Winter Park Condos For Sale - 100 condos

Remarks: One or more photo(s) has been virtually staged. **This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features hardwood floors throughout and an open living room with sliding glass doors leading to the community green space that is a tropical oasis. The adjacent dining area includes a stackable washer/dryer and flows into a modern kitchen with floor-to-ceiling cabinetry, granite countertops, and stainless steel appliances. Both spacious bedrooms sit near the entry, with the primary suite offering a walk-in closet and a sleek ensuite bath with a glass-front shower and floating vanity—mirrored in the newly updated guest bath as well. Enjoy low-maintenance living with access to resort-style community amenities including two pools, tennis courts, and a gym—all in a prime location! Schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Thomas Nickley, Jr (407-629-4420)

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)

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)

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)

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)

Remarks: Under contract-accepting backup offers. Low HOA!!! Spacious 2-bedroom unit offering 1,008 sq ft plus a 16x8 enclosed Florida room and a one-car garage, presenting a great opportunity for an investor or buyer ready to add value. The unit has been professionally cleaned, and following a water heater failure, ServPro inspected and addressed the area—no severe damage reported. As a result, baseboards have been removed throughout, and carpet has been removed from both bedrooms, leaving bare concrete and a blank slate for new flooring. The home features vaulted ceilings in the living and dining areas, a large welcoming foyer, and a functional kitchen with pantry and dual lazy Susan cabinets. Major components include a 2023 roof, 2025 water heater,2010 A/C, poly piping, and a Gould-brand electrical panel. HOA covers roof, exterior maintenance, termite bond, and pest control; buyer approval is required. Recent comparable sales support strong potential—bring your vision and make this one your own.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Jacob Zampella (321-945-2273)

Remarks: Townhouse opportunity—ideal for either personal residence or investment—featuring 2 bedrooms and 2.5 bathrooms. Conveniently located near supermarkets, shops, universities, and public transportation. At closing, all outstanding HOA special assessments will be paid off. The Townhome is rent $1,600. The unit is located in Winter Park Area HOME GUARANTY OF AMERICA HWA 13 MONTH INCLUDED.

Listing is courtesy of: NAIM REAL ESTATE LLC (818-268-9917)

Listing Agent: Daiana Garcia Medrano (321-315-4686)

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)

Remarks: Major Price Improvement! Here is your rare opportunity to own a studio apartment in Whispering Waters, a 55+ iconic Condominium located just steps from Park Avenue and fabulous historic downtown Winter Park!  This architectural mid-century beauty was built in 1960 and has survived every major hurricane since then. Whispering Waters has passed the Milestone and  Structural Integrity Reserve Study with flying colors. Enjoy all of these activities nearby including the award winning restaurants, boutique shops and museums.  There is walkability to the Alfond Inn, Rollins College, the Sunrail / Amtrak Station, Farmer's Market and all things the Park Avenue area has offers including beautiful parks and lakes to explore.  Just outside your door and on the shore of Lake Osceola you will find the historic Winter Park Boat Tour.  At Whispering Waters the lush community grounds and shared patios are a tropical oasis of flowering plants and charming decorative ponds.  This highly sought after ground floor corner unit comes with an abundance of natural light and has just been freshly painted as well as new energy efficient windows installed.  It features neutral colors, easy care ceramic tile in the kitchenette & bathroom, with laminate flooring in the main living area.  The low monthly HOA fee includes electricity, gas, heat, water, sewer, trash, grounds care, pool service and all building exterior maintenance. The owner pays for Cable & Internet. Association approval is required for all new owners.  One assigned & deeded exterior parking space comes with this unit. Drop your groceries off in the covered and gated parking garage in the basement, with a short elevator ride to the ground floor.  Amenities include an onsite manager, pool, clubroom, covered boathouse with boat slips (Docks may become available for lease or purchase). Whether you are seeking a full-time residence, a winter retreat or mother/father in-law suite, this home offers effortless, low-maintenance living-just lock and leave!l Schedule your showing soon as this gem is sure to go quickly! Professional photographs coming soon!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Jeff Dodds (407-937-9521)

Remarks: This 2 bedroom, 1.5 bathroom condo features a townhome style layout with spacious living areas. Recent enhancements include the removal of dated laminate to reveal ceramic tile flooring throughout the main level, installation of stylish luxury vinyl plank on the upper level, new carpeting on the staircase and landing, and a full interior repaint. In addition, the sliding glass doors were professionally serviced, including roller replacement, track repairs, and installation of new locks to ensure smooth, secure operation. Deluxe vinyl fencing was installed throughout the community by the HOA replacing the older wooden fencing. The fencing was replaced with the vinyl after the listing photos were taken, please view the video to see the replacement vinyl fencing. Enjoy convenient features including an in-unit washer and dryer combo, storage under the stairs, and a large carport with an attached storage shed. The spacious primary bedroom opens to a large screened-in balcony. Ideally located just 15 minutes or less to UCF, Rollins College, Valencia East, and Full Sail University, and only 20 minutes to Orlando International Airport. Whether you’re a first-time home buyer, student, investor, or looking to make your move into Winter Park, this home offers affordability, convenience, and plenty of potential!

Listing is courtesy of: IAD FLORIDA LLC (407-720-0020)

Listing Agent: Karen Salter (352-227-0451)

Remarks: Welcome home to this stunningly updated two-story condo that perfectly combines modern elegance with everyday comfort. Featuring 2 spacious bedrooms and 2.5 baths, this home has been thoughtfully updated with high-end designer finishes throughout. The first floor showcases stunning new tile flooring in a striking neutral pattern, creating a modern and inviting living space, while the second floor features durable and stylish vinyl flooring for added comfort. The fully renovated bathrooms boast contemporary designs and quality craftsmanship, and a brand-new AC system ensures year-round efficiency and peace of mind. Natural light pours into every corner of the home, enhancing the open layout and highlighting the elegant upgrades. Ideally located just minutes from shopping, dining, and top-rated schools, this condo offers both luxury living and everyday convenience. Don’t miss the opportunity to own this move-in-ready gem in a prime location!

Listing is courtesy of: STIRLING INTERNATIONAL REAL ES (407-250-1000)

Listing Agent: Rosa Rodriguez (407-832-1185)

Remarks: Step into this beautifully renovated two-story condo offering the perfect blend of modern style and everyday comfort. Featuring 2 spacious bedrooms and 2.5 updated bathrooms, this home has been thoughtfully upgraded from top to bottom. The first floor showcases elegant marble-look tile flooring, creating a sleek and durable living space ideal for both relaxing and entertaining. Upstairs, you’ll find stylish and low-maintenance vinyl flooring throughout, adding warmth and continuity to the private living quarters. The fully renovated bathrooms boast contemporary finishes and fixtures, delivering a fresh, spa-like feel. A brand-new AC system ensures year-round comfort and energy efficiency. With its modern upgrades, functional layout, and move-in-ready condition, this condo is a perfect choice for buyers seeking both style and convenience.

Listing is courtesy of: STIRLING INTERNATIONAL REAL ES (407-250-1000)

Listing Agent: Rosa Rodriguez (407-832-1185)

Remarks: Beautifully updated 2BD/2BA single-story condo in peaceful Goldenrod Villas, Winter Park. Enjoy an insulated, screen-enclosed lanai with its own AC unit, plus a brand-new backyard deck and private patio. Both bedrooms offer ensuite baths with updated vanities and large walk-in closets. NEW luxury vinyl plank flooring throughout. Extended kitchen with added cabinets and bar seating. Laundry room includes extra storage. Freshly painted interior, lanai, and fence. Community pool included. Conveniently located near top-rated schools, shopping, dining, and major roads. Move-in ready-schedule your showing today!

Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-891-1220)

Listing Agent: Stephanie Sanchez (407-405-1462)

Remarks: Prime location meets exceptional value in the highly sought-after Winter Park area! This first-floor condo offers unbeatable convenience and strong investment potential in one of Central Florida’s most desirable communities. Ideally positioned just steps from the community pool and on-site laundry facilities, it provides easy, everyday access to key amenities. Whether you’re a first-time homebuyer ready to enter the market or an investor looking for a property with solid rental appeal in a high-demand location, this condo delivers both lifestyle and long-term opportunity. Don’t miss your chance to secure a well-located property at an attractive price point.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Leticia Morales (407-515-0318)

Remarks: This charming 2-bedroom, 1.5-bath condo offers a desirable townhome-style layout with spacious living areas and thoughtful storage throughout. The community features deluxe vinyl fencing installed by the HOA, along with a clubhouse and a community pool, providing great amenities for residents to enjoy. Inside, you’ll find the convenience of an in-unit washer and dryer combo, ample storage under the stairs, and a large carport with an attached storage shed. The spacious primary bedroom opens directly to a generous private balcony—perfect for relaxing or unwinding after a long day. Ideally located just 15 minutes or less from UCF, Rollins College, Valencia East, and Full Sail University, and only 20 minutes from Orlando International Airport. Whether you’re a first-time homebuyer, student, investor, or looking to make your move into Winter Park, this home delivers affordability, convenience, and excellent potential.

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Javier Albelo Rivera (407-655-7101)

Remarks: 2 bedroom, 2 bathroom condo located in the desirable and well maintained Waterfall Cove community in Winter Park. Unit is long-term tenant occupied, offering immediate rental income for an investor buyer. Interior is in original condition and presents an excellent opportunity for updates and value enhancement. Enjoy a highly walkable location close to Whole Foods, LA Fitness, Winter Park Village, shopping, dining, and more. Community amenities include a pool, dog park, and mature landscaping. Convenient access to I-4 and major employment centers. Please do not disturb tenant. Call or text for showing instructions

Listing is courtesy of: MTRE GROUPE LLC (786-282-9992)

Listing Agent: Mauricio Toro (786-282-9992)

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)

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)

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. 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!

Listing is courtesy of: REALCOM REAL ESTATE SERVICES INC (407-621-6856)

Listing Agent: Janice Erickson (407-621-6856)

Remarks: 2 Bedroom 2 bath condo 1 block south of University Blvd great location for UCF or Full Sail University this quiet neighborhood has tree lined streets and a community pool. Great investment opportunity for parents looking to house their and rent out after they graduate.

Listing is courtesy of: PREMIER MANAGEMENT GROUP INC (407-370-4400)

Listing Agent: Ken Warren (407-370-4400)