$1,637 - $1,678 per month
Elon Winter Park
1 Bed
712 Nicolet Ave, Winter Park, FL 32789
$1,637 - $1,678 per month
Elon Winter Park
1 Bed
712 Nicolet Ave, Winter Park, FL 32789
$1,916 - $7,001 per month
Juno Winter Park
Studio - 3 Beds
1305 Morgan Stanley Ave, Winter Park, FL 32789
$1,832 - $4,089 per month
Paseo at Winter Park Village
1 - 3 Beds
940 W Canton Ave, Winter Park, FL 32789
$1,635 - $5,384 per month
Berkshire Winter Park
Studio - 3 Beds
1874 Harmon Ave, Winter Park, FL 32789
$1,585 - $3,888 per month
Seven41 Winter Park
Studio - 2 Beds
741 Clay St, Winter Park, FL 32789
$1,145 - $2,125 per month
Westmount at Winter Park
Studio - 3 Beds
1701 Lee Rd, Winter Park, FL 32789
$1,412 - $3,429 per month
Bainbridge Winter Park
1 - 3 Beds
1400 Morgan Stanley Ave, Winter Park, FL 32789
$1,330 - $1,960 per month
Park East - Park Knowles Apartments
Studio - 2 Beds
311 N Knowles Ave, Winter Park, FL 32789
$3,200 per month
653 Symonds Ave, Winter Park, FL 32789
Charming 3BR/2.5BA single-family home in desirable Winter Park! Interior features include ceramic tile & laminate flooring, ceiling fans, and a bright kitchen with breakfast bar/kitchen island and stainless-steel appliances. Washer/dryer and major kitchen appliances included. Conveniently located near Hannibal Square, Park Ave, Central Park, Rollins College, the Winter Park Community Center, and
Alessandra Oliveira FLORIDA CONNEXION PROPERTIES
$1,522 total monthly price
1500 Gay Rd Unit 1D, Winter Park, FL 32789
EXCELLENT LOCATION, Remodeled, Lake Access, Pool, Water Included, 2nd Floor unit
$2,550 per month
316 Lake Fair Ln, Winter Park, FL 32789
Welcome to this bright and inviting home filled with natural light and beautiful hardwood floors throughout. Large windows bring in plenty of sunshine, giving the space a warm and comfortable feel. Step outside to a fully fenced backyard with lush greenery—great for relaxing or entertaining family and friends. Inside, you’ll find updated kitchen and bathroom features, generous closet space, and
$1,950 per month
520 Holt Ave, Winter Park, FL 32789
Property Id: 578482One-bedroom / one-bathroom cottage style apartment located within a five-minute walk to Rollins College, Park Avenue, and Hannibal Square. Newly-renovated interior includes condominium grade appliances, upgraded bathroom, and in-unit washer dryer. Unit includes off-street parking and private entry porch. Available for lease beginning of June 2026. Rent includes
$3,200 per month
2428 Lotafun Ave, Winter Park, FL 32789
Who wouldn’t want to live on a street called LOTAFUN? This one-story Winter Park home has 3-bedrooms, 2.5-baths with great access to Interstate-4 and both Winter Park and Orlando downtown areas. With all new interior spaces, this fantastic home is totally rebuilt with brand new electrical, plumbing, heating and air, ductwork, roof, flooring and Energy Star doors and windows. Located at the end of
Johnny Hurlburt COLDWELL BANKER REALTY
$3,350 total monthly price
1886 Demetree Dr, Winter Park, FL 32789
Available Now – Beautifully Remodeled Ground-Floor Townhome in Prime Winter ParkStep into this stylish, move-in-ready townhome located in the heart of Winter Park. Perfectly situated for both convenience and relaxation, this home is just a short walk to the popular Winter Park Dog Park and Baldwin Park, with an easy drive to Rollins College, Park Avenue, downtown Orlando, and major
$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
$1,050 per month
525 S Lakemont Ave, Winter Park, FL 32792
Room Rental Listing: Room 01 – Master Bedroom with Attached BathroomThis listing is for Room 01, the Master Bedroom with an attached bathroom, in a fully furnished 3-bedroom, 2-bathroom house.Location: SW Zone @ 525 S Lakemont Ave, Winter Park, FloridaProperty Features: Preliminary Information :Appliances Provided:Cooking range with
$4,195 per month
1625 Tioga Trail, Winter Park, FL 32789
AVAILABLE FOR MOVE-IN EARLY JUNE 2026.A RARE FIND IN WINTER PARK!! 4 BEDROOMS, 3 BATHROOMS, POOL, AND FENCED BACKYARD.Very seldom do such nice rental homes come available in the school district of Dommerich, Maitland Middle and Winter Park High! People love The Hills of Winter Park with this home located on a cul-de-sac street.This home features 4 Bedrooms and 3 Full
$3,995 per month
1667 Mizell Ave, Winter Park, FL 32789
Minimum Deposit $3995. Monthly Rent $3995. Available June 1st!Contact Polina at or email to schedule your private showing. Showings are not confirmed until you speak directly with the Property Manager and a mutually agreed upon showing day/time has been established.Welcome to your dream Winter Park home! This charming 3-bedroom, 3 full bathroom gem is the epitome of comfort and
$2,820 per month
1868 Lake Spier Dr, Winter Park, FL 32789
This beautiful 3-bedroom, 2-bathroom home features hardwood flooring throughout and an abundance of windows that fill the space with natural light. The spacious kitchen is equipped with a modern island, stainless steel appliances, and generous storage. A bright Florida room leads to a large, fenced backyard—perfect spot to relax or unwind. Ideally located near Baldwin Park, you’ll have convenient
$2,550 per month
110 Killarney Bay Ct, 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
$3,800 per month
1313 Buckingham Rd, Winter Park, FL 32789
**Move-in ready starting June 1st!! | Schedule your tour today! **Welcome to your new home! This charming 4 bed, 2 bath home in beautiful Winter Park is waiting for you to make it yours. The beautiful hardwood floors throughout the house give it a cozy and inviting feel. Enjoy the sunshine in the sunroom, or step outside and relax in the spacious yard with a fence. You'll love the
$1,595 per month
1695 Lee Rd, Winter Park, FL 32789
Beautiful and move-in ready 2 Bedroom / 1 Bathroom condo located on the second floor in a quiet, well-maintained community.This unit offers the perfect combination of comfort, space, and convenience — ideal for families or professionals looking for a clean and functional home ready for immediate move-in.PROPERTY HIGHLIGHTS:2 Bedrooms / 1 Full Bathroom - Second-floor unit
$1,400 per month
1695 Lee Rd, Winter Park, FL 32789
Don't miss out on this cozy 1-bedroom, 1-bathroom condo at Waterfall Cove. The unit has been newly painted throughout and features kitchen appliances, upgraded blinds, ceiling fans, and a full-size washer and dryer. You can also enjoy your morning coffee on the private patio. The community offers excellent amenities, including a pool, playground, and picnic area. Waterfall Cove is ideally located
$2,500 per month
151 N Orlando Ave, Winter Park, FL 32789
Discover this affordable and well-located 3-bedroom, 2-bathroom home in the desirable Winter Park area, perfect for those seeking comfort, convenience, and long-term stability.This property offers a functional layout with comfortable living spaces, ideal for families or individuals looking for a practical and welcoming place to call home.
$1,900 per month
303 Sandlewood Trail, Winter Park, FL 32789
Welcome home to this beautifully renovated two-story condo in desirable Sandlewood Trails. This 2-Bedroom, 2.5 Bath condo home is ideally located in Winter Park and is one of the few condo communities where residents are close enough to bike or walk to Dommerich Elementary and Maitland Middle School.As you enter, you are welcomed by a spacious Great Room and attractive gray-toned laminate
$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
$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
$2,300 per month
2827 Riddle Dr, Winter Park, FL 32789
Welcome to your new oasis in the charming city of Winter Park, FL! This beautiful property is perfect for those seeking comfort and convenience in a vibrant community. With nearby restaurants offering a delightful culinary experience, you'll always have something new to explore.This property features spacious accommodations designed for your relaxation. Enjoy a comfortable living
$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
$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
$2,350 per month
1931 Staunton Ave Unit 1, Winter Park, FL 32789
Property Id: 2463852Welcome to your new home at 1931 Staunton Ave in Winter Park, FL! This charming 3 bed, 2 bath unit features modern amenities such as brand new dishwasher, microwave, and washer/dryer hookups. Enjoy the convenience of a carport, driveway, and street parking. Pets are welcome, and smokers can enjoy the outdoors. Don't miss out on this fantastic rental opportunity for
$1,650 total monthly price
700 Melrose Ave, Winter Park, FL 32789
Charming 1BR/BA condo in desirable Winter Park Gardens (+55 community). Recently renovated and located in the highly sought-after Winter Park Gardens community in Winter Park, FL. This bright and inviting second floor unit overlooks the pool and has an elevator nearby. Within walking distance of Park Avenue's Shops, restaurants and other activities. (no pets allowed )Adjacent to Winter
$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
$1,400 per month
1695 Lee Rd Unit D213, Winter Park, FL 32789
Adorable and cozy second floor condo, conveniently located off Lee Road in Orlando, minutes from SR I-4. This 2-bedroom 1 full bath condo is located in the quiet community or Waterfall Cove. Water is included with a community pool and playground for tenants to enjoy. Open floor plan with carpet and laminate in kitchen and bath. Fresh paint throughout. Balcony just outside the sliders in living
Rachel DeCamp RLL Real Estate Group
$2,300 per month
151 N Orlando Ave Unit 203, Winter Park, FL 32789
FURNISHED 6-12 month executive rental available immediately in Lake Killarney Condominiums. Perfect for one or two residents, this condo offers a bedroom with King-sized bed and walk-in closet, a separate office, and a sunroom with floor to ceiling windows. Newly installed bathroom and central air system. Combo washer/dryer unit in kitchen or optional coin laundry in building. Sorry, no tenant
Robert Arnold SAND DOLLAR REALTY GROUP INC
$5,150 per month
870 Carver St, Winter Park, FL 32789
Welcome to 870 Carver Street, a one-of-a-kind rental offering two distinct, private residences on a single fully fenced property in the heart of Winter Park. The main home is a 2 bedroom, 2 bath retreat featuring vaulted ceilings with exposed rafters, warm wood finishes, and industrial-inspired black metal ductwork. The open living area is anchored by a well-appointed kitchen with solid wood
Drew Henner PREMIER SOTHEBY'S INTL. REALTY
$2,175 per month
148 Sandlewood Trail, Winter Park, FL 32789
Welcome to this charming and well-maintained rental located in a quiet, centrally situated community in the highly desirable Maitland/Winter Park area. This spacious 2-bedroom, 2.5-bathroom home offers comfort, convenience, and a low-maintenance lifestyle. Inside, you’ll find a bright and open floor plan with a generous living and dining area that flows seamlessly into the kitchen, which is
Brian Hyser THE AGENCY FL
$2,900 per month
540 W Comstock Ave, Winter Park, FL 32789
Newly Renovated | Prime Winter Park Location | Move-In Ready Opportunity Positioned in one of Central Florida’s most desirable and high-demand areas, this newly renovated residence at 540 W Comstock Ave offers a rare opportunity for tenants seeking both location and lifestyle in the heart of Winter Park. Thoughtfully updated with modern finishes, the home features a clean, refreshed interior
Fredrick Jacobs KELLER WILLIAMS GAINESVILLE REALTY PARTNERS
$3,400 per month
438 Lakeview Ave, Winter Park, FL 32789
Bring your boat and discover this charming Winter Park gem, perfectly nestled on a quiet, desirable brick-lined street. This inviting 2-bedroom, 1-bath home features beautiful hardwood floors and a warm, welcoming feel throughout. Enjoy a lakefront yard feet from the house that offers peaceful water views and the perfect setting for outdoor living. Step outside to an amazing backyard complete
Alex Scures COLONIALTOWN REALTY
$4,150 per month
1711 Chestnut Ave, Winter Park, FL 32789
Welcome home to the heart of Winter Park's coveted Tree Streets. This beautifully remodeled single-family home sits on an oversized lot just moments from Interlachen Country Club and Winter Park Racquet Club, and is zoned for Lakemont Elementary, Maitland Middle, and Winter Park High School. Inside, natural light pours through windows in every room, giving the home a bright, airy feel throughout.
Drew Henner PREMIER SOTHEBY'S INTL. REALTY
Showing Results 1 - 40, Page 1 of 2