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

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  /28

  $420,000

  $5K PRICE DROP

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

  15755 Water Spring Blvd, Winter Garden, FL 34787

  Discover stylish and comfortable living in the highly sought after Storey Grove community of Winter Garden! This spacious 3 bedroom, 2 bathroom townhome offers the perfect blend of comfort, convenience, and modern upgrades in a great family friendly neighborhood. The home features beautiful plank tile flooring downstairs and laminate flooring upstairs, creating a seamless, low maintenance design

  Karen Grau REVEL REALTY LLC

  15755 Water Spring Blvd, Winter Garden, FL 34787
• 

  

  

  /40

  $490,900

  New Construction

  • 3 Beds
  • 3 Baths
  • 2,164 Sq Ft

  Whitney Plan at Harvest at Ovation - Townhomes, Winter Garden, FL 34787

  Experience luxury living in this stunning new townhome by RockWell Homes, featuring 3 bedrooms, 3 bathrooms, loft and 2-car garage. With a covered lanai, charming front porch, and private covered balcony, this home is designed for both relaxation and entertaining. The chef’s kitchen is a highlight, featuring an island, upgraded solid surface flooring, and high-end stainless-steel appliances,

  RockWell Homes Builder

  14006 Scarlet Aster Aly Unit 40620799, Winter Garden, FL 34787
• 

  

  

  /22

  $212,000

  • 1 Bed
  • 1 Bath
  • 942 Sq Ft

  1315 Eastern Pecan Place Unit 202, Winter Garden, FL 34787

  Resort style living in Winter Garden close to everything. Enjoy an impressive array of resort-style community amenities, including a state-of-the-art fitness center, indoor basketball and racquetball courts, tennis courts, and a beautifully appointed clubhouse featuring a private movie theater and dedicated workspace. Relax by the resort-style swimming pool and spa, or entertain outdoors with a

  Steven Kwong CHARLES RUTENBERG REALTY ORLANDO

  1315 Eastern Pecan Place Unit 202, Winter Garden, FL 34787
• 

  

  

  /30

  $215,000

  • 2 Beds
  • 2 Baths
  • 1,265 Sq Ft

  14501 Grove Resort Ave Unit 3303, Winter Garden, FL 34787

  Experience the ultimate vacation lifestyle and investment opportunity at Grove Resort & Spa Orlando! This beautifully appointed 2-bedroom, 2-bath condo-hotel offers approximately 1,265 square feet of thoughtfully designed living space with an open-concept layout, stone countertops, stainless steel appliances, walk-in closet, in-unit laundry, private balcony, and elevator access. Fully furnished

  Juliana Fonseca de Andrade Dantas WRA BUSINESS & REAL ESTATE

  14501 Grove Resort Ave Unit 3303, Winter Garden, FL 34787
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  /42

  $229,900

  • 2 Beds
  • 1 Bath
  • 966 Sq Ft

  233 Southern Pecan Cir Unit 101, Winter Garden, FL 34787

  Beautifully refreshed and ready to move in today, this charming 2-bedroom, 1-bath corner condo offers an inviting combination of modern updates, natural light, and exceptional community amenities. The bright, crisp interior is filled with loads of natural light and features fresh paint throughout, brand-new carpet, new door handles, and stylish modern finishes. All appliances are included, making

  Scott Cohara KELLER WILLIAMS CLASSIC

  233 Southern Pecan Cir Unit 101, Winter Garden, FL 34787
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  /80

  $455,000

  Open Sat 3PM - 6PM

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

  15038 Windflower Aly, Winter Garden, FL 34787

  Discover an inviting 3-bedroom, 2.5-bath home in Winter Garden, offering a comfortable layout designed for both everyday living and entertaining. The main living areas create an open and welcoming environment, with natural light enhancing the sense of space and connecting the living, dining, and kitchen areas.Upstairs, the bedrooms are thoughtfully separated from the main gathering spaces,

  Fernanda Pereira NOVA REAL ESTATE SERVICES INC

  15038 Windflower Aly, Winter Garden, FL 34787
• 

  

  /55

  $489,000

  • 3 Beds
  • 2 Baths
  • 1,929 Sq Ft

  502 First Cape Coral Dr, Winter Garden, FL 34787

  WELCOME HOME TO BLACK LAKE PARK — a gated community where every day feels like a retreat. As you pass through the gates, you're welcomed by the community's stunning 10-acre park, complete with a charming white gazebo and wide-open green space that instantly sets the tone. There's a sense of warmth and connection here that's hard to put into words — you simply feel it. Pulling into the driveway

  Mario Archila PALM CIRCLE REALTY

  502 First Cape Coral Dr, Winter Garden, FL 34787
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  /30

  $425,000

  • 3 Beds
  • 2.5 Baths
  • 1,505 Sq Ft

  10108 Salt Point Dr, Winter Garden, FL 34787

  Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome located in the highly sought-after Waterleigh community in Winter Garden. Built in 2021, this move-in ready home features an open-concept floor plan with a spacious living area, a modern kitchen with stainless steel appliances, granite countertops, and a large island perfect for entertaining. Upstairs, the primary suite offers a

  Angela Mavarez Suarez PM ELITE REALTY LLC

  10108 Salt Point Dr, Winter Garden, FL 34787
• 

  

  /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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  /26

  $355,000

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,396 Sq Ft

  14501 Grove Resort Ave Unit 3619, Winter Garden, FL 34787

  WELCOME TO THIS BEAUTIFUL 3 BEDROOM / 2 BATHROOM JASMINE LUXURY FULLY FURNISHED CONDO AT THE GROVE RESORT & WATER PARK. THIS UNIT IS LOCATED IN ONE OF THE BEST AND MOST DESIRABLE POSITIONS IN THE ENTIRE RESORT, FEATURING DIRECT VIEWS OF THE WATER PARK AND THE LAKE, MAKING IT ONE OF THE MOST SOUGHT-AFTER UNITS. GROUND-FLOOR UNIT WITH EASY ACCESS TO THE PARKING AREA, PROVIDING VERY CONVENIENT

  Juan Buitrago, Sr REALTY ONE GROUP ESTATES

  14501 Grove Resort Ave Unit 3619, Winter Garden, FL 34787
• 

  /2

  $429,989

  New Construction $10K PRICE DROP

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

  13295 Peaceful Melody Dr, Winter Garden, FL 34787

  The Porter floorplan is an inviting two-story townhome designed with thoughtful spaces throughout. Featuring three bedrooms and two and a half 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

  Dream Finders Homes Builder

  13295 Peaceful Melody Dr, Winter Garden, FL 34787
• 

  

  /45

  $245,000

  $40K PRICE DROP

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

  14501 Grove Resort Ave Unit 1440, Winter Garden, FL 34787

  Seller is offering $5,000 toward the buyer’s closing costs, making this fully furnished condo at The Grove Resort & Water Park Orlando an even better opportunity for a vacation home, Airbnb-style investment, or personal getaway. Just minutes from Walt Disney World Resort and close to Universal Orlando Resort and SeaWorld Orlando, this 4th-floor condo-hotel unit offers peaceful fountain and

  Erica Diaz HOMEVEST REALTY

  14501 Grove Resort Ave Unit 1440, Winter Garden, FL 34787
• 

  

  /3

  $500,000

  $200K PRICE DROP

  • Land
  • 9.94 Acres
  • $50,302 per Acre

  12995 Reaves Rd, Winter Garden, FL 34787

  Vacant parcel (9.94 ac) with Residential/Agriculture zoning. Abundant foliage in a wetland setting. Obtaining permits is essential for assessing the conservation area before seeking a building permit. We highly recommend that prospective buyers engage the services of an environmental consultant to evaluate feasibility.

  12995 Reaves Rd, Winter Garden, FL 34787
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  /25

  $465,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,654 Sq Ft

  10089 Salt Point Dr, Winter Garden, FL 34787

  It can be negotiated along with the furniture.Welcome to this beautifully maintained 3-bedroom, 3-bathroom townhouse located in the highly desirable Waterleigh community. This modern home offers a functional and inviting open-concept layout, perfect for both everyday living and entertaining.The property features spacious bedrooms, well-appointed bathrooms, and a thoughtfully designed

  Nathalya Ferreira da Silva AUTHENTIC REAL ESTATE TEAM

  10089 Salt Point Dr, Winter Garden, FL 34787
• 

  

  /35

  $398,000

  $17K PRICE DROP

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

  14942 Windflower Aly, Winter Garden, FL 34787

  Step into this beautifully designed 3-bedroom, 2.5-bath townhome located in the highly desirable Osprey Ranch community in Horizon West. Built recently and featuring 1,536 sq ft, this home offers modern finishes, an open-concept layout, and a bright, spacious living area perfect for entertaining. The kitchen includes elegant cabinetry, quartz countertops, and stainless-steel appliances. Upstairs,

  Hugo Borges Ota Neto WRA BUSINESS & REAL ESTATE

  14942 Windflower Aly, Winter Garden, FL 34787
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  /5

  $299,000

  • Land
  • 4,791 Sq Ft
  • $2,718,182 per Acre

  0 9th St, Winter Garden, FL 34787

  Developer alert! Secure this rare residential lot that has plans for the construction of FOUR (4) RESIDENTIAL UNITS. Incredible opportunity to secure a multi-family development site complete with fully drafted architectural plans for a 4-unit building. Skip months of initial design work and the associated architectural expenses because these plans are completed and ready for submission to the

  Laura Senzamici ENGEL & VOELKERS LAKELAND

  0 9th St, Winter Garden, FL 34787
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  /18

  $459,000

  Pre-Foreclosure

  • 3 Beds
  • 2 Baths
  • 1,696 Sq Ft

  411 Millwood Place, Winter Garden, FL 34787

  Welcome to Covington Chase — one of Winter Garden's most sought-after communities! This charming 3BR/2BA/2-car garage home built in 2014 features an open great room layout, split bedrooms, and a 2-car garage. Enjoy community amenities including a pool, playground, and clubhouse, all just minutes from Historic Downtown Winter Garden, the West Orange Trail, Winter Garden Village shopping, and SR

  Kimberly Watson PEOPLE'S TRUST REALTY

  411 Millwood Place, Winter Garden, FL 34787
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  /43

  $491,080

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,881 Sq Ft

  15075 Groveside Rd, Winter Garden, FL 34787

  3 Level Townhome with 3 Bedrooms! Ready in August 2026! This new construction, three-story townhome (The Lantana) is a showstopper with its popular farmhouse exterior. This townhome features 3 bedrooms, 2 full bathrooms with a powder room, spanning 1,881 sq. ft. As you enter this home through the 8 ft. entry-door, you are welcomed by a Study room. As you continue up, you will find luxury vinyl

  DRB Homes Builder

  15075 Groveside Rd, Winter Garden, FL 34787
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  /29

  $440,000

  Open Thu 9AM - 7PM $45K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,998 Sq Ft

  5545 Bowman Dr, Winter Garden, FL 34787

  Come see 5545 Bowman Dr, recently updated with fresh interior paint and partial flooring replacement throughout. The kitchen features a backsplash and a convenient island providing additional workspace. The primary bedroom includes a spacious walk in closet, and the primary bathroom is equipped with double sinks for enhanced utility. Outside, a covered patio extends to a fully fenced in backyard,

  Karen Albright OPENDOOR BROKERAGE LLC

  5545 Bowman Dr, Winter Garden, FL 34787
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  /25

  $214,000

  $15K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 930 Sq Ft

  359 Douglas Way Unit 54, Winter Garden, FL 34787

  Short Sale. Don't miss this beautifully updated 2-bedroom, 2-bathroom townhouse offering the perfect blend of comfort, convenience, and unbeatable location. Tucked away in a quiet community, this home is just minutes from all the charm and excitement of downtown Winter Garden, known for its boutique shopping, top-rated restaurants, farmers market, splash pad, and the scenic West Orange

  Denise Pellegrino REAL BROKER, LLC

  359 Douglas Way Unit 54, Winter Garden, FL 34787
• 

  

  /19

  $444,990

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,652 Sq Ft

  Foxtail - Interior Unit Plan at Silverleaf Oaks - Townhome, Winter Garden, FL 34787

  The Foxtail offers maximum livability in this open-concept home design. Meals prepared for family and friends at the oversized kitchen island can be enjoyed in the bistro dining area or al fresco in the courtyard. Utilize one of the bedrooms as your dream home office, playroom, or guest suite.

  Pulte Homes Builder

  16808 Silverbrook Way Unit 41302658, Winter Garden, FL 34787
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  /45

  $418,500

  $1K PRICE DROP

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

  10648 Words Dr, Winter Garden, FL 34787

  Storey Grove **YES IT HAS A BACKYARD!!*BACKS TO GREENSPACE!!** 2023 built ** Open floorplan * Beautiful wood ceramic tile entire 1st floor ** Attractive tv wall wood accent inlay in the family room ** White kitchen cabinetry with quartz counters and large cooking island ** All bedrooms are on the 2nd floor ** Nice size +/-16x20 brick paver patio area and 2 car detached garage ** Great RING

  Gabriella Philippone INDEPENDENCE REALTY GROUP LLC

  10648 Words Dr, Winter Garden, FL 34787
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  /10

  $436,739

  New Construction

  • 2 Beds
  • 2 Baths
  • 1,515 Sq Ft

  11234 Silver Trumpet Loop, Winter Garden, FL 34787

  Welcome to the Caicos at 11234 Silver Trumpet Loop in Esplanade at McKinnon Groves! This charming new home offers a bright, open-concept layout that brings the kitchen, dining area, and great room together at the heart of the home. Sliding glass doors open to the covered lanai, extending the living space outdoors for relaxing mornings or evening gatherings. Tucked at the back, the primary suite

  Taylor Morrison Builder

  11234 Silver Trumpet Loop, Winter Garden, FL 34787
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  /2

  $480,000

  • 3 Beds
  • 3 Baths

  14501 Grove Resort Ave Unit 3626, Winter Garden, FL 34787

  Indulge in the ultimate resort-style lifestyle while seizing a remarkable investment opportunity with this exquisite condo at The Grove Resort & Water Park, Orlando's top-tier vacation haven. Condo w/ Pool and water park view. Just 5 min from Walt Disney World. Fully Furnished, turnkey residence. The primary suite creates an ideal atmosphere for relaxation. Open-concept layout is bathed in

  14501 Grove Resort Ave Unit 3626, Winter Garden, FL 34787
• 

  

  /3

  $299,900

  • Land
  • 1 Acre
  • $299,900 per Acre

  0 Arrowhead Blvd, Winter Garden, FL 34787

  1 acre of beautiful mature trees with a mixture of oaks and Cypress towards the lakefront. Utilities on site.Located on a spring fed lake. Ok for boats, skis, etc. Great school district. Ag zoning , ADU allowed (2nddwelling with restrictions) , paved road with easy access to commute. This is your slice of paradise you've beenwaiting for. Bring your own builder with NO HOA!!!

  Jaime Galeoto FLORIDA REALTY RESULTS LLC

  0 Arrowhead Blvd, Winter Garden, FL 34787
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  /6

  $443,190

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,683 Sq Ft

  6262 Sunny Time Ave, Winter Garden, FL 34787

  Beautiful 3 Bedroom, 2.5 Bathroom Dahlia Townhouse Complete Quartz Countertops & Tile Backsplash, Tile Flooring Throughout First Floor, Refrigerator, Washer, Dryer & Blinds!

  Pulte Homes Builder

  6262 Sunny Time Ave, Winter Garden, FL 34787
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  /40

  $275,000

  • 2 Beds
  • 2 Baths
  • 1,265 Sq Ft

  14501 Grove Resort Ave Unit 2532, Winter Garden, FL 34787

  ***Perfect for SNOWBIRDS!! Stay here all winter and let the onsite management company rent out your unit the rest of the year!! Beautiful and spacious fully-furnished fifth floor 2-bedroom condo located in The Grove Resort and Water Park! This condo easily sleeps six, with a screened in balcony for enjoying those evening sunsets! A full washer and dryer is located off the fully equipped kitchen,

  Lesley O'Neal FLARE PROPERTIES LLC

  14501 Grove Resort Ave Unit 2532, Winter Garden, FL 34787
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  /33

  $239,000

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

  14501 Grove Resort Ave Unit 1707, Winter Garden, FL 34787

  Exceptional opportunity to own a spacious top-floor 3-bedroom, 3-bathroom condo at The Grove Resort & Water Park, just minutes from Walt Disney World! This fully furnished 1,544 sq. ft. “Sable” floor plan offers an ideal combination of personal vacation use and income-producing potential through The Grove’s professionally managed hotel rental program. Located on the 7th and top floor of Building

  Uno Sorlie HOPKEY REALTY

  14501 Grove Resort Ave Unit 1707, Winter Garden, FL 34787
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  /15

  $342,000

  • 2 Beds
  • 1 Bath
  • 914 Sq Ft

  636 Coke Ave, Winter Garden, FL 34787

  Updated 2 Bedroom, 1 Bath Home Near Downtown Winter Garden. Welcome to your dream home! This beautifully updated 2-bedroom, 1-bath home is located just minutes from the heart of downtown Winter Garden, Florida. Property Highlights: Fully updated with brand-new cabinetry throughout the home, giving it a sleek, modern look. Stylish bathroom completely renovated with updated fixtures and finishes.

  Otto Solis VALSTAR REALTY LLC

  636 Coke Ave, Winter Garden, FL 34787
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  /40

  $260,000

  • 3 Beds
  • 2 Baths
  • 1,396 Sq Ft

  14501 Grove Resort Ave Unit 1728, Winter Garden, FL 34787

  ** WOW** A rare opportunity to purchase a 7th (top) floor condo at the beautiful Grove Resort and Water Park! This 3-bedroom, 2-bathroom, with sleeper sofa, comes fully furnished and ready to go! Perfect for SNOWBIRDS!! Stay here all winter and let the onsite management company rent out your unit the rest of the year!! Onsite management does all the work for you by obtaining bookings through

  Lesley O'Neal FLARE PROPERTIES LLC

  14501 Grove Resort Ave Unit 1728, Winter Garden, FL 34787
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  /35

  $284,995

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft

  431 Southern Pecan Cir Unit 101, Winter Garden, FL 34787

  ONE-YEAR HOME WARRANTY AVAILABLE WITH A FULL-PRICE OFFER! Welcome to this beautifully maintained 3-bedroom, 2-bathroom FIRST-FLOOR condo in the gated Southern Pines community of Winter Garden. Featuring a FRESH INTERIOR REPAINT (2026), UPDATED FIXTURES, a bright, open-concept layout, and NO CARPET THROUGHOUT FOR EASY MAINTENANCE, this home is truly move-in ready.Step inside to a spacious

  Nick Whitehouse RE/MAX PRIME PROPERTIES

  431 Southern Pecan Cir Unit 101, Winter Garden, FL 34787
• 

  

  /10

  $420,000

  New Construction

  • 2 Beds
  • 2 Baths
  • 1,515 Sq Ft

  11275 Silver Trumpet Loop, Winter Garden, FL 34787

  Welcome to the Caicos at 11275 Silver Trumpet Loop in Esplanade at McKinnon Groves! This welcoming new home showcases an airy open-concept design where the great room, kitchen, and dining area come together to create a seamless space for gathering and everyday living. Just beyond the great room, the covered lanai extends your living area outdoors. The private primary suite is tucked away at the

  Taylor Morrison Builder

  11275 Silver Trumpet Loop, Winter Garden, FL 34787
• 

  /2

  $435,000

  • 8 Beds
  • 3 Baths
  • 1,750 Sq Ft

  208 3rd St, Winter Garden, FL 34787

  8 bedrooms. 3 full baths. Approximately 1,750 SF. Just blocks from Plant Street.Space and location set this property apart. Offering 8 bedrooms and 3 full baths across approximately 1,750 SF, the home sits on a 9,431 SF fully fenced lot—a combination of interior space and land increasingly difficult to find this close to Historic Downtown Winter Garden.Built in 1925 and sold

  Ahmad Hassan COMPASS FLORIDA LLC

  208 3rd St, Winter Garden, FL 34787
• 

  

  /29

  $499,000

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

  12253 Bracco St, Winter Garden, FL 34787

  BRAND NEW CONSTRUCTION – NEVER LIVED IN – MOVE-IN READY!This is a rare opportunity to own a truly brand-new home that has never been occupied since the day it closed. No previous residents, no wear and tear, no surprises.Just a fresh start in a home that feels exactly as the builder intended.Be the very first person to live here, create memories here, and even peel the

  Gil Semedo LIFESTYLE INTERNATIONAL REALTY

  12253 Bracco St, Winter Garden, FL 34787
• 

  

  /14

  $204,900

  • 2 Beds
  • 2 Baths
  • 918 Sq Ft

  170 Windtree Ln, Winter Garden, FL 34787

  Great opportunity to own in the heart of Winter Garden! This beautifully updated 2-bedroom, 2-bath condo features a fully renovated kitchen, updated flooring throughout with NO carpet, and a functional open layout perfect for comfortable living or investment purposes. Conveniently located near shopping, dining, major roads, and just minutes from Winter Garden Village and Winter Garden Plaza.

  Romina Cabanas LA ROSA REALTY LLC

  170 Windtree Ln, Winter Garden, FL 34787
• 

  

  /24

  $445,000

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,665 Sq Ft

  3415 Stonegate Dr, Ocoee, FL 34761

  The Harper floorplan offers a 4-bedroom, 2-bathroom home with 1,665 sq ft of living space. Features include quartz and Revwood floors, an open layout, a spacious living room with natural light, a chef's kitchen with quartz countertops and stainless steel appliances, and a primary suite with a private ensuite bathroom. This all concrete block construction home also includes smart home technology

  Stephen Cline DR HORTON REALTY OF CENTRAL FLORIDA LLC

  3415 Stonegate Dr, Ocoee, FL 34761

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