Homes for Sale in Winter Park

Welcome Home to your OASIS! This 5 Bedroom, 4 Bath, Saltwater Pool Home with 2-Car Garage NEW Genie Garage Door Opener. Magnificent Salt Water Pool, Huge Lanai with Fireplace, Full Wet-Bar, Pond with fountain, White Vinyl Fence, Mature Landscaping. Long pavered driveway with plenty of room for all of your vehicles. You’ll fall in love with this Winter Park Home. Once you walk in you will feel like you are on a HGTV set. This Split Bedroom floor plan offers a spacious Primary Bedroom in the rear of the home with beautifully updated Primary Bath. Double Vanity, Granite countertop, Chocolate Brown Cabinets, Tiled Walk-in Shower with Frameless Glass Doors. Two closets in Primary, one walk-in and one reach-in closet. Both front bedrooms are En-Suites. Bedrooms 4 and 5 share hall bathroom with tub and shower. If you are a chef or just a foodie you won’t want to leave this Ultimate Gourmet Kitchen. Zline 6-Burner, Griddle, Professional grade gas range with double electric oven and Zline wall mounted range hood. Dishwasher, two stainless steel farm sinks, wall-mount pot filler, microwave oven and French Door Refrigerator. White Shaker Soft Close, Kitchen Cabinets with Black hardware and high-end granite countertops, adorned by Designer Stone Backsplash. Behind the custom built barn doors is the laundry closet and pantry. The large 7.9 x 5.3 Island seats 6 comfortably. This Dining Room is meant for entertaining. Seats 10-12 comfortably with sideboard, bar hutch and more. French doors off dining room lead out to the Lanai, Pool and Bar area. Living Room is warm and cozy with wood burning fireplace, built-ins, LED recessed lighting. Flooring throughout is porcelain wood-look tile. Looking for a home with storage, this home has custom built-in cabinets in 2 bedrooms and hallway. You'll be amazed how much you can store. If you enjoy outdoor living and entertaining, you’ll never want to leave home. Step outside to a spacious covered lanai with tongue and groove ceiling, wood plank flooring, fireplace, TV and surround sound speakers. Full wet bar, lower stone encased with granite tops. Porch Swing. Fence has double gate on left side of home so you can easily pull your boat or other toys inside. Enjoy the mature Florida landscape as you sit by the pool and bar enjoying your favorite team on the TV with your friends. Pool remarcited and tiled in 2022. New pool equipment 2023, Pool Shed is to the right of the house behind the bar to hold all of your pool supplies. New HVAC 2023. Compressor 2020. Roof was replaced in 2018, house was replumbed and rewired in 2020. All Double Pane Aluminum Windows throughout home.

Custom Waterfront Estate located in the heart of Winter Park with a covered Boat Dock on Lake Maitland - the largest of the Winter Park Chain of Lakes. A timeless Neoclassical Italian home that exudes luxury and sophistication. Built by Charles Clayton. Designed by Marc Michaels. The main house boasts over 7,100 sf with 4 bedrooms, 4 full bathrooms, and 3 half bathrooms. The detached Guest House/In-Law is approx. 500 sf, with 1 bedroom, 1 bathroom, two closets, and a wet bar. The detached Catering Room with half (pool) bath is approx. 350 sf with an additional refrigerator, wall-to-wall built-in storage, and is conveniently attached to one of the two-car garages. Enjoy expansive entertaining areas that seamlessly blend indoor and outdoor spaces, offering a grand setting for lavish gatherings. Outfitted with the finest custom finishes, gourmet chef’s kitchen, equipped with top-of-the-line appliances, an oversized island, and large dinette space. Awe-inspiring private courtyard with heated pool and spa, covered porch, outdoor grill, and several separate terraces. Impressive primary suite with office and sitting area has separate his and hers ensuite bathrooms and closets. Stunning two-story closet with office on the second floor and laundry room on first floor. Impressive entertainment/media room with state-of-the-art projector, media equipment and electronic blackout shades. Second story features a spacious loft, 3 bedrooms, 2 full bathrooms, a laundry room and two balconies. Storage is abundant throughout this property. You will find two 2 car garages behind the electronic gated side facing driveway, one garage with a kennel and a Tesla charging station. Experience quintessential Winter Park living in this one-of-a-kind estate that is the epitome of opulence and grandeur. More upgrades than can be mentioned. More architectural detail than can be captured in photographs. This estate is a must see!

Under contract-accepting backup offers. Welcome to luxury living at its finest in this gorgeous END UNIT residence in the Douglas Grand in the heart of downtown Winter Park. This single level three bedroom, three bathroom residence features a gourmet kitchen which opens to the living and dining area, perfect for entertaining and everyday living. The chefs kitchen includes a Sub-Zero refrigerator, Wolf cooktop, Bosch dishwasher, custom granite counters, island with bar seating, and a large walk-in pantry. The spacious primary bedroom with sitting area includes two custom walk-in closets, an en suite bathroom with separate vanities, walk-in shower, and soaking tub. The second primary suite also features a walk-in closet and en suite bathroom with a walk-in shower and tub. The third bedroom/flex room includes a walk-in closet and full bathroom down the hall. Finishes and custom details include beautiful travertine flooring throughout, high volume ceilings, new lighting, crown molding, sound system, newer hot water heater, and Nest thermostat. This residence offers 3 DEEDED PARKING SPACES conveniently located in the gated parking garage along with a DEEDED STORAGE room. From the Douglas Grand, you can easily stroll to renowned Park Avenue and its abundance of restaurants, coffee and wine bars, and boutique shops. Enjoy all downtown Winter Park has to offer including the Winter Park Farmers market, Winter Park Village, art festivals, Rollins College, and an array of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and more.

Under contract-accepting backup offers. NEWLY UPGRADED beautiful home in WINTER PARK's Trinity Bay for ONLY $469,900! That is BELOW the APPRAISED VALUE and is the BEST VALUE in this highly desirable community!!! UPGRADES: NEW FLOORING, QUARTZ COUNTERTOPS, ALL STAINLESS STEEL KITCHEN APPLIANCES, and a NEWER ROOF! There is also a PRIVATE boat ramp to LAKE BURKETT, a PRIVATE spring-fed LAKE with a CERTIFIED SKI COURSE that connects to Lake Marthat. This highly desirable community also offers a residence-only POOL and PLAYGROUND Need more? Look at the huge backyard adjacent to the tranquil WOODED CONSERVATION AREA, a community POOL, a PLAYGROUND, and a LENDING LIBRARY! This incredible two-story 3-bedroom, 2.5-bath residence has dramatic VAULTED CEILINGS in the Foyer, Upstairs Loft, and Great Room (with a wood-burning fireplace). The Kitchen is set up for the entertainer with ENDLESS NEW QUARTZ COUNTERSPACE, ALL STAINLESS STEEL APPLIANCES, and a Dining area with BAY WINDOWS. The lower level also includes a Flex-Office space, and a Family Room, which overlooks or has access to your backyard with your COVERED LANAI, FIRE PIT, PATIO, and the CONSERVATION AREA. The dramatic staircase takes you to the second story with your SPACIOUS OWNER'S SUITE with vaulted ceilings, a soaking tub/shower, a massive vanity with two sinks, tons of cabinets, wrap-around mirrors, a W/C, and a spacious walk-in closet all with NEW LVP FLOORING! Two more bedrooms with NEW LPV flooring and your remodeled main bath with a walk-in shower are just off the 2nd-floor landing. Trinity Bay is zoned in FLORIDA's BEST SCHOOL DISTRICT by Niche.com. It is also next to Trinity Prep, a private 6-12 grade school that Newsweek ranks as Orlando's #1 STEM program. This intimate community is close to shopping, healthcare, and local and national restaurants to suit all tastes. Going anywhere in Orlando is easy with the 417 & 436 just minutes from your new home. Don't miss your chance to make this house your new home. This home is BACK on the MARKET because the BUYER did not perform. It passed all inspections, and the appraisal exceeded the asking price. This is an incredible house that will make a beautiful home!

Welcome to this new 2024 elegant Hampton’s style residence, the epitome of luxury and sophistication. As you enter through the remote-operated gated entrances, a grand circular driveway welcomes you to a private motor court. The stunning two-story foyer features a glass panel staircase wrapping a temperature-controlled wine room and a transparent glass elevator seamlessly connecting all floors, including the expansive third-floor unique attic/multi-purpose room. ** Note: Elegant new RH furnishings package showcased in main living, dining areas as well as entry foyer to accelerate your move-in process enjoying this home seamlessly.* This well thought-out floor plan is ideal for modern living with a spacious open living areas including an oversize gathering room with multiple French doors opening to the lanai, a large dining area with a glass wall viewing a tranquil backyard with sparkling pool and spa. This exquisite property has four-bedroom suites in the main residence, plus a detached pool cabana or a fifth bedroom-guest suite, private hidden office and den, an expansive wonderful upstairs lounge area designed to accommodate media room, flex area with bar or even a billiards table. The gourmet kitchen, ideal for entertaining, boasts two 10-foot-long stone islands, a 60-inch Wolf range, two 36-inch Sub-Zero refrigerator and freezer columns, a warming drawer, a beverage center and a 120-bottle Sub-Zero dual zone wine cooler. There is also a separate pantry-kitchen equipped with a Dacor induction cooktop, convection oven, additional refrigerator, microwave, dishwasher and ample storage cabinetry ideal for catering. The luxurious first level primary suite offers a serene seating area, an all-marble primary bath featuring a glass-enclosed shower with multiple body sprays and shower heads, a soaking tub, and French doors leading to a hidden Zen Garden including a shower and fountain. The second level enjoys three additional bedrooms with en suites, an expansive family lounge, a bar, a full bath and a generous laundry room with a full complement of cabinetry. The third level is accessible via a standard staircase and the elevator, offering almost 800 additional square feet of versatile space, not counted in the square footage quoted in MLS. The outdoor living features and expansive lanai with motorized screens, a gas fireplace, a dining space and a summer kitchen with 54-inch Coyote grill, wood or gas, and separate burner covered by a remote-controlled louvered roof. The detached cabana serves multiple purposes, including a guest suite, fitness room, additional office, game room or nanny quarters, complete with a full bath, mini kitchen and washer/dryer. Luxurious finishes, Andersen windows, 10-foot solid doors, high-end plumbing and electrical fixtures, and Trane HVAC units speak to the quality of construction. The property is surrounded by mature grounds featuring magnolia trees, bamboo and cypress, creating a lush, private meticulously landscaped oasis. Close to ICC, WPRC, Phelps Park/YMCA and Park Avenue.

Remarkable 4 bedroom/2 bathroom home in Winter Park! Formal living & dining areas, separate family room, 3 way split bedroom plan, The PERFECT location convenient to shopping, dining, main roads. WELCOME HOME!

Special financing or closing cost credits available to qualified buyers. 2024 PARADE OF HOMES ORLANDO WINNER - BEST IN CLASS! Don't miss your opportunity to win this extraordinary move-in ready new residence located between the tranquil shores of Lake Spier and Lake Compton, within the exclusive Lake Spier Crossing community in Winter Park. Featuring 10 impeccably designed two-story townhomes, this enclave of contemporary living is crafted by Meridian Homes, Winter Park's premier builder. Expect modern architectural brilliance and thoughtfully planned floor layouts for stylish, hassle-free living. Meticulous attention to detail is evident indoors and outdoors. The kitchen includes state-of-the-art stainless steel appliances and elegant stone countertops, complemented by luxurious hardwood flooring throughout. Convenience is prioritized with in-unit laundry facilities and a two-car garage. Residents of Lake Spier Crossing enjoy exclusive access to three private docks, perfect for paddleboarding, kayaking, or fishing. This exceptional location offers proximity to Lake Baldwin Dog Park and the picturesque Cady Way Trail, ideal for an active outdoor lifestyle. Enjoy the convenience of walking to Downtown Baldwin Park for dining, shopping, and entertainment, or taking a leisurely 10-minute bike ride to the iconic Park Avenue. Access to Winter Park's esteemed school district enhances the allure of this exceptional community.

Under contract-accepting backup offers. Back on Market after renovations. Experience year-round enjoyment with views of the lush Winter Park Pines Golf Club's 6th hole and the calming pond from this well-maintained Winter Park home. New lighting, paint and much more. Situated on a serene cul-de-sac in the sought-after Greenview at the Pines community. This charming 3 bedroom, 2 bath home spans 2,093 square feet with a thoughtfully designed floor plan showcasing two suites, along with an enclosed Florida room - destined to become your favorite retreat the windows are tinted allowing you to enjoy the view of the golf course with complete privacy. Throughout the home, you'll find the convenience of ceiling fans, ample storage solutions, and an irrigation system. No HOA. **Roof replaced in 2017, HVAC updated in 2018** Additional highlights include a cozy breakfast nook, tile flooring, and a convenient 2-car garage, enhancing the overall appeal of this exceptional property. Residents of this community benefit from City of Winter Park utility services and access to esteemed schools including Brookshire Elementary, Glenridge Middle, and Winter Park High. Conveniently located just moments away from downtown Winter Park's vibrant shopping and dining scene, the scenic Cady Way Trail, Crosby Wellness Center, and charming Baldwin Park, Greenview at Winter Pines offers a lifestyle of convenience and leisure. Close to UCF, Full Sail and Rollins College. Don't miss your chance to experience this captivating home firsthand - schedule your private showing today.

One or more photo(s) has been virtually staged. Welcome to your new home in the heart of Winter Park! This spacious condo offers a blend of comfort and convenience, ideal for those seeking an active and vibrant 55+ community. Here’s what makes this property truly special: Key Features: Spacious Living: Enjoy the generous space of two large bedrooms, perfect for relaxation and comfort. Freshly Painted: The entire condo has been freshly painted, giving it a bright and inviting atmosphere. Elegant Touches: Plantation shutters in the bedrooms add a touch of elegance and provide excellent light control and privacy. Assigned Parking: You’ll have the convenience of assigned parking spots, ensuring easy access to your home. Community Pool: Take a dip in the community pool, a perfect spot for socializing and staying active. Highly Sought After Location: Nestled in one of Winter Park’s most desirable areas, this condo is close to everything you need. Nearby Amenities: Shopping: Conveniently close to a variety of shopping options for all your daily needs. Hannibal Square: Explore the charm of Hannibal Square with its unique shops, restaurants, and cultural events. Hospitals: Proximity to top-notch medical facilities ensures peace of mind and quick access to healthcare. Orlando Museum of Art: Immerse yourself in culture and creativity at the nearby Orlando Museum of Art. Park Ave: Stroll down Park Ave, known for its beautiful scenery, boutique shops, and dining experiences. Flea Market: Discover hidden treasures and enjoy the lively atmosphere of the local flea market. Rollins College: Engage in community events and enjoy the beautiful campus of Rollins College. Azalea Tennis Center: Stay active with the excellent facilities at the Azalea Tennis Center. This condo is not just a home; it’s a lifestyle. Whether you’re looking to relax, stay active, or enjoy the rich cultural and social offerings of Winter Park, this property provides it all. Don’t miss the opportunity to be part of this vibrant 55+ community. Contact us today to schedule a viewing and make this wonderful condo your new home!

LOCATION, LOCATION, LOCATION! Discover your dream home in the heart of Winter Park, nestled on a quiet dead-end street. This beautifully updated property boasts: - Seller Will Provide Home Warranty - Ceramic tile flooring throughout - Both bathrooms have been updated - Spacious closets and plenty of storage - Bright eat-in kitchen with stainless steel appliances and sliding glass doors leading to a private patio - Freshly painted interior and Exterior - Ceiling fans in every room for added comfort The expansive backyard is fully fenced, perfect for family fun and entertainment. The converted garage offers a possibility as a fourth bedroom or can be converted back to a one-car garage. Enjoy the convenience of no HOA fees! Prime location puts you minutes from Winter Park Village, Park Avenue, Sun Rail Station, Rollins College, shopping, restaurants, entertainment venues, and public golf courses. Easy access to Orlando International Airport and Downtown Orlando via major highways. Make this charming home yours today and experience the best of Winter Park living at an amazing price.

Welcome to your charming two-story condominium located on the second floor in Winter Park! This delightful 3-bedroom, 2-bathroom condo offers 1,300 sqft of comfortable living space, perfect for anyone seeking a serene and convenient lifestyle. Built in 1974, this residence boasts a timeless design with modern comforts. The exterior features classic Board & Batten siding, while the interior walls are lined with smooth drywall, creating a cozy and inviting atmosphere. The open floor plan seamlessly connects the living, dining, and kitchen areas, making it ideal for entertaining guests or enjoying quiet evenings at home. The main level includes a spacious living area with abundant natural light, a well-appointed kitchen, and a dining area perfect for family meals. The second level houses three generously sized bedrooms and two full bathrooms, providing ample space for relaxation and privacy. Located in a desirable community, this condo offers access to a variety of amenities and is just minutes away from shopping, dining, and entertainment options. Enjoy the convenience of being close to parks, schools, and major highways, making your daily commute a breeze. Don’t miss the opportunity to make this wonderful condo your new home. Schedule a showing today and experience the best of Winter Park living!

**Spacious and Rare Find: Below Market Price in a Sought-After Community** This expansive condo, the largest model in the development, is freshly painted and features a newer roof installed in 2022, along with brand-new window blinds. It’s the perfect canvas, waiting for your personal touch with flooring choices for the stairs and master bedroom. Offered AS-IS due to the need for flooring, this property is priced to sell well below the current community square footage price. Inside, every bedroom boasts its own bathroom, with two luxurious master suites offering ultimate comfort and privacy. The master bath upstairs also benefits from new skylights installed during the roof replacement, filling the space with natural light. Tile flooring flows throughout the rest of the home, enhancing the open, airy feel. Step outside to your private backyard, a fantastic space for entertaining or simply enjoying the serene surroundings. This condo is not only spacious but also beautifully designed, offering a rare opportunity in a quiet, quaint community with a beautiful pool and friendly neighbors. Located just minutes from Winter Park’s premier shopping, dining, and lakes, and with low HOA dues, this is a must-see property. Act fast—properties like this, especially at this price, don’t last long!