$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
$2,970 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
$1,950 per month
7454 Wynnewood Square Unit 188, Winter Park, FL 32792
7454 Wynnewood Square Unit 188, Winter Park, FL 32792
$1,295 - $2,075 per month
Oak Reserve at Winter Park
1 - 3 Beds
541 Oak Reserve Ln, Winter Park, FL 32792
$3,895 per month
1409 Lone Feather Trail, Winter Park, FL 32792
Beautiful tile roof single-family house is available in Hawks Crest, the only newal gated community in Winter Park! No rear neighbors! Landscape/Lawn Care and Reclaimed Water Bill are paid by landlord. UV sanitizing lights installed in all bathrooms. Water filter system installed in kitchen sink. This 4 bed 3.5 bathrooms plus an office and second floor loft is ready to move-in . When you enter
Yan Zuo EAST PEARL REALTY
$1,562 - $3,496 per month
Bainbridge Winter Park
1 - 3 Beds
1400 Morgan Stanley Ave, Winter Park, FL 32789
$3,200 per month
1830 Staunton Ave, Winter Park, FL 32789
STYLISH, STUNNING AND RENOVATED TO THE NINES. This 3-bedroom, 2.5-bath Winter Park home has great access to Interstate-4 and both Winter Park and Orlando downtown areas. With all new interior spaces, this fantastic home is almost totally rebuilt with brand new electrical, plumbing, heating and air, ductwork, roof, flooring and Energy Star doors and windows. In addition to the 3 upstairs bedrooms,
Johnny Hurlburt COLDWELL BANKER REALTY
$1,668 - $1,703 per month
Elon Winter Park
1 Bed
712 Nicolet Ave, Winter Park, FL 32789
$2,350 per month
1571 Magnolia Ave, Winter Park, FL 32789
Fantastic bungalow in sought-after Winter Park. Great location, close to Advent Hospital Winter Park, Park Avenue, 10 minutes to I4. Large, fenced-in backyard, original hardwood floors in living area & bedrooms. Stainless appliances, granite countertops in kitchen, one car garage. Tons of natural light, indoor laundry.
Jackie O'Leary FANNIE HILLMAN & ASSOCIATES
$1,941 - $7,078 per month
Juno Winter Park
Studio - 3 Beds
1305 Morgan Stanley Ave, Winter Park, FL 32789
$2,700 per month
2176 Crandon Ave, Winter Park, FL 32789
Fully furnished and Turnkey/Renovated in-town home. Close to downtown Winter Park, Advent and Orlando Health. Newly renovated kitchen with Sub-Zero/Cafe appliances. Monthly rental only...2 bedrooms sleeps 4. Nice covered/screened porch. Available now. Weekly to monthly rental.
Dan Haber CORCORAN PREMIER REALTY
$1,832 - $3,991 per month
Paseo at Winter Park Village
1 - 3 Beds
940 W Canton Ave, Winter Park, FL 32789
$2,350 per month
1931 Staunton Ave, Winter Park, FL 32789
Available for rent! Tucked onto a desirable corner lot just steps from Lake Killarney, this beautifully updated 3 bedroom, 2 bath single-family home puts you in one of the area's most sought-after spots. Walkable, quiet, and moments from the water. Inside, the home is move-in ready with a full suite of brand-new appliances (dishwasher, range, and refrigerator) plus washer/dryer hookups ready for
Zach Mitchell SAND DOLLAR REALTY GROUP INC
$1,103 - $1,676 per month
Seabrook
1 - 2 Beds
3114 Terry Brook Dr, Winter Park, FL 32792
$1,575 per month
2911 Antique Oaks Cir Unit 12, Winter Park, FL 32792
Beautifully Remodeled 2 Bed / 2 Bath Condo – Second Floor | Prime Location Charming and fully remodeled second-floor condo located just steps from the pool. Perfect for those seeking a low-maintenance lifestyle. This bright and inviting unit features fresh paint, new wood and ceramic tile flooring, and updated bathrooms and kitchen with granite countertops and new appliances, including a washer
Clara Herrera CLARA HERRERA REALTY
$1,609 - $5,180 per month
Vintage Winter Park Apartments
1 - 3 Beds
7490 Dwell Well Way, Winter Park, FL 32792
$3,995 per month
3131 Lowndes Dr, Winter Park, FL 32792
Beautiful 4 Bedroom Furnished House with a Pool! This home has an Eat-In Updated Kitchen. There are 3 bedrooms and a bathroom on one side and a large master suite on the other side with a fireplace. The master bathroom has an extra large walk-in shower with a double mirrored dressing area. There is a family room/ FLex Space/ Office Area with a Roku TV, Desk, and Wi-Fi. There is no garage. It has
Rene' Fossey A +ROI PROPERTY
$1,359 - $2,085 per month
Cranes Landing Apartments
1 - 3 Beds
3440 N Goldenrod Rd, Winter Park, FL 32792
$2,195 per month
5523 Cretan Way, Winter Park, FL 32792
3 bedroom, 2 bathroom townhouse in highly desired Winter Park. Small and quiet neighborhood with private driveway parking and a cul de sac with no neighbors on one side. Amenities include: central air, central heat, dishwasher, garbage disposal, side-by-side fridge, electric stove/oven, gas grill, Maytag full-size washer/dryer set, yard, shed for storage, and mini bar off of the living room, and
Shawn Beard RE/MAX 200 REALTY
$1,585 - $3,346 per month
Seven41 Winter Park
Studio - 2 Beds
741 Clay St, Winter Park, FL 32789
$4,300 per month
1026 S Lakemont Ave, Winter Park, FL 32792
Lawn and pool maintenance included in rent! Welcome to this beautifully upgraded Winter Park pool home, designed for effortless living and exceptional entertaining. This 3-bedroom, 2-bath residence offers an open, inviting floor plan with a spacious kitchen featuring updated countertops and cabinetry, stainless steel appliances, beautiful bathroom finishes and updated flooring throughout. The
Lianna D'Angelo SOTERA LIVING
$1,309 - $1,774 per month
The Taylor at Winter Park
Studio - 3 Beds
2000 Village Ln, Winter Park, FL 32792
$12,000 per month
1041 Tuscany Place, Winter Park, FL 32789
Nestled along a quiet brick-lined street in Winter Park’s coveted Via’s neighborhood, 1041 Tuscany Place offers a rare blend of elegance, comfort, and breathtaking natural beauty. From nearly every room, this exceptional residence captures tranquil views of the private backyard and picturesque Lake Temple beyond. Inside, a thoughtfully designed open floor plan is enhanced by soaring vaulted
Brad Barnett COMPASS FLORIDA LLC
$1,499 - $2,018 per month
Calibre Bend Apartments
1 - 2 Beds
3924 Calibre Bend Ln, Winter Park, FL 32792
$1,600 per month
7330 Cedar Creek Ct Unit 58, Winter Park, FL 32792
Two master bedrooms upstairs, one half bathroom and laundry room downstairs. one fenced patio on the back. Water is included. Two parking spaces belong to this property.
He Gao U S GLORY REALTY
$1,660 - $5,400 per month
Berkshire Winter Park
Studio - 3 Beds
1874 Harmon Ave, Winter Park, FL 32789
$5,500 per month
1776 Mondrian Cir, Winter Park, FL 32789
One or more photo(s) has been virtually staged. Welcome to Lake Killarney Townhomes, a modern luxury and new construction waterfront community. Nestled in the heart of Winter Park, just north of downtown Orlando, these exclusive townhomes offer a unique blend of urban contemporary design and comfort. This home features a private terrace perfect for relaxing in style with slight views of Lake
Kris Kennedy COMPASS FLORIDA LLC
$1,070 - $4,057 per month
Liv at Winter Park Apartment Homes
Studio - 3 Beds
4755 N Goldenrod Rd, Winter Park, FL 32792
$2,600 per month
2530 Passamonte Dr Unit 10E, Winter Park, FL 32792
REMODELLED - new flooring and freshly painted. Welcome home to this beautiful townhome centrally located in Winter Park, 15 miles away from Park Avenue, just outside of Baldwin Park. Enjoy beautiful water views on the back patio. This home is fresh ready to move in. Available for rent April 15 or later. Top schools, Glenridge middle school, Winter Park high school and Brookshire elementary
Livia Petraru EXP REALTY LLC
$1,047 - $2,217 per month
Winter Park Woods Apartments
1 - 3 Beds
349 Scottsdale Square, Winter Park, FL 32792
$2,699 per month
1947 Summerfield Rd, Winter Park, FL 32792
Welcome home! This fantastic 3-bedroom, 2-bath home is available for immediate move-in! This property is a short drive from downtown Winter Park, the Crosby Center for Health and Wellbeing, Cady Way Park, and more! , this property features a comfortable layout with well-apportioned bedrooms and bathrooms, a lovely kitchen with lots of counter and cabinet space, and many desirable features. Act
Steve Simpson 407 PROPERTIES
$1,294 - $2,468 per month
Summerlin at Winter Park Apartments
1 - 3 Beds
3207 Rosebud Ln, Winter Park, FL 32792
$2,500 per month
7508 Glenmoor Ln, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Welcome to this beautifully refreshed 3-bedroom, 2-bath home nestled in a highly desirable Winter Park location — offering comfort, style, and convenience with no HOA restrictions. With 1,676 square feet of thoughtfully designed living space, this home is the perfect blend of modern updates and timeless character.Step inside to discover
Jenny Chien Lin AMERICAN DREAM HOMES INC
$910 - $1,544 per month
San Jose Apartments
1 - 3 Beds
2353 Winter Woods Blvd, Winter Park, FL 32792
$3,500 per month
2115 Sycamore Dr, Winter Park, FL 32789
Updated Charming 4 Bed/2 Bath mid-century home located in Northwood Terrace/Audubon Park (just across the street from Baldwin Park). You will love the large lot .34 Acres with it botanical garden, meditation area, a patio with a raised HOT Tub (perfect for a starry night) and plenty of privacy with all the lush foliage. The front door opens to a great room where the kitchen, living area, dining
John Goggin STOCKWORTH REALTY GROUP
$1,230 - $1,775 per month
Central Place At Winter Park
1 - 3 Beds
7000 University Blvd, Winter Park, FL 32792
$2,350 per month
1508 Florentino Ln, Winter Park, FL 32792
Nestled in the heart of Winter Park just off Howell Branch Rd., in the gated community of VISTAS AT LAKE HOWELL awaits this charming,spacious well equipped 2bedroom/2.5bathroom/1car garage with a loft and screen enclosed patio. This townhome features a modern aestheticfrom upgraded recessed lighting and ceiling fans, upgraded wall switches, granite counter-tops, stainless steel
Barbarite Adams REALTY HUB
$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 5
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.
There are currently 194 homes available for rent in Winter Park, FL. The median rent is $2,300 per month, with single-family homes renting at $2,650, townhouses at $2,495 and condos at $1,650.
Copyright © 2026 CoStar Group
