Winter Garden/Oakland Homes with Bungalow Architectural style

Winter Garden/Oakland Homes with Bungalow Architectural style

Welcome to Winter Garden and Oakland, two charming communities nestled in the heart of Orange County, Florida. Known for their rich history and vibrant atmosphere, these areas offer a unique blend of small-town charm and modern conveniences, making them a perfect place to call home.

Winter Garden, with its picturesque downtown, is a hub of activity, featuring delightful shops, cafes, and a farmers market that draws locals and visitors alike. The historic district is adorned with beautiful parks and scenic trails, perfect for an afternoon stroll or a leisurely bike ride. Just a stone's throw away, Oakland boasts a serene, close-knit community feel, where residents enjoy the tranquility of nature while still being in proximity to urban amenities.

When it comes to housing, Winter Garden and Oakland are known for their enchanting bungalows. These architectural gems exude character and warmth, often featuring inviting front porches, open layouts, and charming details that reflect the area's history. Bungalows are perfect for those seeking a cozy, intimate space that blends indoor and outdoor living. With lush gardens and friendly neighborhoods, these homes create a welcoming environment for families, retirees, and everyone in between.

Whether you’re drawn to the historic charm of Winter Garden or the peaceful allure of Oakland, the bungalow-style homes here offer a unique opportunity to experience a lifestyle steeped in comfort and community. Discover your dream home in this beautiful region, where every day feels like a getaway!

Newest Winter Garden/Oakland Homes with Bungalow Architectural style

$499,999
3 Beds ⋅ 3 Baths ⋅ Watermark SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained home in the highly sought after Watermark at Horizon West community! This spacious two story residence offers 3 bedrooms, 2.5 bathrooms, and over 2,000 square feet of thoughtfully designed living space. The open concept floor plan is perfect for both everyday living and entertaining, featuring wood tile flooring throughout the main level, abundant natural light, and a modern kitchen complete with built in appliances, ample cabinetry, generous counter space, and a large island overlooking the living and dining areas. Upstairs, you'll find a versatile loft that makes an ideal home office, media room, or play area, along with a spacious primary suite featuring a walk in closet and an en-suite bath. Two additional bedrooms, a full bath, and an upstairs laundry room complete the second floor. Enjoy Florida living from the welcoming front porch while taking advantage of the home's rear entry two car garage and low maintenance yard. Residents of Watermark enjoy resort style amenities including a community pool, fitness center, tennis courts, playground, parks, walking trails, and beautifully maintained common areas. You’re also within close distance to restaurants and just a short drive to Disney, shopping, and everything Winter Garden and Horizon West have to offer. If you’re looking for a clean, move in ready home in a great location with a strong lifestyle, this one checks all the boxes!

14543 Golden Harbor Lane, Winter Garden
$549,900
3 Beds ⋅ 3 Baths ⋅ Highland Rdg Ph 2 SubDv. ⋅ 34787 Zip Code
Welcome to this bright and inviting 3-bedroom, 2.5-bath home in the Highland Ridge community of Winter Garden. It feels open and comfortable the moment you walk in. The beautiful porcelain title throughout the first floor already gives the perspective of the open floor plan. Right off the entry is a flexible room currently used as a home office — a great spot for work or study that connect to the kitchen. The living room has high ceilings that make the space feel bigger and brighter, and it's by the dining area and kitchen. The gourmet kitchen is a real highlight, with white cabinets, a large island for cooking, cooktop and other stainless steel appliances, and those nice geometric pendant lights. Sliding glass doors open out to the backyard, so the whole main floor feels connected to the outdoors. With extended pavers and a privacy fence in the back, turning the outdoor space into a finished patio area that’s ready for grilling and relaxing and plus a covered area that goes to the 2 car detached garage. Upstairs you’ll find a spacious primary suite bedroom, plus two more comfortable bedrooms, laundry room and loft . Everything feels clean, light, and move-in ready. Highland Ridge has some really nice amenities right in the neighborhood: a pool with a cabana, playground, basketball court, and pickleball. It’s the kind of place where kids can walk over to play and adults can unwind without getting in the car. The location is convenient too. You’re just minutes from Disney World and Flamingo Crossings for shopping and restaurants, with easy access to the 429. Nearby schools include Water Spring Elementary and Middle, and Horizon High. Downtown Winter Garden, with its farmers market and Plant Street shops, is a short drive away. This home offers a good mix of modern comfort, useful living spaces, and a friendly community feel. If you’re looking for something that already feels like home, this one is worth seeing.

14099 Frasier Street, Winter Garden
$519,995
3 Beds ⋅ 3 Baths ⋅ Encore/Ovation Ph 3 SubDv. ⋅ 34787 Zip Code
A Rare Opportunity in Encore at Ovation! This beautifully upgraded Jensen model is back on the market! Located just off Disney's Western Way, this exceptional home offers timeless designer finishes, an open-concept floor plan, and an unbeatable location just minutes from Walt Disney World. The stunning kitchen features 42-inch shaker cabinets, quartz countertops, an oversized island, dovetail drawers, and upgraded lighting. Waterproof wood-look flooring flows throughout the main level, while extra-height baseboards add a custom touch. The spacious primary suite includes a tray ceiling and a luxurious bath with a designer-tiled walk-in shower and semi-frameless glass enclosure. Bathrooms feature granite countertops and slate-look porcelain tile, with plush carpeting upstairs. A standout feature is the private backyard exclusive to this floor plan creating the perfect space to relax or entertain. Walt Disney World and Margaritaville Resort Orlando are both nearby, as well as premier shopping, dining, and entertainment. Don't miss this opportunity to own one of Encore at Ovation's most desirable homes. Schedule your private showing today!

13879 Lanyard Way, Winter Garden
$525,090
3 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks SubDv. ⋅ 34787 Zip Code
Under Construction. 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 Benton bungalow, a brand-new home that includes 3 spacious bedrooms, 2 full bathrooms, a powder room, and a 2-car rear-load attached garage. The heart of the home is the open-concept kitchen, café, and gathering room, all bathed in natural light. This inviting space is perfect for both everyday living and entertaining. The kitchen boasts a large center island, a convenient storage pantry, and top-of-the-line Whirlpool stainless steel appliances—including a refrigerator. White cabinetry, decorative tile backsplash, and quartz countertops complete the sophisticated look. For added convenience, the first floor includes a powder room and coat closet. Upstairs, you’ll find the private owner’s suite, two additional bedrooms, a second full bathroom, and the laundry room. The owner’s suite is a true retreat, featuring a walk-in closet and a luxurious en suite bathroom with a frameless glass-enclosed shower, quartz-topped dual vanity, and linen closet. Throughout the first floor, enjoy the beauty of Wood-Look Luxury Vinyl Plank flooring, while tile enhances the laundry room and bathrooms. Plush, stain-resistant Shaw carpet covers the stairs and bedrooms, adding comfort and style. This new construction home perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind.

16827 Evermore Alley, Winter Garden
$537,290
3 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks SubDv. ⋅ 34787 Zip Code
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 Haddock bungalow, a brand-new home that combines modern design and ultimate comfort, featuring 3 spacious bedrooms, 2 full bathrooms, a powder room, and a 2-car rear-load attached garage. The heart of the home is the open-concept kitchen, café, and gathering room, all bathed in natural light. This inviting space is perfect for both everyday living and entertaining. The kitchen boasts a large center island, a convenient storage pantry, and top-of-the-line Whirlpool stainless steel appliances—including a refrigerator and vented microwave. Tilden white cabinetry, decorative tile backsplash, and quartz countertops complete the sophisticated look. For added convenience, the first floor includes a powder room and coat closet. Upstairs, you’ll find the private owner’s suite, two additional bedrooms, a second full bathroom, a loft, and a laundry closet. The owner’s suite is a true retreat, featuring a walk-in closet and a luxurious en suite bathroom with a frameless glass-enclosed shower, quartz-topped dual vanity, private water closet, and linen closet. Throughout the entire first floor enjoy wood-look luxury vinyl plank flooring, while tile flooring spans the laundry room and bathrooms. Plush, stain-resistant Shaw carpet covers the stairs, loft, and bedrooms, adding comfort and style. Smart home features include a smart thermostat, a smart doorbell, and additional LED downlights—ensuring your home is as connected as it is stunning. This new construction home perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind.

16803 Evermore Alley, Winter Garden
$584,000
4 Beds ⋅ 3 Baths ⋅ Serenade At Ovation SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to your Newbury model home! This Dream Finders Home is a 4-bedroom, 3-bathroom that offers 2,083 square feet! This PREMIUM CORNER LOT next to conservation area and Lake View from primary suite. This home has a beautifully upgraded living space in a desirable area of Winter Garden. The neighborhood of Serenade at Ovation offers Elevation C which is the upgraded elevation with a more desirable curb appeal that includes stone veneer. The heart of the home features a modern kitchen with upgraded cabinets, backsplash tile and stylish light fixtures extending into the breakfast nook. This lot is near the conservation area and lake view from primary suite window. Throughout the house, you'll find upgraded light fixtures and enhanced lighting in the living room, creating a warm and inviting atmosphere. Tile throughout the 1st floor was a BUILDER UPGRADE! This primary bathroom boasts upgraded faucets, tile, and cabinets! The wood grain adorns the staircase instead of traditional carpet for an elegant touch. Every window is dressed in upgraded wood blinds as a BUILDER UPGRADE, and fresh upgraded paint brightens all interior rooms. Practical upgrades include an enhanced sink and cabinet in the laundry room; plus, extra light sockets strategically placed in the living room and additional prewiring in the upstairs bonus room for your convenience. Upgraded utility sink and cabinets in laundry room on the 2nd floor. This thoughtfully upgraded home combines comfort, style, and functionality in a prime location. The attention to detail in every room, from the kitchen upgrades to the enhanced lighting throughout, creates a move-in ready property that's perfect for modern living. This neighborhood offers excellent connectivity with nearby transportation options and shopping conveniences. The proximity to quality educational facilities, including Horizon High School just minutes away, adds to the home's appeal. The area provides easy access to recreational opportunities, with Disney Theme parks and entertainment venues within a short drive. Brand New Publix, Miller's Alehouse in shopping plaza nearby. Enjoy Winter Garden's local history and charm! Bonus: includes high-speed fiber optic internet!. Home is currently rented through 10/31/2026 current rental rate is $3,000.00.

13043 Serene Glade Road, Winter Garden
$555,000
3 Beds ⋅ 3 Baths ⋅ Serenade/Ovation Ph 1 SubDv. ⋅ 34787 Zip Code
Exquisite Model Home Investment Opportunity | Just Minutes from Disney Experience the perfect blend of luxury, elegance, and investment potential with this exceptional Dream Finders Homes Model Residence, located in one of Central Florida's newest and most desirable communities. Situated on a premium corner homesite, this beautifully appointed 3-bedroom, 2.5-bath home showcases every detail today's discerning buyer is looking for. Professionally designed and loaded with the builder's finest upgrades. From the moment you enter, you'll appreciate the bright open-concept floor plan, soaring ceilings, abundant natural light, and designer finishes throughout. The spectacular gourmet chef's kitchen is the centerpiece of the home, featuring: • Elegant quartz countertops • Premium cabinetry • Stainless steel appliances • Spacious center island perfect for entertaining • Designer lighting package • Luxury finishes throughout The expansive owner's suite offers a spa-inspired retreat complete with dual vanities, quartz countertops, a large walk-in shower, and generous walk-in closet space. Additional features include: 3 Bedrooms 2.5 Bathrooms Premium Corner Lot All Kitchen Appliances Included Luxury Upgrades Throughout Covered Outdoor Living Space Energy-Efficient Construction Outstanding Investment Opportunity One of the most unique features of this property is that it is currently being utilized by Dream Finders Homes as their professionally decorated Model Home. The builder is presently paying $4,486 monthly to lease the property back from the owner, allowing the new purchaser to assume an attractive income-producing opportunity while the builder continues operating the home as its sales model, subject to the terms of the existing lease. Whether you're looking for a luxury primary residence or an exceptional investment with immediate rental income, this property offers a truly rare opportunity. Community Highlights • Low HOA • No CDD • Brand-new community • Minutes from Walt Disney World Resort • Convenient access to shopping, dining, entertainment, and major highways This is far more than a home—it's a luxury lifestyle combined with an exceptional investment opportunity. Schedule your private showing today and discover why this extraordinary Model Home stands above the rest.

13006 Serene Glade Road, Winter Garden
$539,790
4 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks SubDv. ⋅ 34787 Zip Code
Under Construction. 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 quick move-in Haddock bungalow features our CO1 exterior, Move-In Ready appliance and window blind package, our Luxe Fresh design package, 3 bedrooms, 2 full bathrooms, a powder room, loft and 2-car detached garage. The first floor is ideal for entertaining, with its combined gathering room, kitchen, café, powder room, and gorgeous Oceanfront wood-look luxury vinyl plank flooring. The kitchen features a center island, storage pantry, stainless steel Whirlpool appliances, white cabinets, a white herringbone tile backsplash and Lyra quartz countertops. The second floor offers privacy and space for everyone with the owner’s suite, two additional bedrooms, the second bathroom, the laundry room and loft. Your owner’s suite features a walk-in closet, en suite bathroom with a private water closet, linen closet, walk-in shower with a frameless glass door, and dual sink quartz-topped white vanity. Professionally curated design selections for this home include our FH1 exterior, Move-In Ready appliance and window blind package and Luxe Fresh design package: upgraded 42" soft close white cabinets, a white herringbone tile kitchen backsplash, Lyra quartz countertops, white Brescia porcelain tile flooring in the wet areas, and soft, stain-resistant Ornamental Gate carpet in the bedrooms and second floor living areas.

16681 Silver Brook Way, Winter Garden
$524,990
3 Beds ⋅ 3 Baths ⋅ Serenade At Ovation SubDv. ⋅ 34787 Zip Code
Major Price Improvement!! Take advantage of the 4.99% interest rate (call for details) with a 2% credit towards buyers closing costs!!! Welcome to Serenade at Ovation, one of Winter Garden's most desirable new home communities, where modern design meets an unbeatable Central Florida lifestyle. This completed brand-new Cooper floor plan offers 2,078 square feet of thoughtfully designed living space with 3 bedrooms, 2.5 baths, a versatile loft, and a 2-car garage, all perfectly positioned with the front of the home overlooking peaceful conservation views. The open-concept layout is ideal for both everyday living and entertaining. At the heart of the home, the gourmet kitchen showcases beautiful quartz countertops, elegant linen cabinetry, and abundant workspace while seamlessly connecting to the spacious dining and living areas. Stunning level-three natural wood-look plank tile flooring flows throughout the first floor, creating warmth, durability, and timeless appeal. Upstairs, the spacious primary suite serves as a private retreat featuring a large walk-in closet, dual-sink vanity, and oversized walk-in shower. Two additional bedrooms, a full bath, and a flexible loft provide plenty of space for a home office, media room, playroom, or additional gathering area. Modern finishes, energy-efficient construction, and thoughtful design details throughout make this home truly move-in ready. Residents of Serenade at Ovation enjoy an exceptional location in the heart of Winter Garden, one of Central Florida's fastest-growing and most sought-after communities. Just minutes away, Historic Downtown Winter Garden offers charming brick-lined streets, boutique shopping, farmers markets, live entertainment, and an impressive selection of local restaurants, cafés, breweries, and outdoor dining options. Nearby Winter Garden Village provides convenient access to popular retailers, grocery stores, fitness centers, and everyday conveniences. Outdoor enthusiasts will appreciate close proximity to the award-winning West Orange Trail, numerous parks, lakes, golf courses, and recreational opportunities throughout the area. Families and professionals alike will enjoy the community's convenient access to major roadways including State Road 429, Florida's Turnpike, State Road 535, and Interstate 4, providing quick connections to Downtown Orlando, Disney, Orlando International Airport, and the region's major employment centers, entertainment destinations, and attractions. Experience the perfect combination of contemporary living, natural surroundings, and unmatched convenience in this exceptional new home at Serenade at Ovation.

13023 Tranquil Water Alley, Winter Garden
$679,000
4 Beds ⋅ 4 Baths ⋅ Osprey Ranch Ph 1 SubDv. ⋅ 34787 Zip Code
Welcome to this beautiful bungalow-style home in the highly desirable Osprey Ranch community in Winter Garden! Featuring 4 bedrooms, 3 full bathrooms, and 1 half bath, this thoughtfully designed residence offers comfort, style, and functionality for the whole family. Located just minutes from Disney, shopping, dining, and major highways, this home combines convenience with a peaceful neighborhood feel. Enjoy spacious living areas, modern finishes, and a layout perfect for entertaining or everyday living. Situated in a prime location with access to highly rated schools, this property is ideal for families looking for both lifestyle and location. Don’t miss the opportunity to live in one of Winter Garden’s most sought-after communities!

15174 Field Daisy Drive, Winter Garden
$599,000
4 Beds ⋅ 3 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code
Such a Charming, Family-Friendly 4 Bedroom 2.5 Bath Home in Beautiful Winter Garden. The bungalow-style porch is extremely inviting as you enter the home. Arched doorways, recessed lighting, French doors, transom windows, and a separate office on the first floor. Tons of natural lighting. The kitchen includes solid granite countertops, solid wood cabinetry, custom tile backsplash, and an island storage prep station. and a Pantry! Oversized primary bedroom upstairs, with an ensuite bathroom leading to a roomy walk-in closet with pocket doors. Ensuite Bath includes a glass-walled shower with a separate spa-style tub. Dual sinks with plenty of counter space. Solid wood cabinetry and Stone countertops. 3 additional Bedrooms on the second floor. Full laundry room with cabinetry. Welcome to Independence, one of the most desirable communities in Central Florida! Ideally located within walking distance of A-rated schools, shopping, dining, and fun for the whole family. Whether envisioning a pool, an expanded patio, or simply more room to relax and play, this space is a true standout in the neighborhood. Residents of Signature Lakes enjoy resort-style amenities including two clubhouses, tennis and basketball courts, two swimming pools, dog parks, scenic walking and biking trails, and beautifully landscaped green spaces. These neighborhoods would be inspired by the traditional aesthetic of Colonial America, with streets named after agricultural methods, explorers, authors, artists, and more. The "icon" for the community is the Mall, situated at the entrance to the community off Ficquette Rd. Two large stone obelisks, alight with gas torches in the evening, give way to the sparkling 512-foot reflecting pond surrounded by emerald green lawn and stately mature oak trees. At the Tower Green stands the five-story brick Clock Tower, trimmed by ornamental gardens and capped with a copper spire. The Town Square Residents Club ends the Mall, with its colonnaded façade and tall cupola drawing inspiration from Georgian colonial buildings of historic Philadelphia, New York, and Boston. This prime Winter Garden location offers quick access to SR-429 and is minutes from shopping, dining, and entertainment. This home is the perfect blend of style, comfort, and location, and is ready to welcome its next owner. At Independence, they are proud to be among the finest master planned communities in Horizon West. Full of dramatic architectural flourishes, surrounded by the majesty of natural Florida, and home to a lifestyle that's second to none, we welcome you to explore this beautiful community and discover that this unique place truly is what life should be.

6316 Manuscript Street, Winter Garden
$538,990
3 Beds ⋅ 3 Baths ⋅ Serenade At Ovation SubDv. ⋅ 34787 Zip Code
Virtually Staged. Discover the Copper, an open bungalow floor plan that will enhance your living experience with its spacious layout, including 3 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The moment you walk through the front door, the openness of the home welcomes you, leading directly to a show-stopping gourmet kitchen with a long island ideal for entertaining friends and other guests. Upstairs, the primary suite offers a perfect end-of-day retreat with a large walk-in closet and a generously sized bedroom. Introducing Serenade at Ovation, within the fast-growing Horizon West community, offers a prime location near top Winter Garden schools, Walt Disney World, Hwy 192, SR 429, Flamingo Crossings, and Hamlin. The diverse housing options include townhomes, new bungalows, and award-winning single-family homes, providing affordable living in this burgeoning area. Abundant green spaces, pocket parks, and the central Area Community Park with its engineered wood fiber playground, shaded pavilion, and dog parks, make this community an ideal, family-friendly choice at the heart of Horizon West.

13019 Serene Glade Road, Winter Garden
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