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Winter Park FL Real Estate & Homes For Sale

549 Properties Found

The median home value in Winter Park, FL is $226,800. This is higher than the county median home value of $111,200. The national median home value is $152,300. The average price of homes sold in Winter Park, FL is $226,800. Approximately 58.04% of Winter Park homes are owned, compared to 31.7% rented, while 10.26% 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.


1 - 10 of 549 Properties Displayed
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$6,995,000

1016 Genius Dr Winter Park, FL 32789

Beds:
6
Baths:
9.00
Sq.Ft.:
10,314
Status:
Active
MLS#:
O5162608
Type:
Single Family
Subdivision:
Windsong Ests Sec 1
Lot size:
2.2 Acres
Year built:
2005
A broker reciprocity listing Listing Provided Courtesy Of: FANNIE HILLMAN & ASSOCIATES
View additional info

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.

$6,950,000

802 Georgia Ave Winter Park, FL 32789

Beds:
4
Baths:
5.00
Sq.Ft.:
8,345
Status:
Active
MLS#:
O5113660
Type:
Single Family
Subdivision:
Winter Park Old Town
Lot size:
3.25 Acres
Year built:
1930
A broker reciprocity listing Listing Provided Courtesy Of: FANNIE HILLMAN & ASSOCIATES
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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.

$6,675,000

324 N Interlachen Ave Winter Park, FL 32789

Beds:
5
Baths:
7.00
Sq.Ft.:
8,738
Status:
Active
MLS#:
O5217018
Type:
Single Family
Subdivision:
Town Of Winter Park
Lot size:
2.13 Acres
Year built:
1925
A broker reciprocity listing Listing Provided Courtesy Of: FANNIE HILLMAN & ASSOCIATES
View additional info

A once in a lifetime opportunity to own a 1925 historic estate on one of Winter Park's most beautiful streets, steps to downtown Park Avenue. This property sits on over 2 acres with amazing views of Lake Osceola and professionally landscaped grounds. Amenities include original wood floors, original staircase & banister, chandeliers, crown molding, high ceilings, wood burning fireplaces & French doors. Living spaces are large and accomdating with great flow for entertaining. Updated kitchen. Billiard room, office, music room, den/family room & powder bath are also located on the main level of this estate. Second floor features an elegant master retreat with private sun deck, screened porch & updated bath as well as 4 additional spacious bedrooms, three baths, an office & a hobby room. Third floor features a huge bonus room. The backyard feels like a luxury spa with amazing lake views, cabana & summer kitchen, screened lanai, and newly renovated heated pool/spa. Expansive lake frontage is complete with volleyball court & boat dock.

$5,850,000

970 Via Lugano Winter Park, FL 32789

Beds:
6
Baths:
9.00
Sq.Ft.:
10,190
Status:
Active
MLS#:
O5220307
Type:
Single Family
Subdivision:
Woodmere Terr Rep
Lot size:
1.01 Acres
Year built:
2000
A broker reciprocity listing Listing Provided Courtesy Of: COLDWELL BANKER RESIDENTIAL RE
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Premier lakefront estate in the heart of the Vias on Lake Maitland and built by Charles Clayton Construction... 1st time offered for sale! This Winter Park Chain of Lakes estate takes advantage of the elevated topography. Inspired by the magnificent transitional estate homes of the Northeast, this home boasts panoramic views of Lake Maitland with 120' of water frontage on over an acre lot. There are 5 en suite bedrooms, 8 baths in the main house, plus a detached 1 bedroom/1 bath full guest apartment over the three car garage. Downstairs commences with a grand entry overlooking the lake thru an impressive 2-story living & music room, guest suite, gentleman's library, dining room, butler's pantry, and an elegant chef's kitchen open to the gathering room and breakfast room with 2-story beamed ceilings. Upstairs is highlighted by an expansive private master retreat with luxurious bath & dressing area, along with a wonderful "tree-top" sitting room to enjoy the elevated views of the lake. Additionally, you will find 3 more bedroom suites, large bonus room, and laundry room. Outdoor living spaces include a 2-story screened in sitting room, multiple covered lanais around the pool area, summer kitchen, and a beautiful winding path down to a boat house with storage room. There are top quality finishes inside and out including Pella windows & doors, oak hardwood floors, extensive trim & detailed craftsmanship, and Monier tile roof. Walking distance to the WP Racquet Club and Park Avenue!

$5,500,000

N 909 N Wymore Rd Rd Winter Park, FL 32789

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
O5152153
Type:
General Commercial
Lot size:
1.21 Acres
A broker reciprocity listing Listing Provided Courtesy Of: PRIMESTATE REALTY, INC.
View additional info

GOOD LOCATION, GOOD PROPERTY IN WINTER PARK, LICENSE FOR 95 BEDS. ALF, UPDATED ROOF, UPDATED ELECTRIC, UPDATED FIRE ALARM SYSTEM, UPDATED PLUMBING, UPDATED FLOORING.

$3,950,000

730 Via Lugano Winter Park, FL 32789

Beds:
5
Baths:
9.00
Sq.Ft.:
6,628
Status:
Active
MLS#:
O5206584
Type:
Single Family
Subdivision:
Sicilian Shores
Lot size:
0.66 Acres
Year built:
2000
A broker reciprocity listing Listing Provided Courtesy Of: COLDWELL BANKER RESIDENTIAL RE
View additional info

Magnificent Winter Park Mediterranean lakefront located in premier Via's location on the Chain of 6 Lakes... Present owner completely renovated and tastefully upgraded this home to a modern Mediterranean style with Charles Clayton Construction & Signature Landscape Contractors... This lakefront home is situated on an oversized double lot (apprx. ? acre property) with an estimated 125 ft on Lake Maitland. Top quality features throughout this spacious entertaining home with a wide open floor plan, soaring ceilings, picture windows, extensive wall & ceiling details, and new ipad home automation system with Lutron lighting, security cameras & surround sound... Impressive 2-story grand foyer with handsome winding staircase, luxurious downstairs master retreat with sitting area and his/her baths & closets, and 1st floor guest suite or library with built-ins & private bath... Gourmet island kitchen w/ separate bar area for entertaining open to the lakeside gathering room... Upstairs includes a separate bonus/flex room, open loft area and 3 add'l bedroom suites... The outdoor living offers tranquil scenic lake views, a private boathouse, expansive privately fenced lawn with lush landscaping, brick patio & wonderful screened lanai along with towering majestic Cypress trees... The property boasts four garages with a motor court and fabulous elegant palms with picturesque landscaping... This lakefront property is meticulously maintained in a "like new" condition for your most discriminating buyers...

$3,645,000

1316 Green Cove Rd Winter Park, FL 32789

Beds:
6
Baths:
7.00
Sq.Ft.:
6,763
Status:
Active
MLS#:
O5189634
Type:
Single Family
Subdivision:
Camwood
Lot size:
0.7 Acres
Year built:
1991
A broker reciprocity listing Listing Provided Courtesy Of: KELLY PRICE & COMPANY LLC
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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 Ipe 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.

$3,399,000

110 Osceola Ct Winter Park, FL 32789

Beds:
5
Baths:
6.00
Sq.Ft.:
6,713
Status:
Active
MLS#:
O4853377
Type:
Single Family
Subdivision:
Osceola Court
Lot size:
0.38 Acres
Year built:
2004
A broker reciprocity listing Listing Provided Courtesy Of: KELLY PRICE & COMPANY LLC
View additional info

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.

$3,250,000

1400 N New York Ave Winter Park, FL 32789

Beds:
4
Baths:
6.00
Sq.Ft.:
5,656
Status:
NEW LISTING
MLS#:
O5221620
Type:
Single Family
Subdivision:
Metes And Bounds
Lot size:
1.04 Acres
Year built:
1977
A broker reciprocity listing Listing Provided Courtesy Of: FANNIE HILLMAN & ASSOCIATES
View additional info

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!

$3,220,000

405 Lakewood Dr Winter Park, FL 32789

Beds:
4
Baths:
3.00
Sq.Ft.:
4,208
Status:
Active
MLS#:
O5197207
Type:
Single Family
Subdivision:
Osceola Shores
Lot size:
1.21 Acres
Year built:
2008
A broker reciprocity listing Listing Provided Courtesy Of: KELLY PRICE & COMPANY LLC
View additional info

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.

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All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.
Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Copyright 2011, My Florida Regional MLS

Winter Park FL Real Estate Listings Provided By:

Real Living Good Neighbor Realty
990 N. SR 434, Suite 1132
Altamonte Springs, FL 32714
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