Winter Park Real Estate Search

Winter Park Homes for Sale

In Orange County, Florida, in the Orlando Metro Area, the charming community of Winter Park has much to offer prospective homebuyers. Winter Park has roughly thirty thousand residents and is well-known for its glistening lakes, lush mature trees, and quaint brick-lined streets. This well-established community also boasts a rich heritage and long history, initially chartered in 1887. Today it sits just north of Orlando, thereby offering proximity to a long list of big-city attractions, amenities, and services. Simultaneously, Winter Park offers a relaxed, laid-back lifestyle and a variety of local high-end restaurants, boutique shopping, and other upscale amenities, particularly along Park Avenue but also in smaller pockets of the area. 

Winter Park is the ideal destination for an afternoon promenade with an extensive collection of award-winning restaurants and frequent festivals and events. Among the most popular Winter Park festivities are the Florida Film Festival, Winter Park Sidewalk Art Festival, the Bach Festival Society of Winter Park, and the Winter Park Autumn Art Festival. Additionally, the community is home to the Winter Park Historical Museum and the second oldest golf club in Central Florida. 

Homes for sale in Winter Park are equally desirable and diverse and are located in appealing neighborhoods and subdivisions like Orwin Manor, Northwood Circle, College Quarter, Windsong, Hannibal Square, Green Oaks, and Plymouth Apartments. Real estate in Winter Park consists of an array of semi-detached, attached, and detached homes of many ages, architectural styles, sizes, and floor plans. If you would like specific details about available properties in Winter Park, Florida, please connect with us today, and we will happily help you with your Winter Park home search.

Our website features the best Winter Park real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

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Newest Winter Park Homes and Condos for Sale

4 Beds 2.5 Baths Cypress Reserve SubDv. 32792 Zip Code
Welcome to your dream home in the exclusive, gated community of Cypress Reserve in Winter Park! This stunning 4 bedroom, 2.5 bath pool home is perfectly located for your convenience, just minutes from Park Avenue in downtown Winter Park and a variety of restaurants, shops and schools such as Trinity Prep and the Master's Academy. The light and open floorplan features volume and vaulted ceilings, skylights, a ton of natural light, and luxurious tile and engineered hardwood floors that make it feel like a model home. The heart of the home is the beautiful chef's kitchen, complete with a Blanco double sink, 42" solid wood, raised and stained cabinetry, granite counters, stainless appliances, and a built-in wine cooler. It's open to the family room, which is highlighted by a fireplace with a striking antique slate mantle and a bluestone hearth - perfect for cozy gatherings. The smart split-floor plan design includes carpet in the secondary bedrooms, one of which features a coffered ceiling with hand-carved wood accents. The spacious master bedroom includes a sitting area and two organizer walk-in closets, and the remodeled master bath is like your own personal spa with a contemporary garden tub, large shower and dual sinks with Carrera marble counters. But the real showstopper is the stunning pool area, complete with stone work and a waterfall. It's perfect for entertaining or just relaxing with family and friends. And if you need some relaxation, there's a peaceful garden area in the back as well. This move-in ready home has it all, including a newer roof, resurfaced pool, double-pane windows, gutters, newer water heater, exterior paint, and interior paint. Plus, the oversized garage features a full 3rd bay that's perfect for a workshop or storage. Don't miss your chance to make this great family home your own - schedule a private tour today!

5333 Cypress Reserve Place, Winter Park

4 Beds 4.5 Baths Comstock Park SubDv. 32789 Zip Code
Perched on a hill on a corner lot, nestled between Sylvan and Bonita along the brick streets of Winter Park, this home has so much to offer. With a privacy wall along Maiden Lane, this home truly feels like a secluded oasis. Beyond the 3-car garage, you'll be greeted by a charming gated porch that leads into a spacious living area filled with natural light, where the French doors lead to a screened patio and a resort-style pool that will take your breath away. The dining room, with tall, graceful windows on one end, leads to the kitchen, offering stone counters, a cooking island, 2nd prep sink, wine refrigerator, double built-in ovens, a water purifier, and a dinette with a large bay window. The breakfast bar offers additional seating, and overlooks the family room, with vaulted ceilings and a wood-burning fireplace, plus additional French doors to access the screened-in patio. Off the kitchen/living combo, there is a full bath that also services the pool. The spacious downstairs master suite, with plantation shutters and French doors to the screened patio, features a double-sided fireplace separating the bedroom from the master bath, with a large soaking tub, glass shower, private water closet with a bidet, and large walk-in closet. A laundry room with a utility sink and laundry chute, and a front powder bath for guests, complete the 1st floor. Upstairs includes 3 bedrooms, all with walk-in closets, 2 full bathrooms, and a balcony overlooking the sprawling backyard. Outside, you’ll enjoy lush landscaping and the soothing sound of the pool fountains! The large pool deck offers lounging, with additional seating and dining space within the screened patio. Surrounded by A-rated schools, convenient stores such as Walgreens, Publix, & Sprouts, the YMCA, the AdventHealth Hospital, Phelps Park, and around the corner from Park Avenue – this location cannot be beat!

600 Maiden Lane, Winter Park

5 Beds 4.5 Baths Kenilworth Shores Section Seven SubDv. 32792 Zip Code
BETTER THAN NEW AND READY FOR YOU! BUILT IN 2021!! Designed and built by Winter Park architect and building contractor, Stevens, Inc., this CUSTOM CRAFTSMAN style home brings so much character from the wood and tile floors to the beautiful tongue and groove clear pine ceilings. This stunning home boasts 5 bedrooms with 4 full baths and one-half bath but is designed with FLEXIBILTY to utilize them as an office and a bonus room depending on the family’s living needs. The house is bright and inviting with huge living space on the first floor with wood flooring and spacious primary suite and second bedroom/office downstairs. Gourmet kitchen offers custom cabinetry, over-sized island, tile backsplash, upgraded Monogram appliance package and an large walk-in pantry. Private primary suite boasts a large en-suite bath which includes a soaking tub, shower stall with 6 function Delta faucets, 2 WALK-IN closets, double sinks, and solid wood cabinets. The oversized laundry room includes a full-sized sink. Second floor offers flexibility with 3 bedrooms/2 baths featuring a 12x17 bedroom which could be used as a bonus room. Be sure to read the Special Features Sheet in the Attachments for more specific information. Optional HOA gives you access to Lake Berry!! Conveniently located minutes to Park Avenue, Downtown Orlando, top-rated Winter Park schools, and numerous dining options, parks, gardens, museums, golf courses, and shopping. No need to build!!! This gorgeous, immaculate, well-appointed Winter Park Home can be yours today!

1918 Summerfield Road, Winter Park