Homes for Sale near Windermere High School

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  /41

  $439,900

  • 3 Beds
  • 2.5 Baths
  • 1,617 Sq Ft

  5637 Water Rose Rd, Winter Garden, FL 34787

  Welcome to this beautifully maintained townhome located in the highly desirable Independence community.Built by Lennar Homes, this residence stands out with solid block construction on both the first and second floors—a rare and valuable feature, as many townhomes in the neighborhood provides block construction only on the first level. The home features a bright, open, and spacious floor

  Luciana Amorim Panajotti FLORIDA CONNEXION PROPERTIES

  5637 Water Rose Rd, Winter Garden, FL 34787
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  /52

  $2,390,000

  • 5 Beds
  • 4 Baths
  • 4,287 Sq Ft

  6252 Blakeford Dr, Windermere, FL 34786

  Now it’s your turn to live on the 18th hole of the Golden Bear Club golf course in a fully updated custom home, located on one of the most desirable streets in Keene’s Pointe. This house with a timeless design inside and out, has five bedrooms (two down and three up), four full bathrooms, three car garage, and incredible outdoor living with renovated pool and brand new pool enclosure. Upstairs

  Shane Croft COLDWELL BANKER RESIDENTIAL RE

  6252 Blakeford Dr, Windermere, FL 34786
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  /80

  $889,000

  • 5 Beds
  • 4 Baths
  • 3,289 Sq Ft

  4937 Wildwood Pointe Rd, Winter Garden, FL 34787

  Welcome to this spacious and beautifully maintained 5-bedroom, 4-bathroom home in the desirable Winter Garden area. Situated on a premium lot with no rear neighbors, this home backs onto a peaceful preserve, offering privacy and natural views. The open-concept layout features a large kitchen with granite countertops, stainless steel appliances, and a center island—perfect for cooking and

  Yadira Olivo OLIVO REALTY GROUP, LLC

  4937 Wildwood Pointe Rd, Winter Garden, FL 34787
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  /49

  $1,289,999

  • 5 Beds
  • 4 Baths
  • 3,358 Sq Ft

  11524 Claymont Cir, Windermere, FL 34786

  ***PRICE IMPROVEMENT, SELLER MOTIVATED!*** Completely updated in recent years, this 5-bedroom, 4-bath residence offers 3,358 square feet of thoughtfully designed living space in Keene’s Pointe, Windermere’s premier 24-hour guard-gated community and home to the Golden Bear Club. An oversized driveway with parking for up to nine vehicles, along with a three-car garage, creates a strong first

  Immu Korvenmaa ALIGN REAL ESTATE LLC

  11524 Claymont Cir, Windermere, FL 34786
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  /19

  $3,000,000

  • Land
  • 1.02 Acres
  • $2,941,176 per Acre

  12213 Park Ave, Windermere, FL 34786

  Welcome to Chaine Du Lac- one of Windermere's most exclusive gated enclaves. This prime 1.02-acre cul-de-sac lot is one of only TWO homesites remaining among just 44 custom-built estate residences, offering a rare opportunity to design your private luxury retreat. The property is cleared, level, and fully equipped with utilities, making it truly build-ready. Enjoy the tranquility of oversized

  Naresh Budhu PREMIUM PROPERTIES R.E. SERVICE

  12213 Park Ave, Windermere, FL 34786
• 

  $510,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,649 Sq Ft

  Cypress Plan at Lake Cawood Cove - Townhomes, Windermere, FL 34786

  Ashton Woods Builder

  5432 Winter Garden Vineland Rd Unit 37932786, Windermere, FL 34786
• 

  

  /19

  $834,000

  • 4 Beds
  • 3.5 Baths
  • 3,068 Sq Ft

  6631 Crestmont Glen Ln Unit 1, Windermere, FL 34786

  New price reflects a fantastic opportunity for today’s buyers. Welcome to 6631 Crestmont Glen Lane, a stunning executive home nestled in the highly sought-after gated community of Glenmuir in Windermere, Florida. This beautifully maintained residence offers the perfect blend of comfort, elegance, and functionality on a spacious, landscaped lot.Featuring 4 bedrooms and 3 1/2 bathrooms, this home

  Gonzalo Senior IRM INVEST., REAL EST.& MGMT.

  6631 Crestmont Glen Ln Unit 1, Windermere, FL 34786
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  /39

  $830,000

  • 6 Beds
  • 5.5 Baths
  • 3,698 Sq Ft

  4345 Saltmarsh Sparrow Dr, Windermere, FL 34786

  Welcome HOME to Summerport! This stunning fully indoor and outdoor repainted 6-bedroom, 5.5-bathroom residence is now listed for sale in the highly desirable Summerport neighborhood—zoned for top-rated A+ schools! Step inside and enjoy a thoughtfully designed split two-story floor plan with plenty of room for family and entertaining. The first floor features a versatile office/den with French

  Silvia Odebrecht ICON REALTY ASSOCIATES INC

  4345 Saltmarsh Sparrow Dr, Windermere, FL 34786
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  /56

  $565,000

  • 4 Beds
  • 2.5 Baths
  • 2,460 Sq Ft

  6718 Romney Ln, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Well-maintained 4-bedroom, 2.5-bath home in the heart of Windermere featuring inviting curb appeal with a covered front porch and classic columns. The bright, open layout offers high ceilings, crown molding, and tile and wood-look flooring throughout the main living areas. The kitchen includes dark wood cabinetry, granite countertops, stainless

  Tyler Gibson LPT REALTY, LLC

  6718 Romney Ln, Windermere, FL 34786
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  /62

  $625,000

  • 4 Beds
  • 3 Baths
  • 2,204 Sq Ft

  5531 Cypress Hill Rd, Winter Garden, FL 34787

  Exquisitely upgraded 4-bedroom, 3-bath smart home in the highly sought-after Orchard Hills community of Winter Garden. Situated on a premium lot with no rear neighbors, this move-in-ready home offers a peaceful pond view and exceptional privacy. Soaring ceilings, elegant 20" tile flooring, and abundant natural light enhance the open-concept design. The designer kitchen features upgraded mocha

  Olga Kaza OLYMPUS EXECUTIVE REALTY INC

  5531 Cypress Hill Rd, Winter Garden, FL 34787
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  /40

  $625,000

  • 3 Beds
  • 2 Baths
  • 2,077 Sq Ft

  6315 Clearmeadow Ct, Windermere, FL 34786

  ***PRESIDENT'S MONTH SPECIAL 20k towards closing on a full price accepted offer during the month of February.***This must-see home is ready to welcome you to the exclusive and upscale gatedsubdivision of Glenmuir. This spacious property is in an A-rated school district justminutes from Disney, Universal, Sea World, Downtown Windermere, and WinterGarden. Located on a quiet

  Drew Wolski CORE REAL ESTATE GROUP

  6315 Clearmeadow Ct, Windermere, FL 34786
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  /64

  $4,495,000

  • 5 Beds
  • 7 Baths
  • 5,895 Sq Ft

  6109 Orta Ct, Windermere, FL 34786

  Within the gates of the Waterstone community, this exceptional lakefront estate offers approximately 5,895 square feet of refined living space, seamlessly blending modern elegance with timeless sophistication. The thoughtfully designed floor plan features five bedrooms, five full bathrooms, and two half bathrooms, with the primary suite conveniently located on the main level.At the heart of

  Monica Lochmandy ISLEWORTH REALTY LLC

  6109 Orta Ct, Windermere, FL 34786
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  /75

  $3,600,000

  • 5 Beds
  • 6.5 Baths
  • 5,501 Sq Ft

  5024 Sawyer Cove Way, Windermere, FL 34786

  Welcome to “The Sounding:” a captivating lakefront estate residence with inviting water views and a serene and peaceful setting offering the best of Florida living. Tucked inside this privately gated and intimate enclave of estate homes across the street from Windermere Prep, Sawyer Sound offers an escape from the ordinary and this showplace residence sets the standard for lakefront living. A

  Rob Rahter STOCKWORTH REALTY GROUP

  5024 Sawyer Cove Way, Windermere, FL 34786
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  /36

  $759,000 Open Sun 11AM - 1PM

  • 5 Beds
  • 3.5 Baths
  • 2,888 Sq Ft

  11525 Chateaubriand Ave, Orlando, FL 32836

  Impeccably renovated five-bedroom, three-and-a-half-bath residence in one of Orlando’s desirable, family-friendly communities. This exceptional home seamlessly blends timeless elegance with modern comfort throughout. The open-concept design highlights a beautifully updated kitchen and family room with breakfast bar and dual pantries, ideal for everyday living and refined entertaining. A formal

  Kimberly Tessitore PREMIER SOTHEBY'S INTL. REALTY

  11525 Chateaubriand Ave, Orlando, FL 32836
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  /64

  $2,145,000

  • 4 Beds
  • 4.5 Baths
  • 4,013 Sq Ft

  6036 Greatwater Dr, Windermere, FL 34786

  Welcome to Keene’s Pointe! Discover the charm of this custom-built home located on the 17th Fairway of the renown Jack Nicklaus Signature Golf Course and across from the lakefront mansions that line this quiet cul-de- sac on Greatwater Drive. This 4BR/4Full Bath/1 Half Bath golf course estate home exudes warmth from the gorgeous hardwood floors and abundant natural light. You will find your main

  Angela Durruthy KEENE'S POINTE REALTY

  6036 Greatwater Dr, Windermere, FL 34786
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  /22

  $580,000

  • 4 Beds
  • 3.5 Baths
  • 2,551 Sq Ft

  8533 Greenbank Blvd, Windermere, FL 34786

  Roof is 2022, A beautiful Home in a wonderful Gated Community in Windermere. Home sits on a big lot that extends all the way to the high tree, and it has fruit trees, avocado, and mango. Home is very spacious with Master downstairs, one owner, the upper floor was not even being used by seller. Come see this beauty, priced to sell. Motivated Seller, please bring your offers.

  Faneeza Mohamed CENTURY 21 CARIOTI

  8533 Greenbank Blvd, Windermere, FL 34786
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  /69

  $870,000

  • 5 Beds
  • 4.5 Baths
  • 3,312 Sq Ft

  13106 Orange Isle Dr, Windermere, FL 34786

  Explore the WINTERSET model from Ryan Homes of the Sanctuary at Lakes of Windermere, a corner unit, this 5- bedroom, 4.5 bathroom in Windermere combines the modern elegance, and a touch of magic with its a DISNEY Fireworks view, offering a lifestyle of unparalleled comfort. Upon entering, you are greeted by those who appreciate a dedicated workspace, the home includes a spacious office and a

  Gladys Bezerra FLORIDA CONNEXION PROPERTIES

  13106 Orange Isle Dr, Windermere, FL 34786
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  /38

  $10,250,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 6,590 Sq Ft

  10160 Autumn Mist Ln Unit 601, Orlando, FL 32836

  Under Construction. A new luxury Four Seasons Private Residences opportunity is now available at Golden Oak at Walt Disney World® Resort. The proposed project by HHR FSO LAND LLC will feature a collection of nine attached boutique homes and 31 luxe residences, including five stunning multi-level penthouses, all within a single, elevated residential address. Designed for hotel-inspired living at a

  Karen Balcerak GOLDEN OAK REALTY

  10160 Autumn Mist Ln Unit 601, Orlando, FL 32836
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  /34

  $320,000

  • 3 Beds
  • 2.5 Baths
  • 1,460 Sq Ft

  8259 Maritime Flag St Unit 4, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Experience the best of Windermere living! This freshly updated two-story townhome offers resort-style amenities and unbeatable convenience, all just 10 minutes from Disney! Step inside to discover fresh paint throughout, brand new carpet, and an open-concept first floor with a kitchen/living room combo and a half bath. Upstairs, you’ll find three

  Lindsey Hudson REAL BROKER, LLC.

  8259 Maritime Flag St Unit 4, Windermere, FL 34786
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  /39

  $550,000

  • 3 Beds
  • 2 Baths
  • 2,120 Sq Ft

  3242 Irish Peach Dr, Winter Garden, FL 34787

  Exquisite Three-Bedroom Home with Flex Room in a Gorgeous CommunityNestled in one of the most desirable communities, this stunning three-bedroom, two-bathroom home offers the perfect blend of luxury, comfort, and modern living. Designed with an elegant open floor plan, this residence is bathed in natural light, seamlessly connecting the spacious living, dining, and kitchen areas ! ideal for

  Erica Ally LPT REALTY, LLC

  3242 Irish Peach Dr, Winter Garden, FL 34787
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  /3

  $1,118,989 New Construction

  • 4 Beds
  • 3 Baths
  • 2,687 Sq Ft

  Arlington Plan at Palms at Windermere, Windermere, FL 34786

  Welcome to the Arlington! This single-story floor plan features 3-4 bedrooms, 3 bathrooms, and a 2-car garage, offering 2,687 square feet of spacious living. Enjoy an open-concept design that seamlessly connects the dining, kitchen, and living areas. The garage also includes an extra hobby/work space. Relax on the large covered patio or create culinary masterpieces in the chef's kitchen. The

  Dream Finders Homes Builder

  14207 Crest Palm Ave Unit 36498773, Windermere, FL 34786
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  /91

  $1,075,000

  • 4 Beds
  • 4 Baths
  • 4,232 Sq Ft

  9331 Royal Estates Blvd, Orlando, FL 32836

  PRICE IMPROVED !!! Welcome to Royal Estates, one of the most reputable and desirable communities near Windermere, where you can enjoy the breathtaking Disney World fireworks from the privacy of your own backyard. This luxurious two-story residence, built in 2018 by Pulte Homes, exemplifies refined elegance, superior craftsmanship, and an array of high-end upgrades throughout. The grand foyer &

  Sam Fernandes FLORIDA CONNEXION PROPERTIES

  9331 Royal Estates Blvd, Orlando, FL 32836
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  /68

  $7,900,000

  • 5 Beds
  • 7 Baths
  • 4,649 Sq Ft

  10164 Carthay Dr, Golden Oak, FL 32836

  Welcome to Caledonia — a breathtaking custom estate by Cahill Homes, ideally positioned in the heart of Golden Oak at Walt Disney World® Resort. This exceptional residence offers 5 bedrooms, 5 full and 2 half baths, with every bedroom featuring its own en-suite bath, blending refined luxury with whimsical Disney detailing throughout. The home’s expansive open-concept design centers around a

  Tansey Soderstrom REAL ESTATE FIRM OF ORLANDO

  10164 Carthay Dr, Golden Oak, FL 32836
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  /30

  $1,050,000

  • 5 Beds
  • 3.5 Baths
  • 3,820 Sq Ft

  6752 Trellis Vine Loop, Windermere, FL 34786

  Designed for those who crave space, privacy, and elevated living, this exceptional newer home offers 5 BEDROOMS PLUS TWO BONUS ROOMS, including ALL 4 MAIN BEDROOMS with WALK-IN CLOSETS and a private guest suite featuring an EN-SUITE and WALK-IN CLOSET—all complemented by NO REAR NEIGHBORS and NO FRONT NEIGHBORS, creating extraordinary flexibility for refined living, entertaining, and everyday

  Candice Collins COLDWELL BANKER REALTY

  6752 Trellis Vine Loop, Windermere, FL 34786
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  /90

  $2,600,000

  • 5 Beds
  • 7 Baths
  • 5,366 Sq Ft

  6288 Blakeford Dr, Windermere, FL 34786

  Golfers, entertainers, and chefs- this is the home that checks every box. Perfectly positioned on the 18th tee box of the Golden Bear Golf & Country Club, this move-in ready, three-story five-bedroom, four full and three half bath custom residence is one of the most unique properties in all of Keene’s Pointe.Located within the highly coveted 24-hour guard-gated community, residents have the

  Ken Pozek REAL BROKER, LLC.

  6288 Blakeford Dr, Windermere, FL 34786
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  /70

  $1,275,000

  • 4 Beds
  • 3 Baths
  • 3,021 Sq Ft

  11334 Camden Loop Way, Windermere, FL 34786

  Nestled within the guard-gated community of Keene’s Pointe, this beautifully updated single-story home offers a well-designed, functional layout with tasteful upgrades throughout. Recent improvements include luxury vinyl flooring, updated lighting, fresh interior and exterior paint, and a new roof installed in 2024, making the home truly move-in ready. The open-concept kitchen and family room are

  Rob Rahter STOCKWORTH REALTY GROUP

  11334 Camden Loop Way, Windermere, FL 34786
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  /69

  $970,000 Open Sun 10:30AM - 12:30PM

  • 5 Beds
  • 5.5 Baths
  • 3,680 Sq Ft

  6947 Cucamelon Ct, Windermere, FL 34786

  PRICE IMPROVEMENT — exceptional value in Windermere! Welcome home to your personal oasis — tucked within the prestigious Sanctuary at Lakes of Windermere, this move-in-ready retreat is designed for inspired living and effortless entertaining. From the moment you step inside, you’ll feel how the open, airy layout and thoughtful finishes create a haven you can’t wait to come home to. With five full

  Mahmoud Mango DALTON WADE INC

  6947 Cucamelon Ct, Windermere, FL 34786
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  /39

  $419,000

  • 3 Beds
  • 2.5 Baths
  • 1,583 Sq Ft

  12944 Garridan Ave, Windermere, FL 34786

  Welcome to this well-maintained 3-bedroom, 2.5-bath home offering 1,583 square feet of comfortable living space in the well established Wickham Park community. The home is in excellent condition and has been thoughtfully cared for, making it truly move-in ready. Enjoy low-maintenance living with an HOA that covers exterior maintenance for normal wear and tear, including roof, exterior painting,

  Fred Jackson 407 PROPERTIES

  12944 Garridan Ave, Windermere, FL 34786
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  /50

  $749,900

  • 4 Beds
  • 3 Baths
  • 2,622 Sq Ft

  11450 Arborside Bend Way, Windermere, FL 34786

  Beautifully maintained 4BR/3BA pool home in gated Glenmuir, Windermere. Open floor plan with high ceilings, formal dining, and spacious family room. Kitchen with breakfast nook overlooks screened pool/lanai. Primary suite features dual closets, spa bath, and pool access. Home includes water softener system, water heater from 2022 and air handler from 2020. Enjoy a private 0.25-acre lot in a

  David Sanchez LOKATION

  11450 Arborside Bend Way, Windermere, FL 34786
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  /68

  $1,975,000

  • 4 Beds
  • 4.5 Baths
  • 4,550 Sq Ft

  12235 Montalcino Cir, Windermere, FL 34786

  Casa del Lago gated community in Windermere, Florida. Exquisite 4 bedroom/4.5 bath luxury residence showcasing exceptional craftsmanship and high-end finishes throughout. As you arrive you are welcomed by a circular driveway and quaint courtyard entrance. The first floor boasts a formal dining room,and a spacious gathering room anchored by a stunning stone two-sided fireplace. A dedicated

  Teresa Stewart SOUTHERN REALTY GROUP LLC

  12235 Montalcino Cir, Windermere, FL 34786
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  /47

  $595,000

  • 4 Beds
  • 3.5 Baths
  • 2,628 Sq Ft

  8650 Abbotsbury Dr, Windermere, FL 34786

  Welcome to this beautifully maintained 4-bedroom, 3.5-bath residence located in the sought-after, gated Lakes of Windermere community. This two-story home offers peace of mind with a brand-new roof installed in 2025 and features a light-filled, open-concept layout designed for both everyday living and entertaining. The main level includes formal living and dining spaces, a generous family room, a

  Andy Neal THE AGENCY FL

  8650 Abbotsbury Dr, Windermere, FL 34786
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  /40

  $664,900

  • 4 Beds
  • 2.5 Baths
  • 2,908 Sq Ft

  6638 Bridgewater Village Rd, Windermere, FL 34786

  Welcome to Vineyards Horizon West, this stunning 4-bedroom, 2.5-bath home offers about 3,000 square feet of thoughtfully designed living space, all set on a large conservation lot that ensures privacy and tranquility. From the moment you step inside, you will fall in love with the abundance of natural light, highlighting the home's open and airy layout. Downstairs, a versatile flex space awaits

  Nickolas Amburgey COMPASS FLORIDA LLC

  6638 Bridgewater Village Rd, Windermere, FL 34786
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  /89

  $2,499,000

  • 4 Beds
  • 5.5 Baths
  • 4,810 Sq Ft

  6102 S Hampshire Ct, Windermere, FL 34786

  This elegant single-story Rick Watson home, located at 6102 S Hampshire Court, Windermere, FL 34786, sits on a private Jack Nicklaus–designed golf course lot in the exclusive, 24-hour manned and gated community of Keene’s Pointe. Enjoy uninterrupted views of the 6th hole by day and Disney Fireworks at night from key living areas and the outdoor lanai. The home features 4 bedrooms, 5 bathrooms, a

  Jessica Dessire Cueva PA CHARLES RUTENBERG REALTY ORLANDO

  6102 S Hampshire Ct, Windermere, FL 34786
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  /58

  $634,900 Open Sun 1PM - 4PM

  • 5 Beds
  • 3.5 Baths
  • 2,396 Sq Ft

  11578 Ashlin Park Blvd, Windermere, FL 34786

  Welcome to this stunning 5-bedroom, 3.5 bath single-family home located in the highly desirable Ashlin Park community of Windermere. Designed with both style and functionality in mind, this open-concept home features a spacious kitchen with quartz countertops, ample cabinetry, and a walk-in pantry, perfect for entertaining and everyday living. The fenced backyard offers low-maintenance synthetic

  Erika Garcia CENTURY 21 CARIOTI

  11578 Ashlin Park Blvd, Windermere, FL 34786
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  /45

  $8,995,000

  • 5 Beds
  • 8 Baths
  • 5,475 Sq Ft

  10443 Los Feliz Dr, Orlando, FL 32836

  Located in Golden Oak at Walt Disney World® Resort, Covina is a masterfully craftedestate that redefines luxury living, offering an extraordinary and immersive lifestyle justmoments from the magic of Walt Disney World. Upon arrival, the home makes a strikingfirst impression with its refined façade and elegant entry, leading into a breathtakingliving space defined by soaring

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  10443 Los Feliz Dr, Orlando, FL 32836
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  /68

  $950,000

  • 5 Beds
  • 3.5 Baths
  • 3,407 Sq Ft

  12530 Climbing Vine Ct, Windermere, FL 34786

  Tucked at the end of a quiet cul-de-sac in the sought after community of Windstone, this beautifully appointed Windermere residence offers a lifestyle centered on comfort, connection, and effortless everyday luxury. Designed with both relaxation and entertaining in mind, the home welcomes you with an open layout filled with natural light and refined finishes that elevate each space. The main

  Andy Neal THE AGENCY FL

  12530 Climbing Vine Ct, Windermere, FL 34786
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  /54

  $680,000

  • 4 Beds
  • 2.5 Baths
  • 2,947 Sq Ft

  13339 Roskin Ln, Windermere, FL 34786

  Welcome to an exceptional opportunity in one of Central Florida’s most sought-after areas. This ginormous 4 bedroom, 2.5 bath, two story home offers 2,947 square feet of versatile living space designed for comfort, entertaining, and everyday luxury. The layout is ideal, featuring a private den/office, a massive upstairs loft, and generously sized bedrooms throughout. The primary suite is a true

  Karla Price COLDWELL BANKER REALTY

  13339 Roskin Ln, Windermere, FL 34786
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  /71

  $3,495,000

  • 6 Beds
  • 5.5 Baths
  • 6,000 Sq Ft

  5538 W Lake Butler Rd, Windermere, FL 34786

  Welcome to 5538 W Lake Butler Road—an expansive, newly renovated estate set on 1.9 acres of lush, lakefront land in arguably one of Central Florida’s most coveted locations, Kelso on Lake Butler. What distinguishes this property is its remarkable dual lake access. Your own private boat dock provides direct skiable waterfront on Lake Davis, while exclusive community privileges grant you gated

  Julie Bettosini STOCKWORTH REALTY GROUP

  5538 W Lake Butler Rd, Windermere, FL 34786

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