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.
Sold for $2,835,000
$2,835,000
255 Stirling Ave, Winter Park, FL 32789
4beds
3,635sqft
Single Family Residence
Built in 1982
0.31 Acres Lot
$2,859,900 Zestimate®
$780/sqft
$5,098 Estimated rent
Home value
$2,859,900
$2.60M - $3.15M
$5,098/mo
Zestimate® history
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List your homeWhat's special
Beautiful fireplaceIncredible lakefront viewsClear water canalNature aboundsVenetian canal systemLakefront amenitiesSpacious kitchen
Zillow last checked:
Listing updated:
Listed by:
Alison Mosley 407-304-6458,
PREMIER SOTHEBY'S INTL. REALTY 407-644-3295,
Frank Mosley 407-489-9508,
PREMIER SOTHEBY'S INTL. REALTY
Bought with:
Ruth Harris, 3057893
COLDWELL BANKER REALTY
Source: Stellar MLS,MLS#: O6346603
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Primary bedroom
- Features: Built-in Closet
- Level: Second
Bedroom 3
- Features: Built-in Closet
- Level: Second
Bedroom 4
- Features: Built-in Closet
- Level: Second
Bathroom 2
- Features: Walk-In Closet(s)
- Level: Second
Den
- Level: First
Dining room
- Level: First
Foyer
- Features: Coat Closet
- Level: First
Kitchen
- Level: First
Living room
- Level: First
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
- Laundry: Inside
Features
- Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, PrimaryBedroom Upstairs
- Flooring: Carpet, Tile, Hardwood
- Has fireplace: Yes
- Fireplace features: Living Room
Interior area
- Total structure area: 4,580
- Total interior livable area: 3,635 sqft
Property
Parking
- Total spaces: 2
- Parking features: Garage - Attached
- Attached garage spaces: 2
Features
- Levels: Two
- Stories: 2
- Exterior features: Balcony, Lighting, Private Mailbox, Rain Gutters
- Has private pool: Yes
- Pool features: In Ground
- Has view: Yes
- View description: Water, Lake
- Has water view: Yes
- Water view: Water,Lake
- Waterfront features: Lake Front, Lake - Chain of Lakes, Lake Privileges, Lift - Covered, Skiing Allowed
- Body of water: LAKE VIRGINIA
Lot
- Size: 0.31 Acres
- Features: Corner Lot
Details
- Parcel number: 072230890808090
- Zoning: R-1AAA
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Wood Frame
- Foundation: Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 1982
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Public
Community & HOA
Community
- Pet fee: $0 monthly
- Subdivision: VIRGINIA HEIGHTS
HOA
- Has HOA: No
Location
- Region: Winter Park
Financial & listing details
- Price per square foot: $780/sqft
- Tax assessed value: $2,056,689
- Annual tax amount: $32,331
- Date on market: 9/25/2025
- Cumulative days on market: 25 days
- Ownership: Fee Simple
- Total actual rent: 0
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 11/24/2025 | Sold | $2,835,000-8.5%$780/sqft |
Source:  Stellar MLS #O6346603 Report a problem | ||
| 10/21/2025 | Pending sale | $3,100,000$853/sqft |
Source: Stellar MLS #O6346603 Report a problem | ||
| 10/17/2025 | Price change | $3,100,000-6%$853/sqft |
Source: Stellar MLS #O6346603 Report a problem | ||
| 9/25/2025 | Listed for sale | $3,299,000+57.1%$908/sqft |
Source: Stellar MLS #O6346603 Report a problem | ||
| 5/30/2023 | Sold | $2,100,000-4.5%$578/sqft |
Source: Public Record Report a problem | ||
| 3/13/2023 | Pending sale | $2,200,000$605/sqft |
Source: Stellar MLS #O6093381 Report a problem | ||
| 3/8/2023 | Listed for sale | $2,200,000$605/sqft |
Source: Stellar MLS #O6093381 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $31,307 +155.6% | $2,056,689 +150.2% |
| 2023 | $12,247 +4.5% | $822,062 +3% |
| 2022 | $11,721 +1% | $798,118 +3% |
| 2021 | $11,601 -0.2% | $774,872 +1.4% |
| 2020 | $11,628 +0.7% | $764,174 +2.3% |
| 2019 | $11,550 +0.5% | $746,993 +1.9% |
| 2018 | $11,492 | $733,065 -41.5% |
| 2017 | $11,492 +0.8% | $1,253,227 +0.7% |
| 2016 | $11,397 +2.1% | $1,244,059 +14.4% |
| 2015 | $11,168 -3.2% | $1,087,024 +17.4% |
| 2014 | $11,535 +2.1% | $925,624 +4.4% |
| 2013 | $11,296 +1% | $886,611 -0.1% |
| 2012 | $11,183 +2.8% | $887,859 -1% |
| 2011 | $10,879 +4.9% | $896,603 -2% |
| 2010 | $10,366 | $914,586 -3.9% |
| 2009 | -- | $952,151 -2.6% |
| 2008 | $9,592 +1.4% | $977,076 -6.2% |
| 2007 | $9,462 -6.6% | $1,041,309 +6.5% |
| 2006 | $10,132 -0.2% | $977,487 +11.2% |
| 2005 | $10,149 +4.4% | $878,978 +25.4% |
| 2004 | $9,722 +5.5% | $700,966 -0.6% |
| 2003 | $9,215 +2.6% | $705,105 +13.6% |
| 2002 | $8,983 +0.3% | $620,808 +3% |
| 2001 | $8,953 +2.3% | $602,648 +14.8% |
| 2000 | $8,755 | $524,748 |
Find assessor info on the county website
Neighborhood: 32789
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Nearby schools
GreatSchools rating
- 10/10AUDUBON PARK SCHOOLGrades: PK-8Distance: 1.4 mi
- 7/10Winter Park High SchoolGrades: 9-12Distance: 1.7 mi
Schools provided by the listing agent
- Elementary: Audubon Park K8
- Middle: Audubon Park K-8
- High: Winter Park High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$2,859,900
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$2,859,900
- Florida
- Orange County
- Winter Park
- 32789
- 255 Stirling Ave
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