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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

2156 Talman Court, Winter Park image
2156 Talman Court, Winter Park $2,495,000

Introducing a once-in-a-lifetime opportunity to own an exquisite multi-generational home in the coveted and exclusive neighborhood of Talman Mews, situated on not one, bu...

  • 5 Beds
  • 5.5 Baths
  • G5069117 MLS
1640 Mayfield Ave, Winter Park image
1640 Mayfield Ave, Winter Park $1,725,000

Located in desirable Winter Park, this beautiful single-story home is situated on an oversized lot of 0.28 acres surrounded by mature oaks, magnolia and an array of lush ...

  • 3 Beds
  • 2.5 Baths
  • O6113882 MLS
1451 Lyndale Boulevard, Winter Park image
1451 Lyndale Boulevard, Winter Park $1,750,000

Experience luxury living at its finest in this beautiful two-story pool home located in the highly desirable and historic Winter Park, FL. This stunning property boasts 5...

  • 5 Beds
  • 3.5 Baths
  • O6113129 MLS
1320 Orchid Avenue, Winter Park image
1320 Orchid Avenue, Winter Park $1,390,000 ▲

One or more photo(s) has been virtually staged. Under Construction. Introducing contemporary design and luxury living in Winter Park! This stunning new construction home,...

  • 4 Beds
  • 4 Baths
  • O6112725 MLS
2412 Chantilly Avenue, Winter Park image
2412 Chantilly Avenue, Winter Park $2,600,000

Under Construction. Breathtaking modern home just weeks away from completion. This sleek five-bedroom, six-and-a-half-bath residence abounds with high-end details through...

  • 5 Beds
  • 6.5 Baths
  • O6111525 MLS
1772 Chestnut Avenue, Winter Park image
1772 Chestnut Avenue, Winter Park $2,275,000

One or more photo(s) has been virtually staged. Welcome to Vimaro Homes newest completed Project! This listing showcases a stunning new construction project with an impre...

  • 5 Beds
  • 4.5 Baths
  • O6112581 MLS
222 W Rockwood Way, Winter Park image
222 W Rockwood Way, Winter Park $3,600,000

New Construction Custom Built Masterpiece located in one of Winter Park’s most desirable neighborhoods, zoned for top-rated schools in the county and only minutes away fr...

  • 5 Beds
  • 5.5 Baths
  • O6111531 MLS
1461 Via Tuscany, Winter Park image
1461 Via Tuscany, Winter Park $16,000,000

Proudly presenting a unique opportunity to acquire one of the most significant lakefront estates in Winter Park, on beloved Via Tuscany, moments from downtown Park Avenue...

  • 5 Beds
  • 4.5 Baths
  • O6112070 MLS
2819 Parkland Drive, Winter Park image
2819 Parkland Drive, Winter Park $2,395,000

Pre-Construction. To be built. Experience the perfect fusion of indoor-outdoor living, clean lines, and minimalist design in the heart of Winter Park. This California Mo...

  • 4 Beds
  • 4.5 Baths
  • O6110772 MLS
1461 Palm Avenue, Winter Park image
1461 Palm Avenue, Winter Park $2,100,000

Under Construction. Under construction. Beautiful New Construction home in the heart of Winter Park. This upscale Magnolia Home features upscale design features throughou...

  • 4 Beds
  • 4.5 Baths
  • O6109944 MLS
424 Turkey Run, Winter Park image
424 Turkey Run, Winter Park $1,297,500

This lovingly cared for transitional pool home with oversized lot is situated on a quiet tree-lined street. This spacious home is perfect for family living or entertainin...

  • 4 Beds
  • 3.5 Baths
  • O6108870 MLS
2019 Natalen Road, Winter Park image
2019 Natalen Road, Winter Park $1,395,000

Under Construction. New CUSTOM pool home a short walk to Winter Park High School. Open floor plan perfect for entertaining! Inviting front porch draws you in to spacious ...

  • 3 Beds
  • 4 Baths
  • O6109227 MLS
617 Penn Place, Winter Park image
617 Penn Place, Winter Park $3,495,000

This exquisite French Country estate is a true masterpiece, boasting a grand total of 4900 square feet of luxurious living space. Located in the highly coveted Penn Place...

  • 4 Beds
  • 3.5 Baths
  • O6108900 MLS
1840 Via Genoa, Winter Park image
1840 Via Genoa, Winter Park $2,650,000

Welcome home to this completely updated home located in the Via’s, one of the most sought-after neighborhoods in the heart of Winter Park. This home truly has it all and ...

  • 4 Beds
  • 5 Baths
  • O6109071 MLS
617 Balmoral Road, Winter Park image
617 Balmoral Road, Winter Park $1,250,000 ▼

New Price!! Beautifully renovated four-bedroom, three-full-bath Winter Park home. The incredible curb appeal begins with new landscaping, exterior lighting, paver drive,...

  • 4 Beds
  • 3 Baths
  • O6107793 MLS
1530 Mayfield Avenue, Winter Park image
1530 Mayfield Avenue, Winter Park $2,995,000 ▲

Located in Winter Park this home was devised by architectural firm, Green Apple & built by E2 Homes. Contemporary living adheres to a few principles that define its simpl...

  • 4 Beds
  • 4 Baths
  • O6108633 MLS
1863 Lake Spier Dr, Winter Park image
1863 Lake Spier Dr, Winter Park $1,175,000 ▼

RARE FIND - *** LAKE FRONTAGE on Private Lake Spier with DOCK, POOL,& CABANA which could never be built today!!!*** This home is in the perfect location only 0.7 miles or...

  • 4 Beds
  • 3 Baths
  • A4569512 MLS
2015 N Park Avenue, Winter Park image
2015 N Park Avenue, Winter Park — Park Ave $1,925,000

Welcome to 2015 N. Park Avenue - your brand new modern construction home! This stunning property is designed with contemporary features and high-end finishes throughout....

  • 4 Beds
  • 4.5 Baths
  • O6108514 MLS
  • Park Ave Bldg.
1756 Hollywood Ave, Winter Park image
1756 Hollywood Ave, Winter Park $1,000,000

Oversized double lot in the sought after stretch of Winter Park! Tree lined streets and eye-catching foliage add charm and character to the property. Upon walking throu...

  • 4 Beds
  • 3 Baths
  • G5068300 MLS
510 N Phelps Avenue, Winter Park image
510 N Phelps Avenue, Winter Park $3,200,000

For Data Entry Only!

  • 6 Beds
  • 6.5 Baths
  • O6102694 MLS
2315 Janice Avenue, Winter Park image
2315 Janice Avenue, Winter Park $1,200,000 ▼

BACK ON THE MARKET!!! This beautiful, lovingly cared for move-in ready, one story 4-bedroom 2.5 bath home offers you a unique opportunity to own in Winter park for under...

  • 5 Beds
  • 3 Baths
  • O6104821 MLS
1271 Via Capri, Winter Park image
1271 Via Capri, Winter Park $3,150,000 ▼

Luxurious and inviting, this custom one-owner home has it all and is on a quiet brick street in the desirable Via’s of Winter Park, elevated on a generous sized lot with ...

  • 5 Beds
  • 4.5 Baths
  • O6107391 MLS
1741 Glencoe Road, Winter Park image
1741 Glencoe Road, Winter Park $2,850,000

This beautiful 4-bedroom home (with a pool) sits close by between Lake Sue and Lake Virginia in one of the most sought-after neighborhoods of Winter Park. And in an area ...

  • 4 Beds
  • 4.5 Baths
  • O6106374 MLS
1303 Green Cove Road, Winter Park image
1303 Green Cove Road, Winter Park $1,975,000

*MULTIPLE OFFERS - HIGHEST and BEST due by 11 A.M. on Friday, April 28* We are excited to introduce you to 1303 Green Cove Road in Winter Park. The perfect balance of ele...

  • 5 Beds
  • 3.5 Baths
  • O6106232 MLS
1503 Palmer Avenue, Winter Park image
1503 Palmer Avenue, Winter Park $1,499,000

Fabulous single story home in the heart of Winter Park! This 4 bed, 3 bath home is situated on a large CORNER lot with a highly desirable 3 car garage! Step inside the fo...

  • 4 Beds
  • 3 Baths
  • O6105855 MLS
671 Via Lugano, Winter Park image
671 Via Lugano, Winter Park $4,950,000

Serene and private estate on a half acre lot in the Heart of Olde Winter Park. A custom built estate with amazing detail throughout boasts 6 bedrooms (downstairs master p...

  • 6 Beds
  • 6.5 Baths
  • O6104175 MLS
877 Brock Street, Winter Park image
877 Brock Street, Winter Park $1,395,000

Welcome to a beautiful and well-maintained home in the highly desirable Park Grove neighborhood. With a circular brick driveway and impressive street presence, this tradi...

  • 4 Beds
  • 2.5 Baths
  • O6097957 MLS
1618 Lookout Landing Circle, Winter Park image
1618 Lookout Landing Circle, Winter Park $2,100,000

Welcome to Windsong! One of the most sought-after communities in the heart of Winter Park with access to the historic Winter Park Chain of Lakes and near Park Avenue. Win...

  • 4 Beds
  • 3.5 Baths
  • O6105852 MLS
1115 N Pennsylvania Avenue, Winter Park image
1115 N Pennsylvania Avenue, Winter Park $2,450,000

Located in the Pennsylvania Place neighborhood of Winter Park, this custom built Mediterranean pool home is comprised of 4 bedrooms, 4 1/2 bathrooms totaling 3,576 square...

  • 4 Beds
  • 4.5 Baths
  • O6105811 MLS
241 E Fawsett Road, Winter Park image
241 E Fawsett Road, Winter Park $1,650,000

Data Entry Only!

  • 5 Beds
  • 5.5 Baths
  • O6102693 MLS
715 Via Lugano, Winter Park image
715 Via Lugano, Winter Park $3,850,000

A timeless estate in the heart of the Winter Park Vias. Brick paved walk paths and traditional exterior warmly welcome you into a home of classic luxury. The spectacular ...

  • 6 Beds
  • 7.5 Baths
  • J960068 MLS
1619 Elizabeths Walk, Winter Park image
1619 Elizabeths Walk, Winter Park $2,250,000

! Attention Buyers! Live Your best life in the desirable Windsong Subdivision in Winter Park. This beautiful custom built home, with attention paid to every detail, wel...

  • 4 Beds
  • 3.5 Baths
  • O6103519 MLS
1022 Mckean Circle, Winter Park image
1022 Mckean Circle, Winter Park $2,395,000

This custom four bedroom, three and one half bathroom, 4,610 square foot pool home is located in the heart of Olde Winter Park. From the paver covered circular drive you...

  • 4 Beds
  • 3.5 Baths
  • O6103545 MLS
465 N Phelps Avenue, Winter Park image
465 N Phelps Avenue, Winter Park $2,200,000

Pre-Construction. To be built. Modern Farmhouse with Pool is located in Winter Park and offers over 4500 sq. ft. of air-conditioned living space, with another 1,000 sq. ...

  • 7 Beds
  • 6 Baths
  • O6103239 MLS
4091 Scarlet Iris Place, Winter Park image
4091 Scarlet Iris Place, Winter Park $1,800,000

Absolutely gorgeous, executive home, located in a gated community in the beautiful Bear Gully Pointe, in Winter Park!. Masterfully designed with exquisite details of cont...

  • 6 Beds
  • 5.5 Baths
  • O6103005 MLS
1870 Laurel Road, Winter Park image
1870 Laurel Road, Winter Park $2,252,500

MULTIPLE OFFERS RECEIVED. Please present highest and best offer by Saturday 4/15 at 4pm. Located on a beautiful tree-lined brick street in Old Winter Park, this LunDev ho...

  • 4 Beds
  • 4.5 Baths
  • O6102704 MLS
1106 Palmer Avenue, Winter Park image
1106 Palmer Avenue, Winter Park $4,250,000

Elegant Charleston style residence secluded on a "private lane" in the heart of Olde Winter Park, just one property removed from Lake Osceola. Resting on over a ½ acre ma...

  • 4 Beds
  • 5.5 Baths
  • O6102003 MLS
1931 Laurel Road, Winter Park image
1931 Laurel Road, Winter Park $1,500,000

Don't miss out on this storybook, one-of-a-kind, Winter Park custom home perched on one of Winter Park's most desirable and delightful brick-lined streets. The stately Ch...

  • 4 Beds
  • 3.5 Baths
  • O6101208 MLS
1551 Laurel Road, Winter Park image
1551 Laurel Road, Winter Park $4,500,000

Nestled against the stunning backdrop of Lake Virginia on the Winter Park Chain of Lakes, this elegant Georgian estate rests on approximately 1 acre of land and has eleva...

  • 4 Beds
  • 5.5 Baths
  • O6090853 MLS
1144 N Pennsylvania Avenue, Winter Park image
1144 N Pennsylvania Avenue, Winter Park $1,299,999

Elegant and classic one-story home with an unbelievable downtown Winter Park location, walking distance to Park Avenue’s shops, restaurants, and 9-hole Winter Park Golf C...

  • 2 Beds
  • 2.5 Baths
  • O6100927 MLS
3708 Vinsetta Court, Winter Park image
3708 Vinsetta Court, Winter Park $1,100,000

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
600 Maiden Lane, Winter Park image
600 Maiden Lane, Winter Park $1,530,000

Perched on a hill, and 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 M...

  • 4 Beds
  • 4.5 Baths
  • O6099239 MLS
1303 Alberta Drive, Winter Park image
1303 Alberta Drive, Winter Park $2,750,000

Welcome to this exquisite French Modern home that seamlessly blends classic architecture with modern amenities. With 4 bedrooms, 4.5 bathrooms, 4,055 s/f, and a detached...

  • 4 Beds
  • 4.5 Baths
  • O6098947 MLS
2827 Parkland Circle, Winter Park image
2827 Parkland Circle, Winter Park $2,215,000

Welcome home to this professionally decorated two-story custom French provincial pool home. No space or detail has been overlooked, and with an endless list of upgrades, ...

  • 4 Beds
  • 3.5 Baths
  • O6098835 MLS
1651 Mayfield Avenue, Winter Park image
1651 Mayfield Avenue, Winter Park $1,950,000

This stunning home, built by LunDev Custom Homes, boasts clean, modern features and an exceptionally designed floorplan, while only steps from Phelps Park, tennis courts,...

  • 4 Beds
  • 4.5 Baths
  • O6098822 MLS
1918 Summerfield Road, Winter Park image
1918 Summerfield Road, Winter Park $1,175,000

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 br...

  • 5 Beds
  • 4.5 Baths
  • O6098383 MLS
1761 Greenwich Avenue, Winter Park image
1761 Greenwich Avenue, Winter Park $1,350,000

Like New! Remarkable 6 bed / 5 bath home in prime Winter Park 32789 location. Wonderful for entertaining and large families! Most attention to detail! Huge 92'x167' lot w...

  • 6 Beds
  • 3.5 Baths
  • O6098050 MLS
526 Genius Drive, Winter Park image
526 Genius Drive, Winter Park $3,500,000 ▼

Magnificent lakeview estate in Windsong – 526 Genius Drive, Winter Park. For the first time, this stately residence is on the market and available for purchase. Custom bu...

  • 4 Beds
  • 4.5 Baths
  • O6098024 MLS
1252 Via Del Mar, Winter Park image
1252 Via Del Mar, Winter Park $3,550,000

”Il Fenice” — A Modern Mediterranean home built and designed in 2020 by SMRS Design. This luxury estate located in The Vias area of Winter Park is offered fully furnished...

  • 5 Beds
  • 5.5 Baths
  • O6096686 MLS
195 Cortland Avenue, Winter Park image
195 Cortland Avenue, Winter Park $1,425,000

This fabulous home is on one of Winter Park’s most charming brick streets and a short stroll leads you to Lake Mizell. It features an abundance of natural light and blend...

  • 3 Beds
  • 3.5 Baths
  • O6096582 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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