Location: Winter Park
Keyword(s): Brookshire Elem
Keyword(s) Elementary School: Brookshire Elem
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418 R GILBERT RD, WINTER PARK, FL 32792
$4,0001 Day on yellowkey MLS ID: O6415814
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1680 Built: 1964Community: Winter Park Pines Ut 5Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Brookshire Elem
High School: Winter Park High
Tax Year:
Middle School: Glenridge Middle
Remarks: Beautifully renovated solid block home on a quiet street in highly desirable Winter Park Pines! This property features fresh exterior paint, updated lighting, a newly paved courtyard, and a bright open floor plan. The stunning kitchen offers modern cabinetry, quartz countertops, and brand-new stainless steel appliances, flowing seamlessly into the dining and family rooms. The sun-drenched Florida room is lined with windows that brighten the entire living space. Complete with a dry bar and its own mini-split AC unit, it offers flexible space for entertaining, relaxing, or creating your dream retreat. The split floor plan includes three generously sized bedrooms and three full renovated bathrooms, with a private primary suite with walk-in closet off the family room and the additional bedrooms and bath located on the opposite side of the home. The attached two-car garage offers excellent potential to be converted into a fourth bedroom, utilizing the existing full bathroom to create a private mother-in-law suite or guest quarters. Additional upgrades include new flooring, trim, doors, fixtures, and fresh interior paint. Create your own outdoor oasis with a newly paved patio and large fenced backyard with room for a pool. Ideally located near downtown Winter Park, Park Avenue shopping and dining, Cady Way Trail, and zoned for top-rated schools.
Listing is courtesy of: SOTERA LIVING (407-725-9660)
Listing Agent: Lianna Dangelo (321-446-3509)
2344 WOODCREST DR, WINTER PARK, FL 32792
$4,10019 Days on yellowkey MLS ID: O6410619
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1764 Built: 1960Community: Kenilworth Estates 1St AddSingle Family
Remarks: Resort Style Pool Home in KENILWORTH ESTATES! Conveniently located in Winter Park with a walking distance to Baldwin Park, Advent Health, Cody trail park! A short drive to Renown Rollin College, Park Ave, Full Sail University, downtown Orlando, theme parks, and UCF! Close to restaurants, shopping centers, bars, Publix, CVS and gas stations. Welcome Home! through the main door, you will be amazed by its modern and spacious floor plan! A lovely living room with a fireplace, an extra room for home gym or office, on the right, a sparkling pool in front of your eyesight through a modern glass sliding door, sitting under porch, enjoying family gathering in this resort style garden! There has a plenty closet space for storage. Spacious kitchen cabinets for cooking supplies. Be ready to live in a luxury and breath-taking Winter Park Pool home, while enjoying all Florida sunshine and outdoor biking, jogging and golfing at Winter Park Pine. Move in today!
Listing is courtesy of: EXPLORE FLORIDA REALTY SERVICES LLC (407-982-9709)
Listing Agent: Shannon Lee (407-982-9709)
1850 WHITEHALL DR, WINTER PARK, FL 32789
$3,350108 Days on yellowkey MLS ID: O6385792
0 Days Off yellowkey (back on 6/2/2026)
REDUCED by $125 (3.6%) on 05/30/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1670 Built: 1958Community: Kenilworth Shores Sec 06Single Family
Remarks: This is a wonderful pool home located in the sought after neighborhood of Kenilworth Shores in Winter Park. It features 3 bedrooms & 2 baths with an open floor plan. Family room/dining room combo, a wonderful Florida room overlooking the backyard & pool area. Enjoy the weekends lounging around the black bottom pool and the lush landscape surrounding the backyard. ALL UTILITIES included! The backyard also has a gazebo, is totally fenced in and has lots of room to roam. Conveniently located between Baldwin Park and Winter Parks Park Avenue. Winter Park School district. Sorry, no pets.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Jackie O'Leary (407-718-0887)
1947 SUMMERFIELD RD, WINTER PARK, FL 32792
$2,59957 Days on yellowkey MLS ID: O6396107
REDUCED by $50 (1.9%) on 05/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1422 Built: 1956Community: Kenilworth Shores Sec 07Single Family
Remarks: 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 (407-545-2594)
Listing Agent: Steven Simpson (407-545-2594)
1317 MEDINAH CT, WINTER PARK, FL 32792
$3,65078 Days on yellowkey MLS ID: O6393971
0 Days Off yellowkey (back on 4/3/2026)
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.
2356 COLDSTREAM DR, WINTER PARK, FL 32792
$2,82576 Days on yellowkey MLS ID: O6394600
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1619 Built: 1959Community: Brookshire HeightsSingle Family
Remarks: One or more photo(s) has been virtually staged. Lovely home in Winter Park school district. Closet to downtown Winter Park. Updated kitchen and baths on a Quiet street. Lawncare included.
Listing is courtesy of: VIA PROPERTIES LLC (321-229-6085)
Listing Agent: Donna Peebles (321-229-6085)
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