Winter Park Single Family Homes For Rent - 33 homes

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: 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. Rent includes lawn, pool and pest care. The home is equipped with solar panels, which help keep electricity costs low. 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: 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 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: 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: 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: WINTER PARK RENOVATED -WHAT MORE CAN YOU ASK FOR Mid Century Modern-A+ NEIGHBORHOOD & SCHOOLS. Just 1 block to Baldwin Park & Audubon Park and minutes to Downtown Winter Park, College Park and Downtown Orlando. Gas Cooking, Marble countertops 3 bedroom/2 bath with TONS of NATURAL light and CHARM plus TONS of outdoor living space! This home has Luxury Vinyl Plank Floors, Ceiling Fans, Stainless Steel Appliances, Washer and Dryer TOO! SOLAR with battery backup! Set Flat Fee of $150 for electric. Lawncare and washer/dryer included in rent! Hurry, This home will rent fast!

Listing is courtesy of: REALTY PROS UNLIMITED INC (407-473-1526)

Listing Agent: Michelle Morrow (407-473-1526)

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)

Remarks: Welcome to this spacious 5-bedroom, 3-bathroom home designed for comfort, functionality, and flexible living. One of the home’s standout features is a private area that includes two of the bedrooms and a full bathroom, offering added privacy and versatility. This thoughtfully designed layout creates the feel of two living spaces within one home, making it ideal for multi-generational living, extended guests, or anyone working from home who desires a more private area, while remaining part of the main residence. Step outside to enjoy the expansive backyard featuring a sparkling swimming pool—the perfect setting for relaxing, entertaining, and enjoying Florida’s outdoor lifestyle year-round. Conveniently located near shopping, dining, schools, and major highways, this home combines comfort, flexibility, and an excellent location.

Listing is courtesy of: JUPITER PROPERTIES, INC (386-547-6161)

Listing Agent: Nancy Conde (407-486-6611)

Remarks: Available on July 29th 2026!! CHARMING AND UNIQUE two bedrooms /one bath home in the heart of Winter Park down street from Mead Botanical Gardens. This home still has a lot of its original charm and features beautiful wood floors extending through out. Tons of natural light that flood the interior from all the windows that wrap the entire exterior, open and airy floor plan that makes it feel double the size. Kitchen features gas stove and refrigerator. Also enjoy a great Florida room off the kitchen overlooking the huge back yard. WALK TO PARK AVENUE, ROLLINS COLLEGE, LAKE VIRGINIA, AND MORE. All applicants are required to do a credit and background check. Renters insurance is required. **Pets allowed 60lbs max** Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents can opt out of the master policy by providing proof of their own policy that meets minimum requirements.

Listing is courtesy of: 407 PROPERTIES (407-545-2594)

Listing Agent: Steven Simpson (407-545-2594)

Remarks: Nestled beside Cady Way Park & Trail, this charming home offers an unbeatable location in a quiet, established neighborhood on a peaceful tree-lined cul-de-sac. Enjoy easy access to top-rated Winter Park schools, Winter Pines Golf Club, Showalter Field, AdventHealth Winter Park, Baldwin Park, Downtown Winter Park, and a wide variety of shopping, dining, and entertainment. Inside, you’ll find beautiful terrazzo floors throughout much of the home, with ceramic tile in the spacious family room. The bright kitchen features a window overlooking the large backyard, solid wood cabinetry, and a cozy eat-in dining area. Tastefully updated bathrooms add a fresh, modern touch. The flexible floor plan includes: * Living room * Dining area * Eat-in kitchen * Expansive family room with French doors leading to an outdoor deck and large fenced backyard. Zoned for highly sought-after schools: * Brookshire Elementary * Glenridge Middle School * Winter Park High School This home combines a prime location, comfortable living spaces, and excellent schools—making it a wonderful place to call home.

Listing is courtesy of: LOVEJOY PROFESSIONAL REALTY, INC (321-614-0588)

Listing Agent: Paul Chisholm (407-590-2997)

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: Welcome home to this beautifully maintained rental in one of Winter Park's most desirable neighborhoods, zoned for top-rated schools! This spacious 3-bedroom, 2-bath residence features a desirable split-bedroom floor plan, a 2-car garage, and an indoor laundry room complete with a brand-new washer and dryer. The interior has been freshly painted, giving the home a bright, clean, and move-in-ready feel. Designed for both comfortable living and entertaining, the home offers separate formal living and dining rooms, along with a spacious family room featuring a cozy fireplace. The kitchen boasts ample cabinet and counter space, a breakfast nook, and opens seamlessly to the family room, creating the perfect gathering space for family and friends. Step outside through the sliding glass doors to the oversized 23' x 12' screened porch overlooking a fully fenced backyard—ideal for relaxing, entertaining, or enjoying Florida's beautiful weather. Pets are welcome! Conveniently located just minutes from shopping, dining, Rollins College, Full Sail University, Downtown Winter Park, major roadways, parks, and everything Central Florida has to offer. Don't miss this exceptional rental opportunity! Schedule your private showing today, homes in this highly sought-after Winter Park location lease quickly.

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

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

Remarks: Fabulous rental opportunity in the sought-after Winter Park School District. This 4-bedroom, 2.5-bath, 2219-square-foot home also boasts glorious lake views from the massive 1,000-square-foot Florida room, ideal for entertaining and enjoying the Florida lifestyle on an expansive ½ acre lot. Ready for move-in, the home is full of natural light pouring in and shining onto the wood flooring throughout the home. There are opportunities to create a multitude of spaces that serve your needs for a home office, craft room, or playroom. The updated open kitchen offers views of the family room, Florida room, and the dining room with solid maple cabinets, granite counters,china-front cabinetry, custom tile backsplash, and stainless steel appliances. The kitchen also has programmable “smart lights”. The master bedroom offers ample storage space, a walk-in shower, and a walk-in closet. There are three additional bedrooms and an additional bathroom. There is a large storage shed and well/pump system for irrigation and a massive backyard for a variety of activities. The 8-zone irrigation system is run by a ground well and pump system, which will equate to savings on the water bill. Start enjoying life in the quiet community known as Arrowhead Cove with Winter Park Schools, as well as charter and private schools in the area, including Trinity Prep, Full Sail, and UCF.

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Julia Magnani (305-610-1876)

Remarks: Beautiful pool home for rent in Winter Park located in the established Eastbrook community with NO HOA. This home offers 3 bedrooms plus a versatile bonus room, 2 bathrooms, approximately 1,770 sq ft of living space, a 2-car garage, extended driveway, and a private screened pool with fully fenced backyard. Inside, you’ll find a bright and functional layout with comfortable living and dining areas, updated kitchen with granite countertops and modern cabinetry, plus updated bathrooms with clean finishes. The bonus room offers flexibility for a home office, gym, playroom, or additional living space. Major updates include roof replaced in 2018, fully paid solar panels installed in 2020, water heater 2019, and A/C replaced in 2013. Conveniently located near Park Avenue, Rollins College, Full Sail University, University of Central Florida, shopping, dining, and major highways. First month’s rent, last month’s rent, and security deposit required prior to move in. Background and credit check required through RentSpree at tenant expense ($50 x adult over 18 years old). Preferred credit score 550+. No prior evictions. Pet restrictions apply.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)

Listing Agent: Alexa Monasterio Flores (786-915-9294)

Remarks: Leasing nicely furnished 2 bedrooms, 1 bath, living room, dining room and kitchen in 3 bedroom / 2 bath home. Each bedroom has queen size bed and closet. The kitchen is fully equipped including dishes. The living room has a sofa and tv.The dining room has a table with 4 chairs. The porch has some chairs and a small table. Outside in the back yard is a table with 4 chairs - picnic in your own park like back yard. Ready to move in on September 1, 2026.

Listing is courtesy of: BLACKFIN REALTY LLC (407-947-9722)

Listing Agent: Scott Banta (407-947-9722)

Remarks: Welcome home to Winter Park living at its finest in this beautifully updated one-story home where comfort, convenience, and charm come together. From the moment you enter, you'll notice the bright, freshly painted interior, spacious layout, and modern touches throughout—including new updated bathrooms, landscaping enhancements and brand-new stainless-steel appliances. The attached two-car garage adds everyday ease, while the included washer and dryer. Step outside to your private backyard retreat, where a peaceful water view and inviting fire pit creates the perfect setting for morning coffee, weekend gatherings, or quiet evenings under the stars. Professional landscaping and pest control are also included, so you can spend less time on upkeep and more time enjoying your home. Ideally located near Downtown Winter Park, Park Avenue, local coffee shops, restaurants, grocery stores, entertainment, and daily conveniences, this home also offers quick access to Maitland, Casselberry, Orlando, I-4, and SR-417. Zoned for Seminole Country Schools. If you're searching for a stylish, low-maintenance rental in a prime location, this Winter Park home is ready to welcome you. Schedule your showing today!

Listing is courtesy of: CENTRAL FLORIDA REALTY MANAGEMENT LLC (407-542-4403)

Listing Agent: Kevan Patel (407-491-3559)