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WINTER PARK PINES - WINTER PARK, FL 32792 Just Added on 07/31/2026 4:18PM
$3,950 | Single Family Home | 4 beds | 2.0 baths | 2 gar
Located in the heart of Winter Park, Winter Park Pines is a well-established neighborhood known for its convenience, school zoning, and access to outdoor living. A place to slow down, where evening walks feel like something out of a storybook, and the Cady Way Trail is just steps from your back door for morning runs, bike rides, and everything in between. One of the standout features is having the Cady Way pool, pickleball courts, and beach volleyball courts all just a short walk away. The home is zoned for Brookshire Elementary School, Glenridge Middle School, and Winter Park High School, making this location a consistent choice for buyers prioritizing long-term value. In addition to the location, the home benefits from key updates already completed, including a 2022 roof, 2021 HVAC system, updated windows installed in 2017, along with an updated kitchen and bathrooms, offering peace of mind and modern functionality for the next owner. Ideally positioned to enjoy the Winter Park lifestyle. Close proximity to Park Avenue’s boutique shopping and exceptional dining, while the University of Central Florida, Rollins College, and Full Sail University are all within easy reach. AdventHealth Winter Park and Orlando International Airport are also close by, making both daily routines and travel simple. This is a home that delivers on every level, location, lifestyle, and lasting quality.
Listing is courtesy of: EXP REALTY LLC
SOUTH LAKEMONT SHORES - O6429070 - 1815 BARKER DR, WINTER PARK, FL 32789 Just Added on 07/31/2026 9:01AM
$4,000 | Single Family Home | 4 beds | 2.0 baths | 1 car
Furnished turn-key luxury lake-view home in Winter Park where comfort meets style. 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
SUBURBAN HOMES - O6429559 - 5101 ORANGE AVE N #B, WINTER PARK, FL 32792 Just Added on 07/30/2026 8:14PM
$2,000 | Half Duplex | 3 beds | 1.0 baths
Updated 3 bedroom, 1 bathroom half duplex with completely private, fenced in yard!! This property is in the heart of Winter Park, close to everything.
Listing is courtesy of: CITARELLI REALTY GROUP LLC
LAUREL SPGS - O6429608 - 7514 LAUREL SPRINGS DR, WINTER PARK, FL 32792 1 Day on yellowkey
$2,600 | Single Family Home | 4 beds | 2.0 baths
Welcome to this beautifully maintained 4-bedroom, 2-bathroom home offering 1,677 square feet of comfortable living space in a desirable Winter Park neighborhood. Featuring a split-bedroom floor plan, multiple living areas, and a spacious Florida room. The updated kitchen offers stainless steel appliances, wood cabinetry, and a cozy dining area. The private primary suite includes a walk-in closet and a beautifully renovated ensuite bathroom, while three additional bedrooms provide plenty of space for family, guests, or a home office. Enjoy the bright Florida room overlooking the fully fenced backyard, complete with a fire pit, grilling area, and swing—perfect for relaxing or entertaining outdoors. Conveniently located near top-rated Winter Park schools, SR-417, Full Sail University, UCF, Orlando International Airport, Costco, Target, shopping, dining, and more, this home offers the ideal combination of comfort and convenience. Don't miss this opportunity to lease a move-in-ready home in one of Winter Park's most sought-after locations! Contact the leasing agent for more information to schedule a viewing, or for help with any questions regarding the leasing process.
Listing is courtesy of: REAL BROKER, LLC
COUNTRY LANE - O6422739 - 1657 TREMONT LN, WINTER PARK, FL 32792 1 Day on yellowkey
$2,100 | Single Family Home | 2 beds | 2.0 baths | 2 gar
Be careful of scams. Only talk to a license agent. This is 2 bedroom not a 4 bedroom. Welcome to your new 2 bedrm+ office/ 2 bath/ 2 car garage home in charming Winter Park, FL. This inviting property offers an ideal location surrounded by lakes and green space, restaurants and grocery stores, making everyday conveniences just a short drive away. Your commute to work or school is easy with 417, 436, and Aloma Ave just minutes from this quiet neighborhood. This property features a comfortable living space with essential amenities to enhance your lifestyle. Please note that utilities such as electricity, Water/Sewer, cable, and internet are not included in the rent, but trash service, lawn maintenance, tennis courts and access to the lake (for non-motorized watercraft) are included. Don't miss out on this fantastic opportunity to experience the vibrant life in Winter Park! Schedule a viewing today to make this property your new home.
Listing is courtesy of: TOP VALUE PROPERTIES LLC
COLONIES - S5154582 - 3035 GEORGE MASON AVE #D20, WINTER PARK, FL 32792 2 Days on yellowkey
$1,250 | Condo | 1 beds | 1.0 baths
Welcome to 3035 George Mason Avenue, Unit #20B—a cozy and inviting 1-bedroom, 1-bathroom retreat in the heart of beautiful Winter Park, Florida! This charming home offers a bright and comfortable living space, perfect for anyone looking for convenience and tranquility. Nestled within a friendly community, you'll enjoy access to a sparkling community pool, nearby shopping centers, supermarkets, and easy connections to major roads. The property is just minutes from Winter Park's vibrant dining, boutique shopping, cultural venues, and scenic parks. Whether you're unwinding at home, exploring nearby attractions, or making a quick trip to Orlando International Airport, this home is your ideal gateway to everything Winter Park has. Make this gem your next home today!
LAKE KNOWLES TERRACE ADD 02 - O6429182 - 1368 HIBISCUS AVE, WINTER PARK, FL 32789 2 Days on yellowkey
$7,500 | Single Family Home | 4 beds | 2.5 baths | 2 gar
Discover refined living in the heart of Winter Park in this beautifully appointed 4-bedroom, 2.5-bathroom single-family pool home. Immediately to the right of the entryway, a beautiful private office provides a convenient and quiet space for working from home or studying. Filled with natural light, the home features an inviting open layout, and a spacious living area centered around a cozy fireplace. The stylish kitchen showcases light gray cabinetry, sophisticated gold-tone accents, a center island, and generous space for cooking and entertaining. The primary suite offers a peaceful retreat with a spa-inspired bathroom featuring a soaking tub and a spacious walk-in closet. Outside, enjoy a private oasis with a sparkling pool and a balcony overlooking the outdoor living area—perfect for relaxing or entertaining. Additional highlights include a two-car garage, an oversized driveway with ample parking, and an excellent location on a residential street in highly desirable Winter Park. Available for a minimum lease term of seven months. Schedule your private showing today.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO
H VANWIES SUB - O6429250 - 1434 MINNESOTA AVE, WINTER PARK, FL 32789 2 Days on yellowkey
$1,495 | Half Duplex | 2 beds | 1.0 baths | 1 gar
Renovated two bedroom and one bath Midcentury Modern unit with a garage and laundry room located in the heart of Winter Park's industrial district.
Listing is courtesy of: COLDWELL BANKER REALTY
ALBERT LEE RIDGE FIRST ADD - O6428494 - 2401 ALBERT LEE PKWY, WINTER PARK, FL 32789 3 Days on yellowkey
$3,150 | Single Family Home | 3 beds | 2.0 baths | 1 gar
Gorgeous 3/2 Mid-century Modern Style Home with a Covered Patio and a Large Backyard in the Desirable Albert Lee Ridge Community - Winter Park! Available Now! Nestled in Lake Wilderness is a hidden gem, with homes only lining one side of the lake offering picturesque sunsets and views. This gorgeous home welcomes you into a bright and airy living space with a floor plan that offers versatility, privacy and convenience. Tile flooring flows throughout the main living areas and cozy carpet flooring in the bedrooms. Near the entrance you will find a spacious bedroom which can be used as an office, studio or additional living space. The updated kitchen boasts modern stainless steel appliances with plenty of countertop and cabinet space. Additionally, there's a home bar with a wine fridge so you can prepare your favorite drinks during the hot summer days. The large dining room has access to the covered patio, which is perfect for al fresco dining, cookouts and outdoor activities. You can relax and unwind on the patio overlooking the backyard, oak trees and the beautiful lake view. The master bedroom is a true retreat offering space for relaxation and comfort, plus an ample walk-in closet. The secondary bedroom is also very spacious with a shared bathroom for convenience. This home also offers an inside utility room (Washer and Dryer hook-ups only) and a 1 car garage with an extended driveway for extra parking. Don't miss it! Great location within walking/biking distance to the key attractions in Winter Park: Ravaudage, Winter Park Villages, Lakeside Crossings, Hannibal Square and Park Ave. Easy access to major roads and a short drive to Downtown Orlando offering a range of shopping, restaurants and entertainment options. Pets will be considered. All residents are enrolled in the Resident Benefits Package which includes AC filter delivery, utility concierge, our best-in-class resident rewards program, and much more! More details in our Rental Selection Criteria or upon application. NO SIGHT UNSEEN APPLICATIONS. [21G]
Listing is courtesy of: VERANDAH PROPERTIES INC
LAKE KNOWLES TERRACE 2ND ADD - O6421394 - 1442 PALM AVE, WINTER PARK, FL 32789 4 Days on yellowkey
$9,900 | Single Family Home | 5 beds | 6.0 baths | 2 gar
Gorgeous 5-bedroom /6-bathroom Luxury Estate with Guest House & Pool in Winter Park This stunning two-story home offers the perfect blend of luxury and comfort right in the heart of Winter Park. At the center of the home is a beautiful open kitchen outfitted with high-end appliances, solid wood cabinets, and granite countertops . A true chef’s layout that flows into the living spaces. You'll love the elevated details throughout, from the elegant crown molding to the beautiful flooring. The backyard is a private retreat, featuring an inviting in-ground concrete pool, an outdoor shower, and a separate guest house that offers fantastic flexibility. Location-wise, it doesn't get better: you're within premier Winter Park school zones and just a short walk away from the area's best boutiques and restaurants. Available for long-term lease.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS
WINTER PARK GARDENS CONDO - O6428424 - 700 MELROSE AVE #A5, WINTER PARK, FL 32789 4 Days on yellowkey
$2,350 | Condo | 2 beds | 2.0 baths
Beautifully upgraded 2-bedroom, 2-bath condo in the heart of Winter Park! Located in a sought-after 55+ community surrounded by mature, lush landscaping, this charming condo offers the perfect blend of comfort and convenience. Enjoy a short walk to Mead Botanical Garden or the shops, dining, and entertainment along Park Avenue. With easy access to I-4, downtown Orlando, hospitals, shopping, and everything Central Florida has to offer, this is Winter Park living at its finest!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES
ENCLAVE AT ALOMA - O6424160 - 8104 PLEASANT PINE CIR, WINTER PARK, FL 32792 7 Days on yellowkey
$2,950 | Single Family Home | 4 beds | 2.0 baths | 2 gar
WINTER PARK 4BR/2BA, Single Story, Built in 2016. Located in the GATED COMMUNITY of Enclave At Aloma. Fantastic open floor plan. Plank wood-looking ceramic tile throughout the entire home. Loads of options. House was extended 4 feet to increase the size of dining room, great room, and master bedroom. 10' x 40' Covered Lanai in the rear. Center Island with Pendant Lighting in the Kitchen. Stainless Steel Appliances, Upgraded Cabinets, Crown Molding. Solid Surface Counters throughout the home. Volume Ceilings & Recessed Lighting. Master Bathroom has dual sinks, a huge walk in shower with a seat, and private toilet closet. Inside utility room with washer/dryer hook-ups. Easy access to the major highways 417, 426, 436, and a short commute to downtown Winter Park. First, Last & Security are required. No smoking or vaping. No pets
Listing is courtesy of: LAKEFRONT REALTY, INC.
- O6427633 - 2234 HOWARD DR, WINTER PARK, FL 32789 8 Days on yellowkey
$8,295 | Single Family Home | 4 beds | 5.5 baths | 2 gar
Welcome to an extraordinary two-story, 4-bedroom, 5.5-bath executive estate nestled in one of Winter Park's most sought-after neighborhoods. Designed with timeless elegance and modern convenience, this expansive home effortlessly blends luxury, comfort, and versatility. Inside, vaulted ceilings create a grand sense of space, while multiple living areas offer flexibility for both formal entertaining and casual gatherings. The gourmet kitchen is a chef's dream, complete with an enormous walk-in pantry, high-end appliances, and seamless flow into the dining area. Entertain in style with a wet bar and food service station, perfect for hosting elegant dinners or festive celebrations. Master Suite is an expansive sanctuary that features a spa-like bathroom equipped with a soaker tub, walk-in shower, His and Her vanities Step outside to your private heated lap pool, perfect for fitness or relaxation. The backyard retreat is surrounded by lush landscaping an ideal oasis for quiet relaxation or sunny Florida afternoons. A first-floor bedroom with en-suite bath adds convenience for guests or multi-generational living. Perfectly situated near Audubon Park and Baldwin Park, this home offers unbeatable access to top-rated schools, including Audubon Park K-8 & Winter Park H.S. Ideally situated near Downtown Orlando, Rollins College, hospitals, renowned restaurants, and boutique shopping, making it a prime location for those seeking convenience and accessibility. Explore numerous community parks, perfect for those who enjoy an active outdoor lifestyle. An area rich in culture with nearby museums to explore and learn. This is more than just a home it's a lifestyle. Experience the best of Winter Park living: elegant, elevated, and effortlessly connected. Pets negotiable with owner approval. Additional fees may apply.