Orlando Real Estate Pros



Refine SearchProperty Search








801 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

20,333 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 + 20,333 sqft

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

Windermere - 5536 ISLEWORTH COUNTRY CLUB DR

13,519 Sqr Feet

Spanning more than 13,000 square feet on a private cul-de-sac overlooking Isleworth’s 14th fairway and Lake Butler, this island-inspired estate boasts a sprawling floor plan with elegant appointments throughout. The resplendent interior showcases formal living and dining rooms, each accented by e...

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

$11,900,00011,900,000 - $55,868 /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

$8,900,0008,900,000 - $41,784 /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

$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

$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

$7,500,0007,500,000 - $35,211 /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

$6,995,0006,995,000 - $32,840 /mo

Winter Park - 1016 GENIUS DR

10,314 Sqr Feet

As beautiful inside as it is outside, this magnificent one-of-a-kind lakefront estate is located in the Gated Estate Section of Windsong, one of Winter Park's most desirable addresses. This custom one-owner home was built in 2005 by award-winning Rial Jones and designed by Bernie Johnson. The 2+ acr...

6 beds + 8 baths + 10,314 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

$6,200,0006,200,000 - $29,108 /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

$5,995,0005,995,000 - $28,145 /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

$5,799,0005,799,000 - $27,225 /mo

Windermere - 9832 LAKE LOUISE DR

7,543 Sqr Feet

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 available. 2 gourmet kitchens. One inside and one outside....

4 beds + 5.5 baths + 7,543 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

$5,695,0005,695,000 - $26,737 /mo

Winter Park - 147 VIRGINIA DR

7,800 Sqr Feet

Majestic Winter Park Estate on 1.59 acres of pristine lakefront property. Panoramic views of Lake Virginia from every corner of this stunning home. Private driveway with electronic gate, motor court, four car garage, guest house, boathouse, and more. Sophisticated and elegant, the main house offers ...

5 beds + 6.5 baths + 7,800 sqft

$5,095,0005,095,000 - $23,920 /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 almos...

6 beds + 8 baths + 10,493 sqft

$4,800,0004,800,000 - $22,535 /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

$4,695,0004,695,000 - $22,042 /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 + 6.5 baths + 8,051 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

Windermere - 6113 GROSVENOR SHORE DR

8,677 Sqr Feet

STUNNING STATE-OF-ART LAKEFRONT HOME located in KEENE'S POINTE*** This amazing home was designed to entertain even for very large families, and features 7 bedrooms, 6 full and 2 half bathrooms. Besides a formal living room with a breathtaking view from Lake Butler, this home also offers a formal d...

7 beds + 7 baths + 8,677 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


  Next

Found 801 Properties

1-24 | 25-48 | 49-72 | 73-96 | 97-120 | 121-144 | 145-168 | 169-192 | Last

Saved Properties

This is a list of your favorite properties. We will email you if a property is reduced or leaves the market.

Click 'Save' to add a property to this list.

Register / Login

New & returning visitors please enter your information to login.

By clicking 'register' you are agreeing to our terms of use & giving us expressed written consent to contact you.

Questions? Comments? Complaints?

This message will go directly to the head of our team.

Location & Address

R Associates - RE/MAX Elite
4243 NE Lakewood Way Lees
Summit, MO
816-678-0050