Winter Garden, FL 2-Story Homes for Sale

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  $499,999 New Construction

  • 2 - 3 Beds
  • 2.5 - 4.5 Baths
  • 1,992 Sq Ft

  Ashwood Plan at Harvest at Ovation, Winter Garden, FL 34787

  Enter the charming oasis that lies within the Ashwood bungalow floor plan. The 1,992 sq. ft. two-story home with 2 bedrooms, 2.5 bathrooms, and a 2-car detached garage boasts both spacious living areas and the welcoming comfort that you deserve. Just passed the foyer is the capacious great room that is overlooked by the beautifully appointed gourmet kitchen. This space is also complemented by an

  Taylor Morrison Builder

  15069 Summer Harvest St Unit 36664490, Winter Garden, FL 34787
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  $730,999 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,101 Sq Ft

  Cumberland Plan at Harvest at Ovation, Winter Garden, FL 34787

  The Cumberland is a spacious two-story floor plan with 5 bedrooms and 4.5 bathrooms. The foyer flows through to the open-concept living space, which includes a large great room, dining area, and chef-inspired kitchen. The great room overlooks two sliding doors that leads out to the lanai. Tucked away right off the dining area and kitchen is a primary suite with a large primary bathroom with dual

  Taylor Morrison Builder

  15069 Summer Harvest St Unit 36664492, Winter Garden, FL 34787
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  $900,990 New Construction

  • 4 - 6 Beds
  • 3.5 Baths
  • 3,471 Sq Ft

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

  The Michigan is a spacious two-story home offering four bedrooms, three full bathrooms, one half bathroom, and a two-car garage. Designed for both everyday living and entertaining, this plan features a large open-concept kitchen and family room, a private first-floor primary suite, and multiple flexible spaces including a second-floor loft and bonus room. Additional highlights include abundant

  Ashton Woods Builder

  17551 Lake Star Rd Unit 36646290, Winter Garden, FL 34787
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  $559,990 New Construction

  • 3 - 4 Beds
  • 2 Baths
  • 2,200 Sq Ft

  Nicola II Plan at Osprey Ranch - 32'/40' Single Family, Winter Garden, FL 34787

  Optional Extra Suite for multi-generational living. Stunning kitchen overlooking great room and dining area. Spacious great room with access to covered lanai. Laundry room in proximity to bedrooms on second floor. Relaxing primary suite with tray ceiling and walk-in closet. Primary bath with seated shower and dual sinks.

  K. Hovnanian Homes Builder

  15221 Blue Peacock Ln Unit 36454104, Winter Garden, FL 34787
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  $628,990 New Construction

  • 5 Beds
  • 4 Baths
  • 2,866 Sq Ft

  CRESSWELL Plan at Waterleigh, Winter Garden, FL 34787

  Waterleigh presents the Cresswell, available to build in Winter Garden, Florida. This two-story all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you’ll find a flex room perfect for work or play and downstairs powder room. The

  D.R. Horton Builder

  10482 Atwater Bay Dr Unit 36202691, Winter Garden, FL 34787
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  $444,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,567 Sq Ft

  16353 Lakelet Aly, Winter Garden, FL 34787

  "Welcome to your charming townhome located at Waterleigh. The Ibis townhome is where comfort, style, and modern convenience come together to create the perfect haven for you and your family. This delightful residence features 1,567 square feet, three spacious bedrooms, 2 1/2 baths, a convenient one-car garage, ample loft space, and cutting-edge smart home technology. Step inside to discover a

  Stephen Cline DR HORTON REALTY OF CENTRAL FLORIDA LLC

  16353 Lakelet Aly, Winter Garden, FL 34787
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  $1,350,000 New Construction

  • 6 Beds
  • 5 Baths
  • 4,152 Sq Ft

  13217 Tollcross Way, Winter Garden, FL 34787

  *****BRAND NEW HOUSE***** construction 2025! Wonderfull location with beautiful view for the water back and front house. Are more then 4,000 s.f. with 6 beds, 5 baths, office, 2 cars garage, loft, private pool with spa and much more! The designer studio invested $386,000 in upgrades. This home truly has a high standard in terms of finishes. Future amenities in the community include a pool, gym,

  Jose Ricardo Cerqueira JR CERQUEIRA REALTY CORP

  13217 Tollcross Way, Winter Garden, FL 34787
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  $749,000 New Construction

  • 4 Beds
  • 3 Baths
  • 2,924 Sq Ft

  18102 Adrift Rd, Winter Garden, FL 34787

  HUGE PRICE REDUCTION! MOTIVATED SELLER! CONSERVATION & WATER VIEW! No Rear neighbor, This home invites you in from the time you enter! Great for entertaining with the café just off the kitchen for casual dining and includes stainless steel appliances and granite counter tops.The master bedroom is conveniently located on the first floor, with a luxurious master bathroom boasting his/her vanities,

  Yujie Jiang INTOP REALTY LLC

  18102 Adrift Rd, Winter Garden, FL 34787
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  $488,797 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,729 Sq Ft

  17732 Porter Rd, Winter Garden, FL 34787

  The Sage floorplan offers a thoughtfully designed two-story layout, ideal for comfortable living and modern convenience. This 3-bedroom, 2.5-bathroom townhome features an open concept on the first floor, highlighted by a spacious great room, a cozy lanai, and a breezeway that connects to a 2-car garage. Upstairs, the second floor boasts all three bedrooms, along with a versatile loft space,

  Dream Finders Homes Builder

  17732 Porter Rd, Winter Garden, FL 34787
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  $483,542 New Construction

  • 3 Beds
  • 3 Baths
  • 1,715 Sq Ft

  17736 Porter Rd, Winter Garden, FL 34787

  The Porter floorplan is an inviting two-story townhome designed with thoughtful spaces throughout. Featuring three bedrooms and two full bathrooms, the layout offers a smooth flow between living spaces. The first floor boasts a bright great room that opens into the dining area and lanai, perfect for entertaining or relaxation. Upstairs, all three bedrooms are thoughtfully arranged alongside a

  Dream Finders Homes Builder

  17736 Porter Rd, Winter Garden, FL 34787
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  $488,421 New Construction

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

  17740 Porter Rd, Winter Garden, FL 34787

  The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath,

  Dream Finders Homes Builder

  17740 Porter Rd, Winter Garden, FL 34787
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  $480,198 New Construction

  • 3 Beds
  • 3 Baths
  • 1,715 Sq Ft

  17728 Porter Rd, Winter Garden, FL 34787

  The Porter floorplan is an inviting two-story townhome designed with thoughtful spaces throughout. Featuring three bedrooms and two full bathrooms, the layout offers a smooth flow between living spaces. The first floor boasts a bright great room that opens into the dining area and lanai, perfect for entertaining or relaxation. Upstairs, all three bedrooms are thoughtfully arranged alongside a

  Dream Finders Homes Builder

  17728 Porter Rd, Winter Garden, FL 34787
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  $584,610 New Construction

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

  17037 Haggerty Hollow Dr, Winter Garden, FL 34787

  The Carter at Hamlin Meadows: Luxury Living with Unmatched Privacy. Discover the perfect blend of elegance and functionality in the Carter model This impressive 2,515 sq. ft. residence features 4 bedrooms, 3.5 bathrooms, and a rear-load 2-car garage, thoughtfully designed for modern lifestyles. The heart of the home is an expansive open-concept main level, where a 15' x 17' great room flows

  Dream Finders Homes Builder

  17037 Haggerty Hollow Dr, Winter Garden, FL 34787
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  $863,442 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,802 Sq Ft

  5930 Flowering Cherry Bend, Winter Garden, FL 34787

  The Davis Plan by Dream Finders Homes is a spacious two-story residence designed for modern living. Offering approximately 2,802 square feet of living space, this home features four bedrooms and two and a half bathrooms. The open-concept design seamlessly connects the great room, kitchen, and dining area, creating an ideal space for entertaining. The owner's suite serves as a private retreat,

  Dream Finders Homes Builder

  5930 Flowering Cherry Bend, Winter Garden, FL 34787
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  $582,682 New Construction

  • 4 Beds
  • 3 Baths
  • 2,102 Sq Ft

  17055 Haggerty Hollow Dr, Winter Garden, FL 34787

  The Berkley at Hamlin Meadows: Luxury Living with Unmatched Privacy. Discover the perfect blend of elegance and functionality in the Berkley model. This impressive 2,102 sq. ft. residence features 4 bedrooms, 3 bathrooms, and a rear-load 2-car garage, thoughtfully designed for modern lifestyles. The heart of the home is an expansive open-concept main level, where a 15' x 15' great room flows

  Dream Finders Homes Builder

  17055 Haggerty Hollow Dr, Winter Garden, FL 34787
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  $824,390 New Construction

  • 6 Beds
  • 4.5 Baths
  • 3,117 Sq Ft

  17060 Haggerty Hollow Dr, Winter Garden, FL 34787

  Welcome to this beautifully designed six-bedroom, four-bathroom home located in the sought-after, newly developed Hamlin Meadows community. Offering an ideal blend of space, functionality, and modern living, this thoughtfully crafted floor plan features the primary suite and additional bedrooms on the main level, with the fifth and sixth bedrooms privately situated upstairs along with a spacious

  Dream Finders Homes Builder

  17060 Haggerty Hollow Dr, Winter Garden, FL 34787
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  $492,843 New Construction

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

  17025 Haggerty Hollow Dr, Winter Garden, FL 34787

  The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath,

  Dream Finders Homes Builder

  17025 Haggerty Hollow Dr, Winter Garden, FL 34787
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  $487,752 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,729 Sq Ft

  17013 Haggerty Hollow Dr, Winter Garden, FL 34787

  The Sage floorplan offers a thoughtfully designed two-story layout, ideal for comfortable living and modern convenience. This 3-bedroom, 2.5-bathroom townhome features an open concept on the first floor, highlighted by a spacious great room, a cozy lanai, and a breezeway that connects to a 2-car garage. Upstairs, the second floor boasts all three bedrooms, along with a versatile loft space,

  Dream Finders Homes Builder

  17013 Haggerty Hollow Dr, Winter Garden, FL 34787
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  $488,692 New Construction

  • 3 Beds
  • 3 Baths
  • 1,715 Sq Ft

  17019 Haggerty Hollow Dr, Winter Garden, FL 34787

  The Porter floorplan is an inviting two-story townhome designed with thoughtful spaces throughout. Featuring three bedrooms and two full bathrooms, the layout offers a smooth flow between living spaces. The first floor boasts a bright great room that opens into the dining area and lanai, perfect for entertaining or relaxation. Upstairs, all three bedrooms are thoughtfully arranged alongside a

  Dream Finders Homes Builder

  17019 Haggerty Hollow Dr, Winter Garden, FL 34787
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  $480,704 New Construction

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

  17001 Haggerty Hollow Dr, Winter Garden, FL 34787

  The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath,

  Dream Finders Homes Builder

  17001 Haggerty Hollow Dr, Winter Garden, FL 34787
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  $491,277 New Construction

  • 3 Beds
  • 3 Baths
  • 1,715 Sq Ft

  17007 Haggerty Hollow Dr, Winter Garden, FL 34787

  The Porter floorplan is an inviting two-story townhome designed with thoughtful spaces throughout. Featuring three bedrooms and two full bathrooms, the layout offers a smooth flow between living spaces. The first floor boasts a bright great room that opens into the dining area and lanai, perfect for entertaining or relaxation. Upstairs, all three bedrooms are thoughtfully arranged alongside a

  Dream Finders Homes Builder

  17007 Haggerty Hollow Dr, Winter Garden, FL 34787
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  $689,990 New Construction

  • 4 Beds
  • 4 Baths
  • 3,460 Sq Ft

  12438 Clear Sapphire Dr Unit 223, Winter Garden, FL 34787

  Under Construction. .

  Richard Selikoff K HOVNANIAN FLORIDA REALTY

  12438 Clear Sapphire Dr Unit 223, Winter Garden, FL 34787
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  $971,538 New Construction

  • 5 Beds
  • 3.5 Baths
  • 3,550 Sq Ft

  15280 Maritime Pine Dr, Winter Garden, FL 34787

  The Ellington is a spacious two-story home offers 3,550 square feet of elegant living, featuring 5 bedrooms and 3.5 bathrooms, along with a generous 3-car garage. The primary suite is conveniently located on the first floor, alongside the laundry for easy access. Upstairs, you’ll find four additional bedrooms and a massive game room—perfect for family fun! Relax and unwind outside under the

  Dream Finders Homes Builder

  15280 Maritime Pine Dr, Winter Garden, FL 34787
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  $765,377 Open Sat 1PM - 4PM

  • 4 Beds
  • 3 Baths
  • 3,038 Sq Ft

  17066 Haggerty Hollow Dr, Winter Garden, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. Welcome to the Biscayne, a thoughtfully designed two-story home offering the perfect balance of space, comfort, and flexibility. Featuring four bedrooms and three bathrooms, this floor plan is ideal for both everyday living and entertaining. The main level showcases an open-concept layout where the dining area flows

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  17066 Haggerty Hollow Dr, Winter Garden, FL 34787
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  $880,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,314 Sq Ft

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

  The Essex is a two-story home offering four bedrooms, three full bathrooms, one half bathroom, and a three-car garage. The spacious second-floor primary suite includes a luxurious bathroom with an oversized shower. A large covered lanai offers peaceful views of the backyard, while the open-concept layout and ample storage throughout make this home both elegant and functional. Additional

  Ashton Woods Builder

  17551 Lake Star Rd Unit 36646276, Winter Garden, FL 34787
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  Price To Be Determined New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,903 Sq Ft

  Autumn Plan at Westhaven at Ovation - Townes Collection, Winter Garden, FL 34787

  Toll Brothers, Inc. Builder

  14030 Lochend St Unit 39178511, Winter Garden, FL 34787
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  Price To Be Determined New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,863 Sq Ft

  Crowley Plan at Westhaven at Ovation - Townes Collection, Winter Garden, FL 34787

  Toll Brothers, Inc. Builder

  14030 Lochend St Unit 39178492, Winter Garden, FL 34787
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  $1,675,000 New Construction

  • 5 Beds
  • 5 Baths
  • 3,895 Sq Ft

  Custom Carrabelle Plan at Oakland Park, Winter Garden, FL 34787

  AR Homes Builder

  884 Tilden Oaks Trail Unit 37615294, Winter Garden, FL 34787
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  $360,000 Pre-Foreclosure

  • 3 Beds
  • 2.5 Baths
  • 1,732 Sq Ft

  15659 Jungle Aly, Winter Garden, FL 34787

  AGENTS - PLEASE VIEW REALTOR REMARKS IN THE MLS. Beautifully maintained town home 3 bed and 3 bath in the desirable Horizon West area of Winter Garden! This charming alley-facing property features an open-concept floor plan with spacious living and dining areas, a modern kitchen with solid surface countertops, stainless steel appliances, and a large island perfect for entertaining. Upstairs

  Dinorah Navarro LPT REALTY, LLC

  15659 Jungle Aly, Winter Garden, FL 34787
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  $5,000

  • 5 Beds
  • 3 Baths
  • 3,474 Sq Ft

  854 Lost Grove Cir, Winter Garden, FL 34787

  Foreclosure Auction Ends April 09, 2026 at 11:00 AM EST. Discover this inviting 5-bedroom, 3-bathroom single-family home, offering a wonderful opportunity to own in a desirable Winter Garden community. The list price is the opening bid for the online auction. Sold As-is. Explore more details and submit your bid through Federa Home App.

  Jamie Boone Jamie L Boone LLC

  854 Lost Grove Cir, Winter Garden, FL 34787
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  $550,000

  • 4 Beds
  • 3.5 Baths
  • 2,292 Sq Ft

  16632 Point Rock Dr, Winter Garden, FL 34787

  Short Sale. Located in the sought-after resort-style community of Waterleigh in Winter Garden, this spacious 2-story home features 4 bedrooms, 3.5 baths, and a versatile bonus room that can serve as a home office or additional bedroom. The first floor offers a guest bedroom with a full bath, a half bath, and an open-concept kitchen that flows into the living and dining areas—ideal for

  Melissa & Jon Lebron RE/MAX PREMIER REALTY

  16632 Point Rock Dr, Winter Garden, FL 34787
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  $220,000

  • 3 Beds
  • 1.5 Baths
  • 1,234 Sq Ft

  428 Sand Lime Rd, Winter Garden, FL 34787

  Short Sale. SHORT SALE APPROVED 3 bedroom, 1.5 bath townhome in Winter Garden Just a 7 minutes to downtown Winter Garden Come and see it. Great location, close to express way, restaurants, stores and easy access to FL Turnpike, SR 408, SR 429,Don't miss out the opportunity to own a piece of property. Low HOA

  Amanda Linsey VYLLA HOME

  428 Sand Lime Rd, Winter Garden, FL 34787
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  $2,130,760 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,992 Sq Ft

  1146 Prado Ln, Oakland, FL 34787

  Pre-Construction. To be built. Introducing the Hearth Stone Model by Davila Homes. Discover the perfect blend of modern luxury and everyday comfort in the Hearth Stone, a beautifully designed 3,992-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of

  Heather Spirazza REGENCY REAL ESTATE LLC

  1146 Prado Ln, Oakland, FL 34787
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  $2,238,120 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,204 Sq Ft

  1173 Prado Ln, Oakland, FL 34787

  Pre-Construction. To be built. Introducing the Sunburst Model by Davila HomesDiscover the perfect blend of modern luxury and everyday comfort in the Sunburst, a beautifully designed 4,204-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of

  Alexis Anderson REGENCY REAL ESTATE LLC

  1173 Prado Ln, Oakland, FL 34787

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