An incredible Winter Park Chain-of-Lakes opportunity on Lake Virginia with clear views of Rollins College. This transitionally designed home, situated in the highly coveted Virginia Heights, offers an opportunity like no other with proximity to Park Avenue coupled with the lakefront amenities through a Venetian canal system that uniquely connects five lakes and captures the quintessential Winter Park lifestyle. This four-bedroom three-and-a-half-bath home invites you into a two-story foyer surrounded by windows and natural light. The spacious kitchen features a mid-century tile backsplash, light cabinetry and a window out to the pool and lake. The main living space features a beautiful fireplace and back atrium that invites the stars and twinkling sunsets from the water. The separate dining room is spacious and there is an additional den or office space to round out the first floor. All bedrooms are upstairs and generously sized providing flexibility and the primary bedroom has the most incredible lakefront views. A clear water canal runs alongside the home and spills into lake Virginia adding to the ambiance of the backyard where nature abounds. Continue the existing renovation with your own style or build a house of your dreams. Impeccably located with shopping and dining at your fingertips as well as Rollins College. Fantastic schools with Audubon K-8 and Winter Park High. Don’t miss this one – call for your private tour.
Single-familyProperty Type
1982Year Built
0.31 acresLot Size
$1,077Est. Price/Sq.Ft.
2 car garageParking
Listed by Alison Mosley• PREMIER SOTHEBY'S INTL. REALTY
Listed by Frank Mosley• PREMIER SOTHEBY'S INTL. REALTY
* * MULTIPLE OFFERS HIGHEST AND BEST DUE BY MONDAY, MARCH 13, 2023 12PM NOON * * Here is your opportunity to live on the Winter Park Chain of Lakes and only a five minute stroll from the Park Avenue shopping and dining district. Located on Lake Virginia, the home is North facing with amazing views of Rollins College and the chapel. Currently, the home is two stories with over 3600 square feet of living space and already has a pool! Renovate the existing structure or start over and build the home of your dreams - the opportunities are abundant.
Public Records
Nov 1, 1988
Sold
$590,000
$162/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$32,331 (+3.3%)
$1,300,000 + $825,230
$2,125,230
2024
$31,307 (+155.6%)
$1,300,000 + $825,230
$2,125,230
2023
$12,247 (+4.5%)
$1,300,000 + $756,689
$2,056,689
2022
$11,721 (+1.0%)
2021
$11,601 (+3.9%)
2020
$11,163 (−3.3%)
2019
$11,550 (+0.5%)
2018
$11,492 (+0.8%)
2017
$11,397 (+2.1%)
2016
$11,168 (−2.3%)
2015
$11,436 (−0.9%)
2014
$11,535 (+2.1%)
2013
$11,296 (+1.0%)
2012
$11,183
Tax history for 255 Stirling Ave
Year
Property tax
Land + Additions
Assessment*
2025
$32,331 (+3.3%)
$1,300,000 + $825,230
$2,125,230
2024
$31,307 (+155.6%)
$1,300,000 + $825,230
$2,125,230
2023
$12,247 (+4.5%)
$1,300,000 + $756,689
$2,056,689
2022
$11,721 (+1.0%)
2021
$11,601 (+3.9%)
2020
$11,163 (−3.3%)
2019
$11,550 (+0.5%)
2018
$11,492 (+0.8%)
2017
$11,397 (+2.1%)
2016
$11,168 (−2.3%)
2015
$11,436 (−0.9%)
2014
$11,535 (+2.1%)
2013
$11,296 (+1.0%)
2012
$11,183
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Public record
Zoning
Permits
Beds
4
Baths
4
Stories
2
Lot width
—
Lot depth
—
Lot size
0.32 Acres
Year renovated
1982
Sq. Ft.
3,635
Year built
1982
Style
Single Family Residential
County
Orange County
APN
302207890808090
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 17, 2026.
R-1AAA
\N
Residential District
These districts are established within the city to provide areas for single-family dwellings and necessary accessory buildings. The regulations enumerated for this district are designed to encourage and promote the construction of and the continued use of the land for single-family dwellings, to promote and encourage a suitable environment for family life, to prohibit uses of the land which would substantially interfere with development or continuation of single-family dwellings in the districts, and to prevent use of the land for purposes which would overburden the public facilities. For lakefront properties, the regulations enumerated in this section are designed to encourage and promote the construction of residential uses in a manner which minimizes the impacts on the lakes, which are among the city's greatest assets; thus, diminishing their water quality and aesthetic appeal. Permitted as conditional uses within these districts will be certain structures and uses required to serve the residents such as public schools, churches and noncommercial recreational uses. Areas zoned for R-1AAA districts shall be those existing low-density residential areas plus certain undeveloped areas which should develop in a similar manner according to the comprehensive plan.
Permitted uses
Include but are not limited to:
Housing-Single unit
Feb 13, 2026 • Final
Residential roof
Roofing
Mar 10, 2025 • Final
Residential boathouse/dock
Construct a new dock and boathouse.
Addition
Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.
Property details
Parking
Parking Information
Garage Spaces: 2
Has Attached Garage
Has Garage
Interior
Virtual Tour
Bedroom Information
# of Bedrooms: 4
Bathroom Information
# of Full Baths (Total): 3
# of Half Baths (Total): 1
Laundry Room Information
Laundry Features: Inside
Other Rooms Information
# of Rooms: 9
Fireplace Information
Has Fireplace
Fireplace Features: Living Room
Heating & Cooling
Heating Information: Central
Cooling Information: Central Air
Interior Features
Interior Features: Ceiling Fans(s), Eat-in Kitchen, High Ceilings