Winter Garden, FL Homes

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  $609,990 Pending

  • 4 Beds
  • 3 Baths
  • 2,083 Sq Ft

  Winter Garden, FL 34787

  Under Construction. Stylish Living in the Newbury 2083sqft, 4 bedrooms, a loft, 3 bathrooms and a 2-car garage. Step into this thoughtfully designed open-concept floor plan that effortlessly blends comfort, style, and modern convenience. This home features a convenient guest bedroom and full bathroom on the first floor, perfect for visiting family multi multi-generational living or a private home

  

  Cindy Sapp

  OLYMPUS EXECUTIVE REALTY INC

  (321) 248-9833

  Winter Garden, FL 34787
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  /20

  $2,367 per month

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Condo for Rent

  14200 Avalon Rd Unit SI ID1244724P, Winter Garden, FL 34787

  The advertised rate of $2,368/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 18, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  14200 Avalon Rd Unit SI ID1244724P, Winter Garden, FL 34787
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  $540,000 Sold Dec 02, 2025

  14342 White Moss Way, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,368 Sq Ft
  • Built 2015

  Last Sold Summary

  • 9% Below List Price
  • $228/SF
  • 81 Days On Market

  Current Estimated Value $542,719

  Last Listing Agent Silvia Kinkela SERHANT

  14342 White Moss Way, Winter Garden, FL 34787
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  Est $432,995 Not Listed For Sale

  1912 Portcastle Cir, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,857 Sq Ft
  • Built 2005

  1912 Portcastle Cir, Winter Garden, FL 34787

  Last Sold Summary

  • $234/SF
  • 22 Days On Market

  Last Sold Price $434,000

  Last Listing Agent Jeffrey Petch GECKO REALTY, INC
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  /54

  $444,990 Open Sat 1PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 1,644 Sq Ft

  13270 Serene Glade Rd, Winter Garden, FL 34787

  One or more photo(s) has been virtually staged. Under Construction. Sample Images Harbor Town Home – Stylish End Unit Living Beautiful end-unit townhome offering 1,644 sq. ft. of thoughtfully designed living space, featuring three bedrooms, two and a half baths, and a spacious two-car garage with a charming paver driveway. Step inside to impressive tall ceilings, enhancing the natural light and

  

  Cindy Sapp

  OLYMPUS EXECUTIVE REALTY INC

  (321) 450-1594

  13270 Serene Glade Rd, Winter Garden, FL 34787
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  /16

  $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
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  $584,000 Sold Oct 06, 2025

  15249 Purple Martin St, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,186 Sq Ft
  • Built 2017

  Last Sold Summary

  • 3% Below List Price
  • $267/SF
  • 29 Days On Market

  Current Estimated Value $572,879

  Last Listing Agent Diana Basch Connery MS LAND & BUILDING LLC

  15249 Purple Martin St, Winter Garden, FL 34787
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  Est $613,669 Not Listed For Sale

  1105 Harbor Hill St, Winter Garden, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,383 Sq Ft
  • Built 2001

  1105 Harbor Hill St, Winter Garden, FL 34787

  Last Sold Summary

  • 2% Below List Price
  • $263/SF
  • 9 Days On Market

  Last Sold Price $626,000

  Last Listing Agent Tennille Biggers KELLER WILLIAMS ELITE PARTNERS III REALTY
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  $599,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

  13356 Peaceful Melody Dr, Winter Garden, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. Sample Images This beautifully appointed Anna Maria offers 4 bedrooms, 2.5 bathrooms, and a two-car garage, all situated on a serene conservation home site with no rear neighbors—providing enhanced privacy and a true retreat feel. The main level features modern tile flooring throughout the main living area and an

  

  Cindy Sapp

  OLYMPUS EXECUTIVE REALTY INC

  (321) 587-3369

  13356 Peaceful Melody Dr, Winter Garden, FL 34787
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  /5

  $1,695 per month

  • 2 Beds
  • 1 Bath
  • 705 Sq Ft
  • House for Rent

  203 N Dillard St, Winter Garden, FL 34787

  Property Id: 2397260UNIT #2 WALK TO DOWNTOWN WINTER GARDEN/CROOKED CAN FOOD HALL/SHOPPING/MULTIPLE HOUSES OF WORSHIP NEARBY/LIBRARY ON E. PLANT STREET/POLICESTATION ON W. PLANT STREET. EXCELLENT WINTER GARDEN LOCATIONADORABLE PRIVATE 2 ROOM APARTMENT WITH WATER-SEWER AND HEAT INCLUDED. (1) ASSIGNED PARKING SPOT IN REAR PRIVATE PARKING LOTNEWER AC UNITS, NEWER LVP

  203 N Dillard St, Winter Garden, FL 34787
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  $390,000 Sold Aug 18, 2025

  15574 Murcott Blossom Blvd, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,868 Sq Ft
  • Built 2017

  Last Sold Summary

  • 13% Below List Price
  • $209/SF
  • 155 Days On Market

  Current Estimated Value $401,591

  Last Listing Agent Erica Diaz HOMEVEST REALTY

  15574 Murcott Blossom Blvd, Winter Garden, FL 34787
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  Est $931,394 Not Listed For Sale

  820 Duff Dr, Winter Garden, FL 34787

  • 5 Beds
  • 4 Baths
  • 3,863 Sq Ft
  • Built 2005

  820 Duff Dr, Winter Garden, FL 34787

  Last Sold Summary

  • 2% Below List Price
  • $246/SF
  • 2 Days On Market

  Last Sold Price $949,900

  Last Listing Agent Steven Sargent CONTEMPORARY REALTY GROUP
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  /29

  $747,999 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,833 Sq Ft

  Pallazio II Plan at Esplanade at McKinnon Groves - 60' Lot, Winter Garden, FL 34787

  From breezy open spaces to private retreats, the Pallazio II floor plan is designed for effortless luxury. This 1-story home features 3 bedrooms, 3.5 bathrooms, a 3-car garage and 2,833 square feet. Head through the courtyard that leads to the front porch and into a sweeping foyer to find beautiful open-concept living spaces. A great room flows into formal and casual dining areas, a modern

  Taylor Morrison Builder

  17705 Sedona St Unit 39548786, Winter Garden, FL 34787
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  /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
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  $1,700,000 Sold Jan 21, 2026

  9072 Bradleigh Dr, Winter Garden, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 3,750 Sq Ft
  • Built 2019

  Last Sold Summary

  • 10% Below List Price
  • $453/SF
  • 74 Days On Market

  Current Estimated Value $1,761,453

  Last Listing Agent Ronald Ziolkowski RE/MAX PRIME PROPERTIES

  9072 Bradleigh Dr, Winter Garden, FL 34787
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  Est $568,034 Not Listed For Sale

  14674 Black Cherry Trail, Winter Garden, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 2,527 Sq Ft
  • Built 2006

  14674 Black Cherry Trail, Winter Garden, FL 34787

  Last Sold Summary

  • 1% Above List Price
  • $223/SF
  • 0 Days On Market

  Last Sold Price $563,670

  Last Listing Agent Andrew Philippone INDEPENDENCE REALTY GROUP LLC
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  /19

  $735,990 New Construction

  • 3 - 5 Beds
  • 2.5 - 4.5 Baths
  • 2,791 Sq Ft

  Moseley II Plan at Northlake at Ovation - Traditional, Winter Garden, FL 34787

  The Moseley II is a thoughtfully designed two-story home with three bedrooms, two full bathrooms, one half bathroom, and a two-car garage. This plan features a dramatic two-story family room that creates a bright and open living space. The second-floor primary suite offers privacy and comfort, while additional flexible living areas provide room to relax or entertain. High ceilings, abundant

  Ashton Woods Builder

  17551 Lake Star Rd Unit 36476723, Winter Garden, FL 34787
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  /18

  $2,949 per month

  • 4 Beds
  • 2.5 Baths
  • 1,913 Sq Ft
  • House for Rent

  6440 Breeze Filled Ln, 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 $3046.90. That covers your base rent, $2949.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Community

  6440 Breeze Filled Ln, Winter Garden, FL 34787
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  $1,700,000 Sold Sep 11, 2025

  557 Lake Cove Pointe Cir, Winter Garden, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 4,176 Sq Ft
  • Built 2015

  Last Sold Summary

  • 6% Below List Price
  • $407/SF
  • 90 Days On Market

  Current Estimated Value $1,679,749

  Last Listing Agent Erica Diaz HOMEVEST REALTY

  557 Lake Cove Pointe Cir, Winter Garden, FL 34787
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  Est $490,113 Not Listed For Sale

  14638 Tullamore Loop, Winter Garden, FL 34787

  • 4 Beds
  • 2 Baths
  • 1,960 Sq Ft
  • Built 2004

  14638 Tullamore Loop, Winter Garden, FL 34787

  Last Sold Summary

  • 1% Above List Price
  • $247/SF
  • 16 Days On Market

  Last Sold Price $485,000

  Last Listing Agent Guilherme Mello EPIC REALTY
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  /38

  $819,900

  • 4 Beds
  • 4 Baths
  • 3,278 Sq Ft

  5427 Orange Orchard Dr, Winter Garden, FL 34787

  SELLER OFFERING UP TO $15,000 TOWARD BUYER’S CLOSING COSTS + ADDITIONAL PREFERRED LENDER CREDIT FOR RATE BUY-DOWN OR EXTRA CLOSING COSTS! Don’t miss this stunning 4-bedroom, 4-bathroom home located in the desirable Wincey Groves community in Winter Garden. This spacious residence features a functional 3-way split floor plan, a massive upstairs loft, and a bonus room currently used as a gym with

  Julimar Barreiro Pastrana SERHANT

  5427 Orange Orchard Dr, Winter Garden, FL 34787
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  /27

  $2,995 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
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  $1,000,000 Sold Aug 21, 2025

  15900 Citrus Knoll Dr, Winter Garden, FL 34787

  • 5 Beds
  • 3 Baths
  • 3,844 Sq Ft
  • Built 2015

  Last Sold Summary

  • 13% Below List Price
  • $260/SF
  • 48 Days On Market

  Current Estimated Value $1,023,089

  Last Listing Agent Ronald Ziolkowski RE/MAX PRIME PROPERTIES

  15900 Citrus Knoll Dr, Winter Garden, FL 34787
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  Est $801,231 Not Listed For Sale

  678 Cascading Creek Ln, Winter Garden, FL 34787

  • 4 Beds
  • 4 Baths
  • 3,659 Sq Ft
  • Built 2005

  678 Cascading Creek Ln, Winter Garden, FL 34787

  Last Sold Summary

  • $219/SF
  • 3 Days On Market

  Last Sold Price $800,000

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC
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  /17

  $399,900

  • 2 Beds
  • 2 Baths
  • 1,265 Sq Ft

  14501 Grove Resort Ave Unit 1318, Winter Garden, FL 34787

  OWN this full POOL-VIEW condominium in the MAIN building!!! As you enter this 3rd floor two bedroom, two bathroom unit, an unobstructed view to the Springs Pool welcomes you in the Premier Tower or Building One. What an amazing view!!! In the evenings, you may enjoy Disney's fireworks from your balcony or bedrooms!!! The unit is located in Tower One, where you find the lobby, concierge,

  Carlos Selmo PORTAL ORLANDO REALTY, LLC

  14501 Grove Resort Ave Unit 1318, Winter Garden, FL 34787
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  /20

  $2,299 per month

  • 3 Beds
  • 2 Baths
  • 1,291 Sq Ft
  • Condo for Rent

  14200 Avalon Rd Unit SI ID1244728P, Winter Garden, FL 34787

  The advertised rate of $2,299/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 17, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  14200 Avalon Rd Unit SI ID1244728P, Winter Garden, FL 34787
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  $1,075,000 Sold May 19, 2025

  16750 Toccoa Row, Winter Garden, FL 34787

  • 5 Beds
  • 5 Baths
  • 3,861 Sq Ft
  • Built 2020

  Last Sold Summary

  • 2% Below List Price
  • $278/SF
  • 66 Days On Market

  Current Estimated Value $1,072,476

  Last Listing Agent Denise Batista ALLUX REAL ESTATE LLC

  16750 Toccoa Row, Winter Garden, FL 34787
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  Est $384,059 Not Listed For Sale

  128 Tildenville School Rd, Winter Garden, FL 34787

  • 3 Beds
  • 1 Bath
  • 1,026 Sq Ft
  • Built 1957

  128 Tildenville School Rd, Winter Garden, FL 34787

  Last Sold Summary

  • $376/SF
  • 2 Days On Market

  Last Sold Price $385,500

  Last Listing Agent Ruthanne Martin REVEL REALTY LLC
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  /40

  $600,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,181 Sq Ft

  10356 Atwater Bay Dr, Winter Garden, FL 34787

  Under contract-accepting backup offers. Live the beautiful, low maintenance Florida lifestyle in sought-after Waterleigh! Situated on a premium corner lot, this like new Arbor model offers 4 bedrooms and 3 full baths all on one level with a modern open concept design and impressive upgrades throughout. Enjoy wood look porcelain tile flooring, designer lighting and fans, and stunning floor to

  Simon Simaan THE SIMON SIMAAN GROUP

  10356 Atwater Bay Dr, Winter Garden, FL 34787
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  /42

  $3,350 per month

  • 4 Beds
  • 3 Baths
  • 2,768 Sq Ft
  • House for Rent

  5395 Bowman Dr, Winter Garden, FL 34787

  Elegant 4-Bedroom Home in Overlook at Hamlin – Resort Amenities & Prime Location! Welcome to your next home in the highly sought-after Overlook at Hamlin community, where comfort, style, and convenience meet. This beautifully crafted one-story 4-bedroom, 3-bath residence features a bright open-concept layout with abundant natural light, stunning flooring, and spacious living and dining areas

  Jacob Hara TRANSCEND REALTY

  5395 Bowman Dr, Winter Garden, FL 34787
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  $439,990 Sold Dec 30, 2025

  15451 Bay Bridge St, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,693 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $260/SF
  • 35 Days On Market

  Current Estimated Value $438,642

  Last Listing Agent Stacie Brown Kelly KELLER WILLIAMS ADVANTAGE REALTY

  15451 Bay Bridge St, Winter Garden, FL 34787
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  Est $220,775 Not Listed For Sale

  1015 Stucki Terrace, Winter Garden, FL 34787

  • 2 Beds
  • 2 Baths
  • 938 Sq Ft
  • Built 1987

  1015 Stucki Terrace, Winter Garden, FL 34787

  Last Sold Summary

  • 2% Below List Price
  • $241/SF
  • 7 Days On Market

  Last Sold Price $226,000

  Last Listing Agent Rhonda Moretti WATSON REALTY CORP., REALTORS
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  /2

  $895,990 New Construction

  • 4 - 6 Beds
  • 3.5 Baths
  • 3,458 Sq Ft

  Superior Plan at Northlake at Ovation - Estate, Winter Garden, FL 34787

  The Superior is a two-story home offering four bedrooms, three full bathrooms, one half bathroom, and a three-car garage. This spacious plan features an open-concept kitchen and family room perfect for gatherings. The private second-floor primary suite includes a walk-in closet and luxurious bath, complemented by additional bedrooms, a versatile loft, and convenient laundry room. Modern finishes,

  Ashton Woods Builder

  17551 Lake Star Rd Unit 36646269, Winter Garden, FL 34787
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  /12

  $2,570 per month

  • 3 Beds
  • 2.5 Baths
  • 1,541 Sq Ft
  • House for Rent

  15319 Torpoint Rd, Winter Garden, FL 34787

  Special security deposit offer: Pay just 50% of your base rent as your security deposit (taxes and fees not included), valid for new applicants who sign a 12-month lease by March 31, 2026. 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

  15319 Torpoint Rd, Winter Garden, FL 34787
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  $540,000 Sold Oct 28, 2025

  660 Egret Place Dr, Winter Garden, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,647 Sq Ft
  • Built 2014

  Last Sold Summary

  • 10% Below List Price
  • $204/SF
  • 171 Days On Market

  Current Estimated Value $556,288

  Last Listing Agent Gilbert Ramos EXP REALTY LLC

  660 Egret Place Dr, Winter Garden, FL 34787
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  Est $203,465 Not Listed For Sale

  1266 Westside Dr, Winter Garden, FL 34787

  • 2 Beds
  • 1 Bath
  • 761 Sq Ft
  • Built 1987

  1266 Westside Dr, Winter Garden, FL 34787

  Last Sold Summary

  • 5% Below List Price
  • $283/SF
  • 8 Days On Market

  Last Sold Price $215,000

  Last Listing Agent Jason Price RE/MAX
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  /7

  $456,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,675 Sq Ft

  Walden II Plan at Northlake at Ovation - Townhomes, Winter Garden, FL 34787

  The Walden II is a two-story townhome offering three bedrooms, two full bathrooms, one half bathroom, and a two-car garage. The open-concept main floor connects the kitchen, dining, and family rooms, creating a bright and functional space. Upstairs, the private primary suite offers comfort and privacy, accompanied by two additional bedrooms and a conveniently located laundry room. Thoughtful

  Ashton Woods Builder

  17551 Lake Star Rd Unit 36470489, Winter Garden, FL 34787
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  $3,000 per month

  • 4 Beds
  • 2.5 Baths
  • 2,011 Sq Ft
  • House for Rent

  14311 Braemar St, Winter Garden, FL 34787

  Spacious two-story house available for rent, ideal for those seeking comfort, practicality, and an excellent location! The property features 4 bedrooms, 2 full bathrooms, and 1 powder room, distributed in a modern open-concept style, providing integrated, spacious, and well-lit environments. A charming veranda welcomes you right at the entrance. The living room is spacious and integrated with the

  Umberto Da Cunha Neto WRA BUSINESS & REAL ESTATE

  14311 Braemar St, Winter Garden, FL 34787
• 

  $485,000 Sold Sep 23, 2025

  11960 Bracco St, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,678 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $289/SF
  • 326 Days On Market

  Current Estimated Value $480,610

  11960 Bracco St, Winter Garden, FL 34787
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  Est $231,242 Not Listed For Sale

  1170 Westside Dr, Winter Garden, FL 34787

  • 2 Beds
  • 2 Baths
  • 814 Sq Ft
  • Built 1986

  1170 Westside Dr, Winter Garden, FL 34787

  Last Sold Summary

  • 7% Below List Price
  • $306/SF
  • 46 Days On Market

  Last Sold Price $249,000

  Last Listing Agent Carina Davis LAKESIDE REALTY WINDERMERE INC

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