Apartments for Rent in Winter Park 32789 - 42 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: 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)

Remarks: Welcome to this charming and well-maintained rental located in a quiet, centrally situated community in the highly desirable Maitland/Winter Park area. This spacious 2-bedroom, 2.5-bathroom home offers comfort, convenience, and a low-maintenance lifestyle. Inside, you’ll find a bright and open floor plan with a generous living and dining area that flows seamlessly into the kitchen, which is equipped with brand new appliances. The layout provides plenty of natural light, along with ample closet space and storage throughout. Step outside to enjoy a private backyard space—perfect for relaxing or entertaining. Residents of this community enjoy access to a sparkling pool, beautifully maintained grounds, and the ease of included exterior and yard maintenance. Assigned parking is available, along with additional guest parking for visitors. Ideally located just minutes from Park Avenue, this home offers quick access to popular dining, shopping, grocery stores, and entertainment options, as well as nearby parks and major roadways for easy commuting. Zoned for top-rated schools including Dommerich Elementary, Maitland Middle, and Winter Park High School. This is a great opportunity to enjoy a comfortable rental with the feel of a townhome in a prime location—don’t miss it!

Listing is courtesy of: THE AGENCY FL (407-335-4119)

Listing Agent: Brian Hyser (407-951-2472)

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 a true Mid-Century rental in Winter Park located in the quaint neighborhood of Fairbank Shores. Spacious 2 bedrooms and 1.5 bath home with 1 extra flexible room that can be used as an office or 3rd bedroom(no closet). Centrally located, minutes form I4, close to Park Avenue District, College Park, major shopping centers and many more. Big backyard with a nice sized paved courtyard and shed. Don't miss this opportunity!

Listing is courtesy of: 365 REALTY, INC. (407-944-1365)

Listing Agent: Vanessa Rivera Laboy (407-766-8093)

Remarks: Winter Park Lakefront Community. Lakefront Deck, Dock, Grill, Community Building, Heated Pool and Sauna. Immaculate 2 Bedroom 2 Bath First Floor Unit. Upgraded Kitchen with Raised Ceiling, Maple Cabinets and Granite Counters. Cabinets (matching Kitchen Cabinets) and Counters built in Dining Room for extra Storage. Recently Painted. New Carpets in Bedrooms. Bathroom Vanities and Commodes have been replaced. New Storage Cabinet in Hall. Windows have been replaced. A/C approximately 10 years old with regular servicing. Walking Distance to shopping Centers. Minutes to Downtown Park Ave. Look no further! You have found the perfect unit for rent! Unit also available for sale! (See MLS#65376215)

Listing is courtesy of: REALCOM REAL ESTATE SERVICES INC (407-621-6856)

Listing Agent: Janice Erickson (407-621-6856)

Remarks: Spacious first floor unit in Waterfall Cove 1 bedroom, charming residential unit , This inviting space offers a comfortable layout with plenty of natural light. Conveniently located near shops, restaurants and parks. It is perfect for enjoying the Winter park lifestyle.

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Yigit Orer (407-948-5347)

Remarks: One or more photo(s) has been virtually staged. A contemporary, beautifully finished home offering standout value in one of Winter Park’s most coveted zip codes. With more than 2,500 square feet of bright, open living space, this property features a sleek fireplace, a large pantry area, a designer kitchen, and a massive two-car garage. The private primary suite sits upstairs along with additional bedrooms, a versatile loft, and a conveniently placed laundry room. A first-floor guest suite adds flexibility for visitors or a dedicated workspace. Outside, a spacious backyard and custom gazebo create an inviting place to unwind. Zoned for Princeton Elementary and positioned for quick, easy access to everything College Park and Winter Park have to offer, this home delivers rare quality and exceptional value for 32789. This home is available immediatly.

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

Listing Agent: Kris Kennedy (813-947-3509)

Remarks: Beautifully maintained home in the highly desirable Winter Park 32789 neighborhood. This charming property offers an inviting floor plan with abundant natural light, spacious living and dining areas, and a well-appointed kitchen with generous counter space and modern finishes. Comfortable bedrooms provide ample storage, and the primary suite offers a private and peaceful retreat. Flexible bonus space is ideal for a home office, playroom, or guest area. Enjoy outdoor living in the private, landscaped fenced in backyard featuring mature trees and plenty of room for entertaining, gardening, or relaxing. Situated on a quiet street just minutes from Park Avenue, top-rated Winter Park schools, Rollins College, shopping, dining, and community parks. A rare opportunity to rent a home in one of Central Florida’s most sought-after neighborhoods.

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

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

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: 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: 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)