 & N 35 FT OF LOT 11 BLK B
- Flood Zone Info: X
- APN: 52230850602091
- Property ID: 52230850602091
- Block/Lot/Section: B
Listed by Premier Sothebys Int'l Realty
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Listing agents
— 321 Sylvan Blvd —
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Schools
Schools serving 321 Sylvan Blvd
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Brookshire Elementary School 2500 Cady Way, Winter Park, FL 32792 | PK-5 | 1.2 mi |
Glenridge Middle School 2900 Upper Park Road, Orlando, FL 32814 | 6-8 | 1.5 mi |
Winter Park High School 2100 Summerfield Road, Winter Park, FL 32792 | 9-12 | 1.3 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 321 Sylvan Blvd
Tax History
Tax History for 321 Sylvan Blvd
Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,544
4%
$439,952
6%
2024
$6,304
4%
$416,313
3%
2023
$6,035
12%
$404,187
6%
2021
$5,389
-1%
$380,985
-3%
2022
$5,452
1%
$392,415
4%
2021
$5,389
1%
$375,725
2%
2019
$5,354
1%
$367,278
2%
2018
$5,322
1%
$360,430
2%
2017
$5,272
2%
$353,017
2%
2016
$5,163
-2%
$345,756
1%
2015
$5,287
-1%
$343,353
1%
2014
$5,332
2%
$340,628
2%
2013
$5,215
—
$335,594
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 321 Sylvan Blvd
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Sold by Premier Sotheby's Intl. Realty
321 Sylvan Boulevard, Winter Park, FL 32789 (MLS# O6417674) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 321 Sylvan Boulevard is currently listed for $1,395,000 and was received on July 02, 2026. Want to learn more about 321 Sylvan Boulevard? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.