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784 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

$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

$13,500,00013,500,000 - $63,380 /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 - 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

$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

$8,490,0008,490,000 - $39,859 /mo

Winter Park - 161 PALMER AVE

17,649 Sqr Feet

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 the Wall Street Journal, this iconic estate is just a short walk to trendy Park ...

7 beds + 9.5 baths + 17,649 sqft

$7,900,0007,900,000 - $37,089 /mo

Windermere - 11301 BRIDGE HOUSE RD

10,155 Sqr Feet

Every once in a while an enclosure is created that crosses the line; ceasing to be solely a structure, but rather architecture, art. A place where aesthetics, form and function converge harmonically to inspire a visceral experience so exceptional, it alters emotion. Enter “Overjoy.” Located ...

5 beds + 8 baths + 10,155 sqft

$7,900,0007,900,000 - $37,089 /mo

Winter Park - 1202 N PARK AVE

8,767 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 + 8,767 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

$6,645,0006,645,000 - $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

$6,500,0006,500,000 - $30,516 /mo

Windermere - 6005 CARTMEL LN

15,332 Sqr Feet

The private Cartmel castle estate is situated on 3.44 acres with 648 ft. frontage on famed Lake Butler. Located in 24 hour guard gated Reserve at Lake Butler Sound. This expansive estate offers 6 bedrooms, 6 full baths and 2 half baths with 15,332 sf under air and 20,763 under roof with a 5 car gara...

6 beds + 7 baths + 15,332 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 - 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

$5,500,0005,500,000 - $25,822 /mo

Windermere - 5180 VARDON DR

11,340 Sqr Feet

This superior estate offers more than 11,000 square feet with panoramic views of Isleworth’s renowned golf course. Spacious, elegant living spaces offer impeccable design and superb luxuries along with a sprawling floor plan brimming with exquisite finishes. The rich ambiance of the 5-bedroom es...

5 beds + 6.5 baths + 11,340 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

$4,950,0004,950,000 - $23,239 /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

$4,550,0004,550,000 - $21,361 /mo

Windermere - 9905 LAKE LOUISE DR

7,122 Sqr Feet

This sprawling Tuscan-inspired estate provides an unparalleled venue for indoor-outdoor entertaining with a backdrop of sweeping fairway views. The entrance features a floating staircase leading to superb living areas including three large en-suite bedrooms. The formal dining room with ceiling detai...

4 beds + 6.5 baths + 7,122 sqft

$4,300,0004,300,000 - $20,188 /mo

Winter Park - 1830 GIPSON GREEN LN

6,850 Sqr Feet

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 detail has been missed. Stunning Foyer w/Onyx and Marble floors leads to breathtaking...

5 beds + 6 baths + 6,850 sqft

$4,300,0004,300,000 - $20,188 /mo

Windermere - 9241 TIBET POINTE CIR

9,207 Sqr Feet

Stunning French country estate located in the exclusive guard gated community of Keene’s Pointe. Luxury and elegance resonate throughout this magnificent residence. From the two story stone fireplace flanked by floor to ceiling windows to the exquisite ceiling details and beautiful tile inlays, th...

5 beds + 6.5 baths + 9,207 sqft

$4,295,0004,295,000 - $20,164 /mo

Windermere - 6139 GREATWATER DR

8,057 Sqr Feet

Lakefront - Golf and country club gated community! Everything beautiful-Views-Floor Plan–Craftsmanship and amenity-rich-including an Elevator! Custom built for current owner with a strong emphasis on timeless architecture, quality construction, and a commitment to a functional floor plan that will...

4 beds + 5.5 baths + 8,057 sqft

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

Winter Park - 1000 GENIUS DR

8,157 Sqr Feet

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 their clubhouse, but was sold as a private residence soon after completion. Owne...

5 beds + 6 baths + 8,157 sqft

$4,195,0004,195,000 - $19,695 /mo

Windermere - 6037 GREATWATER DR

7,884 Sqr Feet

Extraordinary French Country Estate on the Butler Chain of Lakes in desirable Keene’s Pointe, Windermere, FL. Spanning over 7800 SF, this magnificent waterfront residence welcomes you to an elegant living area with a dramatic focal point of the tropical salt water pool surrounded by waterfalls and...

5 beds + 5.5 baths + 7,884 sqft

$4,000,0004,000,000 - $18,779 /mo

Windermere

9,594 Sqr Feet

LAKE BUTLER CHAIN OF LAKES ESTATE HOME. Fully furnished, lake front, two story home is located in the guard gated community of "The Reserve at Butler Sound" providing over 9,000 SF of lake front luxury living. Custom stone flooring crafted woodwork, sunken wine vault, formal dining room, formal of...

7 beds + 8.5 baths + 9,594 sqft

$3,900,0003,900,000 - $18,310 /mo

Winter Park - 1637 CHASE LANDING WAY

6,272 Sqr Feet

Come see this extraordinary Lakefront Estate in premier neighborhood of Windsong Preserve Point. This stunning home features 100' frontage on Lake Berry. It was completely remodeled with the finest of materials. The gourmet kitchen features top of line built in appliances and oversized granite is...

5 beds + 5.5 baths + 6,272 sqft


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Location & Address

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