Florida Neighborhood Realty
  • Sell Your Home & Save Thousands!
  • Buy A Home & Get Thousands!
  • Advanced Home Search
Login
407.801.3286

Sign in to your account

Need to reset your phone number?

Don't have an account with us?

Click here to sign up.

Home › Central Florida › Orlando Metro › Orange County › Windermere › Windermere Luxury Homes

Windermere Luxury Homes for Sale

When price is no object. When luxury, convenience, amenities, location, technology and privacy are what matter, Windermere is THE place you will find the largest selection of million dollar plus homes on the market. Many neighborhoods and areas in Windermere feature homes for the luxury market including those with one of a kind views of water, golf and exotic Florida preserves.

Below is a list of all active listings of luxury homes in Windermere priced over $2 Million.

Windermere Luxury Homes for Sale

9508 Windy Ridge Road, Windermere image
9508 Windy Ridge Road, Windermere $30,000,000

Nestled on 18 acres of pristine lakefront property, this exceptional estate offers a sanctuary of unparalleled beauty. With approximately 627 feet of frontage on Lake Dow...

  • 7 Beds
  • 14.5 Baths
  • Acreage & Unrec SubDv.
  • 34786 Zip Code
9306 Blanche Cove Drive, Windermere image
9306 Blanche Cove Drive, Windermere $16,500,000 ▼

Sophisticated elegance masterfully packaged into a custom-crafted lakefront mansion built specifically for the ultimate sports enthusiast, situated behind the secured man...

  • 5 Beds
  • 6.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
11301 Bridge House Road, Windermere image
11301 Bridge House Road, Windermere $11,995,000

Stunning modern masterpiece situated in Windermere's Reserve on Lake Butler Sound's most coveted waterfront lot. Known as "Overjoy" for its location on the sparkling wate...

  • 5 Beds
  • 7.5 Baths
  • Reserve At Lake Butler Sound SubDv.
  • 34786 Zip Code
5200 Isleworth Country Club Dr, Windermere image
5200 Isleworth Country Club Dr, Windermere $8,475,000 ▼

This stunning estate, complete with top-tier amenities and meticulously maintained to perfection, is a turnkey sale, inviting immediate occupancy and delight for its disc...

  • 5 Beds
  • 5.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
6432 Deacon Circle, Windermere image
6432 Deacon Circle, Windermere $8,300,000

Welcome to this magnificent lakefront estate in the Isleworth Country Club Community. This exceptional property offers the epitome of luxury living, combining a classic ...

  • 5 Beds
  • 7.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
11035 Schooner Way, Windermere image
11035 Schooner Way, Windermere $8,250,000 ▲

Pre-Construction. To be built. Where Art Meets Architecture! Build your Custom Dream Home with state of the art energy efficiency engineering in the tranquility of the so...

  • 7 Beds
  • 5.5 Baths
  • Marina Bay Estates SubDv.
  • 34786 Zip Code
6125 Grosvenor Shore Dr, Windermere image
6125 Grosvenor Shore Dr, Windermere $6,999,000

Stunning lakefront home in the highly desired, gated/24 hour guarded community of Keene’s Pointe. This home was thoughtfully built by highly regarded custom home builder...

  • 6 Beds
  • 6.5 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
5190 Latrobe Drive, Windermere image
5190 Latrobe Drive, Windermere $6,500,000

Spectacular modern property in the Beautiful gated community of Isleworth. Designed with a concrete structure, luxurious finishes, and numerous windows, this residence is...

  • 5 Beds
  • 6.5 Baths
  • Isle 4th Amd SubDv.
  • 34786 Zip Code
10821 Bayshore Dr, Windermere image
10821 Bayshore Dr, Windermere $6,490,000

One or more photo(s) has been virtually staged. Under Construction. Stunning custom lakefront home located on Lake Down, one of the famed Butler Chain of Lakes in Winderm...

  • 4 Beds
  • 4.5 Baths
  • Bayshore Estates SubDv.
  • 34786 Zip Code
5226 Isleworth Country Club Drive, Windermere image
5226 Isleworth Country Club Drive, Windermere $5,995,000

Located within the gates of the Isleworth Golf and Country Club community, this 7,821 square foot estate presents you with breathtaking views of the 8th fairway and glist...

  • 5 Beds
  • 5.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
5174 Vardon Drive, Windermere image
5174 Vardon Drive, Windermere $5,975,000

With gorgeous Classical Revival architecture, this estate sits on a coveted corner lot within the gates of Isleworth Golf & Country Club. Boasting over 10,000 square feet...

  • 6 Beds
  • 7.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
12632 Park Avenue, Windermere image
12632 Park Avenue, Windermere $5,950,000 ▼

One or more photo(s) has been virtually staged. Discover the epitome of luxury living in this extraordinary custom lakefront estate, located within the prestigious gated...

  • 6 Beds
  • 9.5 Baths
  • Chaine Du Lac SubDv.
  • 34786 Zip Code
12540 Park Avenue, Windermere image
12540 Park Avenue, Windermere $5,800,000

Experience the epitome of sophistication at this exquisite Park Avenue estate, cradled in a treasured cove of Lake Butler. As you step inside, harmonious blends of transi...

  • 5 Beds
  • 5.5 Baths
  • Chaine De Lac SubDv.
  • 34786 Zip Code
11217 Bridge House Road, Windermere image
11217 Bridge House Road, Windermere $5,350,000 ▼

This exquisite 1-acre property is situated on Lake Butler, widely regarded as the most sought-after lake in the Windermere chain. With almost 7,000 square feet of true lu...

  • 6 Beds
  • 8 Baths
  • Reserve At Lake Butler Sound 45/120 SubDv.
  • 34786 Zip Code
5084 Isleworth Country Club Drive, Windermere image
5084 Isleworth Country Club Drive, Windermere $4,750,000

Updated golf front estate with new *roof and generator, offers supreme vistas of the 6th Green along the legendary course of Isleworth Golf & Country Club. Spanning over ...

  • 6 Beds
  • 7.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
225 Magnolia Street, Windermere image
225 Magnolia Street, Windermere $4,500,000

Back on the market. Buyer's financing fell thru. Elegantly designed and custom-built in 2019, this Mediterranean-style home is located on the famed Butler Chain of Lakes....

  • 7 Beds
  • 10.5 Baths
  • Windermere Town SubDv.
  • 34786 Zip Code
9247 Tibet Pointe Cir, Windermere image
9247 Tibet Pointe Cir, Windermere $4,450,000

This stunning lakefront home in Keene’s Pointe offers a rare blend of modern Farm Style aesthetics and timeless elegance. Situated on an expansive lot exceeding three acr...

  • 6 Beds
  • 6.5 Baths
  • Keenes Pointe 46/104 SubDv.
  • 34786 Zip Code
4807 Alexandra Garden Court, Windermere image
4807 Alexandra Garden Court, Windermere $4,400,000

Located within the Garden Villas enclave of Isleworth Golf & Country Club, this spacious estate epitomizes luxury living. With an impressive 5,741 square feet of meticulo...

  • 4 Beds
  • 5.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
4047 Isabella Circle, Windermere image
4047 Isabella Circle, Windermere $3,999,000 ▲

This exceptional 2019 luxury property, extensively remodeled in 2021, holds the distinction of being the largest internally in Casabella condominium and the sole Casabell...

  • 6 Beds
  • 7.5 Baths
  • Casabella Ph 2 SubDv.
  • 34786 Zip Code
9725 Chestnut Ridge Drive, Windermere image
9725 Chestnut Ridge Drive, Windermere $3,995,000 ▼

Unbelievable Price Reduction! A Florida Paradise Awaits You within the prestigious 600-acre enclave of Isleworth Golf and Country Club! You will find this extraordinary c...

  • 5 Beds
  • 6 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
800 W 2nd Avenue, Windermere image
800 W 2nd Avenue, Windermere $3,900,000 ▼

Elevator to 2nd Floor - Detached Guest Suite overlooking Pool with Fireplace has Private Entrance in Courtyard - Courtyard Pool with Waterfall from the Heated Spa has the...

  • 5 Beds
  • 4.5 Baths
  • Aladar On Lake Butler SubDv.
  • 34786 Zip Code
5373 Isleworth Country Club Drive, Windermere image
5373 Isleworth Country Club Drive, Windermere $3,900,000

Under Construction. (Renovation) An exceptional opportunity awaits to take over an existing property within the prominent Isleworth Country Club community. Situated grace...

  • 5 Beds
  • 5.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
9950 6th Street, Windermere image
9950 6th Street, Windermere $3,499,900

Under Construction. UNDER CONSTRUCTION - estimated completion January 2024. From its head-turning design to the meticulous attention to detail around every corner, this 5...

  • 4 Beds
  • 5.5 Baths
  • Gotha SubDv.
  • 34786 Zip Code
4071 Isabella Circle, Windermere image
4071 Isabella Circle, Windermere $3,490,000

Step into a world of luxury with this magnificent Windermere home, nestled within the prestigious gated Casabella neighborhood. The moment you enter, you are greeted by a...

  • 5 Beds
  • 6.5 Baths
  • Casabella Ph 2 SubDv.
  • 34786 Zip Code
5186 Vardon Drive, Windermere image
5186 Vardon Drive, Windermere $3,095,000

Nestled along the front nine of Isleworth’s renowned championship golf course overlooking Hole 3, this beautiful estate offers a lovely location featuring golf course vie...

  • 4 Beds
  • 4.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
2006 Bellamere Court, Windermere image
2006 Bellamere Court, Windermere $3,090,000 ▼

FULLY FURNISHED!!! Welcome to the exquisite 2006 Bellamere Ct, a masterpiece crafted by Element Home Builders. Discover the epitome of luxury living with their renowned "...

  • 5 Beds
  • 4.5 Baths
  • Bella Vita Estates SubDv.
  • 34786 Zip Code
9042 Pinnacle Circle, Windermere image
9042 Pinnacle Circle, Windermere $2,995,000 ▼

Welcome to this stunning 7-bedroom, 5.5-bathroom estate nestled on a private 2-acre lot in the highly acclaimed Lake Down Crest neighborhood of Windermere. Boasting an im...

  • 7 Beds
  • 5.5 Baths
  • Lake Down Crest SubDv.
  • 34786 Zip Code
325 Magnolia Street, Windermere image
325 Magnolia Street, Windermere $2,988,000 ▼

The allure of the Butler Chain of Lakes beckons! Nestled in the heart of the Town of Windermere on Lake Down, this expansive 3975 sq ft 4 bedroom 3 bathroom residence ...

  • 4 Beds
  • 3 Baths
  • Windermere Town SubDv.
  • 34786 Zip Code
2012 Bellamere Court, Windermere image
2012 Bellamere Court, Windermere $2,950,000

This fully furnished and former model home of beautiful Bella Vita Estates in Windermere will take your breath away. The property is loaded with tons of upgrades and is m...

  • 5 Beds
  • 5.5 Baths
  • Bella Vita Estates SubDv.
  • 34786 Zip Code
13334 Bellaria Circle, Windermere image
13334 Bellaria Circle, Windermere $2,699,000

Welcome! This exquisite luxury residence is the epitome of sophistication, offering an unparalleled living experience in the sought after, guarded & gated Bellaria Commun...

  • 5 Beds
  • 5.5 Baths
  • Bellaria SubDv.
  • 34786 Zip Code
2455 Maguire Road, Windermere image
2455 Maguire Road, Windermere $2,600,000

This 4 Bedroom 3 Full & 2 Half Bath Luxurious Lakefront Pool Home also boasts a Separate Home Office and 2nd Floor Bonus Room with Kitchenette and Full Bath having a Balc...

  • 4 Beds
  • 3.5 Baths
  • Lake Down Estates SubDv.
  • 34786 Zip Code
1815 Windermere Road, Windermere image
1815 Windermere Road, Windermere $2,499,000

Pre-Construction. To be built. Welcome to 1815 Windermere Road! This remarkable design by Hanson Custom Homes presents a rare opportunity in a tranquil and secluded setti...

  • 4 Beds
  • 4.5 Baths
  • 34786 Zip Code
1238 Lake Whitney Drive, Windermere image
1238 Lake Whitney Drive, Windermere $2,475,000 ▼

$25K PRICE REDUCTION - VERY MOTIVATED SELLERS!! Welcome to the exquisite and elegant Reserve At Belmere. A true luxury Tuscan style luxury home with spectacular views of ...

  • 4 Beds
  • 5.5 Baths
  • Reserve At Belmere Ph 02 48 144 SubDv.
  • 34786 Zip Code
9204 Tibet Pointe Circle, Windermere image
9204 Tibet Pointe Circle, Windermere $2,400,000

Stunning Keene's Pointe home! Everything you are looking for in a custom home. Built by Stonebridge, this home has plenty of space for everyone and everything. The first ...

  • 5 Beds
  • 4.5 Baths
  • Keenes Pointe 46/104 SubDv.
  • 34786 Zip Code
9025 Balmoral Mews Square, Windermere image
9025 Balmoral Mews Square, Windermere $2,399,999

One or more photo(s) has been virtually staged. UNDER CONSTRUCTION HOUSE WILL BE COMPLETED BY DEC 31!. Step into contemporary elegance inside and out. This 5 Bedroom 3.2...

  • 5 Beds
  • 3.5 Baths
  • Balmoral SubDv.
  • 34786 Zip Code
1128 Estancia Woods Loop, Windermere image
1128 Estancia Woods Loop, Windermere $2,349,000

This charming and meticulously maintained home is a hidden gem nestled in the serene and desirable community of Estancia Woods. With its superb location, well-appointed f...

  • 5 Beds
  • 6.5 Baths
  • Estancia At Windermere SubDv.
  • 34786 Zip Code
1003 Oakdale Street, Windermere image
1003 Oakdale Street, Windermere $2,300,000 ▼

If You Have Dreamed of Having a Home Where Family and Friends want to Hang Out and Spend Quality Time Building Lifetime Friendships and Cherished Memories then I have the...

  • 5 Beds
  • 4.5 Baths
  • Windermere Town SubDv.
  • 34786 Zip Code
81 Oakdale Street, Windermere image
81 Oakdale Street, Windermere — Davis Shores S/123 Lot 4 Blk B $2,197,000 ▼

Welcome to 81 Oakdale Street, a stunning lakefront home located along the famous Butler Chain of Lakes on the Lake Down Canal. This magnificent custom built estate offers...

  • 5 Beds
  • 4.5 Baths
  • Davis Shores SubDv.
  • 34786 Zip Code
11840 Vinci Drive, Windermere image
11840 Vinci Drive, Windermere $2,070,000

Luxury living in one of the most desirable 24 hour guard gated Keene's Pointe Community. This immaculate home features an open floor plan with breathtaking kitchen recent...

  • 6 Beds
  • 5.5 Baths
  • Keenes Pointe Un #11 SubDv.
  • 34786 Zip Code
Like or Share
Loading likes...

Address Search

Ziro RealtySell Your Home & Save Thousands
Buy A Home & Get Thousands

Realtor David MyersDavid Myers 407-801-3286
Your Windermere Real Estate Expert

Windermere Neighborhoods

  • Arlington Bay
  • Ashlin Park
  • Balmoral
  • Bellaria
  • Bella Vita
  • Belmere Village
  • Berkshire Park
  • Butler Ridge
  • Carrington
  • Casa Del Lago
  • Casabella
  • Chaine Du Lac
  • Courtleigh Park
  • Crescent Lake Estates
  • Cypress Chase
  • Cypress Isle
  • Eden Isle
  • Enclave Wndrmr Lndng
  • Estancia Windermere
  • Estates at Lake Clarice
  • Estates at Windermere
  • Glenmuir
  • Grande Pines
  • Harbor Isle
  • Havencrest
  • Isleworth
  • Keenes Pointe
  • Lake Burden
  • Lake Butler Estates
  • Lake Butler Sound
  • Lake Buynak Estates
  • Lake Cawood Estates
  • Lake Crescent Reserve
  • Lake Cypress Cove
  • Lake Down Cove
  • Lake Down Crest
  • Lake Down Estates
  • Lake Down Reserve
  • Lake Down Shores
  • Lake Mabel Shores
  • Lake Olivia Reserve
  • Lake Reams Townhomes
  • Lake Sawyer
  • Lake Sheen Reserve
  • Lakes at Lake Down
  • Lakes of Windermere
  • Lakeside
  • Lakeside Village
  • Legado
  • Les Terraces
  • Mabel Bridge
  • Magnolia Park
  • Manors at Butler Bay
  • Marina Bay Estates
  • Merrick Landing
  • Newbury Park
  • Oasis Cove
  • Oxford Moor
  • Peachtree Park
  • Prsrve Lks Windermere
  • Preston Square
  • Providence
  • Providence Lake Sheen
  • Reserve at Belmere
  • Reserve at Windermere
  • Roberts Landing
  • Royal Cypress Preserve
  • Royal Estates
  • Royal Ranch Estates
  • Sawyer Sound
  • Silver Woods
  • Southbridge Village
  • Southern Acres
  • Summerport
  • Sunset Bay
  • Thornhill
  • Tildens Grove
  • Tuscany Ridge
  • Vineyards
  • Waterford Pointe
  • Waterstone
  • Weatherstone
  • West Lake Butler Estates
  • Westminster Landing
  • Westover Club
  • Westover Reserve
  • Westside Village
  • Wickham Park
  • Willows at Lake Rhea
  • Windermere Club
  • Windermere Downs
  • Windermere Grande
  • Windermere Isle
  • Windermere Landing
  • Windermere Oaks
  • Windermere Pointe
  • Windermere Reserve
  • Windermere Ridge
  • Windermere Sound
  • Windermere Terrace
  • Windermere Town
  • Windermere Trails
  • Windsor Hill
  • Windstone
  • Woods of Windermere
  • Worthington Park

Windermere Interactive Map Search

Windermere Interactive Real Estate Map Search

Popular Windermere Searches

  • 25 Latest Windermere Listings
  • Top 10 Most Expensive Windermere Homes
  • Windermere Commercial Properties
  • Windermere Condos
  • Windermere Foreclosures
  • Windermere Gated Homes
  • Windermere Land
  • Windermere Luxury Homes
  • Windermere New Construction
  • Windermere No HOA Homes
  • Windermere Pool Homes
  • Windermere Townhomes
  • Windermere Waterfront Homes

cash back at closing from Ziro Realty

ALL about Windermere!

  • About Windermere
  • Butler Chain of Lakes
  • Windermere Apartments
  • Windermere Contacts
  • Windermere Events
  • Windermere Golf
  • Windermere Grocery
  • Windermere Hospitals
  • Windermere Parks
  • Windermere Rentals
  • Windermere Restaurants
  • Windermere Schools
  • Windermere Shopping
  • Windermere - Wiki Page
  • Where is Windermere
  • Town of Windermere Site

Get Ziro-ed In

  • Sellers - Get Your Windermere Homes Value
  • Sellers - Save Thousands on Your Listing
  • Buyers - Get Your Windermere Market Report
  • Buyers - Get a Pre-Qualified for a Mortgage
  • Buyers - Get Get Thousands Back
  • Agents - Get Your Career Going with Ziro

About Florida Neighborhood Realty powered by Ziro Realty

Communities Adjacent to Winter Garden

  • Ocoee
  • Gotha
  • Winter Garden
  • MyOrlandoVacationHome.com
  • NonaOrlandoProperties.com
David Myers - Broker Associate
Florida Neighborhood Realty Team
Ziro Realty, LLC
619 Celebration Ave
Celebration, FL 34747
Phone: 407-801-3286
www.FloridaNeighborhoodRealty.com





© 2023 - All Rights Reserved

Site Support

  • About Us
  • Contact Us
  • Work at Ziro
  • Facebook
  • Twitter/X
  • Office Listings
  • Instagram
  • Neighborhood Blog
IDX Real Estate Websites by
• Accessibility • Terms • Privacy
80402