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Winter Park, FL Multifamily Homes & Duplexes for Sale

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  • /26

    $600,000

    • 3 Beds
    • 3 Baths
    • 1,452 Sq Ft

    1550 Michigan Ave, Winter Park, FL 32789

    Incredible Investment Opportunity in Winter Park!Come take a look at this amazing property located in the heart of Winter Park — just steps from Orlando Avenue, with its fantastic restaurants, shops, and the vibrant lifestyle found only in Winter ParkThis charming 1947 fully remodeled bungalow offers 2 bedrooms and 1 bathroom and is accompanied by a 1-bedroom, 1-bathroom in law-suite in

    Carolina Alfonzo 407HUB REAL ESTATE LLC

    1550 Michigan Ave, Winter Park, FL 32789
  • /18

    $2,499,000

    • 4,056 Sq Ft

    1903 S Lakemont Ave, Winter Park, FL 32792

    Location, location, location! This is an amazing opportunity to build/renovate on a premier lakefront lot in the charming and upscale Winter Park neighborhood of Orlando, Florida. Located on Lake Spier and across the street from the beautiful Baldwin Park, this exceptional-almost one acre property-includes six 1/1 units. This prime property is minutes from award winning restaurants, sidewalk

    Maria Tenner Platinum Properties Int'l Inc.

    1903 S Lakemont Ave, Winter Park, FL 32792
  • /26

    $625,000

    • 3 Beds
    • 3 Baths
    • 1,890 Sq Ft

    1360 Formosa Ave, Winter Park, FL 32789

    Discover a rare and lucrative opportunity at 1360 Formosa Ave, a corner lot triplex in the highly sought-after Winter Park market. This income-generating property features three fully rented one-bedroom, one-bathroom units, providing a strong and steady return on investment. With 100% occupancy, this property is already a cash-flowing asset, but its value-add potential makes it even more enticing

    Salvison Dickson TOP FLORIDA HOMES

    1360 Formosa Ave, Winter Park, FL 32789
  • /49

    $1,275,000

    • 6 Beds
    • 4 Baths
    • 2,284 Sq Ft

    726 and 720 N Pennsylvania Ave, Winter Park, FL 32789

    Welcome to this exceptional duplex, a rare gem in Winter Park offering unmatched flexibility and investment potential. Whether you’re looking for a turnkey rental property, a multigenerational living solution, or a home with a private in-law or student suite, this property delivers! Each spacious unit boasts 3 bedrooms and 2 bathrooms, designed with a modern, elegant aesthetic. With dual living

    Dominick Florio RE/MAX TOWN & COUNTRY REALTY

    726 and 720 N Pennsylvania Ave, Winter Park, FL 32789
  • /6

    $429,900

    • 4 Beds
    • 4 Baths
    • 1,934 Sq Ft

    3128 Patel Dr, Winter Park, FL 32792

    Don't miss this income producing duplex just minutes from University Ave and the UCF area! The separate units are 2 bedroom, 2 bath on each side and include ceramic tile/laminate flooring, spacious living room, kitchen with appliances, spacious closets, ceiling fans, washer/dryer hookups, and spacious fenced back yard.The property is currently rented on a month to month basis at

    Keith Race FUSILIER MANAGEMENT GROUP

    3128 Patel Dr, Winter Park, FL 32792
  • /27

    $700,000

    • 3 Beds
    • 2 Baths
    • 1,407 Sq Ft

    865 S Pennsylvania Ave, Winter Park, FL 32789

    LOCATION, LOCATION, LOCATION...Desirable Winter Park "College Quarter" Historic District...Come take a tour of this wonderfully updated Bungalow with lots of windows for natural light, original hardwood floors, beautiful crown molding, and high ceilings. Did I mention the location, Walk to Park Ave, Rollins College, Hannibal Square, Mead Gardens, and Lake Virginia. Looking to "House Hack" then

    Jose Vega LPT REALTY, LLC

    865 S Pennsylvania Ave, Winter Park, FL 32789

Why Live in Winter Park

Winter Park, located near Orlando, Florida, began in the 1880s as a planned community appealing to northern ex-pats with its warm winters, good schools, and lively arts scene. Today, it maintains its "City of Arts and Culture" nickname with museums and a vibrant cultural atmosphere. The main commercial district, Park Avenue, features high-end boutiques and bistros, including The Ravenous Pig, a renowned gastropub. Rollins College and The Rollins Museum of Art are local highlights, along with The Alfond Inn, which serves as a social hub. The city’s nearly 30,000 residents enjoy highly rated schools such as Winter Park High and Trinity Preparatory School of Florida. Housing options range from petite bungalows to lakeside mansions, with styles including New Traditional, midcentury-era ranch homes, Colonial Revival, and Contemporary homes. The Winter Park Chain of Lakes offers boating, kayaking, and paddleboarding opportunities, while Central Park provides 11 acres of green space with walking paths and a rose garden. Annual events like the Winter Park Sidewalk Arts Festival and Christmas on Park attract visitors and foster community spirit. Residents have access to Interstate 4, SunRail, and Lynx buses for transportation, with Orlando International Airport about 20 miles away. Winter Park’s crime rates are lower than the national average, making it a safer area compared to nearby Orlando.

Home Trends in Winter Park, FL

Housing Trends

Median Sale Price
$469,190
Median Single Family Sale Price
$830,000
Median Townhouse Sale Price
$775,000
Median 2 Bedroom Sale Price
$170,000
Median 1 Bedroom Sale Price
$149,000
Average Price Per Sq Ft
$339
Number of Homes for Sale
29
Last 12 months Home Sales
171
Months of Supply
2.00
Median List Price
$630,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
5%
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