Winter Garden Real Estate Search

Winter Garden Homes for Sale

Home to roughly forty thousand people, the cozy community of Winter Garden, Florida, has a spectacular location just fifteen miles from the excitement of Orlando. While providing easy access to an extensive list of big-city attractions, Winter Garden also offers a relaxed, laid-back atmosphere and an escape from the hustle, bustle, and traffic of the Metro Area. The community has a lovely downtown area that is listed on the National Register of Historic Places and offers a variety of retail shops, restaurants, cafes, as well as a few museums and a theater. Similarly, Winter Garden is home to Crooked Can Brewery.

Winter Garden is also a place with abundant natural beauty that can be enjoyed in multiple local parks, like Lake Brim Park, Chapin Station, and Oakland Nature Preserve. Collectively, these and the other area recreation destinations offer picnic areas, playgrounds, open green spaces, biking and hiking paths, and a variety of sports courts. Homes in Winter Garden also offer proximity to several major transportation routes, including County Road 545, County Road 535, and the Western Beltway.

Winter Garden real estate is just as desirable and diverse as the Metro’s amenities. Homes for sale in Winter Garden include a collection of lower-maintenance homes, like townhouses, apartments, and condos. Real estate in Winter Garden also includes a vast array of detached single-family houses of many styles, floor plans, ages, and sizes. This means you can find both new construction and historic homes in Winter Garden in Modern, Mediterranean, Traditional, and other architectural designs. For specific details about available properties in Winter Garden, Florida, please connect with us today, and we will happily help you with your Winter Garden home search.

Our website features the best Winter Garden real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

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Newest Winter Garden Homes and Condos for Sale

$630,000
4 Beds ⋅ 3 Baths ⋅ Hawksmoor Ph 2 SubDv. ⋅ 34787 Zip Code
Hawksmoor ** Beautiful 2020 built upgraded home with 4 bedrooms and 3 baths ** Espresso kit cabinets, tile backsplash, granite counters plus a walk in pantry ** All kitchen stainless steel appliances are included ** Beautiful plank tile floors in the main rooms and newer laminate flooring in the downstairs 4th bedroom and master bedroom ** First floor 4th bedroom or den or play area with a closet - your choice ** New upgraded lighting fixtures, newer Smart switches and newer ceiling fans in the living room, bedrooms, loft and lanai ** Lovely newer plantation shutters on the kitchen and family room windows ** Upgraded front exterior door with privacy glass and Ring doorbell ** Easy accessible 2nd floor laundry ** 14x12' loft area perfect for a game room or work area ** Covered screened lanai plus a front covered patio ** Upgraded landscaping ** Convenient permanent holiday lighting (Trim Lighting) and permanently installed accent lights (down lighting) upgrades that are controlled via app and can be programmed to different colors ** 2 car attached garage ** Great neighborhood amenities including a resort style zero entry community pool, a kids splash pad, clubhouse with fitness center, tot lot playground, a shaded pavilion, walking trails and green park areas *** Newer storage "Smart Racks” in the garage convey. All room measurements are approximate and from builder floor plan. Orange County Appraiser records are incorrect states 3/2.5 but home is actually 4 bedrooms and 3 full bath. Buyer to verify all room measurements.

16286 Taliesin Street, Winter Garden
$57,777
Loveless J S Add 01 SubDv. ⋅ 34787 Zip Code
.0.10 acre lot !!! R-NC-2 -This zoning designation- Winter Garden rates as one of the best places to live, work and visit in Florida and has a school system with above average ratings. It is approximately 20 minutes west of Orlando and is listed on the National Registry of Historic Places. The thriving business district continues to be a favored destination for locals and tourists alike. Among the many notable places to visit include the award-winning West Orange Trail, the nationally recognized weekly Farmers Market, the Garden Theater or the Soho Gallery and Art Center:

764 Klondike Street, Winter Garden
$794,000
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 2a SubDv. ⋅ 34787 Zip Code
This beautiful one-story "Bellmore" home features 4 bedrooms and 3 full bathrooms. The foyer, hallway, drop zone, kitchen, family room, and dining room feature a beautiful wooden siding throughout as well as crown molding. The master bedroom features a coffered ceiling. There is back splash on the kitchen wall. A wi-fi SONOS sound system is connected and includes speakers in bedroom 2 and the family room. Gutters, wired mood lighting installed under and above kitchen cabinet, walls with rounded corners, a security system, and tiles positioned in a staggered layout (installed in ALL common areas and bathrooms). APPLIANCES: Included in the price are stainless steel range, stove and conventional oven, microwave, dishwasher, and fridge, washer and dryer. The garage also includes two overhead storage spaces. The community features a great amenities, including a large pool, a 24-hour gym, tennis courts, a public dock, a clubhouse, large open spaces, playground and dog park. The home is located steps away from the clubhouse and a future shopping plaza that will include a Publix supermarket and is just a short drive away from all that Orlando has to offer! The all-new Flamingo Crossings shopping plaza is located approximately 7 minutes away. The property is conveniently located close to SR 429, which connects to I-4 and the Turnpike.

10386 Atwater Bay Drive, Winter Garden
$69,999
34787 Zip Code
Go direct. Call or text the listing agent to help explain how the lots sit. This is a group of 3 lots for sale; they can all be purchased or sold individually. They're side by side. The lots have canal access to Lake Apopka. They will need to be cleaned out due to the overgrowth. Right off of highway 50 just minutes to the turnpike onramp for quick access anywhere in the Orlando area. Tax ID 19 22 27 0000 00 043 is first on the left, middle Lot is Tax ID 19 22 27 0000 00 052 and the final lot that butts up to the neighbors property at the end of the street is Tax ID 19 22 27 0000 00 072.

Killarney Cove Drive, Winter Garden
$69,999
34787 Zip Code
Go direct. Call or text the listing agent to help explain how the lots sit. This is a group of 3 lots for sale; they can all be purchased or sold individually. They're side by side. The lots have canal access to Lake Apopka. They will need to be cleaned out due to the overgrowth. Right off of highway 50 just minutes to the turnpike onramp for quick access anywhere in the Orlando area. Tax ID 19 22 27 0000 00 043 is first on the left, middle Lot is Tax ID 19 22 27 0000 00 052 and the final lot that butts up to the neighbors property at the end of the street is Tax ID 19 22 27 0000 00 072.

Killarney Cove Drive, Winter Garden
$69,999
34787 Zip Code
Go direct. Call or text the listing agent to help explain how the lots sit. This is a group of 3 lots for sale; they can all be purchased or sold individually. They're side by side. The lots have canal access to Lake Apopka. They will need to be cleaned out due to the overgrowth. Right off of highway 50 just minutes to the turnpike onramp for quick access anywhere in the Orlando area. Tax ID 19 22 27 0000 00 043 is first on the left, middle Lot is Tax ID 19 22 27 0000 00 052 and the final lot that butts up to the neighbors property at the end of the street is Tax ID 19 22 27 0000 00 072.

Killarney Cove Drive, Winter Garden
$549,990
3 Beds ⋅ 2.5 Baths ⋅ Summerlake Pd Ph 3b SubDv. ⋅ 34787 Zip Code
This STUNNING well-kept home is located in the heart of Horizon West. At the most desired Community in central Florida. Don't waste your weekend and money doing yard work, when you can be relaxing at the resort style amenity center!! With a close commute to amazing food and restaurants, Cinepolis movie theater and Publix. You cannot miss with this location. As you wander downstairs, you'll be greeted with an amazing floor plan, with a master bedroom and a jack'n Jill on the second floor and all the common area at the first. Summerlake has second to none community features such as great views of the fireworks at Disney World and the HOA includes lawn & yard service and resort-style amenities, such as a large swimming pool w/ lap lanes and water features, a basketball court, zip line, tennis courts, fitness center, clubhouse, dog park, playgrounds, fishing pier, various walking trails, and sports fields. Top rated schools are close by, the 429, shopping, outstanding restaurants, and Publix are minutes away, and Disney is only 10 minutes away. This Winter Garden home is a can't miss opportunity!! Make it yours today!

15077 Purple Martin Street, Winter Garden
$699,000
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 1c SubDv. ⋅ 34787 Zip Code
Beautiful single story home and highly popular Bellmore floor plan! Oversized and Private lot with Water views on each side. This impeccable home includes 4 bedrooms , 3 full bathrooms with 2,113 sq ft. and all the premier upgrades imagined. Upon entry into a grand arched entry foyer with split floor plan , 3 spacious bedrooms are in front of the home with 2 full guest bathrooms. Master bedroom is in the rear of the home. Open floor plan which leads to an elegant Gourmet kitchen with 42” Timberlake Level 5 cabinets with soft close hinges, New recessed LED lighting and large island with snack bar area . Kitchen includes custom built in cabinets in pantry, Upgraded Samsung fingerprint resistant black stainless steel appliances in 2017 and LG Viatera quartz countertops. Kitchen/ family room combo which provides plenty of space to gather and entertain family and friends. Large dining room area with sliding door to Large Screened Lanai. The upgrades on this house are impressive with laminate wood floors, elegant tile flooring , tray ceiling, quartz countertops, farm style sink and modern backsplash and doors. The master bath has large shower, dual quartz vanities and a large custom master closet. Upgrades include Level 5 Timberlake cabinetry throughout home, New Water tank with Hybrid Hot Water Heater 2020, Interior painted 2017, Exterior painted 2020, Garage commercial grade epoxy 2017, Generator hook up installed 2020, 4 ceiling storage racks installed in Garage 2017, all new interior light fixtures changed to LED 2017, 3M, tinting/security film installed on all double pane windows and doors 2017, wainscoting installed in foyer and hallway 2020, Central vac, core foam insulation in block foundation, additional exterior electrical outlets, extended outside rear patio, and prewiring for a pool! Extended paved Patio outside for additional private gathering area with side Pond view. Neighbors only on one side with beautiful water views! Sit on your front porch and enjoy the picturesque Lake Hickory nut lake views!! Waterleigh community has 2 resort style community pools and clubhouses which includes Fitness Centers, Tennis Courts, Mini Golf, Walking Trails, Parks, Playgrounds, a Community Dock and 10,000 square foot Amenities center, outdoor covered pavilion, and sports field. Landscaping maintenance is included within the HOA fee. Close to 429, Disney Parks, Orange National Golf courses and shopping and restaurants of Horizon West! Come and enjoy the wonderful lifestyle of Waterleigh community and all it’s amazing amenities. Very special lot with Water views! Hurry, won’t last!

16041 Hampton Crossing Drive, Winter Garden
$1,975,000
5 Beds ⋅ 4 Baths ⋅ Deer Island SubDv. ⋅ 34787 Zip Code
Luxury GATED LAKEFRONT community of Deer Island offers 1+ acre estate homes, panoramic views of Johns Lake and unrivaled privacy. This 1.06-acre single level home is an ENTERTAINER’S DREAM inside and out. Entering the double decorative glass doors, be impressed with the expansive open concept, highlighting the sweeping pool and lake views. The floor to ceiling windows displays the lake and the 55’ infinity edge pool with zero entry, 9’ deep end and features that captures your attention from every turn. The edge of the pool overlooks breathtaking views of the lake while you're hearing is stimulated by sounds of nature. The expansive pool deck is ready for your outdoor kitchen design. Inside, the open living space includes wall-to-wall European travertine stone floors. Nestle into the wood burning fireplace, 18’ vaulted ceiling with skylights, and designer finishes. The open floor plan includes a large dining area with seating for 12 or more comfortably. The chef’s kitchen features unique hide-a-ways and beautiful lighting with it's focal point being an oversized granite island measuring 11.6’ x 5.8’ easily seating 5. The double row base cabinets include a 36” Thor 6 burner gas stove and oven with a beautiful custom wood hood, dishwasher, and farmhouse sink, built-in electric oven and microwave are all added amenities. Bonus entertainment room suitable for pool table and bar which overlooks lake views and spectacular poolside views. A full shower, bathroom and changing area are pool deck accessible. The split bedroom plan adds complete privacy to all luxury amenities including the new master suite. The suite greets you through 5’ x 8’ spectacular solid wood doors. Brazilian cherry flooring and cathedral ceilings of solid cherry are impressive. The 10’ accordion impact glass doors lead you to an upper deck of privacy. You’ll enjoy a second fireplace as you soak in the lake views, pool and the quiet, serene privacy of your backyard. The home has plenty of storage space with the master suite featuring his and hers separated large cedar walk-in closets, including temperature-controlled storage above. Two additional closets in the ensuite bath include marble flooring with heated floor system, chandelier, water closet, dual vanities on each side and a glass enclosed walk-in steam shower. The shower sprays 6 rain showers and jets at every angle with a two-person jacuzzi tub, marble floor tile with a hidden drain system, marble ceiling and walls and specialty lighting and accents throughout. Rounding out the main living floor off the front is a multi-functional room or office plus guest bedroom ensuite with travertine walk-in rain shower, wand, jets, specialty lighting and bluetooth connection. 3 additional Bedrooms on the other side of the home share a travertine stone bath with a double vanity and tub-shower combo, specialty lighting and bluetooth connection. One bedroom is connected creating a second master ensuite having its own pool and lake views, cedar walk-in closet and extra loft for sleeping, hanging out or storage. The full-size laundry room and custom pantry with pull outs located just off the kitchen with matching cabinets and counter space, utility sink passes through to the 3-car garage with attic storage. This leads to the outdoor circular driveway. A wide variety of trees on the property include papaya and avocado as well as pineapple. Down towards the lakefront is the boat slip ready to add your own personal touch.

17509 Deer Isle Circle, Winter Garden
$445,000
3 Beds ⋅ 2 Baths ⋅ Crown Point Spgs SubDv. ⋅ 34787 Zip Code
GOLF CART DISTRICT ALERT! Beautifully remodeled home on a large lot with no rear neighbors. Oversized kitchen island with beautiful stone countertops, wood cabinets, new roof, bathrooms, windows, plumbing, insulation... etc. is only a few of the many upgrades on this property. Abundance of natural light provides a peaceful setting to the beautiful master bedroom with dual sinks in the bathroom and walk-in shower. A brick fireplace is the focal point of the family room, while the extra Florida room creates extra bonus space. Covered screened lanai, mature trees, fire pit and above ground pool provide an oasis right in your backyard. All appliances convey, this home is all about the LOCATION! and is ready for new owners! Just a quick golf cart ride to the historic downtown Winter Garden and the West Orange Trail More Photos to come!

1052 Spring Loop Way, Winter Garden
$5,300,000
6 Beds ⋅ 6.5 Baths ⋅ Isles Of Lake Hancock SubDv. ⋅ 34787 Zip Code
Welcome to Villa Venecia, a privately gated lakefront estate set amidst two lakes within the exclusive gated community of the Isles of Lake Hancock. With 6 bedrooms, 6 full and 3 half baths and 8552 sq ft (12,391 total), this extraordinary Mediterranean masterpiece showcases only the finest craftsmanship and materials, exuding opulence in every detail. Beyond the private electric driveway gates, distinctive verdant landscaping lines the long travertine driveway. Built by Dave Brewer, Villa Venecia is nestled along the southern shoreline of Lake Hancock within an enclave of custom-built lakefront homes, ideally situated on pristine shoreline frontage with the lake’s most expansive water views. At the entry, the handcrafted rustic mahogany and wrought iron doors open to polished travertine floors enhanced by a tile mosaic, flowing to a remarkable picture window where the infinity edge pool blends to long, dreamy lake vistas that invite. Sensational choice Italian original paintings by local artist Joel Cook adorn the entrance, theater ceiling and entrance, wine room, outdoor spa, and kitchen range hood. The Kitchen includes two custom-paneled Sub-Zero refrigerators with four freezer drawers, three Miele dishwashers, an industrial Wolfe range, and a large hidden pantry. All main floor living areas and second floor balcony look out to the infinity pool and spa, surrounded by expansive covered outdoor living areas, complete with an outdoor kitchen, tv, and fireplace. The exquisite main floor master wing includes a morning kitchen and opens to the poolside oasis overlooking the lake. The wine cellar is accessed from the extravagant formal dining room. The ten-seat theater is accessed from the kitchen and is equipped with a 5’x8.5’ screen and cinematic motifs, maintains the rich elements of the residence. The main floor gym can be accessed from within or separately and includes outside showers. The large game room features a beamed, tongue-and-groove cathedral ceiling, includes its own bar, and opens through sliding glass doors to the outdoor living area. The entire pool deck area is surfaced by natural stone and offers stunning lake views. With TWO lakes—and docks—the custom dock and boathouse on Lake Hancock and the boathouse, deck and dock on the adjacent private man-made water ski lake, Villa Venecia avails the very best opportunities to fully enjoy Florida lake life. Lake Hancock is a chain of three lakes, pristine waters with miles of shoreline for boating, and is paradise for fishing and all water sports. For water ski enthusiasts, one of only 15 memberships to the exclusive Isles of Lake Hancock Ski Club is available to access the world-famous man-made water ski lake across the street–with an additional large private boathouse as part of the membership. Many top golf courses are nearby, including Isleworth, Keene’s Pointe, Disney, Orange County National, The Four Seasons, and West Orange. Shopping conveniences at Hamlin are only minutes away, and the Hamlin town center plans include docks for water access to restaurants, shops and a movie theater. All only minutes from downtown Winter Garden, Windermere, Disney and the world famous attractions of Orlando.

14401 Isleview Drive, Winter Garden
$640,000
4 Beds ⋅ 3 Baths ⋅ Lakeview Preserve SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. Your dream home is waiting for you! This home has fresh interior paint and partial flooring replacement . Windows create a light filled interior with well placed neutral accents. You'll love cooking in this kitchen, complete with a spacious center island and a sleek backsplash. You won’t want to leave the serene primary suite, the perfect space to relax. Other bedrooms provide nice flexible living space. Take advantage of the extended counter space in the primary bathroom complete with double sinks and under sink storage. Take it easy in the fenced in back yard. The covered sitting area makes it great for BBQs! Don't miss this incredible opportunity.

3265 Sailing Pier Avenue, Winter Garden
$624,999
4 Beds ⋅ 3 Baths ⋅ Orchard Hills Ph 2 SubDv. ⋅ 34787 Zip Code
MORE PHOTOES COMING SOON! WELCOME HOME! LOCATED IN ONE OF THE MOST DESIRABLE NEIGHBORHOODS IN WINTER GARDEN, ORCHARD HILLS. THIS 4 BEDROOM 3 BATH WITH A SECOND FLOOR BONUS IS PERFECT. EXCELLENT LAYOUT FOR ENTERTAINING. COVERERED PORCH, LARGE FENCED IN BACKYARD WITH PLENTY OF ROOM FOR ACTIVITIES. WELL MAINTAINED! SOLAR PANELS FOR LITTLE TO NO ELECTRIC BILL!!! LOCATED 10 MINUTES AWAY FROM WINTER GARDEN VILLAGE. 5 MINUTE DRIVE TO HAMLIN.

4924 Wildwood Pointe Road, Winter Garden
$665,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West D SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. Fully Paid for solar system, average power bill last 4 months only $24, new roof in 2018, home warranty by HWA included! Step into luxury living in this gorgeous 4 bedroom, 3 bath home in the gated community of Stoneybrook West. From the moment you drive up to this stunning property, you’ll be in awe of the beautifully manicured lawn, spacious driveway and oversized lot. Upon entering, you’ll fall head over heels for the open, airy layout of the home with excess natural lighting flowing throughout, providing a warm welcome to friends and family. The formal dining room lies to the side of the entrance, with direct access to the kitchen, which makes entertaining guests a breeze! The kitchen is fit to handle any size meal with ease with Corian countertops, ample storage, a breakfast bar, and modern stainless-steel appliances. From the kitchen you can look out onto the family room, perfect for spending quality time with your loved ones for a movie night or just a fun night in. Additionally, the first floor includes an en suite bedroom which is ideal for hosting guests or living with older relatives, so everyone in the home can feel comfortable in their own space. Upstairs you’ll find the bonus loft area, which can serve as a TV room, playroom, den, or anything else to suit your family’s needs. Moreover, the master bedroom lies upstairs and is sure to become your own personal oasis, with a luxurious master bath, large walk-in custom built closet, and direct access to the enclosed and air conditioned balcony. Feel free to unwind in your fully enclosed and air-conditioned patio, or savor a peaceful evening on the upstairs balcony, all while taking in the stunning sunsets and gorgeous water views. The master bathroom includes chic finishes, a sizable walk-in shower, and a large soaking tub, perfect for relaxing at the end of the day. The additional bedrooms upstairs all include plenty of space, storage and natural light, ensuring the whole family will feel right at home. The laundry room is situated upstairs as well for optimal convenience. Heading outside, you’ll find the spacious backyard with gorgeous scenery, an optimal setting to let the four-legged friends or little ones have fun in the warm Florida weather. The fun continues with the long list of amenities Stoneybrook West has to offer. Enjoy the wonderful benefits of this community such as a fitness center, pool, splash pad and playground for limitless family fun. Exercise your competitive side with our tennis and basketball courts or enjoy the lakefront with a fishing pier and community dock off Black Lake. And with Wi-Fi and cable included, you can stay connected all while feeling right at home. With the recent work of this home, in addition to a Home Warranty being offered through Home Warranty of America, you can be at ease knowing this home is move in ready. Located close to all the shopping and dining the Winter Garden Village has to offer, as well as close proximity to major attractions, the 429, amazing schools, and parks, you’ll have everything you need close by! Don’t wait on this gorgeous home, schedule your private tour TODAY!

13518 Tenbury Wells Way, Winter Garden
$748,630
4 Beds ⋅ 3.5 Baths ⋅ Lakeview Preserve SubDv. ⋅ 34787 Zip Code
Under Construction. At Pulte, we build our homes with you in mind. Every inch was thoughtfully designed to best meet your family’s needs, making your life better, happier and easier. The expansive Whitestone two-story home design features 4 bedrooms, an enclosed flex room, 3 full bathrooms, a powder room, a spacious loft, an open-concept kitchen, café and gathering room, an extended covered lanai and a 2-car garage. Upon entry, you are greeted by the flex room – perfect as a home office or private den, and your powder room. The stunning foyer continues past the laundry room, towards the kitchen, gathering room and café. Your gourmet kitchen features a corner walk-in pantry, a large center island, built-in stainless-steel appliances, 42” soft-close white Lillian cabinetry with coordinating wooden vent hood, black hardware and Pearl Jasmine quartz countertops and a stunning white picket tile backsplash. The owner’s suite is located on the main level of your home and features an en suite bathroom with walk-in closet, dual-sink Pearl Jasmine quartz-topped double white Lillian vanity with black hardware, private water closet and walk-in super shower. Upstairs you'll find your spacious loft, three additional bedrooms and the additional bathrooms. Professionally curated structural and design selections include an extended covered lanai, enclosed flex room, fourth bedroom with en suite bathroom, outdoor kitchen pre-plumbing, pocket sliding glass doors at the gathering room, 8-foot interior doors, an oak stair rail with iron spindles, built-in kitchen appliances, super shower in the owner's en suite bathroom, an upgraded laundry room with quartz-topped cabinets, designer tile accents in the kitchen and bathroom showers, gorgeous wood-look Liana Forest porcelain tile flooring throughout the first floor living areas and in the bathrooms, soft, stain-resistant Shaw Owl carpet in the bedrooms and loft and so much more. This stunning dream home is packed with tons of luxury upgrades and is one of the final opportunities to own a Whitestone home in Lakeview Preserve so visit today! Lakeview Preserve in Winter Garden offers new homes in a gated location that can't be beaten, featuring fabulous community amenities such as a fitness center, resort style pool with splash pad and cabana, clubhouse, playground, picnic area, kayak launch to Johns Lake, no CDD fee, and all home designs are pre-wired for Smart Home Technology. Lakeview Preserve is only 5 miles to Downtown Winter Garden and 10 minutes from SR 429, which connects to all main thoroughfares, making your daily commute easier. Visit us to learn why Lakeview Preserve is the best place to call home!

3228 Sailing Pier Avenue, Winter Garden