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Property Description
Location, location, location! Whether you're ready to build your dream home or simply want to enjoy life in Central Florida's most prestigious neighborhood at an unbeatable value, this delightful mid-century 2-bedroom, 2-bathroom home offers endless possibilities. Lot size is approximately 130 ft X 78 ft. Perfectly positioned just minutes from Park Avenue, Rollins College, and Lake Osceola, this home places you at the center of luxury Winter Park living-enjoy boutique shopping, fine dining, scenic strolls, or morning paddle boarding just steps from your door. Inside, you'll find a bright and open floor plan filled with natural light and timeless charm. A front den/office with white tile flooring and timeless tongue and groove ceiling offers you space that is not only stylish but functional-ideal for working from home or relaxing with a book. The open living/dining area features stylish wood flooring, large windows, and a ceiling fan for year-round comfort. This unique layout offers 2 primary suites offering plenty of privacy. Head to the fully fenced back yard and concrete patio which provides a private retreat for entertaining or relaxing outdoors. You will find yourself in the heart of it all with close proximity shops, restaurants, schools, universities and major airports. An added hidden bonus is your access to Lake Osceola through 2 parks and walkway ramp, where you can enjoy a beautiful sunset or paddle board/kayak ride. With vintage character, and incredible location with lake access at the end of the street, this Winter Park gem is not to be missed!
Full Property Details
Full Property Details for 311 Cortland Ave
General
- Sold For: $750,000
- Taxes: $6,589 (2024)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6319137
- Added to Site: 205 day(s) ago
Rental Information
- Min. Lease: 1 Month
Interior
- Number of Rooms: 8
- Interior Features: Ceiling Fan(s), Thermostat
- Appliances: Dishwasher, Disposal, Dryer, Range, Refrigerator, Washer
- Flooring: Ceramic Tile, Laminate, Tile, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 2
Other Rooms
- Laundry: In Garage
Exterior
- Exterior Features: Irrigation System, Private Mailbox, Rain Gutters, Sidewalk
- Deck/Patio: Front Porch, Patio, Rear Porch
- Porch/Patio/Deck: Front Porch, Patio, Rear Porch
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 1
- Covered Spaces: 1
- Parking Features: Driveway, Garage Door Opener, Off Street
Location
- Area: 32789 - Winter Park
- County: Orange
- Development Name: 32789 - Winter Park
- Subdivision: OSCEOLA SUMMIT
- Driving Directions: From the downtown Winter Park area, travel east on Fairbanks Ave. As you head through the curve and Fairbanks turn into Aloma, Cortland Ave will be on your left. 311 Cortland Ave is on the corner, directly on your left.
- Direction Faces: East
School Information
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park High
Community
- Community Name: 32789 - Winter Park
- Community Features: Park, Sidewalks
- Pet Restrictions: Please verify with the city of Winter Park for pet restrictions.
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric
Utilities
- Sewer: Public Sewer
- Water District: LAKE OSCEOLA
- Water: Public
- Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Sewer Connected, Water Connected
Structural Information
- Architectural Info: Florida, Ranch, Traditional
- Architectural Style: Florida, Ranch, Traditional
- Exterior Const.: Block, Stucco
- Roof: Shingle
- Windows: Blinds
- Stories/Levels: One
- Square Feet: 1,382
- Sq. Ft. Source: Public Records
- Living Area: 1,382 Sq. Ft.
- Year Built: 1952
Lot Features
- Lot Size (Acres): 0.23
- Lot Size (Sq. Ft.): 10,001
- Lot Size: 10001
- Street/Road Desc.: Asphalt, Paved
- Fencing (Description): Fenced, Vinyl
Water Features
- Water Access: Yes
- Water Access Desc: Lake - Chain of Lakes
- Water Front Name: LAKE OSCEOLA
Financial Considerations
- Tax Amount: $6,589
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: OSCEOLA SUMMIT L/34 LOT 15 (LESS N 10 FT& W 26 FT) & LOT 16 (LESS N 10 FT & LESS BEG SE COR THEREOF RUN W 15 FT NELY TOE LINE S S 15 FT TO POB) & (LESS RD R/WON S) BLK B
- Flood Zone Info: X
- APN: 52230648402151
- Property ID: 52230648402151
- Block/Lot/Section: B
Listed by Keller Williams Winter Park
Sold by The Landrua Group Real Estate Inc
Get Pre-Approved Today
Schools
Schools serving 311 Cortland Ave
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Lakemont Elementary School 901 North Lakemont Avenue, Winter Park, FL 32792 | K-5 | 0.7 mi |
Maitland Middle School 701 North Thistle Lane, Maitland, FL 32751 | 6-8 | 2.3 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 311 Cortland Ave
Date
Details
Price
Change
Source
9/25/2025
Sold
$750,000
-6.24%
MLS
6/26/2025
Listed
$799,900
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
311 Cortland Avenue, Winter Park, FL 32789 (MLS# O6319137) is a Single Family property that was sold at $750,000 on September 25, 2025. Want to learn more about 311 Cortland 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.

