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$2,835,000

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,635 Sq. Ft.
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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.

Full Property Details for 255 Stirling Ave

General

  • Sold For: $2,835,000
  • Taxes: $32,331 (2025)
  • Status: Closed
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6346603
  • Added to Site: 112 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 9
  • Interior Features: Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, PrimaryBedroom Upstairs
  • Fireplace: Yes
  • Fireplace(s): Living Room
  • Appliances: Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
  • Flooring: Carpet, Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Inside

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground

Exterior

  • Exterior Features: Balcony, Lighting, Private Mailbox, Rain Gutters

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 32789 - Winter Park
  • County: Orange
  • Development Name: 32789 - Winter Park
  • Subdivision: VIRGINIA HEIGHTS
  • Driving Directions: Park Avenue Winter Park into Rollins right on Holt left on French to lakeview left on Stirling house on left
  • Direction Faces: South

School Information

  • Elementary School: Audubon Park K8
  • Middle School: Audubon Park K-8
  • High School: Winter Park High

Community

  • Community Name: 32789 - Winter Park

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water District: LAKE VIRGINIA
  • Water: Public
  • Utility Description: Public

Structural Information

  • Exterior Const.: Wood Frame
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 3,635
  • Sq. Ft. Source: Public Records
  • Living Area: 3,635 Sq. Ft.
  • Year Built: 1982

Lot Features

  • Property View: Water
  • Lot Size (Acres): 0.32
  • Lot Size (Sq. Ft.): 13,312
  • Lot Size: 13312
  • Street/Road Desc.: Paved

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Access: Yes
  • Water Access Desc: Lake, Lake - Chain of Lakes
  • Water Extras: Yes
  • Water Front Name: LAKE VIRGINIA
  • Water Front Desc.: Lake Front, Lake - Chain of Lakes

Financial Considerations

  • Tax Amount: $32,331
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: VIRGINIA HEIGHTS G/107 LOT 9 BLK H
  • Flood Zone Info: AE
  • APN: 72230890808090
  • Property ID: 72230890808090
  • Block/Lot/Section: H

Meet the selling agent

Meet the selling agent
— 255 Stirling Ave —

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 255 Stirling Ave

School District:Orange County School District
NameGradesDistance
Audubon Park School
1500 Falcon Drive, Orlando, FL 32803
PK-81.4 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 255 Stirling Ave

Date
Details
Price
Change
Source
11/24/2025
Sold
$2,835,000
-8.55%
MLS
10/17/2025
Price Reduced
$3,100,000
-6.03%
MLS
9/25/2025
Listed
$3,299,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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255 Stirling Avenue, Winter Park, FL 32789 (MLS# O6346603) is a Single Family property that was sold at $2,835,000 on November 24, 2025. This property was sold by Ruthie Harris from our Winter Park Office.Want to learn more about 255 Stirling Avenue? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.