Homes near Windermere Preparatory School

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$490,990 New Construction
- 3 Beds
- 3.5 Baths
- 2,072 Sq Ft
Haines II Plan at Parkview at Hamlin, Winter Garden, FL 34787

The Haines II is a three-story townhome offering three bedrooms, three full bathrooms, one half bathroom, and a two-car garage. This thoughtfully designed plan features open-concept living on the main floor, spacious private suites on the upper levels, and a ground-level flex space perfect for a home office or guest area. A modern layout ideal for both everyday living and entertaining. Additional

Ashton Woods Builder

15501 Hamlin Park Dr Unit 36452938, Winter Garden, FL 34787
/30
$2,600 per month
- 3 Beds
- 2 Baths
- 1,588 Sq Ft
- House for Rent
12144 Stoneleigh Aly, Winter Garden, FL 34787

Welcome to this beautiful 3-bedroom, 2.5-bath home located in the highly sought-after Winter Garden area. This property offers a modern and spacious layout featuring a bright open living area, a well-appointed kitchen with stainless steel appliances, and a dining space perfect for everyday living and entertaining. All bedrooms are generously sized, and the primary suite includes a walk-in closet

Ricardo Molina TALENT REALTY SOLUTIONS

12144 Stoneleigh Aly, Winter Garden, FL 34787
/2
$530,000 Sold Jan 20, 2026

2332 Black Lake Blvd, Winter Garden, FL 34787
- 4 Beds
- 3 Baths
- 1,986 Sq Ft
- Built 2006
Last Sold Summary
- 4% Below List Price
- $267/SF
- 56 Days On Market
Current Estimated Value $530,529

Last Listing Agent David Johnston CREEGAN GROUP

2332 Black Lake Blvd, Winter Garden, FL 34787

/38
Est $764,954 Not Listed For Sale

1658 Holcomb Creek St, Winter Garden, FL 34787
- 4 Beds
- 3.5 Baths
- 2,840 Sq Ft
- Built 2018
1658 Holcomb Creek St, Winter Garden, FL 34787

Last Sold Summary
- 4% Below List Price
- $280/SF
- 12 Days On Market
Last Sold Price $795,000

Last Listing Agent Krushna Patel COMPASS FLORIDA LLC

/61
$499,000
- 4 Beds
- 2.5 Baths
- 2,092 Sq Ft
10624 Reams Rd, Windermere, FL 34786

Welcome to this beautiful 4-bedroom, 2.5-bath home in the highly desirable Windermere Trails community. Just minutes from Disney World, you can enjoy nightly fireworks right from your front porch. The kitchen features 42" maple cabinets, granite countertops, and under-cabinet lighting. An open-concept design connects the spacious living and with the kitchen, perfect for entertaining. The primary

Jeff Taulbee CHARLES RUTENBERG REALTY ORLANDO

10624 Reams Rd, Windermere, FL 34786
/20
$3,000 per month
- 4 Beds
- 3 Baths
- 2,345 Sq Ft
- House for Rent
5019 Blue Major Dr, Windermere, FL 34786

Welcome home to this beautifully maintained property in Windermere’s sought-after Summerport community. Enjoy a chef-inspired kitchen complete with solid countertops, updated stainless steel appliances, and a gas range—perfect for everyday living and entertaining. New interior paint, stylish flooring throughout, and upgraded lighting and bathroom fixtures make this home the perfect rental!

Alex Sadowski KELLER WILLIAMS REALTY AT THE PARKS

5019 Blue Major Dr, Windermere, FL 34786
/2
$605,000 Sold Nov 14, 2025

14563 Bahama Swallow Blvd, Winter Garden, FL 34787
- 3 Beds
- 2.5 Baths
- 2,750 Sq Ft
- Built 2012
Last Sold Summary
- 8% Below List Price
- $220/SF
- 157 Days On Market
Current Estimated Value $602,034

Last Listing Agent Wanda Woolfolk FONSECA WOOLFOLK REALTY LLC

14563 Bahama Swallow Blvd, Winter Garden, FL 34787

/89
Est $671,662 Not Listed For Sale

14633 Magnolia Ridge Loop, Winter Garden, FL 34787
- 4 Beds
- 3 Baths
- 2,775 Sq Ft
- Built 2018
14633 Magnolia Ridge Loop, Winter Garden, FL 34787

Last Sold Summary
- 6% Below List Price
- $259/SF
- 108 Days On Market
Last Sold Price $718,000

Last Listing Agent Mariana Nossa WRA BUSINESS & REAL ESTATE

/30
$649,000
- 3 Beds
- 2 Baths
- 2,147 Sq Ft
13622 Darchance Rd, Windermere, FL 34786

Welcome home to Berkshire Park. This 3bedroom, 2bath residence offers a balance of comfort and convenience in a quiet residential setting. Ideally located just minutes from world-class attractions including Walt Disney World, as well as shopping, dining, and major highways, this property places you at the center of Central Florida living. The community is surrounded by nearby schools, adding

Javin Lopez AVANTI WAY REALTY LLC

13622 Darchance Rd, Windermere, FL 34786
/36
$4,275 per month
- 6 Beds
- 3.5 Baths
- 3,841 Sq Ft
- House for Rent
7403 Fairgrove Ave, Windermere, FL 34786

Spacious 6-bedroom, 3.5-bath unfurnished home offering 3,841 sq ft in the desirable Windermere Sound community. This well-designed floor plan features a downstairs primary bedroom, a large upstairs loft, generously sized bedrooms with walk-in closets, an office area and an expansive kitchen complete with a walk-in butler pantry and ample cabinet space—perfect for entertaining and everyday living.

Sunny Pabla PABLA PROPERTIES

7403 Fairgrove Ave, Windermere, FL 34786
/2
$930,000 Sold Nov 10, 2025

5141 Autumn Ridge Ln, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,390 Sq Ft
- Built 1990
Last Sold Summary
- 2% Below List Price
- $389/SF
- 91 Days On Market
Current Estimated Value $907,353

Last Listing Agent Deb Schroeder INFINITY REALTY GROUP LLC

5141 Autumn Ridge Ln, Windermere, FL 34786

/67
Est $1,607,870 Not Listed For Sale

1220 Estancia Woods Loop, Windermere, FL 34786
- 4 Beds
- 5 Baths
- 4,007 Sq Ft
- Built 2018
1220 Estancia Woods Loop, Windermere, FL 34786

Last Sold Summary
- 5% Above List Price
- $381/SF
- 72 Days On Market
Last Sold Price $1,525,000

Last Listing Agent Angela Rodriguez DREAM FINDERS REALTY GROUP CORP

/3
$742,990 New Construction
- 4 Beds
- 3.5 Baths
- 3,291 Sq Ft
Tidewater With Bonus Plan at Hamlin Meadows - 60' Homesites, Winter Garden, FL

The Tidewater with Bonus floorplan offers a versatile and spacious two-story layout, featuring 4 bedrooms and 3.5 bathrooms. Spanning 3,289 sq. ft., this home includes a large two-car garage for ample storage and convenience. The first floor boasts an inviting great room connected to an open kitchen and dining area, perfect for entertaining. The owner’s suite provides a private retreat with a

Dream Finders Homes Builder

0 Hamlin Meadows St Unit 39127942, Winter Garden, FL
/71
$4,950 per month
- 5 Beds
- 5 Baths
- 3,416 Sq Ft
- House for Rent
17850 Hither Hills Cir, Winter Garden, FL 34787

Executive Rental Available – Lawncare & HOA Included! Exquisite Lakefront Home: 5 Beds, 5 Baths, built in 2023 by DR Horton. Situated on over half an acre with panoramic views of Lake Apopka, the 5th largest lake in Florida. Approved for a dock and pool! Luxurious kitchen, open family room, main-level bedroom, and bath. Upstairs: primary suite and additional rooms. Smart fans in all bedrooms,

Ben Becton KELLER WILLIAMS REALTY SMART

17850 Hither Hills Cir, Winter Garden, FL 34787
/2
$780,000 Sold Jun 12, 2025

14027 Fairway Willow Ln, Winter Garden, FL 34787
- 3 Beds
- 2.5 Baths
- 2,783 Sq Ft
- Built 2006
Last Sold Summary
- 2% Below List Price
- $280/SF
- 32 Days On Market
Current Estimated Value $773,233

Last Listing Agent Mark Raumaker SERHANT

14027 Fairway Willow Ln, Winter Garden, FL 34787

/17
Est $652,640 Not Listed For Sale

1348 Lake Olivia Ln, Windermere, FL 34786
- Built 2018
1348 Lake Olivia Ln, Windermere, FL 34786

Last Sold Summary
- 2% Below List Price
- $132/SF
- 530 Days On Market
Last Sold Price $669,000

Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

/33
$565,000 Pending
- 3 Beds
- 2.5 Baths
- 2,280 Sq Ft
15201 Murcott Blossom Blvd, Winter Garden, FL 34787

Under contract-accepting backup offers. Welcome Home!This beautiful 3-bedroom, 2.5-bath home is perfect for both everyday living and entertaining. As you enter, the open-concept floor plan and soaring vaulted ceilings create a bright, welcoming atmosphere. The executive kitchen is a standout, featuring quartz countertops, stainless steel appliances, a convection cooktop, a spacious center

Ted Wangsanutr TED WANGSANUTR

15201 Murcott Blossom Blvd, Winter Garden, FL 34787
/40
$2,850 per month
- 4 Beds
- 2.5 Baths
- 2,072 Sq Ft
- House for Rent
9377 Meadow Hunt Way, Winter Garden, FL 34787

Available February 2026.Welcome to 9377 Meadow Hunt Way, perfectly located in the highly desirable Winter Garden 34787 — one of Central Florida’s most sought-after communities. This home offers the ideal combination of tranquility and convenience. Just minutes from Highway 429 and the Florida Turnpike, the location provides easy access to Downtown Orlando, Disney, Windermere, and Clermont.

Caroline Valentino GLASSTONE GROUP INC

9377 Meadow Hunt Way, Winter Garden, FL 34787
/2
$2,125,000 Sold Nov 24, 2025

16098 Johns Lake Overlook Dr, Winter Garden, FL 34787
- 5 Beds
- 4.5 Baths
- 4,434 Sq Ft
- Built 2015
Last Sold Summary
- 11% Below List Price
- $479/SF
- 92 Days On Market
Current Estimated Value $2,115,268

Last Listing Agent Debbie Sansing HAMLIN REALTY

16098 Johns Lake Overlook Dr, Winter Garden, FL 34787

/84
Est $841,085 Not Listed For Sale

5060 Palmetto Park Dr, Winter Garden, FL 34787
- 4 Beds
- 3.5 Baths
- 3,866 Sq Ft
- Built 2017
5060 Palmetto Park Dr, Winter Garden, FL 34787

Last Sold Summary
- 7% Below List Price
- $233/SF
- 32 Days On Market
Last Sold Price $899,999

Last Listing Agent Lisa Foster PREFERRED REAL ESTATE BROKERS

/50
$4,200,000
- 5 Beds
- 6 Baths
- 4,600 Sq Ft
9916 Lone Tree Ln, Orlando, FL 32836

Located on the world-renowned Butler Chain of Lakes, this extraordinary lakefront retreat at 9916 Lone Tree Lane is set on a private peninsula with 270 water views across Lake Tibet, Lake Sheen, and the connecting canal. Perfectly oriented south, it captures stunning sunrises, glowing sunsets, and nightly Disney fireworks. Designed for effortless indoor-outdoor living, walls of glass frame

Chad Going Serhant

9916 Lone Tree Ln, Orlando, FL 32836
/19
$2,500 per month
- 3 Beds
- 2.5 Baths
- 1,540 Sq Ft
- Townhouse for Rent
7843 Hardenton St, Windermere, FL 34786

Townhome Windermere area 3 Bedroom and 2.5 Bathroom, 2 car garage, 2 story unit. The kitchen cabinets 42", with quartz counters, island/breakfast bar, and stainless steel appliances, open private patio. Wickham Park has a community pool, clubhouse and parks. Great location, close to street mall and supermarket, Close to Disney, Winter Garden Village and major highways (529, turnpike, I4). Close

Franca Troisi MY REALTY GROUP, LLC.

7843 Hardenton St, Windermere, FL 34786
/2
$518,000 Sold May 14, 2025

5014 Wise Bird Dr, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,342 Sq Ft
- Built 2004
Last Sold Summary
- 13% Below List Price
- $221/SF
- 102 Days On Market
Current Estimated Value $526,119

Last Listing Agent Hong Lu CHARLES RUTENBERG REALTY ORLANDO

5014 Wise Bird Dr, Windermere, FL 34786

/24
Est $332,300 Not Listed For Sale

14038 Avenue of the Groves, Winter Garden, FL 34787
- 2 Beds
- 2.5 Baths
- 1,263 Sq Ft
- Built 2011
14038 Avenue of the Groves, Winter Garden, FL 34787

Last Sold Summary
- 5% Below List Price
- $277/SF
- 31 Days On Market
Last Sold Price $350,000

Last Listing Agent Irina Paul FUTURE HOME REALTY INC

/2
$3,200,000
- Land
- 6.76 Acres
- $473,373 per Acre
934 Roberson Rd, Ocoee, FL 34761

PROPERTY DESCRIPTION - We are pleased to present a premier investment opportunity at 934 Roberson Road in Ocoee, just west of Orlando. This 6.76-acre parcel of vacant land comes with full site plan approval from the City of Ocoee for a 120-bed assisted living facility, making it an exceptional prospect for those looking to capitalize on the burgeoning demand for senior care services in Central

Chase Collier Eshenbaugh Land Company

934 Roberson Rd, Ocoee, FL 34761
/29
$2,900 per month
- 4 Beds
- 3.5 Baths
- 1,914 Sq Ft
- Townhouse for Rent
7000 Twilight Bay Dr, Winter Garden, FL 34787

One or more photo(s) has been virtually staged. Welcome to this beautiful home in the desirable Mezzano community of Winter Garden, offering a spacious multi-level floor plan designed for both comfort and functionality. Inside, you’ll find bright, open living areas with modern finishes that create a warm and inviting atmosphere. The main living space flows seamlessly into the dining area and

Cesar Sanchez LA ROSA REALTY ORLANDO LLC

7000 Twilight Bay Dr, Winter Garden, FL 34787
/2
$660,000 Sold Apr 21, 2025

14657 Winter Stay Dr, Winter Garden, FL 34787
- 4 Beds
- 3.5 Baths
- 2,935 Sq Ft
- Built 2018
Last Sold Summary
- 17% Below List Price
- $225/SF
- 55 Days On Market
Current Estimated Value $691,261

Last Listing Agent Huizi Li MULTI CHOICE REALTY LLC

14657 Winter Stay Dr, Winter Garden, FL 34787

/2
Est $513,410 Not Listed For Sale

6315 Golden Dewdrop Trail, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,984 Sq Ft
- Built 2012
6315 Golden Dewdrop Trail, Windermere, FL 34786

Last Sold Summary
- 3% Above List Price
- $252/SF
- 46 Days On Market
Last Sold Price $500,000

Last Listing Agent Sandy Jones CLOCK TOWER REALTY

/11
$299,000
- 2 Beds
- 2 Baths
- 1,212 Sq Ft
7516 Sugar Bend Dr, Orlando, FL 32819

Welcome to your next home in the highly desirable Dr. Phillips area! This beautifully maintained condo offers the perfect blend of comfort, convenience, and location. Featuring a bright and open floor plan, this residence is ideal for both everyday living and entertaining. Enjoy a spacious living area, well-appointed kitchen, and generously sized bedrooms designed for relaxation. The home is

Mary Carpousis BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

7516 Sugar Bend Dr, Orlando, FL 32819
/27
$2,800 per month
- 3 Beds
- 2.5 Baths
- 1,956 Sq Ft
- Townhouse for Rent
1519 Priory Cir, Winter Garden, FL 34787

One or more photo(s) has been virtually staged. Now available for immediate move-in in the highly sought after Westbrook at Stoneybrook West community in Winter Garden. This spacious 3 bedroom, 2.5 bath townhome with a 2 car garage and versatile loft offers the ideal blend of comfort, function, and location. Step inside to a bright, open layout with wood laminate flooring and a seamless flow from

Peter Luu REAL BROKER, LLC

1519 Priory Cir, Winter Garden, FL 34787
/2
$925,000 Sold Apr 09, 2026

15210 Southern Martin St, Winter Garden, FL 34787
- 5 Beds
- 4 Baths
- 3,728 Sq Ft
- Built 2017
Last Sold Summary
- 1% Below List Price
- $248/SF
- 1 Day On Market
Current Estimated Value $896,701

Last Listing Agent Misty Griffin DOUGLAS ELLIMAN

15210 Southern Martin St, Winter Garden, FL 34787

/2
Est $3,103,363 Not Listed For Sale

4124 Isabella Cir, Windermere, FL 34786
- 6 Beds
- 8 Baths
- 6,842 Sq Ft
- Built 2016
4124 Isabella Cir, Windermere, FL 34786

Last Sold Summary
- 7% Below List Price
- $490/SF
- 59 Days On Market
Last Sold Price $3,350,000

Last Listing Agent Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

/49
$1,200,000
- 4 Beds
- 4 Baths
- 2,787 Sq Ft
1361 Whitney Isles Dr, Windermere, FL 34786

Stunning residence with a private fenced backyard, located in the highly sought-after gated community of Belmere in Windermere, just minutes from the town center. Featuring 4 bedrooms, 4 bathrooms, and approximately 2,800 sq. ft. of air-conditioned living space, this home immediately captivates with its elegant Mediterranean architecture and lush tropical landscaping. Fully renovated this year,

Gabriel Mantovani ALVES AND HOWELL REALTY

1361 Whitney Isles Dr, Windermere, FL 34786
/40
$5,500 per month
- 4 Beds
- 4.5 Baths
- 3,512 Sq Ft
- House for Rent
11560 Claymont Cir, Windermere, FL 34786

Welcome to this spacious, fully furnished, 4-bedroom, 4.5-bathroom home nestled within a desirable gated golf community of Keene's Pointe. Thoughtfully designed for comfort and functionality, this impressive residence features a first-floor primary suite offering privacy and convenience, complete with a well-appointed ensuite bath. The home boasts generous living areas filled with natural light,

Rose Sepulveda-Morales WATSON REALTY CORP.

11560 Claymont Cir, Windermere, FL 34786
/2
$695,000 Sold Apr 30, 2025

342 Lake Amberleigh Dr, Winter Garden, FL 34787
- 5 Beds
- 2.5 Baths
- 3,239 Sq Ft
- Built 2001
Last Sold Summary
- 1% Below List Price
- $215/SF
- 4 Days On Market
Current Estimated Value $702,332

Last Listing Agent Chad Williams OLYMPUS EXECUTIVE REALTY INC

342 Lake Amberleigh Dr, Winter Garden, FL 34787

/43
Est $530,466 Not Listed For Sale

11650 Black Rail St, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,139 Sq Ft
- Built 2012
11650 Black Rail St, Windermere, FL 34786

Last Sold Summary
- 2% Above List Price
- $243/SF
- 1 Day On Market
Last Sold Price $520,000

Last Listing Agent Julie Fernandez OAK AVENUE REAL ESTATE LLC

/99
$1,150,000
- 4 Beds
- 3.5 Baths
- 3,585 Sq Ft
4866 Keeneland Cir, Orlando, FL 32819

Price Adjustment. 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,

RAVINDRANATH PERSAD PROPERTY OUTLET INTERNATIONAL

4866 Keeneland Cir, Orlando, FL 32819
/25
$2,800 per month
- 3 Beds
- 2.5 Baths
- 1,545 Sq Ft
- Townhouse for Rent
7609 Sutherton Ln, Windermere, FL 34786

Fully Renovated Corner Unit Townhome for Rent in Wickham Park – Windermere Beautiful 3-bedroom, 2.5-bath corner unit townhome, offering extra privacy, more natural light, and an enhanced sense of space, located in the desirable Wickham Park community in Windermere. This home features granite countertops, solid wood cabinets, stainless steel appliances news and a spacious open-concept living and

Vivian Azuaje 1 ELEVEN REALTY

7609 Sutherton Ln, Windermere, FL 34786
/2
$745,000 Sold Jul 28, 2025

9676 Wild Oak Dr, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,856 Sq Ft
- Built 1977
Last Sold Summary
- 21% Below List Price
- $261/SF
- 102 Days On Market
Current Estimated Value $774,277

Last Listing Agent Hardy Edwards, III BHHS FLORIDA REALTY

9676 Wild Oak Dr, Windermere, FL 34786

/26
Est $640,668 Not Listed For Sale

14605 Bahama Swallow Blvd, Winter Garden, FL 34787
- 3 Beds
- 2.5 Baths
- 2,828 Sq Ft
- Built 2012
14605 Bahama Swallow Blvd, Winter Garden, FL 34787

Last Sold Summary
- 2% Above List Price
- $223/SF
- 6 Days On Market
Last Sold Price $630,000

Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

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