Location: Winter Park, 32789
Do Not Show Listings
503 KILSHORE LN, WINTER PARK, FL 32789
$2,05043 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)
1814 BARKER DR, WINTER PARK, FL 32789
$10,000103 Days on yellowkey MLS ID: O6395037
0 Days Off yellowkey (back on 6/24/2026)
REDUCED by $1,000 (9.1%) on 05/13/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4200 Built: 2021Community: South Lakemont ShoresSingle Family
Elementary School: Baldwin Park Elementary
High School: Winter Park High
Middle School: Glenridge Middle
Remarks: Stunning newer-construction luxury home in Winter Park offering 5 bedrooms, 4 baths, and 4,100 sq ft of modern living. Sleek architectural lines, abundant natural light, and seamless indoor–outdoor flow define this exceptional residence. The chef’s kitchen features premium stainless steel appliances, breakfast bar, custom cabinetry, and a large walk-in pantry. The spacious living area includes a reclaimed Chicago brick fireplace and full-length sliders opening to a resort-style lanai with summer kitchen, wood ceiling, and recessed lighting. Step outside to a private backyard oasis with a sparkling pool, outdoor kitchen area, and no rear neighbors—perfect for entertaining. The first-floor primary suite offers complete privacy with a spa-inspired bath, soaking tub, walk-in shower, and dream closet. The main level also includes a private office, full bath, dining room, laundry room, and generous living spaces. Upstairs features a large loft, rumpus room, four additional bedrooms, and two beautifully designed baths. The oversized two-car garage provides high ceilings, storage, and a flex space ideal for bikes, fitness, or workshop use. Located minutes from Park Avenue dining, shopping, and entertainment, this home delivers luxury, comfort, and an unbeatable Winter Park lifestyle. Professionally managed with exceptional service.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Tab Bish Llc (855-450-0442)
2234 HOWARD DR, WINTER PARK, FL 32789
$8,29522 Days on yellowkey MLS ID: O6419042
Bed: 4 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3295 Built: 2019Community: Lake Forest Park S/20 Lot 26 Blk BSingle Family
Elementary School: Audubon Park K8
Remarks: Welcome to an extraordinary two-story, 4-bedroom, 5.5-bath executive estate nestled in one of Winter Park's most sought-after neighborhoods. Designed with timeless elegance and modern convenience, this expansive home effortlessly blends luxury, comfort, and versatility. Inside, vaulted ceilings create a grand sense of space, while multiple living areas offer flexibility for both formal entertaining and casual gatherings. The gourmet kitchen is a chef's dream, complete with an enormous walk-in pantry, high-end appliances, and seamless flow into the dining area. Entertain in style with a wet bar and food service station, perfect for hosting elegant dinners or festive celebrations. Master Suite is an expansive sanctuary that features a spa-like bathroom equipped with a soaker tub, walk-in shower, His and Her vanities Step outside to your private heated lap pool, perfect for fitness or relaxation. The backyard retreat is surrounded by lush landscapingan ideal oasis for quiet relaxation or sunny Florida afternoons. A first-floor bedroom with en-suite bath adds convenience for guests or multi-generational living. Perfectly situated near Audubon Park and Baldwin Park, this home offers unbeatable access to top-rated schools, including Audubon Park K-8 & Winter Park H.S. Ideally situated near Downtown Orlando, Rollins College, hospitals, renowned restaurants, and boutique shopping, making it a prime location for those seeking convenience and accessibility. Explore numerous community parks, perfect for those who enjoy an active outdoor lifestyle. An area rich in culture with nearby museums to explore and learn. This is more than just a homeit's a lifestyle. Experience the best of Winter Park living: elegant, elevated, and effortlessly connected. Pets negotiable with owner approval. Additional fees may apply.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Raquel Elliott (407-921-3772)
501 W CANTON AVE, WINTER PARK, FL 32789
$6,50025 Days on yellowkey MLS ID: O6418569
0 Days Off yellowkey (back on 6/20/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2372 Built: 2022Community: Vilasa TwnhmsTownhouse
Elementary School: Lakemont Elem
Remarks: Look no further, this luxury Modern Townhome offers premium location just minutes from Park Avenue, restaurants, shopping, Hannibal Square, and Rollins College just to name a few! Through the front door you are met with 13-foot ceilings, Modern finishes, Pella double windows, and wood flooring throughout. The Chef’s gourmet kitchen is complete with high-end flat panel cabinetry, Quartz countertops, Wolf gas cooktop, and Subzero appliances! On the second floor there are three bedrooms, 2 full bathrooms, utility room and the spacious primary bedroom is equipped with an oversized walk-in closet, opulent tub, walk-in shower, and Quartz countertops. Schedule your private showing today!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Nicole Howell (321-217-7918)
784 S PENNSYLVANIA AVE, WINTER PARK, FL 32789
$5,50057 Days on yellowkey MLS ID: O6408937
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1940 Built: 1988Community: Pennsylvania Station 01 CondoTownhouse
Elementary School: None
High School: None
Remarks: Discover modern living in this beautifully designed townhome located in the heart of Winter Park. This residence has a spacious layout with contemporary finishes, high ceilings, modern light fixtures and shades, and abundant natural light. Enjoy the convenience of a well-appointed kitchen, an inviting living area, and a private patio for relaxing, and private access to the community pool! The property provides access to community amenities and is situated near local shops, dining, and entertainment venues. Experience the vibrant lifestyle Winter Park has to accord.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
438 LAKEVIEW AVE, WINTER PARK, FL 32789
$3,200102 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
$2,900116 Days on yellowkey MLS ID: GC538622
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1056 Built: 1999Community: Winter ParkSingle Family
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)
2011 CORNELL AVE #3, WINTER PARK, FL 32789
$80097 Days on yellowkey MLS ID: O6396986
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 265 Built: 1940Community: Stansbury EstatesApartment
Remarks: Beautifully renovated private studio unit (1 bed / 1 bath) located in the rear of the property in a highly desirable area near Winter Park and Downtown Orlando. This cozy detached unit offers a comfortable living space with a private bathroom, ideal for a single professional or student looking for convenience and privacy. Water and electricity are included in the rent, making it an easy and budget-friendly option. The main house and the additional front unit are currently occupied, while this rear studio offers its own separate and peaceful setting. Excellent location with easy access to I-4, Downtown Winter Park, Downtown Orlando, shopping, dining, and Dubsdread Golf Course.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Andres Ospina Rivera (321-821-8446)
1695 LEE ROAD RD #C110, WINTER PARK, FL 32789
$1,400159 Days on yellowkey MLS ID: O6377466
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 638 Built: 1966Condo
Elementary School: Hungerford Elem
Remarks: Spacious first floor unit in Waterfall Cove 1 bedroom, charming residential unit , This inviting space offers a comfortable layout with plenty of natural light. Conveniently located near shops, restaurants and parks. It is perfect for enjoying the Winter park lifestyle.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Yigit Orer (407-948-5347)
782 S PENNSYLVANIA AVE #1, WINTER PARK, FL 32789
$5,490 MLS ID: O6380197
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2354 Built: 1988Community: Pennsylvania Station 01 CondoCondo
Remarks: Welcome to this charming condominium in Winter Park! This home features a spacious living area with ample natural light, a modern kitchen with sleek appliances, and large bedrooms. Enjoy the convenience of nearby shopping, dining, and entertainment. The community provides well-maintained amenities for residents to enjoy. With its prime location, this condo provides easy access to all that the vibrant Winter Park area has to accord. Don't miss the opportunity to make this your new home!
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