255 Stirling Avenue, Winter Park, FL 32789
For Sale $3,299,000
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Contact the Listing Agent directly:
Listing Agent: Alison Mosley
Agent Phone:
407-304-6458
Agent Email:
alison@themosleyteam.com
Scheduled Open Houses
2025-10-05 2:00 pm - 4:00 pm
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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.
Ceiling Fans(s)
Eat-in Kitchen
High Ceilings
PrimaryBedroom Upstairs
Taxes: $32,331.00
Tax Year: 2025
Balcony
Lighting
Private Mailbox
Rain Gutters
Dishwasher
Disposal
Dryer
Microwave
Refrigerator
Washer
Water
Lake Front
Lake Privileges
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Junior High: Audubon Park K-8
High School: Winter Park High
MLS Area: 32789 - Winter Park
Water: Public
Lot Desc.: Corner Lot
Construction: Frame
Date Listed: 2025-09-25 15:44:45
Pool: Yes
Pool Type: In Ground
Garage Spaces: 2
Flooring: Carpet, Tile, Wood
Roof: Shingle
Heating: Central
Cooling: Central Air
Sewer: Public Sewer
Listing Courtesy Of: Premier Sothebys Intl. Realty
alison@themosleyteam.com
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.
Property Details
Price: $3,299,000
Sq Ft: 3,635
($908 per sqft)
Bedrooms: 4
Bathrooms: 3
Partial Baths: 1
City: Winter Park
County: Orange
Type: Single Family Reside
Development: Virginia Heights
Acres: 0.32
Virtual Tour/Floorplan: View
Year Built: 1982
Listing Number: O6346603
Status Code: A-Active
Taxes: $32,331.00
Tax Year: 2025
Garage:
2
Interior Features:
Ceiling Fans(s)
Eat-in Kitchen
High Ceilings
PrimaryBedroom Upstairs
Financial Information:
Taxes: $32,331.00
Tax Year: 2025
Exterior Features:
Balcony
Lighting
Private Mailbox
Rain Gutters
Equipment:
Dishwasher
Disposal
Dryer
Microwave
Refrigerator
Washer
View:
Water
Waterfront Description:
Lake Front
Lake Privileges
School Information:
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Junior High: Audubon Park K-8
High School: Winter Park High
Additional Information:
MLS Area: 32789 - Winter Park
Water: Public
Lot Desc.: Corner Lot
Construction: Frame
Date Listed: 2025-09-25 15:44:45
Pool: Yes
Pool Type: In Ground
Garage Spaces: 2
Flooring: Carpet, Tile, Wood
Roof: Shingle
Heating: Central
Cooling: Central Air
Sewer: Public Sewer
Map of 255 Stirling Avenue, Winter Park, FL 32789
Listing Courtesy Of: Premier Sothebys Intl. Realty
alison@themosleyteam.com