Homes for Sale in Winter Park

Under contract-accepting backup offers. Experience the pinnacle of waterfront luxury at Lake Killarney Townhomes. Welcome to Lake Killarney Townhomes, an exclusive enclave of luxury living nestled in the heart of Winter Park, just north of downtown Orlando. Immerse yourself in the beauty of urban contemporary design, where each spacious townhome features private terraces that invite you to unwind in style. These brand-new residences are a testament to sophistication, meticulously crafted with exquisite designer finishes and thoughtful upgrades. Step inside to discover bright, open interiors illuminated by expansive storefront-style windows and soaring 10'6 ceilings, creating an atmosphere of elegance and comfort. The exterior sets a stunning precedent with two-story concrete block construction, complemented by woodgrain composite siding and striking balconies adorned with distinctive glass railings. Each home is equipped with steel insulated flush garage doors and comes with a 10-year structural warranty for peace of mind. Designed with family living in mind, this remarkable layout offers three spacious bedrooms and three-and-a-half luxurious baths. The heart of the home—the kitchen—exudes modern culinary luxury, featuring sleek white cabinetry paired with a bold black-and-white center island. A premium Samsung appliance package, including a natural gas cooktop and built-in wall oven, elevates your cooking experience, while expansive quartz countertops and a solid backsplash create a seamless and sophisticated aesthetic. A generous walk-in pantry adds a touch of convenience for all your culinary endeavors. Ascend to the second level, where a tranquil haven awaits with three well-appointed bedrooms and three full bathrooms, each showcasing unique porcelain tile, modern backlit mirrors, frameless glass shower enclosures, undermount sinks, and custom-built closet systems. Step outside to your expansive outdoor patio, designed with glass railings and pre-plumbed for a future summer or cocktail kitchen, perfect for hosting gatherings or simply enjoying the outdoors. Every detail has been thoughtfully curated to ensure ultimate comfort and style. Embrace the rich history and cultural charm of Winter Park, where boutique shopping, sidewalk cafés, museums, and dog-friendly destinations are just a stone's throw away. Delight in the serene beauty of Lake Killarney right from your side patio or relax at the inviting lakefront pavilion. With your private boat slip, accessing nearby amenities like Trader Joe’s and Shake Shack is effortless. Plus, enjoy community kayak, canoe, and paddleboard racks for a leisurely day on the water. Live the lakefront lifestyle you’ve always dreamed of, where Winter Park's vibrant shopping, dining, and entertainment options are merely moments away. Discover the perfect blend of luxury and convenience at Lake Killarney Townhomes—your new home awaits.

One or more photo(s) has been virtually staged. NEW PRICE ADJUSTMENT! This beautifully updated 2-bedroom, 1.5-bathroom condo in the sought-after Hidden Oaks community is move-in ready and waiting for you! Perfect for students, professionals, and small families, this home offers a modern open-concept layout with stylish finishes and all the updates you need for easy living. Why You’ll Love This Home: * Move-in ready with modern updates * Fully renovated kitchen and stainless-steel appliances * Private outdoor patio with extra storage * Well-maintained community with comprehensive HOA coverage * Fantastic location near UCF, Full Sail, and Winter Park Call today to schedule a private showing!

SPECTACULAR WINTER PARK OPPORTUNITY! This oversized corner lot in Fairbanks Park overlooking Lake Midget and Lake Midget Park is a rare opportunity to build your dream home in Winter Park. The 2-bedroom/1-bath home, original owners since 1941, is available for renovation or new construction. Serene views of Lake Midget from the front porch, that can’t be beat. New restaurant and retail space is being developed across the street on Fairbanks Ave. Close proximity to Rollins baseball field, and less than a mile from Park Avenue, Rollins College, restaurants, shopping, and so much more. Don’t miss this diamond in the rough – call today for your showing!!!

Under contract-accepting backup offers. *OFFERED BELOW APPRAISED VALUE* Charming Bungalow in Winter Park now Available. While originally built in 1932, this house has been completely renovated to today's standards. Upgrades/Improvements include New Roof (2024), New Windows (2024), New A/C and Ductwork (2024), New Flooring throughout (2024 - commercial grade LVP), New Appliances (2024), Completely Remodeled Kitchen and Bathrooms (2024), Whole House Repipe (2022), Upgraded from Septic to Sewer with New Sewer Line (2022), Exterior Paint (2024), and more. This property offers some very unique features. There is a Detached 280 sf Studio with a Full Kitchen and Bathroom. This unit is on a Separate Electrical Meter. There was also a Waterproofing System with Sump Pumps added around the foundation of this studio. This lot is just under 1/4 acre and zoned R-2, which offers a whole yard. The entire street is undergoing a major revitalization, the house next door (to the east), is currently scheduled to be torn down and replaced with 2 new luxury townhomes and priced at just under $1m a piece. This property offers the opportunity to live in the main house and AirBnb the studio, or rent both and hold indefinitely in an area that will only continue to appreciate. Don't miss your opportunity to own your piece of Winter Park. Schedule your private showing today.

Great Schools, Great Location! Great investment property. Low HOA's. This unit offers 3 bedrooms, 2 bathrooms in a Split Plan layout with a Screened rear porch and an Open front porch. Interior Laundry closet with Washer & Dryer. The Community offers a community pool with Playground, Shuffleboard and Clubhouse surrounded by beautiful green landscapes. Centrally located within walking distance to the Lynx bus stop, Publix Supermarket, shopping centers and local restaurants. Windward Square is located just 30 minutes to the local Airport, and about 10-15 mins drive to SR I-4 and SR 417

Discover Your Dream Condo in The Desirable Winter Park Villas Community with a Prime Location! This Fantastic 2 Bedrooms & 2 Bathrooms Condo Features a Spacious Master Bedroom that Comes with An En Suite Bath and Walk-In Closet. There’s Also a Welcoming Guest Bedroom with A Full Guest Bath on the First Floor. Updated Unit Features a Soaring Vaulted Ceilings, Cozy Brick-Front, and a Wood-Burning Fireplace in The Living Room. The Kitchen is a Highlight with its Large Pantry and Ample Cabinet Space. Relax and Entertain on Your Private Patio, Perfect for Unwinding After a Long Day & to Enjoy Florida's Weather. The Community Offers Fantastic Amenities, Including a Pool with A Clubhouse, Fitness Center, Tennis Court and an Outdoor Grilling Area. Conveniently Located Near Full Sail University, UCF, And Local Shopping and Dining Options, And Just a Short Drive to Park Avenue and Downtown Orlando. This Condo Is an Ideal Starter Home or Investment Property. Schedule Your Tour Today and Make This Beautiful Space Your New Home!

Under contract-accepting backup offers. SELLER MOTIVATED! Welcome to this mid-century gem in Winter Park, perfectly located just a five-minute drive from Park Ave and within reach of top shopping, restaurants, and excellent schools. This 4-bedroom, 3-bath pool home sits on just over 0.3 acres and boasts over 2,200 square feet of living space. Enjoy suburban living with a huge backyard, a front yard with a fenced-in garden area, and charming architectural details throughout the home. Inside, you'll find tiled flooring and gorgeous hardwood floors in three of the bedrooms, exposed beams, and modern updates that include a newer roof and newer A/C The kitchen and bathrooms have been tastefully updated, blending classic charm with contemporary conveniences like remote lighting. The master suite features a private entrance leading out to a newly replaced wood deck (2023), offering tranquil views of the backyard. Your home should be your oasis, and the previous owners had this in mind when designing the outdoor space. The vast backyard features a newly surfaced and tiled pool (2024) with a brand-new resort-style deck and patio (2024), perfect for relaxation or entertaining. The pool pump was also replaced in 2022. NOT TO BE MISSED is the oversized detached garage, which includes a versatile air-conditioned space below for storage, a home gym, or other needs. Above, you'll find an additional 600 sqft flex space with its own full bath, ideal for a man-cave, teen hangout, homeschooling, mother-in-law suite, rental property, art or music studio, home office, or whatever you can imagine. This home has been lovingly updated and maintained with the highest quality and care, making it a rare find in this sought-after area. Close to top-rated schools, parks, shopping, dining options, and major highways, making it an ideal location for families and professionals alike. Don’t miss out on this incredible opportunity – schedule your private showing today, as this home won’t be on the market for long!

Welcome to this inviting first-floor condo, designed with an open concept floor plan that seamlessly blends comfort and style. The expansive family room provides a generous space for family gatherings and entertaining, with abundant natural light flowing through large windows and a screened-in porch. This condo features two generously sized bedrooms and two full bathrooms, offering ample space and privacy. The master bedroom includes an en-suite bathroom for added convenience and comfort. The well-appointed kitchen is a chef’s delight, boasting granite countertops and stainless steel appliances, including a full-sized refrigerator, stove, oven, and microwave. Additional cabinet space ensures you have room for all your culinary essentials. For added convenience, the condo includes a washer and dryer. Enjoy relaxing evenings on the screened-in porch or take a short walk to the clubhouse, where you can refresh in the pool or unwind in the warm hot tub. This home is designed to provide comfort and ease, making it the perfect place to settle in and enjoy.

Discover serene lakefront living at its finest in this exquisite 4-bedroom 3 bath home at 279 Rippling Lane. Set against a picturesque backdrop, this property offers breathtaking views and direct lake access, complete with a covered boat dock for your aquatic adventures. The residence seamlessly blends modern luxury with timeless elegance, featuring spacious living areas, high-end finishes, and large windows that invite natural light and lake views indoors. Custom kitchen with quartz and wood counter tops, six burner pro style range. New roof in 2023 and upgraded electric panel 2018 and Air conditioner in 2020. A split floor plan with 3 bedrooms and 2 baths up front and a spacious primary bedroom and bath have vaulted ceilings and a large walk-in closet and overlooking the lake. Enjoy the tranquil ambiance of your private retreat while being just moments away from Winter Park’s vibrant dining, shopping, and cultural attractions. Don’t miss this rare opportunity to own a slice of paradise in one of Winter Park’s most sought-after locations.

Come check out this immaculate 3 bed 2.5 bath home in the heart of Winter Park. The primary bedroom features a balcony looking over the recently updated pool. The home features new vinyl plank flooring through out the home. With an open floor plan, the home is perfect for cooking home cooked meals and entertaining guest. Backyard is fenced in to ensure privacy when enjoying the pool on hot summer days. Property is conveniently located to shopping and entertainment centers.

Under contract-accepting backup offers. Price Improvement! Come see this charming 4/2 home in highly sought after Winter Park! Tucked away in a quiet neighborhood nestled between tall oak trees with NO HOA feels and plenty of space to grow. This adorable home has a master bedroom with 3 additional quaint bedrooms that can also be used for a home office, nursery, art room etc.! The dining room opens to a large living room space with natural lighting from large glass doors and ceiling fan in dining for nice ventilation and additional lighting. The kitchen has a lovely large window with natural light overlooking the huge back yard, wooden cabinets and nice tile flooring which runs throughout the dining and living room areas for easy cleanups. Showers in both the master and hallway bathrooms have newly remodeled. In addition to the one full car garage it boasts a large screened backyard porch providing additional living and/or entertainment space. The large fully fenced in backyard is a great play area for family and/or pets. It also provides ample opportunity for a home addition, pool or use the land to park your boat or a large RV. Roof and AC are 4-5 years old, inside and outside are freshly painted. Located in an A rated school district. Enjoy the convenience of being just minutes away from Rollins College, Park Avenue, Full Sail and the Orlando area via 417 and 436. This home is a perfect blend of convenience and charm with room to expand into the home of your dreams.

One or more photo(s) has been virtually staged. Discover a unique chance to own a home in the delightful Winter Park Hills neighborhood, zoned for top-rated Winter Park Schools (Dommerich, Maitland, and WPHS). This move-in ready, 3-bedroom, 2.5-bath house has been fully renovated with numerous updates, including a 3-car garage, a swimming pool, and a spacious, fully fenced yard. Situated on a corner lot, this home is filled with natural light and features an open, bright floor plan that seamlessly connects the kitchen, living room, and formal dining room. The stunning kitchen boasts 42” white soft-close cabinets, granite countertops, crown molding, and stainless steel appliances. French doors lead out to the oversized patio and backyard, highlighted by a sparkling Pebbletec-finished swimming pool with a sun shelf. The ample outdoor space is perfect for entertaining and relaxing with family and friends year-round. The spacious master bedroom includes French doors that open directly onto the pool deck, a second closet, and a walk-in master closet with custom shelving. The second full bath was updated with a new shower tub in 2022. The laundry room offers generous cabinet and counter space and also doubles as a mudroom. Additional updates include a new roof in 2021 and a new A/C unit in 2023. Don't miss this exceptional opportunity to own a beautifully updated home in Winter Park Hills!