1421 Sunset Dr

Off Market

1421 Sunset Dr

Winter Park FL 32789

1930 sq. ft.

5477 sq. ft.

Single-Family

Last sold for $825,000

Sarah Tomlinson, last sold this property on 15 September 2025 after 47 days on market.

Overview

BUYER GOT COLD FEET= YOUR OPPORTUNITY! Welcome to 1421 Sunset Drive – A Turnkey Gem in the Heart of Olde Winter Park! This is a rare opportunity to own a beautifully updated home on one of Olde Winter Park’s most charming, brick-lined, tree-canopied streets. Just steps from serene Lake Knowles and Lake Wilbar, and minutes from the vibrant dining, shopping, and cultural experiences of Park Avenue, this 3-bedroom, 3.5-bathroom residence offers the perfect blend of classic charm and modern convenience. Enjoy a low-maintenance lifestyle with eco-friendly landscaping and a thoughtfully designed floor plan featuring two spacious primary suites — one upstairs and one down — each with its own updated bathroom. Inside, the home boasts tall vaulted ceilings, warm wood plank LVT flooring, a cozy wood-burning fireplace, and multiple inviting living areas. The kitchen is a standout with sleek cabinetry, granite countertops, and stainless steel appliances, ideal for both daily living and entertaining. Step outside to enjoy Trex decking on both front and rear patios, a fenced backyard for privacy, and a convenient laundry/mudroom entry from the garage. Additional highlights include a standing seam metal roof, attached garage, and access to top-rated Winter Park schools. The home is also located near the YMCA, Interlachen Country Club, Winter Park Racquet Club, Rollins College, UCF, and AdventHealth Winter Park. This home is move-in ready and offers the very best of Winter Park living — schedule your private showing today!

Features

3 bedrooms

4 bathrooms

1 carspace

1 garage space

1930 sq. ft. floor area

5477 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 1421 Sunset Dr is $699k.

Median value

$699k

Estimated value range

$292k - $5.22m

Median days on market

Estimated value trend

-7%

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 1421 Sunset Dr

2025

Sold

$825,000

15 Sep 2025 by Sarah Tomlinson, of COMPASS FLORIDA LLC

2022

Sold

$650,000

16 Sep 2022 by Mick Night, of PREMIER SOTHEBY'S INTL. REALTY

2020

Sold

$469,900

26 Mar 2020 by Lisa Gould, of KELLER WILLIAMS WINTER PARK

Happy sellers in Winter Park

83%

83% 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, 96 three-bedroom single-family properties similar to 1421 Sunset Dr, have been sold.

This represents a 11% 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

(204 reviews)

Get a market analysis

Justin Adams

(145 reviews)

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Andrew Livingston

at Coldwell Banker Realty - Winter Park

(16 reviews)

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Jennifer King

at CORCORAN PREMIER REALTY

(6 reviews)

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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