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Central Florida Real Estate

Please review the below listings from Hanson Real Estate Group, Inc. Our team of real estate agents are standing by and would appreciate the opportunity to tell you more about any of the homes shown below. You can call us now at 352-383-3772.

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$3,100,000
28 Days On Site

255 STIRLING AVENUE
WINTER PARK, FL 32789

For Sale|Single Family Residence|Pending
4
Beds
4
Total Baths
3
Full Baths
1
Partial Bath
3,635
SqFt
$853
/SqFt
1982
Built
Subdivision:
VIRGINIA HEIGHTS
County:
Orange
Call Now: 352-383-3772
Is this the listing for you? We can help make it yours.
352-383-3772
255 STIRLING AVENUE255 STIRLING AVENUE255 STIRLING AVENUE255 STIRLING AVENUE
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Monthly Payment (Est.)

$14,143
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2025 Information is deemed reliable but not guaranteed.

Under contract-accepting backup offers. 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.

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Listing Snapshot
Price 
$3,100,000
Days On Site 
28 Days
Bedrooms 
4
Inside Area (SqFt) 
3,635 sqft
Total Baths 
4
Full Baths 
3
Partial Baths 
1
Lot Size 
0.32 Acres
Year Built 
1982
MLS® Number 
O6346603
Status 
Pending
Property Tax 
$32,331
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
Public Records
Friends & Family
Recent Activity
3 days agoListing updated with changes from the MLS®
3 days agoStatus changed to Pending
7 days agoPrice changed to $3,100,000
4 weeks agoListing first seen on site
General Features
Acres 
0.32
Attached Garage 
Yes
Direction Faces 
South
Foundation 
Slab
Garage 
Yes
Garage Spaces 
2
Levels 
Two
Parking 
Attached
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
SqFt Total 
4580
Water Source 
Public
Zoning 
R-1AAA
Interior Features
Appliances 
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Cooling 
Central Air
Fireplace 
Yes
Fireplace Features 
Living Room
Flooring 
CarpetTileWood
Heating 
Central
Interior 
Eat-in KitchenHigh Ceilings
Laundry Features 
Inside
Bathroom 2 
Level - Second
Bedroom 3 
Level - Second
Bedroom 4 
Level - Second
Den 
Level - First
Dining Room 
Level - First
Foyer 
Level - First
Kitchen 
Level - First
Living Room 
Level - First
Master Bedroom 
Level - Second
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Exterior Features
Construction Details 
Frame
Exterior 
BalconyLightingRain GuttersDock
Lot Features 
Corner LotWaterfront
Pool Features 
In GroundPrivate
Private Pool 
Yes
Roof 
Shingle
View 
LakeWater
Waterfront 
Yes
Waterfront Features 
Lake PrivilegesLake Front
Waterview 
LakeWater
Community Features
MLS Area 
32789 - Winter Park
Roads 
Paved
Township 
22
Schools
School District
Unknown
Elementary School
Audubon Park K8
Middle School
Audubon Park K-8
High School
Winter Park High
Listing courtesy of PREMIER SOTHEBY'S INTL. REALTY 4073046458



Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2025, Stellar MLS.
Last checked: 2025-10-24 08:22 AM EDT

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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