Displaying: For Rent
Location: Winter Park
Property Type(s): Single Family
Price: $3,500 to $4,999
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Winter Park - 8 properties found
1815 BARKER DR, WINTER PARK, FL 32789
$4,00066 Days on yellowkey MLS ID: O6386321
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1548 Built: 1959Community: South Lakemont ShoresSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Baldwin Park Elementary
High School: Winter Park High
Tax Year:
Middle School: Glenridge Middle
Remarks: 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 (407-725-9660)
Listing Agent: Benjamin Cole Iv (407-399-0629)
1091 WILDMEADOW RUN, WINTER PARK, FL 32792
$4,00053 Days on yellowkey MLS ID: O6389834
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2196 Built: 2021Community: Hawks CrestSingle Family
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Newer home for rent in the gated new community of Hawks Crest. The home offers both style and flexibility. The first floor is graced with an openness that invites you in and makes you feel welcome. The plan features options to help you personalize the home to your needs and preferences. Entering the home, you walk into an expansive space. A flex room with 2-story ceiling can be used as a formal living room if you like. This room leads to the dining room, which looks out to a lanai. The kitchen opens to both rooms, as well as the gathering room at the back of the home. Spending time in the kitchen is a pleasure. The plentiful counter space lets you spread things out when preparing a meal. U-shaped, one arm of the counter holds the sink and looks into the gathering room. The kitchen offers gourmet upgrades, built in brand new appliances, granite counter top, touchless faucet. The upstairs layout is split, with the owner’s suite on one side and the three additional bedrooms with shared bathroom on the other. The suite features a bedroom, huge walk-in closet and bathroom with dual sinks, private commode, soaking tub and separate shower. Transform the suite into a retreat with the addition of a sitting room. Gated community with access to lake Howell, gym, swimming pool, clubhouse and playground.
Listing is courtesy of: FORTUNE INTERNATIONAL REALTY (305-400-6393)
Listing Agent: Maggie Walas (407-701-0144)
1409 LONE FEATHER TRL, WINTER PARK, FL 32792
$3,89510 Days on yellowkey MLS ID: O6401907
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2553 Built: 2022Community: Landings At Hawks CrestSingle Family
Remarks: Beautiful tile roof single-family house is available in Hawks Crest, the only newal gated community in Winter Park! No rear neighbors! Landscape/Lawn Care and Reclaimed Water Bill are paid by landlord. UV sanitizing lights installed in all bathrooms. Water filter system installed in kitchen sink. This 4 bed 3.5 bathrooms plus an office and second floor loft is ready to move-in . When you enter the home, an open concept floor plan leads you to the family room, the kitchen / nook area combined. 20-foot high ceiling family room with wide sliding doors to the back patio and high windows gives you plenty of natural sunlight. The large covered lanai would be great for a morning coffee, evening wine, of course family gatherings and BBQ. The Master bedroom is located on first floor. The community is just a few minutes to Costco, Super Target, Publix, Trinity Prep School, and Full Sail University. Located along the southern shores of beautiful Lake Howell, Hawk's Crest provides easy access to major employment sectors and desirable Winter Park shopping and dining destinations including Park Ave and Winter Park Village. As you enjoy convenience location, you will benefit from these wonderful amenities within the community: Community pool, Clubhouse, Party Room, Dog Park, Free Gym, Grilling Area, Kid's Splash Pad, Lake Park Picnic Tables, Playground, Cabana, Play Lawn, Lakeside Dock and Future Kayak Access. Come and see your new home today, don't miss this chance.
Listing is courtesy of: EAST PEARL REALTY (407-802-6859)
Listing Agent: Yan Zuo (407-435-3142)
1711 CHESTNUT AVE, WINTER PARK, FL 32789
$4,15031 Days on yellowkey MLS ID: O6396000
0 Days Off yellowkey (back on 4/22/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2288 Built: 1963Community: Conwill EstatesSpa: NoSingle Family
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: 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.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Drew Henner (407-406-0662)
1026 S LAKEMONT AVE, WINTER PARK, FL 32792
$4,30013 Days on yellowkey MLS ID: O6400730
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1953Community: Kenilworth Shores Sec 07Spa: NoSingle Family
Elementary School: Brookshire Elem
Remarks: 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 Agent: Lianna Dangelo (321-446-3509)
2115 SYCAMORE DR, WINTER PARK, FL 32789
$3,50020 Days on yellowkey MLS ID: O6398548
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2099 Built: 1953Single Family
Elementary School: None
Middle School: Audubon Park K-8
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)
668 OVERSPIN DR, WINTER PARK, FL 32789
$4,20042 Days on yellowkey MLS ID: O6392773
0 Days Off yellowkey (back on 4/3/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2509 Built: 2018Community: Dubsdread HeightsSingle Family
Elementary School: Princeton Elem
High School: Edgewater High
Middle School: College Park Middle
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)
1317 MEDINAH CT, WINTER PARK, FL 32792
$3,65038 Days on yellowkey MLS ID: O6393971
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2015 Built: 1979Community: Greenview At Winter PinesSingle Family
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)
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