271

Homes for Rent near Windermere Preparatory School

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  • /35

    $1,683 - $2,913 per month

    MAA Windermere

    1 - 2 Beds

    11598 Lachlan Ln, Windermere, FL 34786

    TOUR YOUR WAY! We have a tour to fit your needs- virtual, self-guided, or agent-guided. Call MAA Windermere home in Windermere, FL. Our one-, two-, and three-bedroom apartment homes have all of the modern conveniences you're looking for. Select apartments feature spacious showers, double vanities, and soaking tubs. All units come with a washer/dryer and lots of natural light. Enjoy an expansive

    11598 Lachlan Ln, Windermere, FL 34786
  • /5

    $2,700 per month

    • 3 Beds
    • 2 Baths
    • 1,784 Sq Ft
    • House for Rent

    9349 Pecky Cypress Way, Orlando, FL 32836

    Welcome to this charming 3-bedroom, 2-bathroom home located in the highly desirable gated community of Cypress Chase!This warm and inviting residence features an open layout with abundant natural light, high ceilings, and a neutral color palette that complements any décor. No carpet throughout the home offers added convenience and easy maintenance. The home is tucked within a quiet, peaceful,

    Micaela Navarra M2M REALTY

    9349 Pecky Cypress Way, Orlando, FL 32836
  • /28

    $1,932 - $2,647 per month

    Overture Hamlin 55+ Active Adult Apartment...

    1 - 2 Beds

    5795 Citrus Village Blvd, Winter Garden, FL 34787

    Schedule your in-person or virtual tour today! Walk-ins are also welcome!

    5795 Citrus Village Blvd, Winter Garden, FL 34787
  • /27

    $4,332 per month

    • 4 Beds
    • 3 Baths
    • 2,738 Sq Ft
    • House for Rent

    2533 Ridgewind Way, Windermere, FL 34786

    4 Bedroom Home For Rent In Windermere3-Car Garage, Pool View, Screened-in Pool, Screened-in Patio, Master Bedrm Downstairs, Huge Master Suite, Huge Family Room, Hardwood Flooring, Tile in Wet Areas, Additional $150 charge for Pool Maintenance. The deposit amount is based upon the application results. Pets: OK - Medium 50lbs (Dangerous Pets are not permitted, Pit Bulls, etc.) Priced $3,999.00

    Jay Myers ORLANDO REALTY & PROPERTY MGNT

    2533 Ridgewind Way, Windermere, FL 34786
  • /35

    $1,645 - $2,571 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
  • /15

    $3,000 per month

    • 4 Beds
    • 2 Baths
    • 2,441 Sq Ft
    • House for Rent

    8609 Sunny Hollow Ln, Orlando, FL 32819

    Be the First to Live in This Newly Renovated Luxury Home in Dr. Phillips -- Available Now! Welcome to this freshly renovated 4 Bedroom, 2 Bath home perfectly situated in the Dr. Phillips community. Offering over 2,400 sq. ft. of modern, high-end living space, this property combines elegance, comfort, and a prime location. Enjoy bright and open living and dining areas, beautiful quartz

    Karishma Scheid FLORIDA REALTY INVESTMENTS

    8609 Sunny Hollow Ln, Orlando, FL 32819
  • /35

    $2,200 per month

    • 3 Beds
    • 2 Baths
    • 1,544 Sq Ft
    • Condo for Rent

    11434 Jasper Kay Terrace Unit 1117, Windermere, FL 34786

    Newly renovated 3 bedroom 2 bath unit on the third floor with elevator and stair access. No directly connected neighbors on all four sides so super quiet and private. Great community with access to a large pool, clubhouse, fitness center, beach volleyball court, tennis courts, playground and walking trails around the lake. Close to boating and fishing in the Butler lakes. Short walk to shops,

    11434 Jasper Kay Terrace Unit 1117, Windermere, FL 34786
  • /19

    $3,000 per month

    • 3 Beds
    • 2 Baths
    • 1,979 Sq Ft
    • House for Rent

    15379 Shonan Gold Dr, Winter Garden, FL 34787

    Welcome to your next home!This stunning 4 Bedroom, 2 Bathroom residence offers 1,979 sq ft of comfortable living in a peaceful and beautifully maintained community.Perfect for families, professio9nals, or anyone looking for a fresh start in the new year.

    Diana Gutierrez Castellanos LPT REALTY, LLC

    15379 Shonan Gold Dr, Winter Garden, FL 34787
  • /35

    $2,500 per month

    • 3 Beds
    • 2 Baths
    • 1,484 Sq Ft
    • House for Rent

    15412 Amberbeam Blvd, Winter Garden, FL 34787

    BEAUTIFUL FAMILT HOME IN STONYBROOK WEST GOLF COMMUNITY!! HOME COMES WITH MOUNTED 65" TV IN LIVING ROOM! Discover luxury living in this captivating 3-bed, 2-bath home nestled alongside a pristine golf course in the secure and family-friendly gated community of Stoneybrook West. Unwind in the spacious interior, adorned with desirable features like a cozy fireplace, ceiling fans,

    15412 Amberbeam Blvd, Winter Garden, FL 34787
  • /37

    $2,600 per month

    • 3 Beds
    • 2.5 Baths
    • 2,297 Sq Ft
    • House for Rent

    8582 Powder Ridge Trail, Windermere, FL 34786

    Modern 3-Bedroom Home for Rent in Prime Windermere Location – Pet Friendly! Welcome to your new lakeside retreat! This beautifully upgraded 3-bedroom, 2.5-bathroom home features an open-concept floor plan that seamlessly connects the kitchen, living, and dining areas—perfect for everyday living and entertaining. The home boasts elegant custom shutters on every window, sleek laminate flooring, and

    Mariana Rondon LPT REALTY, LLC

    8582 Powder Ridge Trail, Windermere, FL 34786
  • /30

    $3,949 per month

    • 5 Beds
    • 4 Baths
    • 3,256 Sq Ft
    • House for Rent

    8931 Lookout Pointe Dr, Windermere, FL 34786

    - $4,100/month for a 1 year lease- $3,999 for an 18 month lease- $3,949 for a 24 month leaseThis 5/4 2 story home with a Bonus room located in Windemere Trails is just over 3200 sq ft. Downstairs is one bedroom and one full bathroom, separate dining and living room, and large eat-in kitchen. The upgraded kitchen has gorgeous granite counters with, lots of counter space, solid

    8931 Lookout Pointe Dr, Windermere, FL 34786
  • /11

    $2,600 per month

    • 3 Beds
    • 2 Baths
    • 1,335 Sq Ft
    • Townhouse for Rent

    7708 Bexton Ln, Windermere, FL 34786

    Beautiful 3 bedroom 2.5 bath townhome located in Windermere! The home features an open kitchen with stainless steel appliances and beautiful 42" cabinets . Just off the dining area step out to the cozy fenced in courtyard. Upstairs there is a large master bedroom with walk in closet. The master bath features dual sinks and tiled walk in shower. There are 2 additional bedrooms on the second floor

    Reynaldo Izaguirre ALTIS REALTY

    7708 Bexton Ln, Windermere, FL 34786
  • /17

    $2,799 per month

    • 4 Beds
    • 2.5 Baths
    • 2,060 Sq Ft
    • House for Rent

    14561 Crested Plume Dr, Winter Garden, FL 34787

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2943.90. That covers your base rent, $2799.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    14561 Crested Plume Dr, Winter Garden, FL 34787
  • /22

    $2,550 per month

    • 3 Beds
    • 2.5 Baths
    • 1,725 Sq Ft
    • Townhouse for Rent

    7231 Shadeview Aly, Windermere, FL 34786

    Beautiful 3 beds, 2.5 baths, 2 car garage townhome at Ashlin Park in the heart of Windermere. Must see all this community has to: Community Pool, Club House, Playground, Conservation areas, ponds, access to bike trail and just at walking distance from Restaurants and market places. Right next to the 535 road, one mile away from Publix and commercial development with many new restaurants. MUST SEE!

    Isabel Sirizzotti SUNNY 365 REALTY GROUP

    7231 Shadeview Aly, Windermere, FL 34786
  • /17

    $2,460 per month

    • 3 Beds
    • 2.5 Baths
    • 1,669 Sq Ft
    • House for Rent

    15261 Harrowgate Way, Winter Garden, FL 34787

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Rent this home by December 31, 2025 and

    15261 Harrowgate Way, Winter Garden, FL 34787
  • /49

    $4,000 per month

    • 3 Beds
    • 3.5 Baths
    • 2,744 Sq Ft
    • House for Rent

    11949 Verrazano Dr, Orlando, FL 32836

    Experience magical evenings from your own backyard—where you can unwind in the private hot tub and enjoy nightly Disney fireworks lighting up the sky. Perfectly situated in one of Orlando’s most desired zip codes. Step inside this beautiful 3-bed, 3.5-bath home offering 2,744 sq.ft. of stylish living, and step outside to your own private resort. The expansive backyard is fully equipped with

    Camila Ricchetti FLORIDA CONNEXION PROPERTIES

    11949 Verrazano Dr, Orlando, FL 32836
  • /16

    $2,225 per month

    • 4 Beds
    • 2 Baths
    • 1,479 Sq Ft
    • House for Rent

    256 Daniels Pointe Dr, Winter Garden, FL 34787

    Special offer: Pay just $500 of your base rent (taxes and fees not included) as your security deposit, valid for new applicants who sign a 12-month lease by December 31, 2025. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This property is professionally managed by AMH, a leading single-family rental company. We work to

    256 Daniels Pointe Dr, Winter Garden, FL 34787
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    $3,400 per month

    • 4 Beds
    • 3 Baths
    • 2,971 Sq Ft
    • House for Rent

    15331 Hayworth Dr, Winter Garden, FL 34787

    Available starting February 1, 2026 for lease, this elegantly updated residence is located within a highly sought after gated community in the heart of Winter Garden, offering nearly 3,000 square feet of refined living space designed for both elevated comfort and functionality. Upon entry, you are welcomed by a grand open layout featuring formal living and dining spaces, complemented by updated

    Nikhil Vashist THE FLORIDA PROPERTY SHOP SALE

    15331 Hayworth Dr, Winter Garden, FL 34787
  • /20

    $2,799 per month

    • 5 Beds
    • 2 Baths
    • 3,290 Sq Ft
    • House for Rent

    321 Black Springs Ln, Winter Garden, FL 34787

    This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 5 bedrooms, 2.5 bathrooms, and approximately 3,290 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your rental

    321 Black Springs Ln, Winter Garden, FL 34787
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    $4,250 per month

    • 4 Beds
    • 3 Baths
    • 2,741 Sq Ft
    • House for Rent

    8125 Courtleigh Dr, Orlando, FL 32835

    Beautiful home. 4-bed, 3-bath custom home. LOTS of light. 1/2-acre lot designed for natural, private beauty. Heated pool/Spa.Great location. Pool and lawn service are included in the rent. Pet-friendly. AVAILABLE NOW. Great opportunity.

    Eliana Camargo FLORIDA CONNEXION PROPERTIES

    8125 Courtleigh Dr, Orlando, FL 32835
  • /20

    $2,860 per month

    • 4 Beds
    • 2 Baths
    • 2,022 Sq Ft
    • House for Rent

    1314 Glenwick Dr, Windermere, FL 34786

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $3004.90. That covers your base rent, $2860.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    1314 Glenwick Dr, Windermere, FL 34786
  • /9

    $3,400 per month

    • 5 Beds
    • 3 Baths
    • 3,180 Sq Ft
    • House for Rent

    1 Roseberry Ct, Ocoee, FL 34761

    Spacious and adaptable home located in a quiet cul-de-sac within a respected school district. This residence includes 5 bedrooms, 3 bathrooms, and a handicap-accessible suite, along with multiple living areas designed to support different living needs.In-Ground Pool • Washer & Dryer • Central Air Conditioning • Quiet Neighborhood Layout Overview First FloorMain bedroom Extra-large,

    Steven Koleno BEYCOME OF FLORIDA LLC

    1 Roseberry Ct, Ocoee, FL 34761
  • /10

    $3,595 per month

    • 4 Beds
    • 3 Baths
    • 3,058 Sq Ft
    • House for Rent

    11530 Vicolo Loop, Windermere, FL 34786

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $3739.90. That covers your base rent, $3595.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    11530 Vicolo Loop, Windermere, FL 34786
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    $3,500 per month

    • 4 Beds
    • 3 Baths
    • 2,072 Sq Ft
    • House for Rent

    5144 Citrus Leaf Blvd, Winter Garden, FL 34787

    Beatuful 4 bedrom 3 bath house located in the Silver Leaf Community. Features a large open floor plan with the kitchen, living room and dining room, Laminate flooring in the common areas and carpet in the bedrooms.

    Sarah Heise TREE REALTY

    5144 Citrus Leaf Blvd, Winter Garden, FL 34787
  • /17

    $2,395 per month

    • 3 Beds
    • 2.5 Baths
    • 1,857 Sq Ft
    • House for Rent

    1647 Portcastle Cir, Winter Garden, FL 34787

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2539.90. That covers your base rent, $2395.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    1647 Portcastle Cir, Winter Garden, FL 34787
  • /68

    $3,500 per month

    • 3 Beds
    • 2.5 Baths
    • 1,980 Sq Ft
    • House for Rent

    6060 Roseate Spoonbill Dr, Windermere, FL 34786

    Welcome to this beautifully maintained 3-bedroom, 2.5-bath home situated on a desirable corner lot in the highly sought-after community of Windermere Landings. Located right off Chase Road, this prime Windermere location offers exceptional walkability—just steps from Sunset Park Elementary, Walgreens, Papa John’s, and other neighborhood conveniences. This is truly an ideal community for families

    Mulcy Tenorio FLORIDA CONNEXION PROPERTIES

    6060 Roseate Spoonbill Dr, Windermere, FL 34786
  • /20

    $2,000 per month

    • 3 Beds
    • 2 Baths
    • 1,212 Sq Ft
    • Condo for Rent

    7757 Sugar Bend Dr, Orlando, FL 32819

    Welcome home to this bright and inviting 3-bedroom, 2-bathroom condo featuring an attached one-car garage. This home offers a comfortable open floor plan with plenty of natural light.? Open living & dining area – perfect for entertaining? Spacious kitchen with ample cabinet space ? Primary suite with private bath and walk-in closet? Two additional bedrooms great for family,

    7757 Sugar Bend Dr, Orlando, FL 32819
  • /31

    $8,995 per month

    • 4 Beds
    • 3.5 Baths
    • 3,751 Sq Ft
    • House for Rent

    6533 Cartmel Ln, Windermere, FL 34786

    Tucked away in the desirable guard-gated community of The Reserve at Lake Butler Sound, this exceptional 4-bedroom, 3.5-bath single-story pool home blends timeless Mediterranean style with modern sophistication. Set on over half an acre in a quiet cul-de-sac, the home welcomes you with a paver driveway, lush mature landscaping, and an elegant entry framed by architectural columns. As you enter

    Andy Neal THE AGENCY ORLANDO

    6533 Cartmel Ln, Windermere, FL 34786
  • /20

    $3,500 per month

    • 3 Beds
    • 3 Baths
    • 2,696 Sq Ft
    • House for Rent

    8014 Winpine Ct, Orlando, FL 32819

    Welcome to your dream home in the heart of Orlando! This stunning 3-bedroom, 3-bathroom house offers a spacious 2,696 square feet of living space, perfect for those who love to entertain or simply enjoy a comfortable lifestyle. With small dogs ( maximum 2 ) allowed, your furry friend will feel right at home too!Step inside to discover a beautifully designed interior featuring:- Modern

    8014 Winpine Ct, Orlando, FL 32819
  • /21

    $5,500 per month

    • 3 Beds
    • 2 Baths
    • 2,056 Sq Ft
    • House for Rent

    8447 Bowden Way, Windermere, FL 34786

    Welcome to Keenes Point - Windermere, a stunning 3-bedroom, 2-bathroom home located in the desirable Windermere, FL. This property is nestled within a secure gated community, offering an added layer of peace and security. The home boasts a private pool, perfect for cooling off during those hot Florida summers. The private backyard provides ample space for outdoor activities or simply enjoying the

    Julien Silva JOHN SILVA REALTY & ASSOCIATES

    8447 Bowden Way, Windermere, FL 34786
  • /20

    $3,495 per month

    • 4 Beds
    • 2.5 Baths
    • 2,718 Sq Ft
    • House for Rent

    7781 Snowberry Cir, Orlando, FL 32819

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $3759.90. That covers your base rent, $3495.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    7781 Snowberry Cir, Orlando, FL 32819
  • /16

    $3,990 per month

    • 3 Beds
    • 2 Baths
    • 1,784 Sq Ft
    • House for Rent

    415 E 6th Ave, Windermere, FL 34786

    Welcome to Windermere Living at Its Finest!Experience comfort, style, and true Florida living in this beautifully updated 3-bedroom, 2-bath home located at 415 E 6th Ave in the heart of Windermere. This inviting residence offers luxury vinyl flooring throughout, stylish tile in the bathrooms, and an open, airy layout designed for both relaxation and entertaining. Step outside to your own

    Irene Fort PREFERRED REAL ESTATE BROKERS

    415 E 6th Ave, Windermere, FL 34786
  • /20

    $2,700 per month

    • 3 Beds
    • 2.5 Baths
    • 1,920 Sq Ft
    • Townhouse for Rent

    11320 Jasper Kay Terrace, Windermere, FL 34786

    Property Id: 2261362$200 OFF FEBRUARY RENT IF YOU MOVE IN BEFORE DECEMBER 15, 2025!!Welcome to this beautiful end-unit townhome in the desirable Lake Burden community of Windermere. Featuring 3 bedrooms plus an office, 2.5 baths, and a 1.5-car garage, this home offers abundant natural light and a clean, modern layout perfect for today's lifestyle.Key Features- End-unit

    11320 Jasper Kay Terrace, Windermere, FL 34786
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    $2,600 per month

    • 3 Beds
    • 2.5 Baths
    • 1,568 Sq Ft
    • Townhouse for Rent

    6314 Hamlin Reserve Blvd, Winter Garden, FL 34787

    Beautiful townhome available for rent in the desirable Hamlin Reserve community. This well-maintained property features 3 bedrooms and 2.5 bathrooms, with tile flooring throughout the first floor. The kitchen offers stainless steel appliances and granite countertops. The primary bathroom includes dual sinks and a walk-in shower. Enjoy a private fenced patio and a 2-car garage. Community amenities

    Vicente Virgilio ALTIS REALTY

    6314 Hamlin Reserve Blvd, Winter Garden, FL 34787
  • /18

    $2,500 per month

    • 3 Beds
    • 2.5 Baths
    • 1,644 Sq Ft
    • Townhouse for Rent

    12974 Vennetta Way, Windermere, FL 34786

    Property Id: 2161517NO Carpet!! Well-maintained 3b/2.5b Townhome in Windermere with brand new luxury vinyl floor! Spacious bedrooms with walk-in closet. Two car garage. Private courtyard. Granite countertop. Quiet and friendly neighborhood features tennis court, community pool and playground. Zoned for great schools. Lawn maintenance is included.

    12974 Vennetta Way, Windermere, FL 34786
  • /7

    $2,440 per month

    • 2 Beds
    • 2.5 Baths
    • 1,200 Sq Ft
    • Townhouse for Rent

    7054 Broomshedge Trail, Winter Garden, FL 34787

    Amazing and very comfortable Townhome with two bedrooms and 2.5 bath, very nice backyard , all appliances includes, excellent community of Independence with many activities including gyms, Pools, etc garage for two cars covered and another 2 uncovered, rents includes High Speed Internet and huge Cable tv, (save like 150$ monthly) , Aprox 2 miles to Walt Disney World, Independence Community with

    Giovanni Montano LA ROSA REALTY KISSIMMEE

    7054 Broomshedge Trail, Winter Garden, FL 34787
  • /19

    $2,245 per month

    • 3 Beds
    • 2.5 Baths
    • 1,358 Sq Ft
    • House for Rent

    1756 Portcastle Cir, Winter Garden, FL 34787

    Special offer: Pay just $500 of your base rent (taxes and fees not included) as your security deposit, valid for new applicants who sign a 12-month lease by December 31, 2025. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This property is professionally managed by AMH, a leading single-family rental company. We work to

    1756 Portcastle Cir, Winter Garden, FL 34787
  • /67

    $5,000 per month

    • 5 Beds
    • 4 Baths
    • 3,207 Sq Ft
    • House for Rent

    5311 Bay Side Dr, Orlando, FL 32819

    Looking for a luxury home in the established community of North Bay, positioned within Arnold Palmer’s esteemed Bay Hill Golf Club nested in the heart of Dr Phillips. The moment you enter your new home you are welcomed by a large open concept floor plan overlooking you screen in pool. The design of the home seamlessly connects all the shared living space ideal for growing families and

    Johnathan Lam NATIONAL REAL ESTATE LLC

    5311 Bay Side Dr, Orlando, FL 32819
  • /20

    $2,549 per month

    • 4 Beds
    • 2 Baths
    • 1,705 Sq Ft
    • House for Rent

    13156 Social Ln, Winter Garden, FL 34787

    WELCOME HOME! You will fall in love with this beautiful home! 4 bedrooms, 2 baths, OPEN and SPLIT FLOOR PLAN, TILE and LAMINATE flooring throughout, NO CARPETS, LARGE FENCED BACKYARD with mature landscape. This adorable house has a Living Room and Dining Room combined and a Kitchen, Breakfast, and Family Room combined. This WELL MAINTAINED home has just received a FRESH and MODERN EXTERIOR PAINT.

    13156 Social Ln, Winter Garden, FL 34787
  • /30

    $2,700 per month

    • 3 Beds
    • 2.5 Baths
    • 1,881 Sq Ft
    • Townhouse for Rent

    7601 Ripplepointe Way, Windermere, FL 34786

    Live in one of Windermere’s most desirable communities! You cannot miss this lovely and beautifully maintained townhome in Windermere, Lake Burden. Spacious 3 bedroom, 3 1/2 bath with modern paint color at the walls, and ceramic flooring downstairs. Extra space at the first floor that could be used as office, TV room or play area. Amazing storage spaces, and all windows with blinds. Large open

    Ana Paula Teixeira ANA TEIXEIRA REALTY

    7601 Ripplepointe Way, Windermere, FL 34786

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