Winter Park Single Family Homes For Rent - 46 homes

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: One or more photo(s) has been virtually staged. Welcome to this beautifully refreshed 3-bedroom, 2-bath home nestled in a highly desirable Winter Park location — offering comfort, style, and convenience with no HOA restrictions. With 1,676 square feet of thoughtfully designed living space, this home is the perfect blend of modern updates and timeless character. Step inside to discover brand-new wood-look tile flooring throughout, providing both durability and a clean, contemporary feel. Fresh interior paint enhances the bright and airy atmosphere, while vaulted ceilings with exposed wood beams add warmth and architectural charm to the main living area — creating a space that feels both open and inviting. The kitchen is equipped with stainless steel appliances and offers a functional layout ideal for everyday living and entertaining. Both bathrooms have been updated, including a new sink in the primary bath, adding a fresh and polished touch. Enjoy Florida living at its best on the screened-in back porch, perfect for morning coffee or evening relaxation. The spacious backyard offers endless possibilities — whether you envision a garden, play area, or outdoor entertaining space. Additional features include a 2-car garage for convenience and extra storage, as well as a prime location just minutes from shopping, dining, and major roadways — making daily commutes and errands a breeze. This well-maintained home offers a wonderful opportunity to live in an established neighborhood with character, space, and flexibility. A perfect place to call your dream home!

Listing is courtesy of: AMERICAN DREAM HOMES INC (407-382-8100)

Listing Agent: Jenny Forest Lin (407-780-6065)

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 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: 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: 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: Leasing nicely furnished 2 bedrooms, 1 bath, living room, dining room and kitchen in 3 bedroom / 2 bath home. Each bedroom has queen size bed and closet. The kitchen is fully equipped including dishes. The living room has a sofa and tv.The dining room has a table with 4 chairs. The porch has some chairs and a small table. Outside in the back yard is a talbe with 4 chairs - picnic in your own park like back yard. Ready to move in immediately.

Listing is courtesy of: BLACKFIN REALTY LLC (407-947-9722)

Listing Agent: Scott Banta (407-947-9722)

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: 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: Winter Park Pines home,4 bed/2 bath ready for a new resident. On a quiet cul-de-sac, this renovated home offers a blend of modern amenities with a fantastic location. It features a brand new kitchen & bathrooms with quartz countertops, updated brushed brass fixtures, with lots of custom touches. It features engineered wood flooring in the living areas and primary bedroom, a convenient indoor laundry room, new windows and sliding doors that let in tons of natural light. Other upgrades include new doors, trim, fresh interior and exterior paint, and a beautiful paver patio. Outside, enjoy all-new landscaping with fresh sod and a new irrigation system, lawncare is included in the rent. This home also has a new roof, garage door, and a HVAC system. This home is also next to the scenic Cady Way trail, ideal for biking, walking, and running. Zoned for highly rated Winter Park schools: Brookshire Elementary, Glenridge Middle, and Winter Park High School. Call for your showing today! Sorry NO PETS.

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

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

Remarks: 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: Live in this updated home in Winter Park with 3 bedroom, 2 bathrooms. Large formal living area and a separate family room with dining. Kitchen with Stainless Steel appliances, Granite counter tops throughout, Ceramic Tile and Carpet flooring. Freshly painted interior and exterior. Large, fenced backyard. Laundry-room with Washer/Dryer hookups. *Bonus Amenity Included* - All residents are enrolled in the Resident Benefits Package (RBP) for $49.95/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. Pet friendly home (w. approval and non-refundable pet fee).

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Mo Jabr (407-571-1441)

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: 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: Adorable mid century modern bungalow in Winter Park! This 3 bedroom, 1 bathroom home has been beautifully updated with new tile wood floors in the main living area. The kitchen features white appliances and tasteful white cabinetry. The updated bathroom features a new vanity and classic mosaic tile floor. Enjoy the spacious backyard with wooden deck! Washer, dryer and lawn care is included! This property is available May 2026.

Listing is courtesy of: GATE PROPERTIES & MANAGEMENT INC (407-704-7904)

Listing Agent: Nicholas Wild (407-704-7904)