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LAKE KNOWLES TERRACE ADD 02 - O6401835 - 1571 MAGNOLIA AVE, WINTER PARK, FL 32789 Just Added on 04/23/2026 6:31PM
$2,350 | Single Family Home | 2 beds | 1.5 baths | 1 gar
Fantastic bungalow in sought-after Winter Park. Great location, close to Advent Hospital Winter Park, Park Avenue, 10 minutes to I4. Large, fenced-in backyard, original hardwood floors in living area & bedrooms. Stainless appliances, granite countertops in kitchen, one car garage. Tons of natural light, indoor laundry.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES
OLYMPIA HEIGHTS ANNEX - O6401803 - 2176 CRANDON AVE, WINTER PARK, FL 32789 Just Added on 04/23/2026 2:17PM
$2,700 | Single Family Home | 2 beds | 1.0 baths | 1 car
Fully furnished and Turnkey/Renovated in-town home. Close to downtown Winter Park, Advent and Orlando Health. Newly renovated kitchen with Sub-Zero/Cafe appliances. Monthly rental only…2 bedrooms sleeps 4. Nice covered/screened porch. Available now. Weekly to monthly rental.
Listing is courtesy of: CORCORAN PREMIER REALTY
KAROLINA ON KILLARNEY - O6401484 - 1931 STAUNTON AVE, WINTER PARK, FL 32789 1 Day on yellowkey
$2,350 | Single Family Home | 3 beds | 2.0 baths | 1 car
Available for rent! Tucked onto a desirable corner lot just steps from Lake Killarney, this beautifully updated 3 bedroom, 2 bath single-family home puts you in one of the area's most sought-after spots. Walkable, quiet, and moments from the water. Inside, the home is move-in ready with a full suite of brand-new appliances (dishwasher, range, and refrigerator) plus washer/dryer hookups ready for your setup. Three comfortable bedrooms, two full baths, and bright, livable spaces make it easy to settle in from day one. Easy parking thanks to a covered carport and private driveway. Pets welcome on a case-by-case basis. Available now. Security deposit equal to one month's rent; move-in total is first month + security deposit. Tenant responsible for all utilities and minor maintenance (bulbs, filters); landlord handles major repairs and pest control.
Listing is courtesy of: SAND DOLLAR REALTY GROUP INC
GEORGETOWN ESTATES - O6401263 - 3131 LOWNDES DR, WINTER PARK, FL 32792 1 Day on yellowkey
$3,995 | Single Family Home | 4 beds | 2.0 baths
Beautiful 4 Bedroom Furnished House with a Pool! This home has an Eat-In Updated Kitchen. There are 3 bedrooms and a bathroom on one side and a large master suite on the other side with a fireplace. The master bathroom has an extra large walk-in shower with a double mirrored dressing area. There is a family room/ FLex Space/ Office Area with a Roku TV, Desk, and Wi-Fi. There is no garage. It has 2 sheds for storage in the back. The neighborhood is nice and quiet. It is conveniently located near Hospitals, Businesses, Restaurants, Schools and Shopping.
Listing is courtesy of: A +ROI PROPERTY
TUSCANY PLACE FIRST ADD - O6401030 - 1041 TUSCANY PL, WINTER PARK, FL 32789 2 Days on yellowkey
$12,000 | Single Family Home | 4 beds | 3.5 baths | 2 gar
Nestled along a quiet brick-lined street in Winter Park’s coveted Via’s neighborhood, 1041 Tuscany Place offers a rare blend of elegance, comfort, and breathtaking natural beauty. From nearly every room, this exceptional residence captures tranquil views of the private backyard and picturesque Lake Temple beyond. Inside, a thoughtfully designed open floor plan is enhanced by soaring vaulted ceilings and an abundance of natural light, creating a warm yet sophisticated atmosphere. The gourmet kitchen is beautifully appointed with premium Wolf appliances, a Sub-Zero refrigerator, quartz countertops, imported Italian cabinetry, and a striking mother-of-pearl mosaic backsplash. The primary suite serves as a peaceful retreat, complete with serene landscape views and a spa-inspired bath featuring a spacious walk-in shower with skylights, body jets, and an oversized 40-inch rainfall showerhead. Upstairs, two generously sized bedrooms share a well-appointed Jack-and-Jill bath, offering comfort and privacy for family or guests. Outdoor living is just as impressive. A spacious deck invites you to relax and entertain while overlooking the sparkling pool and hot tub, while the lower decks bring you into nature with an inviting fire pit overlooking the water. The expansive, beautifully landscaped backyard provides a private setting to enjoy the best of Florida living. Ideally located just minutes from the Winter Park Racquet Club, Interlachen country club, Lake Maitland, and the shops and dining of Park Avenue, this home offers an extraordinary lifestyle in one of Winter Park’s most desirable settings.
Listing is courtesy of: COMPASS FLORIDA LLC
KENILWORTH SHORES SEC 07 - O6400730 - 1026 S LAKEMONT AVE, WINTER PARK, FL 32792 2 Days on yellowkey
$4,300 | Single Family Home | 3 beds | 2.0 baths | 2 car
Lawn and pool maintenance included in rent! Welcome to this beautifully upgraded Winter Park pool home, designed for effortless living and exceptional entertaining. This 3-bedroom, 2-bath residence offers an open, inviting floor plan with a spacious kitchen featuring updated countertops and cabinetry, stainless steel appliances, beautiful bathroom finishes and updated flooring throughout. The home truly shines outdoors, offering an abundance of entertaining space. Enjoy a screened-in pool, covered patio, and multiple seating areas including a tiled lounge space with a firepit, all set within a large, fenced backyard with both lush grass and low-maintenance turf. Whether hosting guests or enjoying a quiet evening, this home provides the perfect setting. Inside, the light-filled dining room overlooks the backyard from three sides, while the primary suite features a spacious closet and private en-suite bath. All bedrooms include newer carpet, and a generous utility room off the carport offers ample space for laundry and storage. Located in a highly rated school zone and just minutes from Rollins College, parks, shopping, dining, and everything Winter Park has to offer, this home delivers both lifestyle and convenience in one exceptional rental opportunity.
Listing is courtesy of: SOTERA LIVING
FERNBROOK TRAILS PH 3 - O6400973 - 5523 CRETAN WAY, WINTER PARK, FL 32792 2 Days on yellowkey
$2,195 | Single Family Home | 3 beds | 2.0 baths
3 bedroom, 2 bathroom townhouse in highly desired Winter Park. Small and quiet neighborhood with private driveway parking and a cul de sac with no neighbors on one side. Amenities include: central air, central heat, dishwasher, garbage disposal, side-by-side fridge, electric stove/oven, gas grill, Maytag full-size washer/dryer set, yard, shed for storage, and mini bar off of the living room, and lawn service included. *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.
Listing is courtesy of: RE/MAX 200 REALTY
KENILWORTH SHORES SEC 07 - O6396107 - 1947 SUMMERFIELD RD, WINTER PARK, FL 32792 6 Days on yellowkey
$2,699 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Welcome home! This fantastic 3-bedroom, 2-bath home is available for immediate move-in! This property is a short drive from downtown Winter Park, the Crosby Center for Health and Wellbeing, Cady Way Park, and more! , this property features a comfortable layout with well-apportioned bedrooms and bathrooms, a lovely kitchen with lots of counter and cabinet space, and many desirable features. Act now! This one won't last long! All applicants are required to do a credit and background check. 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