Florida
Winter Park
255 STIRLING AVENUE

$3,299,000

255 STIRLING AVENUE, Winter Park, FL 32789

4 beds |
4 baths |
3,635 sqft

Single-Family Home
Built in 1982
0.32acre lot
2 car garage
$908/sqft
Listed 15 days ago

Property Description

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.

Listing Status:: Active
Date Added:: September 25, 2025 at 05:00AM
Listing Office:: PREMIER SOTHEBY'S INTL. REALTY : 407-644-3295
Listing Agent:: Alison Mosley : 407-304-6458
MLS ID:: O6346603

General: Ceiling Fan(s)Eating Space In KitchenHigh CeilingsPrimaryBedroom Upstairs
Appliances: DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Laundry: Inside
Flooring: CarpetTileHardwood
A/C: Central Air
Heating: Central
Fireplace: Living RoomFireplace

General: BalconyLightingPrivate MailboxRain Gutters
Pool: In Ground

Roofing: Shingle
General: Wood FrameTwoSlab

Road/Access: Paved
Originating MLS: Stellar MLS
County: Orange

Zoning: R-1AAAVIRGINIA HEIGHTS G/107 LOT 9 BLK H072230890808090
View: Water

Utilities: Public
Water: Public
Sewer: Public Sewer

Source: Stellar MLS

This listing courtesy of Alison Mosley, PREMIER SOTHEBY'S INTL. REALTY

Monthly Payment

$Est. Payment

Principal & Interest $
Property Taxes $
Home Insurance $
VA Funding Fee $

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Location

Schools Nearby

Audubon Park School

1500 Falcon Dr, Orlando, FL, 32803

Grades PK-8

1.38 miles away

Glenridge Middle School

2900 Upper Park Rd, Orlando, FL, 32814

Grades 6-8

1.07 miles away

Winter Park High School

2100 Summerfield Rd, Winter Park, FL, 32792

Grades 9-12

1.74 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.