Windermere, FL Homes

• 

  

  

  /15

  $315,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,455 Sq Ft

  11434 Jasper Kay Terrace Unit 306, Windermere, FL 34786

  Under contract-accepting backup offers. Beautiful Lakeside at Lakes of Windermere condominium - Third floor corner unit with screened balcony. This unit features an open floor plan that combines kitchen, living room, and dining room. The kitchen feature 42 inch wood cabinets and a breakfast bar. Spacious primary bedroom. The A/C was replaced in October 2020. Tons of storage throughout the unit!

  

  Jay Stewart

  SOUTHERN REALTY GROUP LLC

  (689) 314-5683

  11434 Jasper Kay Terrace Unit 306, Windermere, FL 34786
• 

  Explore Windermere

• 

  

  

  /23

  $2,300 per month

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • Condo for Rent

  8179 Maritime Flag St Unit 210, Windermere, FL 34786

  3 bedroom, 2 bath condo on second floor. Carpet in living areas. Large pantry in kitchen and second storage closet. Easy access to major road and minutes to Disney. Community offers many amenities. Open floor plan. W/D in unit.

  

  Licinio Cruz

  L & L REALTY GROUP

  (407) 901-9373

  8179 Maritime Flag St Unit 210, Windermere, FL 34786
• 

  

  /2

  $750,000 Sold Sep 18, 2025

  • 3,094 Sq Ft
  • $242/SF
  • 44 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2015

  14654 Yellow Butterfly Rd, Windermere, FL 34786

  A RARE GEM in Summerport Horizon West! Nestled onto a corner lot with extra space, this lovely home charms with tropical palm trees to welcome you at the covered front porch. Upon entry you're greeted with a stunning open floor plan and soaring ceilings, for a palatial feel. Many windows let in plenty of natural light, and plantation shutters have been installed throughout the home. Not only is

  Elijah Lewis FLORIDA IN MOTION REALTY INC

  14654 Yellow Butterfly Rd, Windermere, FL 34786
• 

  

  /2

  Est $438,555 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,692 Sq Ft

  8972 Matriarca Alley, Windermere, FL 34786

  8972 Matriarca Alley, Windermere, FL 34786
• 

  

  

  /80

  $1,499,900

  • 5 Beds
  • 4.5 Baths
  • 4,477 Sq Ft

  1450 Belfiore Way, Windermere, FL 34786

  Welcome to Refined Living in Tuscany RidgeStep into luxury with this fully renovated, move-in-ready home, perfectly situated in the exclusive, gated community of Tuscany Ridge. Every detail of this exquisite residence has been thoughtfully updated to offer modern elegance, comfort, and timeless sophistication.The main level features a spacious primary suite designed to evoke a

  

  Laura Teixeira

  NOBSKA REAL ESTATE LLC

  (689) 308-3110

  1450 Belfiore Way, Windermere, FL 34786
• 

  

  /49

  $7,500 per month

  • 4 Beds
  • 3 Baths
  • 3,000 Sq Ft
  • House for Rent

  5800 Marleon Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Experience luxury Florida living at its finest in this stunning one-story custom home, perfectly situated on nearly an acre in the sought-after Lake Cypress Cove community of Windermere. With approximately 3,000 square feet of beautifully designed living space, this 4-bedroom, 3-bathroom split floor plan offers both privacy and an open, inviting

  

  Eric Bress, Jr

  ERIC BRESS REAL ESTATE LLC

  (407) 871-6125

  5800 Marleon Dr, Windermere, FL 34786
• 

  /2

  $520,000 Sold Sep 17, 2025

  • 2,151 Sq Ft
  • $242/SF
  • 17 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2005

  12915 Cragside Ln, Windermere, FL 34786

  This beautiful 3 bedroom, 2 bath home is nestled in the highly desirable Lakes of Windermere community, offering resort-style amenities. Enter the home to a split-bedroom floor plan with a formal living and dining space at the entryway, a family room following the kitchen, and a bonus room perfect for an office, play room, or home gym. The kitchen is equipped with ample cabinet space, granite

  Nicole Shweky THE REALTY MEDICS

  12915 Cragside Ln, Windermere, FL 34786
• 

  /2

  Est $749,341 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,935 Sq Ft

  12995 Westside Village Loop, Windermere, FL 34786

  12995 Westside Village Loop, Windermere, FL 34786
• 

  

  /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
• 

  

  /55

  $15,000 per month

  • 5 Beds
  • 6.5 Baths
  • 5,104 Sq Ft
  • House for Rent

  4302 Isabella Cir, Windermere, FL 34786

  Welcome to Casabella at Windermere, a private gated community where Spanish-inspired architecture meets modern luxury. This solar-powered estate offers 5 bedrooms, 6.5 bathrooms, and nearly an acre of beautifully landscaped grounds. Designed for a turnkey lifestyle, the home features hardwood floors, soaring ceilings, and high-quality finishes throughout. The gourmet kitchen includes KitchenAid

  

  Bruce Kalin

  JC FLORIDA REALTY LLC

  (407) 783-8539

  4302 Isabella Cir, Windermere, FL 34786
• 

  /2

  $1,260,000 Sold Sep 17, 2025

  • 3,518 Sq Ft
  • $358/SF
  • 1 Day On Market

  • 5 Beds
  • 4 Baths
  • Built 2005

  11709 Camden Park Dr, Windermere, FL 34786

  This beautiful Keene's Pointe pool home, nestled in the charming Village of Camden, offers a light and bright interior with stunning white oak hardwood flooring and high ceilings that contribute to a spacious feel. The kitchen features updated stainless steel appliances including a refrigerator, double oven, microwave, and dishwasher, making it a chef's delight. Enjoy the comfort of newly

  Lisa Schlender CORCORAN PREMIER REALTY

  11709 Camden Park Dr, Windermere, FL 34786
• 

  

  /87

  Est $775,170 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,512 Sq Ft

  4313 Blue Major Dr, Windermere, FL 34786

  4313 Blue Major Dr, Windermere, FL 34786
• 

  

  /46

  $1,200,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,618 Sq Ft

  3629 Lake Buynak Rd, Windermere, FL 34786

  Under contract-accepting backup offers. Welcome to 3629 Lake Buynak Drive—an exceptional opportunity for investors, a custom home build or buyers seeking multigenerational living with flexibility and future upside. Situated in a desired area and on an oversized 1.3 acre lot in the Lake Buynak Estate community located off Lake Butler, this 4-bedroom, 3.5-bath home delivers the prestige of a

  

  Tania Matthews

  KELLER WILLIAMS ELITE PARTNERS III REALTY

  (407) 519-3922

  3629 Lake Buynak Rd, Windermere, FL 34786
• 

  

  /46

  $1,601 - $2,425 per month

  Talcott at Windermere

  1 - 3 Beds

  5820 Nature View Dr, Windermere, FL 34786

  With thoughtful design and exclusive amenities, Talcott at Windermere, is your premier destination for luxury living in Windermere, Florida! Our luxury one, two, and three-bedroom apartments, ranging up to 1,380 square feet, redefine luxury with a range of modern interior features. Step into a home with soaring 9 foot ceilings, a stylish two-tone paint scheme, wood-style flooring, and AirPlay

  5820 Nature View Dr, Windermere, FL 34786
• 

  /2

  $1,330,000 Sold Sep 15, 2025

  • 3,972 Sq Ft
  • $335/SF
  • 25 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2016

  17551 Black Rail St, Windermere, FL 34786

  Welcome to a home where timeless elegance is perfectly paired with thoughtful upgrades and luxurious touches. Located in the highly sought-after Enclave community, this beautifully updated 5-bedroom, 4-bathroom residence offers space, sophistication, and exceptional functionality.Step inside to discover nearly every room adorned with a unique chandelier, adding character and charm

  John Cunningham KELLER WILLIAMS CLASSIC

  17551 Black Rail St, Windermere, FL 34786
• 

  

  /52

  Est $2,867,160 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 6,227 Sq Ft

  1336 Lake Olivia Ln, Windermere, FL 34786

  1336 Lake Olivia Ln, Windermere, FL 34786
• 

  

  /40

  $546,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 2,009 Sq Ft

  8160 Iron Mountain Trail, Windermere, FL 34786

  Nestled in the highly desirable Windermere Trails community, this beautiful home offers an unparalleled blend of modern design, high end finishes and everyday functionality. The 3 bedrooms, 2 1/2 baths home's open-concept design seamlessly integrates the living and dining areas with the spacious kitchen and family room, creating an inviting space for everyday living and entertaining.

  

  Francine Arroyo Santowski

  BHHS FLORIDA REALTY

  (407) 955-9391

  8160 Iron Mountain Trail, Windermere, FL 34786
• 

  

  /19

  $2,650 per month

  • 3 Beds
  • 2.5 Baths
  • 1,884 Sq Ft
  • Townhouse for Rent

  11213 Grander Dr, Windermere, FL 34786

  Charming Townhome for Rent in Windermere!Spacious 3-bedroom + den, 2.5-bath home in the sought-after Lake Burden community. The open floor plan connects the bright living and dining areas to a stylish kitchen with solid wood cabinets, granite countertops, and plenty of storage. French doors open to a private courtyard-perfect for relaxing or entertaining-with direct access to a two-car

  Tatiana Mayer THE FLORIDA LOUNGE REALTY LLC

  11213 Grander Dr, Windermere, FL 34786
• 

  /2

  $385,000 Sold Sep 15, 2025

  • 1,644 Sq Ft
  • $234/SF
  • 56 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2008

  7715 Anselmo Ln, Windermere, FL 34786

  $5000 CREDIT at closing towards whatever you want-closing cost, rate buydown, lower price, new carpet, it's your choice!! Welcome home to this beautifully maintained 3-bedroom, 2.5-bath townhouse in the highly desirable Berkshire Park area of Windermere! This spacious home features a freshly painted interior, a generous walk-in pantry, and a private courtyard perfect for grilling, entertaining,

  Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

  7715 Anselmo Ln, Windermere, FL 34786
• 

  

  /30

  Est $870,311 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,690 Sq Ft

  8460 Elba Isle Ct, Windermere, FL 34786

  8460 Elba Isle Ct, Windermere, FL 34786
• 

  

  /100

  $2,650,000 Pending

  • 5 Beds
  • 8 Baths
  • 7,621 Sq Ft

  9905 Lanai View Ct, Windermere, FL 34786

  Under contract-accepting backup offers. Welcome to a home that isn’t just designed—it’s curated.Tucked behind the gates of one of Central Florida’s most exclusive golf communities, 9905 Lanai View Court is the kind of estate that makes you pause. Nearly 7,000 square feet of single-level, custom-crafted living plus more than 800 square feet private media room on the second floor. Every

  

  Bent Danholm

  MAXIM REALTY ORLANDO

  (407) 512-8409

  9905 Lanai View Ct, Windermere, FL 34786
• 

  

  /51

  $1,554 - $2,570 per month

  Citra at Windermere

  1 - 3 Beds

  11353 Citra Cir, Windermere, FL 34786

  Experience the finest apartments in Windermere, Florida at The Citra at Windermere. Our apartment community offers a variety of distinctive one, two, and three bedroom apartment homes. Conveniently located, Citra at Windermere is walking distance to shopping, restaurants and entertainment. In addition, we are located within some of the top rated schools in Orange county, including Bay Lake

  11353 Citra Cir, Windermere, FL 34786
• 

  /2

  $2,075,000 Sold Sep 15, 2025

  • 4,197 Sq Ft
  • $494/SF
  • 142 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1980

  1404 Kelso Blvd, Windermere, FL 34786

  BRAND NEW ROOF 2025! LAKEFRONT! Prepare to be amazed by this exquisitely renovated estate home with a BRAND NEW HEATED Infinity Pool, perfectly nestled on the tranquil shores of Lake Cypress near downtown Windermere. Set on 1.2 acres with 100 ft of lake frontage, this luxurious residence boasts an attached guest house and an array of high-end features. Live each day watching sunsets and seeing

  Corinne Defilippis EXP REALTY LLC

  1404 Kelso Blvd, Windermere, FL 34786
• 

  /2

  Est $1,446,869 Not Listed For Sale

  • 6 Beds
  • 6.5 Baths
  • 4,634 Sq Ft

  7431 Lake Albert Dr, Windermere, FL 34786

  7431 Lake Albert Dr, Windermere, FL 34786
• 

  

  /35

  $675,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 2,991 Sq Ft

  7401 Ella Ln, Windermere, FL 34786

  Spectacular Windermere Home WITH LUXURIOUS IN-LAW SUITE! Experience the perfect blend of elegance, comfort, and versatility in this stunning 5-bedroom, 4.5-bathroom home in the prestigious Windermere community. Boasting a fully-equipped mother-in-law or older kid suite above the garage, this separate studio apartment offers privacy, abundant space, and its own entrance—ideal for guests, extended

  

  Kriselys Tapia

  SERHANT

  (407) 934-0478

  7401 Ella Ln, Windermere, FL 34786
• 

  

  /24

  $2,750 per month

  • 3 Beds
  • 2 Baths
  • 1,723 Sq Ft
  • House for Rent

  9360 Woodbreeze Blvd, Windermere, FL 34786

  Beautifully renovated home available for rent in the Highly Desirable Silver Woods Neighborhood in Windermere. This 3 bedroom 2 bathroom home features new wood-plank tile flooring throughout the living areas. Open Living area with a split floor plan. Master bedroom is secluded on the left side of the home with the guest rooms on the other wing. Kitchen with all stainless appliances. Washer and

  Silvia Odebrecht ICON REALTY ASSOCIATES INC

  9360 Woodbreeze Blvd, Windermere, FL 34786
• 

  /2

  $372,000 Sold Sep 12, 2025

  • 1,461 Sq Ft
  • $255/SF
  • 16 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2005

  5318 Kumquat Loop, Windermere, FL 34786

  This beautifully updated three-bedroom townhome in Windermere offers the perfect blend of comfort, convenience, and location, with the primary suite thoughtfully located on the first floor. Situated in the desirable Summerport community, this home enjoys a picturesque setting just steps from a tranquil stocked pond and fishing pier right outside your front door. Inside, the open layout creates an

  Ronald Ziolkowski RE/MAX PRIME PROPERTIES

  5318 Kumquat Loop, Windermere, FL 34786
• 

  

  /37

  Est $1,598,391 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,396 Sq Ft

  1214 Estancia Woods Loop, Windermere, FL 34786

  1214 Estancia Woods Loop, Windermere, FL 34786
• 

  

  /54

  $1,795,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 3,670 Sq Ft

  830 Oakdale St, Windermere, FL 34786

  Under contract-accepting backup offers. RARE FIND IN DOWNTOWN WINDERMERE!! This immaculate home defines where luxury meets contemporary, nestled in the heart of downtown Windermere. Pull up into your drive of Italian laced pavers and enter into your new home through custom French doors. You will be met by 2 story open floor plan where the oversized family room overlooks an outdoor oasis. A

  

  Jay Martin

  CORCORAN PREMIER REALTY

  (407) 904-4148

  830 Oakdale St, Windermere, FL 34786
• 

  

  /91

  $1,740 - $3,950 per month

  Addison At Windermere

  1 - 3 Beds

  13644 Tortona Ln, Windermere, FL 34786

  Addison At Windermere is located at 13644 Tortona Lane Windermere, FL and is managed by GrayCo Properties, LLC, a reputable property management company. Addison At Windermere offers 1 to 3 bedroom apartments ranging in size from 592 to 1508 sq.ft. Amenities include Microwave and more. This rental community is pet friendly, welcoming both cats and dogs. Property is located in the 34786 ZIP code.

  13644 Tortona Ln, Windermere, FL 34786
• 

  /2

  $1,750,000 Sold Sep 12, 2025

  • 5,844 Sq Ft
  • $299/SF
  • 149 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2004

  12860 Jacob Grace Ct, Windermere, FL 34786

  WOW.. what an opportunity!! Presenting an exceptional 5-bedroom, 4.5-bathroom estate located in the prestigious 24-hour guard-gated community of Tilden’s Grove in Windermere, Florida. The residence seamlessly blends timeless Mediterranean charm with modern upgrades and resort-style living. Step inside to discover exquisite cabinetry throughout, enhancing the home’s refined aesthetic. The chef’s

  Matt Tomaszewski CORCORAN PREMIER REALTY

  12860 Jacob Grace Ct, Windermere, FL 34786
• 

  

  /62

  Est $2,432,737 Not Listed For Sale

  • 5 Beds
  • 7 Baths
  • 5,734 Sq Ft

  13334 Bellaria Cir, Windermere, FL 34786

  13334 Bellaria Cir, Windermere, FL 34786
• 

  /2

  $2,500,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,348 Sq Ft

  10121 Lone Tree Ln, Orlando, FL 32836

  A rare opportunity awaits with this exceptional triple-lot property on the renowned Butler Chain of Lakes—just minutes from the coveted Dr. Phillips area and with no HOA restrictions. Offering prime lakefront access, this oversized parcel is priced primarily for its land value and is the perfect canvas for creating your dream estate.The current residence is dated but move-in ready, giving

  

  Ursula Garcia Moraes

  PRISTINE INTERNATIONAL REALTY LLC

  (321) 334-2943

  10121 Lone Tree Ln, Orlando, FL 32836
• 

  

  /36

  $2,600 per month

  • 3 Beds
  • 2.5 Baths
  • 1,503 Sq Ft
  • Townhouse for Rent

  13348 Abuela Alley, Windermere, FL 34786

  NO SMOKING AND NO PETS ALLOWED. Welcome to this beautiful home located in the desirable community of Windermere! This well-maintained property will be available for move-in starting October 27th. Offering modern finishes, spacious living areas, and an inviting atmosphere, it’s the perfect place to call home. Conveniently situated just minutes from Walt Disney World, top-rated schools, shopping,

  Andre Chiappetta Dos Santos Cam EPIC REALTY

  13348 Abuela Alley, Windermere, FL 34786
• 

  /2

  $1,475,000 Sold Sep 11, 2025

  • 3,983 Sq Ft
  • $370/SF
  • 81 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 2004

  8475 Eagles Loop Cir Unit 6, Windermere, FL 34786

  Welcome home to an enviable Florida life in one of SW Orlando's most desirable neighborhoods! Opportunity awaits in the highly coveted, guard gated community of Keene's Pointe. Redefine Florida living in this masterfully designed, expansive W J. Sauerwine 5 bedroom, 5 bath plus office pool home, which sits on nearly 1/2 acre with no rear neighbors. Spanning nearly 4,000 square feet of living

  Emily Lewis LAKESIDE REALTY WINDERMERE INC

  8475 Eagles Loop Cir Unit 6, Windermere, FL 34786
• 

  

  /80

  Est $2,514,691 Not Listed For Sale

  • 5 Beds
  • 7 Baths
  • 5,161 Sq Ft

  11628 Waterstone Loop Dr, Windermere, FL 34786

  11628 Waterstone Loop Dr, Windermere, FL 34786
• 

  

  /41

  $435,000

  • 3 Beds
  • 2.5 Baths
  • 1,461 Sq Ft

  13808 Ancilla Blvd, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Beautiful 3-bedroom, 2.5-bath townhome located in the desirable SUMMERPORT community of Windermere. Residents enjoy fantastic amenities, including a CLUBHOUSE, a resort-style community swimming pool, tennis court, Volleyball court, basketball court, and a fitness center, multiple playground park and green spaces to enjoy beauty and nature, plus a

  

  Carlos German

  EXP REALTY LLC

  (407) 329-6677

  13808 Ancilla Blvd, Windermere, FL 34786
• 

  

  /117

  $1,606 - $5,805 per month

  Venetian Isle

  1 - 3 Beds

  6506 San Francesco Way, Windermere, FL 34786

  A beautiful community with luxury one, two and three-bedroom apartment homes with a Mediterranean flair.We invite you to transport yourself to an upgraded level of luxury right at your front door. Every finish is hand-selected with the finest touch to make every day surpass the next. Our elegant, resort-inspired amenities have a level of sophistication youll find awe-inspiring day and night.

  6506 San Francesco Way, Windermere, FL 34786
• 

  /2

  $1,060,000 Sold Sep 11, 2025

  • 2,011 Sq Ft
  • $527/SF
  • 82 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1957

  76 Oakdale St, Windermere, FL 34786

  Now is your chance to live "Among the Lakes"! This canal-front home includes a private boat dock with DIRECT ACCESS to the famous Butler Chain-of-Lakes! This 3BR/1.5BA home sits on an impressive .39 acre lot and is located on one of the very few paved streets in the Town of Windermere. Property features include No HOA, enormous in-ground pool (30 x 16), partially-finished 2nd floor, county water

  Bill Martini BHHS FLORIDA REALTY

  76 Oakdale St, Windermere, FL 34786
• 

  

  /40

  Est $745,126 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,988 Sq Ft

  9150 Outlook Rock Trail, Windermere, FL 34786

  9150 Outlook Rock Trail, Windermere, FL 34786

Showing Results 1 - 40, Page 1 of 18