by Global Lifestyle Properties

See Home Value
$2,835,000
● House - Off Market

255 STIRLING AVENUE

WINTER PARK, FL 32789
bedrooms
4 Beds
bathrooms
3 Baths, 1 Half Bath
square feet
3,635 Ft²
$17,916
Est. Monthly
0.44%
Cap Rate

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.
Unit Size
3,635 Ft²
Days on Market
60 days
Land Size
0.32 acres
Price per sqft
$853
Property Type
House
Property Taxes
$2,694
HOA Dues
-
Year Built
1982

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Last updated: 12 months ago (Stellar MLS #O6346603)

Price History

Date / Event Date Event Price
Nov 24, 2025 Sold
Sold
Oct 25, 2025 In contract -
In contract
Oct 17, 2025 Price Decreased $3,100,000
↓ $199K (6%)
Price Decreased
Sep 25, 2025 Listed by PREMIER SOTHEBY'S INTL. REALTY $3,299,000
Listed by PREMIER SOTHEBY'S INTL. REALTY
May 30, 2023 Sold
Sold
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Property Highlights

Garage
Air Conditioning
Fireplace
With View

Building Info

Overview

    General

  • Year Built: 1982
  • Effective Year Built: 1982
  • Building Count: 1
  • Bedroom Count: 4
  • Bathroom Count: 4
  • Full Bathrooms: 3
  • Partial Bathrooms: 4
  • Building Condition: 6
  • Building Quality: 13
  • Construction Type: 0
  • Building Style: 0
  • Exterior Walls Type: 17
  • Interior Walls Type: 3
  • Roof Shape Type: 7
  • Roof Cover Type: 3
  • Floor Count: 200
  • Living Units: 1
  • Floor Cover: 9
  • Basement Type: 0
  • Basement Area: 0
  • Garage Type: 1
  • Garage Square Area: 506
  • Parking Space Count: 2
  • Patio Type: 5
  • Porch Type: 126
  • Pool Type: 8

    Dimensions

  • Lot Size Square Feet: 13,848
  • Total Building Area: 4,580
  • Gross Building Area: 4,580
  • Building Area: 3,364
  • Building Area Measurement: L

    Heating and Cooling

  • Fireplace Count: 1
  • Air Conditioning: 1
  • Heating: 4
  • Heated Square Feet: 3,364
  • Heating Fuel Type: 3

    Utilities

  • Sewer System: 0
  • Water Service: 0

Building

  • Building Type: 0
  • Property Class: R
  • Subdivision: VIRGINIA HGTS
  • Land Acres: 0000000318
  • Standard Land Use Code: 1001
  • County Land Use Code: 0130
  • State Land Use Code: 001
  • Legal Description 1: VIRGINIA HEIGHTS G/107 LOT 9 BLK H

Neighborhood

  • School District Name: Orange County School District
  • Census Tract: 016100

Zoning

  • Zoning: R-1AAA

Geography

  • Assessors Map Reference: 204
  • Subdivision Tract Number: 8908
  • Parcel: 07-22-30-8908-08-090
  • Block: H
  • Lot: 9
  • Meridian: SEC 07 TWN 22S RNG 30E
  • Municipality: WINTER PARK
  • Latitude: 28.5863
  • Longitude: -81.3509

    Address

  • Full Address: 255 Stirling Ave
  • Address - House Number: 255
  • Address - Street Name: Stirling
  • Address - Suffix Type: Ave
  • State: FL
  • City Name: Winter Park
  • Carrier Code: C019
  • 4-Digit Zip Code: 5746
  • Zip Code: 32789

Valuation

    Tax

  • Total Area: 3,648
  • Tax Year: 2023
  • Tax Amount: $1,224,679
  • Tax Rate Code Area: 06-WP

    Appraisal Valuation

  • Standard Deviation: 0.1571
  • Valuation Date: Jan 03, 2024
  • Confidence Score: 80
  • Final Value: 2,105,190
  • High Value: 2,436,047
  • Low Value: 1,774,332

    Market Valuation

  • Market Total Value: $2,033,595
  • Market Land Value: $1,300,000
  • Market Improvement Value: $733,595

    Assessments Valuation

  • Assessed Year: 2023
  • Assessed Total Value: $822,062

    Sales

  • Current Sale Contract Date: May 26, 2023
  • Current Sale Recording Date: May 30, 2023
  • Current Sale Price:
  • Current Sale Document Type: 71
  • Current Sale Input Document Number: 300751
Data used for valuation calculations is provided by RealtyHop, and other third party sources

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

About Winter Park


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Unit for rent at 739 Minnesota Avenue, WINTER PARK, FL, 32789

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739 Minnesota Avenue, WINTER PARK, FL, 32789 Listing by Marilyn Kuczynski
Unit for rent at 432 W Swoope Avenue, WINTER PARK, FL, 32789

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432 W Swoope Avenue, WINTER PARK, FL, 32789 Listing by Edward Bonner


Frequently Asked Questions

When was property at 255 Stirling Avenue built and last sold?
The property at 255 Stirling Avenue was built in 1982 and last sold on May 26, 2023 for $2,100,000.
How much is this home worth?
The estimated value of the home located at 255 Stirling Avenue is $0.
What are some comparable homes to 255 Stirling Avenue?
There are currently no comparable homes to 255 Stirling Avenue.