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781 results in Windermere, Winter Park, for All Types Set Up Email Alerts


$30,000,00030,000,000 - $140,845 /mo

Windermere - 9508 WINDY RIDGE RD

51,000 Sqr Feet

Private Windermere lakefront compound with 18 acres on Lake Down on the Butler Chain offering an unparalleled presence and prestige in Central Florida’s most desirable location. This walled and gated compound boasts a 25,000 sqft. state-of-the-art family residence, a 5,600 sqft grand lodge with ca...

6 beds + 13 baths + 51,000 sqft

$18,950,00018,950,000 - $88,967 /mo

Windermere

20,240 Sqr Feet

Presenting Central Florida’s most exquisite Lake Butler estate tucked behind the secured manned gates of Lake Butler Sound. Offering 20,240 sq ft under air (31,000 gross), on nearly 5 acres and 547 feet of lake frontage, this double-lot oasis offers a magnificent residence with multiple outdoor li...

9 beds + 15 baths + 20,240 sqft

$15,000,00015,000,000 - $70,422 /mo

Windermere - 5536 ISLEWORTH COUNTRY CLUB DR

13,519 Sqr Feet

Poised on a private cul-de-sac overlooking Isleworth’s 14th fairway and the beautiful Lake Butler, this island-inspired estate spans three home sites totaling 1.89 acres. The sprawling floor plan encompasses more than 13,000 square feet of living space, with elegant appointments throughout. The ...

7 beds + 9.5 baths + 13,519 sqft

$10,999,00010,999,000 - $51,638 /mo

Windermere - 5115 FAIRWAY OAKS DR

15,063 Sqr Feet

A sprawling floor plan and a prime setting on 3.76 acres along the shores of Lake Bessie define this exquisite seven-bedroom residence. Through a pair of arched French doors with glass and iron detail, the foyer opens to a stunning two-story living room where dramatic floor-to ceiling windows allow ...

7 beds + 9 baths + 15,063 sqft

$8,500,0008,500,000 - $39,906 /mo

Windermere - 5318 ISLEWORTH COUNTRY CLUB DR

11,182 Sqr Feet

Characterized by a lovely English garden designed to maximize its prime golf-front location, this estate is unparalleled in Isleworth. Beyond the circular driveway with fountain and porte-cochere entry, a pair of French doors open to the grand foyer featuring a curved staircase, wine cellar and poli...

6 beds + 8.5 baths + 11,182 sqft

$7,995,0007,995,000 - $37,535 /mo

Winter Park - 161 PALMER AVE

17,649 Sqr Feet

Fabulous contemporary lakefront estate on apprx 2 acres walking distance to downtown Winter Park… A contemporary paradise with panoramic views of Lake Maitland on the 6-lake Winter Park chain of lakes. Designed by NBA star Horace Grant, expanded by current owner, and featured in the Wall Street Jo...

7 beds + 9.5 baths + 17,649 sqft

$7,495,0007,495,000 - $35,188 /mo

Winter Park - 1202 N PARK AVE

8,766 Sqr Feet

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 unprecedented property is on a spacious ~1.25 acre double lot with 2 boathouses and...

6 beds + 8.5 baths + 8,766 sqft

$7,225,0007,225,000 - $33,920 /mo

Windermere - 5354 ISLEWORTH COUNTRY CLUB DR

9,811 Sqr Feet

Seller Requirement: Buyer must produce proof of funds at full listing price. Beautifully mirrored in Hourglass Pond, this home was designed to reflect the elegance of an old, Italian villa positioned on an oversized lot with more than an acre of lush, manicured gardens. Globally sourced materials, i...

5 beds + 6 baths + 9,811 sqft

$6,875,0006,875,000 - $32,277 /mo

Windermere - 5018 LATROBE DR

12,353 Sqr Feet

Gracious living at its finest, this exquisite French chateau offers a prime location overlooking the beautiful Lake Bessie within the renowned Isleworth Golf & Country Club. Elegant finishes, stonework and extensive marble throughout set the tone for the three-story home encompassing more than 12,3...

7 beds + 8.5 baths + 12,353 sqft

$6,795,0006,795,000 - $31,901 /mo

Winter Park - 1016 GENIUS DR

10,314 Sqr Feet

Incredible 2-acre Modern Mediterranean lakefront estate on hidden peninsula between Lake Mizell & Virginia on the 6-lake chain of lakes… Enjoy both picturesque sunrises & sunsets with Rollins College chapel and downtown Orlando illuminated in the evening. This property is on a private street with ...

6 beds + 8 baths + 10,314 sqft

$6,645,0006,645,000 - $31,197 /mo

Windermere

11,163 Sqr Feet

Seller Requirement: Buyer must produce proof of funds at full listing price. This commanding waterfront residence is elegantly situated on a picturesque home site along the shores of beautiful Lake Bessie. The six-bedroom home blends a Spanish Mediterranean exterior with a modern transitional inter...

6 beds + 7.5 baths + 11,163 sqft

$5,795,0005,795,000 - $27,207 /mo

Windermere - 5306 ISLEWORTH COUNTRY CLUB DR

8,802 Sqr Feet

Under construction. Designed by renowned architect Terry Irwin and currently being built by leading custom homebuilder Wyatt Construction, this two-story estate will offer five bedrooms and more than 8,800 square feet of living space. Nestled along the back nine within the gates of the renowned Is...

5 beds + 6.5 baths + 8,802 sqft

$5,750,0005,750,000 - $26,995 /mo

Windermere - 9832 LAUREL VALLEY DR

11,100 Sqr Feet

Unparalleled Isleworth estate with amazing views of Lake Butler combined with direct golf course frontage on Iselworth’s 15th hole. This one of a kind three story home is perched high above the famed Butler Chain of lakes offering incredible water views. Featuring 6 bedroom suites, a movie theater...

6 beds + 8.5 baths + 11,100 sqft

$5,495,0005,495,000 - $25,798 /mo

Windermere - 5300 ISLEWORTH COUNTRY CLUB DR

8,162 Sqr Feet

Under construction. Offering a prime location within the gates of the renowned Isleworth Golf & Country Club, this two-story estate will feature magnificent views of Holes 11 and 12, as well as Eagle Pond and open land showcasing one of Isleworth’s exquisite sculptures. Designed by renowned arch...

5 beds + 6 baths + 8,162 sqft

$5,495,0005,495,000 - $25,798 /mo

Winter Park - 1202 N PARK AVE

6,564 Sqr Feet

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 unprecedented property is on a spacious lot with frontage on Lake Maitland, this un...

4 beds + 6.5 baths + 6,564 sqft

$5,250,0005,250,000 - $24,648 /mo

Windermere - 9832 LAKE LOUISE DR

7,543 Sqr Feet

BEST PRICE PER SQ. ON THE BUTLER CHAIN IN THE COMMUNITY! Isleworth Lake Front Estate. Breathtaking views of Lake Louise, of the Butler Chain of Lakes, form almost every room in the house. This property was taken down to the studs in 2010 and was rebuilt with the finest materials and craftsmanship av...

4 beds + 5.5 baths + 7,543 sqft

$4,999,9994,999,999 - $23,474 /mo

Windermere - 5174 VARDON DR

10,701 Sqr Feet

Positioned on a corner home site within the renowned Isleworth Golf & Country Club, this beautiful estate offers a contemporary feel and neoclassical architectural styling. The interior spans more than 10,600 square feet, beginning in the two-story marble foyer with stone columns and a floating sta...

6 beds + 8 baths + 10,701 sqft

$4,995,0004,995,000 - $23,451 /mo

Winter Park - 1941 LEGION DR

10,493 Sqr Feet

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 & entertaining areas are spacious & elegant, w/ sweeping views of the lake from almost e...

6 beds + 8 baths + 10,493 sqft

$4,995,0004,995,000 - $23,451 /mo

Winter Park - 147 VIRGINIA DR

7,800 Sqr Feet

One of Winter Park’s most premier and timeless traditional lakefront estates elevated on apprx. 1.5 acres and 200’ of lake frontage on Lake Virginia walking distance to Rollins College and famed Park Avenue... The home was originally built in 1925, but the current owners completely renovated an...

5 beds + 6.5 baths + 7,800 sqft

$4,600,0004,600,000 - $21,596 /mo

Winter Park - 2040 VENETIAN WAY

7,677 Sqr Feet

Elegant Mediterranean Lakefront with over an acre of land in the “heart of Winter Park” With 227ft. of lakefront, the view is one of the most breathtaking on the Winter Park Chain. This 6 bedroom/7 ½ bath, pool home was designed by Slocum Platts Architects and built by Maroon Fine Homes. Lake v...

6 beds + 7.5 baths + 7,677 sqft

$4,495,0004,495,000 - $21,103 /mo

Windermere - 11536 LAKE BUTLER BLVD

8,051 Sqr Feet

Quite possibly the most serene & luxurious retreat on the Butler Chain of Lakes. Few homes compare to having approximately 550 feet of shoreline on Lake Butler, 8000+ square feet of low-country style living space, and a place to park your sea plane! Exquisite lake views are just the beginning of thi...

5 beds + 7 baths + 8,051 sqft

$4,250,0004,250,000 - $19,953 /mo

Winter Park - 916 PALMER AVE

4,259 Sqr Feet

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 Rollins College across the lake. This magnificent property boasts a stately two s...

5 beds + 4.5 baths + 4,259 sqft

$4,250,0004,250,000 - $19,953 /mo

Windermere - 6126 KIRKSTONE LN

8,379 Sqr Feet

Breathtaking lake front estate located in the 24 hour guard gated community of Lake Butler Sound. This luxurious home is the epitome of lake front living with an amazing corner lot and remarkable lake views from almost every room in the house. Owners will fall in love with the huge master suite feat...

5 beds + 6 baths + 8,379 sqft

$3,995,0003,995,000 - $18,756 /mo

Windermere - 9941 GROSVENOR POINTE CIR

7,400 Sqr Feet

Magnificent Mediterranean Mansion on Lake Tibet Butler in Keene's Pointe is simply a "Work of Art!" Intricate architectural style, coupled with interior finishes that rival mansions from around the globe, this estate features 4BR suites with 4 Full Baths plus 2 Half Baths, along with all the formal...

4 beds + 5 baths + 7,400 sqft


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Location & Address

Centurion Realty Group
6735 Conroy Windermere Rd, Suite 315
Orlando, FL
407-378-2775
4074430639