Winter Garden/Oakland Homes with Florida Architectural style

Winter Garden/Oakland Homes with Florida Architectural style

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This charming area is renowned for its vibrant community, rich history, and picturesque landscapes, making it an ideal destination for families, retirees, and everyone in between. With its warm climate, lush greenery, and stunning sunsets, Winter Garden and Oakland offer a perfect blend of suburban tranquility and urban convenience.

As you explore this delightful region, you’ll find a diverse array of homes that beautifully embody Florida’s architectural style. From classic Mediterranean villas adorned with terracotta tiles to charming bungalows featuring breezy porches, the homes in Winter Garden and Oakland reflect the unique character of Florida living. Many residences are designed to embrace the outdoors, with spacious backyards and inviting patios that encourage alfresco dining and relaxation under the sun.

The community is also brimming with amenities, including scenic parks, vibrant farmers markets, and a charming historic downtown filled with boutique shops and delightful eateries. Outdoor enthusiasts will appreciate the proximity to Lake Apopka and the West Orange Trail, perfect for hiking, biking, and enjoying the stunning natural beauty of the area.

Whether you’re drawn to the captivating architecture or the warm sense of community, Winter Garden and Oakland offer a lifestyle that is both inviting and enriching. Discover your dream home in this idyllic region, where Florida charm meets modern living, and experience the best that life has to offer.

Newest Winter Garden/Oakland Homes with Florida Architectural style

3 Beds ⋅ 3 Baths ⋅ Hamlin Meadows SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Porter floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath, alongside two additional bedrooms. Downstairs, the open-concept layout connects the great room to the dining area, making it perfect for entertaining or gatherings. The covered lanai offers a cozy outdoor retreat, ideal for relaxing at the end of the day. Completing the home is a detached two-car garage, ensuring ample parking and storage. The Porter floor plan offers modern living tailored to meet everyday needs with style and functionality.

7276 Windy Willow Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hamlin Meadows SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath, alongside two additional bedrooms. Downstairs, the open-concept layout connects the great room to the dining area, making it perfect for entertaining or family gatherings. The covered lanai offers a cozy outdoor retreat, ideal for relaxing at the end of the day. Completing the home is a detached two-car garage, ensuring ample parking and storage. The Harbor floor plan offers modern living tailored to meet everyday needs with style and functionality.

7272 Windy Willow Street, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Westfield Lakes SubDv. ⋅ 34787 Zip Code

Welcome Home! Meticulously maintained home boasting with upgrades on an oversized conservation lot with peaceful pond views. Designed for both everyday living and entertaining, features a completely remodeled kitchen with quartz countertops, premium Café appliances, designer backsplash, a massive island with sitting space, upgraded lighting and a custom walk-in pantry. The first floor includes a private office, spacious family room, guest suite with a full bath, laundry room, formal living, and dining room. Porcelain tile flows throughout the main living areas, French doors lead to your private backyard retreat with a fully screened lanai overlooking the saltwater pool and spa, complete with new tile. Upstairs you'll find a stunning media room complete with theater seating and a granite wet bar, 4 bedrooms and a full bath. The primary suite features tray ceiling, plantation shutters, dual walk-in closets, and remodel ensuite bath. Updates include dual vanities, walk-in glass shower, clawfoot tub, and stunning upgraded tile throughout. Two car garage with an upgraded paver driveway. Located in a highly sought-after community of Westfield Lakes. Excellent public schools and convenient access to shopping, dining, and major highways, this exceptional home offers the perfect combination of luxury, comfort, and location. Schedule a private showing today!

626 English Lake Drive, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Lakeview Pointe/Horizon West P SubDv. ⋅ 34787 Zip Code

Great house fronting the park, gym, and community pool. Tons of upgrades inside and out. Beautiful screened pool with motorized shade for privacy on patio. Saltwater pool. Luxury Vinyl Plank throughout the house. NO Carpet! Kitchen has lots of upgrades as well. KitchenAid appliances. Wall oven and cooktop. Samsung refrigerator included. Washer and Dryer also stay! 5 mounted TV's will convey as well! Ring alarm system with cameras as well. Plantation shutters throughout.

14048 Lake Abbotts Drive, Winter Garden

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

5 Beds ⋅ 4 Baths ⋅ Johns Landing Ph 01 44/47 SubDv. ⋅ 34787 Zip Code

Virtually Staged. BRAND NEW ROOF! This five-bedroom, three-and-a-half-bathroom residence sits in a gated community with a new roof and architectural shingles, offering security and peace of mind. The property combines thoughtful interior finishes with direct access to some of the area's most desirable outdoor recreation opportunities. Inside, the kitchen features stainless steel appliances and a custom tile backsplash above stone countertops, with a breakfast nook for casual dining. The primary suite includes a picture window and rich wood flooring, complemented by crown molding throughout the residence. The great room flows across ceramic tile and polished wood surfaces, while the formal dining room showcases gleaming wood floors. An upstairs loft with natural wood planks provides flexible space for an office, playroom, or media area. The laundry room features ceramic tile for easy maintenance and durability. A smart thermostat manages climate control efficiently throughout all living areas. The covered front porch creates an inviting entrance, and mature landscaping frames the property with established trees and plantings that provide natural privacy and curb appeal. The location offers exceptional convenience and recreation. You're minutes from Downtown Winter Garden, with easy connectivity to the Florida Turnpike for broader travel throughout Central Florida. The West Orange Trail is nearby for outdoor enthusiasts seeking biking and nearby paths, and the community boat ramp provides direct waterfront entry to John's Lake for boating and fishing. The Oakland Nature Preserve is close by, offering natural spaces to explore with nearby trails and wildlife viewing opportunities. Whether you're seeking waterfront recreation, trail connectivity, or proximity to local commerce and dining, this address delivers on multiple fronts. Schedule a showing today to experience this property and its neighborhood firsthand.

706 Strihal Loop, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Lake Forest Sec 10a SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully designed 5-bedroom, 4-bath home located in a gated Winter Garden community, offering an exceptional blend of elegant finishes, functional living spaces, and resort-style outdoor living. With soaring ceilings and an inviting open entry, this home is filled with architectural details including crown molding, coffered and tray ceilings that add character throughout. Designed for both everyday living and entertaining, the thoughtfully crafted floor plan offers formal living and dining areas while maintaining an open flow between the kitchen and family room. Tile flooring extends through the main living areas and luxury vinyl in the primary suite and entire upstairs, providing both style and durability. The spacious kitchen serves as the heart of the home with granite countertops, abundant cabinetry, generous counter space, bar seating, a separate dinette, and seamless views into the family room. Expansive pocket sliding glass doors create a true indoor-outdoor living experience, opening the family room to the covered lanai and pool area—perfect for entertaining family and friends. The first-floor primary suite is a private retreat featuring abundant natural light, direct access to the lanai, dual walk-in closets, separate vanities, a walk-in shower, and a relaxing soaking tub. A dedicated office with built-in shelving and closet space provides an ideal work-from-home setup. Two additional bedrooms and bathrooms are also located downstairs, including a private en-suite with direct access to the pool. Upstairs offers exceptional flexibility with a spacious loft that can serve as a second living area, game room, or playroom, along with a fourth bedroom and full bath. A fifth bedroom is currently configured as a media room with surround sound and projector hookups, making it ready for movie nights or easily converted back to a bedroom. Step outside to your own backyard retreat featuring a sparkling pool with a natural rock waterfall, a unique swim-up table, and a spacious covered lanai. The fully fenced backyard provides both privacy and room to relax, play, or entertain. Additional highlights include a three-car garage and an ideal location just minutes from Winter Garden Village, offering shopping, grocery stores, restaurants, and healthcare. With convenient access to SR-429 and Historic Downtown Winter Garden, this home combines the comfort of a gated community with easy access to everything Central Florida has to offer.

13624 Larsen Lane, Winter Garden

5 Beds ⋅ 4 Baths ⋅ West Lake Hancock Estates SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully maintained 5-bedroom, 3-bath home with a dedicated office, offering the perfect blend of elegance, comfort, and functionality in the highly desirable Overlook at Hamlin community of Winter Garden. Thoughtfully designed for today's lifestyle, this spacious floor plan features a sought-after first-floor primary suite, providing a private retreat with convenience and flexibility. Improvements include: NEW Carpet, NEW Water Heaters with warranties, 1 NEW HVAC with warranty and regular service, NEW Interior Paint, Exterior refreshed a couple years ago. Transferrable Termite Bond. From the moment you enter, you'll appreciate the pride of ownership evident throughout. Gorgeous wood flooring flows through the main living areas, complemented by brand-new carpet and fresh interior paint for a truly move-in-ready feel. The dedicated office is ideal for working from home, studying, or creating a quiet flex space. The heart of the home is the open-concept living area, where a beautiful gas fireplace creates a warm and inviting focal point. The spacious kitchen overlooks the family room and dining area, making it easy to entertain while staying connected with family and guests. Step outside to one of the home's standout features—an oversized covered lanai and an expansive screened enclosure that extends your living space outdoors. Whether you're enjoying your morning coffee, dining al fresco, or hosting gatherings, this incredible outdoor retreat is designed for year-round Florida living. Upstairs, you'll find generously sized secondary bedrooms that provide plenty of space for family and guests, while the thoughtful layout offers privacy and versatility for every stage of life. Located in the sought-after Hamlin area, residents enjoy exceptional resort-style amenities, including a private community boat ramp with access to Lake Hancock, a lakeside clubhouse, fitness center, community pool, playgrounds, parks, walking trails, and waterfront recreation. Just minutes from Hamlin Town Center, Walt Disney World, shopping, dining, entertainment, top-rated schools, and major highways, this location offers unmatched convenience and an exceptional lifestyle. With fresh interior paint, gorgeous wood floors, new carpet, a first-floor primary suite, dedicated office, gas fireplace, and an incredible screened outdoor living space, this meticulously maintained home is truly move-in ready and offers everything today's buyers are looking for.

7773 Minutemen Loop, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 4b & 4c SubDv. ⋅ 34787 Zip Code

Virtually Staged. Experience the highly sought-after KENTON FLOOR PLAN in the award-winning WATERLEIGH community, just MINUTES FROM DISNEY! Ideally situated on a QUIET CUL-DE-SAC with NO THROUGH TRAFFIC, this beautifully upgraded 4 BEDROOM, 3 BATHROOM home offers WOOD-LOOK TILE throughout the main living areas and LUXURY VINYL PLANK upstairs. A welcoming foyer with TRAY CEILING opens to a versatile FLEX ROOM, perfect for a home office or formal dining room. The OPEN-CONCEPT design centers around a stunning GOURMET KITCHEN featuring 42" UPGRADED SHAKER CABINETS WITH CROWN MOLDING, QUARTZ COUNTERTOPS, UPGRADED TILE BACKSPLASH, 7' ISLAND, STAINLESS STEEL APPLIANCES, VENT HOOD, WALL OVEN & MICROWAVE COMBO, 5-BURNER COOKTOP, OVERSIZED SINGLE-BASIN SINK, WALK-IN PANTRY, plus a built-in COFFEE BAR/DROP ZONE. The spacious family room overlooks the covered lanai and backyard. A FIRST-FLOOR BEDROOM & FULL BATH provide the perfect guest or multigenerational suite. Upstairs, the PRIMARY SUITE features a TRAY CEILING, spa-inspired bath with GARDEN TUB, GLASS-ENCLOSED SHOWER, DUAL QUARTZ VANITIES, and an OVERSIZED WALK-IN CLOSET. A large LOFT offers the perfect space for a media room or playroom. Bedrooms 3 and 4 share a bath with DOUBLE SINKS, while the oversized laundry room includes a UTILITY SINK, WASHER & DRYER. Additional upgrades include BLOCK-ON-BLOCK CONSTRUCTION, WHOLE-HOUSE WATER FILTRATION, REVERSE OSMOSIS SYSTEM, UPGRADED LIGHTING & FANS, VIDEO DOORBELL, LOW-E DOUBLE-PANE WINDOWS, R-30 INSULATION, and RECLAIMED WATER IRRIGATION for outstanding energy efficiency. Enjoy MAINTENANCE-FREE LIVING with lawn care included and access to 4 RESORT-STYLE POOLS, 3 CLUBHOUSES, FITNESS CENTERS, TENNIS COURTS, FISHING PIER, PLAYGROUNDS, PARKS, WALKING TRAILS, and more. WATER SPRING ELEMENTARY and WATER SPRING MIDDLE SCHOOL are just a SHORT WALK AWAY, making everyday routines incredibly convenient. Zoned for HORIZON HIGH SCHOOL and ideally located near shopping, dining, Disney, and with easy access to 429, 417 & 408, this home offers the perfect blend of luxury, convenience, and lifestyle.

11031 Jackson Cove, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Carriage Pointe A-I & L SubDv. ⋅ 34787 Zip Code

Some homes are simply updated. This one has a personality all its own. Welcome to this one-of-a-kind 4-bedroom, 4-bath home in the gated community of Carriage Pointe, where artistic design, modern renovations, and exceptional indoor-outdoor living come together to create a truly unforgettable home. This oversized 0.34-acre corner lot sits on a quiet dead-end street with no neighbors to the left or rear. Mature privacy hedges surround the fenced backyard, creating a peaceful retreat, while two gated community entrances provide convenient access to shopping, dining, and major roadways. From the moment you arrive, the home impresses with its stacked stone façade, paver driveway, oversized 3-car garage, and professionally landscaped grounds featuring majestic oak trees, palms, agave, and decorative rock landscape beds. Inside, every detail has been thoughtfully designed. Updated flooring, beautifully renovated bathrooms, plantation shutters, and brand-new Reece impact-rated windows provide modern comfort, while artistic finishes add a distinctive character rarely found in residential homes. The welcoming foyer and formal living and dining spaces feature custom faux brick and textured wall finishes created by an artist who contributed to the Wizarding World attractions at Universal Orlando. The beautifully renovated kitchen is designed for everyday living and entertaining with dramatic black-and-white quartz countertops, a full-height matching backsplash, a stunning waterfall-edge island, abundant cabinetry, breakfast bar seating, and a sunny breakfast nook overlooking the spacious family room. The spacious primary suite offers a private retreat with a custom designer accent wall, dual walk-in closets, and a luxurious bath featuring dual vanities, a soaking tub, and a large frameless glass shower. Two secondary bedrooms share a convenient Jack-and-Jill bath, while the fourth bedroom and additional full bath provide flexibility for family, guests, or a home office. A standout feature is the private upstairs bonus room with its own full bath. Professionally soundproofed and currently used as a DJ studio, this versatile space can easily become a recording studio, podcast room, theater, gaming lounge, fitness space, office, or private guest suite. Enjoy Florida living year-round in the enclosed sunroom with insulated ceiling, creating a comfortable extension of the home's living space. Beyond awaits an incredible backyard retreat featuring a beautifully designed raised paver gathering space anchored by a grand wood-burning fireplace, creating the perfect outdoor setting for entertaining, relaxing, and enjoying evenings under the stars. Professional landscape lighting and mature privacy landscaping complete this special outdoor escape, with plenty of room to play, garden, or add a future pool. If you've been searching for a home that feels anything but ordinary, you've found it. With its creative design, thoughtful updates, versatile spaces, and unforgettable backyard, this is more than a home - it’s a place where memories are made.

15604 Granlund Street, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Orchard Hills Ph 3 SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully maintained 5-bedroom, 3.5-bath home with a spacious 3-car garage, offering the perfect blend of comfort, style, energy efficiency, and location. From the moment you step inside, you’ll appreciate the soaring ceilings, open living spaces, and thoughtful upgrades throughout. The custom stone fireplace, bring an inviting ambiance to those cozy evenings or when entertaining guests year round. At the heart of the home is the gourmet kitchen, featuring granite countertops, built-in appliances, abundant cabinetry, and plenty of space for cooking and entertaining. The adjoining living area is highlighted by a built-in fireplace, creating a warm and inviting focal point for family gatherings. One of the home’s standout features is the fully owned solar system, helping keep monthly electric costs exceptionally low—averaging approximately $33 per month. The exterior has been recently painted, adding fresh curb appeal. Step outside to the expansive backyard designed with possibilities in mind. The generous outdoor space offers ample room to add a pool whilst still leaving plenty of space for a dedicated grilling and outdoor dining area. Whether you're hosting summer barbecues, family gatherings or relaxing with friends, the spacious yard provides the ideal setting for creating your own private outdoor retreat. The modern floor plan offers five bedrooms and 3.5 bathrooms, providing flexibility for families, guests, or a home office, along with a generous 3-car garage for vehicles and additional storage. Ideally located in one of Winter Garden’s most desirable communities, this home is zoned for highly rated schools and offers convenient access to Walt Disney World, SR-429, downtown Orlando, and Orlando International Airport (MCO), making commuting, travel, shopping, dining, and entertainment easily accessible. If you’re looking for a move-in-ready home with premium features, exceptional energy savings, generous living space, and an outstanding location, this home is ready to welcome you.

5079 Palmetto Park Drive, Winter Garden

6 Beds ⋅ 5 Baths ⋅ Johns Lake Pointe SubDv. ⋅ 34787 Zip Code

Tucked inside sought-after Johns Lake Pointe, this impeccably maintained 6-bedroom, 5-bathroom, pool home offers 4,693 square feet of thoughtfully designed living space where style, comfort, and exceptional entertaining come together. With a versatile floor plan that includes a first-floor Primary suite, and additional Primary suite upstairs, expansive gathering spaces, and standout rooms for both relaxation and recreation, this home offers the flexibility and scale today’s buyers are searching for. Soaring ceilings and a bright, open layout create an inviting sense of space from the moment you enter, while the beautifully updated Kitchen serves as the heart of the home with quartz countertops, elegant white cabinetry, stainless double workstation sink, and Samsung Wi-Fi-enabled appliances. Luxury vinyl plank flooring runs throughout, adding warmth, durability, and a cohesive finish. Upstairs, the oversized Bonus/Game room with wet bar and beverage refrigerator offers the perfect place to unwind, while the dedicated Home Theater with projector, screen, surround sound, and reclining seating makes movie night an event of its own. And then there’s the backyard—an absolute showstopper! With tranquil pond and greenspace views, no rear neighbors, and a resort-style setting designed for year-round enjoyment, this outdoor space truly sets the home apart. The saltwater pool and spa feature a sun shelf, fire features, and electric heater, while the fully equipped Outdoor Kitchen with built-in grill, smoker, beverage refrigerator, and bar seating was made for effortless entertaining. Additional highlights include a 4-car garage with air conditioning, insulation, ceiling-mounted storage, and finished floors, along with a Mudroom, upstairs Laundry and updated lighting. Ideally located just minutes from Downtown Winter Garden, Winter Garden Village, the West Orange Trail, local schools, and major roadways, this is more than just a home—it’s a place to gather, celebrate, and enjoy the very best of Florida living.

427 Egret Place Drive, Winter Garden

Start Your Search