Displaying: For Rent
Location: Winter Park
Property Type(s): Single Family
Living Area Square Feet: 1000 to 1499
Do Not Show Listings
Winter Park - 10 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)
1942 CONIFER CT, WINTER PARK, FL 32792
$1,750180 Days on yellowkey MLS ID: O6369312
REDUCED by $245 (12.3%) on 05/26/2026
Bed: 2 Bath: 1.0 Gar: 2 Liv Area Sq Ft: 1000 Built: 1968Community: Eastbrook Sub Unit 13Single Family
Remarks: Leasing nicely furnished 2 bedrooms, 1 bath, living room, dining room and kitchen in 3 bedroom / 2 bath home. Each bedroom has queen size bed and closet. The kitchen is fully equipped including dishes. The living room has a sofa and tv.The dining room has a table with 4 chairs. The porch has some chairs and a small table. Outside in the back yard is a table with 4 chairs - picnic in your own park like back yard. Ready to move in immediately.
Listing is courtesy of: BLACKFIN REALTY LLC (407-947-9722)
Listing Agent: Scott Banta (407-947-9722)
1540 ONECO AVE, WINTER PARK, FL 32789
$2,5005 Days on yellowkey MLS ID: O6413008
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1441 Built: 1959Community: Lake Knowles Terrace Add 02Single Family
Remarks: Nestled on a picturesque, tree-lined brick street, this charming 3-bedroom, 2-bath home offers an unbeatable location just minutes from Park Avenue, Rollins College, shopping, dining, and entertainment. Inside, you'll find a spacious floor plan featuring a formal living room, dining room, and family room, providing plenty of space for both relaxing and entertaining. The kitchen is equipped with all appliances and includes a breakfast bar along with a cozy eat-in dining area. Tile flooring runs throughout most of the home, with carpeting in one bedroom for added comfort. Additional features include an inside utility room with washer and dryer hookups, a large screened-in back porch perfect for enjoying Florida's beautiful weather, and a backyard storage shed for extra convenience. A two-car carport provides covered parking, and lawn care is included, making maintenance easy and worry-free.. All of our residents are enrolled in the Resident Benefits Package (RBP) for $39.95/month, which includes renters insurance, *RentSpree applications will not be accepted. Residents are enrolled in the Resident Benefits Package (RBP) for $39.95/month. More details upon application. This home combines charm, space, and convenience in one of the area's most desirable locations. Schedule your showing today!
Listing is courtesy of: WATSON REALTY CORP (407-359-2300)
Listing Agent: Tara Mason (407-501-1215)
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)
1404 CLAY ST, WINTER PARK, FL 32789
$2,80030 Days on yellowkey MLS ID: O6410414
0 Days Off yellowkey (back on 6/8/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1440 Built: 1948Community: Orwin Manor Westminster SecSingle Family
Remarks: FOR RENT | Available June 1st | Winter Park – Orwin Manor Area | Washer & Dryer in-unit | Lawn Maintenance included. Charming 3-bedroom, 2-bathroom updated residence. Offering 1,440 sq ft of comfortable living space, this older home blends character with modern updates and an unbeatable location. Step inside to find updated kitchen, bathrooms, vinyl flooring, abundant natural light, and a functional layout designed for everyday living. The home features an interior laundry room with washer and dryer included for added convenience. Enjoy outdoor living in the large, fully fenced backyard, for play & dogs. Lawn maintenance is included! Location truly is everything. Situated just 2 minutes from I-4, this home provides quick access to Downtown Orlando while keeping you close to some of Central Florida’s favorite destinations. You'll be within 10 minutes from Publix, Trader Joe’s, Winter Park Village, and Park Avenue, where you can enjoy boutique shopping, dining, and nearby Rollins College. You’ll have a new place to go to every weekend! PLEASE NOTE: A separate mother-in-law suite is located on the property and is currently occupied by a tenant. Call today for application or more info!
Listing is courtesy of: MEP REALTY INVESTMENTS LLC (407-992-9155)
Listing Agent: Mary Walason (321-274-6724)
438 LAKEVIEW AVE, WINTER PARK, FL 32789
$3,20082 Days on yellowkey MLS ID: O6396001
REDUCED by $200 (5.9%) on 05/06/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1250 Built: 1947Community: Killarney EstatesSingle Family
Middle School: College Park Middle
Remarks: Bring your boat and discover this charming Winter Park gem, perfectly nestled on a quiet, desirable brick-lined street. This inviting 2-bedroom, 1-bath home features beautiful hardwood floors and a warm, welcoming feel throughout. Enjoy a lakefront yard feet from the house that offers peaceful water views and the perfect setting for outdoor living. Step outside to an amazing backyard complete with a cozy firepit and large privacy bushes that create a secluded, tranquil retreat—ideal for relaxing evenings or entertaining guests. With a deeded dock and boat lift, you’ll have direct access to the Lake Killarney lifestyle you’ve been dreaming of. Come see this special home and start enjoying the lake life you deserve!
Listing is courtesy of: COLONIALTOWN REALTY (407-896-7300)
Listing Agent: Alexander Scures (407-925-5338)
540 W COMSTOCK AVE, WINTER PARK, FL 32789
$2,90096 Days on yellowkey MLS ID: GC538622
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1056 Built: 1999Community: Winter ParkSingle Family
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: Newly Renovated | Prime Winter Park Location | Move-In Ready Opportunity Positioned in one of Central Florida’s most desirable and high-demand areas, this newly renovated residence at 540 W Comstock Ave offers a rare opportunity for tenants seeking both location and lifestyle in the heart of Winter Park. Thoughtfully updated with modern finishes, the home features a clean, refreshed interior designed for today’s renter, delivering comfort, functionality, and style in a true turnkey living experience. Ideally located just minutes from Park Avenue, Rollins College, and Winter Park’s premier dining, shopping, and entertainment, this property places tenants in the center of one of Orlando’s most vibrant communities while still offering a sense of neighborhood charm and convenience. Its proximity to major roadways and local amenities makes it especially attractive for professionals, families, and relocation clients seeking both accessibility and quality living. This is a high-demand rental opportunity in a low-inventory pocket of Winter Park, and clean, updated homes in this location do not last. Agents are encouraged to bring qualified tenants ready to move quickly. Now accepting applications with expedited approvals available for well-qualified applicants.
Listing is courtesy of: KELLER WILLIAMS GAINESVILLE REALTY PARTNERS (352-240-0600)
Listing Agent: Fredrick Jacobs (352-790-1088)
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