Homes for Sale in Winter Park, FL
Timeless Luxury & Sophistication curated by Andy Neal
Located just minutes from Downtown Orlando, Winter Park is a community where historic brick-paved streets meet a vibrant cultural scene. As a top-ranked luxury specialist with The Agency FL, I provide the exclusive insights you need to secure your place in this prestigious enclave.
The Chain of Lakes
Experience the peak of waterfront living. Six interconnected lakes offer private dock access, sunset boating, and views of some of Florida's most stunning historic estates.
Park Avenue Lifestyle
Often called the "Rodeo Drive of the East," Park Avenue offers world-class boutiques, Michelin-recommended dining, and an unparalleled walkable lifestyle.
Academic Excellence
Home to the historic Rollins College and top-tier public and private schools, Winter Park is the premier choice for education-focused families.
Winter Park Real Estate FAQ
What makes Winter Park luxury real estate unique?
The blend of historic 1920s architecture with modern lakefront masterpieces creates an aesthetic diversity found nowhere else in Central Florida.
Is Winter Park a good investment in 2026?
With its limited land availability and high demand for the "walkable urban" lifestyle, Winter Park property values continue to show strong resilience and growth.
FL Winter Park
Winter Park
1404 BORDER DR, Winter Park, FL 32789
Single Family Home 4 Beds 4 Baths 2,469 SqFt
Listed by Brian Hyser THE AGENCY FL
141 W LAKE SUE AVE, Winter Park, FL 32789
Single Family Home 5 Beds 7 Baths 5,500 SqFt
Listed by Brian Hyser THE AGENCY FL1049 N KENTUCKY AVE, Winter Park, FL 32789
Townhouse 3 Beds 3 Baths 2,112 SqFt
Listed by Tab Bish LLC THE AGENCY FL341 E READING WAY, Winter Park, FL 32789
Single Family Home 4 Beds 4 Baths 3,723 SqFt
Listed by Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES1411 MILLER AVE, Winter Park, FL 32789
Townhouse 3 Beds 4 Baths 1,824 SqFt
Listed by Sue Gilman KELLER WILLIAMS WINTER PARK7733 COUNTRY PL #G2, Winter Park, FL 32792
Condo 2 Beds 2 Baths 1,068 SqFt
Listed by Patty Farless PROPERTIES BY PATTY PLLC2344 WOODCREST DR, Winter Park, FL 32792
Single Family Home 4 Beds 2 Baths 1,764 SqFt
Listed by Shannon Lee EXPLORE FLORIDA REALTY SERVICES LLC1232 VALLEY CREEK RUN, Winter Park, FL 32792
Single Family Home 3 Beds 3 Baths 2,071 SqFt
Listed by James Clark CENTURY 21 ALTON CLARK1707 HARMON AVE, Winter Park, FL 32789
Single Family Home 3 Beds 2 Baths 1,669 SqFt
Listed by Nicole Howell FANNIE HILLMAN & ASSOCIATES3463 ARNEL DR, Winter Park, FL 32792
Single Family Home 3 Beds 2 Baths 1,770 SqFt
Listed by Alexa Monasterio Flores KELLER WILLIAMS ADVANTAGE 2 REALTY3463 ARNEL DR, Winter Park, FL 32792
Single Family Home 3 Beds 2 Baths 1,770 SqFt
Listed by Alexa Monasterio Flores KELLER WILLIAMS ADVANTAGE 2 REALTY2052 LEANNE CT, Winter Park, FL 32792
Single Family Home 4 Beds 2 Baths 2,264 SqFt
Listed by Karen Albright OPENDOOR BROKERAGE LLC321 SYLVAN BLVD, Winter Park, FL 32789
Single Family Home 3 Beds 3 Baths 2,821 SqFt
Listed by Mel Bernstein PREMIER SOTHEBYS INT'L REALTY1622 ARBOR PARK DR, Winter Park, FL 32789
Single Family Home 3 Beds 2 Baths 1,351 SqFt
Listed by Dawn Romance FANNIE HILLMAN & ASSOCIATES1122 WASHINGTON AVE #7B, Winter Park, FL 32789
Townhouse 2 Beds 3 Baths 1,556 SqFt
Listed by Cara Edwards ALL REAL ESTATE & INVESTMENTS1956 JAPONICA RD, Winter Park, FL 32792
Single Family Home 3 Beds 2 Baths 1,923 SqFt
Listed by Marcos Marchena PROPLOGIK REALTY INC2372 SUN VALLEY CIR #2372, Winter Park, FL 32792
Condo 2 Beds 2 Baths 1,495 SqFt
Listed by Sheila Mathews COLDWELL BANKER REALTY1695 LEE RD #A116, Winter Park, FL 32789
Condo 3 Beds 2 Baths 1,149 SqFt
Listed by Bianca Pierre REAL BROKER, LLC521 OHIO ST, Winter Park, FL 32789
Single Family Home 3 Beds 3 Baths 1,852 SqFt
Listed by Kathleen Gallagher McIver RE/MAX CENTRAL REALTY150 KILLARNEY BAY CT #5-5, Winter Park, FL 32789
Condo 2 Beds 2 Baths 1,140 SqFt
Listed by Giovanna D'Alessandro RP INVESTMENT REALTY LLC
Listings
- 1/38 38
4 Beds 4 Baths 2,469 SqFt$1,150,000Active - 1/57 57
4 Beds 4 Baths 3,723 SqFt$1,695,000Open Sun 2PM-4PM341 E READING WAY, Winter Park, FL 32789
Listed by Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES
Single Family Home
- 1/37 37
3 Beds 4 Baths 1,824 SqFt$899,000Open Sun 1PM-3PM
Explore Nearby Luxury Communities
RECENTLY SOLD LISTINGS
$268,000
Condo
$275,000
609 GALLERY DR #B204, Winter Park, FL 32792
PRICE REDUCED!!!!!!!!!IMMACULATE !!!!! Close to everything from this quiet 2nd floor 2/2 condo at THE GALLERY in Winter ...
Listed by Olga Ray A2Z REALTY GROUP
$1,350,000
Single Family Home
$1,499,900
130 W KINGS WAY, Winter Park, FL 32789
Amazing opportunity in the Forest Hills subdivision in the heart of Historic Winter Park! As you enter this charming 4 b...
Listed by Andy Neal MAXIM REALTY ORLANDO
$438,500
Single Family Home
$455,000
7103 TIMBER DR, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Welcome to your new home! This beautiful property offers a natural color...
Listed by Alli Johnston OPENDOOR BROKERAGE LLC
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Andy Neal
andy.neal@theagencyre.com