Apartments for Rent in Winter Park 32789 - 38 homes

Remarks: Bring your boat and discover this charming Winter Park gem, perfectly nestled on a quiet, desirable brick-lined street. This inviting 2-bedroom, 1-bath home features beautiful hardwood floors and a warm, welcoming feel throughout. Enjoy a lakefront yard feet from the house that offers peaceful water views and the perfect setting for outdoor living. Step outside to an amazing backyard complete with a cozy firepit and large privacy bushes that create a secluded, tranquil retreat—ideal for relaxing evenings or entertaining guests. With a deeded dock and boat lift, you’ll have direct access to the Lake Killarney lifestyle you’ve been dreaming of. Come see this special home and start enjoying the lake life you deserve!

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

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

Remarks: Gorgeous Modern Home with 4 bedrooms + 3 and a half bath home with numerous upgrades throughout located in desirable Winter Park. This house has a large kitchen that opens to the family room for entertaining. Fantastic kitchen with solid wood cabinets, granite counters, walk-in pantry, stainless appliances, Gas 5 burner stove, built-in microwave, large island, big windows emanating a lot of natural light. The home features hardwood floors throughout the main living area, stairs, upstairs bonus loft, and Primary bedroom. The living room offers a gas decorative fire feature, a separate dining room and a large sliding glass door allowing additional natural light, that leads out to a covered patio and private fenced yard. The downstairs living space also has a fourth bedroom and full bath, an indoor laundry room, and a guest half bathroom. At the top of the stairs is a bonus loft for more living space, 2 bedrooms with a jack-and-jill bathroom, and closets with shelving. Upstairs also has the large primary bedroom with double door entrance, wood floors, plantation shutters on windows as well as the large sliding glass doors that lead out to the private balcony, the walk-in closet has custom built-in shelving, the big bathroom has two separate sinks, large walk-in shower and a separate soaking tub and a toilet closet. Wonderful home for the family and one of the best school districts. The surrounding area offers grocery stores, shopping, parks, easy access to highways, and moments away from Park Ave shopping and entertainment, farmers market, boat tours and so much more.

Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)

Listing Agent: Wendy Calvet (407-276-5024)

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: Are you looking for a spacious 1 bedroom 1 bathroom unit to call home? This home features its own washer and dryer, a large bedroom and living room, a spacious kitchen with ample countertop space, plenty of cabinets. The back sunroom would make a great office or a bright sitting area. The home is located 1 mile from Park Avenue. In addition, the home is located within walking distance of restaurants and shopping.

Listing is courtesy of: BHHS FLORIDA REALTY (407-406-5300)

Listing Agent: Troy Hensley (407-406-5300)

Remarks: One or more photo(s) has been virtually staged. Beautifully mainted and move-in ready home available for rent in a convenient location. This property features a bright and inviting interior with functional layout, spacious living areas, and well-sized bed rooms. The home offers a clean feel with plenty of natural light throughout, creating a comfortable and welcoming environment. Enjoy a private outdoor space perfect for relaxing or entertaining. Conveniently located near major roadways, shopping, dining, and everyday amenities. Available for immediate occupancy! Schedule your showing today.

Listing is courtesy of: PRIMAC GROUP, INC (407-889-7075)

Listing Agent: Paula Wells (407-463-8792)

Remarks: Unbeatable Location! Don't miss this very rare and exquisite 3 bedroom, 2.5 bath, two-story Executive-Style condo in Winter Park-ideally located just around the corner from N. Orange Avenue, Park Avenue and Rollins College. Nestled in a prime, tucked-away setting, this home has been extensively remodeled with all new plumbing, electrical, duct work, flooring, appliances, and a natural gas line. In addition, two newer HVAC systems were installed in November 2022, offering modern efficiency and reliability. The gated front courtyard, thoughtfully designed by a landscape architect, provides a serene and welcoming entrance, complete with lush foliage, a potted herb garden, wooden bench, and tranquil fountain—creating the perfect first impression for guests. Inside, you’ll find a spacious dining room filled with natural light from a wall of French doors that open directly to the courtyard. A built-in dry bar with two wine refrigerators makes this an ideal space for entertaining, while oak wood flooring throughout the home adds warmth and timeless character. The chef’s kitchen is both stylish and functional, featuring sleek concrete countertops, custom cabinetry, and a premium dual-fuel 6-burner Wolf range. A cozy dinette area includes a built-in terrazzo-topped table and banquette, while a breakfast bar offers additional seating. Just beyond, the living room showcases a clean-burning bioethanol fireplace and dramatic soaring windows with views of the interior screened two-story courtyard. Upstairs, the private primary suite offers multiple closets, a private balcony overlooking the interior courtyard, and a luxurious en-suite bathroom complete with a large walk-in shower with body sprays, towel warmer, and a dedicated laundry room with built-in storage. At the opposite end of the second floor, the front-facing bedroom can also serve as an ideal home office, featuring a custom built-in desk and shelving, along with a screened balcony overlooking the front courtyard—perfect for enjoying your morning coffee or tea. The second floor also includes a third bedroom, a second full bathroom, a linen closet, and a charming sitting area or nook. A private alleyway behind the building provides convenient access to the oversized two-car garage, which features a custom built-in workbench and sink, as well as two dedicated storage closets. This exceptional location allows you to walk to the pleathora of shops and eateries on N. Orange Avneie, Rollins College, Park Avenue, the Winter Park Tennis Center, Azalea Lane Playground, and the brand new Seven Oaks Park, as well as the shops and restaurants along Orange Avenue. Offering the perfect blend of sophistication, comfort, and practicality, this beautifully updated condo is ideal for those seeking a refined, low-maintenance lifestyle in the heart of Winter Park. Full Lawn care by the HOA are included in the rental rate. A small pet may be considered on a case-by case basis. Proof of a renters insurance policy is required to rent this property. Showings by Appointment Only. Must see to fully appreciate.

Listing is courtesy of: FUSILIER MANAGEMENT GROUP (407-476-0476)

Listing Agent: Keith Race (407-536-7223)

Remarks: Welcome Home to Waterfall Cove in Winter Park! This spacious 3-bedroom, 2-bath ground floor corner unit is move-in ready with fresh paint and brand new carpet throughout. Corner placement means extra natural light and a layout that lives even larger than its generous footprint. Community Perks include a sparkling pool just in time for summer, secured building access, and a peaceful, park-like setting complete with mature landscaping. Tucked into the heart of Winter Park, one of Central Florida's most charming and sought-after communities. You're steps from Winter Park Village, a premier open-air lifestyle center with upscale shopping, Publix, Regal Cinemas, and top-tier dining. Basic internet and cable TV. Tenant responsible for water and electricity only. Easy showing — call us today and move in tomorrow!

Listing is courtesy of: ZEAL REALTY (407-789-2051)

Listing Agent: Ryan Hoppe (321-247-1098)

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: Welcome to this beautifully updated 3-bedroom, 2-bath home located in the heart of Winter Park. Filled with abundant natural light throughout and thoughtful upgrades, this home offers a warm and inviting atmosphere that would be perfect for your family. Highlights: -Primary suite featuring a walk-in closet and private ensuite bathroom -Classic terrazzo flooring -Recently remodeled kitchen with brand-new appliances -Solid wood cabinetry -Fully fenced backyard -2-car parking space -Washer and dryer included -Lawn Service Included Enjoy living in a prime Winter Park location close to shopping, dining, parks, and top-rated schools. This home blends modern updates with timeless charm, definitely a must-see! 12-month Minimum Lease $85 Non-Refundable Application Fee (18+) All Belmont Management Group residents are enrolled in the Resident Benefits Package (RBP) for $50.00/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. Please note, that we require all applicants to have - a combined monthly, net household income of 3X the monthly rent, - good standing credit - minimum score of 650, No accounts in collections - and no prior evictions or collections from any apartment complexes Along with your application, please include a copy of your photo ID as well as two consecutive months of your most recent pay stubs or other proof of income. We will not accept W2s as proof of income. The application includes full background, credit check as well as eviction judgments Pets are allowed on a case-by-case basis via the owner's instructions.

Listing is courtesy of: BELMONT REALTY (407-745-0696)

Listing Agent: Summer Hornburg (407-495-8134)

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: Occupying the entire second floor of a landmark 1925 brick building in the heart of Winter Park, this fully reimagined residence offers a rare opportunity to lease a true designer 3 bedroom, 3 bathroom loft just two blocks from Park Avenue. The open concept interior features high ceilings, abundant natural light from skylights and brand new windows, and a refined industrial aesthetic anchored by hardwood flooring and sleek quartz countertops. A custom architectural lighting package with sculptural glass pendants and vertical LED sconces adds a distinctive, high end finish throughout. The thoughtfully designed layout provides three separate bedrooms, each with its own private ensuite bath, offering both flexibility and privacy for residents or guests. Located minutes from Rollins College, Lake Virginia, boutique shopping, dining, and SunRail access, this turnkey residence combines historic character with modern design in one of Winter Park’s most desirable corridors.

Listing is courtesy of: REALTY ONE GROUP MVP (800-896-8790)

Listing Agent: Nic Cadwallader (321-279-1249)

Remarks: Enjoy easy, lakefront living in this beautifully maintained 2-bedroom, 2-bath condo in the desirable Killarney Bay community in Winter Park! This spacious unit features an open-concept layout with abundant natural light, a well-appointed kitchen, and comfortable living and dining areas—perfect for both relaxing and entertaining. Both bedrooms offer generous space, with a private primary suite that includes an en-suite bathroom and ample closet storage. Step outside to enjoy serene surroundings or take advantage of community amenities, all just moments from shopping, dining, and entertainment. Ideally located near Downtown Winter Park, Park Avenue, and with convenient access to Interstate 4, this condo offers the perfect blend of comfort, convenience, and lifestyle. Don’t miss your opportunity to call this charming property home!

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: David Drawdy, Jr. (407-629-4420)

Remarks: SPECIAL!! $500 OFF THE 1ST MO RENT IF YOU MOVE IN BEFORE 3/31!! PRIME LOCATION! JUST STEPS FROM PARK AVENUE, WALKING DISTANCE TO EVERYTHING! This beautiful TOWNHOME is located in the exclusive 400 West community, just moments from Park Avenue. It offers a PERFECT COMBINATION OF SUPERIOR CRAFTSMANSHIP, ELEGANT INTERIORS, and GREAT WALKABILITY. You can enter via the PRIVATE GARAGE or the charming garden-style front path. The main level is BRIGHT and OPEN, with HIGH-END FINISHES like large porcelain tiles and designer lighting. The CHEF'S KITCHEN features POLISHED CHROME HARDWARE, QUARTZ COUNTERTOPS, and STAINLESS-STEEL APPLIANCES, including a Whirlpool French door refrigerator. Ample STORAGE, MOTORIZED Lutron window shades, and a STYLISH POWDER BATH with under-stair storage add FUNCTIONALITY. UPSTAIRS, TWO SPACIOUS PRIMARY SUITES with HARDWOOD FLOORS and LARGE WINDOWS fill the rooms with NATURAL LIGHT. Spa-like en-suite bathrooms have LARGE PORCELAIN TILES, FRAMELESS GLASS SHOWERS, and MODERN VANITIES with CHROME FIXTURES. The primary bath includes a DOUBLE-SINK VANITY, private water closet, and built-in shower bench. A large WALK-IN CLOSET and a full LAUNDRY ROOM with Samsung washer and dryer complete this level. The THIRD FLOOR offers FLEXIBILITY with two additional bedrooms or versatile spaces, each with walk-in closets and a JACK-AND-JILL BATHROOM—perfect for GUESTS, HOME OFFICES, GYMS, or STUDIOS. Recent updates include INTERIOR REPAINT (2025), BLACKOUT SHADES, CLEANED CARPETS AND TILE, and SMART HOME features like NEST THERMOSTAT and RING DOORBELL. Guest PARKING is convenient on-site and nearby. BLENDING TIMELESS QUALITY with MODERN AMENITIES, this LOW-MAINTENANCE, THREE-LEVEL HOME offers PRIVACY and FLEXIBILITY in a QUIET, LOW-DENSITY COMMUNITY. Located just STEPS from everything Winter Park has to offer, it’s an EXCEPTIONAL OPPORTUNITY for a permanent residence or a LOCK-AND-LEAVE retreat in the HEART OF THE CITY. This property is eligible for alternative coverage in lieu of a security deposit. Eligibility requirements apply. For details and enrollment, please contact our leasing team and enjoy a deposit-free renting experience! All Specialized Property Management residents are automatically enrolled in our Resident Benefits Package (RBP) for $49/month. This package includes tenant legal liability insurance, HVAC air filter delivery (where applicable), credit reporting, a renter rewards program, and more! Specialized Property Management residents are enrolled in the Resident Benefits Package (RBP) for $49.00/month which includes tenant legal liability insurance, HVAC air filter delivery (for applicable properties), credit reporting, renter rewards program, and much more! Additionally, most homes feature high-speed internetup to 1 Gigat a special group rate. This includes premium support and professional setup powered by Second Nature, ensuring youre connected quickly at move-in. The group-rate internet is $64/month and is a required part of the program. Full details will be provided during the application process

Listing is courtesy of: SPECIALIZED PROPERTY MANAGEMENT (407-682-3355)

Listing Agent: Nancy Guadagnino (407-705-8559)

Remarks: This is a wonderful pool home located in the sought after neighborhood of Kenilworth Shores in Winter Park. It features 3 bedrooms & 2 baths with an open floor plan. Family room/dining room combo, a wonderful Florida room overlooking the backyard & pool area. Enjoy the weekends lounging around the black bottom pool and the lush landscape surrounding the backyard. ALL UTILITIES included! The backyard also has a gazebo, is totally fenced in and has lots of room to roam. Conveniently located between Baldwin Park and Winter Parks Park Avenue. Winter Park School district. Sorry, no pets.

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

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

Remarks: Cute and comfortable 1/2 of a duplex in the heart of Winter Park. This 2 bedroom 1 bath unit features ceramic tile throughout, ceiling fans in the bedroom, private washer and dryer and a full sized kitchen. The unit shares a back yard and there is limited storage on site as well. The unit is located minutes from I 4, shopping, restaurants and Rollins College.

Listing is courtesy of: BHHS FLORIDA REALTY (407-406-5300)

Listing Agent: Troy Hensley (407-406-5300)

Remarks: Welcome to this charming condominium in Winter Park! This home features a spacious living area with ample natural light, a modern kitchen with sleek appliances, and large bedrooms. Enjoy the convenience of nearby shopping, dining, and entertainment. The community provides well-maintained amenities for residents to enjoy. With its prime location, this condo provides easy access to all that the vibrant Winter Park area has to accord. Don't miss the opportunity to make this your new home!

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: Welcome home to this beautiful 2-bedroom, 1-bath gem in the heart of Winter Park! Nestled on the ground floor of the Lake Killarney Condominiums, Unit 101 offers a seamless blend of comfort, style, and lakeside living. Bright & open layout that flows from the living space into a modern kitchen with a large center island — perfect for entertaining or casual family meals. Granite countertops, stainless steel appliances, self-closing cabinets, and stylish finishes that reflect quality and fresh design. Newer insulated windows including large sliding doors bring energy efficiency to this to this immaculate home. Gorgeous views and spectacular sunsets over Lake Killarney you can enjoy from the lakefront pool, picnic & shuffleboard areas. Access to lake amenities including a private community boat ramp, dock, and fishing. Prime location: just minutes from Winter Park Village. Literally right next door to Trader Joe’s! Very convenient to Whole Foods, great dining, boutique shopping, and more. Commuting is a breeze with easy access to major roads This condo delivers more than just a home — it offers a lifestyle. If you value charm, ease, and access to nature plus city conveniences, this is the perfect pick. Whether you’re starting out, downsizing, or just wanting a beautiful place to come home to. some photos virtually staged*

Listing is courtesy of: THE FLORIDA PROPERTY SHOP SALE (352-346-7857)

Listing Agent: Elizabeth Fowler (863-441-5304)

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)