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LAKE KNOWLES TERRACE 2ND ADD - O6421394 - 1442 PALM AVE, WINTER PARK, FL 32789 1 Day 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 2 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 5 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 6 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.
Listing is courtesy of: COLDWELL BANKER REALTY
VISTAS AT LAKE HOWELL - O6423277 - 2508 GALLIANO CIR, WINTER PARK, FL 32792 9 Days on yellowkey
$2,195 | Townhouse | 3 beds | 2.5 baths | 1 gar
This 3 bedroom, 2.5 bathroom townhouse is located on a quiet street in the gated community of Vistas at Lake Howell near local shops, restaurants, and Winter Park schools. Features include a spacious main living area with lake views from the living room, a lovely eat-in kitchen, half bathroom downstairs, beautiful primary suite with big walk-in closet and volume ceiling, dual vanity and walk-in shower/tub in the bathroom, a screened patio, and 1 car garage. The community has a picnic gazebo and walking trails. Sorry, no students or pets. Schedule a showing or submit an application online. All Real Property Management & Realty residents enjoy convenience and well-maintained homes, with our safe and secure online portal where you can submit maintenance requests and pay online with multiple payment options, and a 24/7 emergency maintenance response team. Please note the listed amenities may not be accurate.
Listing is courtesy of: REAL PROPERTY MANAGEMENT AND REALTY
BROOKSHIRE HEIGHTS 2ND ADD - O6421916 - 648 FITZWALTER DR, WINTER PARK, FL 32792 9 Days on yellowkey
$4,400 | Single Family Home | 3 beds | 2.0 baths | 1 gar
Nestled beside Cady Way Park & Trail, this charming home offers an unbeatable location in a quiet, established neighborhood on a peaceful tree-lined cul-de-sac. Enjoy easy access to top-rated Winter Park schools, Winter Pines Golf Club, Showalter Field, AdventHealth Winter Park, Baldwin Park, Downtown Winter Park, and a wide variety of shopping, dining, and entertainment. Inside, you’ll find beautiful terrazzo floors throughout much of the home, with ceramic tile in the spacious family room. The bright kitchen features a window overlooking the large backyard, solid wood cabinetry, and a cozy eat-in dining area. Tastefully updated bathrooms add a fresh, modern touch. The flexible floor plan includes: * Living room * Dining area * Eat-in kitchen * Expansive family room with French doors leading to an outdoor deck and large fenced backyard. Zoned for highly sought-after schools: * Brookshire Elementary * Glenridge Middle School * Winter Park High School This home combines a prime location, comfortable living spaces, and excellent schools—making it a wonderful place to call home.
Listing is courtesy of: LOVEJOY PROFESSIONAL REALTY, INC
VIRGINIA HEIGHTS REP - O6419129 - 1261 RICHMOND RD, WINTER PARK, FL 32789 10 Days on yellowkey
$2,099 | Single Family Home | 2 beds | 1.0 baths | 1 car
Available on July 29th 2026!! CHARMING AND UNIQUE two bedrooms /one bath home in the heart of Winter Park down street from Mead Botanical Gardens. This home still has a lot of its original charm and features beautiful wood floors extending through out. Tons of natural light that flood the interior from all the windows that wrap the entire exterior, open and airy floor plan that makes it feel double the size. Kitchen features gas stove and refrigerator. Also enjoy a great Florida room off the kitchen overlooking the huge back yard. WALK TO PARK AVENUE, ROLLINS COLLEGE, LAKE VIRGINIA, AND MORE. All applicants are required to do a credit and background check. Renters insurance is required. **Pets allowed 60lbs max** 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
PARK AIRE CONDO - O6425848 - 640 N PARK AVE #4, WINTER PARK, FL 32789 11 Days on yellowkey
$2,200 | Condo | 1 beds | 1.0 baths
Welcome to the heart of Winter Park! This beautiful first floor condo is located in one of the town’s most iconic buildings, Park Aire. Nestled between the famous Winter Park Golf Course and downtown area where shopping and dining are a must! Other close by attractions include, the Morse Museum, Central Park, Hannibal Square and Scenic Boat Tours. This updated condo features beautiful wood floors, updated kitchen, and nice view from oversized windows. Park Aire has a beautiful private pool area and lush garden area as well as reserved underground parking. This is a great opportunity to live on one of the most well known streets in Central Florida! Call for your showing today! Water and basic internet included. NO PETS and NO SMOKING
Listing is courtesy of: UNITED REAL ESTATE PREFERRED
AUTUMN GLEN - O6425132 - 4059 WATERVIEW LOOP, WINTER PARK, FL 32792 12 Days on yellowkey
$2,650 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Welcome home to this beautifully maintained rental in one of Winter Park's most desirable neighborhoods, zoned for top-rated schools! This spacious 3-bedroom, 2-bath residence features a desirable split-bedroom floor plan, a 2-car garage, and an indoor laundry room complete with a brand-new washer and dryer. The interior has been freshly painted, giving the home a bright, clean, and move-in-ready feel. Designed for both comfortable living and entertaining, the home offers separate formal living and dining rooms, along with a spacious family room featuring a cozy fireplace. The kitchen boasts ample cabinet and counter space, a breakfast nook, and opens seamlessly to the family room, creating the perfect gathering space for family and friends. Step outside through the sliding glass doors to the oversized 23' x 12' screened porch overlooking a fully fenced backyard—ideal for relaxing, entertaining, or enjoying Florida's beautiful weather. Pets are welcome! Conveniently located just minutes from shopping, dining, Rollins College, Full Sail University, Downtown Winter Park, major roadways, parks, and everything Central Florida has to offer. Don't miss this exceptional rental opportunity! Schedule your private showing today, homes in this highly sought-after Winter Park location lease quickly.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK
WOODCREST UNIT 5 - S5153773 - 5354 LANYARD CT, WINTER PARK, FL 32792 13 Days on yellowkey
$3,699 Reduced | Single Family Home | 5 beds | 3.0 baths
Welcome to this spacious 5-bedroom, 3-bathroom home designed for comfort, functionality, and flexible living. One of the home’s standout features is a private area that includes two of the bedrooms and a full bathroom, offering added privacy and versatility. This thoughtfully designed layout creates the feel of two living spaces within one home, making it ideal for multi-generational living, extended guests, or anyone working from home who desires a more private area, while remaining part of the main residence. Step outside to enjoy the expansive backyard featuring a sparkling swimming pool—the perfect setting for relaxing, entertaining, and enjoying Florida’s outdoor lifestyle year-round. Conveniently located near shopping, dining, schools, and major highways, this home combines comfort, flexibility, and an excellent location.
Listing is courtesy of: JUPITER PROPERTIES, INC