Apartments for Rent Near Winter Park High in Winter Park - 29 rentals

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: Beautiful 4 Bedroom Furnished House with a Pool! This home has an Eat-In Updated Kitchen. There are 3 bedrooms and a bathroom on one side and a large master suite on the other side with a fireplace. The master bathroom has an extra large walk-in shower with a double mirrored dressing area. There is a family room/ FLex Space/ Office Area with a Roku TV, Desk, and Wi-Fi. There is no garage. It has 2 sheds for storage in the back. The neighborhood is nice and quiet. It is conveniently located near Hospitals, Businesses, Restaurants, Schools and Shopping.

Listing is courtesy of: A +ROI PROPERTY (407-718-7994)

Listing Agent: Rene Fossey (407-718-7994)

Remarks: Nestled along a quiet brick-lined street in Winter Park’s coveted Via’s neighborhood, 1041 Tuscany Place offers a rare blend of elegance, comfort, and breathtaking natural beauty. From nearly every room, this exceptional residence captures tranquil views of the private backyard and picturesque Lake Temple beyond. Inside, a thoughtfully designed open floor plan is enhanced by soaring vaulted ceilings and an abundance of natural light, creating a warm yet sophisticated atmosphere. The gourmet kitchen is beautifully appointed with premium Wolf appliances, a Sub-Zero refrigerator, quartz countertops, imported Italian cabinetry, and a striking mother-of-pearl mosaic backsplash. The primary suite serves as a peaceful retreat, complete with serene landscape views and a spa-inspired bath featuring a spacious walk-in shower with skylights, body jets, and an oversized 40-inch rainfall showerhead. Upstairs, two generously sized bedrooms share a well-appointed Jack-and-Jill bath, offering comfort and privacy for family or guests. Outdoor living is just as impressive. A spacious deck invites you to relax and entertain while overlooking the sparkling pool and hot tub, while the lower decks bring you into nature with an inviting fire pit overlooking the water. The expansive, beautifully landscaped backyard provides a private setting to enjoy the best of Florida living. Ideally located just minutes from the Winter Park Racquet Club, Interlachen country club, Lake Maitland, and the shops and dining of Park Avenue, this home offers an extraordinary lifestyle in one of Winter Park’s most desirable settings.

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

Listing Agent: Bradford Barnett (407-227-0647)

Remarks: Lawn and pool maintenance included in rent! Welcome to this beautifully upgraded Winter Park pool home, designed for effortless living and exceptional entertaining. This 3-bedroom, 2-bath residence offers an open, inviting floor plan with a spacious kitchen featuring updated countertops and cabinetry, stainless steel appliances, beautiful bathroom finishes and updated flooring throughout. The home truly shines outdoors, offering an abundance of entertaining space. Enjoy a screened-in pool, covered patio, and multiple seating areas including a tiled lounge space with a firepit, all set within a large, fenced backyard with both lush grass and low-maintenance turf. Whether hosting guests or enjoying a quiet evening, this home provides the perfect setting. Inside, the light-filled dining room overlooks the backyard from three sides, while the primary suite features a spacious closet and private en-suite bath. All bedrooms include newer carpet, and a generous utility room off the carport offers ample space for laundry and storage. Located in a highly rated school zone and just minutes from Rollins College, parks, shopping, dining, and everything Winter Park has to offer, this home delivers both lifestyle and convenience in one exceptional rental opportunity.

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

Listing Agent: Lianna Dangelo (321-446-3509)

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: Exceptional Lease Opportunity | The Vias, Winter Park $13,500/mo | $15,000 Security Deposit | One-Year Lease | Pets Considered (Owner Approval) | Available Now Rarely does a home of this caliber come to market for lease. Set on a quiet cul-de-sac in one of Winter Park's most prestigious enclaves — the coveted Vias neighborhood — this magnificent 7,000 SF residence delivers an unmatched combination of scale, sophistication, and livability across three thoughtfully designed levels. Rich hardwood floors anchor the main living areas, setting a tone of warmth and understated elegance throughout. The open-concept floor plan transitions effortlessly between spaces, equally suited to quiet evenings at home and large-scale entertaining. At the center of it all is a chef's kitchen appointed with 42-inch cabinetry, quartz countertops, a professional gas range, and double ovens. An oversized eat-in bar and adjacent dining area connect seamlessly to the family room, ensuring the cook is always part of the conversation. The home offers two expansive primary suites, each a serene private retreat. The main floor — along with the second level — encompasses 4,500 SF and five bedrooms with four baths. The main suite is a true sanctuary, complete with a spa-caliber bath and a custom walk-in closet. A gas fireplace anchors the family room, while French doors open to the covered rear patio and pool deck. Upstairs, four additional bedrooms are served by two Jack-and-Jill baths, a generous laundry room, and a versatile studio or playroom. Custom loft stairs climb to a third-floor bonus space, ideal for creative pursuits or kids' play. The lower level is an exceptional offering in its own right — a fully appointed 2,500 SF in-law suite with a private living area, kitchenette and breakfast bar, a spacious primary bedroom with ensuite bath, two secondary bedrooms, a full hallway bath, gym, workshop, and a game room with pool table. Generous window wells flood the space with natural light, and direct access to the back patio and pool deck makes the transition between levels completely seamless. Zoned for the highly regarded Dommerich/Maitland/Winter Park High School district, and just minutes from the shops and dining of Park Avenue and a short stroll to the Winter Park Racquet Club — this is Winter Park living at its finest. All measurements and dimensions should be independently verified.

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

Listing Agent: Kelly Price (407-645-4321)

Remarks: Rare opportunity to lease a spacious 4-bedroom, 3-bath home in one of Winter Park's most coveted enclaves — The Vias. Spanning 2,207 SF, this sun-drenched residence sits just a short stroll from the prestigious Winter Park Racquet Club. Flooded with natural light, the open-concept living spaces feature beautiful bamboo wood floors, a well-appointed kitchen with white cabinetry and a large island, and a sunken family room with walls of windows overlooking the pool and backyard. The primary suite enjoys its own private bath, while three guest bedrooms share a hall bath. A full pool bath with walk-in shower off the family room adds everyday convenience. An attached 2-car garage offers additional parking or storage. Step outside to your private backyard oasis, where a sparkling pool, heated spa, and generous yard space are ideal for effortless Florida living. Situated on a nicely sized lot, this home is zoned for Dommerich Elementary, Maitland Middle, and Winter Park High School. Lawn care and pool care are included. Available May 1, 2026. 4 bedrooms, 3 bathrooms, 2,207 SF at $5,895 per month. Security deposit of $7,500 required. Renters insurance is required. Pets are considered on a case-by-case basis, subject to owner approval.

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

Listing Agent: Kelly Price (407-645-4321)

Remarks: Welcome home! This fantastic 3-bedroom, 2-bath home is available for immediate move-in! This property is a short drive from downtown Winter Park, the Crosby Center for Health and Wellbeing, Cady Way Park, and more! , this property features a comfortable layout with well-apportioned bedrooms and bathrooms, a lovely kitchen with lots of counter and cabinet space, and many desirable features. Act now! This one won't last long! All applicants are required to do a credit and background check. 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: Gorgeous single-family home in the "tree streets" of Winter Park now available for rent or purchase. Private pool, two car garage, fabulous location and newer construction! Don't wait! Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, thoughtfully constructed in 2023 by the original owner/builder, located in one of Winter Park’s most sought-after neighborhoods. Designed with sleek sophistication and functional elegance, this fabulous home offers 4 bedrooms, 3 full baths, and a flexible layout perfect for today’s lifestyle. The open-concept main floor features a beautifully appointed kitchen, a spacious dining area, and a light-filled living room complete with a designer fireplace and custom built-in shelving. The stunning kitchen boasts quartz counters, spacious cabinetry, KitchenAid appliances, and designer lighting. A fourth bedroom (currently used as a study) is also located on the main level. From the great room, expansive sliding glass doors lead out to the covered lanai, where you'll find an in-ground pool, a fully fenced yard, tongue-in-groove wood ceiling, and pre-plumbing in place for your dream summer kitchen—ideal for entertaining year-round. Upstairs, the luxurious primary suite provides a peaceful retreat with an oversized balcony overlooking the pool and rear yard. Two additional bedrooms are also featured on the second level, along with a second full bath. The first-floor office doubles as a fourth bedroom, with an adjacent full bath for guests or multi-generational living. This home boasts well-thought-out upgrades, including beautiful wood inlays in niches, open shelving, quartz countertops, slat wall features, and stunning light fixtures throughout. The work has been done for you in this like-new home! Located just steps from Phelps Park and minutes from the shops and dining of Park Avenue and the Winter Park Chain of Lakes, this home offers the perfect blend of modern design, comfort, and convenience. Don't miss your chance to rent or own this exceptional home in the heart of Winter Park!

Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)

Listing Agent: Sue Silberbusch (407-252-3157)

Remarks: Check out this Winter Park gem near Lake Sue! This 3BR/2BA home features a modern kitchen with granite and stainless steel, wood floors, and a private backyard oasis (landscaping included). Perfect for commuters or remote workers, it boasts an oversized 3rd bedroom/office and is minutes from Park Ave and Audubon Park. Zoned for Audubon K-8 and Winter Park High. Every applicant should apply separately. 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: Prepare to be impressed by this beautiful two story home on a charming brick paved street in Winter Park! This 4 bed 2.5 bathroom home awaits you with recent interior and exterior paint updates, hard wood floors, granite countertops and upgraded stainless steel appliances. A grapefruit tree and lush landscaping create a serene setting to relax on your sprawling front porch. Upon entering you are welcomed by an abundance of natural light filling the entryway, dining room and formal living room. The inviting family room includes a stylish wood burning fireplace and French doors that lead out to the backyard. Cook and enjoy your favorite meals in the home’s gourmet kitchen and dinette area. Right off the large 2-car garage is a walk-in laundry room and a lovely half bathroom. Upstairs is the spacious master bedroom and master bathroom including a large soaker tub and walk-in shower. Experience gorgeous Florida outdoor living in the impressive second floor deck that can be accessed through the master bedroom or backyard. Enjoy the lime and pineapple trees in this well-maintained backyard. The home is conveniently located in close proximity to Winter Park’s Park Avenue restaurants and shops and incredible schools. Landscaping/Lawn Care will be provided by landlord.

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

Listing Agent: Lisa Gould (407-721-7612)

Remarks: Updated Charming 4 Bed/2 Bath mid-century home located in Northwood Terrace/Audubon Park (just across the street from Baldwin Park). You will love the large lot .34 Acres with it botanical garden, meditation area, a patio with a raised HOT Tub (perfect for a starry night) and plenty of privacy with all the lush foliage. The front door opens to a great room where the kitchen, living area, dining room, and family room are all open to each other. The Hurricane resistant double panned windows offer gorgeous outdoor views, and invite natural light into each room. The kitchen features granite counters, a breakfast bar, pantry, and an additional combo utility & storage room with Washer/Dryer. The kitchen also has a reverse osmosis water filtration system to produce alkaline water for healthy living. The large family room has a wood-burning fireplace & sliding doors to the scenic backyard. The Master suite also has access to the backyard an impressive walk-in closet. The Master Bath has separate areas or the toilet/sink and bath/shower sink. All closets are cedar lined. Zoned for Winter Park Highschool and K-8 Audubon Park school! No HOA! Steps away from Baldwin Park, East End Market, and just a bike ride away from Downtown Winter Park!

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: John Goggin (321-332-3000)

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 beautiful 2 bed / 1 bath 1,029 square foot home in Winter Park is totally refurbished and available for immediate occupancy. Newer kitchen cabinets. Newer bathroom. With a single car carport. This property features wood floors throughout, tile floors in the kitchen, dining room and bathroom, large open yard. Washer/dryer, shed & lawn care included! Application Fee: $50 each adult (18+) **Full Credit/Skip/Eviction/Background check is done on all applicants. **Please have the following documents ready to attach as JPEG or PDF: - Drivers License - (3) Pay Stubs

Listing is courtesy of: PREMIER MANAGEMENT GROUP INC (407-370-4400)

Listing Agent: Ken Warren (407-370-4400)

Remarks: Enjoy elevated lakeside living in this top-floor residence overlooking tranquil Lake Osceola in downtown Winter Park. Located on the top level of the Whispering Waters condominium community, this fully remodeled home features three spacious bedrooms (one currently used as a den), three full baths and an open layout designed to showcase expansive water views. The primary suite features an oversized walk-in closet, while the living room includes a nook overlooking the lake, ideal for a home office or reading area. The generous kitchen offers a pantry and eat-in dining space, seamlessly connecting to the living and dining areas. Sliding glass doors invite natural light and lake breezes throughout. A private laundry room and secured garage parking add everyday convenience. This residence includes a deeded boat slip, providing direct access to Winter Park’s iconic chain of lakes. A community elevator offers access to the third floor. High-end modern finishes, ample storage and refined living spaces make this offering exceptional in both quality and location. Please note: At least one resident must be 55 years of age or older. All additional residents must be at least 21. Lease includes one assigned garage parking space and a deeded boat slip. Annual lease only. Application and association approval required.

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

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

Remarks: Experience the rare luxury of a high-performance, meticulously updated 3-bedroom sanctuary in a quiet Winter Park cul-de-sac, offering the perfect blend of modern utility and suburban serenity. Zoned for Winter Park High School, this versatile floor plan features both a dedicated private office for the remote professional and an expansive game room for premier entertaining. Every major system has been addressed for total peace of mind, including a BRAND NEW ROOF (2026), high-efficiency AC (2025), and a fresh 2026 interior refresh. The heart of the home is a light-filled living area anchored by a magnificent wood-burning stone fireplace, leading to a chef’s kitchen outfitted with premium Quartz countertops, new cabinetry, and a new dishwasher. Experience a seamless flow with brand-new luxury vinyl plank flooring throughout—no carpet—and spa-inspired bathrooms featuring a new walk-in primary shower and pristine guest bath updates. Situated on an oversized .33-acre lot, this property provides exceptional privacy and space rarely found in a rental. Enjoy the convenience of being just 5 minutes from Costco and major retail hubs, 15 minutes from Park Avenue’s world-class dining, and offering swift access to UCF and the 417. This is more than a rental; it is a meticulously modernized retreat ready for immediate move-in.

Listing is courtesy of: NEXTHOME NEIGHBORHOOD REALTY (407-377-7735)

Listing Agent: Brenden Rendo (407-710-8720)

Remarks: Furnished turn-key luxury lake-view home in Winter Park where comfort meets style. Pricing includes utilities/wifi. 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: Meticulously maintained home with a Highly-Flexible floor plan offering 4 bedrooms, two bonus room areas that would be perfect for a home gym, nursery or media room. In one of Winter Park's most sought after areas. Enjoy the enjoyment of local parks, restaurants, convenient shopping, easy commutes and some of the best walkability around. This traditional home sits on a very private corner lot. Features front covered patio and sitting area. Lots of natural light in the oversized great room and it’s the perfect entertaining space. It has a true chef’s kitchen including solid wood custom cabinetry, 5 burner gas stove with pot filler, Sub-Zero refrigerator, Fisher & Paykel double drawer dishwasher and so much more. The primary suite is upstairs and offers a luxurious secluded environment to relax. The oversized suite has its own private balcony that looks out over the beautiful private backyard and pool space. The master bath has a large jetted tub, walk in shower, double vanities with tons of counter space PLUS a 16x13 Custom Designed Walk-in closet...and so MUCH more! Call for your private viewing today!

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

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

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: Welcome to 870 Carver Street, a one-of-a-kind rental offering two distinct, private residences on a single fully fenced property in the heart of Winter Park. The main home is a 2 bedroom, 2 bath retreat featuring vaulted ceilings with exposed rafters, warm wood finishes, and industrial-inspired black metal ductwork. The open living area is 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 flood the space with natural light. The primary suite includes a floating wall closet system, in-suite laundry, and a spa-style bath with dual-sink floating vanity and glass-enclosed walk-in shower. The second bedroom features an en-suite full bath with a tub-shower combination. The second residence is a self-contained 1 bedroom, 1 bath unit with its own private entrance and dedicated driveway on Carver Street, completely separate from the main home. Inside, vaulted ceilings, tile flooring, a full kitchen, en-suite bath, private laundry, and white oak stairs lead to a bright, cohesive living and dining area. The two residences share a fully fenced yard with a rear garden courtyard but are otherwise independent, making this an ideal arrangement for roommates, a home office, a live-in guest, or simply extra space on your own terms. Outdoor spaces include covered entries and an expansive front porch with warm wood architectural detailing. An oversized garage with extra depth for storage is accessed via a sliding steel-framed, wood-clad gate along Railroad Avenue. Just a short distance from Park Avenue, Winter Park Village, Whole Foods Market, the Winter Park Golf Course, and the SunRail and Amtrak stations... everything Winter Park has to offer is right at your door!

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

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