The median home value in Winter Park, FL is $209,300.
the county median home value of $226,800.
The national median home value is $152,300.
The average price of homes sold in Winter Park, FL is $209,300.
Approximately 56.63% of Winter Park homes are owned,
compared to 31.93% rented, while
11.43% are vacant.
Winter Park real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you see a property you’re interested in, contact a Winter Park real estate agent to arrange a tour today! Learn more about Winter Park Real Estate.
As beautiful inside as it is outside, this magnificent one-of-a-kind lakefront estate is located in the Gated Estate Section of Windsong, one of Winter Park's most desirable addresses. This custom one-owner home was built in 2005 by award-winning Rial Jones and designed by Bernie Johnson. The 2+ acre estate is surrounded by water on both sides, with Lake Mizell in the front and Lake Virginia in the rear, with the back illuminated at night by Rollins College and downtown Orlando. The floor plan is masterfully laid out with 6 bedroom suites plus an office suite, media room, and many bonus areas. Features include ceilings artfully designed with wood beams and exquisite detail; coquina baseboards; Venetian plaster and sueded walls; professionally organized closets; custom carpentry; travertine and distressed wood floors; and meticulous detail and top of the line amenities in every room. Gourmet kitchen has 6 burner gas stove, double ovens, uniquely designed wood burning grill, 2 dishwashers, and adjacent butler's pantry with 3rd dishwasher plus attached wine room. Upstairs and downstairs laundry. Downstairs master suite overlooks lake and has gas fireplace, attached sitting room, and walk-in closet "rooms", plus His & Her sinks and toilet rooms. Four themed bedroom suites upstairs also include attached offices for each. Backyard includes pool with water features, 1260sf covered lanai with gas fireplace and summer kitchen, all overlooking lush lawn and lake. Truly one of the finest homes in Central Florida.
ELEGANT LAKEFRONT ESTATE in the heart of downtown Winter Park! This magnificent showplace estate home is located on 3 lush acres with sweeping views of Lake Osceola and easy walking distance to Park Avenue. The main residence, which has 6,372 sq. ft., was originally built in 1930, totally renovated in 1994 and then had major additional updating in 2005. New embellishments include remodeled kitchen, covered walkway from the garage to the main house, all new landscaping and irrigation, new boat dock, new tennis court, 6 new AC units including ductwork, new windows in main house, new alarm system and much much more. This one-of-a-kind estate includes a fabulous 1391 square foot 3 bedroom 3 bath guest house with living room and kitchen. Additionally, there is a 1 bedroom 1 bath caretaker's cottage with 582 square feet. Numerous features include koi pond, 3 car garage, tennis court, Jacuzzi, dock with boat house, large dry basement. This luxurious gated showplace is a dream come true for the right buyer. It retains the old world feel of the 1930's with all the comforts of the new millennium.
This Italian inspired waterfront estate is located on Lake Mizell, on the Winter Park chain of lakes in the exclusive Windsong community. Situated on 1+ Ac boasting 200ft of lake frontage w/magnificent views and sunsets, this home radiates splendor while still reflecting warmth and elegance. The residence was featured in Dreamhomes Florida, an exclusive showcase of Florida's finest Architects, Designers, and Builders. This custom one-owner home has beautiful architectural features and one of a kind exquisite details including groin vaulted, barreled, and gold leaf and hand painted ceilings, Venetian plaster and custom wall coverings, custom cabinetry, two story custom wood master closet and professionally organized secondary closets. 5 custom stone fireplaces. Travertine, marble and wood floors. Gourmet kitchen has 6 burner gas stove, double ovens, island, bar, walk-in pantry w/second refrigerator, breakfast nook, brick courtyard w/fountain and kitchen office. Wine room and wet bar off living and dining room, upstairs/downstairs family rooms, entertainment/music room w/full bar, bonus room, 5 bedroom suites, luxurious downstairs master bedroom w/fireplace and sitting room. Covered outdoor living area w/summer kitchen, custom disappearing edge pool. Outdoor spa, fountain, outdoor wood burning fireplace. Covered boat dock, and waters ports area w/jet ski platform and electric boat lift. Other features include 40KW natural gas generator, lightning suppression system, internet based camera security system.
Grand lakefront pool home with breathtaking views of Lake Maitland. Situated on a prestigious Winter Park street, this six bedroom, six & one half bath home is within walking distance to downtown Park Ave. The open and welcoming foyer & living room features soaring 26 foot ceilings. The dramatic dining room offers awe-inspiring floor to ceiling glass wall with lake views. Expansive chef's dream kitchen featuring top-of-the-line appliances, granite counters & gigantic island that seats 6, all open to the large breakfast nook. Amazing lake views from almost every room & gorgeous 5" Brazilian Epe' wood floors throughout the main living areas. Glamorous master retreat with custom marble wood burning fireplace, sitting room with French doors leading to the pool and lake, "Wow-effect" closet & bathroom with dual sinks, Jacuzzi tub, separate toilet/bidet room & shower. Secondary bedroom on the master wing currently being used as an exercise/hobby room. Living quarters upstairs including a large playroom/media room with full bathroom; four bedrooms each with en-suite bathroom, walk-in closet & sliding doors leading to the sprawling balcony. Covered lanai and sun drenched pool are the perfect setting for watching sunsets over Lake Maitland. Enjoy boating on the largest lake on the Winter Park Chain from your dock featuring a storage room, 2 floating docks & electric hoist & remote controlled boat cover. Too many features to list! Please see attached Feature Sheet for additional features.
Exquisite, custom designed lakefront estate on the Winter Park Chain of Lakes. Inspired by Anglo-Caribbean architecture, this stunning four bedroom, three bath home combines indoor/outdoor living and inspires elegance beneath its cathedral ceilings and exposed trusses. Designer gourmet kitchen features custom cabinetry with Carrara Marble counter tops, Viking Professional appliances, Sub-Zero refrigerator, dual dishwashers, and a large walk-in pantry with felt lined silver sideboard and full china cabinet. Private staircase leads to master retreat with breathtaking lake views, large sitting area, and his and her dressing rooms. Master bath is adorned in Akdo marble mosaic tiles and appointed with walk-in shower and soaking tub. Guest suite with full bath is located downstairs, with two additional bedrooms and full bath on second floor. Travertine tile and Brazilian Walnut floors are installed throughout the home and exterior entertainment areas where an outdoor kitchen and fireplace add to the tranquil surroundings of lakefront living. No expense was spared in the design and creation of this magnificent home. Professional landscaping, paved motor court, oversized 3-car garage, privacy gate, security system, pre-engineered elevator capabilities, and original designer touches throughout make this home one-of-a-kind and a truly uplifting place to call home.
Stunning Winter Park Chain-of-Lakes estate. Only a short walk from Park Avenue, this five-bedroom pool home was custom built in 2004 with the finest materials and to the highest of standards and finishes. Brazilian Walnut and natural stone flooring is throughout the entire home. First floor amenities include a formal living room with fireplace, formal dining, a spectacular center-island kitchen overlooking the family room with stone fireplace, paneled library with fireplace and a gorgeous master suite with breath-taking views of Lake Osceola. The second floor features three large bedrooms, three full baths, and laundry. The fourth bedroom, also with a full bath, currently serves as a large playroom. The estate's lower level features large-screen media, billiards, wet bar, and private office. Windows throughout the lower level provide plenty of natural light! Outdoors is like you've never seen before. Gas lamps, a large pool, fountains, English gardens, motor court with three car garage and one of the longest and most beautiful views on the Winter Park Chain. Detailed Features List is available upon request.
Chain of Lakes Executive Estate with Amazing Guest House nestled in the Heart of Olde Winter Park. Sprawling property offers panoramic views of beautiful Lake Maitland. Elegant home remodeled in 2001 boasts a spectacular Master suite with His & Her Bathrooms and walk-in closets, soaring ceilings in Foyer & Formal Rooms, smartly appointed Gourmet Kitchen with cozy breakfast nook, Family Room with exquisite millwork, built-ins & gas fireplace. The 26x17 downstairs bonus room perfect for your home office/library, game room or In-Law Suite. PLUS incredible Guest House above detached 3 Car Garage includes vaulted ceilings, large Bedroom/Bath and full Kitchen. Stunning back yard oasis complimented with manicured landscaping, amazing patio for entertaining, stone enhanced waterfront & boat dock with hoist. Walk to Park Avenue from this serene cul-de-sac location. Lakefront Living at it's Finest!
Winter Park lake front living at its finest. Elegant lake front estate on triple lot with private clay tennis court! Located in the sought-after Windsong Northshore area, this fabulous home is surrounded by grandfather oaks on a brick- lined street with tranquil pond and fountain across the street. This two story Palm Beach style home on 1 acre w/196' of lake frontage is equipped with a clay hydro tennis court, oversized pool, covered dock w/electric hoist. The prime Winter Park location on a quiet street within walking distance to Park Avenue shops and restaurants. The next homeowner will love the private tennis court. Huge bay windows grace the master and living rooms with marble fireplaces, allowing panoramic views and sunsets on Lake Mizell. Wrought Iron spiral exterior staircase leads from pool to second floor balcony. Two bedrooms downstairs en-suite would make perfect nanny quarters or in-law suite. Fabulous unique bamboo style gourmet kitchen w/gas range and double ovens, built-in fridge w/separate large casual eating area overlooking lake. Built-in bookshelves in library/computer room. Several bedrooms have built-in furniture. This is truly a "one of a kind " Winter Park chain of lakes residence.
Coastal Living in Winter Park, Enjoy this 'Santa Barbara' style home with expansive rooms detailed with river washed wood beams, Peruvian travertine and a reclaimed terra cotta roof.This fully furnished show place by Montanna & Associates boasts 5 bedrooms, includes 2 master suites, 5 full and 2 half baths, pool with fire pots, outdoor cigar terrace adjoining the gentlemen's lounge with theatre, and an extraordinary kitchen with every amenity. This fully gated estate is situated on a .58 acre lot, and offers a 3 car garage and extended parking space on a Chinese quartzite driveway. There is a Lutron lighting system, a 1200 bottle wine room, Hurd windows and the home is prewired foran emergency generator with a load management panel. Materials include onyx, Peruvian travertine, granite, copper clad tub, and casement windows. The master suite has a beautiful view of the gardens and the master bath features a rain shower, warming drawer for towels, and an oversized closet with organizers. A hidden passage to the office completes the master wing. A second master suite is located upstairs along with 3 guest suites; all complete with crown moulding, niches, and beautifully detailed baths. Outdoor living includes a pool with water deck, swim shelf and fire pots. There is ample room for pets. Enjoy the evening in the outdoor kitchen, on the cigar terrace or around the fire pit all within walking distance of Park Ave.
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