Winter Garden/Oakland Real Estate

Winter Garden/Oakland Real Estate

Welcome to the charming region of Winter Garden/Oakland in Orange County, Florida! This picturesque area is known for its beautiful landscapes, rich history, and vibrant community.

Winter Garden is a historic city with a quaint downtown area featuring brick-lined streets, local shops, and delicious eateries. Residents and visitors alike can enjoy the weekly farmers market, where local vendors offer fresh produce, handmade goods, and more. The city also boasts a variety of parks and outdoor recreational activities, making it a great place for nature lovers.

Just a stone's throw away is the town of Oakland, known for its small-town charm and friendly atmosphere. With its tree-lined streets and historic homes, Oakland offers a peaceful retreat from the hustle and bustle of city life. Residents can take advantage of the town's community events and close-knit neighborhoods.

Whether you're looking to settle down in a family-friendly community or seeking a peaceful retreat, Winter Garden/Oakland has something for everyone. With its convenient location near Orlando and all that Central Florida has to offer, this region is the perfect place to call home. Come explore the beauty and charm of Winter Garden/Oakland – you won't be disappointed!

Newest Listings in Winter Garden/Oakland

$575,000
4 Beds ⋅ 3.5 Baths ⋅ Waterside/Johns Lake Ph 2c SubDv. ⋅ 34787 Zip Code
BRING YOUR OFFERS! Listed under appraised value! This amazing home sits on the BEST CORNER LOT in the exclusive Waterside at Johns Lake community. The back faces a beautiful view of a conservation area, so NO REAR NEIGHBORS! Find yourself just 20 minutes away from Disney, Universal and other main attractions! Also, it is conveniently close to the historic downtown district, great dining, shops, A+ schools: Hamlin Elementary and Hamlin Middle. It was built 2 years ago so almost new! This property consists of 4 bedrooms,3.5 baths on an open floor plan. The spacious master bedroom is on the first floor with an en-suite master bath, walk-in closet and a double vanity with quartz countertops. Prepare dinner in a gourmet kitchen with an island/breakfast bar that overlooks the great room perfect for entertaining guests. It includes wood cabinets, stainless steel appliances and quartz countertops. There is a half-bath downstairs for the convenience of guests. Upstairs, you will find a generous loft which could be used as a play area or additional living space, as well as 3 bedrooms and 2 full bathrooms providing privacy to all the family members. Enjoy daily sunrises and sunsets while sitting in the screened lanai next to the fenced in patio. There is a 2-car garage and a nice, paved driveway with space for 2 additional autos. Enjoy a short walk to John's Lake with a fishing dock and playground plus amenities as a resort style pool, clubhouse and state of the art fitness center for a low HOA of $196 monthly. No CDD. This very well-maintained home is ready to move in!

1455 Viscaya Cove Boulevard, Winter Garden
$750,000
4 Beds ⋅ 3.5 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code
**WINTER GARDEN DREAM HOME ALERT** **SUPER PREMIUM LOT -- HUGE WITH NO REAR NEIGHBORS -- BACKS TO PEACEFUL & PRIVATE CONSERVATION & WATER VIEWS** **POOL READY** **FOUR BEDROOMS PLUS OFFICE/DEN PLUS BONUS/LOFT** **FIRST FLOOR BEDROOM & FULL BATHROOM WITH WALK-IN SHOWER** **GOURMET KITCHEN** **THREE CAR TANDEM GARAGE** **LONG-LASTING MODERN TILE ROOF** **PET FREE HOME** FLORIDA…PARADISE…FOUND. Welcome to this stunning dream home located in Winter Garden’s highly coveted Waterleigh community which features beautiful homes, incredible amenities and lake views at every turn. This move-in ready home is one of builder D.R. Horton’s luxury EMERALD series which are higher valued homes situated on premium lots like this one and with special custom features, such as this beautiful & long-lasting modern concrete tile roof and three-car extended garage. Get ready to LIVE the Florida lifestyle outdoors with peace, privacy & serenity on this VERY special & large lot backing to conservation & water views. Instead of paying for someone else’s pool design & outdoor decisions...IMAGINE the possibilities of creating your very own custom BACKYARD OASIS with nearly 50 feet of backyard depth…your dream, your choices. This home features the BEST flexible floor plan -- four bedrooms PLUS office/den (easily enclosed if desired) PLUS large loft/bonus room -- one bedroom and FULL bathroom with walk-in tiled shower on the first floor (IDEAL for guest room, office, playroom, etc) -- with very important additional half bath (pool ready) on first floor. SPECIAL FEATURES & UPGRADES include…beautiful wood-look tile throughout the first floor, gourmet kitchen complete with built-in oven, cooktop & range hood, custom-built pantry and bedroom closets, large drop zone with matching cabinetry and countertops, PET-FREE home…& MORE! Enjoy the space in your extended THREE-CAR tandem garage…38 feet in length & ready to fit your cars, workshop, storage, boat, trailer, etc. Your HOA FEE of just $230 per month INCLUDES ALL LAWN CARE CUTTING, FERTILIZATION, EXTERIOR PEST CONTROL & TRIMMING OF HEDGES/TREES of your LARGE lot...in addition to the community's incredible resort-style pools, clubhouses, fitness centers, parks, playgrounds, dog park, beach volleyball, tennis courts, putt-putt, fishing pier, walking trails…& MORE! The PERFECT location -- conveniently located to all of the exciting shopping, dining & entertainment of Winter Garden’s Horizon West -- minutes from Walt Disney World & other area attractions -- minutes from HWY 429 access with easy direct connection to anywhere in Central Florida & beyond -- zoned for top-notch schools including the NEW Horizon High School. WELCOME HOME!

9982 Beach Port Drive, Winter Garden
$625,000
4 Beds ⋅ 2.5 Baths ⋅ Summerlake SubDv. ⋅ 34787 Zip Code
**SUMMERLAKE WINTER GARDEN MOVE-IN READY HOME ALERT** **FOUR BEDROOMS PLUS OFFICE/FLEX SPACE -- OVER 2,600 SQFT** **STUNNING WOOD FLOORS THROUGHOUT ENTIRE FIRST FLOOR** **NATURAL GAS APPLIANCES** **FRESHLY PAINTED INTERIOR & EXTERIOR** **EXPANDED SCREENED PORCH & PATIO AREA -- OVER 400 ADDITIONAL SQFT OF OUTDOOR LIVING SPACE** **LOCATED NEXT TO THE COMMUNITY POOL & AMENITIES** **AVAILABLE FOR QUICK TWO WEEK CLOSING** Welcome to this stunning move-in ready home located in Winter Garden’s highly coveted Summerlake community. Starting with beautiful curb appeal and a large welcoming front porch, this home has the BEST location…just around the corner from the incredible Summerlake community pool, clubhouse, fitness center, tennis courts, parks, playground, zip line & walking trails. LIVE the Florida lifestyle outdoors right at home in the expanded lanai & patio areas…adding over 400 square feet of additional LIVING space to your home! This includes a large covered & screened lanai (11x16) and a beautiful stone paver patio (9x25) for seating, firepit, grilling, play…the options are endless! The inside of the home features a fantastic & FLEXIBLE open floor plan with FOUR bedrooms PLUS an additional first floor office space with the option to easily enclose with doors for privacy. Lovely master suite includes a custom-built faux fireplace feature wall and large bathroom (soaking tub!) and walk-in closet. The secondary bedrooms are LARGE (12x14 and 14x17) with the larger room perfect for use as a bonus room, loft, game room, media room or den if a fourth bedroom is not needed. The expansive open kitchen is truly the centerpiece of the home. ENJOY tons of cabinetry and counter space including a large center island, quartz countertops, stainless steel appliances including a brand new (never used!) refrigerator (SEPT 2024) & NATURAL GAS range & oven, DOUBLE pantry storage, large butler’s pantry (serving area, coffee or wine bar!)...for the professional chef or amateur, you couldn’t ask for more! ALL APPLIANCES STAY. The kitchen area also includes a fantastic dining area complete with custom-built bench for seating. SPECIAL FEATURES & UPGRADES INCLUDE…stunning hardwood flooring throughout the entire first floor, TONS of storage throughout, brand new carpet on stairs & second floor (JUNE 2024), freshly painted interior & exterior (2024), triple slider glass doors to lanai, completely renovated laundry room (washer & dryer stay!), extended garage (24’ length) and long driveway space for plenty of parking, full sprinkler system, technology upgrades including Blink doorbell & patio camera and digital garage door operation through MY Q app…& MORE! Your HOA FEE of approximately $200 per month INCLUDES ALL LAWN CARE CUTTING, FERTILIZATION, EXTERIOR PEST CONTROL & TRIMMING OF HEDGES/TREES...in addition to the incredible pool, clubhouse, fitness center, parks, playground, zip line & walking trails! The PERFECT location -- conveniently located to all of the exciting shopping, dining & entertainment of Winter Garden’s Horizon West -- minutes from Walt Disney World & other area attractions -- minutes from HWY 429 access with easy direct connection to anywhere in Central Florida & beyond -- zoned for top-notch schools including the NEW Horizon High School. Available for quick TWO WEEK CLOSING if desired. WELCOME HOME!

14830 Porter Road, Winter Garden
$435,000
3 Beds ⋅ 2.5 Baths ⋅ Signature Lakes Ph 3b-6 SubDv. ⋅ 34787 Zip Code
3 Bedrooms, 2.5 baths, Corner Unit Townhouse nearby the Hamlin Town Center located by the City of Winter Garden. This house is zoned for Keenes Crossing Elementary School, Bridgewater Middle School, and Windermere High School. Property had a Fenced Courtyard. Formal Dining Room, Formal Living Room, Family Room, First Floor Tile Floor, Second Floor with Vinyl Plank Flooring. HOA fee included Cable TV & Internet. Community features amenities including 2 Community Pools, 2 Clubhouse with Fitness, Green spaces & Park areas, Boat Ramp, Fishing Docks, Tennis & Basketball courts, Billiards & arcade, Bike & walking paths. Rear porch for relaxing and watching fireworks. Home is close to Theme Parks area, the 429 entrance/exit for easy commute, Hamlin Shopping Center, Supermarket and Winter Garden Grove is nearby.

14867 Driftwater Drive, Winter Garden
$575,000
4 Beds ⋅ 3 Baths ⋅ Waterside/Johns Lk-Ph 2c SubDv. ⋅ 34787 Zip Code
This incredible unit with LOTS of extras touches in Waterside on premium lot with no rear neighbors. Wide open well designed kitchen with closet pantry, quartz counters, island and SS appliances. Tiled living areas and spacious great room that is light and bright. Upstairs, in addition to the master owners suite with dual vanities and walk in closet, there are 2 additional bedrooms and a full bath. Large open paver patio is waiting for your custom touches and full 2 car rear entry garage complete a perfect floor plan. Waterside offers its residents an incredible lifestyle with resort level clubhouse with state-of-the-art fitness center, lake side community pool, playground, miles of sidewalks and walking paths and lots of green spaces ! Ideally located minutes from countless shopping and restaurant options in every direction, 25 minutes to Disney, 15 minutes from Clermont and only 10 minutes from downtown Winter Garden. Sought after K-12 school district and short commute to Monte Verde academy, and Foundations Academy. You will not find more for less in 34787, easy to show and ready for a fast closing...leased solar panels drastically lower electric bill.

17039 Quicksilver Avenue, Winter Garden
$825,000
3 Beds ⋅ 2.5 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Experience the pinnacle of low maintenance living with “The Mannington” floor plan in Oakland Park’s McKinnon Square. This unique 2,529 sq ft layout offers three spacious bedrooms, two and a half baths, and a dedicated office. Only two years old, it boasts high-level finishes and upgrades that truly set it apart. Revel in the elegance of 3-inch plantation shutters throughout, 8-foot doors, and a full California Closet buildout in every storage space. Situated on a corner lot, this home is bathed in natural light and surrounded by lush green space and elegant landscaping. The fully fenced yard and expanded brick-pavered side yard are perfect for entertaining, while the expansive front and rear porches offer serene outdoor living areas. Inside, the attached oversized 2-car garage with epoxy-finished flooring provides ample storage and convenience. The home features neutral laminate wood flooring throughout, except for the two guest rooms, which have “like new” carpet. The built-out laundry room offers ample storage and folding table, and the upstairs loft provides additional living space. The gourmet kitchen, with its 10-foot island and upgraded GE Profile appliances, is a chef’s dream. Smart features include upgraded Honeywell thermostats, a Resideo alarm system, a LiftMaster garage opener, and Kwikset keyless door entry locks. Other significant features include a Culligan water softening system. The HOA maintains all landscaping, including mulch, plant replacement as needed, and irrigation repairs, ensuring a comfortable and efficient living experience. Located within the golf cart district and walking distance to the West Orange Trail, “The Mannington” offers the best of Oakland Park living.

934 Mckinnon Square, Winter Garden
$5,000
5 Beds ⋅ 3 Baths ⋅ Grove Pk/Stone Crest A-E SubDv. ⋅ 34787 Zip Code
Auction Property. SFH -5 Bedroom, 3 bath, 3 car garage, situated on a 0.29 acre lot, Just 30 minutes from Orlando International Airport. Concrete Block Stucco on Lost Grove Circle, being Sold As-Is. Drive by only. Submit highest and best at www.federa by October 16, 2024. List price is the opening bid.

854 Lost Grove Circle, Winter Garden
$484,000
3 Beds ⋅ 2 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code
Discover a unique SELLER FINANCING opportunity where after the down payment you simply take over existing mortgage payments in the beautiful Stoneybrook West gated golf community of Winter Garden! This option is perfect for those seeking homeownership who may have the means to afford a home but have been denied by traditional banks. Take advantage of a simplified purchase process allowing you to achieve your dream in this vibrant community. Enjoy access to tons of amenities including a golf course, while just minutes from downtown Winter Garden and the rest of what Orlando has. FULLY FURNISHED BEAUTIFUL HOUSE! Ideally situated in a quiet, gated, and guarded community. It offers open concept living with many updates throughout. Upon entry, you are greeted by a spacious and sun-filled dining/family room with ultra-high ceilings leading to an open-concept kitchen overlooking the living room. This sparkling kitchen boasts new quartz counters, stainless steel appliances, and an in-kitchen laundry closet. The master bedroom is a retreat with tray ceilings and a walk-in closet. Outdoor living extends through the living room to a partially covered and fully screened lanai. 2 Car garage is attached by way of the kitchen. HOA fees include resort-style amenities, a fitness center, a clubhouse, an Olympic pool, a splash pad, basketball, tennis, volleyball, fishing and boating cable, and internet. Bonus points- HOA also includes the internet.

1156 Hawkslade Court, Winter Garden
$447,900
3 Beds ⋅ 2.5 Baths ⋅ Storey Grove Ph 1b-3 SubDv. ⋅ 34787 Zip Code
Discover Your New Home! Welcome to your exquisite townhome in the sought-after Storie Grove community, located in the rapidly developing Hamlin area of Winter Garden. This beautifully constructed 2019 home sits on a desirable corner lot, offering modern living in a vibrant neighborhood. Key Features: Spacious and Versatile Layout: Enjoy 3 bedrooms, 2.5 baths, and a flexible room perfect for a home office or playroom, accommodating your lifestyle needs. Open Concept Design: The airy layout seamlessly connects the living, dining, and kitchen areas, creating an inviting space for family gatherings and entertaining. Stylish Kitchen: Featuring modern appliances and ample counter space, this kitchen is a chef's delight. Outdoor Enjoyment: Step onto your good-sized, fenced patio—ideal for relaxing or hosting outdoor gatherings. Convenient Two-Car Garage: Plenty of room for parking and storage, ensuring you have space for all your belongings. Prime Location: Storie Grove is situated in the heart of the Hamlin area, known for its significant growth and development. You'll find a plethora of new shops, restaurants, and recreational opportunities just moments away. Winter Garden Village, a nearby shopping hub, offers diverse dining and retail options, while the proximity to major highways makes commuting a breeze. Community Amenities: Residents enjoy access to a wealth of community amenities, including parks, walking trails, a fitness center, and a community pool. The neighborhood is family-friendly, featuring clean surroundings and a welcoming atmosphere? Educational Excellence: Families will appreciate the highly-rated schools in the area, providing excellent educational opportunities for all ages? This townhome is not just a place to live; it’s a lifestyle. Don’t miss your chance to call this beautiful property home! Schedule your private showing today.

15031 Book Club Road, Winter Garden
$642,000
4 Beds ⋅ 3 Baths ⋅ Johns Lake Pointe SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. Welcome to your future home, where elegance meets comfort. The neutral paint scheme gives the property timeless appeal. The kitchen is equipped with stainless steel appliances for a modern touch. The primary bathroom features double sinks and a separate tub and shower for added convenience, while the primary bedroom offers a spacious walk-in closet. Enjoy outdoor living with a covered patio and fenced backyard, perfect for entertaining. The interior has been freshly updated with new paint and partial flooring replacement. This home is waiting for you. Don’t miss out on this gem!

15116 Dragon Fly Court, Winter Garden
$699,000
4 Beds ⋅ 3.5 Baths ⋅ Summerlake Pd Ph 1b-A Rep SubDv. ⋅ 34787 Zip Code
Seller may consider buyer concessions if made in an offer ~ Welcome to the Summerlake community in sought-after Winter Garden and this beautiful 4-bedroom, 3.5-bath home with an INFINITY EDGE POOL, NEW A/C (2023), TILE and PERGO WATERPROOF WOOD FLOORS throughout, formal and family spaces and you are ZONED FOR TOP-RATED SCHOOLS! The mature landscaping highlighted by custom concrete edging and COVERED FRONT PORCH add to the curb appeal this home exudes and the 3-car tandem garage front access gives you plenty of parking and storage. A bright foyer opens up to versatile formal living and dining spaces - gather with family or entertain guests with ease! The natural flow brings you into a generous family room where TRIPLE SLIDING GLASS DOORS give you access to the lanai/pool and the BUILT-IN BAR area gives you a conversation piece in addition to endless storage! All of it is open to a kitchen the home chef will love featuring a casual dining space as well as breakfast bar seating under pendant lighting, STAINLESS STEEL APPLIANCES (that include a GAS STOVE!) and closet pantry for ample storage! All of your bedrooms are on the second floor including a massive must see PRIMARY SUITE, another inviting space that feels as comfortable as it is functional with DUAL WALK-IN CLOSETS offering an Evolution DELUXE CLOSET SYSTEM and a well appointed en-suite bath. Bedroom two also features an en-suite bath while bedrooms three and four share a Jack & Jill bath. Conveniently your laundry room is also on the second floor. Thoughtful landscaping around the SCREENED POOL creates a private oasis for you to enjoy for years to come and the lanai features a natural gas hookup for your grill! Also noteworthy; there is a natural gas generator hookup, Duke energy surge protection, whole home water softener, the windows are tinted and your HOA takes care of your lawn/shrubs. The Summerlake community offers an array of fantastic AMENITIES alongside fun community events. Residents can enjoy the fitness center, park, playground, community pool or tennis courts - the choice is yours! In an ideal location for easy access to shopping, dining, theme parks and everything else Central Florida is known for. Call today to schedule your tour and start making memories in your new HOME SWEET HOME!

8105 Atlantic Puffin Street, Winter Garden
$710,000
4 Beds ⋅ 2 Baths ⋅ Encore/Ovation Ph 2 SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. Welcome to your dream home in the sought-after community of Winter Garden! This beautiful 4-bedroom, 2-bathroom residence offers an open floor plan, perfect for both everyday living and entertaining. Enjoy natural light flooding the spacious living areas, and the modern kitchen that overlooks the family room, creating a seamless flow throughout. Step outside to your private oasis—a backyard spa where you can unwind after a long day. The home comes equipped with solar panels, allowing you to enjoy energy savings from day one! Located just minutes from Disney, this home is ideal for anyone seeking a balance of tranquility and proximity to top attractions. Don’t miss this opportunity to own a piece of paradise in Winter Garden!

13534 Parkfield Way, Winter Garden
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