Skip to content
Property for sale at 255 STIRLING AVENUE, WINTER PARK, FL, 32789

255 Stirling AvenueWinter Park, FL, 32789

4beds
4baths
3,635sqft
Single Family Residence
Built in 1982
$2,835,000
Sold
Price per sqft
$780
Sold on
Nov 24, 2025
MLS #O6346603Updated Nov 25, 2025

About this property

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.

Interested in this property?
Gaby, Property Specialist
Speak to GabyProperty Specialist, SerhantGaby can share what this home sold for, and find you comparable properties still on the market.
+1 (407) 490-0475
No pressure. Your details stay private.

Property details

Property type
Single Family Residence
Street address
255 Stirling Avenue
City
Winter Park
State
FL
ZIP code
32789
Year built
1982
New construction
No
Faces
South
Rooms
9
Living area
3,635 sqft
Total building area
4,580 sqft
Levels
Two

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at October 8, 2026 at 8:01 AM EDT

Price & sale history

EventPrice
SoldMLS #O6346603$2,835,000
Price reducedMLS #O6346603$3,100,000Change: −6%−$199,000
Listed for saleMLS #O6346603$3,299,000
SoldMLS #O6093381$2,100,000
History may be incomplete.
Explore nearby sales

Location

Recent sales nearby

Property for sale at 255 STIRLING AVENUE, WINTER PARK, FL, 32789
Learn more about this propertyGet in touch for more information
We will use your details to respond to this request and may share them with a suitable real estate professional when needed. Marketing is optional.