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Search All Winter Park FL Luxury Homes Over $1 Million For Sale

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Search All Winter Park FL Luxury Homes Over $1 Million For Sale

Our website features the best Winter Park FL Luxury Home search including real estate, 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 Winter Park FL Luxury Home Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can view a current Winter Park FL Luxury Home Market Report to see what’s active, under contract, and sold in your neighborhood! 

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Just Listed Winter Park FL Luxury Homes Over $1 Million For Sale

1016 Tuscany Place, Winter Park image
1016 Tuscany Place, Winter Park $1,479,000

Welcome to your mid-century modern home of endless possibilities. Situated on an oversized (.40 acre) lot in the family-friendly Tuscany Place neighborhood of “the Winter...

  • 5 Beds
  • 3.5 Baths
  • O6087704 MLS
1400 Lyndale Boulevard, Winter Park image
1400 Lyndale Boulevard, Winter Park $1,175,000

Charleston-style home on a picturesque tree-lined corner lot secluded off of Park Avenue in a quiet setting near downtown Winter Park. One-owner home since originally cus...

  • 4 Beds
  • 2.5 Baths
  • O6087928 MLS
2138 Lake Drive, Winter Park image
2138 Lake Drive, Winter Park $3,295,000

Lakefront luxury on the beautiful shores of Lake Killarney! Custom built with attention paid to every detail, this Mediterranean oasis delivers 4 spacious bedrooms, 3 ful...

  • 4 Beds
  • 3.5 Baths
  • O6086964 MLS
1531 Place Picardy, Winter Park image
1531 Place Picardy, Winter Park $1,895,000

An elegant custom home, designed & built by FG Shaub, is tucked away on a large corner lot on a pristine oak-lined street, offering incredible privacy. This home offers t...

  • 4 Beds
  • 4 Baths
  • O6088081 MLS
4464 Tuscany Island Court, Winter Park image
4464 Tuscany Island Court, Winter Park $1,625,000

Enjoy the Winter Park lifestyle in this fabulous 4 bedroom, 4.5 bath home, built in 2006 with a clean and well-planned 4625 sqft floorplan. This beautiful Mediterranean s...

  • 4 Beds
  • 4.5 Baths
  • O6087707 MLS
335 Beloit Avenue, Winter Park image
335 Beloit Avenue, Winter Park $1,150,000

Come see this beautiful home on a highly desirable street! Enter the home through the well sized foyer and right into your living room/dining room area, separated by a do...

  • 3 Beds
  • 2 Baths
  • O6087445 MLS
1017 Via Tuscany Oaks Way, Winter Park image
1017 Via Tuscany Oaks Way, Winter Park $2,250,000

Modern Mediterranean on a quiet cul-de-sac street off of Via Tuscany with an oversized beautiful treed lot. Spacious flexible floor plan with private owner’s suite and ho...

  • 5 Beds
  • 5.5 Baths
  • O6086002 MLS
4400 Tuscany Island Court, Winter Park image
4400 Tuscany Island Court, Winter Park $3,999,777

Welcome to Tuscany Island in Winter Park! Private gated enclave of 5 magnificent luxury estate homes, resting on the lake shore of Bear Gulley. This highly sought-after a...

  • 4 Beds
  • 5.5 Baths
  • O6084698 MLS
580 Ololu Drive, Winter Park image
580 Ololu Drive, Winter Park $1,495,000

Luxury Lifestyle on Beautiful Lake Killarney. Enjoy the serenity of lakeside living on the largest and cleanest private lake in Winter Park. Lake Killarney is the hidden ...

  • 3 Beds
  • 2.5 Baths
  • O6084616 MLS
151 Oakwood Way, Winter Park image
151 Oakwood Way, Winter Park $2,425,000

Under Construction. Fabulous new construction, new transitional coastal home situated on quiet, brick tree-lined street convenient to downtown Winter Park, Baldwin Park, ...

  • 4 Beds
  • 4.5 Baths
  • O6082762 MLS
660 W Morse Boulevard, Winter Park image
660 W Morse Boulevard, Winter Park — Morse $2,500,000

This Home is a classically set up modern brownstone with private elevator. Situated within close distance to Hannibal Square and Park Avenue, the premiere shopping and ...

  • 3 Beds
  • 3.5 Baths
  • O6084405 MLS
  • Morse Bldg.
850 E Lake Sue Avenue, Winter Park image
850 E Lake Sue Avenue, Winter Park $3,250,000

A Custom Home in Timberlane Shores… JACKPOT!! This stunning & sophisticated masterpiece sits on a corner lot, which spans almost 16,000 SF, offers over 5,300 SF of living...

  • 5 Beds
  • 5.5 Baths
  • O6081012 MLS
170 S Phelps Avenue, Winter Park image
170 S Phelps Avenue, Winter Park $2,800,000

Under Construction. Soon to be completed. A stunning modern transitional home located in the heart of Winter park minutes from Park Ave. As you enter this home through th...

  • 4 Beds
  • 4.5 Baths
  • O6081597 MLS
3720 Vinsetta Court, Winter Park image
3720 Vinsetta Court, Winter Park $1,100,000

Located within the Winter Park gated community of Lakeside Estates, this beautiful, luxury home, located on a quiet cul-de-sac, is ready to welcome a new family. This wel...

  • 6 Beds
  • 5 Baths
  • O6082646 MLS
1290 Park Ave, Winter Park image
1290 Park Ave, Winter Park $4,575,000 ▼

Nestled along the shores, on approximately an acre property on Lake Maitland walking distance to downtown Park Ave, with one of the most sought-after addresses in Winter ...

  • 4 Beds
  • 3.5 Baths
  • O6082393 MLS
690 N New York Avenue, Winter Park image
690 N New York Avenue, Winter Park $4,600,000

April 2022 construction! This newly constructed home is move-in ready and available for a quick closing! Do not miss the once-in-a-lifetime opportunity to own this rare...

  • 4 Beds
  • 4.5 Baths
  • O6082781 MLS
450 Ololu Drive, Winter Park image
450 Ololu Drive, Winter Park $1,699,000

Enjoy fabulous direct views of Lake Killarney from all living areas, kitchen & master suite. Unbelievable upscale finishes include marble flooring, imported Indonesian te...

  • 5 Beds
  • 5.5 Baths
  • O6081800 MLS
2723 Norris Avenue, Winter Park image
2723 Norris Avenue, Winter Park $2,199,999

Pre-Construction. To be built. Pre-Construction. To be built. This Cape Cod inspired home provides a rare pre-construction opportunity in highly coveted Winter Park. Make...

  • 4 Beds
  • 3.5 Baths
  • O6081797 MLS
1146 Oaks Boulevard, Winter Park image
1146 Oaks Boulevard, Winter Park $1,390,000

Sold Data Entry Only.

  • 4 Beds
  • 3.5 Baths
  • J956550 MLS
266 Detmar Drive, Winter Park image
266 Detmar Drive, Winter Park $1,850,000 ▼

This Beautiful Custom Mediterranean Home WALKABLE TO PARK AVENUE offers the finest of quality throughout, with custom ceilings, detailed woodwork, and hand painted accent...

  • 4 Beds
  • 4.5 Baths
  • O6080463 MLS
1050 Keyes Avenue, Winter Park image
1050 Keyes Avenue, Winter Park $1,945,000

Don’t miss this rare opportunity to live on one of the most sought-after streets, where only a handful of homes in the city can boast the experience of living on the pres...

  • 4 Beds
  • 4.5 Baths
  • O6079898 MLS
664 W Morse Boulevard, Winter Park image
664 W Morse Boulevard, Winter Park $4,299,000

One or more photo(s) has been virtually staged. Under Construction. “UNDER CONSTRUCTION” Completion end of May. This custom built Winter Park home is the epitome of luxu...

  • 4 Beds
  • 4.5 Baths
  • O6080006 MLS
1913 Sycamore Drive, Winter Park image
1913 Sycamore Drive, Winter Park $1,475,000

Under Construction. Under construction. New construction home in desirable Audubon Park school district. Welcome home to this timeless Traditional elevation. As you step ...

  • 4 Beds
  • 4.5 Baths
  • O6079806 MLS
2011 N Park Avenue, Winter Park image
2011 N Park Avenue, Winter Park — Anchor Homes & Developement $2,075,000

Under Construction. New Construction Home is almost complete! This modern pool home is truly one of a kind designed to wow your family and friends. This executive pool ho...

  • 4 Beds
  • 3.5 Baths
  • O6078219 MLS
  • Anchor Homes & Developement Bldg.
3708 Vinsetta Court, Winter Park image
3708 Vinsetta Court, Winter Park $1,275,000

One or more photo(s) has been virtually staged. Welcome Home! Your search is over with this stunning 2015 built Energy-Efficient move-in ready premium corner lot 6-bedroo...

  • 6 Beds
  • 5 Baths
  • 1103698 MLS
771 Williams Drive, Winter Park image
771 Williams Drive, Winter Park $1,397,000

Sought-after Park Grove neighborhood. Five-bedroom, five-bath pool home on .43 acres. Close to Park Avenue! Corner lot, well-maintained family home. Premium location, cla...

  • 5 Beds
  • 5 Baths
  • O6074216 MLS
3708 Vinsetta Court, Winter Park image
3708 Vinsetta Court, Winter Park $1,275,000

One or more photo(s) has been virtually staged. Welcome Home! Your search is over with this stunning 2015 built Energy-Efficient move-in ready premium corner lot 6-bedroo...

  • 6 Beds
  • 5 Baths
  • O6073328 MLS
2234 Via Luna, Winter Park image
2234 Via Luna, Winter Park $1,650,000

Elegant four bedroom, three and a half-bath home in the famous Via’s of Winter Park, privately positioned on a 3 sided open corner lot. It is meticulously maintained wit...

  • 4 Beds
  • 3.5 Baths
  • O6075542 MLS
1645 Dale Avenue, Winter Park image
1645 Dale Avenue, Winter Park $3,050,000

Fabulous custom Winter Park home completed in 2020, situated on a quiet brick street minutes from Park Avenue shopping & restaurants, Phelps Park, the Y & elementary scho...

  • 5 Beds
  • 5.5 Baths
  • O6072898 MLS
1633 Pine Avenue, Winter Park image
1633 Pine Avenue, Winter Park $1,250,000

Stunning ONE STORY 4 BR - 3.5 BA POOL home situated on oversized 100 X 130 lot in the heart of Winter Park. Located on the quiet part of Pine between Phelps and Woodale,...

  • 4 Beds
  • 3.5 Baths
  • O6072876 MLS
2325 Chantilly Avenue, Winter Park image
2325 Chantilly Avenue, Winter Park $1,775,000

Stunning pool home located on a quiet street in the heart of Winter Park includes a private backyard oasis and a detached apartment/guest house. As you step through the f...

  • 5 Beds
  • 4.5 Baths
  • O6072590 MLS
2012 Howard Drive, Winter Park image
2012 Howard Drive, Winter Park $1,031,000

Stunning Winter Park pool home completely renovated in 2018! Nestled in the highly sought after Timberlane neighborhood this single-story open floor plan has been meticul...

  • 3 Beds
  • 2 Baths
  • O6072076 MLS
785 Via Lombardy, Winter Park image
785 Via Lombardy, Winter Park $5,650,000

Under Construction. Today’s Florida living at its finest in this premier 2023 new construction residence nearing completion in the heart of the Vias by Z Properties Inc. ...

  • 5 Beds
  • 5.5 Baths
  • O6071285 MLS
558 Genius Drive, Winter Park image
558 Genius Drive, Winter Park $2,415,000

Impressive Mediterranean inspired residence situated on a tranquil and private lot within the coveted North Shore section of the highly sought after Windsong community in...

  • 4 Beds
  • 4.5 Baths
  • O6070335 MLS
1750 Via Tuscany, Winter Park image
1750 Via Tuscany, Winter Park $5,500,000

Ensconced in the distinguished enclave, "The Vias", this meticulous Winter Park estate is the epitome of thoughtful design and impeccable quality. This bespoke residence ...

  • 6 Beds
  • 6.5 Baths
  • O6069450 MLS
704 W Comstock Avenue, Winter Park image
704 W Comstock Avenue, Winter Park $1,375,000

New Construction Just Completed! This Beautiful Modern / Transitional Home has a Warm and Clean Open Floor Plan concept with Soaring Ceilings and Great Natural Lighting. ...

  • 3 Beds
  • 3.5 Baths
  • O6069799 MLS
201 Osceola Court, Winter Park image
201 Osceola Court, Winter Park $1,500,000

Beautiful lake Front on Lake Osceola, The Winter Park Chain of Lakes. Rare opportunity to be on the areas most sought after chain, in the Heart of Winter Park! Bring your...

  • 3 Beds
  • 2 Baths
  • O6069463 MLS
890 N Phelps Avenue, Winter Park image
890 N Phelps Avenue, Winter Park $1,325,000

Custom renovated home located in the highly desirable city of Winter Park offering over 3,600 square feet of living space with an abundance of natural lighting. The forma...

  • 4 Beds
  • 3.5 Baths
  • O6068280 MLS
2172 Temple Drive, Winter Park image
2172 Temple Drive, Winter Park $2,650,000

Pre-Construction. To be built. Pre-Construction, To Be Built. Elegance, comfort, and a welcoming environment blend cohesively at this modern West Indies new construction ...

  • 5 Beds
  • 4 Baths
  • O6068470 MLS
850 Virginia Drive, Winter Park image
850 Virginia Drive, Winter Park $1,120,000

This lovely, spacious Winter Park home is situated high on a corner lot tucked away in sought after Timberlane Shores surrounded by multi million dollar homes. As you ent...

  • 5 Beds
  • 2.5 Baths
  • O6067851 MLS
1520 Highland Road, Winter Park image
1520 Highland Road, Winter Park $2,300,000

Look no further than this immaculate pool home located in the highly desirable Winter Park neighborhoods just minutes away from Park Avenue! Tucked up across the street f...

  • 5 Beds
  • 5.5 Baths
  • O6068164 MLS
1166 Oaks Boulevard, Winter Park image
1166 Oaks Boulevard, Winter Park $1,750,000 ▼

Custom luxurious Winter Park Estate located in the highly desirable subdivision of Dixie Terrace (walkable to Whole Foods, Winter Park Village, and Park Ave). 2018 Build,...

  • 4 Beds
  • 3.5 Baths
  • O6067141 MLS
2218 Fosgate Drive, Winter Park image
2218 Fosgate Drive, Winter Park $1,245,000

This beautifully renovated home is EXQUISITE! The home has been completely updated with the finest of materials. The spacious open floor plan features a state of the ar...

  • 4 Beds
  • 4 Baths
  • O6067623 MLS
1824 Harland Park Drive, Winter Park image
1824 Harland Park Drive, Winter Park $3,250,000 ▼

*VIDEO TOUR & 3D TOUR AVAILABLE* It’s time to live your best life! Casa Allegra is a full-custom Spanish-villa style home designed by the awarded company Morales-Keesee D...

  • 6 Beds
  • 3.5 Baths
  • O6064908 MLS
2430 Brookshire Avenue, Winter Park image
2430 Brookshire Avenue, Winter Park $1,100,000

Elegantly designed newer pool home nestled in one of Winter Park's most established sought-after neighborhoods. Light and bright four-bedroom, four-and-a-half-bath home f...

  • 4 Beds
  • 4.5 Baths
  • O6065023 MLS
1318 Morton Road, Winter Park image
1318 Morton Road, Winter Park $2,360,000 ▲

Under Construction. Under Construction. Contemporary luxury masterpiece home ready to closing at the end of this year. Exclusive Architectural Design, strong structure wi...

  • 4 Beds
  • 3.5 Baths
  • S5075338 MLS
2522 Lafayette Avenue, Winter Park image
2522 Lafayette Avenue, Winter Park $2,895,000 ▲

New Construction. Contemporary luxury masterpiece home ready to closing at the end of this year. Exclusive Architectural Design, strong structure with two-story concrete-...

  • 4 Beds
  • 3.5 Baths
  • S5075342 MLS
620 Gaines Way, Winter Park image
620 Gaines Way, Winter Park $2,985,000

This fabulous Parade of Homes Winner was used as a second home only lived in one day a week! This timeless traditional pool home is situated on a quiet cul-de-sac street...

  • 5 Beds
  • 5.5 Baths
  • O6063278 MLS
2813 Northwood Boulevard, Winter Park image
2813 Northwood Boulevard, Winter Park $1,550,000 ▼

Welcome home to this two-story contemporary pool home full of upgrades featuring four bedrooms plus a large sun-filled office, three-and-a-half baths and a two-car garage...

  • 4 Beds
  • 3.5 Baths
  • O6061821 MLS
1791 Grinnell Terrace, Winter Park image
1791 Grinnell Terrace, Winter Park $1,545,000

Stunning Winter Park home freshly remodeled in 2021-2022. This home missed no details when it comes to finishes and using the highest quality products. All around the hom...

  • 4 Beds
  • 4 Baths
  • O6059682 MLS
© 2023 Northeast Florida Multiple Listing Service, Inc. All rights reserved. This data is up-to-date as of . For the most current information, contact Real Estate Company.

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