Winter Garden, FL Homes

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  /71

  $645,900

  New Construction

  • 3 - 4 Beds
  • 2.5 - 3.5 Baths
  • 2,120+ Sq Ft

  Hemingway Plan at Northlake at Ovation, Winter Garden, FL 34787

  New Single-Story Home by RockWell Homes, Now Selling! Introducing a beautifully designed, new single-story home perfect for modern living. This home offers 3 -4 spacious bedrooms, 2.5-3 bathrooms, and a functional layout with a dining area, breakfast nook,home office area and a 2-car garage. The inviting exterior includes a covered front porch and a covered backyard lanai, with multiple upscale

  RockWell Homes Builder

  17551 Lake Star Rd Unit 36901616, Winter Garden, FL 34787
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  /30

  $3,150 Per Month

  • 3 Beds
  • 3.5 Baths
  • 2,072 Sq Ft
  • Townhouse for Rent

  15489 Hamlin Park Dr, Winter Garden, FL 34787

  Don’t miss the chance to call this BRAND-NEW luxury townhome in Parkview at Hamlin your home! This Haines II, stunning 3-bedroom, 2.5-bathroom, 3-story townhome in the highly desirable Parkview at Hamlin community of Winter Garden was just completed and never lived in. Inside, you’ll find a thoughtfully designed floor plan with three private suites, including a first-floor guest suite and a

  Shane Jordan COLDWELL BANKER REALTY

  15489 Hamlin Park Dr, Winter Garden, FL 34787
• 

  

  /2

  $613,160

  Sold May 19, 2026

  6309 Wild Persimmon Way, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,515 Sq Ft
  • Built 2026

  Last Sold Summary

  • 14% Below List Price
  • $244/SF
  • 0 Days On Market

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  6309 Wild Persimmon Way, Winter Garden, FL 34787
• 

  

  /2

  Est $688,581

  Not Listed For Sale

  14891 Winter Stay Dr, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,662 Sq Ft
  • Built 2018

  14891 Winter Stay Dr, Winter Garden, FL 34787

  Last Sold Summary

  • 128 Days On Market
• 

  

  

  /49

  $695,000

  $24K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,839 Sq Ft

  5966 Cypress Hill Rd, Winter Garden, FL 34787

  Price Improvement – Welcome to 5966 Cypress Hill Rd, located in the highly sought-after Independence community of Winter Garden. This well-maintained home offers a rare blend of privacy, space, and lifestyle amenities. Situated on a larger-than-average lot with no rear neighbors, the home backs up to an open area, creating a peaceful and private setting—perfect for relaxing or entertaining.

  Mahmoud Mango DALTON WADE INC

  5966 Cypress Hill Rd, Winter Garden, FL 34787
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  /24

  $2,850 Per Month

  • 3 Beds
  • 2 Baths
  • 1,755 Sq Ft
  • House for Rent

  10672 Words Dr, Winter Garden, FL 34787

  Welcome home in the master planned community of Storey Grove! Minutes from Downtown WINTER GARDEN, this stunning 3-Bedroom, 2 1/2 Bath, 2 car garage Townhome property is situated just minutes from world class theme parks and attractions. Enjoying local restaurants and shopping just a short drive away. Love the outdoors? Slow down the pace and explore nearby parks and farmer's markets. Your

  10672 Words Dr, Winter Garden, FL 34787
• 

  /2

  $345,000

  Sold Mar 25, 2026

  282 E Newell St, Winter Garden, FL 34787

  • Land
  • 7,840 Sq Ft
  • $1,916,667 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 195 Days On Market

  Current Estimated Value $366,170

  Last Listing Agent Karen Jacobs COLDWELL BANKER REALTY

  282 E Newell St, Winter Garden, FL 34787
• 

  

  /31

  Est $848,371

  Not Listed For Sale

  876 Landrum Dr, Winter Garden, FL 34787

  • 3 Beds
  • 3.5 Baths
  • 2,485 Sq Ft
  • Built 2014

  876 Landrum Dr, Winter Garden, FL 34787

  Last Sold Summary

  • 26 Days On Market
• 

  

  /8

  $438,990

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,635 Sq Ft

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

  The Regina 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 inviting space for everyday living. Upstairs, the private primary suite features a walk-in closet, accompanied by two additional bedrooms and a conveniently located laundry

  Ashton Woods Builder

  17551 Lake Star Rd Unit 36453066, Winter Garden, FL 34787
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  /36

  $3,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft
  • House for Rent

  17739 Sharp Pummelo Aly, Winter Garden, FL 34787

  Welcome to this beautiful, nearly new home located in the desirable Northlake at Ovation community in Winter Garden! Built in 2025, this well-maintained single-story home features 3 bedrooms, 2 bathrooms, and 1,788 sq. ft. of comfortable living space. The open-concept layout offers a bright and inviting living area, a modern kitchen, and spacious bedrooms designed for everyday comfort.

  Naiara Alves MS LAND & BUILDING LLC

  17739 Sharp Pummelo Aly, Winter Garden, FL 34787
• 

  /2

  $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 $439,872

  Last Listing Agent Stacie Brown Kelly KELLER WILLIAMS ADVANTAGE REALTY

  15451 Bay Bridge St, Winter Garden, FL 34787
• 

  /2

  Est $534,253

  Not Listed For Sale

  15162 Book Club Rd, Winter Garden, FL 34787

  • 3 Beds
  • 2 Baths
  • 2,089 Sq Ft
  • Built 2019

  15162 Book Club Rd, Winter Garden, FL 34787

  Last Sold Summary

  • 202 Days On Market
• 

  

  /37

  $782,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,291 Sq Ft

  Tidewater With Bonus Plan at Avalon Woods - 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 Avalon Woods St Unit 37162284, Winter Garden, FL
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  /40

  $3,325 Per Month

  • 4 Beds
  • 3 Baths
  • 2,083 Sq Ft
  • House for Rent

  16705 Victoria Grv Aly, Winter Garden, FL 34787

  Welcome to 16705 Victoria Grove Aly, a beautifully designed 4-bedroom, 3-bathroom home located in the highly sought-after community of Winter Garden, FL. This modern two-story home features an open-concept floor plan with a spacious great room, contemporary kitchen with stainless steel appliances, and a versatile upstairs loft perfect for a home office or media space. The primary suite

  16705 Victoria Grv Aly, Winter Garden, FL 34787
• 

  /2

  $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 $550,551

  Last Listing Agent Gilbert Ramos EXP REALTY LLC

  660 Egret Place Dr, Winter Garden, FL 34787
• 

  /2

  Est $801,576

  Not Listed For Sale

  15870 Citrus Grove Loop, Winter Garden, FL 34787

  • 4 Beds
  • 4 Baths
  • 3,074 Sq Ft
  • Built 2015

  15870 Citrus Grove Loop, Winter Garden, FL 34787

  Last Sold Summary

  • 92 Days On Market
• 

  

  /79

  $735,900

  New Construction

  • 4 Beds
  • 2.5 - 3.5 Baths
  • 2,889+ Sq Ft

  Eliot Plan at Northlake at Ovation, Winter Garden, FL 34787

  Luxurious New Home by RockWell Homes, Now Selling! Welcome to the Eliot design, a thoughtfully crafted home offering a balance of comfort, style, and flexibility. This popular floorplan includes 4 bedrooms, 2.5 to 3.5 bathrooms, and a spacious loft, with multiple structural options available to personalize the layout. The exterior design enhances curb appeal and functionality, featuring a covered

  RockWell Homes Builder

  17551 Lake Star Rd Unit 36901640, Winter Garden, FL 34787
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  /50

  $3,850 Per Month

  • 5 Beds
  • 3 Baths
  • 3,747 Sq Ft
  • House for Rent

  2205 Wintermere Pointe Dr, Winter Garden, FL 34787

  Available for a one-year lease at $3,850/month, this two-story, 5/3 home with a private screened pool sits in the gated Wintermere Pointe community of Winter Garden. The layout offers a downstairs bedroom plus four bedrooms up, an open family room with sliding doors to the covered lanai and pavered pool deck, formal living and dining rooms, and two upstairs loft spaces. Residents are minutes from

  Kevin Escribano GLOBAL KEY REALTY, LLC

  2205 Wintermere Pointe Dr, Winter Garden, FL 34787
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  /2

  $510,000

  Sold Jan 05, 2026

  12259 Bracco St, Winter Garden, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,082 Sq Ft
  • Built 2024

  Last Sold Summary

  • 11% Below List Price
  • $245/SF
  • 176 Days On Market

  Current Estimated Value $511,192

  Last Listing Agent Khadija Webber EPIQUE REALTY INC.

  12259 Bracco St, Winter Garden, FL 34787
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  /47

  Est $922,994

  Not Listed For Sale

  14843 Winter Stay Dr, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,505 Sq Ft
  • Built 2018

  14843 Winter Stay Dr, Winter Garden, FL 34787

  Last Sold Summary

  • 22 Days On Market
• 

  

  /3

  $651,990

  New Construction

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

  Anna Maria Plan at Avalon Woods - 50' Homesites, Winter Garden, FL

  The Anna Maria floorplan is a thoughtfully designed one-story home featuring four bedrooms and two and a half bathrooms, perfect for comfortable family living. The open-concept layout highlights a spacious great room that flows seamlessly into the kitchen and dining area, making it ideal for gatherings and relaxation. The primary bedroom offers privacy with a well-appointed ensuite and a large

  Dream Finders Homes Builder

  0 Avalon Woods St Unit 37123076, Winter Garden, FL
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  /38

  $2,095 Per Month

  • 3 Beds
  • 3 Baths
  • 1,544 Sq Ft
  • Townhouse for Rent

  1535 Broken Oak Dr, Winter Garden, FL 34787

  ? STUNNING GATED TOWNHOME IN WINTER GARDEN – AVAILABLE NOW! ?Welcome home to this stylish 2-story, 3-bedroom, 2.5-bathroom townhome featuring an attached 2-car garage. Tucked inside the highly desirable, gated community of Tucker Oaks in the heart of Winter Garden, this home offers 1,544 sq. ft. of bright, open living space designed for easy everyday living and effortless

  1535 Broken Oak Dr, Winter Garden, FL 34787
• 

  /2

  $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 $475,485

  11960 Bracco St, Winter Garden, FL 34787
• 

  

  /54

  Est $563,996

  Not Listed For Sale

  14043 Snowy Owl Ln, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,136 Sq Ft
  • Built 2016

  14043 Snowy Owl Ln, Winter Garden, FL 34787

  Last Sold Summary

  • 73 Days On Market
• 

  

  /3

  $617,990

  New Construction

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

  Anna Maria Plan at Hamlin Meadows - 50' Homesites, Winter Garden, FL

  The Anna Maria floorplan is a thoughtfully designed one-story home featuring four bedrooms and two and a half bathrooms, perfect for comfortable family living. The open-concept layout highlights a spacious great room that flows seamlessly into the kitchen and dining area, making it ideal for gatherings and relaxation. The primary bedroom offers privacy with a well-appointed ensuite and a large

  Dream Finders Homes Builder

  0 Hamlin Meadows St Unit 39127934, Winter Garden, FL
• 

  

  /12

  $3,100 Per Month

  • 4 Beds
  • 3.5 Baths
  • 2,072 Sq Ft
  • Townhouse for Rent

  15038 Groveside Rd, Winter Garden, FL 34787

  Experience luxury living in one of Winter Garden's most desirable communities! This stunning 3-story townhome in Parkview at Hamlin offers the perfect blend of comfort, style, and an unbeatable location.Featuring a private first-floor bedroom suite, this home is ideal for guests, extended family, or a private home office. The spacious open-concept main living area showcases a beautiful

  Carolina Robbins KARDOSH REALTY

  15038 Groveside Rd, Winter Garden, FL 34787
• 

  /2

  $1,250,000

  Sold Mar 30, 2026

  14355 Black Lake Preserve St, Winter Garden, FL 34787

  • 6 Beds
  • 5 Baths
  • 5,296 Sq Ft
  • Built 2016

  Last Sold Summary

  • 5% Above List Price
  • $236/SF
  • 3 Days On Market

  Current Estimated Value $1,210,320

  Last Listing Agent Drew Belani COMPASS FLORIDA LLC

  14355 Black Lake Preserve St, Winter Garden, FL 34787
• 

  

  /42

  Est $530,645

  Not Listed For Sale

  5608 Thomas Square Dr, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,990 Sq Ft
  • Built 2018

  5608 Thomas Square Dr, Winter Garden, FL 34787

  Last Sold Summary

  • 20 Days On Market
• 

  

  /13

  $625,990

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,857+ Sq Ft

  Ashford Plan at Lake Star at Ovation - Cottage Collection, Winter Garden, FL 34787

  It's love at first sight when you first see the Ashford! With the inviting front porch, carriage-style garage doors, brick paver driveway and lead walk, this home is reminiscent of a simpler time! This single-story, 3 bedroom, 2 bathroom, 2-car garage home ranges from 1,857 - 1,912 square feet. Schedule your tour today!

  M/I Homes Builder

  12025 Encore at Ovation Way Unit 36487483, Winter Garden, FL 34787
• 

  

  /10

  $5,000 Per Month

  • 5 Beds
  • 4.5 Baths
  • 3,724 Sq Ft
  • House for Rent

  16324 Silver Grv Blvd, Winter Garden, FL 34787

  Welcome to this stunning, nearly new residence in the highly desirable community of Silverleaf Reserve at Hamlin in Winter Garden. Built in 2023, this modern two-story home offers approximately 3,743 sq. ft. of thoughtfully designed living space filled with natural light and seamless indoor–outdoor flow. The flexible layout provides multiple options for a home office, game room, or media

  16324 Silver Grv Blvd, Winter Garden, FL 34787
• 

  

  /39

  $465,990

  Sold Nov 14, 2025

  15429 Hamlin Park Dr, Winter Garden, FL 34787

  • 3 Beds
  • 3.5 Baths
  • 2,072 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $225/SF
  • 44 Days On Market

  Current Estimated Value $491,759

  15429 Hamlin Park Dr, Winter Garden, FL 34787
• 

  /2

  Est $423,845

  Not Listed For Sale

  9513 Amber Chestnut Way, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,789 Sq Ft
  • Built 2018

  9513 Amber Chestnut Way, Winter Garden, FL 34787

  Last Sold Summary

  • 13 Days On Market
• 

  

  /3

  $646,990

  New Construction

  • 3 - 4 Beds
  • 2 - 3 Baths
  • 2,066 Sq Ft

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

  The Douglas II is a one-story home offering three bedrooms, two full bathrooms, and a two-car garage. The open-concept layout connects the kitchen to the great room, creating a spacious and bright central living space. A private primary suite offers comfort and seclusion, while an oversized laundry room and a large, covered lanai enhance everyday functionality and outdoor living. Thoughtful

  Ashton Woods Builder

  17551 Lake Star Rd Unit 36470845, Winter Garden, FL 34787
• 

  

  /100

  $12,950 Per Month

  • 5 Beds
  • 5 Baths
  • 4,038 Sq Ft
  • House for Rent

  16870 Sanctuary Dr, Winter Garden, FL 34787

  Experience elevated lakefront living in one of Winter Garden’s most desirable communities. This fully furnished luxury residence offers a rare combination of design, comfort, and lifestyle, perfectly positioned on a premium lakefront lot with one of the most breathtaking views in the area. Featuring 5 spacious bedrooms and 5 bathrooms, this home was thoughtfully designed with high-end custom

  Lino Cervino FORTUNE GLOBAL REALTY

  16870 Sanctuary Dr, Winter Garden, FL 34787
• 

  /2

  $3,470,000

  Sold Mar 12, 2026

  521 N Pollard St, Winter Garden, FL 34787

  • 5 Beds
  • 5.5 Baths
  • 4,808 Sq Ft
  • Built 2026

  Last Sold Summary

  • 35% Above List Price
  • $722/SF

  Current Estimated Value $907,000

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

  521 N Pollard St, Winter Garden, FL 34787
• 

  /2

  Est $520,769

  Not Listed For Sale

  16137 Azure Key St, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,250 Sq Ft
  • Built 2018

  16137 Azure Key St, Winter Garden, FL 34787

  Last Sold Summary

  • 61 Days On Market
• 

  

  /67

  $620,000

  $10K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,692 Sq Ft

  17059 Harbor Oak Pkwy, Winter Garden, FL 34787

  Motivated Seller! Don't miss your opportunity with this Winter Garden home - offering elegance, convenience and affordability. Situated inside the desirable Waterside community, you will find this beautifully designed residence, blending timeless sophistication with modern comfort, offering an open floor plan, designer finishes, and exceptional indoor-outdoor living.From the moment you

  Wendy Moore ERA GRIZZARD REAL ESTATE

  17059 Harbor Oak Pkwy, Winter Garden, FL 34787
• 

  

  /18

  $2,850 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,186 Sq Ft
  • 3 BEDROOM HOUSE ON INDEPENDENCE - NO REAR NEIGHBORS AVAILABLE 8/14/26

  6303 Point Hancock Dr, Winter Garden, FL 34787

  THREE BEDROOM, 2.5 BATHROOM 2,186 SQ FT. OPEN PLAN KITCHEN WITH GRANITE COUNTER TOPS AND STAINLESS STEEL APPLIANCES. LAUNDRY ROOM, FAMILY ROOM AND DINING AREA COMPLETES THE FIRST FLOOR. ALL THREE BEDROOMS UPSTAIRS, INCLUDING ENSUITE BATHROOM AND FAMILY BATHROOM. LOFT AREA FOR ADDITIONAL LIVING SPACE OR OFFICE++CEILING FANS WILL BE REMOVED BY CURRENT TENANT++COMMUNITY HAS FITNESS

  6303 Point Hancock Dr, Winter Garden, FL 34787
• 

  /2

  $120,000

  Sold Sep 30, 2025

  416 Eron Way Unit 30, Winter Garden, FL 34787

  • 1 Bed
  • 1 Bath
  • 420 Sq Ft
  • Built 1984

  Last Sold Summary

  • 13% Below List Price
  • $286/SF
  • 36 Days On Market

  Current Estimated Value $115,118

  Last Listing Agent David Dorman CENTURY 21 CARIOTI

  416 Eron Way Unit 30, Winter Garden, FL 34787
• 

  

  /72

  Est $784,552

  Not Listed For Sale

  7554 Tangerine Knoll Loop, Winter Garden, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,254 Sq Ft
  • Built 2018

  7554 Tangerine Knoll Loop, Winter Garden, FL 34787

  Last Sold Summary

  • 0 Days On Market

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