Location: Winter Park , 32792
Do Not Show Listings
1507 GOLFSIDE DR, WINTER PARK, FL 32792
$925,00019 Days on yellowkey MLS ID: O6395355
REDUCED by $50,000 (5.1%) on 04/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2003 Built: 1981 Tax: $2,783 (2025)Community: Greenview At Winter PinesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,783
Elementary School: Brookshire Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Glenridge Middle
Remarks: One or more photo(s) has been virtually staged. OUTSTANDING RENOVATION in a FANTASTIC LOCATION! Peace, Quiet & GOLF COURSE LIVING! This rare opportunity places you along the 13TH tee & offers tranquil backyard views of the 16TH fairway of the Winter Park Pines Golf Course (WP18)! Tree-lined street welcomes you to this completely renovated Floor to Ceiling ONE STORY beauty offers Serendipity LW Wood & porcelain tile flooring throughout. Updates include (but definitely not limited to) BRAND new kitchen with Stainless Steel Appliances, new cabinets & quartz countertops. Formal living & dining rooms PLUS Family room with vaulted ceilings featuring a new electric fireplace for amazing ambiance and sliding doors inviting you to new brick pavered 31x 11 screened porch overlooking newly refinished sparkling pool & golf course (no rear or side neighbors!!) Bedroom wing of home offers a large inside laundry room, beautiful guest/pool bath with dual sinks & shower/tub and 2 fresh guest bedrooms. THE PRIMARY SUITE has been thoughtfully remodeled with sliding doors to pool, AMAZING primary bath with oversized work-of-art shower with dual shower heads, dual vanity, separate water closet & HUGE walk-in closet! Extras include: NEW double paned windows & 3 sliding doors to pool/patio, crown molding, NEW roof November 2024, oversized 2 car garage, NEW landscaping, all NEW ceiling fans & light fixtures, NO HOA!! Zoned for Brookshire Elementary, Glenridge Middle & Winter Park High. WELCOME HOME!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Catherine D'Amico (407-252-3210)
2220 FAIRGLENN WAY, WINTER PARK, FL 32792
$674,9004 Days on yellowkey MLS ID: O6399993
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2636 Built: 1986Monthly Fee: $53 Tax: $3,357 (2025)Community: Quail RunSingle Family
Taxes:$3,357
Elementary School: Red Bug Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Experience the perfect blend of classic elegance and modern comfort in this spacious pool home. From the moment you step inside, the open spindle staircase sets a sophisticated tone that carries throughout the residence. In the Heart of the home is an upscale Kitchen equipped with solid wood cabinetry, sleek granite countertops, and a convenient breakfast bar for your morning breakfast or casual dining. Move freely from inside to outside through 3 sets of sliding glass doors in the kitchen, dining room and great room. Just walk out anytime to the massive brick paver patio and enjoy one of the two covered patio areas. The outside is Entertainment ready as the expansive brick pavers wrap around the pool, creating a seamless environment perfect for hosting summer parties or quiet evening dips. On the cool days you can retreat to the family room to enjoy the warmth of the wood-burning fireplace. The primary Suite is a true getaway featuring direct pool access via private sliders, a generous walk-in closet, and a spa-like bath. Indulge in the soaking tub or the walk-in shower with double shower heads. Includes double vanities and ample storage for a clutter-free environment. The upper level will allow family and guests to feel right at home with three spacious bedrooms and a dedicated full bathroom upstairs. You can also rest easy knowing that the Roof was installed in 2018, the Hot Water Heater was installed in 2018, and the HVAC system was installed in 2019. An oversized 2-car garage offers room for a workbench and "toys" plus an inside laundry room and convenient half-bath are located close by. This prime location is ideally situated near A/B-rated schools, UCF, and Oviedo Hospital. Enjoy easy access to the 417 and Aloma Ave with plenty of shopping, Winter Park’s nightlife and the Tuscawilla Country Club just minutes from your front door. If this sounds like YOUR Dream home, please come see it today!
Listing is courtesy of: ELLIS GROUP REALTY, LLC (407-960-4545)
Listing Agent: Jay Lacourt (386-313-5008)
144 LEWFIELD CIR #144, WINTER PARK, FL 32792
$137,00040 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
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
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)
350 CORNWALL RD, WINTER PARK, FL 32792
$775,00023 Days on yellowkey MLS ID: O6394524
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2038 Built: 1963 Tax: $2,127 (2025)Community: Winter Park Pines RepSingle Family
Taxes:$2,127
Remarks: One or more photo(s) has been virtually staged. Fully reimagined and COMPLETELY RENOVATED with Custom features, this stunning 4-br, 3-ba home in desirable Winter Park Pines sits proudly on a spacious corner lot and offers Modern Luxury with thoughtful, HIGH END UPGRADES throughout. The interior showcases all-new cabinetry and countertops, highlighted by a dramatic waterfall kitchen island, brand-new appliances including a built-in microwave tucked into a custom pantry cabinet. Every detail has been carefully considered, from new luxury vinyl flooring and interior doors to upgraded closet shelving, sleek bathroom mirrors, and stylish shower enclosures. Sound insulation enhancements in key areas—including the primary suite, bathrooms, and kitchen walls—provide added comfort and privacy, while smart ceiling fans, dimmable lighting, USB charging outlets, and pre-wiring for under-cabinet lighting and wall-mounted TVs bring modern convenience to everyday living. Beyond the interior, the home continues to impress with major system upgrades and durable exterior improvements designed for long-term peace of mind. Enjoy a BRAND NEW ROOF with transferable warranty, updated soffit and fascia, rot-proof siding and porch columns, and new fiberglass exterior doors with built-in blinds. The property also features a new irrigation system, vinyl fencing, and an expansive 3+ car driveway. Behind the walls, everything has been upgraded—including full electrical rewiring with a new 200-amp service, all-new plumbing from underground lines to fixtures, and a high-efficiency HVAC system with new ductwork and insulation for maximum energy savings, making this home truly MOVE-IN READY with no detail overlooked. FYI-Dumpster to be removed and pressure washed and Install of PVC fence w/ gate at driveway on 04/09.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Kelly Butterfield (407-463-1289)
1108 FAIRWAY DR, WINTER PARK, FL 32792
$725,00053 Days on yellowkey MLS ID: O6386266
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1677 Built: 1978 Tax: $6,713 (2024)Community: Golfside Sec 03Single Family
Taxes:$6,713
Remarks: Offering WELL BELOW appraised value!! Buyer financing fell through, act quickly this one wont last long. In one of Winter Parks most sought after neighborhoods, take a look at this exceptional 3-bedroom, 2-bathroom pool home with an additional bonus space. Completely reimagined with a designer’s eye, this residence blends high-end aesthetic with the ultimate peace of mind—with a newer roof, A/C, and water heater. Step inside to a Sun-filled sanctuary featuring new luxury vinyl plank flooring and gorgeous tile. The heart of the home is the brand-new chef’s kitchen, featuring custom white oak wood cabinetry, rare Taj Mahal quartzite countertops, and elegant champagne bronze finishes throughout. The kitchen flows seamlessly into the living areas, where new tile work elevates the wet areas for a cohesive, upscale feel. Work from home in style in the dedicated bonus room, an ideal footprint for a private office or creative studio. This home features true functionally for a family to live in everyday. This one of a kind home features a custom in home laundry room, custom vanities, a fireplace made to enhance the homes aesthetic & custom doors through the entire home. Beyond the interior, your private Florida lifestyle awaits. Retreat to the expansive screened-in pool, patio and large backyard. Located just steps from the Winter Park Pines Golf Course and the scenic Cady Way Trail, this home offers more than just a renovation—it offers a lifestyle. Enjoy easy access to the clubhouse for dining, top-rated schools, and the vibrant culture of downtown Winter Park. With every detail thoughtfully curated and major systems already updated, this is the turnkey masterpiece you’ve been waiting for.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Rene Droz, Iii (407-484-8786)
2401 SUN VALLEY CIR #2401, WINTER PARK, FL 32792
$265,00027 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)
2708 LION HEART RD, WINTER PARK, FL 32792
$627,50048 Days on yellowkey MLS ID: O6387685
REDUCED by $2,000 (0.3%) on 04/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1785 Built: 1963 Tax: $7,007 (2024)Community: Winter Park Pines RepSpa: NoSingle Family
Taxes:$7,007
Remarks: Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a seamless blend of style, comfort, and functionality. Step inside to discover brand-new luxury vinyl plank flooring flowing throughout, creating a warm and cohesive feel in every room. The stunning two-tone kitchen is a true centerpiece, featuring sleek quartz countertops, contemporary finishes, and new appliances to be installed at closing—perfect for both everyday living and entertaining. The upgrades continue in the fully renovated bathrooms, where carefully selected color palettes and high-quality finishes provide a fresh, sophisticated look designed to stand the test of time. Every detail of this home has been meticulously considered, leaving no space untouched. Outdoors, enjoy your private oasis with a newly resurfaced pool—ideal for relaxing weekends or hosting gatherings year-round in Florida’s sunshine. This move-in-ready gem offers the perfect opportunity to own a like-new home in a highly desirable location. Come experience the beauty, quality, and lifestyle that 2708 Lion Heart Rd has to offer—your dream home awaits.
Listing is courtesy of: EQUITYPRO LLC (407-203-6860)
Listing Agent: Navid Rokh (321-900-5977)
7794 COUNTRY PL #2, WINTER PARK, FL 32792
$241,9004 Days on yellowkey MLS ID: O6397587
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1068 Built: 1988Monthly Fee: $296 Tax: $2,620 (2024)Community: Goldenrod Villas CondoSpa: NoCondo
Taxes:$2,620
Elementary School: Eastbrook Elementary
Remarks: Winter Park Clean, updated condo in Move In Condition - The newest condo's year built are located on the last street in the complex where this unit is located which features more contemporary open floor plans and high ceilings. Enjoy the One story living. No apartment living with noisy neighbors. Another BONUS is *** NO condo neighbors across the street from you - private!!** This unit is second to the end of a Quiet Dead End Street. Step into a bright and airy condo featuring laminate and tile floors. Newer painted pastel colors throughout. The updated contemporary kitchen has newer Pecan colored cabinets and newer granite counter tops with stylish designer tile back splash. Both bathrooms have newer vanities and granite counter tops. The second bath features a designer Pedestal vanity with granite top. Many upgraded finishes and fixtures throughout. Features a split bedroom floor plan that provides privacy, both bedrooms have spacious walk-in closets. *** Open living area shines with natural sun light and is open to a screened porch, providing access to the private, fenced back courtyard. This condo has a New (December 2024) High efficiency RHEEM 15.3 SEER AC unit with Heat Pump that helps keep utility costs lower, New Roof (2021), New 6 panel Front entry door January (2025), New carpet in both bedrooms installed January (2025), Replumbed with New PEX plumbing pipes, New Refrigerator (2025) New light fixtures throughout. Features an open eat in kitchen and a large breakfast bar open to living room. As a resident, you'll have access to the community pool and the convenience of being close to the Cross Seminole Trail and Cady Way Trail, Winter Park Village, UCF and Full Sail. This location offers easy access to major roadways, shopping, and dining and is served by the reputable Seminole County Schools. Complete with fenced backyard! Community has swimming pool & bathrooms. ** Exterior of building is scheduled to be painted. ** Professionally cleaned top to bottom for new owners. Never smoked in.
Listing Agent: Tom Bercini (407-925-4760)
2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792
$269,0001 Day 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
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)
2015 SUMMERFIELD RD, WINTER PARK, FL 32792
$1,375,000166 Days on yellowkey MLS ID: O6357615
Bed: 4 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 3024 Built: 1957 Tax: $7,243 (2025)Community: Kenilworth Shores Sec 07Spa: NoSingle Family
Taxes:$7,243
Remarks: Experience refined Winter Park living in Kenilworth Shores, a highly sought after neighborhood near Baldwin Park, Lake Baldwin trails, and the dining and boutiques of Park Avenue. This location places you close to Rollins College, Winter Park High, and the cultural center of Winter Park FL. Inside, natural light moves through open living spaces finished with wide porcelain tile floors. The kitchen stands as a sophisticated gathering space with a large quartz island, custom cabinetry, Bosch appliances, and a walk in pantry. The primary suite offers a peaceful retreat with direct access to the pool and a spa inspired bath. A second ensuite bedroom, dedicated office, and generous flex room provide versatility for daily living. The backyard feels like a private resort with a covered outdoor kitchen and a sparkling pool framed by thoughtful landscaping. This property may qualify for a seller funded permanent rate buydown with a participating lender. Equal Housing Opportunity.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Christina Fata (407-917-8946)
3207 LOWNDES DR, WINTER PARK, FL 32792
$495,00081 Days on yellowkey MLS ID: O6362285
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2028 Built: 1967 Tax: $4,172 (2024)Community: Georgetown EstatesSpa: NoSingle Family
Taxes:$4,172
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: 3 bedrooms PLUS an office (or 4th bedroom) AND a "flex space". Easy access to all of Winter Park, UCF, and south Seminole County from this convenient, central location! If you've been searching for a spacious pool home with plenty of space for playing, entertaining, or even working from home -- you've found it here! When you walk in, you'll appreciate the intuitive flow of living space into the kitchen, with built-in eating space. Off of the kitchen, you'll find a bonus space (perfect for an office or home gym) as well as a large indoor laundry room/mudroom, and the converted garage which is ideal for a playroom or secondary living space. On the other side of the home, 2 secondary bedrooms, an oversized hall bathroom, and a primary with en suite bath. There are additional touches that go a long way, too, including the custom plantation shutters throughout the home and updated countertops in the kitchen. Much of your time will be spent in the backyard, enjoying a fenced in pool, screened porch, new custom shed (2025), and fully fenced yard with turf play area. Systems in the home have been well maintained: roof (2017), HVAC (2017), tankless gas water heater (2018), and brand new electrical updates (2026). The home was also re-plumbed in 2008.
Listing is courtesy of: MILLER GRANT AND COMPANY (407-399-6031)
Listing Agent: Courtney Pelfrey (407-454-0538)
200 SAINT ANDREWS BLVD #2901, WINTER PARK, FL 32792
$225,00019 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
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)
1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792
$480,000Listed 04/20/2026 8:40PM MLS ID: O6399199
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1676 Built: 1984Monthly Fee: $49 Tax: $6,243 (2024)Community: Country LaneSingle Family
Taxes:$6,243
Remarks: Welcome to this fantastic home on beautiful Lake Florence in a great Winter Park location off of Howell Branch Road in Seminole County! This spacious 3-Bedroom, 2-Bathroom house features vaulted ceilings, wood burning fireplace, ceiling fans, and wonderful outdoor areas. The Living Room, Dining Room and Great Room make this home feel large. The main living areas, hallways and one bedroom have engineered hardwood flooring, wet areas have tile flooring and there is carpet in the primary bedroom and bedroom 3. There is also a small nook that would be perfect for a craft area, office or library and it opens to the side courtyard which is fully fenced and a good size storage shed for your convenience. The Kitchen has all standard appliances including refrigerator, range, dishwasher and disposal. There is also a cozy eat in breakfast nook. The Primary Bedroom is located in the back of the home and has a nice walk-in closet with en-suite bath. There are sliding glass doors that open to the huge screened-in patio with optimal views of the lake! You will love to wake up to the gorgeous view! There are two additional Bedrooms and Full Hall Bathroom. Each bedroom has direct access to the screened in porch. This home has a finished two car garage with opener and washer/dryer hookups. Enjoy coffee in your hammock while watching the ski boats inside the screened patio that runs the full rear length of the home, providing the amazing view to the lake and is perfect for entertaining or enjoying an evening cocktail. Close to most major roadways, this home will not last long!
Listing is courtesy of: COLDWELL BANKER VANGUARD EDGE (800-948-0938)
Listing Agent: Jodie Ma (407-221-0775)
2501 TAHOE CIR, WINTER PARK, FL 32792
$259,90082 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
$187,50012 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)
1923 LINDEN RD, WINTER PARK, FL 32792
$475,00022 Days on yellowkey MLS ID: O6393643
REDUCED by $24,999 (5.0%) on 04/17/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2117 Built: 1955 Tax: $340 (2024)Community: Tanglewood Sec 4Single Family
Taxes:$340
Remarks: ***WINTER PARK **** 4 BEDROOMS ****3 BATHROOM **** PAID OFF SOLAR ***** WILL HELP BUYER****METAL ROOF ***1/3 ACRE*** Welcome to 1923 Linden Rd, Winter Park—a well-maintained single-story residence offering space, character, and an exceptional location. Built in 1955, this solid masonry and concrete block home features 4 bedrooms, 3 full bathrooms, and approximately 2,117 heated square feet, with 2,281 total building square feet. Located in the highly desirable area of Winter Park, the home provides convenient access to shopping, dining, parks, and top-rated schools, as well as nearby Park Avenue and downtown Orlando. The interior offers a functional layout with multiple living areas, ideal for both everyday living and entertaining. Original character elements such as plaster interior walls and two fireplaces add warmth and timeless appeal. The centrally located kitchen provides ample workspace and flows seamlessly into the main living areas. Situated on a generous 0.315-acre lot (13,717 sq ft) with approximately 117 feet of frontage and 114 feet of depth, the property offers plenty of room for outdoor enjoyment, future enhancements, or expansion. Additional features include Metal Roof that allows for 20 degrees cool, continuous footing foundation, and package cooling system. A strong opportunity for buyers seeking a well-built home with character, space, and long-term value in a prime location.
Listing Agent: Milton James (407-572-4458)
5473 BRACKEN CT, WINTER PARK, FL 32792
$295,000116 Days on yellowkey MLS ID: O6368415
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1178 Built: 1986Monthly Fee: $101 Tax: $2,205 (2024)Community: Fernbrook TrailsTownhouse
Taxes:$2,205
Remarks: One or more photo(s) has been virtually staged. Move-in ready 3-bedroom, 2-bath townhome in desirable Winter Park featuring recent exterior paint and a clean, modern presentation throughout. BRAND NEW water heater, A/C replaced in 2021, and NEW ROOF (2026). The spacious family room sits beneath dramatic two-story vaulted ceilings highlighted by tongue-and-groove ceiling planks, creating an open and architectural focal point. The functional layout includes a large bedroom and full bath on the main level—ideal for guests, a home office, or multi-generational living. Upstairs, two additional bedrooms share a Jack-and-Jill style bath, offering privacy and efficiency. The kitchen opens to the dining and living areas, making the space well-suited for everyday living and entertaining. Sliding doors lead to a screened-in patio and a private, white PVC-fenced yard—low maintenance and perfect for relaxing or pets. Additional features include wood-look flooring in main living areas, neutral finishes, and abundant natural light. Conveniently located near Winter Park shopping, dining, parks, and major roadways. A strong option for buyers seeking space, location, and low-maintenance townhome living.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: David Fraser (407-920-9749)
3028 GEORGE MASON AVE #J-7E, WINTER PARK, FL 32792
$105,0006 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)
2401 ANTILLES DR, WINTER PARK, FL 32792
$320,000167 Days on yellowkey MLS ID: O6357934
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1719 Built: 1977Monthly Fee: $95Community: Windward Square Sec 1Townhouse
Taxes:$0
Remarks: Fantastic end unit with enclosed Florida Room in the sought after Windward Square! This 3/2 features several updates including a, updated kitchen with 42" wood cabinets, granite counters and a center island! Most rooms have upgraded ceiling fans from Dan”s Fans with a lifetime guarantee. The home has newer A/C, high impact windows and the home has been re-piped for your peace of mind. This is a wonderful space and great to prep for a dinner party! Open floor concept with dining room and family room. Enclosed Florida room with high impact windows is great extra living space marking this home just over 1700sf. Master bedroom is a good size with walk in closet. Secondary rooms are spacious and full 2nd bath. You have a wonderful front fenced courtyard and a nice sized fenced back yard. End unit and 2 assigned car parking spaces. Community features low HOA and community pool, gated back entrance for easy access to Semoran, tennis courts and club house. Zoned for great Seminole County schools and minutes to shopping/dining, Altamonte Springs Mall, Downtown Winter Park, Full Sail University and to UCF. This is a great one level townhome with very reasonable HOA.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: George Freelove (407-408-5167)
1792 CHILEAN LN, WINTER PARK, FL 32792
$325,00089 Days on yellowkey MLS ID: O6375881
1 Days Off yellowkey (back on 4/21/2026)
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 984 Built: 1959 Tax: $2,677 (2024)Community: Eastbrook Sub Unit 05Single Family
Taxes:$2,677
Remarks: Under contract-accepting backup offers. Welcome home to this darling, move-in-ready Winter Park gem! Perfectly suited as a starter home or investment opportunity, this beautifully remodeled 3-bedroom, 1-bath residence features laminate flooring throughout, a fully remodeled bathroom, and an updated kitchen with granite countertops and stainless steel appliances. Updated plumbing completed in 2014 and a 2017 AC system offer added peace of mind, and tasteful window treatments are already in place. Step outside to a large, fully fenced backyard complete with a fire pit and shed—perfect for entertaining, relaxing, or enjoying Florida evenings. Ideally located in a great area of Winter Park, close to shops, dining, and approximately 30 minutes to everything you want to enjoy in Orlando. One of the best-priced remodeled homes in the area—this charming property is a must-see! NO HOA! Tour this home at
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Catherine Lambert Pa (407-908-2525)
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