37,759

Winter Garden, FL Homes

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  • /31

    $735,000

    $5K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 2,878 Sq Ft

    14345 Wabasso Loop, Winter Garden, FL 34787

    Located within the gated community of Tilden Place, this thoughtfully designed home offers exceptional flexibility and everyday comfort in one of Winter Garden’s most convenient locations. The main level features a private primary suite along with three additional bedrooms, including an en suite option ideal for guests, multigenerational living, or a home office. Upstairs, a spacious loft,

    Agent Photo

    Hilary Hall

    COMPASS FLORIDA LLC

    (321) 461-2856

    14345 Wabasso Loop, Winter Garden, FL 34787
  • /14

    $2,755 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,959 Sq Ft
    • House for Rent

    221 Timbercreek Pines Cir, Winter Garden, FL 34787

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve

    (689) 407-8502

    221 Timbercreek Pines Cir, Winter Garden, FL 34787
  • /27

    $659,420

    Sold Oct 31, 2025

    12595 Grape Chardonnay Aly, Winter Garden, FL 34787

    • 4 Beds
    • 3.5 Baths
    • 2,693 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $245/SF
    • 9 Days On Market

    K. Hovnanian Homes Osprey Ranch

    12595 Grape Chardonnay Aly, Winter Garden, FL 34787
    • /2

      Est $612,294

      Not Listed For Sale

      1827 Lindzlu St, Winter Garden, FL 34787

      • 5 Beds
      • 4.5 Baths
      • 2,840 Sq Ft
      • Built 2005
      1827 Lindzlu St, Winter Garden, FL 34787

      Last Sold Summary

      • 59 Days On Market

  • /36

    $434,900

    $55K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 1,626 Sq Ft

    16413 Prairie School Dr, Winter Garden, FL 34787

    Under contract-accepting backup offers. Built in 2021 and located in the desirable Hawksmoor community in Horizon West, this three bedroom, two and a half bath townhome offers a modern layout with thoughtful upgrades throughout. The open concept main living area flows seamlessly into a stylish kitchen featuring quartz countertops and contemporary finishes, while upgraded interior details and

    Agent Photo

    Rob Aponte

    REAL BROKER, LLC

    (321) 284-2245

    16413 Prairie School Dr, Winter Garden, FL 34787
  • /20

    $3,200 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,801 Sq Ft
    • House for Rent

    16007 Micelli Dr, Winter Garden, FL 34787

    Property Id: 2595501Welcome to this beautiful newer construction single-family home in the desirable Winding Bay community of Winter Garden. This spacious two-story residence features 4 bedrooms, 3.5 bathrooms, and a 2-car attached garage. The open-concept layout offers a modern kitchen connected to the family and dining areas, ideal for everyday living and entertaining. A private

    (321) 379-6873

    16007 Micelli Dr, Winter Garden, FL 34787
  • /2

    $575,000

    Sold Dec 12, 2025

    14700 Spotted Sandpiper Blvd, Winter Garden, FL 34787

    • 3 Beds
    • 2 Baths
    • 2,340 Sq Ft
    • Built 2014

    Last Sold Summary

    • $246/SF
    • 5 Days On Market

    Current Estimated Value $576,129

    Last Listing Agent Eve Metlis WATSON REALTY CORP

    14700 Spotted Sandpiper Blvd, Winter Garden, FL 34787
    • /2

      Est $501,596

      Not Listed For Sale

      427 N Lakeview Ave, Winter Garden, FL 34787

      • 4 Beds
      • 2 Baths
      • 1,781 Sq Ft
      • Built 1964
      427 N Lakeview Ave, Winter Garden, FL 34787

      Last Sold Summary

      • 71 Days On Market

  • /82

    $4,900,000

    • 5 Beds
    • 7 Baths
    • 5,564 Sq Ft

    7827 Skiing Way, Winter Garden, FL 34787

    Nestled along the southern shoreline of Lake Hancock amidst an enclave of custom-built lakefront homes, within the private gates ofthe exclusive Isles of Lake Hancock, this newly remodeled masterpiece offers the finest materials and craftsmanship and is ideally situated on 110’ of pristine shoreline frontage with the lake’s most expansive water views. The entryway involves monumental scale

    Agent Photo

    Drew Ross

    LAKEFIELD REALTY GROUP LLC

    (321) 351-4687

    7827 Skiing Way, Winter Garden, FL 34787
  • /13

    $1,550 Per Month

    • 2 Beds
    • 2 Baths
    • 918 Sq Ft
    • Condo for Rent

    126 Windtree Ln, Winter Garden, FL 34787

    Property Id: 424660Remodeled Condo in the heart of Winter Garden just minutes to the quaint, downtown area or the Winter Garden Villages. This condo is perfectly situated in a peaceful setting with a gorgeous view! The gentle color palette will suite every renters design. Split bedroom floorplan. Master suite with walk-in closet and private bath Brand new Stainless Steel Appliances,

    (516) 518-5937

    126 Windtree Ln, Winter Garden, FL 34787
  • /2

    $1,650,000

    Sold Mar 12, 2026

    9 E Newell St, Winter Garden, FL 34787

    • 4 Beds
    • 4.5 Baths
    • 3,686 Sq Ft
    • Built 2025

    Last Sold Summary

    • $448/SF
    • 11 Days On Market

    Current Estimated Value $1,529,784

    Last Listing Agent Alexis Anderson REGENCY REAL ESTATE LLC

    9 E Newell St, Winter Garden, FL 34787
    • /2

      Est $280,182

      Not Listed For Sale

      1181 Partlow Dr, Winter Garden, FL 34787

      • 4 Beds
      • 2 Baths
      • 1,235 Sq Ft
      • Built 1959
      1181 Partlow Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 3 Days On Market

  • /37

    $215,000

    $135K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,396 Sq Ft

    14501 Grove Resort Ave Unit 2438, Winter Garden, FL 34787

    AGENTS - PLEASE VIEW REALTOR REMARKS IN THE MLS. Perfect as a family getaway or a high-performing investment property, this beautifully designed fully furnished 3-bedroom, 2-bath condo is located in the luxurious Grove Resort & Water Park in Winter Garden, FL. Thoughtfully outfitted with every comfort, this turn-key home welcomes you with style and convenience. Enjoy resort-style living with

    Agent Photo

    Rick Brown

    KELLER WILLIAMS ADVANTAGE 2 REALTY

    (321) 382-2706

    14501 Grove Resort Ave Unit 2438, Winter Garden, FL 34787
  • /20

    $2,549 Per Month

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

    10509 Spring Arbor Ln, Winter Garden, FL 34787

    Welcome to 10509 Spring Arbor Ln! This beautifully crafted home in Winter Garden features 3 bedrooms and 2.5 bathrooms, offering a generous living area of 1881 square feet. Step inside to find a cozy living room filled with natural light from large windows, then proceed down the hallway to discover a stunning open kitchen complete with a spacious island, stylish light fixtures that bring a modern

    (321) 257-9157

    10509 Spring Arbor Ln, Winter Garden, FL 34787
  • /25

    $459,990

    Sold Sep 03, 2025

    9404 Bolshoi Aly, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 1,833 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $251/SF
    • 12 Days On Market

    Current Estimated Value $454,770

    9404 Bolshoi Aly, Winter Garden, FL 34787
    • /2

      Est $491,320

      Not Listed For Sale

      16837 Arrowhead Blvd, Winter Garden, FL 34787

      • 3 Beds
      • 2 Baths
      • 1,299 Sq Ft
      • Built 2002
      16837 Arrowhead Blvd, Winter Garden, FL 34787

      Last Sold Summary

      • 522 Days On Market

  • /59

    $939,000

    Pending
    • 4 Beds
    • 4 Baths
    • 2,881 Sq Ft

    14354 Wabasso Loop, Winter Garden, FL 34787

    Welcome to this beautifully maintained Scandinavian-inspired home built in 2022, located in an intimate gated boutique community of just 55 homes in Winter Garden. Perfectly positioned on the premier lot in the neighborhood with a direct fountain water view, this home offers breathtaking sunsets from the living room, kitchen, lanai, pool, and balcony—while enjoying sun-filled interiors throughout

    Agent Photo

    Daniel Robinson

    HOUWZER INC

    (321) 373-7260

    14354 Wabasso Loop, Winter Garden, FL 34787
  • /20

    $4,846

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • Condo for Rent

    1223 E Plant St Unit SI FL3-ID1511054P, Winter Garden, FL 34787

    The advertised rate of $4,846/month is the lowest available price, based on a 30 day(s) stay with a move-in date of July 25, 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) 599-4185

    1223 E Plant St Unit SI FL3-ID1511054P, Winter Garden, FL 34787
  • /2

    $415,000

    Sold Jan 12, 2026

    8105 Red Stopper Ln, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 1,725 Sq Ft
    • Built 2017

    Last Sold Summary

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

    Current Estimated Value $417,605

    Last Listing Agent Heather Carr, PA BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

    8105 Red Stopper Ln, Winter Garden, FL 34787
    • /2

      Est $848,222

      Not Listed For Sale

      1215 Castleport Rd, Winter Garden, FL 34787

      • 4 Beds
      • 3 Baths
      • 3,864 Sq Ft
      • Built 2001
      1215 Castleport Rd, Winter Garden, FL 34787

      Last Sold Summary

      • 72 Days On Market

  • /26

    $1,299,000

    $1M PRICE DROP
    • Land
    • 5.11 Acres
    • $254,207 per Acre

    10133 Colt Ln, Winter Garden, FL 34787

    Discover 5.1 beautiful acres in Avalon Hills, an exclusive community featuring just 16 premium luxury home 5 acre lots. No need to move almost an hour away just to find some land and more privacy when this gem is minutes to Windermere and everywhere you want to be. This vacant land represents the essence of premium real estate, nestled at the end of a one-way street ending in a serene cul-de-sac

    Agent Photo

    Jessica McKinney

    FLORIDA REALTY EXCHANGE LLC

    (321) 386-1622

    10133 Colt Ln, Winter Garden, FL 34787
  • /18

    $2,895 Per Month

    • 5 Beds
    • 2.5 Baths
    • 2,220 Sq Ft
    • House for Rent

    1848 Sherbourne St, 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 $3039.90. That covers your base rent, $2895.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    (321) 382-4648

    1848 Sherbourne St, Winter Garden, FL 34787
  • /2

    $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 $539,512

    Last Listing Agent Silvia Kinkela SERHANT

    14342 White Moss Way, Winter Garden, FL 34787
    • /2

      Est $947,426

      Not Listed For Sale

      922 Home Grove Dr, Winter Garden, FL 34787

      • 4 Beds
      • 4 Baths
      • 3,826 Sq Ft
      • Built 2006
      922 Home Grove Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 11 Days On Market

  • /37

    $495,000

    • 2 Beds
    • 2 Baths
    • 1,574 Sq Ft

    15806 Gem View St, Winter Garden, FL 34787

    Built in 2024, this like-new home is located on a premium cul-de-sac lot within a sought-after community in Winter Garden. Offering exceptional privacy with no rear neighbors, the backyard provides a peaceful setting to relax and enjoy Florida's outdoor lifestyle. The community is designated as 55+; however, buyers of 25 years old are permitted to purchase within the community. This beautifully

    Agent Photo

    Yanely Fernandez

    Fast Action Realty Inc

    (321) 252-6162

    15806 Gem View St, Winter Garden, FL 34787
  • /17

    $3,025 Per Month

    • 4 Beds
    • 3 Baths
    • 2,179 Sq Ft
    • House for Rent

    914 Copenhagen Way, Winter Garden, FL 34787

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve

    (321) 510-9133

    914 Copenhagen Way, Winter Garden, FL 34787
  • /2

    $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 $575,024

    Last Listing Agent Diana Basch Connery MS LAND & BUILDING LLC

    15249 Purple Martin St, Winter Garden, FL 34787
    • /2

      Est $819,946

      Not Listed For Sale

      2151 Tillman Ave, Winter Garden, FL 34787

      • 5 Beds
      • 4 Baths
      • 3,506 Sq Ft
      • Built 2007
      2151 Tillman Ave, Winter Garden, FL 34787

      Last Sold Summary

      • 41 Days On Market

  • /25

    $332,500

    $37K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,265 Sq Ft

    14501 Grove Resort Ave Unit 3205, Winter Garden, FL 34787

    Luxury vacation rental within The Grove Resort and Spa. Beautifully furnished with modern furniture and fixtures that make for a one-of-a-kind vacation property, this fully furnished 2-bedroom, 2-bath unit can sleep up to 8 people (room with1 king bed, room with 2 full beds and queen sleeper sofa) and has a gourmet kitchen with stainless steel appliances and quartz counters. The Grove Resort and

    Agent Photo

    Jamie Ampel

    ALL SELLERS & BUYERS REALTY INC

    (321) 710-1042

    14501 Grove Resort Ave Unit 3205, Winter Garden, FL 34787
  • /10

    $3,445 Per Month

    • 4 Beds
    • 3 Baths
    • 2,846 Sq Ft
    • House for Rent

    934 Home Grove 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 $3589.90. That covers your base rent, $3445.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    (321) 517-2882

    934 Home Grove Dr, Winter Garden, FL 34787
  • /2

    $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 $1,685,061

    Last Listing Agent Ronald Ziolkowski RE/MAX PRIME PROPERTIES

    9072 Bradleigh Dr, Winter Garden, FL 34787
    • /2

      Est $503,729

      Not Listed For Sale

      1133 Brandy Lake View Cir, Winter Garden, FL 34787

      • 4 Beds
      • 2 Baths
      • 1,686 Sq Ft
      • Built 1998
      1133 Brandy Lake View Cir, Winter Garden, FL 34787

      Last Sold Summary

      • 7 Days On Market

  • /30

    $499,000

    $23K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,042 Sq Ft

    16105 Water Spring Blvd, Winter Garden, FL 34787

    PRICE IMPROVEMENT!!! Now offered at a substantially reduced price. The seller will pay off the existing solar panel loan (approximately $29,000) in full at closing, allowing the buyer to enjoy the benefits of solar energy without assuming this debt.Perfect for buyers seeking convenience, accessibility, and a family-friendly setting—just steps from the elementary school!!Discover this

    Agent Photo

    Yesenia Barrios

    URBAN-O REAL ESTATE SOLUTIONS

    (321) 321-8146

    16105 Water Spring Blvd, Winter Garden, FL 34787
  • /2

    $2,749 Per Month

    • 4 Beds
    • 2 Baths
    • 1,606 Sq Ft
    • House for Rent

    1708 Portcastle Cir, Winter Garden, FL 34787

    Coming soon - this home is currently being enjoyed by another resident but will be available soon. This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.5 bathrooms, and approximately 1,606 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a

    (321) 515-5399

    1708 Portcastle Cir, Winter Garden, FL 34787
  • /2

    $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 $398,120

    Last Listing Agent Erica Diaz HOMEVEST REALTY

    15574 Murcott Blossom Blvd, Winter Garden, FL 34787
    • /2

      Est $291,206

      Not Listed For Sale

      608 S Lakeview Ave, Winter Garden, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 1,566 Sq Ft
      • Built 1957
      608 S Lakeview Ave, Winter Garden, FL 34787

      Last Sold Summary

      • 86 Days On Market

  • /68

    $1,700,000

    $400K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 4,365 Sq Ft

    2450 Dahlgren Way, Winter Garden, FL 34787

    Rare Gated Lakefront Retreat with Grandfathered Boat Access on Lake Luntz Discover resort-style living in this one-of-a-kind gated lakefront home in the heart of Winter Garden. Nestled on a quiet, tree-lined cul-de-sac, this 5-bedroom, 5-bathroom, 4,365 Sq Ft home offers a smart layout designed for both everyday living and entertaining. The first-floor bedroom and full bath are ideal for guests

    Agent Photo

    Keegan Siegfried

    LPT REALTY, LLC

    (321) 252-6500

    2450 Dahlgren Way, Winter Garden, FL 34787
  • /16

    $2,610 Per Month

    • 4 Beds
    • 2 Baths
    • 1,692 Sq Ft
    • House for Rent

    266 Regal Downs Cir, Winter Garden, FL 34787

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve

    (689) 407-2766

    266 Regal Downs Cir, Winter Garden, FL 34787
  • /2

    $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 $1,665,553

    Last Listing Agent Erica Diaz HOMEVEST REALTY

    557 Lake Cove Pointe Cir, Winter Garden, FL 34787
    • /28

      Est $426,998

      Not Listed For Sale

      6067 Blue Lily Way, Winter Garden, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 1,560 Sq Ft
      • Built 2021
      6067 Blue Lily Way, Winter Garden, FL 34787

      Last Sold Summary

      • 58 Days On Market

Showing Results 161 - 200, Page 5 of 18

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