$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
$1,799 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
$1,295 - $2,075 per month
Oak Reserve at Winter Park
1 - 3 Beds
541 Oak Reserve Ln, Winter Park, FL 32792
$2,200 per month
7522 Laurel Springs Dr, Winter Park, FL 32792
Winter Park High School District! Well-maintained 3-bedroom and 2-bathroom home in Laurel Springs featuring a bright, spacious living area with brand new vinyl floor. Step into a large enclosed patio overlooking a fully fenced backyard—perfect for relaxing evenings or hosting gatherings year-round. Convenient access to shopping, dining, and major highways. Move-in ready—don’t miss this
Liu Zhang JOY ESTATE ENTERPRISE INC
$1,465 - $3,341 per month
Bainbridge Winter Park
1 - 3 Beds
1400 Morgan Stanley 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
$1,649 per month
Elon Winter Park
1 Bed
712 Nicolet Ave, Winter Park, FL 32789
$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
$1,635 - $9,294 per month
Juno Winter Park
Studio - 3 Beds
1305 Morgan Stanley Ave, Winter Park, FL 32789
$7,200 per month
1016 Howell Branch Rd, Winter Park, FL 32789
Canal Front Oasis on the Winter Park Chain of Lakes! Welcome to 1016 Howell Branch Road,where every day feels like a getaway. (Property can be leased furnished for an additional fee.) This beautifully reimagined 4-bedroom, 3-bath residence offers 3,142 square feet of inspiredliving space set amid lush, tropical landscaping — all within the bestof Winter Park and Maitland. *The canal
Andrew Birr PLAID PROPERTIES, LLC
$1,807 - $6,390 per month
Paseo at Winter Park Village
1 - 3 Beds
940 W Canton Ave, Winter Park, FL 32789
$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.
$1,233 - $1,809 per month
Seabrook
1 - 2 Beds
3114 Terry Brook Dr, 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
$1,574 - $5,746 per month
Vintage Winter Park Apartments
1 - 3 Beds
7490 Dwell Well Way, 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
$1,412 - $2,026 per month
Cranes Landing Apartments
1 - 3 Beds
3440 N Goldenrod Rd, 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
$1,550 - $3,136 per month
Seven41 Winter Park
Studio - 2 Beds
741 Clay St, Winter Park, FL 32789
$1,895 per month
295 Sandlewood Trail, Winter Park, FL 32789
This 2 bedroom, 2.5 bathroom townhome is located in Winter Park's desirable Sandlewood Creek community. Enjoy Park Avenue's shops and restaurants, Winter Park Village, highly rated schools, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a spacious main living area with open living room and dining room, a
Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY
$1,201 - $2,029 per month
The Taylor at Winter Park
Studio - 3 Beds
2000 Village Ln, Winter Park, FL 32792
$4,000 per month
1091 Wildmeadow Run, Winter Park, FL 32792
1
Maggie Walas FORTUNE INTERNATIONAL REALTY
$1,499 - $2,018 per month
Calibre Bend Apartments
1 - 2 Beds
3924 Calibre Bend Ln, Winter Park, FL 32792
$1,650 per month
2936 Antique Oaks Cir Unit 70, Winter Park, FL 32792
Call to schedule your private showing of this well-maintained 2 bedroom, 2 bathroom condo located on the second floor in the desirable Parkview Village Subdivision.This bright and open floor plan features a spacious living room with vaulted ceilings, perfectly positioned at the front of the home and open to the kitchen. The kitchen has all new appliances with a corner window that is perfect for
Jacqueline Ramos JML REALTY INVESTMENTS LLC
$1,510 - $5,399 per month
Berkshire Winter Park
Studio - 3 Beds
1874 Harmon Ave, Winter Park, FL 32789
$3,300 per month
870 Carver St Unit A, Winter Park, FL 32789
Welcome to 870 Carver Street, a thoughtfully designed two-bedroom, two-bath residence in the core of Winter Park. Offering more than 1,200 square feet, the newly constructed home features vaulted ceilings with exposed rafters, warm wood finishes and industrial-inspired black metal ductwork that define its architectural character. The primary suite includes a floating wall closet system, a laundry
Drew Henner PREMIER SOTHEBY'S INTL. REALTY
$1,172 - $3,702 per month
Liv at Winter Park Apartment Homes
Studio - 3 Beds
4755 N Goldenrod Rd, Winter Park, FL 32792
$4,500 per month
1802 Arbor Park Dr, Winter Park, FL 32789
Welcome home to this beautifully maintained 4-bedroom, 3-bath pool home located in Winter Park’s highly desirable Tree Streets neighborhood—an area known for its charming, tree-lined roads and peaceful atmosphere. Situated on an oversized .27-acre lot, one of the largest in the community, this property offers rare space and privacy while still being close to everything Winter Park has to offer.
Jorge Perez Gonzalez TBRO REALTY LLC
$1,094 - $1,955 per month
Winter Park Woods Apartments
1 - 3 Beds
349 Scottsdale Square, Winter Park, FL 32792
$5,900 per month
220 W Reading Way, Winter Park, FL 32789
Welcome to your dream home! This recently renovated gem in the highly coveted Forrest Hills area of Winter Park is now available for rent. Surrounded by enchanting brick streets and majestic trees, this charming residence has been thoughtfully upgraded by the new owner, offering a perfect blend of modern amenities and classic charm. As you step onto the inviting front covered porch, you'll be
Thomas Hewitt HEWITT RESIDENTIAL, LLC
$1,337 - $2,492 per month
Summerlin at Winter Park Apartments
1 - 3 Beds
3207 Rosebud Ln, Winter Park, FL 32792
$13,500 per month
1860 Via Contessa, Winter Park, FL 32789
Exceptional Lease Opportunity | The Vias, Winter Park$13,500/mo | $15,000 Security Deposit | One-Year Lease | Pets Considered (Owner Approval) | Available NowRarely does a home of this caliber come to market for lease. Set on a quiet cul-de-sac in one of Winter Park's most prestigious enclaves — the coveted Vias neighborhood — this magnificent 7,000 SF residence delivers an unmatched
Kelly Price KELLY PRICE & COMPANY LLC
$910 - $1,544 per month
San Jose Apartments
1 - 3 Beds
2353 Winter Woods Blvd, Winter Park, FL 32792
$1,500 per month
7326 Swallow Run Unit 7326, Winter Park, FL 32792
Bright and freshly updated ground-floor 2-suite condo in a peaceful, well-kept community. This move-in-ready home features new interior paint, new water heater, granite countertops, and durable vinyl plank flooring throughout. The split-suite layout offers privacy and flexibility for roommates or professionals. Zoned for Cheney Elementary, with convenient access to A-rated middle and high
Jiny Lee NOBSKA REAL ESTATE LLC
$1,345 - $1,975 per month
Central Place At Winter Park
1 - 3 Beds
7000 University Blvd, Winter Park, FL 32792
$5,895 per month
1235 Via Estrella, Winter Park, FL 32789
Rare opportunity to lease a fully renovated 4-bedroom, 3-bath home in one of Winter Park's most coveted enclaves — The Vias. Spanning 2,207 SF, this sun-drenched residence has been thoughtfully updated throughout and sits just a short stroll from the prestigious Winter Park Racquet Club.Step outside to your private backyard oasis, where a sparkling pool and heated spa are framed by lush,
Kelly Price KELLY PRICE & COMPANY LLC
$1,250 - $1,350 per month
Eastbrook Apartments
1 - 2 Beds
2610-2617 Eastbrook Blvd, Winter Park, FL 32792
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
