$850,000
1431 PALM AVE
WINTER PARK, FL 32789
Hosted by Kelsey Payton
All Real Estate & Investments
Listing courtesy of All Real Estate & Investments. Data provided by Stellar MLS. Information deemed reliable but not guaranteed. Listing ID MFR802733164 — Stellar MLS.
$2,099,990
525 S LAKEMONT AVE
WINTER PARK, FL 32792
Hosted by Christopher Christensen
One Luxury International LLC
Listing courtesy of One Luxury International LLC. Data provided by Stellar MLS. Information deemed reliable but not guaranteed. Listing ID MFR803174877 — Stellar MLS.
$1,050,000
311 E MORSE BLVD #4-5
WINTER PARK, FL 32789
Hosted by Kim Garcia
Keller Williams Advantage Realty
Listing courtesy of Keller Williams Advantage Realty. Data provided by Stellar MLS. Information deemed reliable but not guaranteed. Listing ID MFR803251141 — Stellar MLS.
$420,000
5588 GARDEN GROVE CIR
WINTER PARK, FL 32792
Hosted by Victor Nguyen
Charles Rutenberg Realty Orlando
Listing courtesy of Charles Rutenberg Realty Orlando. Data provided by Stellar MLS. Information deemed reliable but not guaranteed. Listing ID MFR803033696 — Stellar MLS.
$429,998
2112 EASTBROOK BLVD
WINTER PARK, FL 32792
Hosted by Anyelina Domingos Cohen
Proserve Realty Group LLC
Listing courtesy of Proserve Realty Group LLC. Data provided by Stellar MLS. Information deemed reliable but not guaranteed. Listing ID MFR803174747 — Stellar MLS.
$419,000
1842 PURITAN AVE
WINTER PARK, FL 32792
Hosted by Karan Jodha
Mobed Realty, P.A.
Listing courtesy of Mobed Realty, P.A.. Data provided by Stellar MLS. Information deemed reliable but not guaranteed. Listing ID MFR803320827 — Stellar MLS.
$1,500,000
777 HALIFAX AVE
WINTER PARK, FL 32792
Hosted by Jared Smith
Safford Real Estate LLC
Listing courtesy of Safford Real Estate LLC. Data provided by Stellar MLS. Information deemed reliable but not guaranteed. Listing ID MFR803334448 — Stellar MLS.
$199,000
7471 CANFORD CT #19
WINTER PARK, FL 32792
Hosted by Karen Salter
Iad Florida LLC
Listing courtesy of Iad Florida LLC. Data provided by Stellar MLS. Information deemed reliable but not guaranteed. Listing ID MFR802617364 — Stellar MLS.
$775,000
1287 VERDANT GLADE PL
WINTER PARK, FL 32792
Hosted by Thomas Nickley, Jr
Keller Williams Realty At The Parks
Listing courtesy of Keller Williams Realty At The Parks. Data provided by Stellar MLS. Information deemed reliable but not guaranteed. Listing ID MFR802728033 — Stellar MLS.
$1,425,000
1581 MAGNOLIA AVE
WINTER PARK, FL 32789
Hosted by Jo Ann Lamar
Premier Sotheby's Intl. Realty
Listing courtesy of Premier Sotheby's Intl. Realty. Data provided by Stellar MLS. Information deemed reliable but not guaranteed. Listing ID MFR803328318 — Stellar MLS.
$4,750,000
1525 GRANVILLE DR
WINTER PARK, FL 32789
Hosted by Julie Christensen
One Luxury International LLC
Listing courtesy of One Luxury International LLC. Data provided by Stellar MLS. Information deemed reliable but not guaranteed. Listing ID MFR803174769 — Stellar MLS.
$3,999,000
1417 WILLIAMS DR
WINTER PARK, FL 32789
Hosted by Christopher Christensen
One Luxury International LLC
Listing courtesy of One Luxury International LLC. Data provided by Stellar MLS. Information deemed reliable but not guaranteed. Listing ID MFR803174827 — Stellar MLS.
Winter Park is one of Central Florida's most prestigious and sought-after communities, offering a small-town ambiance with big-city amenities just minutes from downtown Orlando. Founded in the 1880s as a winter resort for wealthy Northerners, the city has preserved its historic character through carefully maintained brick streets, a canopy of centuries-old live oaks, and a commitment to the arts anchored by Rollins College and the Charles Hosmer Morse Museum of American Art. Park Avenue, the city's charming main street, features upscale boutiques, award-winning restaurants, and a Saturday farmers' market that draws visitors from across the region. The real estate market in Winter Park reflects its desirability — homes range from meticulously restored 1920s Mediterranean estates to contemporary new construction on the city's famous chain of lakes. Lakefront properties are the crown jewels of the market, with homes on Lakes Virginia, Osceola, and Maitland commanding premium prices and rarely staying on the market for long. For buyers who want walkability, culture, and a strong sense of community without sacrificing access to Orlando's job market and attractions, Winter Park is hard to beat. Open houses in Winter Park tend to be well-attended events, often showcasing homes with exceptional architectural detail and mature landscaping.
Popular Neighborhoods in Winter Park
Explore the areas buyers love most
Park Avenue District
The heart of Winter Park, this area offers walkability to shops, restaurants, and the Central Park promenade. Homes range from historic estates to modern infill construction.
Via Tuscany & Windsong
Gated communities near Winter Park's western edge offering Mediterranean-inspired homes, community pools, and proximity to the best of both Winter Park and Orlando.
Lake Sue & Lake Virginia
Prestigious lakefront neighborhoods surrounding Rollins College, where stately homes enjoy private dock access and stunning water views.
Baldwin Park
A nearby master-planned community on the former Naval Training Center site, Baldwin Park features new urbanist design with a walkable village center, diverse home styles, and year-round community events.
Winter Park Housing Market Overview
Winter Park's housing market is one of the most competitive in Central Florida, with median prices generally exceeding the broader Orlando metro. Homes in the historic core and lakefront areas typically start in the $600s and can exceed $3 million for prime waterfront estates. Baldwin Park and adjacent areas offer relative value with townhomes and single-family homes in the $400s to $700s.