Winter Park Apartments for Rent - 59 rentals

Remarks: This beautiful three bedroom, two and a half bath townhome is located in the newly developed Grayson Square, a gated community in Winter Park. High-speed Internet and cable are included. There are no rear neighbors, so you will enjoy relaxing on your back porch with a beautiful water view. As you enter the home, the entrance leads to the large kitchen and living area. The kitchen features stainless steel appliances, including a refrigerator, a dishwasher, a range, a microwave, and quarts countertops. The sliding glass doors in the living area open to the covered patio. The half bath is on the 1st floor for easy access for guests. Located on the second floor are the primary bedroom and both additional bedrooms. The primary suite has a large walk-in closet. The primary bathroom features dual vanities and a glass-enclosed standing shower. The other bedrooms allow easy access to the second full bathroom. The home also includes a laundry closet and a one-car garage. Enjoy the community pool and playground area—easy access to major roads, shopping, schools, and entertainment.

Listing is courtesy of: RIVA REALTY GROUP LLC (407-845-1003)

Listing Agent: Vildan Nigro (352-988-3824)

Remarks: Beautiful townhouse in a pool community, near to supermarket and Costco, good school area. High and trey ceiling in the master bedroom with high loft and living room. Beautiful tile floor on first floor

Listing is courtesy of: U S GLORY REALTY (407-222-7801)

Listing Agent: He Gao (407-955-0138)

Remarks: Spacious first floor unit in Waterfall Cove 1 bedroom, charming residential unit , This inviting space offers a comfortable layout with plenty of natural light. Conveniently located near shops, restaurants and parks. It is perfect for enjoying the Winter park lifestyle.

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Yigit Orer (407-948-5347)

Remarks: 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. The main living areas feature classic plantation shutters, while all bedrooms are fitted with blinds, a thoughtful touch that makes every space feel finished and move-in ready. Warm engineered hardwood floors, recessed lighting, and a flowing open layout connect the living room, dining area, and family room with ease. The chef's kitchen is the heart of the home, featuring granite countertops, a large center island, rich wood cabinetry, stainless steel appliances, and a professional-grade range hood, all opening into the spacious family room with its slate tile floors, wood-burning fireplace, built-in shelving, and French doors to the backyard. The primary suite overlooks the pool and rear yard, offering a serene and private feel. Its spa-inspired en suite bath features a dual-sink vanity, a walk-in tiled shower, and a private access directly to the backyard and pool, making it ideal for those who love to start or end the day outdoors. The second bedroom enjoys its own en suite bath. A third full bath serves the remaining bedrooms, beautifully updated with designer gold fixtures, modern vanity, and stylish lighting. The split bedroom layout offers privacy and flexibility for families, guests, or a dedicated home office. Out back, your private oasis awaits with a sparkling pool, concrete deck, lush lawn, and towering mature oaks creating that quintessential Winter Park canopy. Pool and lawn maintenance are included in rent, so you can simply enjoy. The attached 2-car garage includes laundry. No pets. No exceptions.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Drew Henner (407-406-0662)

Remarks: 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 designed for today’s renter, delivering comfort, functionality, and style in a true turnkey living experience. Ideally located just minutes from Park Avenue, Rollins College, and Winter Park’s premier dining, shopping, and entertainment, this property places tenants in the center of one of Orlando’s most vibrant communities while still offering a sense of neighborhood charm and convenience. Its proximity to major roadways and local amenities makes it especially attractive for professionals, families, and relocation clients seeking both accessibility and quality living. This is a high-demand rental opportunity in a low-inventory pocket of Winter Park, and clean, updated homes in this location do not last. Agents are encouraged to bring qualified tenants ready to move quickly. Now accepting applications with expedited approvals available for well-qualified applicants.

Listing is courtesy of: KELLER WILLIAMS GAINESVILLE REALTY PARTNERS (352-240-0600)

Listing Agent: Fredrick Jacobs (352-790-1088)

Remarks: 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 bedrooms, a versatile loft, and a conveniently placed laundry room. A first-floor guest suite adds flexibility for visitors or a dedicated workspace. Outside, a spacious backyard and custom gazebo create an inviting place to unwind. Zoned for Princeton Elementary and positioned for quick, easy access to everything College Park and Winter Park have to offer, this home delivers rare quality and exceptional value for 32789. This home is available immediatly.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Kris Kennedy (813-947-3509)

Remarks: Beautifully maintained home in the highly desirable Winter Park 32789 neighborhood. This charming property offers an inviting floor plan with abundant natural light, spacious living and dining areas, and a well-appointed kitchen with generous counter space and modern finishes. Comfortable bedrooms provide ample storage, and the primary suite offers a private and peaceful retreat. Flexible bonus space is ideal for a home office, playroom, or guest area. Enjoy outdoor living in the private, landscaped fenced in backyard featuring mature trees and plenty of room for entertaining, gardening, or relaxing. Situated on a quiet street just minutes from Park Avenue, top-rated Winter Park schools, Rollins College, shopping, dining, and community parks. A rare opportunity to rent a home in one of Central Florida’s most sought-after neighborhoods.

Listing is courtesy of: URBANISTA BROKERS (407-619-7272)

Listing Agent: Paul Jimenez (407-276-3516)

Remarks: 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 laundry room, new windows and sliding doors that let in tons of natural light. Other upgrades include new doors, trim, fresh interior and exterior paint, and a beautiful paver patio. Outside, enjoy all-new landscaping with fresh sod and a new irrigation system, lawncare is included in the rent. This home also has a new roof, garage door, and a HVAC system. This home is also next to the scenic Cady Way trail, ideal for biking, walking, and running. Zoned for highly rated Winter Park schools: Brookshire Elementary, Glenridge Middle, and Winter Park High School. Call for your showing today! Sorry NO PETS.

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Jackie O'Leary (407-718-0887)

Remarks: 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 with a cozy firepit and large privacy bushes that create a secluded, tranquil retreat—ideal for relaxing evenings or entertaining guests. With a deeded dock and boat lift, you’ll have direct access to the Lake Killarney lifestyle you’ve been dreaming of. Come see this special home and start enjoying the lake life you deserve!

Listing is courtesy of: COLONIALTOWN REALTY (407-896-7300)

Listing Agent: Alexander Scures (407-925-5338)

Remarks: 2-bedroom, 1.5-bathroom, two-story townhouse in Four Seasons Condos of Winter Park. This well maintained townhouse includes a French country kitchen, which has been renovated with a faux tiled backsplash, custom maple cabinets, and complimentary appliances. This unit includes a half bath downstairs and full bathroom upstairs. Windows are double-pane, double-hung with a Pella sliding glass door with built-in blinds that open to a fenced patio. You will find a neutral color palette throughout the townhouse. Open and fenced-in patio located in the back of the unit. The second floor includes both bedrooms, full bathroom, and rear door to exterior staircase. Water, sewer, and landscaping are included. This unit also comes with covered carport space. The Four Seasons Condos are located within the city limits of Winter Park. Community pool and laundry facilities available at the Clubhouse. Close to shopping, restaurants, the Winter Park Medical Center, Cady Way recreational trail and more. Approximate living and total sq ft is 1219. This is a non-smoking unit. Additional HOA application and approval is required. All tenants are enrolled in a Resident Benefit Package for an additional $50/month (details available below). Don’t miss out, contact us today! All information is deemed reliable, but not guaranteed. Listing Brokerage does not discriminate on the basis of race, color, religion, national origin, sex, disability or familial status. All residents are enrolled in the Resident Benefits Package (RBP) for $50.00/month as additional rent, which includes renters insurance, credit building to help boost your credit score with timely rent payments, our best-in-class resident rewards program, $1M Identity Protection, move-in concierge service making utility connection and home service setup a breeze during your move-in, online resident portal for easy online rent payments & maintenance reporting, HVAC air filter delivery (for applicable properties), and much more! More details available upon application.

Listing is courtesy of: WILSON MANAGEMENT GROUP (407-896-1200)

Listing Agent: Amy Spano (407-896-1200)

Remarks: Live in this updated home in Winter Park with 3 bedroom, 2 bathrooms. Large formal living area and a separate family room with dining. Kitchen with Stainless Steel appliances, Granite counter tops throughout, Ceramic Tile and Carpet flooring. Freshly painted interior and exterior. Large, fenced backyard. Laundry-room with Washer/Dryer hookups. *Bonus Amenity Included* - All residents are enrolled in the Resident Benefits Package (RBP) for $49.95/month which includes liability insurance, credit building to help boost the resident’s credit score with timely rent payments, up to $1M Identity Theft Protection, HVAC air filter delivery (for applicable properties), move-in concierge service making utility connection and home service setup a breeze during your move-in, our best-in-class resident rewards program, on-demand pest control, and much more! More details upon application. Pet friendly home (w. approval and non-refundable pet fee).

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Mo Jabr (407-571-1441)

Remarks: 1 Bedroom/1 Bath condo in Winter Park's Parkview Village! Situated just off of 436/South Semoran Blvd & so convenient to UCF, Full Sail University, 417 & more! The living room, dining & kitchen layout flows easily with sliding doors that lead to the screened patio! Fresh interior paint, washer & dryer. Parkview Village offers a pool, clubhouse. Take a look today!

Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)

Listing Agent: Barry Stephens (407-547-6500)

Remarks: This newly update and freshly painted. First floor condo in Winter Park offers a perfect blend of comfort and style and outdoor access ..It features two spacious bedrooms and two bathrooms, providing ample space for relaxation and privacy. The open plan living room and updated kitchen create a welcoming atmosphere, ideal for both entertaining and everyday living.. A standout features of this home is the in-unit washer and dryer a rare item within the complex. Community also has an additional laundry facility of it own. From the living room you can Step outside onto the nice open patio….whether it's for morning coffee or evening cookouts with family and friends. The community pool is walking distance and accessible to all residents. Unit has two parking spaces and plenty of additional guest parking. The condo is ideally located, with plenty shopping and dining nearby. Full Sail University and a newly built HCA Emergency room are minutes away. Commuting is made easy with access onto 436, and the 408 which makes it easy to travel to Downtown Orlando or Winter Park

Listing is courtesy of: KIMBRIDGE REALTY, LLC (407-755-7367)

Listing Agent: Scott Butts (321-239-8509)

Remarks: Charming 2-bedroom, 1.5-bath townhouse located in the highly desirable Hidden Oaks community. This two-story home offers 990 sq ft of comfortable living space. The main floor features a spacious living area that flows into the dining area and kitchen, along with a convenient half bath for guests. Upstairs, you’ll find the primary bedroom with a spacious bathroom, as well as an additional comfortable bedroom. Enjoy a cozy private patio, perfect for relaxing or entertaining, and a low-maintenance. Two reserved parking spaces are conveniently located directly in front of the unit. Community amenities include a pool, sidewalks, and guest parking. Ideally located just minutes from FL-408 and FL-417, offering easy access to Orlando International Airport and Downtown Orlando. Close to shopping, dining, and excellent schools in the Winter Park area. A great opportunity to enjoy comfort, convenience, and community living—schedule your showing today!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Moira Villavicencio (407-301-8030)

Remarks: Gorgeous Modern Home with 4 bedrooms + 3 and a half bath home with numerous upgrades throughout located in desirable Winter Park. This house has a large kitchen that opens to the family room for entertaining. Fantastic kitchen with solid wood cabinets, granite counters, walk-in pantry, stainless appliances, Gas 5 burner stove, built-in microwave, large island, big windows emanating a lot of natural light. The home features hardwood floors throughout the main living area, stairs, upstairs bonus loft, and Primary bedroom. The living room offers a gas decorative fire feature, a separate dining room and a large sliding glass door allowing additional natural light, that leads out to a covered patio and private fenced yard. The downstairs living space also has a fourth bedroom and full bath, an indoor laundry room, and a guest half bathroom. At the top of the stairs is a bonus loft for more living space, 2 bedrooms with a jack-and-jill bathroom, and closets with shelving. Upstairs also has the large primary bedroom with double door entrance, wood floors, plantation shutters on windows as well as the large sliding glass doors that lead out to the private balcony, the walk-in closet has custom built-in shelving, the big bathroom has two separate sinks, large walk-in shower and a separate soaking tub and a toilet closet. Wonderful home for the family and one of the best school districts. The surrounding area offers grocery stores, shopping, parks, easy access to highways, and moments away from Park Ave shopping and entertainment, farmers market, boat tours and so much more.

Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)

Listing Agent: Wendy Calvet (407-276-5024)

Remarks: 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 for students, faculty, and professionals alike. Zoned for highly regarded schools including Aloma Elementary, Glenridge Middle, and Winter Park High School. Enjoy a vibrant lifestyle with easy access to nearby parks and outdoor destinations such as Kraft Azalea Garden and Mead Botanical Garden perfect for relaxing walks and enjoying nature. The renowned Park Avenue is also just a short drive away, offering boutique shopping, dining, and cultural experiences. Conveniently located with quick access to major roadways, downtown Orlando, and Orlando International Airport, this home also places you within reach of Florida’s beautiful east coast beaches, including Cocoa Beach and New Smyrna Beach ideal for weekend getaways. This fully renovated home offers the perfect combination of location, lifestyle, and modern living, making it an exceptional leasing opportunity in Winter Park. Water is included in the rent. Apply here: https://apply.link/oQ8t72Y

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Betsy Breton-Garcia, Pa (407-580-5350)

Remarks: 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 reclaimed Chicago brick fireplace and full-length sliders opening to a resort-style lanai with summer kitchen, wood ceiling, and recessed lighting. Step outside to a private backyard oasis with a sparkling pool, outdoor kitchen area, and no rear neighbors—perfect for entertaining. The first-floor primary suite offers complete privacy with a spa-inspired bath, soaking tub, walk-in shower, and dream closet. The main level also includes a private office, full bath, dining room, laundry room, and generous living spaces. Upstairs features a large loft, rumpus room, four additional bedrooms, and two beautifully designed baths. The oversized two-car garage provides high ceilings, storage, and a flex space ideal for bikes, fitness, or workshop use. Located minutes from Park Avenue dining, shopping, and entertainment, this home delivers luxury, comfort, and an unbeatable Winter Park lifestyle. Professionally managed with exceptional service.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Tab Bish Llc (855-450-0442)

Remarks: 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 restaurants and shopping.

Listing is courtesy of: BHHS FLORIDA REALTY (407-406-5300)

Listing Agent: Troy Hensley (407-406-5300)

Remarks: 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 outdoor space perfect for relaxing or entertaining. Conveniently located near major roadways, shopping, dining, and everyday amenities. Available for immediate occupancy! Schedule your showing today.

Listing is courtesy of: PRIMAC GROUP, INC (407-889-7075)

Listing Agent: Paula Wells (407-463-8792)

Remarks: Unbeatable Location! Don't miss this very rare and exquisite 3 bedroom, 2.5 bath, two-story Executive-Style condo in Winter Park-ideally located just around the corner from N. Orange Avenue, Park Avenue and Rollins College. Nestled in a prime, tucked-away setting, this home has been extensively remodeled with all new plumbing, electrical, duct work, flooring, appliances, and a natural gas line. In addition, two newer HVAC systems were installed in November 2022, offering modern efficiency and reliability. The gated front courtyard, thoughtfully designed by a landscape architect, provides a serene and welcoming entrance, complete with lush foliage, a potted herb garden, wooden bench, and tranquil fountain—creating the perfect first impression for guests. Inside, you’ll find a spacious dining room filled with natural light from a wall of French doors that open directly to the courtyard. A built-in dry bar with two wine refrigerators makes this an ideal space for entertaining, while oak wood flooring throughout the home adds warmth and timeless character. The chef’s kitchen is both stylish and functional, featuring sleek concrete countertops, custom cabinetry, and a premium dual-fuel 6-burner Wolf range. A cozy dinette area includes a built-in terrazzo-topped table and banquette, while a breakfast bar offers additional seating. Just beyond, the living room showcases a clean-burning bioethanol fireplace and dramatic soaring windows with views of the interior screened two-story courtyard. Upstairs, the private primary suite offers multiple closets, a private balcony overlooking the interior courtyard, and a luxurious en-suite bathroom complete with a large walk-in shower with body sprays, towel warmer, and a dedicated laundry room with built-in storage. At the opposite end of the second floor, the front-facing bedroom can also serve as an ideal home office, featuring a custom built-in desk and shelving, along with a screened balcony overlooking the front courtyard—perfect for enjoying your morning coffee or tea. The second floor also includes a third bedroom, a second full bathroom, a linen closet, and a charming sitting area or nook. A private alleyway behind the building provides convenient access to the oversized two-car garage, which features a custom built-in workbench and sink, as well as two dedicated storage closets. This exceptional location allows you to walk to the pleathora of shops and eateries on N. Orange Avneie, Rollins College, Park Avenue, the Winter Park Tennis Center, Azalea Lane Playground, and the brand new Seven Oaks Park, as well as the shops and restaurants along Orange Avenue. Offering the perfect blend of sophistication, comfort, and practicality, this beautifully updated condo is ideal for those seeking a refined, low-maintenance lifestyle in the heart of Winter Park. Full Lawn care by the HOA are included in the rental rate. A small pet may be considered on a case-by case basis. Proof of a renters insurance policy is required to rent this property. Showings by Appointment Only. Must see to fully appreciate.

Listing is courtesy of: FUSILIER MANAGEMENT GROUP (407-476-0476)

Listing Agent: Keith Race (407-536-7223)