321 Sylvan Boulevard

Off Market

321 Sylvan Boulevard

Winter Park FL 32789

3697 sq. ft.

16519 sq. ft.

Single-Family

Last sold for $1,300,000

Mel Bernstein, last sold this property on 24 July 2026 after 22 days on market.

Overview

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.

Features

3 bedrooms

3 bathrooms

2 carspaces

2 garage spaces

3697 sq. ft. floor area

16519 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Winter Park over the last 12 months, the estimated median property value of 321 Sylvan Boulevard is $638.75k.

Median value

$638.75k

Estimated value range

$287.5k - $2.88m

Median days on market

Estimated value trend

-15%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Winter Park. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 321 Sylvan Boulevard

2026

Sold

$1,300,000

24 Jul 2026 by Mel Bernstein, of PREMIER SOTHEBYS INT'L REALTY

Happy sellers in Winter Park

80%

80% of sellers in Winter Park reported that their sale price either exceeded or met their price expectations.

Winter Park stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 7 reviews in Winter Park over the last 12 months.

Local market activity for 3 bedroom single-family properties in Winter Park

In the last 12 months, 111 three-bedroom single-family properties similar to 321 Sylvan Boulevard, have been sold.

This represents a 15% increase in three-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Winter Park for a market analysis.

Lisa Gould

at KELLER WILLIAMS WINTER PARK

(208 reviews)

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Andrew Livingston

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Jennifer King

at CORCORAN PREMIER REALTY

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Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Winter Park

Lisa Gould

Sellers who recommend Lisa Gould have praised them for being local expert, clear communication, supportive, responsive, patient, reliable, and empathetic