Houses for Sale near Olympia High

/39
$2,150,000
- 3 Beds
- 3 Baths
- 2,681 Sq Ft
647 Ridgewood Dr, Windermere, FL 34786

One or more photo(s) has been virtually staged. Back on market — buyer’s home sale contingency did not clear. Inspection and appraisal were completed satisfactorily, no fault of the seller or property. Welcome to an extraordinary lakefront retreat on the prestigious Butler Chain of Lakes in Windermere. On a rare 1.43-acre double lot with over 200 feet of prime shoreline on Lake Down, this

Linda O'Grady

PREMIER SOTHEBYS INT'L REALTY

(689) 302-3809

647 Ridgewood Dr, Windermere, FL 34786
Explore Olympia High
/34
$645,000
- 4 Beds
- 2 Baths
- 2,287 Sq Ft
8449 Island Palm Cir, Orlando, FL 32835

Welcome to this inviting four-bedroom, two-bathroom pool home in the Palm Cove Estatescommunity, just minutes from Dr. Phillips and Windermere. From the moment you arrive, thehome’s impressive curb appeal and lush landscaping set the tone for what’s inside—a bright,comfortable space designed for everyday living and effortless entertaining.Step through the double entry front doors

Tiffany Pantozzi

ALIGN REAL ESTATE LLC

(321) 515-5143

8449 Island Palm Cir, Orlando, FL 32835
/42
$1,225,000
- 5 Beds
- 4.5 Baths
- 3,190 Sq Ft
2828 Ingeborg Ct, Windermere, FL 34786

Welcome to this Mediterranean dream home tucked away at the end of a quiet cul-de-sac in Windermere, just steps from beautiful Lake Down. Sitting on over an acre of fenced land, this property is one of the most unique opportunities in the area. From the moment you arrive, the curb appeal stands out with a circular driveway that flows into a full side driveway leading to an oversized detached

Tiffany Pantozzi

ALIGN REAL ESTATE LLC

(689) 314-6947

2828 Ingeborg Ct, Windermere, FL 34786
/39
$1,000,000
- 4 Beds
- 4 Baths
- 3,603 Sq Ft
2237 Baesel View Dr, Orlando, FL 32835

Experience timeless elegance in this Mediterranean-inspired residence, located in the gated golf course community of Palma Vista. From the grand foyer to the hand-carved Cherrywood parlor, every detail reflects craftsmanship and sophistication. With a built-in wine refrigerator and media center, this home was designed for effortless entertaining. The open chef’s kitchen flows into a sunlit family

Shandy Ortiz

PREMIER SOTHEBYS INT'L REALTY

(321) 399-5609

2237 Baesel View Dr, Orlando, FL 32835
/63
$1,237,000
- 4 Beds
- 3.5 Baths
- 2,791 Sq Ft
109 E 12th Ave, Windermere, FL 34786

Modern upgrades meet timeless Windermere charm in this fully reimagined four-bedroom, three-and-a-half-bath home, just steps from Lake Bessie. Set on a beautifully manicured corner lot with no HOA, this thoughtfully updated property blends luxury, comfort, and functionality in one of Central Florida’s most desirable communities. Every detail has been considered—NEW ROOF, NEW A/C, NEW PLUMBING,

Robert Larkan EXECUTIVE PROPERTIES

109 E 12th Ave, Windermere, FL 34786
/55
$2,375,000
- 5 Beds
- 4.5 Baths
- 4,688 Sq Ft
409 W 2nd Ave, Windermere, FL 34786

Step inside this beautifully updated home where clean lines, soaring ceilings, and two-story windows fill every corner with natural light. A floating staircase makes a stunning first impression, while the spacious family room with its cozy fireplace is the perfect spot to gather with friends and family.The open living and dining room features built-ins with floating shelves, and the gourmet

Amanda Black UPSIDE REAL ESTATE INC

409 W 2nd Ave, Windermere, FL 34786
/50
$885,000
- 2 Beds
- 1.5 Baths
- 2,115 Sq Ft
416 Magnolia St, Windermere, FL 34786

Step into a storybook cottage tucked in the heart of Windermere, where history whispers through every room and morning light dances across original 1915 details. Part of the early homestead still remains, giving this home a charm that simply can’t be recreated.The family room feels like a cozy tale come to life with its high ceilings, original wood floors, beadboard ceiling, and brick

Judy Black UPSIDE REAL ESTATE INC

416 Magnolia St, Windermere, FL 34786
/59
$1,100,000
- 4 Beds
- 3.5 Baths
- 3,515 Sq Ft
5203 Hillview Ln, Orlando, FL 32819

One or more photo(s) has been virtually staged. Enter into a 20' foyer with 2 large pocket doors open to the Saltwater pool with mature landscaping, windows, and light everywhere. This was a former model home. Located on the corner of a cul-de-sac lot, a .5 lot with a side entry 3-car garage, and an open kitchen with an island overlooking the family room. There is a huge breakfast room that

Dennis Kinkopf BETTER HOMES & GARDENS REAL ESTATE LIFESTYLES REALTY

5203 Hillview Ln, Orlando, FL 32819
/87
$2,500,000
- 5 Beds
- 4.5 Baths
- 4,284 Sq Ft
81 Oakdale St, Windermere, FL 34786

Gorgeous canal-front home with direct access to the Butler Chain of Lakes and just four blocks from the heart of downtown Windermere, this 2024 luxury remodel offers the perfect blend of modern living and small-town charm. Minutes from Food Truck Fridays, local cafés, parks, tennis courts, and year-round community events, this home blends modern elegance with the warmth of small-town living. Step

Billinda Boldt COLDWELL BANKER RESIDENTIAL RE

81 Oakdale St, Windermere, FL 34786
/50
$2,500,000
- 6 Beds
- 7.5 Baths
- 8,137 Sq Ft
1724 Windermeredown Place, Windermere, FL 34786

Nestled in Windermere's exclusive lakefront community, this over-acre estate offers private access to the Butler Chain of Lakes. Recognized by K+BB Magazine as Bathroom of the Year, the spa-inspired primary suite features dual rain showers, a freestanding stone tub, sauna, and outdoor shower. The resort-style pool and grotto—crafted by Disney's Animal Kingdom designer—feature a waterfall, slide,

Chad Going Serhant

1724 Windermeredown Place, Windermere, FL 34786
/39
$564,900
- 4 Beds
- 2.5 Baths
- 2,286 Sq Ft
1333 Cornerstone Ct, Orlando, FL 32835

**Limited-time seller incentive — $10,000 credit toward buyer’s rate buydown or closing costs on offers accepted by November 30, 2025.** Nestled in the desirable Ridgemoore community of Orlando, this beautifully updated 4-bedroom, 2-bath pool home offers a perfect balance of comfort, style, and everyday livability. Freshly painted inside and out, the home welcomes you with high ceilings, abundant

Mark D'Italia PROPERTY LOGIC RE

1333 Cornerstone Ct, Orlando, FL 32835
/39
$455,000
- 4 Beds
- 2 Baths
- 2,039 Sq Ft
6127 Froggatt St, Orlando, FL 32835

One or more photo(s) has been virtually staged. Welcome to this charming 4 Bed/ 2 Bath single family home located in Stone Bridge Lakes, a gated community in the heart of Orlando’s desirable MetroWest area. This well-maintained residence offers a bright and spacious layout with comfortable living spaces perfect for both relaxing and entertaining. The home features a welcoming main living area, a

Guanhua Zhang KN PREMIER REALTY, INC

6127 Froggatt St, Orlando, FL 32835
/78
$589,000
- 4 Beds
- 2.5 Baths
- 2,128 Sq Ft
1805 Westpointe Cir, Orlando, FL 32835

Welcome to 1805 West Point Circle, a stunningly upgraded single-family home nestled in the desirable Metro West neighborhood of Orlando, FL. Over $150,000 in recent renovations have transformed this home into a true move-in-ready masterpiece.Boasting 2,128 square feet of thoughtfully renovated living space, this home features four spacious bedrooms and 2.5 bathrooms, providing ample room

Johnny Schafer, Jr KELLER WILLIAMS REALTY AT THE LAKES

1805 Westpointe Cir, Orlando, FL 32835
/27
$849,999
- 4 Beds
- 2.5 Baths
- 2,269 Sq Ft
9237 Mcdavid Ct, Windermere, FL 34786

Come see a truly exceptional single-family residence nestled in the highly regarded Roberts Landing enclave of Windermere. With 4 bedrooms and 21⁄2 bathrooms, this home offers all the space needed to comfortably fit a family looking to stretch out. Located on over an acre of land, this home sits on an elevated lot providing beautiful views of the neighborhood, and a glimpse of Lake Olivia from

David Ruizcalderon GENESYS REALTY LLC

9237 Mcdavid Ct, Windermere, FL 34786
/88
$1,225,000
- 4 Beds
- 3.5 Baths
- 3,585 Sq Ft
4866 Keeneland Cir, Orlando, FL 32819

Welcome to Kensington Park, a gated, luxurious community with approximately 138 households, nestled in the distinguished Dr. Phillips area on the west side of Orlando. Dr. Phillips is known for its upscale neighborhoods, cultural venues, community amenities, and proximity to world-renowned theme parks, restaurant and shopping. Whether you're seeking entertainment, healthcare, education, or

RAVINDRANATH PERSAD PROPERTY OUTLET INTERNATIONAL

4866 Keeneland Cir, Orlando, FL 32819
/42
$895,000
- 4 Beds
- 3 Baths
- 2,410 Sq Ft
299 W 4th Ave, Mount Dora, FL 32757

This traditional farmhouse blends Old Florida charm with everyday comfort — a rare opportunity in the heart of Windermere. Full of character inside and out, the home sits on an elevated corner lot, offering room to play and beautiful curb appeal. A welcoming front porch invites you to slow down, relax, and enjoy the neighborhood setting.Step inside to original wood floors that extend

Judy Black UPSIDE REAL ESTATE INC

299 W 4th Ave, Mount Dora, FL 32757
/44
$1,210,000
- 4 Beds
- 3.5 Baths
- 3,808 Sq Ft
8719 Summerville Place, Orlando, FL 32819

An extraordinary opportunity to live and enjoy in the established Torey Pines community in Dr. Phillips / Bay Hill area. Beautiful 4 Bedroom/ 3.5 Bath Executive Custom home! This magnificent home was built in 1994 by Akers Custom Homes with 3808 square feet of living area. The beautiful remodeled kitchen features superior appliances, a large Breakfast Bar / Pass through and expansive custom

Rick Price KARICK PRICE & ASSOCIATES

8719 Summerville Place, Orlando, FL 32819
/32
$1,998,000
- 5 Beds
- 4.5 Baths
- 4,716 Sq Ft
2958 Marquesas Ct, Windermere, FL 34786

This beautiful and elegant courtyard-style estate, complete with a PRIVATE GUEST HOUSE/IN-LAW SUITE, offers the ideal retreat for multi-generational living within one of the most exclusive gated communities in the Town of Windermere. Designed for comfort, refinement, and privacy, this home embodies Florida luxury living at its finest, where indoor grace meets outdoor serenity. The split floor

Dianna Desboyaux EXP REALTY LLC

2958 Marquesas Ct, Windermere, FL 34786
/71
$960,000
- 4 Beds
- 3.5 Baths
- 3,563 Sq Ft
4973 Keeneland Cir, Orlando, FL 32819

One or more photo(s) has been virtually staged. One of the best indicators of a truly special neighborhood is how rarely homes come on the market—and Kensington Park is a perfect example. This is your opportunity! Welcome to this beautifully designed custom-built Reiche-Silliman pool home. Nestled within an exclusive gated community, this residence offers the perfect balance of privacy, and

Barbara Mills COLDWELL BANKER REALTY

4973 Keeneland Cir, Orlando, FL 32819
/40
$1,025,000
- 6 Beds
- 4 Baths
- 3,645 Sq Ft
Unlisted Address

Your Dream Home Awaits in Dr. Phillips!Stunning 6-Bedroom Corner-Lot Home — Minutes from Disney, Universal & Restaurant Row!Step into luxury living in one of Orlando’s most sought-after neighborhoods. This 6-bedroom, 4-bathroom masterpiece offers the perfect blend of elegance, comfort, and convenience—just moments from world-class dining, entertainment, and attractions.Why You’ll Love

Lisa Camacho Szeto KELLER WILLIAMS CLASSIC

Unlisted Address
/67
$975,000
- 4 Beds
- 4 Baths
- 2,636 Sq Ft
3328 Wax Berry Ct, Windermere, FL 34786

One or more photo(s) has been virtually staged. A rare find in the heart of Downtown Windermere! This 4 bedroom, 4 full bath home with an inground pool sits not only on 1 acre but also in a semi-private cul-de-sac with only 8 other homes. You are welcomed by the circular driveway plus rear side entry garage and additional parking pad perfect for an RV or boat. Interior features include an

Ferris Kassar PREFERRED REAL ESTATE BROKERS

3328 Wax Berry Ct, Windermere, FL 34786
/52
$829,900
- 4 Beds
- 3 Baths
- 3,245 Sq Ft
84 Braelock Dr, Ocoee, FL 34761

Set behind a gated entrance on a prime waterfront lot, this elegant 4-bedroom, 3-bath, 3,245 sq ft residence is set in one of Ocoee’s most desirable enclaves bordering Windermere. A beautiful entry foyer with tall ceilings sets the tone, leading into a dedicated dining room accented with crown molding and custom drapery. Beyond, the formal living room showcases crystal-clear views of the lanai,

Ahmad Hassan COMPASS FLORIDA LLC

84 Braelock Dr, Ocoee, FL 34761
/56
$915,000
- 5 Beds
- 4 Baths
- 3,610 Sq Ft
9106 Panzani Place, Windermere, FL 34786

Discover this beautiful 5-bedroom, 4-bathroom residence nestled inside the exclusive gated community of Tuscany Ridge. Situated on a spacious corner lot, this home showcases exceptional curb appeal with its tile roof, freshly painted exterior, and an impressive three-car garage with an oversized paver driveway. Step inside and fall in love with the thoughtfully designed split floor plan,

Caitlin Dos Santos EXP REALTY LLC

9106 Panzani Place, Windermere, FL 34786
/38
$917,000
- 5 Beds
- 4.5 Baths
- 3,419 Sq Ft
3609 Bellington Dr, Orlando, FL 32835

Luxuriously Updated Pool Home in the Heart of Dr. Phillips – Walk to Windy Ridge Elementary!Welcome to this beautifully updated and spacious home located in the highly sought-after Cypress Landing community in Dr. Phillips. Just minutes from top-rated schools, world-class dining, shopping, and Orlando’s premier attractions, this stunning residence combines luxury, comfort, and convenience in

Rodrigo Cerveira, LLC UNITED REALTY GROUP INC

3609 Bellington Dr, Orlando, FL 32835
/20
$1,050,000
- 4 Beds
- 2.5 Baths
- 3,265 Sq Ft
4627 Woodlot Ct, Orlando, FL 32835

Nestled in the heart of WOODLANDS WINDERMERE - Orange County, this exquisite estate offers about 4,535 SqFt (total) of living space on a lush, mature lot in a prestigious community. With 4 bedrooms and 21⁄2 bathrooms, it’s perfect for multi-generational living or for those who love space and entertaining. A long, paved driveway leads to a extra 3-car plus 2 car garage, with additional parking

Christian Posegger PREMIUM REALTY GROUP USA

4627 Woodlot Ct, Orlando, FL 32835
/48
$1,595,000
- 4 Beds
- 4.5 Baths
- 4,074 Sq Ft
7625 Blue Quail Ln, Orlando, FL 32835

Discover modern elegance in this stunning 4,074 sq ft Monte Carlo model located in the gated Havencrest community. Built in 2020, this 4-bedroom, 4.5-bath home offers a seamless blend of sophistication and comfort. Step through the charming courtyard into an open-concept living space featuring high ceilings, a gourmet kitchen with premium appliances, and a spacious great room perfect for

Jay Stewart SOUTHERN REALTY GROUP LLC

7625 Blue Quail Ln, Orlando, FL 32835
/82
$1,990,000
- 6 Beds
- 6 Baths
- 5,226 Sq Ft
10199 Brocksport Cir, Gotha, FL 34734

Welcome to this extraordinary estate, gracefully positioned on one of the most desired lots within the community, offering unmatched privacy and exclusivity. Strategically located with no neighbors on the right side and a serene green area that will never be developed, this residence provides a rare blend of tranquility, seclusion and prestige. In an exclusive gated enclave of just 34

Carolina Mariano Da Silva PREMIER SOTHEBYS INT'L REALTY

10199 Brocksport Cir, Gotha, FL 34734
/37
$908,000
- 5 Beds
- 4 Baths
- 3,248 Sq Ft
5110 Pine Top Place, Orlando, FL 32819

One or more photo(s) has been virtually staged. On a peaceful cul-de-sac in the beautiful community of Torey Pines, this five-bedroom, four-bath pool home offers endless possibilities across over 3,200 sq ft—all just minutes from Arnold Palmer's Bay Hill Golf Course, Universal Orlando, Restaurant Row, and many of Orlando’s top attractions. Set on a half-acre lot, this property features a spacious

Storm Miller COMPASS FLORIDA LLC

5110 Pine Top Place, Orlando, FL 32819
/79
$834,900
- 4 Beds
- 3 Baths
- 2,642 Sq Ft
2217 Dunhurst Ln, Orlando, FL 32835

Welcome to this stunning one-story estate home in the highly desirable community of Courtleigh Park. Nestled on a peaceful cul-de-sac, this 4-bedroom, 3-bath residence with a 3-car side-entry garage offers the perfect blend of elegance, comfort, and modern upgrades. Set on over half an acre (.56 acres), the property features a screened-in pool with bar and entertaining area, complemented by

Lindsey Mims VOS REAL ESTATE LLC

2217 Dunhurst Ln, Orlando, FL 32835
/40
$1,125,000
- 5 Beds
- 4 Baths
- 3,450 Sq Ft
4719 Kensington Park Blvd, Orlando, FL 32819

Elegant five-bedroom four-bath pool home in gated Kensington Park, Dr. Phillips. Discover timeless sophistication in this beautifully updated residence spanning nearly 3,500 square feet in the highly sought-after, gated Kensington Park community of Dr. Phillips, Orlando. From the moment you step inside this gently lived in and lovingly maintained home, you are greeted with the soaring 14-foot

April Winters PREMIER SOTHEBYS INT'L REALTY

4719 Kensington Park Blvd, Orlando, FL 32819
/48
$905,000
- 5 Beds
- 4 Baths
- 3,640 Sq Ft
9335 Westover Club Cir, Windermere, FL 34786

Welcome to Westover Club, one of Windermere’s most desirable gated communities where tree-lined streets and a perfect location set the stage for your dream home!This beautifully maintained 5-bedroom, 4-bath home sits on an expansive one-third acre lot and offers the perfect blend of comfort, style, and functionality. Step inside to an inviting foyer that opens to a formal dining room and

Jason Neves MARK SPAIN REAL ESTATE

9335 Westover Club Cir, Windermere, FL 34786
/47
$1,137,000
- 5 Beds
- 4 Baths
- 3,343 Sq Ft
4848 Keeneland Cir, Orlando, FL 32819

One or more photo(s) has been virtually staged. Step into a world where elegance meets modern style and convenience in this extensively renovated custom Reiche Silliman home. The real plus is that the renovation has already been done so you do not have to do the work or suffer through the inconvenience, mess, and expense of the process of making this home shine! All this and the home is perfectly

Tim & Reenie Fru The Frush Team COLDWELL BANKER REALTY

4848 Keeneland Cir, Orlando, FL 32819
/51
$899,900
- 4 Beds
- 3 Baths
- 3,189 Sq Ft
5329 Foxshire Ct, Orlando, FL 32819

Tucked at the end of a quiet cul-de-sac in the sought-after Turnbury Woods community of Dr. Phillips, this four-bedroom, three-bath home combines timeless curb appeal with modern updates on nearly an acre of fenced property. A concrete driveway and covered front porch with a swing create a classic first impression, while mature oaks and manicured landscaping frame the home in natural privacy.

Eve Metlis WATSON REALTY CORP

5329 Foxshire Ct, Orlando, FL 32819
/51
$1,080,000
- 4 Beds
- 4 Baths
- 4,676 Sq Ft
2107 Westover Reserve Blvd, Windermere, FL 34786

Discover this beautifully updated 4-bedroom, 4-bathroom home tucked inside the exclusive gated community of Westover Reserve in Windermere, renowned for its tree-lined streets and serene setting. This home seamlessly blends spacious living with exceptional craftsmanship and thoughtful design throughout.Upon entering, you’re welcomed by a bright, open floor plan that showcases a recently

Ken Pozek REAL BROKER, LLC

2107 Westover Reserve Blvd, Windermere, FL 34786
/92
$840,000
- 4 Beds
- 2 Baths
- 2,713 Sq Ft
7905 Chad Ct, Orlando, FL 32835

SELLER WANTS IT SOLD...THIER LOSS IS YOUR GAIN...$60,000 BELOW THE APPRAISED VALUE***PROPERTY APPRAISED AT $900,000.00***WOW!!! Is this the same home?? Look at the BEFORE & AFTER PHOTOS...REMODELING COST = $278K+...WELCOME TO YOUR PRIAVATE PARADISE! Over 1/3 of AN ACARE lot & only $33.00 HOA monthly fee...A gorgeous, luxurious, LIKE BRAND NEW home in desirable Dr. Phillips Location. The Town of

Mahnaz Rabbanifard PREFERRED REAL ESTATE BROKERS

7905 Chad Ct, Orlando, FL 32835
/52
$1,175,000
- 5 Beds
- 3.5 Baths
- 3,615 Sq Ft
5224 Vistamere Ct, Orlando, FL 32819

WOW! A Custom Home That Truly Impresses – In the Heart of Dr. Phillips Step into style and comfort in this stunning 5-bedroom, 3.5-bathroom custom home, tucked away in the quiet and exclusive Vistamere community. With the interior painted and tile flooring throughout the entire home, this property offers a fresh, modern feel with timeless details. From the curb, you'll notice the tile roof,

Farid Premjee REALTY HUB

5224 Vistamere Ct, Orlando, FL 32819
/23
$475,955
- 3 Beds
- 2 Baths
- 1,797 Sq Ft
8611 Sugar Palm Ct, Orlando, FL 32835

Welcome to this beautifully maintained 3-bedroom, 2-bath home with a dedicated office and an air-conditioned enclosed patio, perfectly situated on a premium corner lot in a quiet cul-de-sac in the desirable Palm Cove Estates community of Orlando. This inviting residence offers a bright and functional split floor plan featuring a spacious living room with vaulted ceilings and a cozy wood-burning

Helana Renfroe RED DOOR INVESTMENT GRP LLC

8611 Sugar Palm Ct, Orlando, FL 32835
/34
$535,000
- 3 Beds
- 2 Baths
- 1,492 Sq Ft
4818 Breezy Palms Ct, Windermere, FL 34786

MOVE IN FOR THE HOLIDAYS! Don’t miss this Silver Woods jewel box in a super central location! Large corner lot on quiet cul-de-sac. Featuring a FANTASTIC 55x10 screened porch with custom summer kitchen - PERFECT for relaxing and entertaining. Sunny and bright great room plan with vaulted ceilings and hardwood floors is freshly painted and ready for your personal touches. Updated kitchen with

Lisa Gould KELLER WILLIAMS WINTER PARK

4818 Breezy Palms Ct, Windermere, FL 34786
/67
$3,250,000
- 3 Beds
- 3.5 Baths
- 4,089 Sq Ft
4711 Joanna Garden Ct, Windermere, FL 34786

Nestled within the exclusive Gardens of Isleworth enclave within Isleworth Golf & Country Club, this exquisite residence exemplifies refined Florida living. Crafted by Pellegrini Homes with professionally designed interiors, the single-story home seamlessly blends architectural sophistication with inviting comfort. A brick paver motor court introduces the residence, where a gracious custom arched

Michelle Corbin ISLEWORTH REALTY LLC

4711 Joanna Garden Ct, Windermere, FL 34786
/36
$819,000
- 3 Beds
- 2.5 Baths
- 2,769 Sq Ft
2113 Stillington St, Orlando, FL 32835

Discover this beautifully updated home in the gated community of Westminster Landing. This stunning 3 BD 2.5 BA home with Bonus room offers a spacious open floorplan and a true backyard oasis. Enjoy a lagoon style pool with 3 water features, outdoor kitchen and lush landscaping on a large fenced lot with no rear neighbors. Inside, you’ll find thoughtful updates throughout, including Quartz

Karen Harden LAKESIDE REALTY WINDERMERE INC

2113 Stillington St, Orlando, FL 32835

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