Multiple Cities, Zip Codes, Addresses, Streets, Neighborhoods, MLS IDs
(separate each with the word OR)
Ex.Miami OR Coral Springs OR Boca Raton33319 OR 33321 OR 33467
Find Winter Park Real Estate for Rent by clicking on the relevant neighborhood.
View all Winter Park Real Estate for Rent
STANSBURY ESTATES - O6396986 - 2011 CORNELL AVE #3, WINTER PARK, FL 32789 2 Days on yellowkey
$800 | Apartment | 1 beds | 1.0 baths
Beautifully renovated private studio unit (1 bed / 1 bath) located in the rear of the property in a highly desirable area near Winter Park and Downtown Orlando. This cozy detached unit offers a comfortable living space with a private bathroom, ideal for a single professional or student looking for convenience and privacy. Water and electricity are included in the rent, making it an easy and budget-friendly option. The main house and the additional front unit are currently occupied, while this rear studio offers its own separate and peaceful setting. Excellent location with easy access to I-4, Downtown Winter Park, Downtown Orlando, shopping, dining, and Dubsdread Golf Course.
Listing is courtesy of: LPT REALTY, LLC
CONWILL ESTATES - O6397097 - 1701 WALNUT AVE, WINTER PARK, FL 32789 2 Days on yellowkey
$7,800 | Single Family Home | 4 beds | 4.5 baths | 2 gar
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
MAGNOLIA GARDENS SUB - O6397105 - 870 CARVER ST, WINTER PARK, FL 32789 3 Days on yellowkey
$5,150 | Single Family Home | 3 beds | 3.0 baths | 2 gar
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
EASTBROOK SUB UNIT 8 - O6397042 - 3425 BALSAM DR, WINTER PARK, FL 32792 3 Days on yellowkey
$2,600 | Single Family Home | 3 beds | 2.0 baths | 2 gar
This beautifully remodeled and completely updated property located in Winter Park, has 1,516 square feet of open living, complete with a living room, eat-in kitchen, and family room. The living area is enhanced with a custom built-in electric fireplace framed by a beautiful wood mantle, creating a warm and inviting atmosphere. A BRAND NEW ROOF was installed in Nov/2024. Updated windows throughout, BRAND NEW LVP flooring. BRAND NEW kitchen cabinets and QUARTZ COUNTERTOPS with BRAND NEW FRIGIDAIRE KITCHEN APPLIANCE PACKAGE. Updated bathrooms with tile floors and new vanities. BRAND NEW TANKLESS ELECTRIC HOT WATER HEATER. Spacious 2 car garage with NEW EPOXY FLOORING, dedicated laundry space with additional cabinetry and plenty of storage as well. Located in the highly desirable neighborhood of Eastbrook, this 3-bedroom, 2-bathroom block home is completely move-in-ready. Sitting on a large corner lot with privacy fence and a beautiful paver patio, complete with city lights, that’s perfect for entertaining friends and family and also spacious enough for pets. This property is a must-see! Hurry, call now for your private showing.
Listing is courtesy of: LEGENDS REAL ESTATE PROFESSIONALS, INC
WINTER WOODS UNIT 04 - S5147313 - 1985 JAPONICA RD, WINTER PARK, FL 32792 3 Days on yellowkey
$3,300 | Single Family Home | 4 beds | 2.0 baths | 2 gar
"Charming family home available for rent in a quiet area of Winter Park! This property has a spacious design of 4 bedrooms, a private patio perfect for barbecues and an incredible pool to share with family, as well as an incredible patio in one of the quietest streets, wooded and familiar, you will have easy access to local parks, the farmers market and the center of Winter Park. Pets are accepted with a deposit. Make this house your next home!"
Listing is courtesy of: LA ROSA REALTY LLC
LAKE WAUNATTA WOODS - O6396599 - 4033 YACHT CT, WINTER PARK, FL 32792 3 Days on yellowkey
$3,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar
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
SANDALWOOD CREEK CONDO PH 05 - O6396280 - 148 SANDLEWOOD TRL, WINTER PARK, FL 32789 4 Days on yellowkey
$2,175 | Condo | 2 beds | 2.5 baths
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
SANDALWOOD CREEK CONDO PH 07 - O6395198 - 409 SANDLEWOOD CV #3, WINTER PARK, FL 32789 4 Days on yellowkey
$2,200 | Condo | 3 beds | 3.5 baths
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
ENCLAVE AT HAWKS CREST - O6396367 - 1530 BANTAM WAY, WINTER PARK, FL 32792 6 Days on yellowkey
$2,800 | Townhouse | 3 beds | 2.5 baths | 2 gar
Beautiful townhouse in a pool community, near to supermarket and Costco, good school area. High and trey ceiling in the master bedroom with high loft and living room. Beautiful tile floor on first floor
Listing is courtesy of: U S GLORY REALTY
CONWILL ESTATES - O6396000 - 1711 CHESTNUT AVE, WINTER PARK, FL 32789 7 Days on yellowkey
$4,150 | Single Family Home | 4 beds | 3.0 baths | 2 gar
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.
KILLARNEY ESTATES - O6396001 - 438 LAKEVIEW AVE, WINTER PARK, FL 32789 7 Days on yellowkey
$3,400 | Single Family Home | 2 beds | 1.0 baths | 1 car
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
PARKVIEW VILLAGE - O6395924 - 3032 ANTIQUE OAKS CIR #145, WINTER PARK, FL 32792 8 Days on yellowkey
$1,400 | Condo | 1 beds | 1.0 baths
1 Bedroom/1 Bath condo in Winter Park's Parkview Village! Situated just off of 436/South Semoran Blvd & so convenient to UCF, Full Sail University, 417 & more! The living room, dining & kitchen layout flows easily with sliding doors that lead to the screened patio! Fresh interior paint, washer & dryer. Parkview Village offers a pool, clubhouse. Take a look today!
Listing is courtesy of: MAINFRAME REAL ESTATE
GOLFSIDE VILLAS CONDO - R4910991 - 1000 S SEMORAN BLVD #815, WINTER PARK, FL 32792 8 Days on yellowkey
$1,650 | Condo | 2 beds | 2.0 baths
This newly update and freshly painted. First floor condo in Winter Park offers a perfect blend of comfort and style and outdoor access ..It features two spacious bedrooms and two bathrooms, providing ample space for relaxation and privacy. The open plan living room and updated kitchen create a welcoming atmosphere, ideal for both entertaining and everyday living.. A standout features of this home is the in-unit washer and dryer a rare item within the complex. Community also has an additional laundry facility of it own. From the living room you can Step outside onto the nice open patio….whether it's for morning coffee or evening cookouts with family and friends. The community pool is walking distance and accessible to all residents. Unit has two parking spaces and plenty of additional guest parking. The condo is ideally located, with plenty shopping and dining nearby. Full Sail University and a newly built HCA Emergency room are minutes away. Commuting is made easy with access onto 436, and the 408 which makes it easy to travel to Downtown Orlando or Winter Park
Listing is courtesy of: KIMBRIDGE REALTY, LLC
HIDDEN OAKS CONDO PH 06 - WINTER PARK, FL 32792 8 Days on yellowkey
$1,750 | Townhouse | 2 beds | 1.5 baths
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
LAKE KNOWLES TERRACE ADD 02 - O6395705 - 1441 ONECO AVE, WINTER PARK, FL 32789 8 Days on yellowkey
$6,000 | Single Family Home | 4 beds | 3.5 baths | 2 gar
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
SOUTH LAKEMONT SHORES - O6395037 - 1814 BARKER DR, WINTER PARK, FL 32789 8 Days on yellowkey
$11,000 | Single Family Home | 5 beds | 4.0 baths | 2 gar
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
LAWNDALE - O6394834 - 1555 MICHIGAN AVE, WINTER PARK, FL 32789 9 Days on yellowkey
$1,450 | Half Duplex | 1 beds | 1.0 baths
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
GLENCOE SUB - O6394762 - 2420 EUSTON RD, WINTER PARK, FL 32789 9 Days on yellowkey
$1,775 | Single Family Home | 2 beds | 1.0 baths | 1 gar
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
WATERFALL COVE - O6395336 - 1695 LEE RD #D116, WINTER PARK, FL 32789 10 Days on yellowkey
$1,800 | Condo | 3 beds | 2.0 baths
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