Winter Garden, FL Homes for Sale under $1,500,000

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  /49

  $1,375,000

  $125K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 4,130 Sq Ft

  8530 Bayview Crossing Dr, Winter Garden, FL 34787

  Now offered at $1,375,000 following a $124,000 price adjustment. This luxury residence presents an exceptional opportunity to own a beautifully designed home at its newly adjusted price.Rare opportunity to own an exceptional lakefront residence with a private dock and breathtaking panoramic water views in one of Winter Garden's premier resort-style communities. Offering approximately 4,663

  Katherine Perdomo COLDWELL BANKER REALTY

  8530 Bayview Crossing Dr, Winter Garden, FL 34787
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  /87

  $1,049,000

  New Construction $51K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,894 Sq Ft

  13181 Tollcross Way, Winter Garden, FL 34787

  Located in the highly desirable Westhaven at Ovation, this exceptional five bedroom, four bathroom home sits on one of the largest lots in the community with an impressive 0.28 acres, offering extra privacy, space, and an unbeatable setting. With no front or rear neighbors and peaceful pond views behind the home, this property delivers a rare combination of comfort and tranquility. Designed with

  Roberta do Nascimento Ferreira Vo FLORIDA CONNEXION PROPERTIES

  13181 Tollcross Way, Winter Garden, FL 34787
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  /84

  $1,299,000

  • 5 Beds
  • 3.5 Baths
  • 3,910 Sq Ft

  9969 Lost Creek Dr, Winter Garden, FL 34787

  Virtually Staged. Wake up to WATERFRONT SUNRISES, unwind beside your RESORT-STYLE POOL & SPA, and enjoy DISNEY FIREWORKS from your backyard every night. Situated on an OVERSIZED LAKEFRONT LOT spanning more than 1/3 ACRE with over 250 FEET OF DEPTH, this stunning 5 BEDROOM, 3.5 BATHROOM home offers the perfect blend of luxury, privacy, and lifestyle. The highly desirable NORTH HAVEN FLOOR PLAN

  Sabrina Freeman CHARLES RUTENBERG REALTY ORLANDO

  9969 Lost Creek Dr, Winter Garden, FL 34787
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  /55

  $1,099,000

  • 6 Beds
  • 5 Baths
  • 4,741 Sq Ft

  14067 Jomatt Loop, Winter Garden, FL 34787

  Experience luxury living in this exceptional 6-bedroom, 5-bathroom residence located in the highly sought-after Cypress Reserve community of Winter Garden. Perfectly positioned on a premium homesite with no rear neighbors, this impressive home offers exceptional privacy, tranquil conservation views, and a versatile floor plan designed for today’s lifestyle. The open-concept design showcases

  Kim Byerly THE REAL ESTATE COLLECTION LLC

  14067 Jomatt Loop, Winter Garden, FL 34787
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  /69

  $1,450,000

  • 4 Beds
  • 3.5 Baths
  • 3,086 Sq Ft

  15619 Giant Foxtail Ct, Winter Garden, FL 34787

  Captivating water and golf course views set the stage for a chic and distinguished single-story residence in Lakeshore Preserve. This better-than-new home boasts a great room floorplan with split bedroom layout, sliding pocket doors, an exceptional screened pool patio area with hybrid saltwater and chlorine pool with sun shelf and water features, plus tranquil lake beyond. Elegant white on white

  Rob Rahter STOCKWORTH REALTY GROUP

  15619 Giant Foxtail Ct, Winter Garden, FL 34787
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  /56

  $1,300,000

  $99K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,097 Sq Ft

  243 Zachary Wade St, Winter Garden, FL 34787

  PRICE IMPROVEMENT! Refined Waterfront Living in Winter Garden’s Coveted Golf Cart District! Set within one of Downtown Winter Garden’s most desirable gated enclaves, this exceptional waterfront residence offers a rare blend of sophistication, privacy, and effortless Florida living—perfectly positioned in the highly sought-after golf cart district. Designed to maximize light and livability, the

  Alexis Anderson REGENCY REAL ESTATE LLC

  243 Zachary Wade St, Winter Garden, FL 34787
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  /32

  $1,200,000

  $100K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,171 Sq Ft

  205 Surprise Dr, Winter Garden, FL 34787

  PRICE ADJUSTED to reflect recent appraisal, this rare parcel presents immediate value- with vacant land ready for expansion or additional income potential with future development. Discover an exceptional property in the heart of highly desirable GOLF CART DISTRICT of Winter Garden. Situated on an expansive parcel totaling 3/4 of an acre, this unique estate offers unmatched space, charm and

  Alison Scorsone RE/MAX PRIME PROPERTIES

  205 Surprise Dr, Winter Garden, FL 34787
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  /31

  $1,080,000

  Pre-Foreclosure

  • 4 Beds
  • 5 Baths
  • 3,881 Sq Ft

  1651 Amsel Falls Park Terrace, Winter Garden, FL 34787

  Welcome home to this beautifully maintained 4-bedroom, 3 full bath, residence in sought-after Twinwaters. Featuring a designer kitchen with full-extension soft-close drawers and cabinets, 10-foot ceilings on the main level, 9-foot ceilings upstairs, crown molding, and central vacuum, this home offers both comfort and thoughtful upgrades throughout. Enjoy peaceful views of the expansive

  Jen Dollar FOLIO REALTY LLC

  1651 Amsel Falls Park Terrace, Winter Garden, FL 34787
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  /97

  $1,160,000

  $30K PRICE DROP

  • 6 Beds
  • 5 Baths
  • 4,305 Sq Ft

  10067 Austrina Oak Loop, Winter Garden, FL 34787

  Seller Motivated , Welcome Home! This beautifully renovated 4,305 sq. ft. single-family residence offers the perfect blend of modern upgrades and inviting comfort, located in one of Winter Garden’s well sought-after communities. Discover elegant porcelain tile flooring throughout the first floor, leading to a spacious, updated kitchen featuring quartz countertops, a smart cooktop, and decorative

  Shi Knoblock KELLER WILLIAMS CLASSIC

  10067 Austrina Oak Loop, Winter Garden, FL 34787
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  /47

  $1,165,000

  $10K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,667 Sq Ft

  925 Easley Ave, Winter Garden, FL 34787

  Welcome to a life beautifully lived. Situated on a premier corner lot in Oakland Park, Winter Garden's golf cart community, this exceptional residence blends thoughtful design, effortless indoor-outdoor living, & a private tropical retreat.Freshly redesigned professional landscaping with premium weed barrier, smart irrigation, app control, & a mature Medjool date palm creates stunning curb

  Matt McKee COMPASS FLORIDA LLC

  925 Easley Ave, Winter Garden, FL 34787
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  /54

  $1,185,000

  $10K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 4,026 Sq Ft

  17588 Lake Star Rd, Winter Garden, FL 34787

  Step into better-than-new living with this beautifully upgraded home that rival's today's new construction--without the wait. This exceptional five-bedroom, four-bathroom home situated on Lake Star located in the highly desirable Horizon West area. The inviting entryway leads to a spacious, bright, and open-concept layout filled with abundant natural light and wood look plank tile flooring on the

  Dee Lund COLDWELL BANKER REALTY

  17588 Lake Star Rd, Winter Garden, FL 34787
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  /2

  $1,037,987

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,688 Sq Ft

  17090 Haggerty Hollow Dr, Winter Garden, FL 34787

  The Anna Maria with Bonus floorplan is an expansive two-story home designed to accommodate a growing family, offering five bedrooms and three and a half bathrooms. On the main floor, you'll find a spacious great room adjacent to a well-appointed dining room and kitchen, creating an ideal space for gatherings. The primary suite, featuring a large walk-in closet and private bath, is thoughtfully

  Dream Finders Homes Builder

  17090 Haggerty Hollow Dr, Winter Garden, FL 34787
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  /42

  $1,350,000

  $50K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,728 Sq Ft

  9508 Quiet Ln, Winter Garden, FL 34787

  Virtually Staged. Rare opportunity in Winter Garden's coveted Lake Avalon: a fully fenced and gated 5-acre mini-ranch in the Valley View enclave, where genuine Lake Avalon water and conservation views meet true rural freedom — bring your horses, livestock, or recreational vehicles — just minutes from Hamlin Town Center, Walt Disney World, and SR-429.Spanning nearly 3,800 SF, this thoughtfully

  Jared Jones EXP REALTY LLC

  9508 Quiet Ln, Winter Garden, FL 34787
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  /42

  $1,165,000

  $15K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 3,624 Sq Ft

  15741 Sweet Lemon Way, Winter Garden, FL 34787

  ***PRICED TO SELL!*** WELCOME to this stunning and highly desirable two-story Xavier floor plan by K. Hovnanian Homes, perfectly positioned on a premium homesite with no rear neighbors, offering exceptional privacy and a peaceful backyard retreat. Located in the heart of Horizon West, just minutes from Hamlin Town Center, this exceptional residence combines luxury, functionality, and modern

  Cristiane Carneiro Spfndola Rocha L WRA BUSINESS & REAL ESTATE

  15741 Sweet Lemon Way, Winter Garden, FL 34787
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  /38

  $1,199,999

  • 4 Beds
  • 1.5 Baths
  • 2,246 Sq Ft

  17425 Lake Ingram Rd, Winter Garden, FL 34787

  Rare opportunity to own 6.8 acres in the heart of Horizon West! Zoned A1 with NO HOA. Zoned for top rated schools. Bring your horses, goats, chickens and build your dream home. The property is located at the end of a dead end street. Very private and isolated. One side of the property is flanked by retention ponds, the other side is the future home of a community park, and far in the backyard is

  Tamar Hill THE PROPERTY PROS REAL ESTATE, INC

  17425 Lake Ingram Rd, Winter Garden, FL 34787
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  /31

  $1,150,000

  • 4 Beds
  • 3 Baths
  • 2,986 Sq Ft

  16071 Barkly Ridge Ct, Winter Garden, FL 34787

  Enchanting newly built home in Avalon Ridge with a private pool, located in one of the most desirable areas of Winter Garden. This beautiful residence has been thoughtfully designed and features 4 bedrooms with carpet flooring, 3 full bathrooms, and a perfect blend of modern space, functionality, and elegant finishes. The living area features sliding glass doors that open to the outdoor space and

  Thiago Ataide WRA BUSINESS & REAL ESTATE

  16071 Barkly Ridge Ct, Winter Garden, FL 34787
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  /68

  $1,025,000

  Open Sun 12PM - 2PM $175K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,389 Sq Ft

  13536 Sunset Lakes Cir, Winter Garden, FL 34787

  Experience luxury living in this gorgeous home in the highly sought after Sunset Lakes community in Winter Garden. This FULLY-REMODELED, 5-bedroom, 4-bath POOL/SPA home sits on a SERENE POND and offers 3,389 sq. ft. of beautifully designed living space on OVER HALF AN ACRE, complete with a three-car side entry garage. Four of the 5 bedrooms are conveniently located on the first floor (including

  Diane Sterling KELLER WILLIAMS ADVANTAGE REALTY

  13536 Sunset Lakes Cir, Winter Garden, FL 34787
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  /90

  $1,100,000

  • 5 Beds
  • 4 Baths
  • 3,617 Sq Ft

  16044 Citrus Knoll Dr, Winter Garden, FL 34787

  Welcome to this exceptional pool home in the highly sought-after gated community of Hickory Hammock in Winter Garden. Offering more than 3,600 square feet beautifully designed living space, this impressive five bedroom, four bathroom, 4 car garage residence blends timeless elegance with everyday functionality. From the moment you step inside, you'll be captivated by soaring ceilings, georgous

  Kaitlin Sidders HOGAN REALTY GROUP INC

  16044 Citrus Knoll Dr, Winter Garden, FL 34787
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  /12

  $1,157,190

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,902 Sq Ft

  650 Medora Way, Winter Garden, FL 34787

  Under Construction. Under Construction. Welcome to Lakeview Village Estates, an exclusive new community by award-winning Davila Homes,featuring just 40 luxury residences crafted with exceptional attention to detail. Each home is thoughtfully designed to blend comfort, durability,and timeless architectural elegance. Introducing The Cypress floor plan, offering 4 bedrooms, 3 bathrooms, and

  Tatiana Souza DAVILA HOMES

  650 Medora Way, Winter Garden, FL 34787
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  /3

  $1,000,000

  • Land
  • 37,026 Sq Ft
  • $1,176,471 per Acre

  851 9th St, Winter Garden, FL 34787

  VERY RARE FIND . EXCELLENT LOCATION IN WINTER GARDEN . CLOSE TO HWY 50 ON 9TH STREET . SITE APPROVED FOR 5400 SQ FOOT BLDMANY USES . COMES WITH BUILDING PLANS AS WELL , READY TO BUILD . GROUND LEASE OPTION IS ALSO AVAIABLE .

  Nidhi Gupta HOME WISE REALTY GROUP, INC.

  851 9th St, Winter Garden, FL 34787
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  $1,219,000

  $39K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,022 Sq Ft

  15594 Shorebird Ln, Winter Garden, FL 34787

  One or more photo(s) has been virtually staged. EXPERIENCE ELEVATED LAKEFRONT LIVING IN THE HEART OF HORIZON WEST!!! Welcome to 15594 Shorebird Lane, an exceptional Toll Brothers lakefront residence located in the Lakeshore Preserve community of Winter Garden. Perfectly positioned on a premium oversized 0.34-acre homesite overlooking beautiful Panther Lake, this stunning 4-bedroom, 3.5-bath home

  Ana Castillo PREMIUM PROPERTIES R.E SERVICE

  15594 Shorebird Ln, Winter Garden, FL 34787
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  /79

  $1,349,000

  Open Sat 12PM - 2:30PM $146K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 2,800 Sq Ft

  217 W Bay St, Winter Garden, FL 34787

  Stunning family home with an option to purchase the fully renovated 3 bed, 2 bath home next door - perfect for inlaws home, investment property, or just extra family space (call agent for details)!! Experience the best of Historic Winter Garden living in this brand-new Craftsman-style home, ideally located just steps from downtown dining, shopping, entertainment, and the renowned West Orange

  Sue Webb WATSON REALTY CORP.

  217 W Bay St, Winter Garden, FL 34787
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  /65

  $1,149,950

  $50K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,170 Sq Ft

  156 Stanton Estates Cir, Winter Garden, FL 34787

  **We've just introduced a significant price reduction, creating an exceptional opportunity for new owners. ** **Welcome to Golf Cart Life in Historic Downtown Winter Garden** Nestled within Stanton Estates — an exclusive enclave of just 45 luxury homes — this contemporary masterpiece places you in the heart of **Winter Garden’s vibrant Golf Cart District**, where every day feels like a getaway.

  Joseph Thomas, Jr FATHOM REALTY FL LLC

  156 Stanton Estates Cir, Winter Garden, FL 34787
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  /42

  $1,200,000

  • 5 Beds
  • 3.5 Baths
  • 3,911 Sq Ft

  10198 Merrymeeting Bay Dr, Winter Garden, FL 34787

  Stunning lakefront living in the heart of Waterleigh! This 5 bedroom, 3 and a half bathroom home offers an open concept downstairs living space, a dedicated home office, and custom plantation shutters throughout. The primary suite is on the first floor providing lake views and a door to the screened in patio. Relax on the screened in patio with serene lake views, or enjoy the beautifully updated

  Kerstin Crow LOKATION

  10198 Merrymeeting Bay Dr, Winter Garden, FL 34787
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  /38

  $1,095,000

  $124K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,225 Sq Ft

  64 N Park Ave, Winter Garden, FL 34787

  Welcome to 30 North Park, an exceptional townhome located in the heart of Historic Downtown Winter Garden — directly on the West Orange Trail and just steps from Plant Street Market, Crooked Can Brewery, local dining, shopping, and the weekly Farmer’s Market. This modern farmhouse-style residence offers four spacious bedrooms, each with a private en-suite bathroom and custom-fitted closets,

  Steve Healy CORCORAN PREMIER REALTY

  64 N Park Ave, Winter Garden, FL 34787

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