Winter Park, Florida MLS listings - Homes for Sale

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Homes For Sale » Florida » Orange county » Winter Park
$6,995,000
1016 Genius Drive
6 bed / 7.2 bath Single Family Home
MLS #O5162608
10,314 sq. ft.
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…
$3,250,000
1316 Green Cove Road
6 bed / 7 bath Single Family Home
MLS #O5338507
6,763 sq. ft.
Winter Park, FL 32789
Grand lakefront pool home with breathtaking views of Lake Maitland. Situated on a prestigious Winter Park street, this six bedroom, six and one half bath home is within walking distance to downtown Park Ave. The open…
The Ellno Willo
$5,695,000
147 Virginia Drive
5 bed / 8 bath Single Family Home
MLS #O5365962
7,800 sq. ft.
Winter Park, FL 32789
Majestic Winter Park Estate on 1.59 acres of pristine lakefront property. Panoramic views of Lake Virginia from every corner of this stunning home. Private driveway with electronic gate, motor court, four car garage,…
Cloister Grove
$1,950,000
1270 Via Salerno
4 bed / 4 bath Single Family Home
MLS #G4814923
6,138 sq. ft.
Winter Park, FL 32789
MOTIVATED SELLER, SELLERS CAN VACATE WITH IN A WEEK. Located in the “Via’s” Winter Park neighborhood, this Lake Front home offers panoramic views of Lake Knowles Circle. This 6,000 sq. ft. FRESHLY PAINTED interior…
Robert Dhu Macdonald Park
$2,800,000
1020 N Park Avenue
5 bed / 8 bath Single Family Home
MLS #O5380685
8,342 sq. ft.
Winter Park, FL 32789
Your opportunity to own a Masterpiece on the most prestigious street in Central Florida! This Classic Estate offers elegance, luxury and entertainment in the heart of desired Winter Park. With just a short walk…
Thomas M Henkels Add
$3,999,999
440 Henkel Circle
5 bed / 7 bath Single Family Home
MLS #O5382686
6,113 sq. ft.
Winter Park, FL 32789
Located in the heart of Winter Park within close distance to Park Ave, Winner of the 2007 Parade of homes, this custom home will not disappoint you. This 1.25 acre estate boasts over 200 feet of water front on Lake…
South Interlachen Place
$2,074,000
125 S Interlachen Avenue #5
2 bed / 5 bath Town Home
MLS #O5389629
3,244 sq. ft.
Winter Park, FL 32789
Under Construction. Only two residences remain! Your opportunity to own unprecedented luxury in the most exclusive area of Winter Park has arrived. South Interlachen Place is around the corner from world famous Park…
Windermere Woods
$4,250,000
1000 Genius Drive
5 bed / 7 bath Single Family Home
MLS #O5398017
8,157 sq. ft.
Winter Park, FL 32789
Welcome to 1000 Genius Drive……..a piece of Winter Park history! This Mediterranean lakefront estate on 1.89 acres was originally designed and constructed in 1925 by a group of Winter Park league of businessmen to be…
Adair Place
$3,500,000
2150 Via Tuscany
7 bed / 10 bath Single Family Home
MLS #O5398109
7,670 sq. ft.
Winter Park, FL 32789
Timeless perfection encompasses every room of this stunning Winter Park estate. Custom built by Charles Clayton, this seven bedroom, seven bath home exudes character and charm throughout and includes features so seldom…
Windsong Preserve Point 43/76
$3,350,000
MLS #O5401470
1.39 acres
Winter Park, FL 32789
Rare opportunity to build your dream home in the heart of Winter Park. This waterfront property is in the desirable Windsong community and on the Winter Park Chain of Lakes.
Preserve Point/Windsong
$1,995,000
1661 Chase Landing Way
6 bed / 6 bath Single Family Home
MLS #O5401777
4,976 sq. ft.
Winter Park, FL 32789
Windsong lakefront... this is your chance to own a recently renovated "like new" traditional style lakefront home at the end of a quiet cul-de-sac in Winter Park’s prestigious Windsong neighborhood. Surrounded by…
Villa Siena
$1,850,000
315 E New England Avenue #2
3 bed / 4 bath Condo
MLS #O5404839
3,276 sq. ft.
Winter Park, FL 32789
A block from Winter Park's famed Park Ave., The Residences at Villa Siena combines the convenience of city living with the privilege of estate luxury, packaged in a classic architecture facade reminiscent of old…
$1,795,000
210 E Canton Avenue
3 bed / 3 bath Town Home
MLS #O5425778
4,100 sq. ft.
Winter Park, FL 32789
Walk to Park Avenue. This prime luxury townhouse has amazing features with stylish retro touches in the most desirable location of Winter Park. Private elevator within the residence, private terraces, balconies and a…
Valencia Terrace
$2,265,000
1101 N Park Avenue
4 bed / 5 bath Single Family Home
MLS #O5424059
4,826 sq. ft.
Winter Park, FL 32789
Pre-Construction. To be built. Wonderful opportunity to customize details on this stunning Modern Mediterranean only footsteps from Park Avenue shops & restaurants… 6553 SF estate thoughtfully designed for gracious…
Sicilian Shores
$2,850,000
711 Pinetree Road
4 bed / 5 bath Single Family Home
MLS #O5427789
4,770 sq. ft.
Winter Park, FL 32789
Gorgeous Lake Maitland one-owner custom home on premier street in the heart of the Vias. Situated on over 1/2 acre, this home boasts abundant extras throughout. Huge kitchen with granite counters, great storage, sunny…
Woodcrest Unit 8
$1,800,000
MLS #O5361370
10.13 acres
Winter Park, FL 32792
3 parcels totaling 10+ acres in winter park - 470 feet of road frontage on howell branch road that will offer plenty of exposure in the desirable area. builders are selling out their communities in less than 6 months…
$5,800,000
4037 Meric Drive
Commercial Property
MLS #A10114162
Winter Park, FL 32792
Excellent office and potentially warehouse investment property. Already produces 9% +/- Cap Rate based upon the asking price and adjusted for reassessed taxes and insurances. With under market rents and 7,200 SF of…
Green Oaks Rep 02
$5,095,000
1941 Legion Drive
6 bed / 9 bath Single Family Home
MLS #O5427192
10,493 sq. ft.
LUXURIOUS LAKE MAITLAND ESTATE! This Winter Park Chain of Lakes Custom 5 car garage home has panoramic views of Lk. Maitland w/ 175' of water frontage on 1.09 acres. This magnificient home has it ALL! The living &…
The Residences At Winter Park
$2,095,000
300 S Interlachen Avenue #504
4 bed / 4 bath Condo
MLS #O5428287
4,090 sq. ft.
Winter Park, FL 32789
Distinguished, upscale living at The Residences at Winter Park. Stunning four bedroom unit on the fifth floor is the epitome of luxurious living with panoramic views of downtown Winter Park and Lake Virginia. By far…
Boiley Green Sub
$4,300,000
1830 Gipson Green Lane
5 bed / 7 bath Single Family Home
MLS #O5427054
6,850 sq. ft.
Winter Park, FL 32789
LUXURY LAKEFRONT LIVING! Privately nestled on Winter Park's Chain of Lakes, this Spectacular Home w/ gated entrance, has it all! Entirely remodeled w/award-winning interior designer, Betsy Godfrey, no attention to…
Douglas Grand Winter Park Residential
$1,699,000
102 S Virginia Avenue #110
3 bed / 4 bath Condo
MLS #O5432184
3,778 sq. ft.
Winter Park, FL 32789
Central Florida's most distinctive, historic and established in-town living experiences. Welcome your guest directly from your own front door located on Virginia Avenue. Sit on your corner covered porch to read the…
Preserve Point/Windsong
$3,450,000
MLS #O5429362
1.48 acres
Winter Park, FL 32789
Located in Windsong on a quiet cul-de-sac only 10 minutes from Downtown Orlando. This lot faces West and overlooks Rollins College. The total square footage of the lot is 64,407 sq. ft. (1.48 acres). There are 5 very…
Osceola Shores Sec 03
$3,495,000
289 Trismen Terrace
5 bed / 7 bath Single Family Home
MLS #O5435629
5,700 sq. ft.
Winter Park, FL 32789
True elegance inside & out... Perched high above the Lake Osceola shoreline on the WP chain of lakes, this Mizner style estate home designed by Vero Beach architect George Bollis has it all including panoramic lake…
Osceola Shores Sec 03
$2,950,000
401 Lakewood Drive
4 bed / 5 bath Single Family Home
MLS #O5435645
4,002 sq. ft.
Winter Park, FL 32789
This is a wonderful opportunity to own a gorgeous and sophisticated Winter Park lakefront estate with 287’ of frontage on Lake Osceola. Located on a point of land at the end of a cul-de-sac, this unique property…
South Interlachen Place
$2,878,000
125 S Interlachen Avenue #6
3 bed / 5 bath Town Home
MLS #O5432319
4,160 sq. ft.
Winter Park, FL 32789
Under Construction. Only two residences remain! Your opportunity to own unprecedented luxury in the most exclusive area of Winter Park has arrived. South Interlachen Place is around the corner from world famous Park…
Maitland Shores
$2,050,000
2219 Venetian Way
5 bed / 6 bath Single Family Home
MLS #O5428074
6,362 sq. ft.
Winter Park, FL 32789
This exclusive William Felkel custom built home has it all in the Winter Park Via's, including a new circular drive. It is a one of a kind 5 br 6 bath, 6,362 sq ft home which has every appointment imaginable! The custom…
Winter Park Old Town
$6,900,000
570 Seminole Drive
Vacant Land
MLS #O5439246
2.25 acres
Winter Park, FL 32789
This 2.25 acre lake front crown jewel is a once-in-a-lifetime offering of one of Old Winter Park’s most prestigious estate lots. Situated high above expansive Lake Osceola and only a short walk from famed Park…
$2,379,000
MLS #O5439527
1.62 acres
Winter Park, FL 32789
Perfect place to build your dream house. Located in Winter Park, this lot abutts Lake Virginia, near shopping A-rated schools, beautiful Lake Baldwin is very near.
Sylvan Lake Shores
$1,840,000
1511 Harris Circle
5 bed / 5 bath Single Family Home
MLS #O5441309
4,224 sq. ft.
Winter Park, FL 32789
Winter Park lakefront, designed like a historic Charleston home with a gated entrance courtyard that is enhanced by lovely gardens and a bubbling fountain. Full balconies along both the front & rear of this spectacular…
Mac Donald Robert Dhu Park
$11,900,000
161 Palmer Avenue
7 bed / 12 bath Single Family Home
MLS #O5436881
17,649 sq. ft.
Winter Park, FL 32789
Welcome to The Winter Park Lakeview Estate, a two-acre, contemporary paradise with panoramic views of Lake Maitland on the Winter Park Chain. Designed by NBA star Horace Grant, expanded by Alan Ginsburg, and featured in…
Park Hill
$3,350,000
639 N Park Avenue
3 bed / 5 bath Town Home
MLS #O5451650
4,237 sq. ft.
Winter Park, FL 32789
Under Construction... Park Hill, an ultra-luxury 10 townhome project by Hill Gray Seven LLC (only 7 remaining), is a once-in-a-lifetime opportunity to own the most exclusive and luxurious townhome ever built in Winter…
Lt A Blk A Rep
$3,195,000
1150 N Park Avenue
4 bed / 4 bath Single Family Home
MLS #O5452459
4,363 sq. ft.
Winter Park, FL 32789
Pristine Winter Park address! Spectacular Park Avenue lakefront pool home situated on just under an acre in the heart of town on Lake Maitland. This four bedroom, four bath home has been meticulously updated with…
Park Hill
$2,700,000
647 N Park Avenue
3 bed / 4 bath Town Home
MLS #O5452481
3,253 sq. ft.
Winter Park, FL 32789
Under Construction... Park Hill, an ultra-luxury 10 townhome project by Hill Gray Seven LLC (only 7 remaining), is a once-in-a-lifetime opportunity to own the most exclusive and luxurious townhome ever built in Winter…
Park Hill
$3,350,000
635 N Park Avenue
3 bed / 5 bath Town Home
MLS #O5465631
4,244 sq. ft.
Winter Park, FL 32789
Under Construction... Park Hill, an ultra-luxury 10 townhome project by Hill Gray Seven LLC (only 7 remaining), is a once-in-a-lifetime opportunity to own the most exclusive and luxurious townhome ever built in Winter…
$5,725,000
970 Via Lugano
6 bed / 9 bath Single Family Home
MLS #O5425581
10,190 sq. ft.
Premier lakefront estate in the heart of the Vias on Lake Maitland and built by Charles Clayton Construction... This Winter Park Chain of Lakes estate takes advantage of the elevated topography. Inspired by the…
Golfview Terrace
$2,475,000
900 N Park Avenue
5 bed / 7 bath Single Family Home
MLS #O5435150
5,035 sq. ft.
Winter Park, FL 32789
Elegant Mediterranean Estate custom built by Posada in the middle of downtown Winter Park on prestigious Park Avenue. The main residence sits on almost half an acre and also has a guest apartment with bedroom, full…
$2,375,000
788 N Interlachen Avenue
4 bed / 6 bath Single Family Home
MLS #O5452616
4,530 sq. ft.
Winter Park, FL 32789
Exceptional custom home by Carmen Dominguez with stunning architectural details throughout. Located only steps from Park Ave & its restaurants & shops, make this an enviable address. The stylish decor throughout begins…
Twelve Oaks
$8,900,000
1202 N Park Avenue
6 bed / 9 bath Single Family Home
MLS #O5466106
8,767 sq. ft.
Winter Park, FL 32789
For the first time in almost 20 years, this one of a kind private estate on "chain of lakes" located in the prestigious Twelve Oaks peninsula and walking distance to downtown Park Avenue is becoming available... This…
Forest Hills
$1,790,000
2171 Forrest Road
5 bed / 6 bath Single Family Home
MLS #O5460221
4,487 sq. ft.
Winter Park, FL 32789
New Rex-Tibbs Construction on beautiful corner lot in premier Winter Park location near Lake Sue in one of the most desirable neighborhoods in all of Winter Park… Modern coastal style home with standing seam metal…
Sylvan Park
$1,899,000
500 Sylvan Drive
5 bed / 6 bath Single Family Home
MLS #O5447720
3,596 sq. ft.
Winter Park, FL 32789
Under Construction! Winter Park LUXURY living at its absolute finest! Introducing Ira Kitograd (IBK Construction) and Zane Williams of Z Properties' newest innovative project! Built with impeccable quality in mind, no…
$1,895,000
141 Dana Way
5 bed / 7 bath Single Family Home
MLS #O5460562
4,526 sq. ft.
Winter Park, FL 32789
This fabulous new modern mediterranean home is situated on a picturesque corner lot w/ stately live oaks & a charming brick street all just steps from Lake Chelton & Lake Sue in one of the most sought after…
Windsong
$1,749,000
518 Genius Drive
5 bed / 6 bath Single Family Home
MLS #O5457476
4,736 sq. ft.
Winter Park, FL 32789
Gorgeous five bedroom, five and one-half bath pool home in Windsong. Desirable location puts you across the street from Lake Berry with partial lake views and the property backs up to a green space, so no rear…
Woodmere Terrace
$1,950,000
1155 Woodmere Drive
5 bed / 6 bath Single Family Home
MLS #O5467430
4,839 sq. ft.
Winter Park, FL 32789
Elegant Charleston style home w/ transitional interiors in heart of the Via’s… exquisite entry foyer looking straight out to picturesque back yard & pool area… on main level there is a private study w/ fireplace,…
Timberlane Shores
$3,300,000
561 Virginia Drive
5 bed / 7 bath Single Family Home
MLS #O5453529
5,041 sq. ft.
Winter Park, FL 32789
Stunning five bedroom home with 100’ on Lake Virginia. Completely remodeled by Wolfe-Rizer this home is a designer’s dream come true. Beautiful hardwood floors, gourmet kitchen, downstairs master retreat, home…
Maitland Shores
$3,150,000
2064 Venetian Way
4 bed / 5 bath Single Family Home
MLS #O5459844
4,638 sq. ft.
Winter Park, FL 32789
Gorgeous four bedroom, four and one half bath pool home with 65’ on Lake Maitland. Beautiful hardwood floors, crown moldings, custom built-ins, and high ceilings compliment the home’s interior with lake views from…
Alabama
$4,950,000
916 Palmer Avenue
5 bed / 5 bath Single Family Home
MLS #O5468354
4,259 sq. ft.
Winter Park, FL 32789
Extraordinary Winter Park Chain of Lakes opportunity with 1.8 buildable acres! Incredibly large 79,409 square feet tract of direct lakefront property on Lake Osceola with 231.4 ft of shoreline and spectacular views of…
Replat Of Green Oaks
$1,795,000
1761 Summerland Avenue
5 bed / 7 bath Single Family Home
MLS #O5448306
4,630 sq. ft.
Winter Park, FL 32789
This timeless new five bedroom transitional style home has traditional yet modern elements with its open floor plan, clean lines and light & bright feel. This home is perfect for entertaining or family living. First…
$2,595,000
660 Via Lugano
4 bed / 5 bath Single Family Home
MLS #O5442203
3,712 sq. ft.
Winter Park, FL 32789
Premier setting for this New Orleans style home on Lake Maitland in the heart of the Via’s! Spectacular views from almost every room in the home with southern exposure that provides bright light all day... Multiple …
Residences Condo
$2,095,000
300 S Interlachen Avenue #401
4 bed / 5 bath Condo
MLS #O5442958
4,090 sq. ft.
Winter Park, FL 32789
Sophisticated, New York Style living at the Residences in Winter Park. This recently updated end unit with north west exposure features stunning views of Downtown Winter Park, Lake Virginia and the City of Orlando…
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