Homes for Sale in Winter Park

This stunning & revived one-story Winter Park home is the perfect mix of classic charm & modern comforts. Featuring NEW oak hardwood floors, crown molding, two master suites & soaring ceilings, no expense was spared in the recent extensive remodel with top-of-the-line luxury finishes. The split floor plan is both wonderful & fascinating. As you go into the home you enter the living room & close by is the sun room, two bedrooms, NEW bathroom w/ tiled shower/tub & built in shelves. The bonus room off the living room can be a fifth bedroom, office, nursery, workout room, wine room, etc. The formal dining room nearby opens to a tranquil private courtyard & near that is the laundry room w/ utility sink. Next to the kitchen is an additional living room w/ natural gas fireplace & built in cabinets/shelves. Now step outside to your shaded backyard oasis w/ a NEW privacy fence w/ gate, oversized patio for dining/entertaining & a large storage shed/workshop. You'll love the abundance of natural light especially through the large outdoor courtyard in the middle of the home w/ views & access from the kitchen, primary master suite & living room. Featuring NEW impact rated 8 ft. tall sliding glass doors including a 12 ft wide grand entrance which opens from both directions in the middle near the living room. With views of towering trees this area offers endless possibilities & is the perfect transition for indoor & outdoor entertaining & relaxation. The open kitchen has been transformed into a spectacular masterpiece featuring vaulted ceilings, skylight, Calcutta quartz, center island, large peninsula w/ bar seating & decorative pendant lighting, new stainless appliances including Brama microwave, vented hood, custom backsplash & solid wood cabinets, including 42 in. upper cabinets & four large pantry cabinets. The primary master suite is spacious w/ vaulted ceilings, two walk-in closets & one w/ a closet organizer. The NEW master bathroom is exquisite boasting a large glass shower w/ two shower heads & dual vanities w/ quartz. The second master has a private entrance which is perfect for guests or mother-in-law suite, walk-in closet & NEW bathroom w/ spacious glass shower & a vanity w/ quartz. The air conditioned two car garage has a NEW garage door/opener, NEW epoxy floor & lots of extra storage areas. The long driveway is perfect for guests, multiple cars & parking. Other upgrades include a NEW roof/gutters, NEW plumbing/electrical/AC, NEW windows/doors, NEW int/ext paint, NEW pavers/landscaping/irrigation & Rinnai tankless gas water heater. Please ask for a list of the $290K in improvements & is attached to MLS. Centrally located on the famous tree lined Palmer Ave, you're a short stroll to Phelps Park & the YMCA, and minutes to shopping & dining on Park Ave, Interlachen Country Club & Winter Park Racquet Club. Don't miss your chance to make this truly breathtaking home yours!

Nestled in Winter Park on a brick paved street this beautiful and deceptively large 2 bedroom residence with over 1600sqft of living space. Includes 2 masters, 2.5 bathrooms, a large recreation/study bonus area, full kitchen with accessories, and laundry. Lovely secluded garden. Attached 1 car garage with driveway parking for 2. Walk to your favorite Park Ave restaurants, stores, and coffee shops. Minutes from farmers market. Winter Park High school district and close to Rollins College. Call today to schedule a viewing.

One or more photo(s) has been virtually staged. You've found THE ONE! Welcome to this beautifully maintained condo in Winter Park's Four Seasons community—perfect for those seeking a low-maintenance lifestyle in a prime location! As you walk in, the kitchen, dining, and living areas are seamlessly connected creating a warm and cozy space. A private, enclosed porch extends your living space into the outdoors where the possibilities are endless! Upstairs, you’ll find two generously sized bedrooms as well as the primary bathroom which has been recently updated. The second floor even has its own exit door, providing an additional layer of accessibility and convenience. This home’s thoughtful updates include new porcelain tile, marble and laminate flooring, refreshed bathrooms, and upgraded windows, exterior door, and patio fence. Essential upgrades like a new roof (2023), replumbing (2019), and BRAND NEW electrical panel (October 2024) mean peace of mind for years to come. Located just steps from a tranquil courtyard and your reserved covered parking spot, this condo also offers access to Four Seasons' fantastic amenities, including three pools (one nearby!), tennis courts, clubhouse and beautifully landscaped grounds. Enjoy easy access to Winter Park’s shopping, dining, and cultural scenes—making this condo a true gem in one of Central Florida’s most vibrant communities! Schedule your showing today!

Welcome to Winter Park at the Enclave at Hawks Crest! This beautiful townhome, located in a gated community, features 3 bedrooms and 2.5 bathrooms with a fantastic layout plus 2 car-garage. Upon entering, you’re greeted by a lovely foyer that opens up to a bright and spacious living area. The kitchen, perfect for the family chef, offers stainless steel appliances and a large island with seating. Upstairs, enjoy a private primary bedroom with an ensuite, while two additional bedrooms share a second full bathroom. The private patio backs onto a conservation area, ideal for gatherings and relaxation. The community offers excellent amenities, including a playground, pool, and picnic areas. Conveniently located just minutes from shops and restaurants. Top rated schools!! Don’t miss this opportunity to own your dream home in this wonderful community—schedule your showing today!

Step inside this newly staged model home! Discover an incredible opportunity to own a solid concrete block construction townhome in the desirable Winter Park community, now available at entry-level pricing! This spacious three-bedroom, three-and-a-half-bath residence offers remarkable value and potential for those looking to invest in a quality home. While the pricing reflects the potential need for improvement, particularly to the main-level wood floors due to minor damage from previous rental use, this townhome is ready for your personal touch. As you enter, you'll be greeted by a grand foyer and a convenient half bath, ideal for entertaining guests. The open-concept kitchen seamlessly connects to the sophisticated dining area and inviting great room, creating the perfect environment for family gatherings and social events. Enjoy culinary delights with stylish white cabinetry, silestone countertops, and a top-of-the-line KitchenAid appliance package, including a natural gas range. The expansive floor-to-ceiling storefront glass floods the interior with natural light and offers stunning views of the surroundings. Step outside to enjoy picturesque sidewalks within the community or relax in the tranquil ambiance of your private, fully fenced backyard. Upstairs, you'll find three luxurious bedrooms, each with its own en suite bath, ensuring ultimate privacy. The primary suite features a spacious walk-in closet with a custom closet system, while the spa-inspired bath boasts a dual-sink vanity, an oversized glass shower, and a separate water closet for added convenience. Unwind on the large balcony with your morning coffee or evening relaxation and appreciate the convenience of a second-floor laundry room. The generous two-car garage is equipped with an EV charging plug, catering to eco-friendly living. This is a unique chance to secure a well-built townhome at an attractive price point. Don’t miss out on this exceptional value—schedule a viewing today and discover the potential that awaits in this Winter Park townhome!

MOVE IN READY 3 bedroom / 2 full bath bungalow in PRIME LOCATION! Just steps from Dubsdread Golf Course, this home is a true gem with no HOA fees, plus easy access to downtown Orlando and Winter Park Village. Residence offers 3 bedrooms and the rare advantage of 2 updated full bathrooms. Kitchen boasts updated cabinetry, granite countertops, and stainless steel refrigerator, stove, dishwasher, and microwave. Enjoy low-maintenance ceramic tile floors, primary bedroom with ensuite bath, and a large backyard perfect for entertaining. 2020 roof and newer water heater, this home is move-in ready and waiting for you!

Under contract-accepting backup offers. Welcome to your meticulously maintained 3-bedroom, 2-bath townhome in the heart of Winter Park! This stunning residence boasts two covered parking spaces and one uncovered parking space which allows room for guests. Step inside to discover a warm and inviting living space with tile floors throughout for easy upkeep. The home seamlessly flows with not one, but three private outdoor areas, perfect for relaxation and entertaining. At the center of the home, you’ll find a serene zen atrium that's screened in, inviting you to unwind in your own peaceful oasis. The tiled screened-in back porch provides a lovely space to enjoy your morning coffee while overlooking the beautifully landscaped, fenced-in backyard, complete with a charming fountain that adds a touch of tranquility. Additionally, a private front porch off the breakfast nook offers another delightful spot to savor the fresh air and is a perfect place for barbequing. Tons of storage space as well, including linen closets, a hall closet, along with a storage shed off the back porch. Upgrades include: newly installed generator hookup so you can keep your essentials plugged in, the home was fully replumbed along with a new water heater within the last 3 years, freshly painted exterior, the HVAC is only 5 years old, brand new Fridge and Washing machine 2024, Dishwasher 2017, Roof 2015 and the roof was recently soft washed for regular maintenance and upkeep. Located in a quiet, well-maintained community, you'll enjoy access to fantastic amenities, including a sparkling pool and tennis courts. With proximity to Disney, the Orlando International Airport and other popular attractions, this home perfectly combines comfort, style, and convenience. Don’t miss the chance to make this townhome your new sanctuary!

Under contract-accepting backup offers. Nestled in the exclusive, gated community of Hawks Crest in Winter Park, this two-story single-family home blends luxury, technology, and thoughtful design. As you step inside, the home’s charm immediately reveals itself, starting with the welcoming warmth of an electric fireplace set against a dramatic stone wall in the family room. This cozy space is made even more inviting by custom abstract wall art that adds a unique touch of character and creativity. The heart of this home is the gourmet kitchen—a dream for any home chef. Outfitted with GE smart appliances, including a sleek French door oven and a GE Café refrigerator with a built-in Keurig coffee maker, the kitchen balances form and function flawlessly. Bright and modern, the kitchen gleams with hardwired under-cabinet lighting, making every detail stand out. It's a space designed for both cooking and gathering, with a flow that leads naturally into the dining area, where ceiling speakers enhance the atmosphere and set the mood for memorable dinners with friends and family. Beyond the main living areas, thoughtful touches continue to unfold. The home office, enclosed by elegant French glass panel doors, is a sanctuary for productivity. Upstairs, a cozy loft features surround sound speakers, perfect for movie nights or weekend get-togethers. And with Google Voice or app-controlled smart lights and blinds on the first level, managing ambiance and privacy is as effortless as it is innovative. In the master suite, the luxurious feel of the home is matched by features designed for relaxation. The master bathroom’s rain shower head creates a spa-like escape, while custom shelving in the closet provides an organized, personal touch. Throughout the home, even the most functional spaces have been designed with care, from the neatly organized pantry to the utility closet’s custom shelving, making storage simple and accessible. Step outside through the stacked patio doors, and you’ll find a screened-in lanai with an outdoor kitchen ready for any gathering. With a built-in grill, hood range, and sink, this area is perfect for al fresco dining, all while ceiling speakers fill the air with soft music or upbeat tunes. The fenced backyard offers a private oasis, ideal for enjoying the beautiful Florida weather in peace. Practicality meets luxury here too. The dual garage features overhead storage bins, providing ample space for everything from tools to seasonal decorations. The water softener offers added comfort throughout the home, while the driveway and lanai cameras, along with dual alarm system keypads and a convenient garage door entry keypad, give peace of mind for a safe and secure living experience. This Winter Park gem is more than just a home; it's a lifestyle crafted for those who value both elegance and innovation. Designed to elevate daily living, it awaits its new owners to enjoy its perfect blend of style, functionality, and modern convenience.

This 1 Bedroom 1 bathroom condo with a peaceful pond view, is located in Winter Park Gardens. This Vibrant 55+ community offers beautifully landscaped grounds, lighted paths, community pool, and a clubhouse where residents enjoy social activities. The prime location provides easy access to a variety of amenities and attractions minutes away from Park Avenue with shops, restaurants, and cultural events. The nearby Azalea Tennis Center and Mead Botanical Gardens offer further enriching experiences. Embrace the serene and active lifestyle this community provides, with the added convenience of being close to Downtown Orlando, Baldwin Park, major highways and convenient to MCO or the Sanford/Orlando Airport. You will have an assigned parking space with plenty of additional parking spaces for guests. This property is a must-see to truly appreciate its charm and amenities.

One or more photo(s) has been virtually staged. Welcome to Winter Park! This beautiful 3-bedroom, 2½-bathroom townhome is like-new and part of the new construction in Grayson Square, now freshly painted for your arrival. Property Highlights: Spacious open gathering room, perfect for entertaining. Covered lanai in the back. Well-appointed kitchen with top-of-the-line stainless steel appliances and a large quartz countertop. Ample storage throughout. Owner’s suite with a spacious walk-in closet. Luxurious ensuite bathroom with a frameless glass-door shower and quartz countertop with double sinks. Washer and dryer included. Community Features: Gated access for added security. Resort-style pool with cabana. High-speed 1GB fiber optic internet. 75 streaming cable and music channels. Location: Minutes away from downtown Winter Park, off Howell Branch Road. Close to major routes: 436, 434, and 417. Nearby Starbucks, Publix, and Walmart. Access to quality Seminole County Schools. 15 min to famous shopping and dining on Park Ave. Don't miss out on this incredible opportunity to make Grayson Square your new home in beautiful Winter Park! HABLO ESPAÑOL.

Pre-Construction. To be built. Discover a unique opportunity to enjoy modern design and quality craftsmanship with this pre-construction contemporary bungalow by the renowned Barefoot Brothers, celebrated for their superior work throughout Winter Park. In collaboration with architect David Crabtree of Hive Workshop, this custom-designed residence is ideally positioned to take advantage of all the attractions Winter Park has to offer—just minutes from Park Avenue, Winter Park Golf Course, and an array of dining and shopping options. This distinctive property provides a rare chance to enjoy proximity to desirable amenities while also offering significant versatility for both personal and income-generating use. The open floor plan in the main residence includes two bedrooms, each with en-suite baths, a half bath, and a dedicated laundry room. Vaulted ceilings with exposed beams and collar ties enhance the airy feel, while quartz countertops, polished concrete flooring, and premium wood cabinetry deliver sophisticated, high-quality finishes. Designed with style and functionality in mind, the gourmet kitchen is equipped with high-end appliances, built-in cabinetry, and shelving, centered around an expansive island ideal for entertaining. Generous natural light floods the home through floor-to-ceiling windows, creating a warm, open atmosphere. Outside, the sleek metal roof and vertical wood slat accents add architectural interest, while an oversized, floating wooden front porch with exposed beams provides ample space for seating and offers a welcoming, shaded retreat. An expansive back porch further enhances the options for outdoor relaxation or entertaining. Thoughtfully designed for privacy, the property features a sliding entry gate at the rear driveway and lush bamboo along both sides, with sea grape hedges framing the wood-fenced front and backyards to create a serene, tropical retreat. Gravel walkways encircle the home, complemented by a paver driveway at the rear, a gravel parking pad, and a paver pad in the front for low-maintenance, elegant outdoor space. Adding to its appeal, the property offers dual street-facing entry points, enhancing convenience for guests and providing easy access from both the front and rear of the home. Beyond the main residence, a two-car garage with a private apartment above offers exceptional flexibility, whether for extended family, rental income, or even a home office. The apartment includes a full bedroom, bath, partial kitchen, living area, laundry room, and a walk-in closet, while the extra-deep garage with built-in storage offers ample room for vehicles, equipment, or collections. This setup presents an ideal house hack opportunity, accommodating multiple uses, including potential income from a garage apartment or additional space for storage or a hobby enthusiast’s collection. With construction already underway, there’s still time to customize finishes, materials, and layouts to suit your personal preferences. This property provides a rare blend of convenience, flexibility, and modern style in a rapidly evolving area—an ideal canvas for your lifestyle, whether you’re seeking a primary residence, an investment opportunity, or a versatile retreat close to Winter Park’s best attractions. Don’t miss the chance to partner with a premier builder to create a home that meets your unique needs.

Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards allow (but is grandfathered in), this backyard provides an ideal place to launch your water adventures, soak up scenic sunsets, and travel by lake to Hillstone for a meal. The CUSTOM POOL is waiting to be enjoyed! It features a custom waterfall, grotto, built-in seating/table and adjacent koi pond, all with a lake view. Recent updates to the home include: shingled roof (2018), DOUBLE PANE WINDOWS (2015), and HVAC (2016). Travertine and tile floors cover the entire home, there is no carpet. The back family room has multiple French doors and offers an expansive view of the lake. Fireplaces are featured in both the office and living room. The convenience of 632 Country Club is unmatched. It is approximately .6 miles from grocery shopping like Whole Foods and Publix or the Winter Park Village - a vast outdoor mall featuring a 20-screen Regal Cinema, Ruth's Chris Steakhouse and Bar Italia, to name a few. For everyday errands like HomeGoods, or workouts at LA Fitness, there is an even closer shopping plaza. An Interstate 4 (I-4) onramp is approximately 2 miles away. Winter Park is bursting with Old Florida charm and was named #38 historic world destinations in 2008 by National Geographic Magazine. At its heart is Park Avenue, famed for its cobblestoned and tree-lined streets with over 140 boutiques, museums, a train station, and world-class dining. 632 Country Club is approximately 1.5 miles from luxurious Park Avenue and 5 miles from downtown Orlando.