Location: Pines, Winter Park
Do Not Show Listings
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)
3121 HEARTWOOD AVE, WINTER PARK, FL 32792
$2,45046 Days on yellowkey MLS ID: S5148754
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1627 Built: 1981Community: Bel Aire PinesSingle Family
Elementary School: Aloma Elem
Remarks: Discover this beautifully updated 3-bedroom, 2-bathroom home located in a highly sought-after neighborhood in Winter Park, served by A-rated schools. This property features stunning ceramic tile flooring throughout, a modern kitchen equipped with stainless steel appliances and elegant quartz countertops, and luxurious upgraded bathrooms that offer both style and comfort. Relax on the inviting front screened patio or entertain friends and family in your spacious backyard, which is enclosed by a privacy fence for added enjoyment. Ideally situated, this home provides quick access to shopping, vibrant Downtown Orlando, and nearby colleges, making it a perfect choice for families and professionals alike. SCHEDULE YOUR VIEWING TODAY!!
Listing is courtesy of: DELUXE REALTY OF CENTRAL FLORIDA (407-904-4974)
Listing Agent: Haimdatt Sadoo (321-388-4128)
2730 PRINCE JOHN RD, WINTER PARK, FL 32792
$2,4959 Days on yellowkey MLS ID: O6413831
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1669 Built: 1963Community: Winter Park Pines RepSingle Family
Elementary School: None
High School: None
Middle School: None
Remarks: Fantastic 4 Bed 2 Bath Winter Park Home with 2-car garage! Located in a highly desirable Winter Park area. Large living room/dining room combo, a large separate den area. The home has a large fenced-in backyard. Lawn care is included. Walking distance to the Cady Way Trail. *Bonus Amenity Included* -All RE/MAX 200 Realty Property Management Division 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. Pet Friendly Home (with approval and a non-refundable pet fee).
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
Listing Agent: Mo Jabr (407-571-1441)
2075 JEWELL AVE, WINTER PARK, FL 32789
$6,795104 Days on yellowkey MLS ID: O6386721
REDUCED by $100 (1.5%) on 06/04/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2918 Built: 2024Community: PinesSpa: YesSingle Family
Remarks: FULLY FURNISHED 5br/4b +bonus loft GEM! Welcome to 2075 Jewel Avenue, an exceptional residence nestled in the heart of Winter Park, 32789—one of Central Florida’s most sought-after communities. Ideally situated just minutes from the vibrant shops and dining along Park Avenue and the scenic beauty of Rollins College, this home offers the perfect blend of charm, convenience, and lifestyle. Set on a picturesque street, the property boasts inviting curb appeal with mature landscaping and a welcoming entrance. Inside, thoughtfully designed living spaces feature abundant natural light, an open and functional layout, and seamless flow ideal for both everyday living and entertaining. The private backyard provides a serene retreat with ample space for relaxing or hosting gatherings. Step outside to your fully fenced backyard, complete with a private hot tub and spacious patio, ideal for relaxing evenings or casual get togethers. With no pool to maintain, you'll enjoy low maintenance outdoor living in a peaceful setting.1 time cleaning per month and wifi included. Located near top-rated schools, parks, and cultural attractions, 2075 Jewel Avenue presents a rare opportunity to enjoy refined living in one of Florida’s most prestigious neighborhoods. Mid term lease available.
Listing is courtesy of: URBANISTA BROKERS (407-619-7272)
Listing Agent: Paul Jimenez (407-276-3516)
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.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Jackie O'Leary (407-718-0887)
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