Apartments for Rent Near Winter Park High in Winter Park - 15 rentals

Remarks: Bright and freshly updated ground-floor 2-suite condo in a peaceful, well-kept community. This move-in-ready home features new interior paint, new water heater, granite countertops, and durable vinyl plank flooring throughout. The split-suite layout offers privacy and flexibility for roommates or professionals. Zoned for Cheney Elementary, with convenient access to A-rated middle and high schools, plus minutes to Full Sail University and UCF. A perfect blend of comfort, convenience, and value.

Listing is courtesy of: NOBSKA REAL ESTATE LLC (689-276-1593)

Listing Agent: Jiny Lee (407-920-0702)

Remarks: Welcome to this beautifully refreshed townhome nestled in a quiet cove community in the heart of Winter Park. Thoughtfully updated throughout, this light-filled home features new flooring downstairs, fresh carpet on the stairs, new paint throughout, and new light fixtures — move-in ready and waiting for you. The open floor plan flows seamlessly from the living and dining combination into the kitchen, where granite countertops, a charming bay window with bench seating, and a convenient pass-through to the dining area make everyday living a pleasure. A powder room is conveniently located on the main level, and the family room opens into an enclosed sunroom — a versatile bonus space perfect for a home office, playroom, or quiet retreat. A decorative fireplace and ceiling fans add warmth and comfort throughout. Upstairs, the spacious primary suite offers a private en suite with walk-in shower and a walk-out balcony — your own personal escape. A second bedroom on the upper level enjoys its own private bath with tub/shower combo. The third-floor bedroom is a standout, complete with a full bath featuring a walk-in shower and an oversized walk-in closet. High ceilings throughout give the entire home an airy, expansive feel. Residents enjoy access to a community pool and are zoned for an exceptional A-rated school corridor — Dommerich Elementary, Maitland Middle, and Winter Park High School. The location is equally impressive, with easy access to major roads, shopping, and dining, plus walking distance to Howell Branch Preserve Park. Available now at $2,200/month. Security deposit of $2,200 required. Application fee of $50 per adult. No pets. No smoking.

Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)

Listing Agent: Dee Morgan (407-616-5526)

Remarks: Welcome to 870 Carver Street, a thoughtfully designed two-bedroom, two-bath residence in the core of Winter Park. Offering more than 1,200 square feet, the newly constructed home features vaulted ceilings with exposed rafters, warm wood finishes and industrial-inspired black metal ductwork that define its architectural character. The primary suite includes a floating wall closet system, a laundry closet, and a bath with dual-sink floating vanity + glass-enclosed walk-in shower. The second bedroom features an en-suite full bath with a tub-shower combination and a floating wall closet system. The open living area is designed for entertaining and anchored by a well-appointed kitchen with solid wood cabinetry, under-cabinet lighting, and a substantial island with seating for four. Black aluminum-framed windows bring abundant natural light into the interiors and enhance the open-plan layout. Outdoor spaces include covered entries, an expansive front porch with warm wood architectural detailing, and a fully fenced yard with a rear garden courtyard. The garage offers oversized dimensions and additional depth for storage and is accessed via a sliding steel-framed, wood-clad gate along Railroad Avenue. Ideally located within short distance to Park Avenue, Winter Park Village, Whole Foods Market, the Winter Park Golf Course and the SunRail and Amtrak stations, the residence provides convenient access to shopping, dining and transportation in one of Winter Park’s established neighborhoods. **Lease includes water, sewer, electric, trash, grounds maintenance, and exterior pest control. The garage apartment may be available separately or the entire property may be leased together if desired.**

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

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

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: 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: 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: 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: 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: One or more photo(s) has been virtually staged. Lovely home in Winter Park school district. Closet to downtown Winter Park. Updated kitchen and baths on a Quiet street. Lawncare included.

Listing is courtesy of: VIA PROPERTIES LLC (321-229-6085)

Listing Agent: Donna Peebles (321-229-6085)

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: This 2 bedroom, 2.5 bathroom townhome is located in Winter Park's desirable Sandlewood Creek community. Enjoy Park Avenue's shops and restaurants, Winter Park Village, highly rated schools, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a spacious main living area with open living room and dining room, a gorgeous kitchen with quartz countertops, stainless steel appliances, and breakfast bar, a lovely primary suite with custom bathroom finishes, laundry closet, and a rear patio. Community amenities include a pool. Sorry, no pets. 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 (407-897-3366)

Listing Agent: Matthew Kirsch (407-897-3366)

Remarks: This 2 bedroom, 2.5 bathroom townhome is located in Winter Park's desirable Sandlewood Creek community. Enjoy Park Avenue's shops and restaurants, Winter Park Village, highly rated schools, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a spacious main living area with open living room and dining room, a gorgeous kitchen with quartz countertops and breakfast bar, a lovely primary suite with custom bathroom finishes, laundry closet, and a rear patio. Community amenities include a pool. 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 (407-897-3366)

Listing Agent: Matthew Kirsch (407-897-3366)