Winter Garden, FL Homes

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  /57

  $639,000

  • 4 Beds
  • 3 Baths
  • 2,274 Sq Ft

  8266 Purple Sandpiper Ave, Winter Garden, FL 34787

  **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 8266 Purple Sandpiper Avenue in Winter Garden. This 4 bedroom, 3 bath home features a comfortable layout and plenty of space to fit different lifestyles. Inside you'll find an open living area that brings the

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 342-3506

  8266 Purple Sandpiper Ave, Winter Garden, FL 34787
• 

  

  

  /14

  $2,950 Per Month

  • 4 Beds
  • 3 Baths
  • 1,846 Sq Ft
  • Townhouse for Rent

  15250 Groveside Rd, Winter Garden, FL 34787

  Property Id: 2539292Live in the heart of one of Central Florida’s most desirable areas — Hamlin in Winter Garden! This brand-new luxury townhouse for rent features the popular three-story floorplan with a modern farmhouse exterior, offering 3 bedrooms, 2.5 bathrooms, and 1,846 sq. ft. of stylish living space. Enjoy an open-concept design with luxury vinyl plank flooring, a kitchen with

  (689) 333-6568

  15250 Groveside Rd, Winter Garden, FL 34787
• 

  

  /2

  $900,000

  Sold May 19, 2026

  15324 Gilligan Ct, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,794 Sq Ft
  • Built 2020

  Last Sold Summary

  • 5% Below List Price
  • $322/SF
  • 18 Days On Market

  Current Estimated Value $935,021

  Last Listing Agent Gretchen Carlson REAL ESTATE HOUSE FL INC

  15324 Gilligan Ct, Winter Garden, FL 34787
• 

  

  /2

  Est $1,400,451

  Not Listed For Sale

  17011 Wingspread Loop, Winter Garden, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 4,722 Sq Ft
  • Built 2021

  17011 Wingspread Loop, Winter Garden, FL 34787

  Last Sold Summary

  • 21 Days On Market
• 

  

  

  /23

  $594,000

  $6K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,695 Sq Ft

  15043 Pigeon Plum Ln, Winter Garden, FL 34787

  Welcome to this beautifully maintained 4-bedroom, 3.5-bath home located in the desirable Winter Garden area. This spacious residence offers a well-designed floor plan with generous living areas, ideal for both everyday living and entertaining. The home features a bright and open layout with abundant natural light, a large kitchen with ample cabinetry and counter space, and a seamless flow into

  

  Ceila Morales

  EXP REALTY LLC

  (321) 475-1948

  15043 Pigeon Plum Ln, Winter Garden, FL 34787
• 

  

  /20

  $2,804

  Total Monthly Price

  • 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 $2,805/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 8, 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

  (321) 248-9319

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

  /2

  $929,500

  Sold Dec 03, 2025

  17234 Cork St, Winter Garden, FL 34787

  • 3 Beds
  • 2 Baths
  • 2,325 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $400/SF
  • 20 Days On Market

  Current Estimated Value $926,203

  Last Listing Agent Jaime Galeoto FLORIDA REALTY RESULTS LLC

  17234 Cork St, Winter Garden, FL 34787
• 

  /2

  Est $395,577

  Not Listed For Sale

  13245 Shore Dr, Winter Garden, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft
  • Built 1990

  13245 Shore Dr, Winter Garden, FL 34787

  Last Sold Summary

  • 11 Days On Market
• 

  

  /52

  $750,000

  • 5 Beds
  • 3 Baths
  • 3,747 Sq Ft

  2205 Wintermere Pointe Dr, Winter Garden, FL 34787

  Located in the GATED community of Wintermere Pointe in Winter Garden, FL, this spacious .25 acre, 5-bedroom, 3-bath pool home for sale in Winter Garden offers nearly 3,750 square feet of well-designed living space just minutes from Winter Garden Village, Windermere, Walt Disney World, AdventHealth Winter Garden, SR 429, and the Florida Turnpike. Designed for both everyday living and entertaining,

  

  Alexis Bress

  EXP REALTY LLC

  (321) 463-7756

  2205 Wintermere Pointe Dr, Winter Garden, FL 34787
• 

  /2

  $2,850 Per Month

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft
  • Townhouse for Rent

  11060 Hanlon Ter Aly, Winter Garden, FL 34787

  Property Id: 2540020Welcome to your new home at 11060 Hanlon Terrace Aly! This stunning single unit property in Winter Garden, FL offers all the amenities you could ask for - dishwasher, oven, microwave, washer, dryer, and more. With a spacious garage, fenced yard, and security cameras, you'll feel safe and comfortable in this beautiful home. Don't miss out on this opportunity - schedule

  (407) 974-7767

  11060 Hanlon Ter Aly, Winter Garden, FL 34787
• 

  /2

  $902,500

  Sold Apr 08, 2026

  149 S Park Ave, Winter Garden, FL 34787

  • 3 Beds
  • 3.5 Baths
  • 2,938 Sq Ft
  • Built 2019

  Last Sold Summary

  • 18% Below List Price
  • $307/SF
  • 222 Days On Market

  Current Estimated Value $922,040

  Last Listing Agent Brigitte Knott CHARLES RUTENBERG REALTY ORLANDO

  149 S Park Ave, Winter Garden, FL 34787
• 

  /2

  Est $312,248

  Not Listed For Sale

  13515 Daniels Landing Cir, Winter Garden, FL 34787

  • 2 Beds
  • 2.5 Baths
  • 1,341 Sq Ft
  • Built 2004

  13515 Daniels Landing Cir, Winter Garden, FL 34787

  Last Sold Summary

  • 20 Days On Market
• 

  

  /69

  $1,200,000

  • 6 Beds
  • 4 Baths
  • 4,247 Sq Ft

  1812 Lake Roberts Landing Dr, Winter Garden, FL 34787

  Experience elevated living perfectly situated on a private conservation homesite with no rear neighbors in the gated community of Lake Roberts Landing in Winter Garden. This fully renovated luxury pool home offers an exceptional blend of privacy, elegance, and convenience in the heart of Winter Garden. Spanning over 4,200 square feet, this move-in-ready home features 6 bedrooms, 4 bathrooms, a

  

  Alexis Bress

  EXP REALTY LLC

  (321) 379-8194

  1812 Lake Roberts Landing Dr, Winter Garden, FL 34787
• 

  

  /20

  $3,120

  Total Monthly Price

  • 4 Beds
  • 2.5 Baths
  • 2,834 Sq Ft
  • House for Rent

  593 First Cape Coral Dr, Winter Garden, FL 34787

  Now offering 22-month leases. Sign today and lock in today’s low rate for the next 22 months! Offer valid for new applicants who sign a 22-month lease by June 30th, 2026. Base rent will remain at the 12-month lease rate for the duration of the 22-month term. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This property is

  (321) 392-6292

  593 First Cape Coral Dr, Winter Garden, FL 34787
• 

  /2

  $485,000

  Sold Apr 17, 2026

  12272 Bracco St, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,788 Sq Ft
  • Built 2024

  Last Sold Summary

  • 9% Below List Price
  • $271/SF
  • 315 Days On Market

  Current Estimated Value $482,577

  Last Listing Agent Dana Gold RE/MAX ASSURED

  12272 Bracco St, Winter Garden, FL 34787
• 

  /2

  Est $332,365

  Not Listed For Sale

  1318 Daniels Cove Dr, Winter Garden, FL 34787

  • 4 Beds
  • 2 Baths
  • 1,371 Sq Ft
  • Built 1999

  1318 Daniels Cove Dr, Winter Garden, FL 34787

  Last Sold Summary

  • 18 Days On Market
• 

  

  /62

  $444,000

  $21K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,725 Sq Ft

  8113 Red Stopper Ln, Winter Garden, FL 34787

  Perfectly positioned in the heart of Horizon West, this impeccably maintained 3-bedroom, 2.5-bath townhome in the highly sought-after Summerlake community offers the rare blend of style, efficiency, and everyday magic — including a two car garage with an attached oversized patio to enjoy nightly views of the Disney fireworks. Move-in ready and thoughtfully upgraded with a newer HVAC system, this

  

  Kassandra Lopez

  EXP REALTY LLC

  (321) 475-7518

  8113 Red Stopper Ln, Winter Garden, FL 34787
• 

  /2

  $2,895 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,760 Sq Ft
  • Townhouse for Rent

  14095 Lochend Way, Winter Garden, FL 34787

  Property Id: 2574642Welcome to your new home at 14095 Lochend Way in Winter Garden, FL! This stunning property offers a wide range of amenities including a dishwasher, washer/dryer, private courtyard, garage, fitness center, swimming pool, and more. Pets are welcome, and utilities are included. Don't miss out on this beautiful rental opportunity for $2850.00/month. Contact us today!

  (561) 609-1455

  14095 Lochend Way, Winter Garden, FL 34787
• 

  /2

  $772,500

  Sold Feb 02, 2026

  15485 Sandfield Loop, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 4,010 Sq Ft
  • Built 2015

  Last Sold Summary

  • 3% Below List Price
  • $193/SF
  • 53 Days On Market

  Current Estimated Value $776,543

  Last Listing Agent Angel Iglesia LUXE PROPERTIES

  15485 Sandfield Loop, Winter Garden, FL 34787
• 

  /2

  Est $808,272

  Not Listed For Sale

  14315 Hampshire Bay Cir, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,332 Sq Ft
  • Built 2004

  14315 Hampshire Bay Cir, Winter Garden, FL 34787

  Last Sold Summary

  • 3 Days On Market
• 

  

  /40

  $289,500

  $31K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,396 Sq Ft

  14501 Grove Resort Ave Unit 2334, Winter Garden, FL 34787

  Escape to your own luxurious, fully furnished condo-hotel residence at the prestigious Grove Resort & Water Park—just minutes from Walt Disney World. Designed for both personal enjoyment and investment, this exceptional unit offers the perfect combination of a turnkey vacation retreat and high-performing income asset. Located on the third floor of Condominium II, the sought-after Jasmine floor

  

  Amy Moline

  EXP REALTY LLC

  (321) 343-3008

  14501 Grove Resort Ave Unit 2334, Winter Garden, FL 34787
• 

  

  /20

  $2,605

  Total Monthly Price

  • 3 Beds
  • 2.5 Baths
  • 1,852 Sq Ft
  • House for Rent

  1907 Seatonham St, Winter Garden, FL 34787

  Now offering 22-month leases. Sign today and lock in today’s low rate for the next 22 months! Offer valid for new applicants who sign a 22-month lease by June 30th, 2026. Base rent will remain at the 12-month lease rate for the duration of the 22-month term. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This property is

  (689) 888-7064

  1907 Seatonham St, Winter Garden, FL 34787
• 

  /2

  $1,070,000

  Sold Dec 05, 2025

  14400 Shocklach Dr, Winter Garden, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 3,616 Sq Ft
  • Built 2015

  Last Sold Summary

  • 5% Below List Price
  • $296/SF
  • 67 Days On Market

  Current Estimated Value $1,051,207

  Last Listing Agent Mauricio Penha VOLKE REAL ESTATE LLC

  14400 Shocklach Dr, Winter Garden, FL 34787
• 

  /2

  Est $456,272

  Not Listed For Sale

  6821 Cultivation Way, Winter Garden, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 2005

  6821 Cultivation Way, Winter Garden, FL 34787

  Last Sold Summary

  • 18 Days On Market
• 

  

  /75

  $795,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,020 Sq Ft

  15239 Lake Lamonia St, Winter Garden, FL 34787

  Under contract-accepting backup offers. Your dream of homeownership starts here! Nestled in a sought-after community zoned for top-rated schools, this stunning 4-bedroom, 3-bathroom single-family home offers 3,020 square feet of beautifully designed living space — and it checks every box on your wish list.From the moment you step inside, you'll be captivated by the bright, open floor plan

  

  Kassandra Lopez

  EXP REALTY LLC

  (321) 333-4471

  15239 Lake Lamonia St, Winter Garden, FL 34787
• 

  

  /20

  $2,842

  Total Monthly Price

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

  14200 Avalon Rd Unit SI ID1244738P, Winter Garden, FL 34787

  The advertised rate of $2,842/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 5, 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

  (689) 263-6852

  14200 Avalon Rd Unit SI ID1244738P, Winter Garden, FL 34787
• 

  /2

  $555,960

  Sold Sep 19, 2025

  13520 Autumn Harvest Ave, Winter Garden, FL 34787

  • 3 Beds
  • 3 Baths
  • 2,198 Sq Ft
  • Built 2025

  Last Sold Summary

  • $253/SF

  Current Estimated Value $554,662

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  13520 Autumn Harvest Ave, Winter Garden, FL 34787
• 

  /2

  Est $569,077

  Not Listed For Sale

  1624 Malcolm Point Dr, Winter Garden, FL 34787

  • 3 Beds
  • 2 Baths
  • 2,035 Sq Ft
  • Built 2002

  1624 Malcolm Point Dr, Winter Garden, FL 34787

  Last Sold Summary

  • 30 Days On Market
• 

  

  /71

  $350,000

  • 3 Beds
  • 2.5 Baths
  • 1,684 Sq Ft

  1437 Scarlet Oak Loop, Winter Garden, FL 34787

  Don't miss this opportunity to own a well-maintained townhome in the sought-after gated community of Tucker Oaks. Featuring 3 bedrooms, 2.5 bathrooms, a 2-car garage, this home offers the perfect blend of comfort, convenience, and value. The open floor plan provides spacious living and dining areas, ideal for both everyday living and entertaining. A major recent improvement includes a roof

  

  Amy Moline

  EXP REALTY LLC

  (689) 329-1772

  1437 Scarlet Oak Loop, Winter Garden, FL 34787
• 

  

  /17

  $2,810

  Total Monthly Price

  • 4 Beds
  • 2 Baths
  • 1,748 Sq Ft
  • House for Rent

  147 Timbercreek Pines Cir, Winter Garden, FL 34787

  Now offering 22-month leases. Sign today and lock in today’s low rate for the next 22 months! Offer valid for new applicants who sign a 22-month lease by June 30th, 2026. Base rent will remain at the 12-month lease rate for the duration of the 22-month term. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This property is

  (689) 407-6113

  147 Timbercreek Pines Cir, Winter Garden, FL 34787
• 

  /2

  $750,000

  Sold May 21, 2026

  13001 Harvest Rain Ave, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,858 Sq Ft
  • Built 2026

  Last Sold Summary

  • $262/SF
  • 14 Days On Market

  Last Listing Agent Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC

  13001 Harvest Rain Ave, Winter Garden, FL 34787
• 

  /2

  Est $780,595

  Not Listed For Sale

  14027 Fairway Willow Ln, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,783 Sq Ft
  • Built 2006

  14027 Fairway Willow Ln, Winter Garden, FL 34787

  Last Sold Summary

  • 32 Days On Market
• 

  

  /40

  $359,900

  $20K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 1,590 Sq Ft

  13705 Golden Russet Dr, Winter Garden, FL 34787

  Under contract-accepting backup offers. Welcome to The Orchard, a tidy gated community of townhomes in sought-after Winter Garden. This residence blends modern comfort with low-maintenance living, offering a bright, open layout that feels inviting from the moment you step inside. Thoughtful upgrades elevate every space—stylish flooring, fresh finishes, and a contemporary color palette create a

  

  Drew Ross

  LAKEFIELD REALTY GROUP LLC

  (321) 399-2408

  13705 Golden Russet Dr, Winter Garden, FL 34787
• 

  

  /20

  $3,230

  Total Monthly Price

  • 5 Beds
  • 3.5 Baths
  • 3,059 Sq Ft
  • House for Rent

  1869 Americus Minor Dr, Winter Garden, FL 34787

  Now offering 22-month leases. Sign today and lock in today’s low rate for the next 22 months! Offer valid for new applicants who sign a 22-month lease by June 30th, 2026. Base rent will remain at the 12-month lease rate for the duration of the 22-month term. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This property is

  (321) 497-0462

  1869 Americus Minor Dr, Winter Garden, FL 34787
• 

  /2

  $594,948

  Sold Nov 18, 2025

  12749 Harvest Rain Ave, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,441 Sq Ft
  • Built 2025

  Last Sold Summary

  • $244/SF

  Current Estimated Value $603,000

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  12749 Harvest Rain Ave, Winter Garden, FL 34787
• 

  /2

  Est $642,777

  Not Listed For Sale

  14661 Old Thicket Trace, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,717 Sq Ft
  • Built 2007

  14661 Old Thicket Trace, Winter Garden, FL 34787

  Last Sold Summary

  • 7 Days On Market
• 

  

  /36

  $270,000

  • 3 Beds
  • 3 Baths
  • 1,544 Sq Ft

  14501 Grove Resort Ave Unit 2527, Winter Garden, FL 34787

  Short Sale. Short Sale Opportunity – Fully Furnished 3BR/3BA Condo at The Grove Resort – Vacation Rental Only / No Full-Time ResidencyInvestor Alert! Rare opportunity to own a FULLY FURNISHED and equipped 3-bedroom, 3-bath condo in the sought-after The Grove Resort, one of Orlando’s top vacation-only condo-hotel communities, just minutes from Disney. Turnkey for immediate rental. Large

  

  Nayane Seabra

  WRA BUSINESS & REAL ESTATE

  (321) 341-5486

  14501 Grove Resort Ave Unit 2527, Winter Garden, FL 34787
• 

  

  /20

  $6,046

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • Condo for Rent

  1223 E Plant St Unit SI ID1526934P, Winter Garden, FL 34787

  The advertised rate of $6,046/month is the lowest available price, based on a 30 day(s) stay with a move-in date of July 2, 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

  (321) 306-0643

  1223 E Plant St Unit SI ID1526934P, Winter Garden, FL 34787
• 

  /2

  $645,000

  Sold Sep 11, 2025

  14664 Spotted Sandpiper Blvd, Winter Garden, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,701 Sq Ft
  • Built 2014

  Last Sold Summary

  • 3% Below List Price
  • $239/SF
  • 0 Days On Market

  Current Estimated Value $647,362

  Last Listing Agent Andreia Beraldo TALENT REALTY SOLUTIONS

  14664 Spotted Sandpiper Blvd, Winter Garden, FL 34787
• 

  /2

  Est $487,716

  Not Listed For Sale

  1156 Brandy Lake View Cir, Winter Garden, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,921 Sq Ft
  • Built 2000

  1156 Brandy Lake View Cir, Winter Garden, FL 34787

  Last Sold Summary

  • 23 Days On Market

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