Multiple Cities, Zip Codes, Addresses, Streets, Neighborhoods, MLS IDs
(separate each with the word OR)
Ex.Miami OR Coral Springs OR Boca Raton33319 OR 33321 OR 33467
Find Winter Park Real Estate for Rent by clicking on the relevant neighborhood.
View all Winter Park Real Estate for Rent
WHISPERWOOD CONDO 04 - O6417858 - 7302 SWALLOW RUN #7302, WINTER PARK, FL 32792 Just Added on 06/17/2026 4:29PM
$1,495 | Condo | 2 beds | 2.0 baths
This 2 bedroom, 2 bathroom condo is located in Winter Park's Whisperwood community near local shops, restaurants, and schools. Features include a spacious living area with dining room, lovely kitchen with granite countertops, a wonderful primary suite, and outdoor patio. Community amenities include a swimming pool. Pets under 35 lbs. Schedule a showing or submit an application online. All Real Property Management & Realty residents enjoy convenience and well-maintained homes, with our safe and secure online portal where you can submit maintenance requests and pay online with multiple payment options, and a 24/7 emergency maintenance response team. Please note the listed amenities may not be accurate.
Listing is courtesy of: REAL PROPERTY MANAGEMENT AND REALTY
GRAYSON SQUARE - O6417872 - 2737 BRIGHT BIRD LN, WINTER PARK, FL 32792 Just Added on 06/17/2026 3:57PM
$2,600 | Townhouse | 3 beds | 3.0 baths | 1 gar
DO not miss out on this thoughtfully designed townhome! This gorgeous end unit Marigold two-story townhome has no direct rear neighbors, water view and features a Craftsman exterior. Townhome offers 3 bedrooms, 2 full bathrooms, a powder room, a two-car garage and a covered lanai. The kitchen is fully equipped with a pantry, modern gray cabinetry, a Suite Arabesque ceramic tile backsplash, Lagoon quartz countertops and beautiful Positano Blanco porcelain tile flooring. Upstairs the primary Suite features a spacious walk-in closet, and the primary bathroom offers a double sink quartz-topped vanity, a linen closet, private water closet and walk-in shower. Grayson Square is an intimate gated luxury townhome community located minutes away from downtown Winter Park, right off Howell Branch Road! This neighborhood has gated access, a resort-style pool with cabana and 1GB high-speed fiber optic internet, along with 75 streaming cable and music channels included in rent!!! Schedule your showing today!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES
ALOMA TRAILS - O6416150 - 7628 ALOMA PINES CT, WINTER PARK, FL 32792 1 Day on yellowkey
$2,495 | Townhouse | 3 beds | 2.5 baths | 2 gar
This 3 bedroom, 2.5 bathroom townhouse is located in the gated community of Aloma Trails near downtown Winter Park and local shops, restaurants, and schools. Features include an open floor plan with tile flooring throughout the downstairs main living area. The upgraded kitchen features 42" cabinets, granite counter tops, stainless steel appliances, tiled back splash, an island, and walk-in pantry. Upstairs you will find the carpeted bedrooms and primary suite with dual sinks, walk-in shower, and 2 walk-in closets. Additional home features include a 2 car garage, patio with quiet backyard area, and laundry closet. Sorry, no students. Pets under 50 lbs. Schedule a showing or submit an application online. All Real Property Management & Realty residents enjoy convenience and well-maintained homes, with our safe and secure online portal where you can submit maintenance requests and pay online with multiple payment options, and a 24/7 emergency maintenance response team. Please note the listed amenities may not be accurate.
LANCELOT AT WINTER PARK CONDO - O6417268 - 3651 N GOLDENROD RD #B207, WINTER PARK, FL 32792 1 Day on yellowkey
$1,295 | Condo | 2 beds | 2.0 baths
Beautifully Updated 2-Bed/2-Bath Condo Near UCF & Full Sail! Step into this stylish and freshly updated second-floor condo, featuring two spacious bedrooms and two modern bathrooms. You'll love the new luxury vinyl plank flooring and fresh paint throughout, creating a clean, contemporary feel. Enjoy the light and airy open-concept living space, filled with natural sunlight and perfect for both relaxing and entertaining. The kitchen shines with updated white shaker cabinets and elegant marble-look countertops. Conveniently located just minutes from UCF and Full Sail University, this home is perfect for students, professionals, or anyone seeking easy access to everything East Orlando has to offer. Residents of Lancelot Condominiums enjoy access to a sparkling community pool.
Listing is courtesy of: MAINFRAME REAL ESTATE
MINNESOTA CONDO - O6416830 - 1105 MINNESOTA AVE #5, WINTER PARK, FL 32789 1 Day on yellowkey
$3,000 | Townhouse | 3 beds | 2.5 baths | 2 gar
Beautiful and very spacious 3BR/2.5BA with 2 car garage, large upstairs balcony, fenced patio, New wood flooring throughout the unit, all appliances including side by side refrigerator and full size washer and dryer. This property is centrally located in winter park FL,walking distance to shopping, restaurants, bars, coffee shops, Publix Supermarket, short driving distance to downtown Orlando and Advant Health Orlando hospital and close proximity to Park Ave Won't last long , please call to schedule your appointment today.
Listing is courtesy of: HPL REALTY INVESTMENTS
- S5151826 - 1000 S SEMORAN BLVD #103, WINTER PARK, FL 32792 5 Days on yellowkey
$1,750 | Condo | 3 beds | 2.0 baths
Virtually Staged. Stylish Winter Park Condo Living – Spacious 3-Bedroom Home in a Prime Location! Welcome to 1000 S. Semoran Blvd #103, a beautifully maintained 3-bedroom, 2-bath residence offering comfort, convenience, and an unbeatable Winter Park location. Featuring a bright and open floor plan, this home provides the perfect space for relaxing, entertaining, and enjoying everyday living. The well-designed layout includes spacious living and dining areas, generously sized bedrooms, and a private primary suite for added comfort. The kitchen offers ample cabinet and counter space, making meal preparation easy and enjoyable. Located in the heart of Winter Park, you'll enjoy convenient access to top-rated schools, shopping centers, restaurants, parks, entertainment, and major roadways. Whether you're commuting to work or exploring everything Central Florida has to offer, this location puts you close to it all. This inviting home combines spacious living with exceptional convenience, making it an outstanding rental opportunity. Don't miss your chance to call this Winter Park gem home—schedule your private tour today!
Listing is courtesy of: TRANSCEND REALTY
WINDWARD SQUARE SEC 3 - O6416235 - 2304 INAGUA WAY #2304, WINTER PARK, FL 32792 6 Days on yellowkey
$1,750 | Condo | 2 beds | 1.0 baths
Welcome to this charming 2 bedroom, 1 bathroom corner unit in Winter Park, FL. This single-story home features ceramic tile flooring throughout, perfect for easy maintenance. The freshly painted interior complements the renovated kitchen and bathroom, giving the space a modern and updated feel. Enjoy the privacy of the fenced backyard, ideal for outdoor entertaining or relaxing. Located in the established community of Winward Square with access to a community pool and tennis courts, this home offers both convenience and comfort. Don't miss out on this opportunity to live in Seminole County in this lovely property. Sorry Pets are not permitted. *Washer and dryer are in as/is condition and for tenant convenience only *Tenant is required to carry Renters Insurance If approved for this home, new tenants must pay a $200.00 lease coordination fee due at the same time as the security deposit payment. *RESIDENTS BENEFIT PACKAGE* Residents are enrolled in the Resident Benefits Package (RBP). There is an additional $35.00 a month charge for this added to the advertised rent and is considered additional rent. RBP includes HVAC air filter delivery, utility concierge services making utility connection a breeze during your move-in, our best-in-class resident rewards program, and much more! More details upon application
Listing is courtesy of: CT HOMES REALTY CORPORATION
PARK WEST CONDO - O6415216 - 350 CAROLINA AVE #407, WINTER PARK, FL 32789 6 Days on yellowkey
$2,895 | Condo | 2 beds | 2.0 baths | 1 gar
Experience maintenance-free living in this spacious 2-bedroom, 2-bath condominium offering 1,529 square feet in the gated Park West community in the heart of Winter Park. Located on the top floor, this spacious residence features vaulted ceilings, hardwood flooring, quartz countertops, stainless steel appliances, walk-in closets, a soaking tub, a stacking washer and dryer, and charming Juliet balconies. Residents enjoy exceptional amenities, including a community pool, tennis courts, clubhouse, and an assigned garage parking space. Water service is included in the rent. Park West is across the street from the weekly Winter Park Farmers' Market, and one block from Park Avenue; you'll have easy access to boutique shopping, highly renowned restaurants, the SunRail station, and everything that downtown Winter Park offers. Cats will be considered on a case by case basis with a non-refundable pet fee and monthly pet rent. Prospective tenants are subject to the Park West Condominium Association approval process and associated application fee.
Listing is courtesy of: FLORIDA ONE REAL ESTATE LLC
COLONIES - S5150999 - 3045 AARON BURR AVE #12D, WINTER PARK, FL 32792 6 Days on yellowkey
$1,650 | Condo | 2 beds | 2.0 baths
Condominium located in The Colonies in Winter Park. Conveniently situated near UCF (University of Central Florida) and Full Sail University, with easy access to shopping centers, major highways, restaurants, and Orlando's world-famous theme parks. Just 11 minutes from Orlando International Airport (Orlando International Airport).This cozy 2-bedroom apartment is perfectly located for quick access to everything Orlando. Featuring new flooring and a clean, fresh interior, it is ideal for any lifestyle.
Listing is courtesy of: LPT REALTY, LLC
WINTER PARK PINES UT 5 - O6415814 - 418 R GILBERT RD, WINTER PARK, FL 32792 6 Days on yellowkey
$4,000 | Single Family Home | 3 beds | 3.0 baths | 2 gar
Beautifully renovated solid block home on a quiet street in highly desirable Winter Park Pines! This property features fresh exterior paint, updated lighting, a newly paved courtyard, and a bright open floor plan. The stunning kitchen offers modern cabinetry, quartz countertops, and brand-new stainless steel appliances, flowing seamlessly into the dining and family rooms. The sun-drenched Florida room is lined with windows that brighten the entire living space. Complete with a dry bar and its own mini-split AC unit, it offers flexible space for entertaining, relaxing, or creating your dream retreat. The split floor plan includes three generously sized bedrooms and three full renovated bathrooms, with a private primary suite with walk-in closet off the family room and the additional bedrooms and bath located on the opposite side of the home. The attached two-car garage offers excellent potential to be converted into a fourth bedroom, utilizing the existing full bathroom to create a private mother-in-law suite or guest quarters. Additional upgrades include new flooring, trim, doors, fixtures, and fresh interior paint. Create your own outdoor oasis with a newly paved patio and large fenced backyard with room for a pool. Ideally located near downtown Winter Park, Park Avenue shopping and dining, Cady Way Trail, and zoned for top-rated schools.
Listing is courtesy of: SOTERA LIVING
LAKE KILLARNEY CONDO - O6415735 - 151 N ORLANDO AVE #238, WINTER PARK, FL 32789 7 Days on yellowkey
$2,750 | Condo | 2 beds | 1.0 baths
Experience lakefront living at its finest in this exceptional Winter Park condo overlooking beautiful Lake Killarney. Enjoy breathtaking sunset views from your private waterfront retreat, complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers unparalleled walkability. Stroll to Park Avenue's renowned boutiques, restaurants, and nightlife, catch a movie at Regal Cinemas, or conveniently shop at Publix and Trader Joe's. With countless restaurants, bars, and everyday amenities just steps away, you'll enjoy the perfect blend of tranquil waterfront living and vibrant urban convenience. Whether you're boating on the lake, lounging by the pool, or taking in the spectacular evening sunsets, this is a rare opportunity to enjoy one of Winter Park's most desirable waterfront lifestyles.
Listing is courtesy of: COLONIALTOWN REALTY
SYLVAN HEIGHTS - A4696508 - 1741 GOODRICH AVE, WINTER PARK, FL 32789 8 Days on yellowkey
$3,600 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Virtually Staged. Charming 3-bedroom, 2-bath home in highly desirable historic Winter Park, situated on a large fenced lot with mature oak canopy, lush landscaping, and inviting outdoor living spaces. This well-maintained home offers a spacious living room, separate dining area, screened rear patio, large wooden deck with lighting, and a private fenced backyard perfect for relaxing or entertaining. NOT FURNISHED! The primary suite features two walk-in closets, double vanity sinks, a Jacuzzi tub, and a double walk-in shower. A guest suite with a closet and shared bathroom. The 3rd room has a closet and can be used as a bedroom or office. Additional features include ceiling fans throughout, generous closet space, newer bedroom flooring, fresh interior and exterior paint, a security system ready for activation, washer and dryer in the two-car garage, utility sink, and newly finished epoxy garage flooring. Major updates include roof and A/C replaced in 2021, and the refrigerator, stove, and microwave replaced in 2022. Lawn maintenance, lawn spraying, and pest control are included in the monthly rent. Located near AdventHealth Winter Park, Casa Feliz, Leu Gardens, Rollins College, Park Avenue shopping and dining, Baldwin Park, East End Market, Winter Park Farmers Market, Enzian Theater, city parks, museums, Winter Park Racquet Club, Interlachen Golf & Country Club, YMCA, Winter Park Boat Tours, the Winter Park Chain of Lakes, and Downtown Orlando. Zoned for highly rated local schools, including Brookshire Elementary, Glenridge Middle, and Winter Park High, with many nearby school options. Surrounded by historic homes and multi-million dollar estates, this property offers an excellent opportunity to enjoy the Winter Park lifestyle in a prime location. Lease Terms: Owner pays for lawn maintenance, lawn spraying, and pest control. Tenant is responsible for utilities, cable, and internet. First month’s rent, last month’s rent, and security deposit required. Credit and background check required for each applicant on the lease. Small pets may be considered with owner approval and an additional non-refundable pet fee. No smoking or vaping permitted. Current tenant leaving 7/2026. 24-hour notice to schedule a showing.
Listing is courtesy of: JOHN HARDING REALTY