$1,799 per month
151 N Orlando Ave Unit 101, Winter Park, FL 32789
151 N Orlando Ave Unit 101, Winter Park, FL 32789
$6,995 per month
2075 Jewell Ave, Winter Park, FL 32789
2075 Jewell Ave, Winter Park, FL 32789
$2,975 per month
1891 Oglesby Ave, Winter Park, FL 32789
1891 Oglesby Ave, Winter Park, FL 32789
$1,465 per month
2500 Lee Rd Unit 244, Winter Park, FL 32789
2500 Lee Rd Unit 244, Winter Park, FL 32789
$1,750 per month
1500 Gay Rd Unit 18A, Winter Park, FL 32789
1500 Gay Rd Unit 18A, Winter Park, FL 32789
$1,295 - $2,075 per month
Oak Reserve at Winter Park
1 - 3 Beds
541 Oak Reserve Ln, Winter Park, FL 32792
$11,000 per month
1814 Barker Dr, Winter Park, FL 32789
Stunning newer-construction luxury home in Winter Park offering 5 bedrooms, 4 baths, and 4,100 sq ft of modern living. Sleek architectural lines, abundant natural light, and seamless indoor–outdoor flow define this exceptional residence. The chef’s kitchen features premium stainless steel appliances, breakfast bar, custom cabinetry, and a large walk-in pantry. The spacious living area includes a
Tab Bish LLC REAL BROKER, LLC
$1,550 - $3,572 per month
Bainbridge Winter Park
1 - 3 Beds
1400 Morgan Stanley Ave, Winter Park, FL 32789
$1,775 per month
2420 Euston Rd, Winter Park, FL 32789
One or more photo(s) has been virtually staged. Beautifully mainted and move-in ready home available for rent in a convenient location. This property features a bright and inviting interior with functional layout, spacious living areas, and well-sized bed rooms. The home offers a clean feel with plenty of natural light throughout, creating a comfortable and welcoming environment. Enjoy a private
Paula Wells PRIMAC GROUP, INC
$1,688 - $1,699 per month
Elon Winter Park
1 Bed
712 Nicolet Ave, Winter Park, FL 32789
$1,450 per month
1555 Michigan Ave, Winter Park, FL 32789
Are you looking for a spacious 1 bedroom 1 bathroom unit to call home? This home features its own washer and dryer, a large bedroom and living room, a spacious kitchen with ample countertop space, plenty of cabinets. The back sunroom would make a great office or a bright sitting area. The home is located 1 mile from Park Avenue. In addition, the home is located within walking distance of
Troy Hensley BHHS FLORIDA REALTY
$1,700 - $4,775 per month
Juno Winter Park
Studio - 3 Beds
1305 Morgan Stanley Ave, Winter Park, FL 32789
$1,800 per month
1695 Lee Rd Unit D116, Winter Park, FL 32789
Welcome Home to Waterfall Cove in Winter Park! This spacious 3-bedroom, 2-bath ground floor corner unit is move-in ready with fresh paint and brand new carpet throughout. Corner placement means extra natural light and a layout that lives even larger than its generous footprint. Community Perks include a sparkling pool just in time for summer, secured building access, and a peaceful, park-like
Ryan Hoppe ZEAL REALTY
$1,769 - $6,687 per month
Paseo at Winter Park Village
1 - 3 Beds
940 W Canton Ave, Winter Park, FL 32789
$5,250 per month
1640 Palm Ave, Winter Park, FL 32789
Fully renovated with stylish charm, this four-bedroom, three-bath home is in one of the most desired neighborhoods in Winter Park, the Tree Streets. A brick drive and path welcome you into this open living plan on a large 75-foot by 150-foot lot with tons of room to grow. Warm wood floors throughout and this home enjoys an open kitchen family plan with spaces that are flexible for your needs. The
Alison Mosley PREMIER SOTHEBY'S INTL. REALTY
$1,173 - $1,809 per month
Seabrook
1 - 2 Beds
3114 Terry Brook Dr, Winter Park, FL 32792
$2,825 per month
2356 Coldstream Dr, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Lovely home in Winter Park school district. Closet to downtown Winter Park. Updated kitchen and baths on a Quiet street. Lawncare included.
Donna Peebles VIA PROPERTIES LLC
$1,574 - $5,689 per month
Vintage Winter Park Apartments
1 - 3 Beds
7490 Dwell Well Way, Winter Park, FL 32792
$3,650 per month
1317 Medinah Ct, Winter Park, FL 32792
Winter Park Pines home,4 bed/2 bath ready for a new resident. On a quiet cul-de-sac, this renovated home offers a blend of modern amenities with a fantastic location. It features a brand new kitchen & bathrooms with quartz countertops, updated brushed brass fixtures, with lots of custom touches. It features engineered wood flooring in the living areas and primary bedroom, a convenient indoor
Jackie O'Leary FANNIE HILLMAN & ASSOCIATES
$1,243 - $1,985 per month
Cranes Landing Apartments
1 - 3 Beds
3440 N Goldenrod Rd, Winter Park, FL 32792
$1,350 per month
2929 Antique Oaks Cir Unit 53, Winter Park, FL 32792
Welcome to this fully renovated residence in the heart of Winter Park, where modern upgrades meet timeless charm in one of Central Florida’s most desirable communities. Thoughtfully updated throughout, this home offers a fresh, move-in-ready living experience with stylish finishes and enhanced comfort. Ideally situated near Full Sail University and Rollins College, this property is well-suited
Betsy Breton-Garcia KELLER WILLIAMS WINTER PARK
$1,585 - $3,136 per month
Seven41 Winter Park
Studio - 2 Beds
741 Clay St, Winter Park, FL 32789
$3,895 per month
1430 Lone Feather Trail, Winter Park, FL 32792
Welcome to this newly built and well-maintained home in the fabulous Winter Park gated community of Hawk's Crest. A gorgeous open floor plan single-family home with 4 bedrooms, 3.5 bathrooms and office / den room on the first floor. Be amazed by the spacious bright entrance and soaring ceilings in the family room and loft open to below. Tile throughout living areas, carpet in all four bedrooms.
Mo Jabr RE/MAX 200 REALTY
$889 - $2,008 per month
The Taylor at Winter Park
Studio - 3 Beds
2000 Village Ln, Winter Park, FL 32792
$2,890 per month
524 Byron Rd, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4-bedroom, 3-bathroom home located in the heart of highly desirable Winter Park area. Offering a rare combination of space, comfort and prime location. This home offers a spacious and functional layout with multiple living areas, abundant natural light, and well-sized bedrooms. The flexible floor plan provides
Razan Mohamed SOUTHERN PRESTIGE REALTY INC
$1,499 - $2,018 per month
Calibre Bend Apartments
1 - 2 Beds
3924 Calibre Bend Ln, Winter Park, FL 32792
$1,750 per month
1695 Lee Rd Unit C206, Winter Park, FL 32789
Beautiful and move-in ready condo!Located on the second floor in a quiet community, perfect for families or professionals seeking comfort and convenience. 1.- Property Features2 Bedrooms1 Full BathroomSecond-floor unit (added privacy)Total area: 881 sqft 2.- Comfort & Interior FeaturesCentral Air ConditioningCentral HeatingCeiling FansHigh CeilingsOpen
Yein Ross ROSS RENTALS LLC
$1,500 - $5,399 per month
Berkshire Winter Park
Studio - 3 Beds
1874 Harmon Ave, Winter Park, FL 32789
$4,200 per month
668 Overspin Dr, Winter Park, FL 32789
One or more photo(s) has been virtually staged. A contemporary, beautifully finished home offering standout value in one of Winter Park’s most coveted zip codes. With more than 2,500 square feet of bright, open living space, this property features a sleek fireplace, a large pantry area, a designer kitchen, and a massive two-car garage. The private primary suite sits upstairs along with additional
Kris Kennedy COMPASS FLORIDA LLC
$1,129 - $3,411 per month
Liv at Winter Park Apartment Homes
Studio - 3 Beds
4755 N Goldenrod Rd, Winter Park, FL 32792
$2,550 per month
110 Killarney Bay Ct Unit 1, Winter Park, FL 32789
Enjoy easy, lakefront living in this beautifully maintained 2-bedroom, 2-bath condo in the desirable Killarney Bay community in Winter Park! This spacious unit features an open-concept layout with abundant natural light, a well-appointed kitchen, and comfortable living and dining areas—perfect for both relaxing and entertaining. Both bedrooms offer generous space, with a private primary suite
David Drawdy KELLER WILLIAMS REALTY AT THE PARKS
$1,312 - $2,475 per month
Summerlin at Winter Park Apartments
1 - 3 Beds
3207 Rosebud Ln, Winter Park, FL 32792
$2,500 per month
2846 Euston Rd, Winter Park, FL 32789
Welcome to a true Mid-Century rental in Winter Park located in the quaint neighborhood of Fairbank Shores. Spacious 2 bedrooms and 1.5 bath home with 1 extra flexible room that can be used as an office or 3rd bedroom(no closet). Centrally located, minutes form I4, close to Park Avenue District, College Park, major shopping centers and many more. Big backyard with a nice sized paved courtyard and
Vanessa Laboy 365 REALTY, INC.
$910 - $1,544 per month
San Jose Apartments
1 - 3 Beds
2353 Winter Woods Blvd, Winter Park, FL 32792
$3,600 per month
1461 Lone Feather Trail, Winter Park, FL 32792
Beautiful newer two-story home in Winter Park’s exclusive Gated community of Hawk’s Crest. Community has lake access with canon launch. The home has a great floor plan that features open dining and living rooms. Mastered room is conveniently located on the first floor. also Study room. This gated community features a resort style swimming pool, fitness center, splash pad, clubhouse, playgrounds,
Steve Kim MARVIEW INTERNATIONAL REALTY LLC
$1,170 - $1,975 per month
Central Place At Winter Park
1 - 3 Beds
7000 University Blvd, Winter Park, FL 32792
$1,350 per month
4818 Tangerine Ave Unit 4818, Winter Park, FL 32792
One or more photo(s) has been virtually staged. The 1 bed, 1 bath unit is ideally located in Winter Park, close to Full Sail and UCF. Rent includes water, and all appliances including washer & dryer. A spacious Living/Dining space and a Huge bedroom make this the best one bed/one bath you'll find. You're just a short drive from downtown and other Orlando hotspots. Wrenwood is a very quiet
Torey Eisenman BENCHMARK REAL ESTATE GRP INC
$1,250 - $1,350 per month
Eastbrook Apartments
1 - 2 Beds
2610-2617 Eastbrook Blvd, Winter Park, FL 32792
$2,167 per month
717 Denton Rd, Winter Park, FL 32792
Winter Park 4 Bedrm Home for Rent!Priced Low, Call Now!, 2 Car Carport, Bonus Room Too!, Eat In Kitchen, JUST 20 MINUTES To: Downtown Orlando, JUST 30 MINUTES To: The Orlando Airport, CONVENIENT To: 436, CONVENIENT To: Major Roads, Shopping & Schools, CONVENIENT To: Full Sail University, Stainless Steel Appliances INCLUDED, Blinds INCLUDED. The deposit amount is based upon the application
Jay Myers ORLANDO REALTY & PROPERTY MGNT
$1,750 per month
Park East - Park Knowles Apartments
Studio - 2 Beds
311 N Knowles Ave, Winter Park, FL 32789
Showing Results 1 - 40, Page 1 of 4
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.
Copyright © 2026 CoStar Group
