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Sold for $750,000
    • $750,000

    311 CORTLAND AVENUE, WINTER PARK, FL 32789

    2beds
    1,382sqft
    Single Family Residence
    Built in 1952
    10,001 Square Feet Lot
    $771,300 Zestimate®
    $543/sqft
    $3,374 Estimated rent

    Home value

    $771,300

    $694,000 - $856,000

    $3,374/mo

    Zestimate® history
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    What's special

    Timeless charmLarge windowsCeiling fanTongue and groove ceilingWhite tile flooringStylish wood flooringNatural light
    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!

    Zillow last checked:

    Listing updated:

    Listed by:

    Amy Turner 407-545-6430,

    KELLER WILLIAMS WINTER PARK 407-545-6430

    Bought with:

    Maria Clara Pimentel, 3559807

    THE LANDRUA GROUP REAL ESTATE INC

    Source: Stellar MLS,MLS#: O6319137MLS LogoOriginating MLS: Orlando Regional

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 2
    • Bathrooms: 2
    • Full bathrooms: 2
    Other
    • Features: Ceiling Fan(s), En Suite Bathroom, Built-in Closet
    • Level: First
    • Area: 169 Square Feet
    • Dimensions: 13x13
    Primary bedroom
    • Features: Ceiling Fan(s), En Suite Bathroom, Built-in Closet
    • Level: First
    • Area: 195 Square Feet
    • Dimensions: 15x13
    Primary bathroom
    • Features: Sink - Pedestal, Tub With Shower
    • Level: First
    Primary bathroom
    • Features: Sink - Pedestal, Tub With Shower
    • Level: First
    Bonus room
    • Features: Ceiling Fan(s), No Closet
    • Level: First
    • Area: 160 Square Feet
    • Dimensions: 16x10
    Dinette
    • Features: Ceiling Fan(s)
    • Level: First
    • Area: 160 Square Feet
    • Dimensions: 16x10
    Kitchen
    • Features: Pantry
    • Level: First
    • Area: 90 Square Feet
    • Dimensions: 10x9
    Living room
    • Features: Ceiling Fan(s)
    • Level: First
    • Area: 256 Square Feet
    • Dimensions: 16x16
    Heating
    • Central, Electric
    Cooling
    • Central Air
    Appliances
    • Included: Dishwasher, Disposal, Dryer, Range, Refrigerator, Washer
    • Laundry: In Garage
    Features
    • Ceiling Fan(s), Thermostat
    • Flooring: Ceramic Tile, Laminate, Tile, Hardwood
    • Windows: Blinds
    • Has fireplace: No
    Interior area
    • Total structure area: 1,712
    • Total interior livable area: 1,382 sqft

    Property

    Parking
    • Total spaces: 1
    • Parking features: Driveway, Garage Door Opener, Off Street
    • Attached garage spaces: 1
    • Has uncovered spaces: Yes
    • Details: Garage Dimensions: 22x16
    Features
    • Levels: One
    • Stories: 1
    • Patio & porch: Front Porch, Patio, Rear Porch
    • Exterior features: Irrigation System, Private Mailbox, Rain Gutters, Sidewalk
    • Fencing: Fenced,Vinyl
    • Waterfront features: Lake Privileges
    • Body of water: LAKE OSCEOLA
    Lot
    • Size: 10,001 Square Feet
    • Features: Corner Lot, City Lot, Sidewalk
    • Residential vegetation: Trees/Landscaped
    Details
    • Parcel number: 052230648402151
    • Zoning: R-1AA
    • Special conditions: None

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Florida,Ranch,Traditional
    • Property subtype: Single Family Residence
    Materials
    • Block, Stucco
    • Foundation: Slab
    • Roof: Shingle
    Condition
    • Completed
    • New construction: No
    • Year built: 1952

    Utilities & green energy

    • Sewer: Public Sewer
    • Water: Public
    • Utilities for property: BB/HS Internet Available, Cable Available, Electricity Connected, Sewer Connected, Water Connected

    Community & HOA

    Community
    • Features: Park, Sidewalks
    • Pet fee: $0 monthly
    • Subdivision: OSCEOLA SUMMIT
    HOA
    • Has HOA: No
    Location
    • Region: Winter Park

    Financial & listing details

    • Price per square foot: $543/sqft
    • Tax assessed value: $456,829
    • Annual tax amount: $6,589
    • Date on market: 6/26/2025
    • Cumulative days on market: 48 days
    • Listing terms: Cash,Conventional,FHA,VA Loan
    • Ownership: Fee Simple
    • Total actual rent: 0
    • Electric utility on property: Yes
    • Road surface type: Asphalt, Paved

    Price history

    DateEventPrice
    9/25/2025Sold$750,000-6.2%$543/sqft
    Source: Stellar MLS #O6319137 Report a problem
    8/13/2025Pending sale$799,900$579/sqft
    Source: Stellar MLS #O6319137 Report a problem
    6/26/2025Listed for sale$799,900+88.2%$579/sqft
    Source: Stellar MLS #O6319137 Report a problem
    6/8/2025Listing removed$3,200$2/sqft
    Source: Zillow Rentals Report a problem
    5/7/2025Listed for rent$3,200+14.3%$2/sqft
    Source: Zillow Rentals Report a problem
    5/31/2024Listing removed--
    Source: Zillow Rentals Report a problem
    5/13/2024Price change$2,800-6.7%$2/sqft
    Source: Zillow Rentals Report a problem
    4/4/2024Listed for rent$3,000+42.9%$2/sqft
    Source: Zillow Rentals Report a problem
    2/25/2021Listing removed--
    Source: Owner Report a problem
    5/5/2020Listing removed$2,100$2/sqft
    Source: Owner Report a problem
    4/24/2020Listed for rent$2,100+5%$2/sqft
    Source: Owner Report a problem
    5/9/2019Listing removed$2,000$1/sqft
    Source: Owner Report a problem
    2/27/2019Listed for rent$2,000+11.1%$1/sqft
    Source: Owner Report a problem
    4/26/2017Listing removed$1,800$1/sqft
    Source: Owner Report a problem
    4/19/2017Price change$1,800-10%$1/sqft
    Source: Owner Report a problem
    3/7/2017Listed for rent$2,000+17.6%$1/sqft
    Source: Owner Report a problem
    5/4/2016Listing removed$425,000$308/sqft
    Source: Owner Report a problem
    3/9/2016Price change$425,000-5.6%$308/sqft
    Source: Owner Report a problem
    2/6/2016Listed for sale$450,000+57.9%$326/sqft
    Source: Owner Report a problem
    4/24/2015Listing removed$1,700$1/sqft
    Source: Owner Report a problem
    4/19/2015Price change$1,700-5.6%$1/sqft
    Source: Owner Report a problem
    2/11/2015Listed for rent$1,800+6.2%$1/sqft
    Source: Owner Report a problem
    2/10/2012Listing removed$1,695$1/sqft
    Source: Express Realty World, Inc. Report a problem
    2/2/2012Listed for rent$1,695$1/sqft
    Source: Express Realty World, Inc. Report a problem
    6/1/2005Sold$285,000+111.1%$206/sqft
    Source: Public Record Report a problem
    1/9/1998Sold$135,000$98/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2024$6,589 +12.1%$388,669 +10%
    2023$5,876 +18.4%$353,335 +10%
    2022$4,963 +3.2%$321,214 +5.3%
    2021$4,811 -2.2%$305,050 -0.3%
    2020$4,917 +6.9%$306,049 +10%
    2019$4,601 +6.9%$278,226 +10%
    2018$4,305 $252,933 -4.6%
    2017$4,305 +4.4%$265,167 +1.1%
    2016$4,122 +5%$262,298 +1.9%
    2015$3,927 +24.9%$257,363 +39.4%
    2014$3,143 +14.2%$184,578 +17.5%
    2013$2,753 -0.2%$157,051 +0.6%
    2012$2,758 -1.4%$156,135 -1%
    2011$2,796 +1.3%$157,726 -1.8%
    2010$2,759 $160,620 -25.6%
    2009-- $215,748 -23.4%
    2008$4,617 -5.5%$281,753 -6.1%
    2007$4,886 +15.7%$300,140 +27.1%
    2006$4,223 +75.4%$236,144 +43.6%
    2005$2,408 +4.8%$164,407 +9%
    2004$2,296 -12.9%$150,780 +0.9%
    2003$2,638 +54.7%$149,451 +8.1%
    2002$1,704 +0.7%$138,303 +4.6%
    2001$1,693 +2.9%$132,221 +2.7%
    2000$1,645 $128,803
    Find assessor info on the county website

    Neighborhood: 32789

    Nearby homes

    Nearby schools

    GreatSchools rating
    Schools provided by the listing agent
    • Elementary: Lakemont Elem
    • Middle: Maitland Middle
    • 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
    $771,300
    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
    $771,300

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