Recently Sold Homes near Dillard Street Elementary

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  $575,000 Sold Sep 08, 2025

  • 1,960 Sq Ft
  • $293/SF
  • 5 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1979

  517 Garden Heights Dr, Winter Garden, FL 34787

  Welcome to 517 Garden Heights Drive — a fully renovated 4-bedroom, 2-bath modern farmhouse on a spacious 0.33-acre lot in the highly desirable golf cart district of Winter Garden. Just one mile from the vibrant Plant Street district and offering Lake Apopka views from the driveway, this home delivers the perfect blend of lifestyle and long-term value. Key updates include a brand-new roof

  Robert Frankenstein CHARLES RUTENBERG REALTY ORLANDO

  517 Garden Heights Dr, Winter Garden, FL 34787
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  Explore Dillard Street Elementary

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  $1,375,000 Sold Sep 05, 2025

  • 4,212 Sq Ft
  • $326/SF
  • 63 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2019

  108 Stanton Estates Cir, Winter Garden, FL 34787

  Welcome to 108 Stanton Estates Circle, a beautifully crafted 4-bedroom, 4-bath pool home offering over 4,200 square feet of refined living in the heart of one of Winter Garden’s most charming communities. Located in Stanton Estates, a quiet neighborhood of fewer than 50 homes, this property sits just one block from the West Orange Trail and within Winter Garden’s golf cart district, offering

  Silvia Kinkela SERHANT

  108 Stanton Estates Cir, Winter Garden, FL 34787
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  $430,000 Sold Sep 04, 2025

  • 1,352 Sq Ft
  • $318/SF
  • 133 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1946

  335 W Bay St, Winter Garden, FL 34787

  LOCATION-LOCATION-LOCATION~REDUCED PRICE TO SELL~NO HOA~DOWNTOWN WINTER GARDEN HOME READY FOR A AUGUST MOVE IN!~ONE BLOCK NORTH OF PLANT STREET~STEPS AWAY FROM THE CROOKED CAN, THE MARKET PLACE, DINING AND LIVE ENTERTAINMENT WEEKLY~ HISTORIC WINTER GARDEN HOME IN GOLF CART DISTRICT~PARKING IN THE BACK OF THE HOUSE WITH PAVER DRIVEWAY ~ CORNER LOT BEAUTIFULLY MANICURED LUSH LANDSCAPING~ RENOVATED

  Christy Clark-Weber SOUTHERN HERITAGE REALTY, INC

  335 W Bay St, Winter Garden, FL 34787
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  $203,000 Sold Aug 29, 2025

  • 1,094 Sq Ft
  • $186/SF
  • 56 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1961

  1170 E Bay St, Winter Garden, FL 34787

  Super Rare Opportunity at a Super Rare price in Winter Garden! Don't miss out on this 3 bedroom home with a brand new HVAC 2024, laminate flooring throughout with the exception of the bonus room. Natural gas range, Updated bathroom, updated electrical panel and more! Bonus room can be used for a multitude of purposes. Exterior features a shed, extra long driveway and NO HOA! A short distance

  Carmen Aridas RE/MAX PRIME PROPERTIES

  1170 E Bay St, Winter Garden, FL 34787
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  $500,000 Sold Aug 29, 2025

  • 3,009 Sq Ft
  • $166/SF
  • 137 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2007

  519 Hearthglen Blvd, Winter Garden, FL 34787

  Welcome to this stunning 4-bedroom , 3 bathroom home in the heart of Winter Garden's Golf Cart District! Perfectly situated near top rated schools, the West Orange Trail, and the vibrant downtown scene, you'll enjoy easy access to boutique shopping, award-winning dining and local favorites like The Crooked Can Brewery.Step inside to discover a spacious thoughtfully designed layout with modern

  Lauren Graham COLDWELL BANKER HUBBARD HANSEN

  519 Hearthglen Blvd, Winter Garden, FL 34787
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  /2

  $441,500 Sold Aug 26, 2025

  • 1,785 Sq Ft
  • $247/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1991

  1534 E Spring Ridge Cir, Winter Garden, FL 34787

  One or more photo(s) has been virtually staged. Rare Opportunity in Winter Garden’s Golf Cart District with a 85 foot wide lot and low HOA fees!Located in sought-after Crown Point Springs, this 3-bedroom, 2-bathroom home sits on a .23-acre oversized lot just minutes from vibrant Historic Downtown Winter Garden, West Orange Trail (.5 miles), Chaplin Station where you can enjoy the picnic

  Sharon Brandt KELLER WILLIAMS REALTY AT THE LAKES

  1534 E Spring Ridge Cir, Winter Garden, FL 34787
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  /2

  $950,000 Sold Aug 25, 2025

  • 2,432 Sq Ft
  • $391/SF
  • 78 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2019

  141 S Park Ave, Winter Garden, FL 34787

  Live in DT Winter Garden where vibes run high. This townhome is in the heart of Downtown Winter Garden, literally steps from the Crooked Can Brewery, Market to Table, and the farmers market every Saturday. This 3-story home features high-end details, quality finishes that you would expect in a custom home, and a private elevator. The main floor showcases the gourmet kitchen, dining space with

  Mauro Costa CORCORAN PREMIER REALTY

  141 S Park Ave, Winter Garden, FL 34787
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  /2

  $154,000 Sold Aug 22, 2025

  • 910 Sq Ft
  • $169/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1961

  1065 Lincoln Terrace, Winter Garden, FL 34787

  This is a fantastic fixer-upper opportunity for investors or homeowners seeking a project in a prime Winter Garden location. Just 5 minutes from the charming Downtown Winter Garden and conveniently close to major routes like SR-429, this property offers immense potential. The home is being sold as-is and requires a complete rehab, allowing you to fully customize it to your vision. It features a

  Bobby Baldor EXP REALTY LLC

  1065 Lincoln Terrace, Winter Garden, FL 34787
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  $500,000 Sold Aug 22, 2025

  • 1,324 Sq Ft
  • $378/SF
  • 78 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  375 N Boyd St, Winter Garden, FL 34787

  Step into a piece of mid-century magic just blocks from the heart of Plant Street and the shimmering shoreline of Lake Apopka! This beautifully maintained home welcomes you with incredible curb appeal—lush FLORIDA NATIVE landscaping, a charming courtyard, and a manicured lawn that perfectly frames this classic beauty.Inside, this single-level home exudes character, with original terrazzo

  Chad Williams OLYMPUS EXECUTIVE REALTY INC

  375 N Boyd St, Winter Garden, FL 34787
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  /2

  $585,000 Sold Aug 21, 2025

  • 1,966 Sq Ft
  • $298/SF
  • 37 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1979

  704 Tangerine Ct, Winter Garden, FL 34787

  Welcome to Your Dream Home – Where Style, Space, and Location Come Together!Tucked away at the end of a peaceful cul-de-sac, this exceptional home sits on an oversized lot—nearly half an acre—and offers the perfect blend of upgraded interior living and unmatched outdoor space. Best of all, you’re just minutes from vibrant Historic Downtown Winter Garden, where you’ll enjoy an array of

  Karen Jacobs COLDWELL BANKER RESIDENTIAL RE

  704 Tangerine Ct, Winter Garden, FL 34787
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  /2

  $505,000 Sold Aug 21, 2025

  • 1,342 Sq Ft
  • $376/SF
  • 80 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1921

  112 N Lakeview Ave, Winter Garden, FL 34787

  Step into timeless charm with this beautifully preserved 2-bedroom, 1-bathroom historic 1920s home on 0.3 acres of land, nestled in the heart of downtown Winter Garden. Inside, original architectural details and vintage character create a warm and inviting atmosphere, while the thoughtfully maintained layout offers 1,364 sq ft of comfortable living space. Large windows flood the home with natural

  Kurtis Gunter DENIZ REALTY PARTNERS LLC

  112 N Lakeview Ave, Winter Garden, FL 34787
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  $640,000 Sold Aug 15, 2025

  • 2,756 Sq Ft
  • $232/SF
  • 9 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2014

  724 Grassy Stone Dr, Winter Garden, FL 34787

  This stunning 4-bedroom, 3-bathroom home in the sought-after Winter Garden neighborhood offers a perfect combination of modern upgrades and timeless charm. Situated on a spacious 0.29-acre lot in a peaceful cul-de-sac, this home provides both tranquility and convenience. A BRAND NEW ROOF, NEW GUTTERS and a NEW WATER HEATER ensure that this home is move-in ready and worry-free for years to

  Alex Medal ERA GRIZZARD REAL ESTATE

  724 Grassy Stone Dr, Winter Garden, FL 34787
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  $565,000 Sold Aug 08, 2025

  • 1,754 Sq Ft
  • $322/SF
  • 2 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2001

  101 Traditions Dr, Winter Garden, FL 34787

  Welcome to 101 Traditions Drive—your charming slice of Winter Garden living just minutes from Historic Plant Street! This beautifully maintained 4-bedroom, 2-bathroom home offers the perfect blend of comfort, convenience, and value. Step inside to discover an open-concept living space with updated kitchen and bathrooms, ideal for both everyday living and entertaining. The spacious kitchen

  Jacky Herrera COMPASS FLORIDA LLC

  101 Traditions Dr, Winter Garden, FL 34787
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  /2

  $530,000 Sold Aug 01, 2025

  • 1,581 Sq Ft
  • $335/SF
  • 102 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1985

  1022 Glenharbor Cir, Winter Garden, FL 34787

  This beautifully renovated 4-bedroom, 2-bathroom home perfectly combines a modern aesthetic with a charming, welcomingfeel. Situated in Winter Garden in a golf cart approved zone and no HOA! The open floor plan is filled with natural light, showcasing bright light walls and flooring that are thoughtfully balanced by dark hardware and accent details, creating an updated yet cozy atmosphere.

  Cheyanne MacNeill THE AGENCY ORLANDO

  1022 Glenharbor Cir, Winter Garden, FL 34787
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  /2

  $490,000 Sold Jul 31, 2025

  • 1,738 Sq Ft
  • $282/SF
  • 32 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1925

  206 N Highland Ave, Winter Garden, FL 34787

  Historic Craftsman in the highly desired Golf Cart zone of Downtown Winter Garden. Property has great bones but is in need of some updates. Perfect property for investors or buyers looking to design there dream home. House does have a New Roof 2024 and the AC is 2017. This is a rare opportunity with endless possibilities.

  Danielle Galloway CFL REALTY PROS LLC

  206 N Highland Ave, Winter Garden, FL 34787
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  $429,900 Sold Jul 30, 2025

  • 1,693 Sq Ft
  • $254/SF
  • 14 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1981

  525 Garden Heights Dr, Winter Garden, FL 34787

  This well-maintained home features a split-bedroom design with comfortable living spaces and a practical floor plan that offers a versatile layout ready for daily living and any occasion. This property welcomes you with its warm curb appeal, featuring a stone and wood paneling exterior, with mature trees and no rear neighbors enhancing this peaceful escape. The home features a spacious living

  Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

  525 Garden Heights Dr, Winter Garden, FL 34787
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  /2

  $735,000 Sold Jul 30, 2025

  • 2,652 Sq Ft
  • $277/SF
  • 14 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1973

  708 Valencia Ct, Winter Garden, FL 34787

  Location. Location. Location! Sitting on a lush .36-acre lot framed by majestic oak trees and located in Valencia Shores—where golf carts are a way of life—you’re just a short stroll from historic downtown Winter Garden, the vibrant Farmers Market, Lakeview Middle School, and the West Orange Trail!Pride of ownership shows with this impeccably maintained and spacious home. Enter to an

  Dallas Ackley COMPASS FLORIDA LLC

  708 Valencia Ct, Winter Garden, FL 34787
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  $700,000 Sold Jul 18, 2025

  • 2,225 Sq Ft
  • $315/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1923

  40 W Smith St, Winter Garden, FL 34787

  Step into a piece of Winter Garden's rich history with this captivating, charming historic home in the "golf district" in the heart of downtown Winter Garden. Nestled in the heart of downtown Winter Garden, enjoy easy access to the widely popular Plant Street farmer's market, West Orange Trail, and the famed Crooked Can Brewery. This prime location home is nestles in the heart of

  Tuan Trinh NATIONAL REAL ESTATE LLC

  40 W Smith St, Winter Garden, FL 34787
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  /2

  $520,000 Sold Jul 18, 2025

  • 2,011 Sq Ft
  • $259/SF
  • 195 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2024

  5015 Railroad Vine Alley, Winter Garden, FL 34787

  Under Construction. Brand new, energy-efficient home available NOW! Enjoy the functionality of the open designer curated kitchen, spacious great room and dining area. Flex space can be configured as a home office, hobby space, or play area for kids. Now selling from the mid $500's, Silverleaf Reserve offers spacious open floorplan concepts fit for every lifestyle. Located in the heart of Winter

  Tatiana Souza MERITAGE HOMES OF FL REALTY

  5015 Railroad Vine Alley, Winter Garden, FL 34787
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  /2

  $1,000,000 Sold Jul 18, 2025

  • 2,938 Sq Ft
  • $340/SF
  • 333 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2019

  137 S Park Ave, Winter Garden, FL 34787

  Welcome to your dream home in the heart of downtown Winter Garden! This stunning 3-story townhome offers an expansive 2,938 sq ft of living space, featuring 3 bedrooms and 3.5 bathrooms, one of the few larger floor plans in the community. This home includes a bonus golf cart garage in addition to a full-size 2-car garage, perfect for enjoying all the perks of the Golf Cart District without

  Michelle Baron DENIZ REALTY PARTNERS LLC

  137 S Park Ave, Winter Garden, FL 34787
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  /2

  $725,000 Sold Jul 14, 2025

  • 2,475 Sq Ft
  • $293/SF
  • 30 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2012

  721 Lake Cove Pointe Cir, Winter Garden, FL 34787

  721 Lake Cove Pointe Circle is a spectacular house in an incredible location. As you enter this highly coveted tucked away gated development, you will notice a community of well-manicured lawns and beautifully maintained houses. When you drive up to the front of 721 Lake Cove Pointe Circle, your eyes will be drawn to the well landscaped lot with mature trees and a 3-car garage with a wide

  Marysue Hartman COLDWELL BANKER REALTY

  721 Lake Cove Pointe Cir, Winter Garden, FL 34787
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  $540,000 Sold Jul 07, 2025

  • 1,680 Sq Ft
  • $321/SF
  • 47 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1986

  1013 Glensprings Ave, Winter Garden, FL 34787

  Discover the Heart of Winter Garden Living. Welcome to this 3-bedroom, 2-bath home tucked away in a GOLF CART APPROVED neighborhood with NO HOA or CDD fees, a rare and exciting opportunity in Winter Garden! From the inviting front porch to the beautifully landscaped yard, this home feels warm, welcoming, and ready for you to make it your own. Step inside to find brand new laminate flooring

  Jenny Ramirez COLDWELL BANKER REALTY

  1013 Glensprings Ave, Winter Garden, FL 34787
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  /2

  $711,000 Sold Jul 03, 2025

  • 2,484 Sq Ft
  • $286/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1997

  432 Valley View Dr, Winter Garden, FL 34787

  Welcome to this beautifully spacious 3-bedroom, 2-bathroom home with 2,484 square feet of living space, located in the highly sought-after Golf Cart District of historic downtown Winter Garden! Enjoy the unique lifestyle that comes with being just minutes from charming shops, dining, farmers markets, and vibrant community events—all easily accessible by golf cart or on foot. The screened patio

  Ryan Langley FLORIDA REALTY INVESTMENTS

  432 Valley View Dr, Winter Garden, FL 34787
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  $611,000 Sold Jul 03, 2025

  • 2,007 Sq Ft
  • $304/SF
  • 31 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1993

  1667 Spring Loop Way, Winter Garden, FL 34787

  Charming, Fully Remodeled Home in Downtown Winter Garden’s Golf Cart District! Welcome to the cutest home in downtown Winter Garden! This completely remodeled 4-bedroom, 2-bath beauty is packed with nearly $200,000 in upgrades, making it the perfect blend of modern luxury and small-town charm. Step inside and be wowed by designer finishes, including elegant champagne gold accents that add warmth

  Erica Diaz HOMEVEST REALTY

  1667 Spring Loop Way, Winter Garden, FL 34787
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  $499,000 Sold Jun 20, 2025

  • 1,783 Sq Ft
  • $280/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  1663 Markel Dr, Winter Garden, FL 34787

  Welcome to your dream home in beautiful Winter Garden! Nestled on just over half an acre, this charming 3-bedroom, 2-bath home offers the perfect blend of comfort, space, and character. Step inside to find a bright and open floor plan, highlighted by a cozy fireplace — perfect for relaxing evenings. A spacious, enclosed Florida room extends your living space and offers year-round enjoyment with

  Jorge Coello DENIZ REALTY PARTNERS LLC

  1663 Markel Dr, Winter Garden, FL 34787
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  /2

  $805,000 Sold Jun 19, 2025

  • 4,700 Sq Ft
  • $171/SF
  • 138 Days On Market

  • 7 Beds
  • 4 Baths
  • Built 2018

  1713 Fullers Oak Loop, Winter Garden, FL 34787

  Welcome to an exquisite 7-bedroom, 4-bathroom luxury estate nestled in the highly sought-after Winter Garden community. Spanning an impressive 4,700 square feet of refined living space, this meticulously crafted 2018 residence offers the perfect blend of elegance, comfort, and modern convenience. Situated on a generous 10,191 square foot lot, this home is designed for both grand entertaining and

  Omi Jean Louis LIFESTYLE INTERNATIONAL REALTY

  1713 Fullers Oak Loop, Winter Garden, FL 34787
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  $520,000 Sold Jun 12, 2025

  • 1,850 Sq Ft
  • $281/SF
  • 18 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2018

  644 Orange Belt Loop, Winter Garden, FL 34787

  DOWNTOWN WINTER GARDEN END UNIT TOWNHOME...Welcome to this beautifully maintained end-unit townhome located in the highly sought-after golf cart district of Winter Garden. Boasting 3 bedrooms, 2.5 bathrooms, and an open-concept layout, this home is perfect for both relaxation and entertaining. The spacious living and dining areas are flooded with natural light, creating a warm and inviting

  Keith Packey RE/MAX TITANIUM GROUP

  644 Orange Belt Loop, Winter Garden, FL 34787
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  $1,250,000 Sold Jun 09, 2025

  • 3,170 Sq Ft
  • $394/SF
  • 4 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2019

  240 Stanton Estates Cir, Winter Garden, FL 34787

  Newly listed in historic downtown Winter Garden! Just a short golf cart ride or walk to Plant Street, the Crooked Can Brewery and the West Orange Trail!! Simply magnificent outdoor living spaces, with a private saltwater pool, an outdoor kitchen and fully fenced for your comfort and relaxation. Recently built in 2019, this one-story multigenerational home has four bedrooms and four full

  Joseph Thomas, Jr FATHOM REALTY FL LLC

  240 Stanton Estates Cir, Winter Garden, FL 34787
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  /2

  $483,000 Sold Jun 09, 2025

  • 1,781 Sq Ft
  • $271/SF
  • 71 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1964

  427 N Lakeview Ave, Winter Garden, FL 34787

  *** BACK-UP OFFERS are strongly encouraged. Inquire today! *** Charming POOL home with a fenced-in backyard oasis just footsteps from historic downtown WINTER GARDEN! This beautiful retreat with NO HOA sits on a QUARTER of an acre and features 4-bedrooms, 2-baths, a dining space that opens to a family room, a 13 X 22 living room, a laundry room with ample storage, a generously sized screened-in

  Ashley Boyd BHHS FLORIDA REALTY

  427 N Lakeview Ave, Winter Garden, FL 34787
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  $260,000 Sold Jun 02, 2025

  • 1,566 Sq Ft
  • $166/SF
  • 86 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1957

  608 S Lakeview Ave, Winter Garden, FL 34787

  Are investment properties hard to find? No more excuses! Are you considering a fix and flip project? ONLY CASH, ONLY CASH, NO IS FORECLOSURE, IS URGENT.... It's time to get to work! This opportunity is perfect for first-time investors or those looking for a sweat equity starter home. This is a true "handyman special": The property requires major renovations. Includes an incomplete bathroom. If

  Romelia Pina De Pina DELUX ROYAL REAL ESTATE, LLC

  608 S Lakeview Ave, Winter Garden, FL 34787
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  $260,000 Sold May 30, 2025

  • 880 Sq Ft
  • $295/SF
  • 3 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1952

  232 W Lafayette St, Winter Garden, FL 34787

  Charming DOWNTOWN WINTER GARDEN home with R-2 zoning! Move in ready 2-bedroom, 2-bath home, ideally situated near Winter Garden’s vibrant Plant Street. Nestled just minutes from the heart of downtown Winter Garden, this home allows easy access to the area’s renowned shopping, dining, and entertainment. An updated kitchen with Quartz countertop, new appliances, stylish vinyl flooring. NO HOA. Roof

  Trung Nguyen LA ROSA REALTY LLC

  232 W Lafayette St, Winter Garden, FL 34787
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  /2

  $210,000 Sold May 28, 2025

  • 814 Sq Ft
  • $258/SF
  • 29 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1961

  1130 E Bay St, Winter Garden, FL 34787

  A Home of Warmth and Light - A hidden gem, so full of cheer, A place to love, to hold so dear. Three bright rooms, a bath with grace,A charming, peaceful living space. Built with care in days gone by, Where sunsets paint the open sky. A tranquil lot, both wide and fair,With memories waiting to grow and share. Close to shops and schools so near, Highways, roads, and places dear. Near the shops and

  Reuben Simmonds, Jr BLAIR REALTY GROUP INC

  1130 E Bay St, Winter Garden, FL 34787
• 

  /2

  $687,500 Sold May 27, 2025

  • 2,758 Sq Ft
  • $249/SF
  • 3 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2020

  677 Brooks Field Dr, Winter Garden, FL 34787

  MULTIPLE OFFERS...all highest & best offers are due by Sunday 4/20/25 at 5 pm. FINALLY there is an available gorgeous home in the sought after McAllister Landing community of Winter Garden!! Move right in and do nothing but take a dip in your very own new salt water pebble textured heated POOL. Although that heat won't be needed any day now! This community is situated in a prime location just

  Randall Kain LPT REALTY, LLC

  677 Brooks Field Dr, Winter Garden, FL 34787
• 

  /2

  $515,000 Sold May 21, 2025

  • 1,850 Sq Ft
  • $278/SF
  • 67 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2019

  696 Orange Belt Loop, Winter Garden, FL 34787

  New Price! ”Modern Living in the Heart of downtown Winter Garden!! Welcome to this stunning 3-bedroom, 2.5-bath end-unit townhome, perfectly located in Winter Garden’s sought-after golf cart district. Just steps from the West Orange Trail and vibrant Downtown Winter Garden, this home combines contemporary comfort with the charm of a historic small-town lifestyle.Step inside to discover natural

  Vi Mateo KELLER WILLIAMS WINTER PARK

  696 Orange Belt Loop, Winter Garden, FL 34787
• 

  /2

  $489,900 Sold May 19, 2025

  • 1,385 Sq Ft
  • $354/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  560 Garden Heights Dr, Winter Garden, FL 34787

  Step into a home that feels brand new — but better. Tastefully updated with bespoke finishes and thoughtful upgrades throughout, this residence blends comfort and elegance in all the right ways. From the moment you enter, you’re greeted by an open, airy layout with vaulted ceilings, rich wood-toned LVP floors, and a spacious great room perfect for entertaining or everyday living.The kitchen is a

  Ahmad Hassan COMPASS FLORIDA LLC

  560 Garden Heights Dr, Winter Garden, FL 34787
• 

  /2

  $1,000,000 Sold May 09, 2025

  • 3,352 Sq Ft
  • $298/SF
  • 155 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2020

  501 N Dillard St, Winter Garden, FL 34787

  Welcome to this stunning 4-bedroom, 3.5-bathroom residence that beautifully blends classic charm with modern luxury. Built in 2020 and nestled in the heart of Winter Garden, this home offers spacious living and impeccable attention to detail. Step inside to discover an open-concept layout featuring a chef’s kitchen, complete with high-end appliances, custom cabinetry, and a large center island.

  Alexis Anderson REGENCY REAL ESTATE LLC

  501 N Dillard St, Winter Garden, FL 34787
• 

  /2

  $510,000 Sold May 05, 2025

  • 1,500 Sq Ft
  • $340/SF
  • 75 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1958

  213 James Dr, Winter Garden, FL 34787

  Great Opportunity to Own a wonderful home in FULLY RENOVATED HOME IN GOLF DISTRICT PLAN STEET WINTER GARDEN with 3 bedroom 2 Full Bathrooms and 1500 square foot Home built in 1958 and revamped in 2024. This property sits on 0.25 (quarter acre) minutes from the highly desired plant street bars and restaurant area. The owners did an amazing job of fully remodeling the entire property and

  Milton James COLDWELL BANKER RESIDENTIAL RE

  213 James Dr, Winter Garden, FL 34787
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  $475,000 Sold Apr 30, 2025

  • 1,606 Sq Ft
  • $296/SF
  • 5 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2010

  636 Bainbridge Loop, Winter Garden, FL 34787

  MULTIPLE OFFERS - DEADLINE 3/10 AT 5PM. THE WINTER GARDEN HAVEN // Come see this charming single-story, 4 bedroom, 2 bathroom home in the sought-after Winter Garden neighborhood of Covington Chase. You'll immediately appreciate the curb appeal – a blend of neutral stucco and stone accents that gives it a warm, inviting look. Inside, you'll find a thoughtfully updated space designed for

  Kristina Mollo ALL REAL ESTATE & INVESTMENTS

  636 Bainbridge Loop, Winter Garden, FL 34787
• 

  /2

  $1,450,000 Sold Apr 30, 2025

  • 3,267 Sq Ft
  • $444/SF
  • 10 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1920

  234 N Lakeview Ave, Winter Garden, FL 34787

  Nestled in the heart of downtown Winter Garden, "The Birdhouse" invites you into a world where history meets luxury. This stunning 1920 historic home blends vintage charm with modern elegance. As you walk through the entrance, you're welcomed by the unique character of brick walls, wood beams, and a tongue and groove ceiling. The main house features three bedrooms and three baths, spread across

  Matt McKee COMPASS FLORIDA LLC

  234 N Lakeview Ave, Winter Garden, FL 34787
• 

  /2

  $555,000 Sold Apr 30, 2025

  • 1,797 Sq Ft
  • $309/SF
  • 177 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  704 Tangelo Ct, Winter Garden, FL 34787

  One or more photo(s) has been virtually staged. Welcome to this beautifully upgraded 3-bed, 2-bath ranch-style home. BRAND NEW AC (2024), ROOF 2018. Ideally located on a cul-de-sac in the heart of historic downtown Winter Garden's golf cart district. This charming one-story residence offers 1,797 sq. ft. of living space, 3,136 gross sq. ft. on nearly HALF AN ACRE. The home boasts an open floor

  Christian Dyas THE REAL ESTATE COLLECTION LLC

  704 Tangelo Ct, Winter Garden, FL 34787

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