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

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  /21

  $449,000

  • 4 Beds
  • 2.5 Baths
  • 1,696 Sq Ft

  9338 Tyrella Pine Trail, Winter Garden, FL 34787

  Beautiful 4 bedrooms, 2.5 bathrooms, 2 car garage home located in the desirable Watermark community in Winter Garden. Home is perfectly located near the clubhouse (5min walk distance), all tile on the first floor and tray ceiling in the master suite. Watermark has resort-like amenities that includes a pool with splash pad, playground, club house, fitness center, tennis court and nearby

  Mengshi Lu JOY ESTATE ENTERPRISE INC

  9338 Tyrella Pine Trail, Winter Garden, FL 34787
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  /27

  $420,000

  • 3 Beds
  • 2.5 Baths
  • 1,844 Sq Ft

  15182 Sunrise Grove Ct, Winter Garden, FL 34787

  Welcome to 15183 Sunrise Grove Court, a beautiful townhome located in the highly sought-after Hickory Hammock community in Winter Garden, Florida, where comfort, lifestyle, and an excellent location come together perfectly. Offering 1,844 square feet of living space and 2,393 total square feet, this property features 3 bedrooms, 2 full bathrooms, and 1 half bath, providing the layout and space

  Natsue Siqueira FLORIDA REALTY INVESTMENTS

  15182 Sunrise Grove Ct, Winter Garden, FL 34787
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  /19

  $495,000

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

  12253 Bracco St, Winter Garden, FL 34787

  NEW! NEW! CONSTRUCTION! Move-in ready! You can be the very first to peel the plastic off the brand-new appliances! This beautiful energy-efficient home in the sought-after Highland Ridge community offers a spacious open floor plan perfect for modern living. The stylish kitchen features a large island overlooking a generous dining area and family room. Ideal for entertaining or everyday family

  Gil Semedo LIFESTYLE INTERNATIONAL REALTY

  12253 Bracco St, Winter Garden, FL 34787
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  /41

  $438,000

  • 3 Beds
  • 2 Baths
  • 1,720 Sq Ft

  15693 Signature Dr, Winter Garden, FL 34787

  This amazing 3 bedrooms and 2 full bathrooms in good condition with new floor Single Family Home is located in the heart of New Independence in Winter Garden. The community is minutes to Disney World, charming for family with lots of conservation, park areas, walking/bike path, community pool, tennis and basketball courts, fitness center, Cable and Internet included. The home includes a washer

  Eric Jia NUMBER 1 BROKER, LLC

  15693 Signature Dr, Winter Garden, FL 34787
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  /48

  $499,800

  • 4 Beds
  • 2.5 Baths
  • 2,011 Sq Ft

  14030 Frasier St, Winter Garden, FL 34787

  SELLER IS OFFERING A $5,000 CREDIT TOWARDS BUYER'S CLOSING COSTS WITH AN ACCEPTABLE OFFER!!! Experience modern Florida living in this move-in ready 4-bedroom, 2.5-bath home in Highland Ridge, Winter Garden, featuring approximately $33,000 in upgrades!! Perfectly situated just steps from the community clubhouse, this home offers a refined lifestyle with amenities such as a community pool, cabana,

  Tatiana Alencar BAHIA INTERNATIONAL REALTY

  14030 Frasier St, Winter Garden, FL 34787
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  /22

  $469,900

  • 3 Beds
  • 2.5 Baths
  • 2,012 Sq Ft

  15684 Orange Harvest Loop, Winter Garden, FL 34787

  Welcome to 15684 Orange Harvest Loop, a 3-bedroom, 2.5-bath townhouse with a loft, located in the highly desirable Hickory Hammock neighborhood of Winter Garden, Florida. Known for its charming architecture and resort-style amenities, Hickory Hammock offers an exceptional lifestyle in one of Winter Garden's most sought-after communities.This inviting townhouse features a bright, open floor

  Sue Piesik Charles Rutenberg Realty Inc

  15684 Orange Harvest Loop, Winter Garden, FL 34787
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  /41

  $419,990

  • 3 Beds
  • 2.5 Baths
  • 1,617 Sq Ft

  5637 Water Rose Rd, Winter Garden, FL 34787

  ***WINDERMERE HIGH SCHOOL*** Price improvement – great opportunity in Signature Lakes / Winter Garden.Enjoy the best of Florida living in this beautiful townhome located in the highly desirable Signature Lakes / Independence community in Winter Garden. This well-maintained 3-bedroom, 2.5-bath home offers a functional layout with comfortable living spaces and plenty of natural light. The

  Luciana Amorim Panajotti FLORIDA CONNEXION PROPERTIES

  5637 Water Rose Rd, Winter Garden, FL 34787
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  /28

  $474,790 New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,770 Sq Ft

  16286 Bright Leaf Rd, Winter Garden, FL 34787

  Discover Silverleaf Oaks in Winter Garden! This new home community will feature a collection of single-family and townhomes in desirable Horizon West. Located in the heart of Orlando’s attractions, residents will enjoy an array of amenities, including a resort-style pool, cabana, and playground – without a CDD. Plus, minutes to shopping, dining, and entertaining - Now Open!Introducing the

  Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  16286 Bright Leaf Rd, Winter Garden, FL 34787
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  /41

  $445,000

  • 3 Beds
  • 2.5 Baths
  • 1,662 Sq Ft

  16425 Prairie School Dr, Winter Garden, FL 34787

  Welcome to 16425 Prairie School Dr, an exceptional 2021-built residence offering 3 bedrooms, 2.5 baths, and 1,662 square feet of thoughtfully designed living space in one of Winter Garden’s most sought-after growth corridors. Crafted for modern lifestyles, this impeccably maintained townhome showcases a bright, open-concept main level adorned with elegant ceramic tile flooring for both

  Nairobi Rondon LPT REALTY, LLC

  16425 Prairie School Dr, Winter Garden, FL 34787
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  /30

  $450,000

  • 2 Beds
  • 2 Baths
  • 1,375 Sq Ft

  14501 Grove Resort Ave Unit 1617, Winter Garden, FL 34787

  Complete turnkey unit with prime views to the lake, pool and Disney parks area. One of the few units that allow to enjoy the nightly fireworks from the balcony. The Grove Resort & Water Park, Orlando's newest luxury vacation home community offers owners privacy and convenience with a full suite of amenities including multiple bars and restaurants, full service spa, water park, breathtaking

  Marco Rangel CENTURY 21 Tenace Realty

  14501 Grove Resort Ave Unit 1617, Winter Garden, FL 34787
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  /48

  $490,000

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

  15605 Jungle Aly, Winter Garden, FL 34787

  Location at its finest! This exceptional corner-unit townhome offers serene WATER VIEWS and borders a private PRESERVE, providing rare privacy and natural beauty. Thoughtfully designed, this 4-bedroom, 3 full-bath residence also features a spacious loft, wood-look TILE flooring, upgraded lighting, and an extended fenced patio (approximately 13x25) — perfect for outdoor entertaining. The 2-car

  Diana Lopera MY REALTY GROUP, LLC.

  15605 Jungle Aly, Winter Garden, FL 34787
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  /29

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 1,868 Sq Ft

  15334 Murcott Blossom Blvd, Winter Garden, FL 34787

  Beautiful 3-bedroom, 2.5-bathroom townhouse available in the great Summerlake community of Winter Garden. This home features an open floor plan, spacious living areas, and a 2-car garage. An additional room at the front of the house offers the perfect space for a home office or flex room. The Summerlake community provides exceptional amenities, including a pool, playground and dog park.

  Ligia Coelho WRA BUSINESS & REAL ESTATE

  15334 Murcott Blossom Blvd, Winter Garden, FL 34787
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  /9

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,689 Sq Ft

  9468 Komika Ln, Winter Garden, FL 34787

  Beautiful 3BR/2BA single-family home built in 2020 in the highly sought-after Waterleigh community. Offering 1,689 heated sq ft with an open-concept layout, modern finishes, and spacious living areas. Enjoy resort-style amenities including clubhouse, pool, fitness center, and playground. Conveniently located near top-rated schools, shopping, dining, and major highways.

  Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

  9468 Komika Ln, Winter Garden, FL 34787
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  /42

  $448,900

  • 4 Beds
  • 3.5 Baths
  • 2,303 Sq Ft

  9814 Amber Chestnut Way, Winter Garden, FL 34787

  Expect to be impressed with this 4BR home in the desirable Watermark community. Room for everyone and everything! Step inside to a soaring ceiling and open common living space. Here, clerestory windows at the second story level help bathe the space in light. Gourmet style kitchen reflects the latest style trends and features an abundance of counter/cabinet space, granite counters, island and

  Chris Bessette KELLER WILLIAMS CLASSIC

  9814 Amber Chestnut Way, Winter Garden, FL 34787
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  /45

  $489,990 New Construction

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

  15351 Hamlin Park Dr, Winter Garden, FL 34787

  Experience modern townhome living in this beautifully designed three-story residence located in Parkview at Hamlin in Winter Garden. This thoughtfully planned home features three private suites, including a convenient first-floor suite and a spacious third-floor primary suite, offering flexibility and privacy for today’s lifestyle. The second floor serves as the heart of the home, showcasing an

  Ashton Woods Builder

  15351 Hamlin Park Dr, Winter Garden, FL 34787
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  /41

  $426,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 3 Baths
  • 2,034 Sq Ft

  15381 Honeybell Dr, Winter Garden, FL 34787

  Live in the heart of Hamlin Reserve, this stylish executive townhome sits directly across from the community pool and playground, just a five-minute drive or short distance to Hamlin Town Center for convenient shopping, dining and everyday essentials in Horizon West. Spanning over 2,000 square feet, this four-bedroom, three-bath home with two-car garage and private patio is thoughtfully designed

  JJ Mackle PREMIER SOTHEBY'S INTL. REALTY

  15381 Honeybell Dr, Winter Garden, FL 34787
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  /3

  $496,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,772 Sq Ft

  Amelia Plan at Hamlin Meadows - 40' Homesites, Winter Garden, FL

  The Amelia floor plan offers the ease of one-story living with a smart and stylish layout featuring three bedrooms, two bathrooms, and a two-car garage. A spacious great room flows effortlessly into the dining and kitchen areas, making entertaining and everyday living a breeze. The private primary suite is tucked away with a large walk-in closet and a well-appointed bath. Two additional bedrooms

  Dream Finders Homes Builder

  0 Hamlin Meadows St Unit 39127935, Winter Garden, FL
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  /43

  $473,000

  • 4 Beds
  • 2.5 Baths
  • 1,992 Sq Ft

  14143 Title Way, Winter Garden, FL 34787

  Experience the perfect combination of modern upgrades, unbeatable convenience, and premium outdoor space in this stunning Winter Garden townhouse. Located in a highly sought-after, family-friendly neighborhood, this property offers a lifestyle of unmatched comfort and ease. Top-Tier Schools & WalkabilitySay goodbye to stressful morning drop-off lines! Nestled in an A-rated school district,

  Zhe Wang AAA GLOBAL VENTURES PA

  14143 Title Way, Winter Garden, FL 34787
• 

  

  /46

  $469,900

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

  12140 Bracco St, Winter Garden, FL 34787

  One or more photo(s) has been virtually staged. Stunning Move-In Ready Home in Highland Ridge | 3 Bedrooms, 2.5 Baths, Loft, Premium Lot, $30K in Upgrades!Located just steps from the community clubhouse and resort-style amenities, this beautifully maintained, like-new home is nestled in the highly sought-after Highland Ridge community in Winter Garden. Featuring 3 bedrooms, 2.5 bathrooms, and

  Tatiana Alencar BAHIA INTERNATIONAL REALTY

  12140 Bracco St, Winter Garden, FL 34787
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  /44

  $460,000

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

  14501 Grove Resort Ave Unit 2101, Winter Garden, FL 34787

  Experience resort-style living and exceptional investment potential with this luxurious first floor condo located in The Grove Resort & Water Park, Orlando’s premier vacation destination. Ideally situated just 5 minutes from Walt Disney World, this fully furnished, turnkey residence offers a perfect combination of elegance, comfort, and convenience. Notice the Soaring Ceilings in this beautiful

  Jeff Stewart WEICHERT REALTORS HALLMARK PROPERTIES

  14501 Grove Resort Ave Unit 2101, Winter Garden, FL 34787
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  /38

  $495,000

  • 3 Beds
  • 2.5 Baths
  • 1,994 Sq Ft

  13837 Lanyard Way, Winter Garden, FL 34787

  Welcome to 13837 Lanyard Way, a home that exudes elegance and comfort. The kitchen is a chef's dream with all stainless steel appliances and a functional kitchen island. A walk-in pantry provides ample storage for all your culinary needs. The primary bedroom is a sanctuary with a spacious walk-in closet. The primary bathroom is a haven of relaxation with double sinks. Outside, a storage shed

  Karen Albright OPENDOOR BROKERAGE LLC

  13837 Lanyard Way, Winter Garden, FL 34787
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  /24

  $400,000

  • 3 Beds
  • 2 Baths
  • 1,154 Sq Ft

  711 Burch Ave, Winter Garden, FL 34787

  Welcome to this lovely 3-bedroom, 2-bath home, just minutes from the heart of Downtown Winter Garden. Freshly painted inside and out, with a brand-new kitchen countertop, it feels fresh, modern, and move-in ready. The layout is cozy and practical—perfect for families or anyone looking to enjoy all the charm and convenience of Winter Garden living.One great bonus is the additional room with

  Carina Davis LAKESIDE REALTY WINDERMERE INC

  711 Burch Ave, Winter Garden, FL 34787
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  /50

  $414,900

  • 3 Beds
  • 2.5 Baths
  • 1,655 Sq Ft

  14971 Apollo Bond Dr, Winter Garden, FL 34787

  One or more photo(s) has been virtually staged. This luxurious townhouse, built in 2019, is located in the Watermark Community in Horizon West, known for its top-rated A schools. The home has an open floor plan with tile flooring, kitchen with 42" cabinets, granite countertops, and a butler's pantry. Upstairs, you'll find three bedrooms, including a master suite with dual sinks, a walk-in shower,

  Adriana Lima WRA BUSINESS & REAL ESTATE

  14971 Apollo Bond Dr, Winter Garden, FL 34787
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  /36

  $449,500 Open Sat 1PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 1,584 Sq Ft

  17723 Japonica Bloom Dr, Winter Garden, FL 34787

  Northlake at Ovation! One of Winter Garden's Best Kept Secrets. This Hidden Community is tuckedaway among beautiful conservation areas of Horizon's West. Ashton Woods most desirable floor plan(The Kendall ll) is an Award Winning 3 Bedrooms, 2 full bathrooms and one half bath with 1584Square feet of living area, Brick Paver Courtyard and Full Size 2 Car Garage. The First Floor

  Thad Czapka COLDWELL BANKER REALTY

  17723 Japonica Bloom Dr, Winter Garden, FL 34787
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  /32

  $485,000

  • 3 Beds
  • 2.5 Baths
  • 1,905 Sq Ft

  900 Walkers Grove Ln, Winter Garden, FL 34787

  Downtown Winter Garden – Golf Cart District! Don’t miss this amazing opportunity to own a well maintained 3-bedroom, 2.5-bath townhome in the heart of Downtown Winter Garden, right in the highly desirable Golf Cart District—with no rear neighbors! Built in 2015, this home features a spacious layout with tile flooring throughout the first floor, a welcoming foyer, and an open-concept kitchen with

  Laura Taylor SPECTRUM PROPERTY GROUP LLC

  900 Walkers Grove Ln, Winter Garden, FL 34787
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  /31

  $480,000

  • 3 Beds
  • 2 Baths
  • 1,796 Sq Ft

  14342 Breda Center Loop, Winter Garden, FL 34787

  PRICE ADUSTMENT**PRICED TO SELL**Welcome home to this charming single-story gem, full of warmth and character! Enjoy relaxing mornings on the spacious front porch or cozy evenings on the covered back patio. Inside, high 9’4” ceilings and beautiful upgraded tile flooring create an open, airy feel throughout. The bright, spacious kitchen sits at the heart of the home and overlooks the great

  Maribel Ramos VESTI LLC

  14342 Breda Center Loop, Winter Garden, FL 34787
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  /10

  $485,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

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

  Private primarysuite with bath and walk-in closet. Beautiful kitchen with plenty of counterspace for entertaining. Open dining area and great room near kitchen. Covered lanai off dining area for enjoying outdoors. Rear 2-car garage with access to laundry room.

  K. Hovnanian Homes Builder

  15221 Blue Peacock Ln Unit 36450266, Winter Garden, FL 34787
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  /6

  $429,990

  • 3 Beds
  • 2.5 Baths
  • 1,717 Sq Ft

  15066 Book Club Rd, Winter Garden, FL 34787

  Beautiful move in ready 3 Bedroom 2.5 Bathroom Townhome in Storey Grove. Ground floor features formal living and dining areas with beautiful soft grey walls and easy care tile. The guest bathroom features modern cabinets, solid surface countertops and storage closet. The family room is just off the kitchen which has modern cabinets, solid surface countertops, custom tile backsplash and stainless

  Lidia Barberini AGENT TRUST REALTY CORPORATION

  15066 Book Club Rd, Winter Garden, FL 34787
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  /6

  $435,000

  • 3 Beds
  • 2.5 Baths
  • 1,636 Sq Ft

  10534 Tribute Dr, Winter Garden, FL 34787

  This stunning and spacious townhome will exceed all expectations! Built in 2023 and designed with modern living in mind, this 3-bedroom, 2.5-bath home feels like a model property and offers the perfect blend of style, comfort, and investment potential. The first floor showcases an open-concept design with upgraded tile flooring, a beautifully appointed kitchen featuring solid-surface countertops,

  Solon Potenciano Silva, Jr LEGACY PLUS REALTY

  10534 Tribute Dr, Winter Garden, FL 34787
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  /59

  $489,000

  • 3 Beds
  • 3 Baths
  • 1,955 Sq Ft

  14010 Scarlet Aster Aly, Winter Garden, FL 34787

  Seller is offering a limited-time buyer incentive, including seller-paid closing costs or interest rate buy-down, to help reduce upfront and monthly expenses. Experience modern luxury in this beautifully crafted like new townhome by RockWell Homes. The Edison floor plan offers three spacious bedrooms, three stylish bathrooms, and a two car garage. Thoughtfully designed for comfort and outdoor

  Ana Afshin GERMEROTH REALTY LLC

  14010 Scarlet Aster Aly, Winter Garden, FL 34787
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  /25

  $450,000

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

  14446 Whittridge Dr, Winter Garden, FL 34787

  Welcome to 14446 Whittridge Dr., Winter Garden, FL 34787 – a charming home nestled in the highly sought-after Independence community! This beautifully maintained 3-bedroom, 2-bath home offers a light and airy open-concept floor plan with high ceilings and abundant natural light throughout. From the moment you step onto the inviting covered front porch, you’ll feel right at home. Inside, the

  Jasmine Reierson THE C SMITH REAL ESTATE GROUP LLC

  14446 Whittridge Dr, Winter Garden, FL 34787
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  /30

  $489,990 New Construction

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

  15333 Hamlin Park Dr, Winter Garden, FL 34787

  Experience modern townhome living in this beautifully designed three-story residence located in Parkview at Hamlin in Winter Garden. This thoughtfully planned home features three private suites, including a convenient first-floor suite and a spacious third-floor primary suite, offering flexibility and privacy for today’s lifestyle. The second floor serves as the heart of the home, showcasing an

  Ashton Woods Builder

  15333 Hamlin Park Dr, Winter Garden, FL 34787
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  /93

  $435,000

  • 3 Beds
  • 2.5 Baths
  • 1,814 Sq Ft

  16156 Arbor Crest Aly, Winter Garden, FL 34787

  Welcome to this beautifully maintained end-unit townhome in the sought-after Waterleigh community of Winter Garden offering 3 bedrooms, 2.5 baths, and a versatile loft in a location that truly captures the Florida lifestyle. A recently painted interior and durable LVP flooring on the stairs and throughout the second floor create a fresh, modern feel while abundant natural light fills the open

  Alex Vastardis COLDWELL BANKER REALTY

  16156 Arbor Crest Aly, Winter Garden, FL 34787
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  /50

  $475,000 Open Sat 11AM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,705 Sq Ft

  16385 Admirals Cove Ln, Winter Garden, FL 34787

  **Sellers are highly motivated** Welcome to this beautiful home in Waterleigh, where the magic of Disney fireworks, golf cart living, and a true neighborhood feel come together in one of Winter Garden’s most desirable communities. This lovely 3-bedroom, 2-bath home offers a bright, open-concept layout that makes everyday living and entertaining feel easy. The kitchen overlooks the spacious living

  Shaheda Gordon-Jefferson LIFESTYLE INTERNATIONAL REALTY

  16385 Admirals Cove Ln, Winter Garden, FL 34787
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  /36

  $460,000

  • 3 Beds
  • 2 Baths
  • 1,690 Sq Ft

  6108 Lewis And Clark Ave, Winter Garden, FL 34787

  OPPORTUNITY!!!!!!! AMAZING HOME in WINTER GARDEN, set in Signature Lakes, within the INDEPENDENCE COMMUNITY of Horizon West. This single-story residence was recently remodeled and is move-in ready, with new laminate flooring in all three bedrooms, fresh interior and exterior paint, a new irrigation system and new garage door springs. The location is excellent, in South Winter Garden, just minutes

  Marilu Drummond AMG INTERNATIONAL REALTY

  6108 Lewis And Clark Ave, Winter Garden, FL 34787
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  /53

  $499,900 Open Sat 11AM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 2,067 Sq Ft

  6530 Pasturelands Place, Winter Garden, FL 34787

  Welcome to your New Home with Brand New Inverter AC unit in a tranquil setting with a water view of a beautiful pond and conservation area. This well maintained townhome in the highly desirable Independence community of Horizon West. Over 2,000 sq ft, this home blends comfort, style, and convenience. Step inside the open floor plan, the spacious living and dining areas flow into the kitchen,

  Amber Draus KELLER WILLIAMS REALTY AT THE PARKS

  6530 Pasturelands Place, Winter Garden, FL 34787
• 

  

  /14

  $440,000

  • Land
  • 0.26 Acre
  • $1,692,308 per Acre

  1161 Prado Ln, Oakland, FL 34787

  Nestled in the heart of Oakland, Florida, this expansive homesite offers the perfect canvas to build your dream home with custom home builder, Pioneer Builders. Set in an illustrious community, called the Grove, this generously sized lot is ideal for crafting your unique custom home. The Grove is situated within Oakland’s most sought-after neighborhood known for its upscale charm and ideal

  Alexis Anderson REGENCY REAL ESTATE LLC

  1161 Prado Ln, Oakland, FL 34787

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