Displaying: For Rent
Location: Winter Park
Property Type(s): Single Family
Price: $2,000 to $2,499
Do Not Show Listings
Winter Park - 7 properties found
503 KILSHORE LN, WINTER PARK, FL 32789
$2,05023 Days on yellowkey MLS ID: O6412456
REDUCED by $200 (8.9%) on 06/24/2026
Bed: 2 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 1125 Built: 1952Community: NoneSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Killarney Elem
High School: Edgewater High
Tax Year:
Middle School: None
Remarks: LOCATION! LOCATION! LOCATION! Home well positioned on large 0.28 acre lot in 32789. Gorgeous two bedroom home right in the heart of Winter Park , that just had a new roof put on.. At just a ten minute drive from Orlando, this home is in a very convenient location for anyone who wants to be in and out of the city whenever they'd like. Beautiful interior, with original wood flooring throughout. Tile in the spacious open kitchen that opens into the living room, giving this home a wide-open layout. Enjoy, the peaceful, secluded feeling when lounging on the deck in the generous backyard during warm summer nights. Large, fenced backyard. Lake Killarney access for kayaking and canoeing.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Vincent Paige, Pa (407-256-8190)
5117 LAKE HOWELL RD, WINTER PARK, FL 32792
$2,395Listed 06/24/2026 6:24AM MLS ID: O6419550
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1300 Built: 1957Community: Tanglewood Sec 3 RepSingle Family
Elementary School: None
High School: None
Remarks: 3/1, Carport, Single Family Home, Living Room, Dining Room, Eat in Kitchen, Stainless Steel Appliances Included: Stove, Microwave, Refrigerator, Dishwasher, Disposal, Inside Utility Room with Washer and Dryer Hookups, Laminate Wood Flooring & Ceramic Tile Throughout, Fenced Backyard, Pets Ok Upon Owner's Approval, NO SMOKING, Year Built: 1957/1300 Sqft.
Listing is courtesy of: LEGENDS REALTY (407-333-1010)
Listing Agent: Tina Lopez (407-333-1010)
7522 LAUREL SPRINGS DR, WINTER PARK, FL 32792
$2,2001 Day on yellowkey MLS ID: O6419181
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1106 Built: 1972Community: Laurel SpgsSingle Family
Remarks: Located in the highly sought-after Winter Park High School district, this beautifully maintained 3-bedroom, 2-bath home in Laurel Springs provides comfort, space, and convenience. The bright and inviting living area features vinyl flooring and an open, welcoming feel. Enjoy year-round indoor-outdoor living in the expansive 400+ sq. feet. enclosed patio overlooking a fully fenced backyard—perfect for entertaining, relaxing, or family gatherings. Ideally situated with easy access to shopping, dining, parks, and major highways. Move-in ready!!!!
Listing is courtesy of: JOY ESTATE ENTERPRISE INC (321-754-9131)
Listing Agent: Liu Zhang (917-892-2868)
2242 KING JOHNS CT, WINTER PARK, FL 32792
$2,39522 Days on yellowkey MLS ID: O6411882
0 Days Off yellowkey (back on 6/19/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1470 Built: 1969Community: Winter Woods Unit 01Single Family
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: This beautiful 3 bedroom, 2 bathroom home is located in the heart of Winter Woods in desirable Winter Park. This home offers a spacious split floor-plan with an open living/dining area. Features include tile throughout, a fenced-in backyard with patio area, 2 car garage, washer/dryer hookups, and is convenient to schools, recreational parks, restaurants, & the lovely downtown Winter Park. Please note the outdoor hot tub/spa does not work and will not convey. Pets under 50 lbs. 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 (407-897-3366)
Listing Agent: Matthew Kirsch (407-897-3366)
1947 SUMMERFIELD RD, WINTER PARK, FL 32792
$2,49968 Days on yellowkey MLS ID: O6396107
REDUCED by $100 (3.8%) on 06/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1422 Built: 1956Community: Kenilworth Shores Sec 07Single Family
Elementary School: Brookshire Elem
High School: Winter Park High
Middle School: Glenridge Middle
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)
3121 HEARTWOOD AVE, WINTER PARK, FL 32792
$2,45057 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
$2,49520 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
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)
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