Winter Park Single Family Homes For Rent in Winter Park - 5 homes

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: Fully renovated with stylish charm, this four-bedroom, three-bath home is in one of the most desired neighborhoods in Winter Park, the Tree Streets. A brick drive and path welcome you into this open living plan on a large 75-foot by 150-foot lot with tons of room to grow. Warm wood floors throughout and this home enjoys an open kitchen family plan with spaces that are flexible for your needs. The kitchen has custom cabinetry, quartz countertops, subway glass tile, GE stainless appliances including natural gas range and loads of storage. French doors lead to spacious patio and generous backyard. The owner’s retreat was seamlessly added with 9-foot ceilings, large walk-in closet and beautiful primary bath retreat with dual vanities, separate soaking tub and water closet. The home has lovely natural light throughout. Other features include newer Trane air conditioning, electric panel in 2010, updated plumbing, level five dry wall finish, new paint inside and out, upgraded lighting package, all baths renovated, generous closets, updated garage door, updated windows and treatments, and mature landscaping. Just a short distance to the YMCA, Phelps Park, Lakemont Elementary School and zoned for Winter Park High School. Close to all the amenities Park Avenue offers and the perfect location.

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

Listing Agent: Alison Mosley (407-304-6458)

Remarks: One Story home in Winter Park Pines with 4 bedrooms and 3 full baths! Large Screened Porch and fenced rear yard. Quiet street. Stainless steel appliances: Refrigerator, Smooth-top Range/Oven, Dishwasher. Lawn Care included! W/D hookups in Laundry room. A/C replaced in 2022. Home re-piped in 2022. Move-in Ready Home! Convenient Winter Park Location Only Minutes from Baldwin Park, Park Avenue, Winter Park High School, etc. Realtor is owner of the home. Interior repainted 2/2026. Fireplace in family room is not available for use.

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

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

Remarks: Winter Park 4 Bedrm Home for Rent! Priced Low, Call Now!, 2 Car Carport, Bonus Room Too!, Eat In Kitchen, JUST 20 MINUTES To: Downtown Orlando, JUST 30 MINUTES To: The Orlando Airport, CONVENIENT To: 436, CONVENIENT To: Major Roads, Shopping & Schools, CONVENIENT To: Full Sail University, Stainless Steel Appliances INCLUDED, Blinds INCLUDED. The deposit amount is based upon the application results. Pets: OK (Dangerous Pets are not permitted, Pit Bulls, etc.) Priced $2,099.00 for the first 4 months, $2,199.00 for the remaining 8 months (Average: $2,167.00/mo). AVAILABLE: May 19, 2026

Listing is courtesy of: ORLANDO REALTY & PROPERTY MGNT (407-641-5782)

Listing Agent: Jay Myers (407-641-5782)

Remarks: Welcome home to this beautifully maintained 4-bedroom, 3-bath pool home located in Winter Park’s highly desirable Tree Streets neighborhood—an area known for its charming, tree-lined roads and peaceful atmosphere. Situated on an oversized .27-acre lot, one of the largest in the community, this property offers rare space and privacy while still being close to everything Winter Park has to offer. Inside, the home features 1,808 square feet of well-designed living space with an open and flexible layout that makes everyday living comfortable and functional. The remodeled kitchen offers modern finishes, ample cabinetry, and plenty of space for cooking and entertaining. Step outside and enjoy your own private backyard retreat, complete with a sparkling pool, lush landscaping, and a large yard—perfect for relaxing, entertaining, or enjoying the Florida sunshine. Additional features include spacious bedrooms, generous storage, and a layout designed for both comfort and convenience. Located just minutes from Park Avenue, top-rated schools, dining, shopping, and major roadways, this home offers the perfect balance of tranquility and accessibility in one of Winter Park’s most sought-after neighborhoods. Homes for rent in this area are rarely available—schedule your showing today before it’s gone.

Listing is courtesy of: TBRO REALTY LLC (407-403-4322)

Listing Agent: Jorge Perez Gonzalez (321-525-0204)