Winter Garden/Oakland Homes with Storage Exterior Features

**GOLF CART COMMUNITY** Welcome to this charming home located at 1631 Charlemagne Ct in Winter Garden, FL. This beautiful house features three spacious bedrooms, a dedicated office, 2 full bathrooms, living room, dining room (currently using as a second office) laundry room and a two car garage, providing ample space for comfortable living. A beautifully maintained and thoughtfully upgraded home tucked away on a quiet cul-de-sac in one of Winter Garden's most desirable residential neighborhoods. Sitting on a large, fully fenced lot, this property delivers privacy, peace, and timeless appeal, with mature Oak trees providing lots of shade for outdoor entertaining. With a generous living area of 2,035 square feet, this home accords an inviting layout appropriate for relaxation and entertaining. Step inside and you're immediately greeted by cathedral ceilings in the living room and kitchen, creating an open, airy atmosphere filled with natural light. Tile flooring throughout the entire home adds a clean, cohesive look while offering durability and easy maintenance. The chef-inspired kitchen is the heart of the home, showcasing upgraded custom cabinetry, and granite countertops. The kitchen features abundant cabinet space and a large pantry offering exceptionally storage for all your kitchen essentials. Included are Bosch appliances and a charming nook overlooking the beautiful mature landscaping. The primary bedroom suite is a truly spacious sanctuary, complete with elegant plantation shutters, a Jacuzzi tub, dual sinks and his-and-her walk-in closets. Two additional bedrooms and a full bath provide comfort and flexibility for family or guests. The laundry room has built-in cabinetry, countertop and additional overhead shelf for added storage. A hall linen closet has extra-large storage providing plenty of space for additional household essentials. Major upgrades bring peace of mind and value including a new roof (2021), exterior freshly painted (2021), Brand-new AC (2024), Newly planted sod in back yard (2026) and upgraded Irrigation Control Panel (2026). Hop on your golf cart just minutes to historic downtown Winter Garden and enjoy your favorite restaurants, events and farmers market. Or take a relaxing nature walk or bike ride on the West Orange trial. This home is move in ready!

1631 Charlemagne Court, Winter Garden

$585,000

2 Beds ⋅ 2 Baths ⋅ O6441955 MLS

**Click the Link for Virtual Tour** RARE TURNKEY OPPORTUNITY IN THE HEART OF DOWNTOWN WINTER GARDEN! Just three blocks from Plant Street and located within the golf-cart district, this beautifully renovated 2-bedroom, 2-bathroom cottage combines one of Winter Garden?s most sought-after locations with the flexibility of a primary residence, second home or established short term rental. Thoughtfully renovated down to the studs in 2016, the home blends historic cottage character with extensive modern improvements including updated electrical and plumbing, engineered hardwood floors, renovated kitchen and baths, double-pane windows, natural gas tankless water heater, metal roof and A/C was replaced in 2022. The open floor plan features a charming window seat in the living room, while the primary suite offers a walk-in closet and en-suite bath with dual sinks and oversized shower. A second full bath provides direct exterior access to the backyard - convenient for outdoor entertaining or future pool. Outside, the nearly quarter-acre fenced property offers something increasingly difficult to find this close to downtown: room to enjoy. Relax on the restored rear deck beneath the mature shade tree, utilize the approximately 200-sq.-ft. powered shed as storage, workshop or hobby space, and enjoy the convenience of a carport and additional outdoor space. Leave the car at home and walk, bike or take your golf cart to Plant Street, the West Orange Trail, Plant Street Market, Crooked Can, restaurants, boutiques, the farmers market, festivals and downtown entertainment. Currently operated as a short-term rental and offered turn-key with furnishings and accessories included, with existing reservations extending through March 2027. Whether you're searching for a downtown residence, vacation home or investment property, this is an opportunity to own a distinctive piece of the Downtown Winter Garden lifestyle.

325 W Newell Street, Winter Garden

$719,500

4 Beds ⋅ 3 Baths ⋅ O6436846 MLS

Experience the perfect blend of comfort, charm, and functionality in this beautiful Winter Garden home! Featuring 4 bedrooms and 2.5 baths, this spacious residence offers an impressive second-story loft and a versatile fourth bedroom with its own half bath—perfect for guests, a media room, or flexible living space. The thoughtfully designed first floor features a private primary suite with an ensuite bath, two additional bedrooms sharing a full bath, a spacious family room, and a beautifully appointed kitchen that truly serves as the heart of the home. Kitchen features include built-ins and French doors that open to a gorgeous deck, creating an ideal setting for indoor/outdoor entertaining. A formal dining room and separate office with French doors provide additional space and privacy. Step outside to enjoy peaceful outdoor living in the landscaped backyard, complete with a private patio/deck perfect for relaxing or entertaining. A 3-car garage plus a dedicated golf cart garage adds exceptional convenience and storage. Located in highly sought-after Downtown Winter Garden, this home is close to top-rated schools, shopping, parks, West Orange Trail, and popular dining destinations. Enjoy the unique lifestyle of a golf-cart-friendly downtown district while being just minutes from everything you need. ON-SITE Generator for Hurricane season too. Recent updates include a New Roof (2020), New hot water tank, New mini-split, A/C Main (2023), and fresh interior paint (2026). Buyers....$10k towards rate buy down or closing costs/prepaids at closing w/ full price offer. Come discover all this wonderful home has to offer and make it yours!

502 Palm Drive, Winter Garden

$499,900

3 Beds ⋅ 2 Baths ⋅ O6437038 MLS

A rare opportunity in downtown Winter Garden awaits! This beautifully maintained 3 bedroom, 2 bathroom home presents a chance to enjoy the vibrant lifestyle of downtown Winter Garden's golf cart district, complete with a new roof and a water heater less than two years old. A spacious driveway and manicured front lawn create a welcoming first impression. Inside, the home features a functional layout designed with both comfort and entertaining in mind. The dining area sits just off the entry and connects directly to the kitchen, making everything from casual dinners to larger gatherings feel seamless. The kitchen combines practicality with charm, featuring stainless steel appliances, built-in shelving, high ceilings, and a bright atmosphere. Overlooking the living room, it keeps the main living spaces connected while adding convenience to everyday life.The living room serves as a cozy gathering space centered around a functioning wood-burning fireplace, creating the perfect setting for relaxing evenings at home. A thoughtful split-bedroom layout provides added privacy, with the primary suite positioned separately from the secondary bedrooms. The primary bedroom includes direct access to the oversized screened-in patio and a private en suite bathroom featuring a tub and separate shower. The additional bedrooms are generously sized with natural light and ample storage, providing comfortable accommodations for family members, guests, or a home office. Step outside and enjoy an oversized screened-in patio complete with a ceiling fan, giving you the ideal place to relax outdoors while staying protected from Florida's elements and pests. Beyond the patio, the large fenced backyard provides plenty of room for four-legged friends, and little ones to roam freely without worry, or to accommodate fun activities like gardening or hosting loved ones. The options are limitless! A dedicated shed adds additional outdoor storage for tools, bikes, and recreational gear. Another standout benefit is the extremely low HOA, with the current HOA paid through June 2027, giving the next owner even more value and peace of mind. Living within Winter Garden's golf cart district means you can easily enjoy the area's beloved farmers market, boutique shopping, local restaurants, community festivals, and events without having to go far. Major highways are also conveniently nearby, along with excellent schools. With a new roof, newer water heater, spacious outdoor living areas, and an unbeatable downtown Winter Garden location, this home presents an exciting opportunity to create a space that truly reflects your style and vision. Come see the possibilities, make this home your own, and start enjoying the Winter Garden lifestyle today. Schedule your private tour!

217 Harbor Drive, Winter Garden

$649,000

4 Beds ⋅ 3 Baths ⋅ O6433153 MLS

Located in the Oakglen Estates community of Winter Garden, this spacious 4-bedroom, 3-bathroom home offers a functional open layout, tall ceilings and plenty of room to live and entertain. The updated kitchen features an oversized island, abundant cabinetry and a large pantry conveniently connected to the laundry room, which also provides exterior access. Luxury vinyl flooring runs throughout the main living areas, with brand-new carpet in two guest bedrooms. The spacious primary suite features additional closet/shelving, two walk-in closets and a large en-suite bathroom with a soaking tub and separate shower stall. Both guest bathrooms have been beautifully remodeled. Step outside to enjoy a private fenced backyard with a built-in sunshade, exterior electric perimeter dog fence and a variety of fruit trees, including guava and berry bushes. The home offers the space, updates and functionality today's buyers are looking for, all within a well-established Winter Garden neighborhood. Enjoy easy access to Winter Garden's Historic Downtown, Lake Apopka, the West Orange Trail for biking and walking, shopping, dining and the many amenities that make Winter Garden such a sought-after place to call home. Homes in this established community don't come to market often—don't miss your opportunity to make 531 Hearthglen Blvd your own.

531 Hearthglen Boulevard, Winter Garden

$644,000

5 Beds ⋅ 4 Baths ⋅ O6424514 MLS

A RARE FIND IN THE HIGHLY DESIRABLE WINDING BAY COMMUNITY! This beautifully designed home offers the perfect blend of comfort, flexibility, and income potential. One of its most impressive features is the FULLY EQUIPPED PRIVATE ONE-BEDROOM APARTMENT ABOVE THE GARAGE with its own private entrance, spacious living room, full kitchen, private bedroom, walk-in closet, laundry area, and full bathroom. The apartment is CURRENTLY TENANT-OCCUPIED, providing immediate rental income for the next owner while also offering incredible flexibility as a guest suite, multigenerational living space, or a completely private home office. The main residence features 4 spacious bedrooms and 2.5 bathrooms, with the PRIMARY SUITE CONVENIENTLY LOCATED ON THE FIRST FLOOR, offering comfort and privacy. The open-concept floor plan showcases elegant tile flooring throughout the main living areas, premium carpeting upstairs, 8-foot interior doors, upgraded lighting, and abundant natural light that creates a warm and inviting atmosphere. A standout architectural feature is the CHARMING SECOND-FLOOR FRONT PORCH, the perfect place to enjoy your morning coffee, unwind in the evenings, or simply relax while taking in the peaceful neighborhood views. Residents of Winding Bay enjoy resort-style amenities, including a community pool, splash pad, playground, and dog park, all with a low HOA fee. Ideally located just minutes from SR-429, approximately 10 minutes from Walt Disney World, and close to Horizon West Town Center, shopping, dining, and Orlando International Airport, this home is also zoned for highly rated schools. Whether you're looking for a primary residence with built-in rental income, a home designed for multigenerational living, or the convenience of a private apartment for guests or a dedicated workspace, this exceptional property truly offers the best of Central Florida living.

15068 Lebeau Loop, Winter Garden

$1,790,000

6 Beds ⋅ 4 Baths ⋅ O6418208 MLS

TWO HOMES FOR THE PRICE OF ONE.... Explore this stunning 10-acre lakefront estate in southwest Winter Garden with everything you’ve been dreaming of within 20 minutes of all the major theme parks in Central Florida. This beautiful tree-lined property offers privacy, shade, and plenty of space for both you and your animals. The owners have enjoyed using the land as a family ranch and oasis for many years, making it an ideal home for horse owners or those who just want to get away to relax and create lasting memories. You’ll also love the peaceful waterfront setting, where you can enjoy breathtaking sunsets. Beyond the incredible land, the property includes a spacious 3,196-square-foot main home with four bedrooms, three bathrooms, fireplace, screened patio and swimming pool with outdoor spa. In 2017 owners built a 1,200-square-foot guest house with a two-car garage, perfect for visitors or extra living space. Both homes are equipped with metal roof and screened porches. Despite its peaceful country feel, you’re still conveniently close to hospitals, restaurants, and shopping. If you’re looking for a property that combines the beauty of ranch living with laid back comfort and convenience, this is the perfect place to call home. Video https://youtu.be/FU5ZvzJ_3PM

16945 W Phil C Peters Road, Winter Garden

$399,000

4 Beds ⋅ 2 Baths ⋅ O6421715 MLS

PHENOMENAL Double corner LOT NO HOA, newer updates INCLUDE: brand new AC, new roof, Re-Plumb, house/ Electrical Panel/rewired. Updated kitchen and bathrooms, Located off the Kitchen is the Dining room area which is open to the Living Room area. The master Bathrooms is completely updated features a standing shower. The Laundry is located inside. The carport/workshop is spacious to hold 2 cars and storage. Enjoy the nice-sized Backyard with a that is big enough for the whole family. You don't want to miss this opportunity to make this house your home! very nice WORKSHOP ** VALUE IS IN THE both property/land

689 Bethune Avenue, Winter Garden

$1,724,500

5 Beds ⋅ 6 Baths ⋅ O6416046 MLS

Virtually Staged. BEST PRICED HIGH QUALITY LAKEFRONT HOME in Winter Garden! Spectacular Views with 99 Feet of Shoreline- perfect spot to build a DOCK!! Start Enjoying LIFE ON THE LAKE in this Special Home built with the HIGHEST LEVEL OF UPGRADES! Enjoy Boating, Fishing, Kayaking or try the WATER SKI COURSE on 420 Acre Lake Hickorynut just minutes from Disney! Enter this 4,641 sq ft Home with 5 Bedroom Suites and 6 Full Baths through a PRIVATE COURTYARD. Double Doors with Leaded Glass Welcome you to a life of LUXURY! First Floor has Soaring 12 Foot Ceilings, Tray Ceilings, 7 ¼” Baseboards and four Ten Foot Tall Sliders that open to the nearly HALF ACRE Premium Lot with Wide Open Lake Views! Outstanding Features include: Premium Lot that is over 200 Feet Deep, a true GOURMET Kitchen with all WOLF Appliances: Sub-Zero 36” SS Refrigerator, Sub-Zero 36” SS Freezer, Wolf E Series Wall Oven, Convection Steam Oven, Warming Drawer and Wolf Induction Cooktop. The DOUBLE Stacked Raised Panel Cabinetry features a HIDDEN Pantry with CUSTOM Shelving! The Great Room has a Custom Built-In and a Butler Pantry was added near the Dining Room. Oversized Covered Patio is enhanced with Electronic RETRACTABLE Screens, and the Pool Bath is just steps away. Impressive FIRST FLOOR PRIMARY SUITE with Hickory Flooring opens to Spa Bath with DOUBLE Vanities, FREESTANDING TUB, Spacious Shower and Large WALK-IN CUSTOM Closet PLUS a LAUNDRY ROOM with Sink and a STORAGE Closet! Private Suite 2 has Lake Views, Custom Built-In Shelving, Large Bath and Custom Closet. Private Suite 5 overlooks the Courtyard. The CUSTOM Staircase with Oak treads leads upstairs to 2 more Bedroom Suites with 10’ ceilings and Custom Closets, a LARGE Bonus Space wired for SURROUND SOUND is an Ideal THEATER ROOM and a large Covered Balcony with Electronic Screens that is a perfect spot for Relaxing while Enjoying the Sunset over the Lake! Upstairs Laundry Room with original plumbing has been converted to Mini Kitchen – great opportunity for a Mother-In-Law Suite! Outstanding Upgrades Include Engineered Hickory Flooring in entire 2nd Floor and Bedrooms, WATER FILTRATION system, Gutters, Drop Zone with Cabinetry, SOLID CORE Doors throughout home and UV Light in AC Units. Property is very ENERGY EFFICIENT with Double Pane Lo E Windows, Radiant Barrier and Extra Insulation in the Concrete Block. Waterleigh is a Lifestyle Community with 4 Community Pools, 3 Clubhouses with Fitness Centers, Tennis, Pickleball, Mini Golf, Parks, Playgrounds, Community Fishing Dock and MORE! HOA Does all Yard Maintenance. Schools Include Panther Lake Elementary, Water Spring Middle and NEW Horizon High School. Close to Shopping, Dining, NEW Publix, DISNEY and convenient to 429, 1-4 and 417!

8750 Bayview Crossing Drive, Winter Garden

$415,000

3 Beds ⋅ 2 Baths ⋅ TB8497081 MLS

Location! Location! Welcome to this wel maintained 3 beds 2 bath single family home located in the desirable community of Stone Creek in Winter Garden. This home offers a spacious living room, dining area, spacious master bedroom with double sink and walking closet, 2 extra bedrooms and sharing bath, 2 car garage, screened porch and generous fenced back yard. This property is convenient located near shops, restaurants, and the highly rated Elementary School is located inside the community with walking distance. Also, near Winter Garden village Mall, Stonybrook West Golf Club, Tucker Ranch Wellness Park (in construction) And easy acces to the Highway and Airport.

15187 Harrowgate Way, Winter Garden

$969,000

3 Beds ⋅ 3 Baths ⋅ O6397262 MLS

Virtually Staged. Back on the market and better than ever! Your Own Florida Paradise - Private, Elegant and Rare. Arrive in Winter Garden and escape into a private garden paradise unlike anything around it. More than an acre of mature trees, colorful plantings, and beautifully landscaped grounds create a serene backdrop with no rear neighbors...a setting that feels wonderfully removed, yet keeps every convenience close at hand. The recently resurfaced screened pool showcases beautiful new tile and a spa with water overflow; the pool and spa are professionally serviced weekly. An impressive 40-foot covered lanai extends the living space outdoors for year-round entertaining, quiet afternoons and sunset dinners among the gardens. The adaptable three-to-four-bedroom, three-bath floor plan offers effortless flexibility for guests, a home office or multigenerational living. A custom entertainment center with integrated surround sound adds a distinctive focal point to the main living area. A recently replaced roof, recent water heater and cooktop, and a fully serviced air-conditioning system make this an outstanding primary residence or seasonal Florida retreat. Lake Tilden and Black Lake access, boat ramps, tennis courts and a community pavilion complete the experience; near hospitals, fine dining, premier shopping, downtown Winter Garden, major roadways and world-famous attractions.

14140 Country Estate Drive, Winter Garden

$699,000

3 Beds ⋅ 2 Baths ⋅ O6392994 MLS

Welcome to this beautifully maintained home in the highly sought-after Woodbridge on the Green community, overlooking West Orange Country Club and perfectly situated in the hub of Winter Garden. This waterfront home offers a blend of comfort, style, and convenience—ideal for anyone looking to enjoy the best of Central Florida living. Step inside to an inviting, light-filled layout featuring spacious living areas, high ceilings, and thoughtfully designed spaces that make everyday living effortless. The kitchen offers generous counter space, ample cabinetry, and a functional layout perfect for cooking, entertaining, or gathering with family. The primary suite provides a peaceful retreat with a well-appointed bathroom and plenty of closet space. Additional bedrooms are comfortably sized and versatile—ideal for guests, a home office, or a growing household. Outside, enjoy a very large private backyard on the pond, with room to relax, garden, or entertain. New concrete tile roof was installed in 2023. Woodbridge on the Green is known for its mature landscaping (fully HOA maintained), quiet streets, and welcoming atmosphere; the HOA also covers house painting on a rotating schedule and also yard lawncare, helping to ensure an immaculate community aesthetic. Located just minutes from Windermere, top-rated schools, major highways, and the charming Historic Downtown Winter Garden, this home offers unmatched convenience with shopping, dining, and entertainment right at your fingertips. This is a wonderful opportunity to own a home in one of Winter Garden’s most desirable neighborhoods—move-in ready and full of potential.

14050 Fairway Willow Lane, Winter Garden

Winter Garden/Oakland Homes with Storage Exterior Features

Newest Winter Garden/Oakland Homes with Storage Exterior Features