Winter Park Single Family Homes For Rent - 36 homes

Remarks: Located in the heart of Winter Park, Winter Park Pines is a well-established neighborhood known for its convenience, school zoning, and access to outdoor living. A place to slow down, where evening walks feel like something out of a storybook, and the Cady Way Trail is just steps from your back door for morning runs, bike rides, and everything in between. One of the standout features is having the Cady Way pool, pickleball courts, and beach volleyball courts all just a short walk away. The home is zoned for Brookshire Elementary School, Glenridge Middle School, and Winter Park High School, making this location a consistent choice for buyers prioritizing long-term value. In addition to the location, the home benefits from key updates already completed, including a 2022 roof, 2021 HVAC system, updated windows installed in 2017, along with an updated kitchen and bathrooms, offering peace of mind and modern functionality for the next owner. Ideally positioned to enjoy the Winter Park lifestyle. Close proximity to Park Avenue’s boutique shopping and exceptional dining, while the University of Central Florida, Rollins College, and Full Sail University are all within easy reach. AdventHealth Winter Park and Orlando International Airport are also close by, making both daily routines and travel simple. This is a home that delivers on every level, location, lifestyle, and lasting quality.

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

Listing Agent: Melissa Johnson (407-681-4393)

Remarks: Furnished turn-key luxury lake-view home in Winter Park where comfort meets style. This beautifully designed 4-bedroom / 2-bath one story home features an open-concept layout, curated artwork, lush front and backyard spaces, a wood deck, and an outdoor kitchen perfect for entertaining. Ideally located just minutes from Orlando's top attractions, hospitals, airports, Winter Park's cultural gems, and the scenic Chain of Lakes, this home is perfect for professionals, creatives, and families seeking a refined long-term stay. The neighborhood offers an exceptional lifestyle with walking trails, pickleball and tennis courts, playgrounds, dog parks, proximity to Baldwin Park, and Winter Park Pines Golf Club.

Listing is courtesy of: SOTERA LIVING (407-725-9660)

Listing Agent: Benjamin Cole Iv (407-399-0629)

Remarks: Characterized by its expansive layout and modern charm, 4571 Kawilla Crest Place in Winter Park, FL, offers an extraordinary living experience with six spacious bedrooms and five full bathrooms. Boasting a generous 3,676 square feet, this property is perfect for those who appreciate space and comfort. The open-concept design fosters a seamless flow between living areas, creating an inviting atmosphere for both relaxation and entertaining. Large windows throughout the home allow natural light to flood in, highlighting the elegant interior finishes. Each of the five bathrooms is thoughtfully designed with style and convenience, ensuring a comfortable experience for everyone. The well-appointed bedrooms provide ample space for rest and rejuvenation, making this home ideal for larger groups or families. In addition to the main living space, the home features a private mother in law suite with its own separate entrance. This self-contained suite includes a bedroom, bathroom, laundry area, and full kitchen, making it ideal for extended family, guests, or additional living space. Nestled in the serene setting of Winter Park, this residence offers a perfect balance of tranquility and accessibility. With its prime location, residents will enjoy proximity to local amenities, dining, and entertainment options. Embrace the opportunity to make this stunning property your next home, where spacious living meets unparalleled comfort. Discover the perfect blend of style and functionality at this remarkable address. Prospects must view the home prior to applying. Tenant requirements include: minimum gross household income of 2.5x the monthly rent amount, a favorable background and credit screening, favorable rental history and references, proof of income/employment. A security deposit (same as rent) is due upon applicant approval to mark listing as Pending. First month rent and last month's rent are due 7 days prior to lease start date. The owner does not allow smoking in or around the home. Tenants are required to provide proof of renter's insurance. Tenants are responsible to pay all utilities and put in their name, where applicable. Please review these requirements BEFORE requesting a showing. After viewing, listing agent will provide application link, upon request. If a tenant-prospect chooses to apply for one of our rental properties, that DOES NOT guarantee that the prospect's application will be approved. The application fee is NON-REFUNDABLE. Tenant approval is contingent on a lease start date within 30 days of approval.

Listing is courtesy of: HOST MANAGEMENT GROUP LLC (407-680-1234)

Listing Agent: Lukasz Sokolowski (407-680-1234)

Remarks: Be careful of scams. Only talk to a license agent. This is 2 bedroom not a 4 bedroom. Welcome to your new 2 bedrm+ office/ 2 bath/ 2 car garage home in charming Winter Park, FL. This inviting property offers an ideal location surrounded by lakes and green space, restaurants and grocery stores, making everyday conveniences just a short drive away. Your commute to work or school is easy with 417, 436, and Aloma Ave just minutes from this quiet neighborhood. This property features a comfortable living space with essential amenities to enhance your lifestyle. Please note that utilities such as electricity, Water/Sewer, cable, and internet are not included in the rent, but trash service, lawn maintenance, tennis courts and access to the lake (for non-motorized watercraft) are included. Don't miss out on this fantastic opportunity to experience the vibrant life in Winter Park! Schedule a viewing today to make this property your new home.

Listing is courtesy of: TOP VALUE PROPERTIES LLC (407-927-2098)

Listing Agent: Robin Leedom-Hafen (407-927-2098)

Remarks: Welcome to this beautifully maintained 4-bedroom, 2-bathroom home offering 1,677 square feet of comfortable living space in a desirable Winter Park neighborhood. Featuring a split-bedroom floor plan, multiple living areas, and a spacious Florida room. The updated kitchen offers stainless steel appliances, wood cabinetry, and a cozy dining area. The private primary suite includes a walk-in closet and a beautifully renovated ensuite bathroom, while three additional bedrooms provide plenty of space for family, guests, or a home office. Enjoy the bright Florida room overlooking the fully fenced backyard, complete with a fire pit, grilling area, and swing—perfect for relaxing or entertaining outdoors. Conveniently located near top-rated Winter Park schools, SR-417, Full Sail University, UCF, Orlando International Airport, Costco, Target, shopping, dining, and more, this home offers the ideal combination of comfort and convenience. Don't miss this opportunity to lease a move-in-ready home in one of Winter Park's most sought-after locations! Contact the leasing agent for more information to schedule a viewing, or for help with any questions regarding the leasing process.

Listing is courtesy of: REAL BROKER, LLC (407-922-8986)

Listing Agent: Nga Nguyen, Llc (417-234-7848)

Remarks: Discover refined living in the heart of Winter Park in this beautifully appointed 4-bedroom, 2.5-bathroom single-family pool home. Immediately to the right of the entryway, a beautiful private office provides a convenient and quiet space for working from home or studying. Filled with natural light, the home features an inviting open layout, and a spacious living area centered around a cozy fireplace. The stylish kitchen showcases light gray cabinetry, sophisticated gold-tone accents, a center island, and generous space for cooking and entertaining. The primary suite offers a peaceful retreat with a spa-inspired bathroom featuring a soaking tub and a spacious walk-in closet. Outside, enjoy a private oasis with a sparkling pool and a balcony overlooking the outdoor living area—perfect for relaxing or entertaining. Additional highlights include a two-car garage, an oversized driveway with ample parking, and an excellent location on a residential street in highly desirable Winter Park. Available for a minimum lease term of seven months. Schedule your private showing today.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Patricia Zimath, Llc (321-318-1050)

Remarks: 3/1, Carport, Single Family Home, Living Room, Dining Room, Eat in Kitchen, Stainless Steel Appliances Included: Stove, Microwave, Refrigerator, Dishwasher, Disposal, Inside Utility Room with Washer and Dryer Hookups, Laminate Wood Flooring & Ceramic Tile Throughout, Fenced Backyard, Pets Ok Upon Owner's Approval, NO SMOKING, Year Built: 1957/1300 Sqft.

Listing is courtesy of: LEGENDS REALTY (407-333-1010)

Listing Agent: Tina Lopez (407-333-1010)

Remarks: Located in the highly sought-after Winter Park High School district, this beautifully maintained 3-bedroom, 2-bath home in Laurel Springs provides comfort, space, and convenience. The bright and inviting living area features tile and an open, welcoming feel. Enjoy year-round indoor-outdoor living in the expansive 400+ sq. feet. enclosed patio overlooking a fully fenced backyard—perfect for entertaining, relaxing, or family gatherings. Ideally situated with easy access to shopping, dining, parks, and major highways. Move-in ready!!!!

Listing is courtesy of: JOY ESTATE ENTERPRISE INC (321-754-9131)

Listing Agent: Liu Zhang (917-892-2868)

Remarks: LOCATION! LOCATION! LOCATION! Home well positioned on large 0.28 acre lot in 32789. Gorgeous two bedroom home right in the heart of Winter Park , that just had a new roof put on.. At just a ten minute drive from Orlando, this home is in a very convenient location for anyone who wants to be in and out of the city whenever they'd like. Beautiful interior, with original wood flooring throughout. Tile in the spacious open kitchen that opens into the living room, giving this home a wide-open layout. Enjoy, the peaceful, secluded feeling when lounging on the deck in the generous backyard during warm summer nights. Large, fenced backyard. Lake Killarney access for kayaking and canoeing.

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Vincent Paige, Pa (407-256-8190)

Remarks: Gorgeous 3/2 Mid-century Modern Style Home with a Covered Patio and a Large Backyard in the Desirable Albert Lee Ridge Community - Winter Park! Available Now! Nestled in Lake Wilderness is a hidden gem, with homes only lining one side of the lake offering picturesque sunsets and views. This gorgeous home welcomes you into a bright and airy living space with a floor plan that offers versatility, privacy and convenience. Tile flooring flows throughout the main living areas and cozy carpet flooring in the bedrooms. Near the entrance you will find a spacious bedroom which can be used as an office, studio or additional living space. The updated kitchen boasts modern stainless steel appliances with plenty of countertop and cabinet space. Additionally, there's a home bar with a wine fridge so you can prepare your favorite drinks during the hot summer days. The large dining room has access to the covered patio, which is perfect for al fresco dining, cookouts and outdoor activities. You can relax and unwind on the patio overlooking the backyard, oak trees and the beautiful lake view. The master bedroom is a true retreat offering space for relaxation and comfort, plus an ample walk-in closet. The secondary bedroom is also very spacious with a shared bathroom for convenience. This home also offers an inside utility room (Washer and Dryer hook-ups only) and a 1 car garage with an extended driveway for extra parking. Don't miss it! Great location within walking/biking distance to the key attractions in Winter Park: Ravaudage, Winter Park Villages, Lakeside Crossings, Hannibal Square and Park Ave. Easy access to major roads and a short drive to Downtown Orlando offering a range of shopping, restaurants and entertainment options. Pets will be considered. All residents are enrolled in the Resident Benefits Package which includes AC filter delivery, utility concierge, our best-in-class resident rewards program, and much more! More details in our Rental Selection Criteria or upon application. NO SIGHT UNSEEN APPLICATIONS. [21G]

Listing is courtesy of: VERANDAH PROPERTIES INC (407-855-0331)

Listing Agent: Rebeca Lima (407-800-5654)

Remarks: Take a look at this beautiful home, Clean and Move-In Ready, featuring 3 bedrooms, 2 bathrooms, 1,266 car garage and approximately 1,266 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance reqrd, Pool service (if applicable) is $150/mo, Septic System (if applicable)- $35/mo; Admin Fee - $150 after lease is generated.

Listing is courtesy of: TAH FLORIDA LLC (844-874-2661)

Listing Agent: Laidy Mataushek (844-874-2661)

Remarks: Gorgeous 5-bedroom /6-bathroom Luxury Estate with Guest House & Pool in Winter Park This stunning two-story home offers the perfect blend of luxury and comfort right in the heart of Winter Park. At the center of the home is a beautiful open kitchen outfitted with high-end appliances, solid wood cabinets, and granite countertops . A true chef’s layout that flows into the living spaces. You'll love the elevated details throughout, from the elegant crown molding to the beautiful flooring. The backyard is a private retreat, featuring an inviting in-ground concrete pool, an outdoor shower, and a separate guest house that offers fantastic flexibility. Location-wise, it doesn't get better: you're within premier Winter Park school zones and just a short walk away from the area's best boutiques and restaurants. Available for long-term lease.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Magdalena Cuprys (305-850-8932)

Remarks: Welcome home to this charming residence tucked away on a quiet cul-de-sac in a welcoming neighborhood. Situated on an oversized 0.23-acre lot, this home offers plenty of outdoor space to relax, entertain, or simply enjoy the peaceful surroundings. Inside, the thoughtfully designed split-bedroom floor plan provides both comfort and privacy. The updated kitchen features beautiful granite countertops, stainless steel appliances, and a window overlooking the spacious backyard, making meal preparation both functional and enjoyable. The bathrooms have also been tastefully updated with granite finishes for a modern touch. The inviting living room is the perfect setting for movie nights or entertaining guests. Additional conveniences include a digital peephole at the front door, an epoxy-coated garage floor, and a powered storage shed offering extra space for hobbies, tools, or equipment. This well-maintained home combines modern updates with practical features in a desirable location, making it an excellent place to call home. Schedule your private showing today and discover everything this property provides.

Listing is courtesy of: D & D PROPERTY MANAGEMENT SOLUTIONS LLC (407-434-1693)

Listing Agent: Allan Dion (407-434-1693)

Remarks: WINTER PARK 4BR/2BA, Single Story, Built in 2016. Located in the GATED COMMUNITY of Enclave At Aloma. Fantastic open floor plan. Plank wood-looking ceramic tile throughout the entire home. Loads of options. House was extended 4 feet to increase the size of dining room, great room, and master bedroom. 10' x 40' Covered Lanai in the rear. Center Island with Pendant Lighting in the Kitchen. Stainless Steel Appliances, Upgraded Cabinets, Crown Molding. Solid Surface Counters throughout the home. Volume Ceilings & Recessed Lighting. Master Bathroom has dual sinks, a huge walk in shower with a seat, and private toilet closet. Inside utility room with washer/dryer hook-ups. Easy access to the major highways 417, 426, 436, and a short commute to downtown Winter Park. First, Last & Security are required. No smoking or vaping. No pets

Listing is courtesy of: LAKEFRONT REALTY, INC. (407-592-6700)

Listing Agent: Bill Cook (407-592-6700)

Remarks: Welcome to an extraordinary two-story, 4-bedroom, 5.5-bath executive estate nestled in one of Winter Park's most sought-after neighborhoods. Designed with timeless elegance and modern convenience, this expansive home effortlessly blends luxury, comfort, and versatility. Inside, vaulted ceilings create a grand sense of space, while multiple living areas offer flexibility for both formal entertaining and casual gatherings. The gourmet kitchen is a chef's dream, complete with an enormous walk-in pantry, high-end appliances, and seamless flow into the dining area. Entertain in style with a wet bar and food service station, perfect for hosting elegant dinners or festive celebrations. Master Suite is an expansive sanctuary that features a spa-like bathroom equipped with a soaker tub, walk-in shower, His and Her vanities Step outside to your private heated lap pool, perfect for fitness or relaxation. The backyard retreat is surrounded by lush landscaping an ideal oasis for quiet relaxation or sunny Florida afternoons. A first-floor bedroom with en-suite bath adds convenience for guests or multi-generational living. Perfectly situated near Audubon Park and Baldwin Park, this home offers unbeatable access to top-rated schools, including Audubon Park K-8 & Winter Park H.S. Ideally situated near Downtown Orlando, Rollins College, hospitals, renowned restaurants, and boutique shopping, making it a prime location for those seeking convenience and accessibility. Explore numerous community parks, perfect for those who enjoy an active outdoor lifestyle. An area rich in culture with nearby museums to explore and learn. This is more than just a home it's a lifestyle. Experience the best of Winter Park living: elegant, elevated, and effortlessly connected. Pets negotiable with owner approval. Additional fees may apply.

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Raquel Elliott (407-921-3772)

Remarks: Come see this 4 bedroom 2 bath in the beautiful Winter Park neighborhood of Eastbrook. This home is completely move in ready with granite counter-tops and stainless steel appliances in the kitchen and new microwave. Large open kitchen/living room. Spacious bedrooms with lots of closets and storage space. Updated modern light fixtures and fans adorn the rooms throughout the home. Home is tiled and has new laminate throughout. Fenced backyard with huge screened in back porch.

Listing is courtesy of: ABSOLUTE REALTY GROUP, LLC (407-673-1400)

Listing Agent: Courtney Davis (407-493-8329)

Remarks: Welcome to 301 S Capen, a 3-bedroom, 2-bath home located just minutes from Park Avenue. Inside, you'll find a bright and inviting kitchen featuring large bay windows and ample space for a breakfast table. The adjoining family room provides a comfortable gathering space and offers convenient access to the laundry room and attached one-car garage. Down the hall, you'll find three bedrooms with brand-new carpeting and easy access to the spacious backyard, offering plenty of room to relax or entertain outdoors.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Jordan Heidrich (407-223-3495)

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: Virtually Staged. 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 interior spaces updated, 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, the downstairs has a bonus room which is perfect for a den or playroom and a convenient interior laundry room. The lot is 6,750 sqft and is fenced and gated (electronic with remotes) offering a nice new patio of clay pavers, a carport, and large backyard. This 1,774 sqft of living space is perfect for the tenant who wants quality, style and convenient location. This one is MOVE IN READY AND WAITING FOR YOU. There is a $99 for each adult application fee and once approved the first & last month’s rent will be due along with the security deposit and any applicable pet fee and deposit.

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Johnny Hurlburt (407-579-3168)

Remarks: Fantastic 4 Bed 2 Bath Winter Park Home with 2-car garage! Located in a highly desirable Winter Park area. Large living room/dining room combo, a large separate den area. The home has a large fenced-in backyard. Lawn care is included. Walking distance to the Cady Way Trail. *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 (with approval and a non-refundable pet fee).

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

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