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321 Sylvan Boulevard

WINTER PARK, FL 32789
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Bed 3

Bed

Bath 3

Bath

SqFt2,821

Sqft

Acres0.38

Acre(Lot)

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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Detail Ic Property Details

Property Type : Residential

Price : $1,395,000

AD Id : 85051036

MLS Id : MFRO6417674

Beds : 3

Lot Size : 0.38 Acre

Living Area Size : 2,821

Year Built : 1940

Garage : 2

County : Orange

Subdivision: Sylvan Lake Shores

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Feature Features

  • Bedroom Information

    Total Bedroom: 3

    Bathroom Information

    Total Baths: 3 Full Baths: 2 Half Baths: 1

    Interior Features

    Ceiling Fans(s) Roof: Shingle Appliances: Range, Refrigerator Laundry Features: Laundry Room

    Roofing Information

    Shingle
  • Flooring Information

    Flooring: Carpet, Wood Construction Materials: Frame
  • Heating & Cooling

    Heating: Central, Zoned Cooling: Central Air WaterSource: Public

  • Building Information

    Year Built: 1940
  • Exterior Features

    Private Mailbox Construction Materials: Frame Foundation Details: Concrete Perimeter Road Responsibility: Public Maintained Road
  • Pool Features

    Private Pool: 1 Gunite, In Ground, Screen Enclosure

  • Lot Information

    Lot Square Feet: 16519 Lot Acres: 0.38 Lot Size (SqMt): 1535

    Property Information

    Property Type: Residential Sub Type: Single Family Residence

  • Tax Information

    Tax Block: B Tax Book Number: N-48 Tax Lot: 9 Tax Legal Description: SYLVAN LAKE SHORES N/48 THE S 1/2 OF LOT9 & LOT 10 & N 35 FT OF LOT 11 BLK B Annual Tax: $6543.77 Tax Year: 2025 Parcel Number: 05-22-30-8506-02-091

  • Garage Information

    Has Garage: Yes Garage Space: 2

  • School Information

    Elementary School: Brookshire Elem Junior High School: Glenridge Middle Senior High School: Winter Park High
  • Utility Information

    BB/HS Internet Available, Cable Available, Electricity Connected, Phone Available, Public, Sewer Connected, Water Connected Sewer: Public Sewer Water Source: Public
  • Location Information

    Subdivision: SYLVAN LAKE SHORES City: WINTER PARK Direction: From Park Ave, E on Aloma Ave, R on Sylvan Blvd.
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
2661 Via Tuscany, Winter Park, FL, 32789 $6,888,888 4 5 4,636 4,636 SqFt
Undisclosed Address, Winter Park, FL, 32789 $1,249,900 4 4 2,936 2,936 SqFt
1881 Lake Spier Drive, Winter Park, FL, 32789 $1,350,000 3 2 1,750 1,750 SqFt
1836 Whitehall Drive, Winter Park, FL, 32789 $3,500,000 5 7 4,168 4,168 SqFt
1864 Grinnell Terrace, Winter Park, FL, 32789 $1,599,000 5 4 3,028 3,028 SqFt
432 Worthington Drive, Winter Park, FL, 32789 $2,719,000 5 5 3,845 3,845 SqFt
1841 Lake Spier Drive, Winter Park, FL, 32789 $1,650,000 3 4 2,467 2,467 SqFt
1836 Grinnell Terrace, Winter Park, FL, 32789 $999,000 3 2 1,907 1,907 SqFt
1870 Walker Avenue, Winter Park, FL, 32789 $1,299,000 3 3 2,046 2,046 SqFt
1830 Edwin Boulevard, Winter Park, FL, 32789 $625,000 3 2 1,287 1,287 SqFt
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ByOwner last updated this listing 06/18/2026 @ 18:20

MLS: MFRMLS #O6417674 LISTED BY: Mel Bernstein, PREMIER SOTHEBYS INT'L REALTY 407-333-1900 SOURCE: MFRMLS (My Florida Regional MLS DBA Stellar MLS) (Listings courtesy of MFRMLS (My Florida Regional MLS DBA Stellar MLS) as distributed by MLS GRID)

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