Apartments for Rent in Winter Park 32789 - 29 homes

Remarks: Spacious 4 bedroom, 2 bath home in a quiet neighborhood just minutes from I-4 and Fairbanks. Convenient to downtown Orlando, Winter Park Village, shopping, dining, and schools. Open split floor plan, with three comfortable bedrooms on one side and a large master suite on the other. Inside laundry room, ample parking spaces, fenced in side yard, all updated with modern finishes and move in ready.

Listing is courtesy of: A+ REALTY PROFESSIONALS, INC (407-702-5243)

Listing Agent: Susan Pinnock (407-435-9125)

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: Vacant! Great location! Must See! New paintinf interior, and new carpet. The best area at Winter Park, close to major shoppiing center, Basic tenant requirements: 650+ credit score, no BAD history, no BAD rental history, income 3 times monthly rent as a household. FIRST, LAST and SECURITY DEPOSIT MAY required.

Listing is courtesy of: CINO INTERNATIONAL INC (407-354-3318)

Listing Agent: Daniel Zheng (407-683-1881)

Remarks: Live in the heart of Winter Park, just steps from the city’s most loved restaurants, cafés, yoga studios, and boutique shops. This beautifully renovated unit offers the perfect blend of walkability, comfort, and style. Zoned for top-rated Winter Park schools and within walking distance to a renowned private school, the location alone makes this an exceptional find. Inside, the home features a double-master layout, ideal for roommates, families, or anyone wanting extra space and privacy. Enjoy the convenience of in-unit laundry and the peace of mind that comes with a fully renovated, move-in-ready interior. With no carpet anywhere, the home is easy to maintain—especially if you have pets. Modern finishes, clean lines, and thoughtful updates make this a standout property in one of Central Florida’s most desirable neighborhoods. Schedule your appointment today—this Winter Park gem won’t last.

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

Listing Agent: Farzana Zalil (407-617-3258)

Remarks: Beautiful and very spacious 3BR/2.5BA with 2 car garage, large upstairs balcony, fenced patio, New wood flooring throughout the unit, all appliances including side by side refrigerator and full size washer and dryer. This property is centrally located in winter park FL,walking distance to shopping, restaurants, bars, coffee shops, Publix Supermarket, short driving distance to downtown Orlando and Advant Health Orlando hospital and close proximity to Park Ave Won't last long , please call to schedule your appointment today.

Listing is courtesy of: HPL REALTY INVESTMENTS (407-601-6057)

Listing Agent: Moshe Sheffi (321-945-2367)

Remarks: Beautifully renovated 3 bedroom, 2 bath pool home in one of Winter Park's most desirable neighborhoods. Designed with an open floor plan, this home features wood flooring throughout the main living areas, crown molding, and an incredible chef's kitchen with Quartz countertops, a large breakfast bar, custom cabinetry, floating wood shelves, gas range, stainless steel appliances, and abundant storage. The spacious Florida room overlooks a private backyard complete with a sparkling pool, expansive deck, covered seating area, mature landscaping, and a fully fenced yard. Mango and lime trees, landscape lighting, and a powered storage shed with workbench make the outdoor space just as enjoyable as the inside. Additional features include hurricane impact windows, plantation shutters, updated lighting and ceiling fans, a Nest thermostat, surround sound, and a circular paver driveway. Ideally located just minutes from Park Avenue, Rollins College, the Winter Park Racquet Club, Winter Park Golf Club, Phelps Park, and the YMCA, with easy access to top rated schools, dining, shopping, and everything charming about Winter Park.

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

Listing Agent: Jennifer King (407-595-3272)

Remarks: Discover easy living at 2500 Lee Road, Unit 244, Winter Park, FL 32789. This charming spacious 1 bedroom, 1 full bathroom condo is located in the heart of Winter Park, offering comfort, convenience, and access to everything you need. Bright kitchen with plenty of storage and an Open living area with natural light Community features may include: Swimming pool, Assigned parking, Landscaped grounds. Perfectly situated near Park Avenue, Rollins College, I-4, and Downtown Orlando, this home offers the best of Winter Park living.

Listing is courtesy of: RE/MAX VANTAGE (407-745-4980)

Listing Agent: Rustina Gibson (407-808-7127)

Remarks: Virtually Staged. Brand-New Luxury Home for Lease in Winter Park's Most Walkable Neighborhood Live in one of Central Florida's most desirable communities without compromising on space, style, or location. This brand-new, never-lived-in home by Nautilus Homes offers 4 bedrooms, 4 full bathrooms, a private office, and over 3,000 square feet of refined living, all in the heart of Winter Park, steps from everything that makes this city special. The moment you walk in, the difference is obvious. Crème Brûlée wide-plank wood flooring flows throughout, setting a warm, elevated tone that carries into every room. The open-concept living area is anchored by a built-in wine and coffee bar, perfect for morning routines and evening wind-downs alike. The chef's kitchen is the heart of the home, featuring custom ceiling-height cabinetry, a handcrafted wood range hood, and high-end finishes designed for serious cooking and effortless entertaining. Just off the kitchen, a beautifully appointed butler's pantry finished in statement Kit-Kat tile connects seamlessly to the formal dining room, a layout that makes hosting feel natural, not stressful. The floor plan gives everyone their own space. A private office and a full en-suite bedroom on the main level offer flexibility for working from home, hosting guests, or accommodating multigenerational living. Upstairs, three additional bedroom suites each feature walk-in closets and their own beautifully finished bathrooms, no sharing, no compromising. The primary suite is in a category of its own. A spa-inspired bathroom with a freestanding soaking tub, an oversized 9-foot walk-in shower with dual sprayers, a frameless glass enclosure, and sleek linear drainage make every morning feel intentional. The walk-in closet is generously sized and thoughtfully designed. Additional features include a 2-car attached garage, central air and heating, an irrigation system, wood flooring throughout, and electric dryer hookup, everything you'd expect in a home at this level, with nothing left out. Outside, you're minutes from Park Avenue, Winter Park Village, East End Market, and a tight-knit community known for tree-lined streets, top-rated schools, and a pace of life that feels a world away from the rest of Orlando. This is the rare rental that actually lives up to the photos. Reach out today, homes like this don't stay available long.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Christina Fata (407-917-8946)

Remarks: FULLY FURNISHED and move in ready elegant home.A rare find in Winter Park. 5br/4b +bonus loft GEM! Welcome to 2075 Jewel Avenue, an exceptional residence nestled in the heart of Winter Park, 32789—one of Central Florida’s most sought-after communities. Ideally situated just minutes from the vibrant shops and dining along Park Avenue and the scenic beauty of Rollins College, this home offers the perfect blend of charm, convenience, and lifestyle. Set on a picturesque street, the property boasts inviting curb appeal with mature landscaping and a welcoming entrance. Inside, thoughtfully designed living spaces feature abundant natural light, an open and functional layout, and seamless flow ideal for both everyday living and entertaining. The private backyard provides a serene retreat with ample space for relaxing or hosting gatherings. Step outside to your fully fenced backyard, complete with a private hot tub and spacious patio, ideal for relaxing evenings or casual get togethers. With no pool to maintain, you'll enjoy low maintenance outdoor living in a peaceful setting.1 time cleaning per month and wifi included. Schedule your showing today! Located near top-rated schools, parks, and cultural attractions, 2075 Jewel Avenue presents a rare opportunity to enjoy refined living in one of Florida’s most prestigious neighborhoods. Mid term lease available.

Listing is courtesy of: URBANISTA BROKERS (407-619-7272)

Listing Agent: Paul Jimenez (407-276-3516)

Remarks: Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix, Trader Joe's, Regal Movie Theater, and a variety of restaurants and bars. Join this vibrant community and make this beautiful condo your new investment property or dream home!

Listing is courtesy of: FLORIDA DREAMS REALTY GRP INC (407-654-9992)

Listing Agent: Adriana Montes (407-654-9992)

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: 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: Experience maintenance-free living in this spacious 2-bedroom, 2-bath condominium offering 1,529 square feet in the gated Park West community in the heart of Winter Park. Located on the top floor, this spacious residence features vaulted ceilings, hardwood flooring, quartz countertops, stainless steel appliances, walk-in closets, a soaking tub, a stacking washer and dryer, and charming Juliet balconies. Residents enjoy exceptional amenities, including a community pool, tennis courts, clubhouse, and an assigned garage parking space. Water service is included in the rent. Park West is across the street from the weekly Winter Park Farmers' Market, and one block from Park Avenue; you'll have easy access to boutique shopping, highly renowned restaurants, the SunRail station, and everything that downtown Winter Park offers. Cats will be considered on a case by case basis with a non-refundable pet fee and monthly pet rent. Prospective tenants are subject to the Park West Condominium Association approval process and associated application fee.

Listing is courtesy of: FLORIDA ONE REAL ESTATE LLC (407-599-7070)

Listing Agent: Anthony Consalvo (407-599-7070)

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 landscapingan 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 homeit'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: Look no further, this luxury Modern Townhome offers premium location just minutes from Park Avenue, restaurants, shopping, Hannibal Square, and Rollins College just to name a few! Through the front door you are met with 13-foot ceilings, Modern finishes, Pella double windows, and wood flooring throughout. The Chef’s gourmet kitchen is complete with high-end flat panel cabinetry, Quartz countertops, Wolf gas cooktop, and Subzero appliances! On the second floor there are three bedrooms, 2 full bathrooms, utility room and the spacious primary bedroom is equipped with an oversized walk-in closet, opulent tub, walk-in shower, and Quartz countertops. Schedule your private showing today!

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

Listing Agent: Nicole Howell (321-217-7918)

Remarks: Nestled on a picturesque, tree-lined brick street, this charming 3-bedroom, 2-bath home offers an unbeatable location just minutes from Park Avenue, Rollins College, shopping, dining, and entertainment. Inside, you'll find a spacious floor plan featuring a formal living room, dining room, and family room, providing plenty of space for both relaxing and entertaining. The kitchen is equipped with all appliances and includes a breakfast bar along with a cozy eat-in dining area. Tile flooring runs throughout most of the home, with carpeting in one bedroom for added comfort. Additional features include an inside utility room with washer and dryer hookups, a large screened-in back porch perfect for enjoying Florida's beautiful weather, and a backyard storage shed for extra convenience. A two-car carport provides covered parking, and lawn care is included, making maintenance easy and worry-free.. All of our residents are enrolled in the Resident Benefits Package (RBP) for $39.95/month, which includes renters insurance, *RentSpree applications will not be accepted. Residents are enrolled in the Resident Benefits Package (RBP) for $39.95/month. More details upon application. This home combines charm, space, and convenience in one of the area's most desirable locations. Schedule your showing today!

Listing is courtesy of: WATSON REALTY CORP (407-359-2300)

Listing Agent: Tara Mason (407-501-1215)

Remarks: 2 bedroom, 2 bathroom condo located in the desirable and well maintained Waterfall Cove community in Winter Park. New tile floor was installed and freshly painted. Washer & Dryer in the unit. No min credit score is required. Enjoy a highly walkable location close to Whole Foods, LA Fitness, Winter Park Village, shopping, dining, and more. Community amenities include a pool, dog park, and mature landscaping. Convenient access to I-4 and major employment centers. Please use showing instructions.

Listing is courtesy of: MTRE GROUPE LLC (786-282-9992)

Listing Agent: Mauricio Toro (786-282-9992)

Remarks: FOR RENT - 648 W. SWOOPE AVENUE, WINTER PARK | OFFERED AT $2,700/MO - Stunning Home, Completely Remodeled, and Professionally Designed! Super cute 3 bedroom, 1 bath home in downtown Winter Park. Updated flooring, paint, windows, newer HVAC unit, updated kitchen cabinets, stainless steel appliances, Quartz countertops, beautiful bathroom tile work & fixtures, and interior washer/dryer. Open floorplan. Living/Dining room combo. Designer light fixtures. Fenced backyard. Located within walking distance to Park Avenue, Hannibal Square, the Winter Park Village, Rollins College and more. No smoking. Pets will be considered with an additional, non-refundable pet deposit. Move-in ready and available for occupancy July 1, 2025. Background and Credit Check required. $50 application fee. First month's rent + $3,000 security deposit. Tenant must carry renter's insurance. Lawn care and pest control included. Owner will consider pets.

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

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

Remarks: Location!! Walking distance to Rollins campus and to downtown Winter Park. Beautiful 3-bedroom 2-bathroom home. Recently renovated kitchen and freshly painted. Nearby schools include Audubon Park elementary, Glenridge Middle School, and Winter Park education center school. This house is in the perfect location, close to great restaurants and within walking distance to Winter Park farmer's market.

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

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

Remarks: Experience lakefront living at its finest in this exceptional Winter Park condo overlooking beautiful Lake Killarney. Enjoy breathtaking sunset views from your private waterfront retreat, complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers unparalleled walkability. Stroll to Park Avenue's renowned boutiques, restaurants, and nightlife, catch a movie at Regal Cinemas, or conveniently shop at Publix and Trader Joe's. With countless restaurants, bars, and everyday amenities just steps away, you'll enjoy the perfect blend of tranquil waterfront living and vibrant urban convenience. Whether you're boating on the lake, lounging by the pool, or taking in the spectacular evening sunsets, this is a rare opportunity to enjoy one of Winter Park's most desirable waterfront lifestyles.

Listing is courtesy of: COLONIALTOWN REALTY (407-896-7300)

Listing Agent: Alexander Scures (407-925-5338)