Location: Winter Park
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2923 ANTIQUE OAKS CIR #39, WINTER PARK, FL 32792
$184,999509 Days on yellowkey MLS ID: OM695642
0 Days Off yellowkey (back on 6/26/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1105 Built: 1984Monthly Fee: $442 Tax: $2,702 (2024)Community: Parkview VillageCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,702
Elementary School: Aloma Elem
High School: Winter Park High
Tax Year: 2024
Middle School: Glenridge Middle
Remarks: PRICE REDUCED, Seller motivated. Condo in Winter Park, FL Welcome to 2923 Antique Oaks Cir, Unit 39 — a beautifully updated 1,105 sq. ft. first-floor condo offering 2 bedrooms, 2 bathrooms, and modern upgrades throughout. Located in the highly sought-after Winter Park School District, this property combines comfort, style, and convenience. Property Highlights: Size & Layout: Spacious 1,105 square feet with a thoughtfully designed floor plan. Updated Interiors: Recently remodeled with modern finishes, including appliances (convection oven, refrigerator, dishwasher), and washer/dryer in the interior laundry room. Outdoor Living: Relax on your private screened patio, perfect for morning coffee or evening unwinding. Community Features: Resort-Style Amenities: Enjoy a sparkling pool, a soothing hot tub, and meticulously maintained grounds. Pet-Friendly & Welcoming: Dog-friendly and community-oriented, providing a quiet and peaceful atmosphere. Prime Location: Zoned for A-rated Winter Park schools and just 2 miles away, this condo offers unmatched convenience: Walkable access to dining, shopping, and entertainment. Minutes from Park Avenue, Baldwin Park, Winter Park Hospital, and Downtown Orlando. Close to top educational institutions: Valencia College, Rollins College, Full Sail University, and UCF. With an HOA that provides excellent management and care, this is an incredible opportunity to own in a desirable and high-quality location.
Listing is courtesy of: GLOBALWIDE REALTY LLC (352-456-9788)
Listing Agent: Michell Carrasquero (305-850-2241)
700 MELROSE AVE #F 21, WINTER PARK, FL 32789
$235,90039 Days on yellowkey MLS ID: O6413612
1 Days Off yellowkey (back on 6/26/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 787 Built: 1964 Tax: $1,123 (2025)Community: Winter Park Gdns CondoCondo
Taxes:$1,123
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under contract-accepting backup offers. Click on virtual tour link. Floor-to-ceiling dazzling views, of sparkling pond, sweepiing oaks, towering cypress trees, and lush gardens — in the center of esteemed Winter Park. This beautifully updated upstairs unit sits within the serene Winter Park Gardens complex, where your views of the shimmering pond and pool anchor a lush sprawling landscape of live oaks draped in Spanish moss, mature manicured gardens, and lighted walkways- perfect for evening strolls. The unit itself has been thoughtfully renovated with brand-new luxury vinyl plank flooring, an open kitchen, updated granite countertops, and a fully renovated bathroom — all combining to deliver exceptional value in one of Central Florida's most coveted zip codes. This is a 55+ community with room for younger owners.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Olivia Maxwell (407-222-4440)
3037 ANTIQUE OAKS CIR #156, WINTER PARK, FL 32792
$154,90019 Days on yellowkey MLS ID: O6420008
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 749 Built: 1984 Tax: $2,058 (2025)Community: Parkview VillageCondo
Taxes:$2,058
Remarks: Cute as a button and move-in ready! This charming top floor 1-bedroom, 1-bath condo offers a bright, airy feel with an open-concept layout designed for comfortable living. Literally just steps away, you will enjoy peaceful views overlooking the hot tub and community pool from your private retreat above it all! The updated kitchen features beautiful white cabinetry with SOFT-CLOSE DRAWERS, providing both style and functionality. The spacious living area is enhanced by a vaulted ceiling that creates an expansive feel and allows natural light to pour in throughout the day. The primary bedroom continues the open, inviting atmosphere with vaulted ceilings and a generous walk-in closet. The bathroom offers a raised-height vanity with ample countertop space, making your daily routine both convenient and comfortable. This unit also comes with an INTERIOR LAUNDRY so you don’t have to worry about going off-site! Whether you’re relaxing at home on your SCREENED PATIO, enjoying the pool or hot tub, or taking in the view from your top floor location, this condo is the perfect blend of charm, comfort, and convenience. Come see it today!
Listing is courtesy of: VALENCE REALTY GROUP (407-797-5034)
Listing Agent: Chuck Valence (407-797-5034)
2500 LEE RD #208, WINTER PARK, FL 32789
$175,000459 Days on yellowkey MLS ID: O6297570
REDUCED by $5,000 (2.8%) on 05/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 956 Built: 1969Monthly Fee: $432 Tax: $1,519 (2025)Community: Lakeside Manor Apts CondoCondo
Taxes:$1,519
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfort and convenience. Featuring tile and luxury vinyl plank flooring throughout, this home provides durability and style for modern living. The HVAC was replaced in 2020 and water, cable and internet are included in the monthly COA fee. Located in a picturesque community ON THE SHORES OF A SKI LAKE, residents will enjoy access to boat slips (based on availability, charge is $30/month), a boat ramp, a sparkling pool, a welcoming clubhouse, and mature landscaping that enhances the serene environment. Outdoor enthusiasts will appreciate the multiple barbeque grills and tables, ideal for courtyard or lakeside dining. Additional amenities include two on-site laundry rooms, on-site storage, and convenient proximity to key destinations. COA approval is required. The application fee is $85.00. Situated in Winter Park, the community is less than 10 minutes from Winter Park Village, Maitland, and Downtown Winter Park, about 10 minutes from College Park, and approximately 15 minutes from Downtown Orlando and Lake Mary. This prime location ensures easy access to shopping, dining, entertainment, and the vibrant city lifestyle.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Debbie Jones (407-619-1850)
7484 CANFORD CT #8, WINTER PARK, FL 32792
$240,00078 Days on yellowkey MLS ID: O6402492
REDUCED by $10,000 (4.0%) on 06/22/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1578 Built: 1974 Tax: $2,121 (2025)Community: Whisperwood CondoCondo
Taxes:$2,121
Elementary School: Cheney Elem
Remarks: This three-bedroom, three-bath updated Winter Park townhome-style condo is located in a quiet complex, a perfect place to call home. It's just minutes away from the University of Central Florida, Full Sail University, & Valencia College. This location makes an excellent investment for a college (or parents of) student. The upgraded kitchen has granite countertops with a custom sink, newer stainless steel appliances, and a closet pantry. There is a separate dining room that opens onto a very private brick paver patio with a new privacy fence. This unique condo features a flexible layout, an inside utility, and includes the washer & dryer. Modern-design porcelain tile flooring. The home has a large screen porch, which is considered by many in Florida, to be extra living space. There is also a front courtyard that is perfect for a raised bed garden or ???. Highly desired Winter Park schools. A 2-car carport with an ample lockable storage closet. New roof in 2020 and an updated electric system. The complex has a private community pool
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Greg Harrison (407-276-6141)
300 CAROLINA AVE #402C, WINTER PARK, FL 32789
$750,00053 Days on yellowkey MLS ID: O6410016
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1350 Built: 1982 Tax: $2,416 (2025)Community: Park West CondominiumsSpa: NoCondo
Taxes:$2,416
Middle School: Audubon Park K-8
Remarks: Virtually Staged. Welcome to Park West Condominiums — one of Winter Park’s most coveted and rarely available condominium communities, ideally located just one block from the boutiques, dining, and charm of Park Avenue. This unique 4th floor residence offers an exceptional combination of space, privacy, and potential. Featuring 3 bedrooms and 2 bathrooms, the expansive floor plan has been enlarged by enclosing two patios, creating generous living spaces rarely found in condominium living. Vaulted ceilings, skylights, and abundant natural light enhance the open, airy feel throughout the home, while the top-floor location provides remarkable tranquility and privacy. The spacious kitchen offers ample counter space, a breakfast bar, and excellent cabinet space, while the living area is anchored by a fireplace — another uncommon feature in condo living. Large bedrooms, a sizable in-unit laundry room with extensive storage, and an oversized attic provide an extraordinary amount of storage seldom seen in comparable properties. The primary suite features vaulted ceilings, a walk-in closet, and a spacious bathroom layout. For maximum flexibility, the second bedroom, featuring a bright Sun Room alcove, connects to the primary bedroom so it could also be utilized as a private den. Recent unit improvements include a NEW HVAC system, a NEW Water Heater, and Plumbing updates. A reserved covered parking space is included, along with plentiful guest parking for visitors. Residents of Park West enjoy a secure gated entrance, community pool, tennis court, on-site community manager, and beautifully maintained grounds with extensive recent community improvements completed. Association fees include water, sewer, and trash service, creating a truly low-maintenance “lock-and-leave” lifestyle ideal for travelers or seasonal residents. While this condo presents an exciting opportunity for personalization, the location, floor plan, and features make this an exceptional offering with tremendous potential. Opportunities in Park West are exceedingly rare — this is your chance to create something truly special in the heart of Winter Park.
Listing Agent: Erin Baker (407-719-0030)
340 KILLARNEY BAY CT #4-4, WINTER PARK, FL 32789
$379,00060 Days on yellowkey MLS ID: O6407259
1 Days Off yellowkey (back on 6/22/2026)
REDUCED by $16,000 (4.1%) on 06/16/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1428 Built: 1986 Tax: $1,080 (2025)Community: Killarney Bay CondoCondo
Taxes:$1,080
Remarks: Under contract-accepting backup offers. Welcome to 340 Killarney Bay, a beautifully maintained residence located within one of Winter Park’s most charming and sought-after communities. With access to Lake Killarney, residents enjoy a waterfront community pool, dock, and a peaceful setting that perfectly complements the relaxed Winter Park lifestyle. This home offers a spacious and inviting layout with both bedrooms located upstairs for added privacy, as well as a balcony off one of the upstairs bedrooms. Recent updates include newer appliances, newer water heater (2022), and fresh interior paint downstairs and in bathrooms. Ideally located just minutes from Winter Park Village, Park Avenue, Trader Joe’s, top dining, shopping, and major roadways, this home delivers the perfect blend of convenience, lifestyle, and serene community living. Schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Blaike Gill (407-545-6430)
151 N ORLANDO AVE #259, WINTER PARK, FL 32789
$229,90054 Days on yellowkey MLS ID: O6409651
0 Days Off yellowkey (back on 6/21/2026)
REDUCED by $9,100 (3.8%) on 06/17/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 582 Built: 1960 Tax: $2,552 (2025)Community: Lake Killarney CondoCondo
Taxes:$2,552
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to Lake Killarney Living — where Winter Park charm meets everyday convenience. Discover this beautifully appointed condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, premier dining, boutique shopping, and the peaceful waters of Lake Killarney. This is low-maintenance, lock-and-leave living in one of Central Florida's most desirable lakefront communities. Inside, the condo is thoughtfully updated for modern comfort. A brand-new kitchen shines with sleek quartz countertops, while polished terrazzo floors flow throughout — a timeless, low-maintenance finish that's as durable as it is beautiful. Efficient mini-split air conditioning serves both the living room and bedroom, delivering precise, zoned cooling through even the warmest Florida summers, and a generous walk-in closet offers the kind of storage that's rare in condo living. Step outside to your private screened-in patio, the perfect spot for morning coffee, quiet evenings, or creating your own cozy outdoor retreat to unwind and enjoy the waterfront Florida sunset. Residents enjoy an impressive list of community amenities, including a sparkling private pool, a fitness center, lush green spaces, and beautifully maintained grounds. Best of all, the community offers optional private access to Lake Killarney, ideal for launching boats, kayaks, and paddleboards, fishing, or simply taking in serene lakefront views and some of Central Florida's most stunning sunsets. Enjoy evening sunset strolls, a weekend on the water, a relaxing afternoon by the pool, or sunsets around the firepit on the lake. Best of all boat slip is available for only $75 per month. With strong rental appeal, an unbeatable location, and timeless Winter Park charm, 151 N Orlando Ave #259 is an ideal choice for first-time buyers, downsizers, or investors seeking long-term value in a true lakefront community. month. Schedule your private showing today and experience the lifestyle waiting for you at Lake Killarney.
Listing is courtesy of: MAXLIFE REALTY LLC (321-373-3536)
Listing Agent: Ryan Solberg (407-748-3436)
1500 GAY RD #24B, WINTER PARK, FL 32789
$259,500287 Days on yellowkey MLS ID: O6348568
REDUCED by $2,000 (0.8%) on 05/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1026 Built: 1972 Tax: $1,271 (2024)Community: Chateaux Du LacSpa: NoCondo
Taxes:$1,271
Remarks: Under contract-accepting backup offers. ANOTHER PRICE REDUCTION! OWNER WILL CONSIDER ALL REASONABLE OFFERS! Highly Desirable Winter Park Lakefront Community on Skiable Lake Killarney. Enjoy Peaceful Water Views and Million-Dollar Sunsets on Lakefront Deck! Private Community Ramp, Heated Pool, Men's and Women's Saunas! Don't miss this! Beautifully Renovated 2 Bedroom 2 Bath End Unit. New Kitchen Cabinets and Quartz Counters, Stainless Steel Appliances, Raised Ceiling with Lighting, Kitchen Island/Bar! Enjoy the Ease of Luxury Vinyl Plank Flooring, Crown and Wide Floor Moldings, Plantation Shutters, Upgraded Energy Saving Windows and Sliding Glass Door. Modernized Master Bath with Raised Vanity, Open Layout with Spacious Shower with Seat and Barn Door for Privacy. Guest Bath also Updated with New Raised Vanity and Shower. Second Bedroom Walk-in Organized Closet. New Master Bedroom Carpet in 2025, New Water Heater in 8/2025 A/C replaced 4-5 years ago. Sit on Private Covered Patio and enjoy Pool Views and Landscaped Vistas. Walk to Shopping, Restaurants, Movies, Trader Joe's. Minutes from Park Avenue and Farmer's Market. Centrally located, close to I-4. One of Winter Park's "Best Kept Secrets"! Make an Appointment to view today!
Listing is courtesy of: REALCOM REAL ESTATE SERVICES INC (407-621-6856)
Listing Agent: Janice Erickson (407-621-6856)
151 NORTH ORLANDO AVENUE #142, WINTER PARK, FL 32789
$199,90034 Days on yellowkey MLS ID: O6412768
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 582 Built: 1960Monthly Fee: $398 Tax: $2,017 (2025)Community: Lake Killarney Condominium Assn Inc.Condo
Taxes:$2,017
Remarks: **Lakeside Living Meets Urban Convenience in the Heart of Winter Park!** Welcome home to this beautifully updated, turn-key 1-bedroom, 1-bathroom first-floor condominium located in the highly desirable Lake Killarney Condominiums community. Offering the perfect blend of modern interior updates, stress-free maintenance, and an unbeatable location, this unit is an absolute gem for first-time buyers, downsizers, or savvy investors looking to capture the ultimate Winter Park lifestyle. Step inside to an open, inviting living space featuring brand-new, modern Luxury Vinyl Plank (LVP) flooring running seamlessly throughout for a sophisticated look and maximum durability. The kitchen is freshly upgraded with brand-new, gleaming appliances and plenty of counter space. As a coveted first-floor unit, you will enjoy the ultimate convenience of easy, stair-free access, dual private entry points, and a private, screened-in patio perfect for sipping your morning coffee or winding down. One of the standout features of this property is its accessibility. **Great news for buyers shopping with FHA financing: the community is under the limit for single-unit approvals, making this an incredible opportunity to purchase with an FHA loan.** Additionally, the fairly low monthly HOA fee covers water, sewer, trash, pest control, and exterior/grounds maintenance. As a resident of Lake Killarney Condominiums, you will enjoy premium lakeside community amenities: **Sparkling Lakeside Pool** with stunning views over the water. **Private Community Boat Dock & Boat Ramp Access**, ideal for paddleboarding or sunset strolls. **On-site Fitness Room & Laundry Facilities** located steps from your door. **Clubhouse, Shuffleboard Courts, and Picnic Areas** with grills for effortless entertaining. Location is everything, and this address boasts an incredible walkability factor. You are quite literally around the corner from some of Central Florida’s finest dining, shopping, and entertainment: **Walk to Grocery & Dining:** Step next door or take a quick stroll to Trader Joe’s, the iconic Hillstone Restaurant overlooking the lake, and the completely revitalized Winter Park Village, which features a luxury movie theater, boutique shopping, and endless cafes. **Park Avenue District:** Just minutes away is Park Avenue, Winter Park’s historic cobblestone main street, renowned for its upscale boutiques, award-winning sidewalk dining, local art galleries, and the Saturday Farmers Market. **Commuter’s Dream:** The property offers lightning-fast access to Interstate 4 (I-4), putting downtown Orlando, Maitland Center, and major employment hubs just minutes away. The Winter Park SunRail Station is also less than a mile down the road for a stress-free commute. Don't miss out on this rare opportunity to own a fully updated, low-maintenance slice of paradise in one of Winter Park's most vibrant, lakeside neighborhoods. Schedule your private showing today!
Listing is courtesy of: CREEGAN GROUP (407-622-1111)
Listing Agent: Chris Creegan (407-622-1111)
256 LEWFIELD CIR #256, WINTER PARK, FL 32792
$184,900184 Days on yellowkey MLS ID: O6367842
1 Days Off yellowkey (back on 6/19/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 927 Built: 1973Monthly Fee: $465 Tax: $1,916 (2025)Community: Stratford A Winter Park CondoCondo
Taxes:$1,916
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: This charming and well-maintained 2 bedroom, second-floor condo in Winter Park is ready for you to call your own! The home features comfortable carpeted living areas throughout. The centrally located galley kitchen offers plenty of cabinet and counter space and connects directly to the dining room. The spacious living room gets plenty of natural light through large sliding glass doors, opening to a covered and screened rear porch with a pool view. The primary suite features a walk-in closet and a private bath with a floor-to-ceiling tiled walk-in shower. The HOA completed roofing and plumbing improvements in 2019, and all exterior and grounds maintenance is handled by the on-site HOA. The Stratford community offers two pools, a community and fitness center, and tennis courts. Just minutes from popular Downtown Winter Park with its dining and shopping, with easy highway access via the 417 and I-4, and surrounded by nearby lakes and parks, this is one opportunity you don’t want to miss. Call today to schedule your private tour!
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Renee Kumar Llc (407-756-4422)
200 SAINT ANDREWS BLVD #312, WINTER PARK, FL 32792
$170,000118 Days on yellowkey MLS ID: S5145794
3 Days Off yellowkey (back on 6/19/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 793 Built: 1970Monthly Fee: $451 Tax: $2,396 (2025)Community: Four Seasons CondoCondo
Taxes:$2,396
Elementary School: Brookshire Elem
Remarks: Beautifully maintained condo in a prime Winter Park location! This bright and inviting unit has been exceptionally well cared for and shows true pride of ownership. The interior is spotless, featuring a clean, modern feel with comfortable living spaces that make it easy to feel right at home. Enjoy a well-designed layout with plenty of natural light and a welcoming atmosphere throughout. The kitchen and living areas flow nicely, creating a great space for both everyday living and relaxing. Every part of the home has been kept in excellent condition, making it move-in ready for its next owner. Conveniently located near shopping, dining, major roadways, nearby parks and major roadways. A great opportunity for an investment in a desirable area. Schedule your showing today!
Listing is courtesy of: ROMAN'S PRO REALTY LLC (407-610-1970)
Listing Agent: Reinaldo Roman (321-682-1124)
630 KILLARNEY BAY CT #3, WINTER PARK, FL 32789
$475,000166 Days on yellowkey MLS ID: O6375307
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1428 Built: 1986 Tax: $6,595 (2025)Community: Killarney Bay CondoCondo
Taxes:$6,595
Remarks: Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedrooms, 2.5 baths, and a one-car carport. This spacious residence features an open living and dining area that flows to a screened porch, perfect for relaxing and enjoying tranquil lake views in a well-maintained complex. Both bedrooms are upstairs for privacy, each with its own bath. A convenient half bath is on the main level for guests. Enjoy community amenities including a swimming pool and a waterfront deck just 30 feet away, ideal for soaking in sunsets and lakeside breezes. All of this in an unbeatable location, just minutes from Winter Park Village, Trader Joe’s, Whole Foods, Park Avenue, dining, and shopping, with easy access to major roads for commuting.
Listing is courtesy of: FLORIDA ONE REAL ESTATE LLC (407-599-7070)
Listing Agent: Anthony Consalvo (407-599-7070)
3243 FOREST OAKS COURT #117, WINTER PARK, FL 32792
$172,00066 Days on yellowkey MLS ID: O6406448
REDUCED by $3,000 (1.7%) on 06/19/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 990 Built: 1983 Tax: $2,723 (2025)Community: Hidden Oaks Condo Ph 7Spa: NoCondo
Taxes:$2,723
Remarks: Welcome to this beautifully maintained 2-bedroom, 1.5-bathroom townhouse-style condominium located in the desirable Hidden Oaks Condominium community. This charming unit features a spacious living and dining area with tile flooring throughout the first floor, along with a well-appointed kitchen, breakfast nook, and convenient indoor laundry room. The home has been freshly updated with new interior paint and new blinds throughout, and all appliances are included for added convenience. Step through the sliding glass doors off the kitchen to enjoy a private fenced patio, complete with an additional exterior storage room — perfect for extra storage space or outdoor essentials. Upstairs, you’ll find comfortable carpet flooring throughout, including a generously sized primary bedroom with a large closet, as well as a spacious guest bedroom with ample closet space. Residents of Hidden Oaks Condominium enjoy access to excellent community amenities, including a sparkling community pool and a fenced playground area. The monthly HOA fee includes water and trash services. Ideally located near Full Sail University, University of Central Florida, and Valencia College, with convenient access to shopping, dining, Downtown Orlando, Downtown Winter Park, FL-408, and FL-417. This move-in ready home offers comfort, convenience, and an excellent location. Schedule your private showing today — this opportunity won’t last long!
Listing is courtesy of: SOGO REAL ESTATE SERVICES LLC (407-730-3100)
Listing Agent: Jessie Lin, Llc (631-672-9511)
1500 GAY RD #20D, WINTER PARK, FL 32789
$258,000139 Days on yellowkey MLS ID: O6385626
REDUCED by $4,000 (1.5%) on 06/07/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1026 Built: 1972 Tax: $3,283 (2024)Community: Chat6eaux Du LacSpa: NoCondo
Taxes:$3,283
Remarks: LAKEFRONT COMMUNITY WITH SPECTACULAR SUNSETS OVER BEAUTIFUL LAKE KILLARNEY. LOCATED IN THE CHARMING AND ELLEGANT NEIGHBORHOOD OF WINTER PARK, IN A FULLY REVITALIZED AREA. CONVENIENT TO I-4, PARK AVENUE, FARMER'S MARKETS, TRADER JOE'S, AS WELL AS A MOVIE THEATER, BOUTIQUE SHOPS, RENOWNED RESTAURANTS AND A NATIONALLY RATED ART FESTIVAL - ALL WITHIN A SHORT WALKING DISTANCE. BRIGHT SUN-FILLED 2 BEDROOM, 2 BATH USTAIRS UNIT WITH AN OPEN FLOOR PLAN AND PRIVATE BALCONY. THE PRIMARY BEDROOM IS A SUITE, AND THE SECOND BEDROOM FEATURES A SPACIOUS WALK-IN CLOSET. SOFT, WARM COLORS, TILE AND LUXURY VINYL FLOORS, RAISED KITCHEN CEILING AND GRANITE COUNTER ENHANCE THE SPACE. BRAND NEW WATER HEATER 6/2026! LARGE ROOMS MAKE IT EASY TO ARRANGE FURNITURE. ENJOY BOATING, SKIING AND WILDLIFE OF LAKE LIVING. COMMUNITY DECK, BOAT RAMP, HEATED POOL AND SAUNAS. MAKE AN APPOINTMENT TODAY TO SEE WINTER PARK'S BEST KEP SECRET!
140 E MORSE BLVD #J, WINTER PARK, FL 32789
$2,350,00027 Days on yellowkey MLS ID: O6414891
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2143 Built: 2008 Tax: $18,655 (2025)Community: Landmark Winter Park CondoCondo
Taxes:$18,655
Elementary School: Audubon Park K8
Remarks: Discover an exceptional opportunity to own a penthouse residence at The Landmark, one of downtown Winter Park's exclusive addresses. Directly along the desired brick streets of Park Avenue, this boutique condominium community consists of only 13 residences and offers an unparalleled blend of privacy, sophistication and accessible convenience. Just outside your door, enjoy acclaimed dining, boutique shopping, art galleries, sidewalk cafés, Central Park and the year-round events that have made Winter Park one of Central Florida's sought-after destinations. Behind The Landmark's secure wrought-iron gates, residents are welcomed into a beautifully landscaped courtyard centered around a timeless fountain and illuminated by dozens of gas lanterns, creating a warm and elegant atmosphere reminiscent of a European enclave. Impeccably maintained and thoughtfully designed, the community provides a peaceful retreat while remaining moments from the vibrant energy of Park Avenue. Residence J occupies a premier penthouse position and is filled with natural light, enhanced by soaring ceilings, expansive windows, and multiple French doors that open to private terraces overlooking Morse Boulevard and the surrounding downtown streetscape. The spacious floor plan is designed for comfortable daily living and effortless entertaining. The living and dining areas are anchored by a gas fireplace and flow seamlessly into the kitchen, where integrated appliances, a gas cooktop, generous workspace, and a charming breakfast area create a functional and inviting gathering space. The primary suite serves as a private sanctuary, featuring dual vanities, separate water closets, an oversized walk-in shower and a custom-designed walk-in closet. Two additional guest bedrooms provide flexibility for family and visitors. One bedroom is connected to a Jack-and-Jill bath, while the third enjoys a private en-suite bath and a Juliet balcony that captures the charm and character of downtown Winter Park from above. Additional amenities include two deeded underground parking spaces, a private climate-controlled storage room, and access to the community's shared outdoor entertaining area, complete with a summer kitchen and courtyard gathering space. Whether enjoyed as a full-time residence or a lock-and-leave retreat, this penthouse offers a rare combination of luxury, security and an unmatched Park Avenue lifestyle in the heart of Winter Park.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Mick Night (407-629-4446)
1695 LEE RD #E215, WINTER PARK, FL 32789
$135,000147 Days on yellowkey MLS ID: O6383089
REDUCED by $14,990 (10.0%) on 06/17/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1149 Built: 1966Monthly Fee: $624 Tax: $2,472 (2024)Community: Waterfall CoveCondo
Taxes:$2,472
Elementary School: Hungerford Elem
Remarks: Located in the heart of Winter Park, this charming condo stands ready to welcome you home. This three-bedroom, two-bathroom sanctuary offers a blend of comfort and modern elegance, perfect for those who cherish both relaxation and entertaining. As you step inside, the spacious living and dining areas greet you with an abundance of natural light, creating a warm and inviting atmosphere. Imagine hosting friends and family in this expansive space, where laughter and memories will fill every corner. The heart of this home is undoubtedly the fully upgraded kitchen, featuring stunning quartz countertops, sleek new cabinets, and stainless steel appliances. Each meal becomes a culinary adventure in this thoughtfully designed area. Retreat to any of the large bedrooms, designed to be your personal oasis. Each room offers generous space, allowing for restful nights and peaceful mornings. A dedicated laundry room, complete with a washer and dryer, adds convenience to your daily routine, while ample storage throughout the unit ensures that everything has its place. Step outside onto your private balcony, where a serene courtyard unfolds below. Picture yourself sipping morning coffee or enjoying an evening breeze as you overlook the tranquil scene of benches, a sparkling pool, and a welcoming clubhouse—perfect for gathering with neighbors or unwinding after a busy day. This pet-friendly community understands that your fur babies deserve a home too, so bring them along for this new adventure! Plus, enjoy the benefits of the HOA, which includes cable TV and high-speed internet, making it easy to stay connected. With a prime location just a short walk from a variety of shopping and dining options, you’ll find everything you need right at your fingertips. And with quick access to I-4, the beautiful beaches and thrilling theme parks are just minutes away. This isn't just a condo; it’s a lifestyle filled with comfort, convenience, and community. Welcome to your new home in Winter Park! Schedule your private tour today.
Listing is courtesy of: FOWLKES REALTY CO (407-361-2052)
Listing Agent: Jenaia Fowlkes (407-361-2052)
2500 LEE RD #220, WINTER PARK, FL 32789
$199,90036 Days on yellowkey MLS ID: O6411927
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 851 Built: 1969Monthly Fee: $292 Tax: $2,015 (2025)Community: Lakeside Manor Apts CondoCondo
Taxes:$2,015
Remarks: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 2500 Lee Road, Unit 220, in Winter Park, a beautifully maintained condominium offering stylish, low-maintenance living in one of Central Florida's most convenient locations. Inside, the condo features 2 bedrooms and 1 bathroom with a functional layout suited for everyday living. Thoughtfully updated throughout, this unit features a modern kitchen with stainless steel appliances, charcoal quartz countertops, and a spacious island with ample storage. The bathroom has also been updated with contemporary finishes, while the unit's clean, modern design creates an inviting atmosphere throughout. A new A/C installed in 2025 provides added comfort and peace of mind. The floorplan includes comfortable living and dining areas, while the secondary bedroom offers flexibility for guests, a home office, or additional storage. The unit overlooks a beautifully landscaped courtyard and is conveniently located near designated parking. Residents enjoy access to a variety of community amenities, including a clubhouse, pool, laundry facilities, park areas, and dock access on Lake Killarney. The lakefront setting provides a peaceful environment and an opportunity to enjoy the surrounding natural beauty. Located in the heart of Winter Park, the condo is close to shopping, dining, parks, and popular destinations such as Winter Park Village, Park Avenue, College Park, Maitland, and Downtown Orlando. With its desirable community amenities and prime Winter Park location, this move-in-ready condo offers exceptional value and convenience.
Listing Agent: Thomas Nickley, Jr (407-629-4420)
639 SAINT JOHNS CT #639, WINTER PARK, FL 32792
$194,90079 Days on yellowkey MLS ID: O6402025
REDUCED by $5,000 (2.5%) on 06/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1120 Built: 1981 Tax: $3,077 (2025)Community: Winter Park VillasCondo
Taxes:$3,077
Remarks: Freshly painted 2 Bedroom/2 Bath townhouse-style condo with no neighbors above or below, backing up to a peaceful pond & community amenities. The upstairs/downstairs split-bedroom floor plan offers privacy - ideal for roommates or families. The bright living area features soaring cathedral ceilings, a corner fireplace, and access to a partially covered patio, perfect for entertaining or BBQs. There's abundant storage throughout, including coat, linen, patio, and under-stair space that could be converted into a small office or workout nook. The kitchen comes fully equipped with all appliances, ample cabinet space, and a breakfast bar, while the dining area overlooks the pond and opens to the patio with an additional storage closet. Upstairs, the primary suite includes an en-suite bath, a large walk-in closet, and corner windows that brings in great natural light. The second bedroom is located downstairs and offers dual closets and a ceiling fan. Updated luxury vinyl flooring runs through most of the home, and there is also an in-unit washer/dryer for convenience. Located in the highly desirable Winter Park Villas community, residents enjoy a wide array of amenities including a sparkling pool, clubhouse with fitness center, tennis courts, car wash station, scenic ponds, pet stations. The HOA provides exceptional value by covering roof & exterior maintenance, lawn service, water, trash, sewer, pest control—ensuring truly low-maintenance living. Conveniently located just minutes from Full Sail University, Rollins & Valencia Colleges, approximately 10 minutes from downtown Winter Park. Top-rated schools nearby, this property is an excellent opportunity for both homeowners & investors. Outdoor enthusiasts will also appreciate easy access to the nearby Cady Way Trail, perfect for walking, jogging, or cycling.
Listing is courtesy of: PLATINUM REALTY GROUP FLORIDA INC (407-270-7378)
Listing Agent: Adam Eisen (407-808-6967)
300 CAROLINA AVE #301, WINTER PARK, FL 32789
$739,00040 Days on yellowkey MLS ID: O6413279
0 Days Off yellowkey (back on 6/13/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1305 Built: 1981 Tax: $4,605 (2025)Community: Park West CondoCondo
Taxes:$4,605
Remarks: Under contract-accepting backup offers. Enjoy the best of living in this beautifully renovated well maintained 2-bedroom, 2-bath condominium located in the highly desirable gated Park West Condominiums. Perfectly positioned just steps from the renowned Park Avenue, this exceptional residence offers walking distance access to award-winning restaurants, charming boutiques, sidewalk cafés, and the popular weekly farmer’s market. This rare 3rd-floor corner unit which enhances privacy was completely remodeled in 2019 with quality upgrades throughout. The interior features are engineered wood flooring, updated tile, modern ceiling lighting, and a bright open-concept floor plan filled with natural light from expansive sliding glass doors leading to three private walk-out balconies. The redesigned kitchen in 2019 includes new cabinetry, countertops, a complete suite of kitchen appliances, including washer and dryer. Both bathrooms have also been tastefully renovated, creating a clean and contemporary feel throughout the home. Additional improvements include a brand-new HVAC system installed in July 2024, offering peace of mind and energy efficiency for years to come. Spacious bedrooms, generous storage, and seamless indoor-outdoor living make this condo ideal for both everyday living and entertaining. Park West residents enjoy beautifully maintained grounds along with community amenities including a sparkling swimming pool and tennis courts. The community is also conveniently located to Rollins College and Full Sail College. Whether you are searching for a full-time residence or seasonal retreat, this exceptional condo combines timeless Winter Park charm with modern updates and an unbeatable location.
Listing Agent: Kevin Mcclanahan (407-491-8509)
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