Location: Winter Park
Do Not Show Listings
1500 GAY RD #24B, WINTER PARK, FL 32789
$261,500206 Days on yellowkey MLS ID: O6348568
REDUCED by $2,500 (0.9%) on 04/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1026 Built: 1972 Tax: $1,271 (2024)Community: Chateaux Du LacSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,271
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: 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)
144 LEWFIELD CIR #144, WINTER PARK, FL 32792
$137,00043 Days on yellowkey MLS ID: O6390043
REDUCED by $7,000 (4.9%) on 04/21/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 678 Built: 1973Monthly Fee: $351 Tax: $720 (2024)Community: Stratford A Winter Park CondoCondo
Taxes:$720
Remarks: LOCATION! LOCATION! LOCATION! Beautiful 2nd floor corner condo in desirable Winter Park, featuring 1 bed/1 bath, open concept living/dining area and balcony. Move-in ready and conveniently located near UCF, Rollins College, Valencia College, Park Avenue, and Downtown Orlando. Residents enjoy resort-style amenities including two pools, tennis court, a fitness center, and clubhouse available for rental for gathering or events. The unit includes a fully equipped kitchen, stackable washer and dryer in the bedroom, and access to free community laundry. HOA covers water, trash removal, internet, pest control, exterior maintenance, and grounds care. Close to shopping, dining, and major highways for easy access across the area.
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: Sandra Da Silva (407-840-8500)
2401 SUN VALLEY CIR #2401, WINTER PARK, FL 32792
$265,00030 Days on yellowkey MLS ID: S5146437
REDUCED by $20,000 (7.0%) on 04/21/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1495 Built: 1984 Tax: $3,702 (2024)Community: Cedarwood Village 1Condo
Taxes:$3,702
Remarks: Welcome to this charming 2-bedroom, 2-bath condo with a versatile loft, perfectly situated just minutes from shopping and the vibrant downtown Winter Park area! This light-filled end unit offers an open floor plan with vaulted ceilings and skylights, creating a bright and airy feel throughout. You’ll appreciate the newer flooring, crown molding, and the comfortable, functional layout. Relax and unwind on the private back porch—an ideal outdoor sitting space. The kitchen features a pantry and cozy breakfast nook. The spacious primary suite includes a walk-in closet, updated bathroom, and direct access to the back patio. The second bedroom also offers new flooring and its own walk-in closet, making it perfect for guests or additional living space. With its inviting design and unbeatable location, this condo is a must-see—schedule your private showing today!
Listing is courtesy of: EXP REALTY LLC (407-846-0940)
Listing Agent: Jamie Bollinger (407-908-1890)
2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792
$269,0004 Days on yellowkey MLS ID: O6400674
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1295 Built: 1985Monthly Fee: $499 Tax: $2,560 (2024)Community: Cedarwood Village 1Condo
Taxes:$2,560
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Nestled in a peaceful setting within the serene Cedarwood Village community, this charming one-story Winter Park condo offers a quiet retreat away from traffic noise, with a rear wooden fence for no visible neighbors for added privacy. The spacious 27-foot tiled and enclosed lanai creates the perfect place to relax and enjoy the tranquil surroundings. Cedarwood Village also offers low-maintenance living, with lawn care included in the HOA, along with amenities such as rebuilt tennis courts, a recently remodeled pool, a clubhouse, dog-walking areas, and newly paved roads. Conveniently located in a highly rated school district and close to shopping, dining, and entertainment, the property is also just minutes from Full Sail University, Valencia College, and UCF. Inside, the condo is beautifully updated and shows the care of meticulous owners. The modern kitchen features granite countertops, matching cabinetry, and an eat-in area with sliding doors leading to the private patio, while the bathrooms and dining room wet bar are finished with the same stylish cabinets and granite. The split floor plan includes tile flooring throughout the main living areas and wood floors in the bedrooms. The large living and dining spaces feature vaulted ceilings with skylights for abundant natural light, along with a cozy wood-burning fireplace. French doors from the living room open to the enclosed lanai, while the primary suite also has direct lanai access, ample closet space, and a private bath with both a tub and shower. Additional features include an interior laundry closet adjacent to the kitchen, updated plumbing, a roof replaced in 2018, new ductwork installed in 2023, and a $4,500 seller credit at closing toward a new AC. Two assigned parking spaces are located directly in front of the unit. Tenants will be moving out May 31, 2026.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PROPERTIES (407-644-5385)
Listing Agent: Jeff Stewart (407-247-9762)
200 SAINT ANDREWS BLVD #2901, WINTER PARK, FL 32792
$225,00022 Days on yellowkey MLS ID: O6395720
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1266 Built: 1970Monthly Fee: $451 Tax: $2,131 (2025)Community: Four Seasons CondoCondo
Taxes:$2,131
Elementary School: Brookshire Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Glenridge Middle
Remarks: Welcome to this spacious and well-maintained 2 story townhome in the heart of Winter Park, located in the highly sought-after Four Seasons community. This 2-bedroom, 1.5-bath unit offers 1,266 square feet of comfortable living space with a functional layout, abundant natural light, and thoughtful updates throughout. Step inside to find a spacious kitchen, renovated in 2016, featuring wood cabinetry, granite countertops, black appliances, and a dishwasher replaced in 2023, perfect for everyday cooking and entertaining. Just off the kitchen, enjoy a dedicated dining area, ideal for hosting dinners or creating a flexible space for a home office or additional seating. The inviting living room provides plenty of space to relax and gather, with sliding glass doors that lead to your private, fully fenced, tree-shaded patio complete with a storage shed - an ideal spot to enjoy your morning coffee or unwind in the evenings. The patio also offers convenient access to your covered, deeded carport space, #49. Both bedrooms are generously sized, with the primary bedroom featuring dual closets and a ceiling fan for added comfort. The home includes a full bathroom and a convenient half bath, both thoughtfully updated with new toilets and upgraded vanities, including a quartz countertop and stylish shiplap accent in the guest bath. Additional interior highlights include custom closet features, a laundry closet with a new stackable washer and dryer(included), ceiling fans and blinds throughout, fresh interior paint (2024), and an HVAC system updated in 2023, providing peace of mind and modern convenience. Residents of Four Seasons enjoy access to a variety of amenities including 3 swimming pools, a clubhouse with fitness center, tennis and shuffleboard courts, all within a quaint, established neighborhood with tree-lined walkways. Ideally located just minutes from Ward Park, Winter Park Pines Golf Club, YMCA, AdventHealth Winter Park, and the Center for Health & Wellbeing. Enjoy easy access to shopping and dining along Aloma Avenue including Publix, Sprouts, and Aldi, as well as being less than 10 minutes from Park Avenue’s renowned restaurants and boutiques. Conveniently located near SR 436 with quick access to 417 and 408, and approximately 25 minutes to Orlando International Airport. Zoned for top-rated schools: Brookshire Elementary, Glenridge Middle, and Winter Park High School. Don’t miss your opportunity to own in one of Winter Park’s most desirable communities—schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Amy Turner (407-803-3885)
2501 TAHOE CIR, WINTER PARK, FL 32792
$259,90085 Days on yellowkey MLS ID: O6378209
2 Days Off yellowkey (back on 4/21/2026)
REDUCED by $10,000 (3.7%) on 04/05/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1495 Built: 1981 Tax: $3,757 (2025)Community: Cedarwood Village 1Condo
Taxes:$3,757
Remarks: Under contract-accepting backup offers. Recently Improved to $259,900 - One of the BEST Values in Winter Park !! Welcome home to this spacious two-story Winter Park condo located in the sought-after Cedarwood Village community. Tucked away among mature landscaping yet close to everything, this residence offers a comfortable blend of privacy, architectural character, and convenience in a prime Central Florida location. The main living area features soaring 16.5-foot vaulted ceilings, a wood-burning fireplace, and sliding glass doors that lead to a screened rear porch, creating a seamless indoor-outdoor connection. Two skylights and a second-story loft overlooking the living room add architectural interest and flexible space ideal for a home office, reading nook, or guest retreat. The thoughtfully designed split floor plan enhances functionality and privacy. Additional highlights include a spacious kitchen with breakfast bar and island, a primary suite on the main level, and a screened back porch perfect for relaxing or entertaining. Community amenities include a swimming pool and tennis courts, supporting a low-maintenance, active lifestyle. Located just minutes from Rollins College, with convenient access to local retail shopping, dining, and everyday conveniences, this home is also a short drive to downtown Orlando, offering easy access to museums, theaters, and a variety of local events—combining the charm of Winter Park with excellent city connectivity. All measurements and information should be verified.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Sarah Doyer (386-490-7677)
7301 CEDAR CREEK CT #66, WINTER PARK, FL 32792
$187,50015 Days on yellowkey MLS ID: O6397477
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1031 Built: 1983Monthly Fee: $10 Tax: $2,731 (2025)Community: Hidden Oaks Condo Ph 04Condo
Taxes:$2,731
Remarks: Welcome home to this beautiful starter home or perfect student housing in Winter Park! Two story townhouse style condo with 2 bedrooms each with private full ensuite bathroom and an extra half bath on the main floor. Renovated with stone counters and all luxury plank flooring- no carpet! New appliances and a nice open kitchen with breakfast bar- very unusual in this development. Washer and dryer in unit. Private fenced back patio with outdoor storage and small front garden for your green thumb. Only 15 min to UCF, 5 min to Full Sail and near all major shopping and dining including COSTCO, Target, Publix and more. Winter Park schools.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
3028 GEORGE MASON AVE #J-7E, WINTER PARK, FL 32792
$105,0009 Days on yellowkey MLS ID: O6398380
0 Days Off yellowkey (back on 4/20/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1088 Built: 1974Monthly Fee: $427 Tax: $1,989 (2025)Community: ColoniesCondo
Taxes:$1,989
Remarks: Priced to sell and move-in ready TODAY. This completely updated 2-bedroom, 2-bathroom, 1,088 sq ft ground-floor condo in the heart of Winter Park is the opportunity buyers and investors have been waiting for. At $105,000 (special assesment to-be-paid by buyer) in the 32792 zip code, it will not last. Step inside to brand-new marble-look porcelain tile flowing through every room, no carpet anywhere. The modern gray paint palette gives the entire unit a clean, contemporary feel. The kitchen features stainless steel appliances including a glass-top range, built-in microwave, refrigerator, and dishwasher, plus bright cabinetry and dark countertops. The spacious master bedroom includes a ceiling fan and sliding glass doors that open to a private patio. The second bedroom boasts a charming bay window that floods the room with natural light, ideal as a guest room or home office. Both bedrooms include generous closet space. Two full bathrooms, each with a walk-in shower and updated fixtures. In-unit stacked washer and dryer included, no shared laundry, no trips outside. Sliding glass doors from the living area open to your own ground-floor patio for true indoor-outdoor Florida living. The community features a resort-style pool, hot tub, and covered pavilion just steps from your front door. Minutes from Park Avenue, Rollins College, Winter Park Village, the SunRail station, and easy access to I-4 and 417. First-time buyer, investor, or snowbird, this is your move. Turnkey, updated, and priced below market. Schedule your showing today or buy with confidence sight unseen.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Alex Cheikh-Khalil (407-849-8967)
1809 HAMMERLIN AVE, WINTER PARK, FL 32789
$585,000100 Days on yellowkey MLS ID: O6373616
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1818 Built: 2006 Tax: $5,826 (2024)Community: Terazzo Del Sol Condo Assn IncCondo
Taxes:$5,826
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: Highly coveted Winter Park! 40+ Pictures! This stunning 2-story end unit offers the epitome of modern convenience and elegant living; this residence provides the ideal "lock and go" lifestyle. Step through the charming covered front porch into the inviting open living area, adorned with abundant natural light, gleaming real wood flooring, and exquisite crown molding. Hosting gatherings is effortless in the expansive kitchen featuring granite countertops, premium wood cabinetry, stainless steel appliances, and a generously sized pantry. A half bathroom and utility closet complete the ground floor, where ceilings soar to a height of 9'3". Ascend to the upper level to discover the luxurious master bedroom suite, boasting French doors leading to a balcony, a spacious walk-in closet, and a lavish ensuite bath featuring dual sinks, a glass-enclosed shower, and a relaxing garden tub. Two additional bedrooms await upstairs, both sharing access to a covered porch perfect for savoring your morning coffee. The second full bathroom and laundry closet round out the upstairs layout, with one of the bedrooms boasting its own walk-in closet. New 2026 Updates to include New Roof Feb 2026, Carpet, New main DBL pane windows, complete interior paint, light fixtures/fans. You will appreciate the convenience of an attached 2-car garage designed for SUVs, two covered entries, adorned with mature trees. Solid build quality utilizing concrete block construction on both floors. Located just a short stroll from the vibrant East End Market and various shopping, this residence also offers easy access to upscale Park Avenue, Rollins College, Baldwin Park, Florida Hospital, and the serene beauty of Leu Gardens. Zoned for Audubon and Winter Park HS, this home truly has it all!
Listing is courtesy of: NICOLE-HUDSON REALTY CORP (407-491-5488)
Listing Agent: Edward Rice, Jr (407-353-0331)
2500 LEE RD #208, WINTER PARK, FL 32789
$180,000378 Days on yellowkey MLS ID: O6297570
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)
188 LEWFIELD CIR #188, WINTER PARK, FL 32792
$129,99052 Days on yellowkey MLS ID: O6387291
REDUCED by $9,010 (6.5%) on 04/20/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 678 Built: 1973 Tax: $424 (2024)Community: Stratford A Winter Park CondoCondo
Taxes:$424
Remarks: Welcome to 188 Lewfield Cir — a beautifully designed 1-bedroom, 1-bath condo located in the highly desirable The Stratford at Winter Park Condominium community. This unit features an open floor plan that creates a bright, spacious feel, perfect for comfortable everyday living or entertaining guests. The layout maximizes functionality while maintaining a modern, low-maintenance lifestyle. Residents of The Stratford enjoy resort-style amenities including two outdoor swimming pools, a clubhouse, a fully equipped fitness center, and beautifully maintained grounds; offering both relaxation and convenience right outside your door. Located in the heart of Winter Park, you’re just minutes from premier shopping, top-rated restaurants, entertainment, and major roadways. Whether you're looking for a primary residence, seasonal retreat, or investment opportunity, this location places you in one of Central Florida’s most sought-after areas. Comfort. Convenience. Winter Park lifestyle. 188 Lewfield Cir is ready to welcome you home.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Johnny Aybar, Llc (407-808-9569)
2500 LEE RD #202, WINTER PARK, FL 32789
$234,999442 Days on yellowkey MLS ID: O6277579
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 956 Built: 1969Monthly Fee: $398 Tax: $2,327 (2025)Community: Lakeside Manor Condominium Association, Inc.Condo
Taxes:$2,327
Remarks: One or more photo(s) has been virtually staged. MILLIONAIRE LIFESTYLE HIDDEN GEM • LAKE ACCESS • 2 BED / 2 BATH CONDO ON LAKE KILLARNEY • PRIME WINTER PARK LOCATION • LOW HOA Outstanding Opportunity to enjoy the Florida Lifestyle in your private walkable Lakefront Enclave. Includes Direct Lake Access, Private Dock, Loungers and seating, Picnic areas and landscaping, Boat Slip, and a Private Pool & Clubhouse overlooking Lake Killarney. You will love Paddle Boarding, Kayaking and Boating just steps from your door. Beautifully updated 2-bedroom, 2-bathroom condo located on the shores of Lake Killarney in highly desirable Winter Park. This immaculate home offers tranquil lakeside living and unbeatable convenience, minutes from Trader Joe’s, Park Avenue, Rollins College, and Downtown Orlando. The condo is upgraded throughout with New AC & Water Heater, Fresh New Interior Paint, New Lighting, New Ceiling Fans & Window Blinds, Updated Door Hardware, Primary Bathroom Renovation featuring new tile, modern vanity, and LED mirror, Upgraded Exterior Doors & Windows. Open-concept kitchen with dark wood cabinetry, granite countertops, a built-in wine rack, and breakfast bar, flows into the spacious living area and private balcony. Enjoy two private patio spaces front and rear, overlooking the courtyard, perfect for relaxing and entertaining. With only one neighbor to the side and one below, this unit offers enhanced privacy. Split-Bedroom Design, Two large bedrooms, each with walk-in closets. Primary suite includes a private exterior entrance and a fully renovated bathroom with walk-in shower. Second bathroom includes a tub/shower combo and tile flooring. Enhance your life living minutes from Park Avenue (shopping, dining, events), Rollins College (3 miles), Winter Park Village, I4 for easy commuting, Downtown Orlando, Orlando International Airport, Disney, and Universal (20–30 mins). Low HOA Includes Water & Trash, Lake Access & Dock, Pool & Clubhouse, Designated Parking.
Listing is courtesy of: THE ANDERSON GROUP & CO PL (407-960-5657)
Listing Agent: Alison Maltby (407-325-1483)
3057 AARON BURR AVE #1, WINTER PARK, FL 32792
$116,000142 Days on yellowkey MLS ID: O6364189
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1066 Built: 1974Monthly Fee: $409 Tax: $1,911 (2024)Community: ColoniesCondo
Taxes:$1,911
Remarks: Back in market for Buyer finance .A great living in Winter Park. This 2-bedroom, 2-bath Furnished condo in The Colonies offers an excellent opportunity for investors or first-time buyers. Recently updated with new flooring and new painting the unit is ready for a new owner. The location is a major draw, just minutes from Full Sail University,Sam Wearhouse, Valencia College, UCF, Park Avenue, Downtown Orlando, and Orlando International Airport. With highly rated Winter Park schools, and shopping, dining, and cultural attractions nearby,. A rare chance to own in Winter Park at a great price, this condo combines strong value with a prime location.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Amin Abraham (407-230-0803)
2317 SUN VALLEY CIR #2317, WINTER PARK, FL 32792
$279,0007 Days on yellowkey MLS ID: O6398500
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1295 Built: 1987 Tax: $1,107 (2025)Community: Cedarwood Village 1Condo
Taxes:$1,107
Remarks: Discover comfort and convenience in this charming, spacious 2-bedroom, 2-bath residence nestled in the heart of Winter Park! Step inside to an inviting living room with a vaulted ceiling. The fully equipped open-floor kitchen, featuring ample roomy cabinets, is perfect for everyday living and entertaining. The thoughtfully designed split floor plan enhances functionality and privacy. Elegant, durable flooring throughout the home ensures easy maintenance. Enjoy the walk-in shower and bathtub with upgraded plumbing and tile. A convenient coffee nook sits just off the kitchen. The spacious patio is ideal for entertaining guests and enjoying outdoor time. Community amenities include a swimming pool and tennis courts, supporting a low-maintenance, active lifestyle.
Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)
Listing Agent: Robert Arnold, Jr (407-389-7318)
5143 LAZY OAKS DR #5143, WINTER PARK, FL 32792
$285,00010 Days on yellowkey MLS ID: O6398856
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1008 Built: 1984 Tax: $668 (2024)Community: Lazy Oaks CondoCondo
Taxes:$668
Elementary School: Eastbrook Elementary
Remarks: Quiet Living in the Desirable Lazy Oaks Community of Winter Park. Welcome to the peaceful, well-established community of Lazy Oaks in highly sought-after Winter Park. This hidden gem offers beautifully landscaped grounds, meticulous maintenance, and the added benefit of a low HOA. This lovingly maintained 2-bedroom, 2-bath home features a spacious, thoughtfully designed floor plan with an attached garage. The home is ideally located near top-rated schools, shopping, dining, and provides convenient access to major highways. Inside, you’ll find a neutral color palette complemented by ceramic tile and wood laminate flooring throughout. The efficient kitchen boasts gleaming white countertops, rich wood cabinetry, and a large pantry for ample storage. The expansive great room offers flexible space for both dining and living areas, complete with a cozy wood-burning fireplace—perfect for relaxing or entertaining. Sliding glass doors open to a large, screened private lanai, ideal for morning coffee or evening unwinding. The spacious primary suite features an en suite bath with dual sinks, a large vanity, walk-in shower, and a generous closet. A split-bedroom layout provides added privacy, with a secondary bedroom and additional full bath. Additional highlight: HVAC replaced in 2021. Don’t miss this opportunity to make your home in one of Winter Park’s most charming and convenient communities!
Listing Agent: Mindy Machock (407-461-1866)
300 CAROLINA AVE #207, WINTER PARK, FL 32789
$495,00036 Days on yellowkey MLS ID: O6391523
0 Days Off yellowkey (back on 4/18/2026)
Bed: 1 Bath: 2.0 Liv Area Sq Ft: 1149 Built: 1981 Tax: $6,512 (2025)Community: Park West CondoCondo
Taxes:$6,512
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Enjoy the best of downtown Winter Park living in this spacious 1-bedroom, 2-bathroom condominium located in the highly sought-after Park West Condominiums. This well designed residence offers comfortable living with the rare convenience of two full bathrooms. Park West is a gated community known for its exceptional amenities, including a resort-style swimming pool, lighted tennis courts, and a clubhouse perfect for social gatherings and private events. Residents also benefit from secure entry, covered parking, and beautifully maintained grounds, creating a quiet and private residential setting just moments from the heart of the city. One of the community’s most desirable features is its unbeatable proximity to Park Avenue. Just a short walk away, you’ll find Winter Park’s premier destination for boutique shopping, award-winning restaurants, cafés, art galleries, Central Park, Rollins College, and the weekly farmers market. Whether you’re enjoying a casual coffee, fine dining, or cultural events, everything downtown Winter Park has to offer is right at your doorstep. This condominium combines location, convenience, and lifestyle amenities, making it an ideal opportunity for full-time residents or those seeking a low-maintenance home in one of Central Florida’s most prestigious neighborhoods.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Kevin Mcclanahan (407-491-8509)
311 E MORSE BLVD #2 - 5, WINTER PARK, FL 32789
$2,100,000109 Days on yellowkey MLS ID: O6370558
0 Days Off yellowkey (back on 4/16/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1900 Built: 1960Monthly Fee: $2,622 Tax: $6,719 (2025)Community: Whispering Waters/Phillips Circle RepCondo
Taxes:$6,719
Remarks: Under contract-accepting backup offers. Enjoy the Winter Park lifestyle in this spacious 2-bedroom, 2-bath lakefront condo offering 1,900 square feet in the heart of downtown Winter Park. Enjoy serene lake views from the 120 sq ft screened porch—perfect for morning coffee or evening wine. The light-filled living area features soaring 8 ft 10 in ceilings, creating an open, airy atmosphere. A cozy family room offers built-in shelving and a wet bar, ideal for relaxing or entertaining. The galley kitchen features granite countertops, a natural gas range, and a convenient laundry closet with a stackable washer and dryer. The primary bedroom boasts a walk-in closet with ample storage, additional closet in the rear alcove, and a primary bath with dual sinks and a walk-in shower. The secondary bedroom includes an adjoining office alcove, while the secondary bath offers a walk-in shower. Neutral tones flow throughout the condo, and the dinette provides beautiful views of Lake Osceola. Completely rebuilt in 2011 with new plumbing, electrical wiring, air conditioning, and ductwork, this home offers modern efficiency and peace of mind. A covered boat slip (#15) with lift, two covered parking spaces in the gated underground garage accessible with a key access in the elevator, approximately 90 sq ft of private utility storage, and a community pool complete this exceptional offering. Just steps from Park Avenue, enjoy walkable access to premier shopping, dining, museums, and seasonal events, making this a rare opportunity for true lakefront living in one of Winter Park’s most desirable locations.
Listing Agent: Megan Cross (407-353-9997)
7336 FOREST HILL CT #240, WINTER PARK, FL 32792
$169,90056 Days on yellowkey MLS ID: O6386461
REDUCED by $10,000 (5.6%) on 04/08/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 990 Built: 1984Monthly Fee: $450 Tax: $2,899 (2025)Community: Hidden Oaks Condo Ph 12Condo
Taxes:$2,899
Remarks: Updated Winter Park Townhome!! If you are looking for LOCATION this is the property for you. This well maintained END unit is move in ready: two-story 2 Bedrooms 1.5 Bath townhome style condo with two designated parking spaces. Upon entering you are greeted with a large living and dining room space. Tiled floors, tons of light, neutral colors, wet bar area are a few of the amazing qualities of this space. Just off the dining room you will find the kitchen and eat in kitchen area. Updated cabinetry, quartz counters, stainless steel appliances and tons of storage. The eat in kitchen space is highlighted with a decorative wall and sliders leading to your fully fenced private backyard space. Upstairs you will find hardwood flooring, two bedrooms and master bathroom with double vanity set and brown glass sink top in dark coffee. Hidden Oaks community features on-site security, community pool & fenced playground area. Near Full Sail, UCF, Valencia & Rollins College, with easy access to shopping, Winter Park schools, Medical Facilities, Downtown Orlando, Downtown Winter Park, FL-408, FL-417 and the airport. This wonderful unit has it all...the only thing missing is YOU!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Steven Looper (321-662-3582)
3217 OAK LAWN PL #211, WINTER PARK, FL 32792
$179,00041 Days on yellowkey MLS ID: O6390713
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1117 Built: 1984 Tax: $2,909 (2025)Community: Hidden Oaks Condo Ph 11Condo
Taxes:$2,909
Remarks: Rare corner unit opportunity — this 3-bedroom, 2-bath home sits on the upper level of the highly sought-after Hidden Oaks community in Winter Park, tucked in one of the neighborhood's quieter, more private sections away from street traffic and parking lot noise. Unlike most units in the complex, this home benefits from windows on three sides, flooding every room with natural light throughout the day — a feature you simply won't find in the standard interior units. The second-floor position adds both privacy and tranquility, with no footsteps overhead and elevated views of the surrounding mature tree canopy that Hidden Oaks is known for. The functional floor plan makes the most of every square foot, with a spacious living area that feels open and airy thanks to that exceptional three-sided window exposure. The kitchen has been thoughtfully updated with a brand-new range, and the refrigerator, dishwasher, and washer/dryer were all replaced approximately three years ago — move-in ready from day one. Perfectly positioned for convenience without sacrificing peace and quiet: minutes from Full Sail University, UCF, downtown Winter Park, and downtown Orlando, with quick access to the 408 and 417. One assigned parking space is included, with two additional permits available through the association.
Listing is courtesy of: SHORES REAL ESTATE (407-353-0106)
Listing Agent: Abby Yelken (407-496-9822)
7454 WYNNEWOOD SQ #188, WINTER PARK, FL 32792
$229,0009 Days on yellowkey MLS ID: O6386578
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1151 Built: 1984Monthly Fee: $450 Tax: $2,858 (2025)Community: Hidden Oaks Condo Ph 10Condo
Taxes:$2,858
Remarks: Updated Winter Park Townhome!! If you are looking for LOCATION this is the property for you. This well maintained unit is move in ready: two-story 3 Bedrooms 2.5 Bath townhome style condo with two designated parking spaces. Upon entering you are greeted with a large living and dining room space. Tiled floors, tons of light, neutral colors, wet bar area are a few of the amazing qualities of this space. Just off the dining room you will find the kitchen and eat in kitchen area.few stainless steel appliances and tons of storage. The eat in kitchen space is highlighted with a decorative wall and sliders leading to your fully fenced private backyard space. Upstairs you will find hardwood flooring, three bedrooms and master bathroom with a single vanity . Hidden Oaks community features on-site security, community pool & fenced playground area. Near Full Sail, UCF, Valencia & Rollins College, with easy access to shopping, Winter Park schools, Medical Facilities, Downtown Orlando, Downtown Winter Park, FL-408, FL-417 and the airport. This wonderful unit has it all...the only thing missing is YOU!
Listing is courtesy of: APPLE REALTY (407-647-6766)
Listing Agent: Manoj Patel (407-451-5872)
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