Winter Garden/Oakland Homes under $750,000

Winter Garden/Oakland Homes under $750,000

Welcome to the vibrant communities of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This charming region is renowned for its picturesque landscapes, rich history, and a warm sense of community that makes it a perfect place to call home. With its lush parks, beautiful lakes, and the scenic West Orange Trail, residents enjoy a plethora of outdoor activities, from biking and hiking to leisurely strolls amidst nature’s beauty.

Winter Garden boasts a delightful historic downtown area, brimming with local shops, restaurants, and a thriving farmers market, all set against a backdrop of quaint architecture. The community hosts numerous events throughout the year, fostering a lively atmosphere that brings neighbors together. Just a stone’s throw away, Oakland offers a serene, small-town feel with its charming streets and friendly residents, making it an ideal retreat from the hustle and bustle of city life.

For those seeking a home in this idyllic region, you'll be pleased to discover a diverse selection of properties available for under $750,000. Whether you’re looking for a cozy single-family home, a modern townhouse, or a spacious property with a backyard oasis, Winter Garden and Oakland have something to suit every taste and lifestyle. With excellent schools, convenient access to major highways, and proximity to Orlando’s attractions, this area is perfect for families, young professionals, and retirees alike.

Explore the enchanting neighborhoods of Winter Garden and Oakland today, and find your dream home in this captivating corner of Florida!

Newest Winter Garden/Oakland Homes under $750,000

6266 Sunny Time Avenue, Winter Garden
$433,890
3 Beds ⋅ 3 Baths ⋅ O6454896 MLS ⋅ 21 BLDG.
Discover Silverleaf Oaks in Winter Garden! This new home community will feature a collection of single-family and townhomes in desirable Horizon West. Located in the heart of Orlando’s attractions, residents will enjoy an array of amenities, including a resort-style pool, cabana, and playground – without a CDD. Plus, minutes to shopping, dining, and entertaining! Introducing the Dahlia interior unit townhome, a new construction home that seamlessly combines luxury and convenience. This modern townhome features 3 bedrooms, 2 full bathrooms, a powder room, and a 2-car rear-facing garage. The first floor is designed with entertaining in mind, offering an open-concept kitchen, café, and gathering room that flow together effortlessly. The chef-inspired kitchen is a highlight, featuring a large center island, a spacious storage pantry, Elkins White cabinetry, a decorative tile backsplash, quartz countertops, and stainless-steel appliances, including a refrigerator and vented microwave. The first-floor powder room adds an extra layer of convenience for guests. The entire first floor, including the kitchen, café, and gathering room is finished with elegant tile flooring. At the end of the day, retreat to your private oasis on the second floor. The Owner’s Suite offers a spacious walk-in closet and a luxurious en suite bathroom with a double-sink, quartz-topped vanity and a glass-enclosed shower. Two additional bedrooms, a secondary bathroom, and a linen closet for added storage are located on the opposite side of the floor, ensuring privacy and plenty of space. Soft, stain-resistant Shaw brand carpet adds comfort to the stairs and bedrooms, creating a cozy atmosphere throughout. For added convenience from day one, this home comes complete with 2" faux wood blinds, as well as a brand new Whirlpool washer and dryer! With thoughtful design, high-end finishes, and a focus on everyday convenience, the Dahlia townhome is a perfect blend of style and practicality, offering a truly elevated living experience.

6266 Sunny Time Avenue, Winter Garden
6367 Argent Wood Drive, Winter Garden
$449,490
3 Beds ⋅ 3 Baths ⋅ O6454893 MLS ⋅ 19 BLDG.
Discover Silverleaf Oaks in Winter Garden! This new home community will feature a collection of single-family and townhomes in desirable Horizon West. Located in the heart of Orlando’s attractions, residents will enjoy an array of amenities, including a resort-style pool, cabana, and playground – without a CDD. Plus, minutes to shopping, dining, and entertaining! The new construction Foxtail interior unit townhome features 3 bedrooms, 2 full bathrooms, a powder room, an open concept kitchen, café and gathering room, a private courtyard, and a 2-car rear-facing garage. The first floor is ideal for entertaining, featuring a spacious gathering room, café and kitchen, with a large center island, storage pantry, white cabinetry, a decorative tile backsplash, quartz countertops, and Whirlpool stainless-steel kitchen appliances- including a refrigerator. A powder room and laundry on the first floor add to the thoughtful convenience. Enjoy entertaining loved ones from your private, fenced rear courtyard. After a long day, retreat upstairs to your private oasis. The Owner's Suite features a spacious walk-in closet and en suite bathroom with a double sink quartz-topped vanity, private water closet, and a walk-in shower. Two additional bedrooms, the secondary bathroom and extra storage offered by a linen closet are on the opposite side of the second floor, offering privacy and space for everyone. Professionally curated design finishes for this popular Foxtail townhome include wood-look luxury vinyl plank flooring throughout the first floor living areas, tile flooring in the laundry room and bathroom, and soft, stain-resistant, Shaw brand carpet in the bedrooms and second floor living areas, and so much more. This new construction townhome perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind. Schedule your tour today!

6367 Argent Wood Drive, Winter Garden
14501 Grove Resort Avenue Unit 3618, Winter Garden
$430,000
3 Beds ⋅ 3 Baths ⋅ S5160518 MLS ⋅ 3 BLDG.
WELCOME TO THE GROVE RESORT & WATERPARK, WINTER GARDENS, ORLANDO FLORIDA. THIS BEAUTIFUL FULLY FURNISHED SABLE DESIGN CONDO IS IN AN EXCELLENT LOCATION WITH GREAT VIEWS OF WATER PARK AND MUCH MORE. THIS BEAUTIFUL SABLE DESIGN CONDO IS ON THE 6TH FLOOR WITH 3 LUXURY BEDROOMS AND 3 GREAT BATHROOMS. AND GREAT VIEWS FROM SCREENED BALCONY. YOU CAN OWN THIS BEAUTIFUL VACATION CONDO AT THE GROVE RESORT THAT OFFERS PROFESSIONAL ON SITE PROPERTY MANAGEMENT SERVICES TO ALL OWNERS AND THEIR GUESTS. THE GROVE RESORT HAS MANY AMENITIES INCLUDING BUT NOT LIMITED TO A GREAT WATER PARK, LAZY RIVER, SWIMMING POOLS , WATER SLIDES, SPA, INDOOR & OUTDOOR DINING, FITNESS CENTER, LAKE AUSTION FOR FISHING AND PADDLE BOATING, SHOPPING AND MUCH MORE

14501 Grove Resort Avenue Unit 3618, Winter Garden
6129 Flowering Cherry Bend, Winter Garden
$748,018
4 Beds ⋅ 3 Baths ⋅ G5119730 MLS
Under Construction. Welcome to a home designed for easy everyday living in Avalon Woods. This single-story Anna Maria, Elevation B, offers four bedrooms and three full bathrooms across 2,235 heated square feet. A welcoming covered front porch leads into an open layout where the family room, dining area and Gourmet Kitchen bring everyone together. Prepare a favorite meal at the spacious kitchen island, with a built-in oven, cooktop and range hood close at hand, then settle in for a relaxed evening with room to spread out. The primary suite offers a quiet retreat with a spa-style shower, while three additional bedrooms provide flexibility for guests, work or hobbies. Laminate flooring adds warmth to the main living areas, with carpeted bedrooms and tile in the bathrooms. Open the sliding glass doors to the covered rear lanai and enjoy a morning coffee or an unhurried weekend. A dedicated indoor laundry room and attached two-car garage add everyday convenience. Discover the comfort and possibilities of Avalon Woods in Winter Garden. Schedule a visit to the community model home. Sample Image.

6129 Flowering Cherry Bend, Winter Garden
12542 Encore At Ovation Way, Winter Garden
$669,000
4 Beds ⋅ 4 Baths ⋅ S5159070 MLS
Fall in love with this 4-bedroom, 3.5-bath, 2,781 square foot home with 2-car ally-load garage. This versatile plan will wow you the minute you enter, with its impressive 2-story foyer. A bedroom with its own full bath is located up front, creating the perfect spot for guest, in-laws, or perhaps a home office. The chef of the home won’t feel ostracized in this kitchen; the family room, kitchen, and dining room are all open to each other, creating a perfect spot for family hangouts or weekend entertaining, keeping everyone in the mix. Enjoy a covered lanai located on the side of the home through the oversized sliding glass door. Head upstairs to find three more bedrooms and a loft. The loft is the perfect space for movie night, game day, or just a second hangout. It separates the owner’s suite in the back of the home from the secondary bedrooms, giving everyone the privacy, they deserve. The owner’s suite features two very impressive sized walk-in closets and a bathroom to match. You’ll be happy this Horizon West new home is built with features that meet the Energy Star® 3.1 home building requirements, saving you on the cost of ownership. It’s also backed by M/I Homes' industry leading 10-Year Transferable Warranty. Contact us today before it’s gone!

12542 Encore At Ovation Way, Winter Garden
8154 Common Teal Court, Winter Garden
$645,000
4 Beds ⋅ 3 Baths ⋅ O6454215 MLS
Virtually Staged. Welcome to 8154 Common Teal Court, a beautiful home in Winter Garden’s sought-after Summerlake community, where comfortable living and thoughtful design come together. Built in 2019, this single-story residence offers 4 bedrooms, 3 bathrooms, and 2,281 square feet of living space, with a collection of upgrades selected from the very beginning. The open floor plan connects the main living areas, creating a bright, welcoming space that feels just as comfortable for everyday living as it does for entertaining. The kitchen is a standout, featuring upgraded luxury cabinetry and finishes that bring a refined touch to the heart of the home. A spacious primary suite and well-appointed additional bedrooms complete the interior. Outside is where this home takes on a character of its own. Added after construction, the expansive custom deck extends beyond the covered lanai, offering plenty of room to entertain, dine outdoors, or simply unwind. And the sunsets? They're something special. With beautiful sunset views right from the deck, it's easy to imagine this becoming a favorite spot to end the day. The property also features a NEW roof (2025), and solar panels, which will be paid off by the seller at closing. Summerlake is known for its inviting neighborhood atmosphere and community amenities, including a resort-style pool, fitness center, parks, and recreational spaces. Just minutes away, the Hamlin district offers a growing collection of restaurants, shops, entertainment, and everyday conveniences. Downtown Winter Garden, major roadways, and Orlando's attractions are also within easy reach. Between the upgraded interiors, the outdoor living space, and those beautiful evening views, 8154 Common Teal Court has a lot to offer in one of Winter Garden's most desirable locations.

8154 Common Teal Court, Winter Garden
Winter Garden
$239,900
3 Beds ⋅ 1 Baths ⋅ O6454154 MLS
Welcome to Winter Garden! This charming 3-bedroom home offers 815 square feet of comfortable living space and is full of updates. The beautifully renovated kitchen features shaker cabinetry, granite countertops, and a stylish stacked stone backsplash. Fresh interior and exterior paint give the home a clean, refreshed feel. TILE THROUGHOUT! NO CARPET! The roof was replaced in 2023, offering added peace of mind. A one-car carport provides convenient covered parking. Enjoy the freedom of NO HOA and a convenient location just a short stroll to Zanders Park & minutes from Plant Street and historic downtown Winter Garden, with its popular restaurants, shopping, entertainment, farmers market, and West Orange Trail. Whether you're a first-time buyer, downsizing, or looking for an investment opportunity, this home is worth a look! Do not miss this opportunity, schedule your private tour today!!!

Winter Garden
159 9th Street, Winter Garden
$369,900
3 Beds ⋅ 2 Baths ⋅ O6453622 MLS
Enjoy the best of Winter Garden living in this beautifully built 2024 home! This property features 3 bedrooms, 2 bathrooms, with 1,188 square feet of thoughtfully designed living space. The home features an open-concept floor plan that creates a bright and welcoming atmosphere with LPV throughout. The spacious kitchen is the heart of the home, showcasing a large island, shaker cabinetry, granite countertops, and stainless steel appliances. The primary suite has a spa-like feel with en-suite bathroom and walk-in closet. Enjoy the convenience of a one-car garage and a covered patio, perfect for relaxing outdoors. NO HOA! Ideally located near all that downtown Winter Garden has to offer, including shopping, dining, entertainment, and the popular West Orange Trail. Modern construction, a convenient location, and the freedom of no HOA make this home one you won't want to miss!

159 9th Street, Winter Garden
14347 Braemar Street, Winter Garden
$493,000
4 Beds ⋅ 3 Baths ⋅ O6451972 MLS
Built in 2024 by Meritage Homes, this pristine 4-bedroom, 2.5-bathroom bungalow in Horizon West’s Highland Ridge delivers energy-efficient modern living at its finest. The open-concept first floor boasts high ceilings, durable tile flooring, and a chef’s kitchen equipped with a large prep island, solid-surface counters, 42” cabinetry, and stainless steel appliances. All 4 bedrooms and the laundry room are conveniently located upstairs, headlined by a primary retreat with an oversized walk-in closet and dual-sink ensuite bath. Built with advanced spray-foam insulation, high-performance windows, and smart features for peak comfort and utility savings. Enjoy community pool access, cabana, and tot lot, with immediate proximity to SR-429, Flamingo Crossings shopping and dining, top-rated schools, and Walt Disney World.

14347 Braemar Street, Winter Garden
14517 Black Lake Preserve Street, Winter Garden
$600,000
4 Beds ⋅ 3 Baths ⋅ O6453142 MLS
Welcome to Black Lake Preserve – Winter Garden Living at Its Best! Discover the lifestyle and convenience of one of Winter Garden’s most desirable gated communities. Nestled within the intimate, friendly neighborhood of Black Lake Preserve, featuring just 92 homes, this beautifully maintained residence offers a wonderful combination of comfort, space, and location. Enjoy community amenities including a playground and scenic walking trails, all within a welcoming neighborhood setting. Even better, the home's entire exterior will be freshly repainted, providing a refreshed look and added curb appeal for its next owners! Built in 2016, this thoughtfully designed home features an inviting open-concept floor plan with plenty of room to live, work, and entertain. As you enter, you are welcomed by a formal living room or private office to the right and a separate dining area to the left. The spacious kitchen serves as the heart of the home, showcasing granite countertops, a beautiful backsplash, stainless steel appliances, a gas cooktop, upgraded 48-inch cabinetry, and an oversized walk-in pantry. The kitchen flows seamlessly into the expansive family room, creating the perfect gathering space for everyday living and entertaining. The private primary suite offers abundant natural light, an extra-large walk-in closet, dual vanities, a relaxing garden tub, and a separate step-in shower. Three additional bedrooms are thoughtfully positioned on the opposite side of the home, providing privacy and flexibility for family, guests, or a home office. A full secondary bathroom, an additional guest bathroom near the front of the home, and a spacious laundry room complete this functional layout. Location is everything, and this home delivers! Minutes from SunRidge Elementary and Middle Schools, while just minutes from Historic Downtown Winter Garden, where you'll find charming shops, local dining, parks, and community events. With easy access to Florida's Turnpike, FL-429, and SR-408, commuting to Downtown Orlando, major employment centers, and Central Florida's world-famous theme parks is a breeze. Whether you're looking for a place to grow, entertain, or simply enjoy everything Winter Garden has around it, this home is ready to welcome you. Schedule your private showing today and discover your next chapter at Black Lake Preserve. Your HOME SWEET HOME awaits!

14517 Black Lake Preserve Street, Winter Garden
8877 Lakeshore Pointe Drive, Winter Garden
$650,000
4 Beds ⋅ 4 Baths ⋅ O6454023 MLS
Welcome to this stunning, completely remodeled home in beautiful Winter Garden! Offering 4 spacious bedrooms, 3.5 luxurious bathrooms, and a separate guest house. This exceptional property combines elegance, comfort, and versatility. The home features a gorgeous interior courtyard, creating a beautiful private setting perfect for relaxing or entertaining. Inside, you’ll find soaring ceilings throughout, an elegant and inviting living space, and a chef-inspired kitchen equipped with state-of-the-art appliances and exquisite finishes. The spacious bedrooms include comfort and privacy, while the luxurious primary suite features a spa-inspired bathroom with a beautiful soaking tub, an elegant walk-in shower, and generous closet space. Every detail has been thoughtfully designed to create an elegant yet welcoming atmosphere. With its complete renovation, stunning architectural features, private courtyard, and separate guest residence, this extraordinary Winter Garden home offers a truly special living experience.

8877 Lakeshore Pointe Drive, Winter Garden
8900 Sonoma Coast Drive, Winter Garden
$745,000
3 Beds ⋅ 3 Baths ⋅ S5160445 MLS
Enjoy resort-style living in Waterleigh, a master-planned community in Horizon West, Winter Garden. This single-story home offers 3 bedrooms, 2 full bathrooms, a half bathroom, and a separate office, complemented by distinctive interior finishes and expansive outdoor living spaces. An inviting foyer features decorative wood slat accents, integrated lighting, and a floating bench. The open-concept living area showcases a tray ceiling, wood-look tile flooring, and a custom TV feature wall with a floating media console. The kitchen features cabinetry, stone countertops, a tile backsplash, pendant lighting, and a stainless steel appliance package, including a refrigerator, built-in oven, microwave, cooktop, and dishwasher. A separate dining area provides additional gathering space. The office features glass French doors, built-in cabinetry, shelving, and work surfaces. The primary suite includes custom closet organizers and an en-suite bathroom with dual sinks, illuminated mirrors, a separate shower, a soaking tub, and a private water closet. The laundry room includes a washer and dryer, while the garage offers extensive storage cabinetry and a coated floor. Step outside to a covered, screened lanai overlooking an expansive paver patio with a fire pit, fenced backyard, and wooded backdrop—an inviting setting for relaxing or entertaining. Waterleigh offers community pools, clubhouses, fitness facilities, playgrounds, and recreational amenities in a scenic setting of lakes and ponds. Enjoy convenient access to shopping and dining at nearby Hamlin, Publix within the community, historic Downtown Winter Garden, and SR-429. Nearby schools include Atwater Bay Elementary, Water Spring Middle, and Horizon High School; buyers should verify current school assignments with Orange County Public Schools. Kitchen appliances, washer, and dryer are included in the sale. Furnishings shown in the photographs are actual furnishings. Select photographs have been digitally enhanced for lighting, and flames have been digitally added to the outdoor fire pit.

8900 Sonoma Coast Drive, Winter Garden
Start Your Search

How much is your home worth?

Get instant property value now!