Winter Garden Homes with Traditional Architectural style

Winter Garden Homes with Traditional Architectural style

Welcome to Winter Garden, Florida—a charming city that perfectly blends small-town warmth with modern amenities, making it one of Central Florida’s most desirable locations. Nestled just a stone’s throw from the bustling city of Orlando, Winter Garden boasts a rich history, vibrant community spirit, and an array of outdoor activities that cater to residents of all ages.

One of the most appealing features of Winter Garden is its diverse architectural landscape, particularly the stunning homes that showcase traditional architectural styles. These homes exude timeless elegance, with classic features such as gabled roofs, intricate woodwork, and inviting front porches that beckon you to relax and enjoy the serene surroundings. The traditional architecture in Winter Garden creates a sense of nostalgia, reminiscent of simpler times, while seamlessly integrating modern comforts and conveniences.

The city's historic downtown area is a treasure trove of boutiques, cafes, and artisanal shops, all set against a backdrop of beautifully preserved buildings that reflect the city’s rich heritage. Residents can enjoy leisurely strolls along the West Orange Trail, which winds through picturesque parks and scenic landscapes, providing ample opportunities for biking, jogging, and family outings.

Winter Garden is not just a place to live; it’s a community that offers a high quality of life with excellent schools, friendly neighbors, and a calendar full of events that bring everyone together. If you’re looking for a home that combines traditional charm with a vibrant lifestyle, Winter Garden is the perfect place to call home. Discover the warmth and beauty of this enchanting city today!

Newest Winter Garden Homes with Traditional Architectural style

2010 Boss Hewett Street, Oakland
$1,450,000
5 Beds ⋅ 4 Baths ⋅ Hull Island/Oakland Ph 2 SubDv. ⋅ 34787 Zip Code
Beautiful 2022-built home in Hull Island featuring 5 bedrooms, 4 full bathrooms, approximately 3,781 heated square feet, a private pool, and a two-car garage. Open-concept living with a gourmet kitchen, quartz countertops, a spacious loft, and two primary suites, including one on the first floor. Community amenities include a pool, trails, playground, dog park, and private dock. Buyer to verify all measurements, HOA terms, and property details.

2010 Boss Hewett Street, Oakland
5705 New Independence Parkway, Winter Garden
$399,900
3 Beds ⋅ 2 Baths ⋅ Signature Lakes - Phase 2 SubDv. ⋅ 34787 Zip Code
WELCOME HOME TO 5705 NEW INDEPENDENCE PARKWAY! Discover the perfect blend of COMFORT, CHARM, and RESORT-STYLE LIVING in the highly desirable INDEPENDENCE / SIGNATURE LAKES COMMUNITY of WINTER GARDEN, FLORIDA! This inviting 3-BEDROOM, 2.5-BATH TOWNHOME offers 1,751 SQ. FT. OF LIVING SPACE, a PRIVATE REAR-ENTRY 2-CAR GARAGE, and a wonderful opportunity to enjoy everything that makes Central Florida living so special. From the moment you arrive, the CHARMING FRONT PORCH welcomes you home. Step inside to discover a bright, OPEN-CONCEPT FLOOR PLAN filled with NATURAL LIGHT, creating a comfortable setting for everyday living, entertaining friends, or simply unwinding after a long day. The SPACIOUS KITCHEN features GRANITE COUNTERTOPS, generous cabinet storage, and plenty of room to gather, while UPDATED LAMINATE FLOORING adds warmth throughout the main living areas. A NEWER HVAC SYSTEM INSTALLED IN 2025 provides an added touch of comfort and peace of mind. Upstairs, the PRIMARY SUITE offers a relaxing retreat with a PRIVATE ENSUITE BATHROOM and WALK-IN CLOSET. Two additional bedrooms provide flexible space for guests, hobbies, or a HOME OFFICE. Whether you're enjoying your morning coffee on the FRONT PORCH, hosting dinner with loved ones, or relaxing on the PRIVATE PATIO, this home offers room to create lasting memories. Life in INDEPENDENCE is about so much more than the home itself! Residents enjoy an exceptional collection of RESORT-STYLE AMENITIES, including TWO COMMUNITY POOLS, FITNESS CENTERS, a CLUBHOUSE, PARKS, PLAYGROUNDS, DOG PARKS, TENNIS AND BASKETBALL COURTS, SCENIC WALKING TRAILS, and COMMUNITY LAKE ACCESS. Neighborhood gatherings and community events create opportunities to connect, unwind, and truly feel at home. And the LOCATION is equally impressive! Nestled in the heart of HORIZON WEST, you're conveniently located near HAMLIN TOWN CENTER, HISTORIC DOWNTOWN WINTER GARDEN, the WEST ORANGE TRAIL, and WALT DISNEY WORLD, with easy access to shopping, dining, entertainment, major roadways, and area schools. LOCATION, COMFORT, COMMUNITY, AND RESORT-STYLE LIVING — ALL IN ONE PLACE! With 3 BEDROOMS, 2.5 BATHROOMS, 1,751 SQ. FT., A PRIVATE 2-CAR GARAGE, and an incredible array of NEIGHBORHOOD AMENITIES, 5705 NEW INDEPENDENCE PARKWAY is more than just a place to live — it's a place to feel at HOME. WELCOME HOME TO INDEPENDENCE, WINTER GARDEN!

5705 New Independence Parkway, Winter Garden
5513 New Independence Parkway, Winter Garden
$575,000
3 Beds ⋅ 2 Baths ⋅ Independence / Signature Lakes Ph 02 SubDv. ⋅ 34787 Zip Code
Nestled in the heart of the desirable Winter Garden, this beautifully updated 3-bedroom, 2-bathroom SALTWATER POOL HOME offers 1,920 square feet of thoughtfully designed living space, modern elegance, and an exceptional resort-style lifestyle! From the moment you arrive, you’ll fall in love with the picturesque curb appeal, lush landscaping, charming brick-paver walkway, and inviting covered front porch. Step inside to discover a bright, open-concept floor plan featuring beautiful bamboo flooring, abundant natural light, and inviting living spaces perfect for everyday comfort and entertaining. The heart of the home is the stunning kitchen, completely remodeled in 2019! Featuring gorgeous quartz countertops, rich cabinetry, stainless steel appliances, stylish pendant lighting, and an expansive island with seating, this space is designed for gathering and making memories. A charming, sun-filled dining nook completes the picture! Your own private backyard oasis awaits! Step through beautiful French doors to your sparkling SALTWATER POOL, surrounded by an expansive screened enclosure and spacious covered lanai. Whether you're enjoying a refreshing afternoon swim, hosting weekend gatherings, or relaxing in the shade, this outdoor retreat makes every day feel like a vacation! Additional highlights include a convenient rear-entry garage with a beautifully finished epoxy floor. The lifestyle doesn't stop at your front door! Enjoy RESORT-STYLE COMMUNITY AMENITIES and a vibrant calendar of year-round events, including themed movie nights, ice cream socials, fireworks, and seasonal celebrations. Even better, the HOA includes internet and cable. Ideally located in the beautiful Winter Garden, walkable to schools, shopping, dining, entertainment, and conveniently located to Central Florida attractions, this home offers the perfect blend of modern comfort, neighborhood charm, and Florida living. More than a home....it's a lifestyle! Schedule your private showing today! *Wine fridge and weather station on the lanai screen does not convey.

5513 New Independence Parkway, Winter Garden
11390 Bourbon Rose Circle, Winter Garden
$860,494
4 Beds ⋅ 3 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code
What's Special: No Rear Neighbors | Larger Lot | Convenient 1st Floor Living. New Construction - Ready Now! Welcome to the Bainbridge at 11390 Bourbon Rose Circle in Esplanade at McKinnon Groves! This spacious single-story home offers four bedrooms, three bathrooms, a versatile flex room, and a three-car garage. The open-concept layout features a bright great room that flows into the dining area and gourmet kitchen with walk-in pantry, creating the perfect space for gathering and entertaining. The private primary suite is tucked away at the rear of the home, while three secondary bedrooms provide comfort and flexibility. Enjoy outdoor living on the covered lanai. Additional Highlights Include: tray ceiling package, whole house 8' interior doors, outdoor kitchen rough-in, and prewired for future pool and spa. MLS#O6451559 Esplanade at McKinnon Groves offers resort-style living in a gated Winter Garden community surrounded by natural beauty. Planned amenities include a fitness center, movement studio, resort pool and spa, Bahama Bar, pickleball, tennis, and bocce courts. Residents will also enjoy yoga lawns, a Bark Park, rose garden, scenic trails, concierge services, and year-round events. Zoned for Lake County schools, it blends everyday convenience with an active lifestyle.

11390 Bourbon Rose Circle, Winter Garden
16742 Oakboro Street, Winter Garden
$519,000
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Welcome to this better-than-new 4-bedroom, 2.5-bathroom home in the highly desirable Waterleigh community of Horizon West! Built in 2020, this thoughtfully upgraded home offers 2,014 square feet of living space, an inviting open-concept layout ideal for entertaining, and the convenience of a first-floor primary suite featuring a custom closet. The kitchen boasts granite countertops, stainless steel appliances, a touch-activated pull-down faucet, and a spacious butler’s pantry offering abundant storage. Additional owner upgrades include matte black hardware and ceiling fans throughout, smart light switches and fans, and a Fisher & Paykel washer and dryer. Enjoy Florida living year-round on the screened-in lanai, with added peace of mind from the upgraded fenced yard featuring two gates and puppy pickets, a complete gutter system, and electrical wiring ready for a whole-house generator. The garage is equipped with overhead storage and is EV-ready with an installed Tesla charger. Waterleigh residents enjoy an exceptional array of amenities, including two resort-style clubhouses and pools, two fitness centers, putt-putt golf, beach volleyball, tennis, a lake-view picnic area, a dog park, and more. With its desirable location, modern conveniences, and extensive upgrades, this home offers a wonderful opportunity to enjoy the best of the Waterleigh lifestyle!

16742 Oakboro Street, Winter Garden
17600 Lake Star Road, Winter Garden
$1,350,000
5 Beds ⋅ 4 Baths ⋅ Northlake/Ovation Ph 1 SubDv. ⋅ 34787 Zip Code
Discover exceptional lakefront living in Northlake at Ovation, where this extensively upgraded Ashton Woods residence showcases more than $320,000 in builder design selections and owner-added enhancements. Thoughtfully curated interiors, distinctive architectural details, and inviting outdoor spaces create a home equally suited to elegant entertaining and everyday comfort. A soaring foyer, statement chandelier, and beautifully detailed staircase establish an impressive arrival. Natural light fills the living spaces, highlighting plantation shutters, upgraded tile and hardwood flooring, custom wall treatments, and designer lighting throughout. The separate dining room provides an elegant setting for gatherings, while the kitchen, breakfast area, and family room flow seamlessly together. At the heart of the home, the beautifully appointed kitchen pairs an expansive contrasting island with designer quartz countertops, stacked cabinetry, and illuminated display accents. A custom backsplash and mural extending to the ceiling create a striking focal point, complemented by stainless steel appliances, pendant lighting, and a custom-organized pantry. The primary suite creates a peaceful retreat with hardwood flooring, generous windows, and a custom walk-in closet. Its spa-inspired bathroom features a soaking tub, separate vanities, upgraded fixtures, and an expansive frameless glass shower framed by striking tilework. Additional bedrooms and bathrooms carry the home’s thoughtful design throughout, including custom closet systems in the downstairs bedroom and designer accent walls in the downstairs bathroom. A dedicated office and spacious upstairs loft provide versatile settings for work, leisure, and recreation. Outdoor living unfolds beneath a covered paver lanai with roll-up screens and a custom summer kitchen featuring a built-in grill, beverage chiller, sink, upgraded countertops, and integrated storage. Generous dining and lounging areas overlook the fenced backyard, mature greenery, and tranquil lakefront setting—an inviting backdrop for morning coffee or evening gatherings. Beyond its beautiful finishes, the home incorporates carefully considered functionality: a custom laundry room with cabinetry and a sink, a drop zone, custom storage, whole-house gutters, backyard French drains, and pre-plumbing for a water softener. A hardwired security system and cameras, along with hardwired internet and Ethernet connections at TVs, provide added convenience. The garage includes epoxy flooring, overhead smart storage racks, cabinetry, and a utility sink. Redesigned landscaping and architectural uplighting enhance the home’s presence after sunset. Northlake at Ovation amenities include a community pool, clubhouse, playground, and dog park. Nearby Hamlin Town Center and Winter Garden Village provide shopping, dining, and entertainment, while Historic Downtown Winter Garden invites exploration of its boutiques, restaurants, celebrated farmers market, and West Orange Trail. Walt Disney World and Central Florida’s renowned attractions are within reach, with SR 429 connecting you to the greater Orlando area. Experience beautifully appointed interiors, extensive upgrades, and inviting lakefront living in this exceptional Winter Garden residence. Schedule your private showing.

17600 Lake Star Road, Winter Garden
1210 Brandy Lake View Circle, Winter Garden
$450,000
3 Beds ⋅ 2 Baths ⋅ Brandy Creek SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this charming 3-bedroom, 2-bath home nestled in the desirable gated community of Brandy Creek in Winter Garden! Step inside to discover an inviting, open layout where the living area flows seamlessly into the kitchen and dining space, creating a comfortable setting for everyday living and entertaining. The kitchen features granite countertops and ample cabinetry for storage. French doors open to an extended screened-in lanai, providing the perfect space to relax, entertain, or simply enjoy the Florida lifestyle. The fenced backyard offers additional room for outdoor activities, pets, or gatherings with family and friends. The primary suite features a walk-in closet and an en-suite bathroom with dual sinks, a garden tub, and a separate shower. The additional bedrooms provide comfortable, flexible spaces for family, guests, or a home office. With generous living spaces and the opportunity to add your own personal touches, this home offers wonderful potential to make it truly your own. Beyond the home, Brandy Creek offers a peaceful setting with tranquil ponds, a scenic lake, and a community fishing pier. Just minutes from Historic Downtown Winter Garden, you'll enjoy easy access to the popular West Orange Trail, Saturday Farmers Market, live music, boutique shopping, and an incredible variety of local restaurants. Convenient access to the Florida Turnpike and SR-429 makes commuting and exploring Central Florida a breeze. Whether you're enjoying a quiet evening on your screened lanai or exploring the charm of downtown Winter Garden, this home offers a wonderful combination of space, location, and lifestyle. Don't miss the opportunity to make it your own!

1210 Brandy Lake View Circle, Winter Garden
15749 Cutter Sail Place, Winter Garden
$789,900
4 Beds ⋅ 3 Baths ⋅ Lakeshore Preserve Ph 5 SubDv. ⋅ 34787 Zip Code
Welcome to an exceptional opportunity to experience refined Florida living in the highly desirable Lakeshore Preserve community by Toll Brothers. From its impressive architectural presence and elegant columned entrance to its beautifully designed interior, this remarkable residence combines timeless elegance, modern design, and everyday comfort. Step inside and discover an inviting atmosphere highlighted by soaring ceilings, abundant natural light, beautiful architectural details, and thoughtfully selected finishes. The spacious, open-concept floor plan creates a seamless connection between the main living and entertaining areas, creating an ideal setting for intimate gatherings and grand celebrations alike. Elegant crown molding, plantation shutters, designer lighting, and beautiful flooring contribute to the home's luxurious appeal. At the heart of the residence, the beautifully appointed gourmet kitchen is designed to impress, featuring an expansive center island, upgraded cabinetry, generous counter space, stainless steel appliances, a gas cooktop, and double wall ovens. Perfectly positioned alongside the dining and living areas, this welcoming space brings together style, functionality, and effortless entertaining. A striking custom entertainment feature adds architectural character and creates an impressive focal point within the main living area. The spacious primary suite provides a private retreat designed for relaxation, complemented by a beautifully appointed bathroom featuring elegant finishes and a generous walk-in shower. Additional bedrooms provide comfortable accommodations, while a dedicated office with a closet creates versatility for a home workspace, study, or additional flex space. A flexible office/den can also function as a 4th bedroom. Thoughtful details throughout the residence enhance both comfort and functionality, including upgraded finishes, attractive lighting fixtures, and convenient storage solutions. The home's appeal extends outdoors, where a covered living area provides a wonderful setting for enjoying Florida's beautiful weather, whether relaxing with your morning coffee or entertaining guests. Additional highlights include a well-appointed laundry area and an upgraded garage featuring epoxy-style flooring and overhead storage. Additional upgrades include a tankless natural gas water heater. Beyond the residence, discover the exceptional lifestyle of Lakeshore Preserve. This beautifully designed community features a spectacular resort-style swimming pool surrounded by tropical landscaping, inviting lounge areas, and picturesque lake views. Residents can also enjoy a fully equipped fitness center, covered outdoor grilling and dining areas, and a community playground. Ideally located near Hamlin Town Center, Winter Garden Village, Historic Downtown Winter Garden, the West Orange Trail, Walt Disney World Resort, and SR 429, with convenient access to shopping, dining, entertainment, and Orlando. Horizon West continues to grow with new retail, restaurants, and recreational improvements. Experience the perfect balance of luxury, elegance, and Florida living. Schedule your private showing today and experience the beauty, elegance, and exceptional lifestyle of this remarkable residence!

15749 Cutter Sail Place, Winter Garden
1300 Eastern Pecan Place Unit 208, Winter Garden
$298,500
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
BUYER INCENTIVE! Seller offering $5,000 toward buyer closing costs PLUS an additional $1,000 through the preferred lender—for up to $6,000 in buyer benefits with accepted contract, at closing Plus, enjoy a 2-year warranty on NEW kitchen appliances(refrigerator,microwave and dishwasher). Priced under $299,000! Discover this beautifully updated, move-in-ready condo in the GATED Southern Pines community, just 7 minutes from Historic Downtown Winter Garden! This second-floor residence offers convenient first-floor entry with private keyless access and a welcoming coat closet. Upstairs, the bright, open-concept feature newer luxury plank vinyl flooring, abundant natural light, updated lighting and ceiling fans, and a dedicated office alcove with custom built-in shelving. Fresh paint throughout—including walls, ceilings, doors, baseboards, and trim—creates a clean, contemporary feel. The upgraded galley kitchen features neutral cabinetry, granite countertops, a pantry, and BRAND-NEW, NEVER-USED stainless-steel refrigerator, microwave, and dishwasher! Its efficient layout keeps cooking connected to the living areas, while the conveniently located laundry room makes everyday tasks easier. The desirable split-bedroom floor plan continues with luxury plank vinyl flooring and offers privacy for the spacious primary suite, complete with a walk-in closet, ceiling fan and en-suite bath featuring a large walk-in shower and granite-topped vanity. Two additional bedrooms on the opposite side of the common area both with generous walk-in closets and ceiling fans. The second full bath features an extended granite vanity with abundant storage and a tub/shower combination. Both bathrooms showcase BRAND-NEW MOEN faucets and shower/tub fixtures, updated lighting, framed/finished mirrors, and new cabinet hardware. All interior door hardware has also been replaced with lever handles and hinges in updated finish to match all the new fixtures and hardware throughout. Extra storage is a plus in the laundry-room (Washer and dryer are negotiable) and linen closet near the HVAC system, which has received seasonal servicing. Drapes do not convey. Resort-style amenities abound! Southern Pines residents enjoy a pool and spa, fitness center, tennis courts, indoor basketball court, volleyball court, playground, pet park, clubhouse with theater room, billiards room, computer center, BBQ area, and resident car wash station. Gated entry and on-site management add convenience. Enjoy easy access to Publix, Winter Garden Village, the West Orange Trail, Historic Downtown Winter Garden, shopping, dining, entertainment and medical facilities. The Florida Turnpike, SR 429, and I-4 provide convenient connections throughout Central Florida, including Orlando attractions and major employment centers. HOA dues include internet, basic cable, trash service, recreational amenities, and exterior lawn care and exterior maintenance. Enjoy the convenience of condo living, with exterior maintenance and roof replacement handled through the association in accordance with its governing documents and budget. EXTENSIVELY UPDATED. MOVE-IN READY. EXCEPTIONAL VALUE! Brand-new kitchen appliances, a 2-year appliance warranty, resort-style amenities managed professionally and up to $6,000 in buyer benefits make this a fantastic Winter Garden opportunity. Schedule your private showing today!

1300 Eastern Pecan Place Unit 208, Winter Garden
14825 Porter Road, Winter Garden
$609,998
3 Beds ⋅ 3 Baths ⋅ Summerlake Pd Phase 2a And 2b SubDv. ⋅ 34787 Zip Code
Virtually Staged. With 2,732 square feet, a spacious upstairs loft and a downstairs room ready to serve as a fourth bedroom, this Summerlake home gives you room to arrange life as you please. Three bedrooms and 2.5 baths. The open main floor has tile underfoot, plantation shutters and a stone accent wall in the living room. The kitchen offers a granite island with seating, dark wood cabinetry, tile backsplash, gas range and pendant lighting, and opens to the dining area. Sliders lead to a covered paver patio and a fenced backyard with a fire pit. Upstairs, the primary suite has a custom-fitted walk-in closet, double vanity, soaking tub and glass-enclosed shower. Stone-trimmed covered front porch, & a rear-entry garage. Summerlake amenities include a resort-style pool with splash pad, lakefront clubhouse, fitness center, tennis and basketball courts, playgrounds, dog park, fishing pier and walking trails. This home is conveniently located close to the amenities. Close to Hamlin Town Center, SR 429 and a short drive to the Parks.

14825 Porter Road, Winter Garden
17332 Wild Daisy Drive, Winter Garden
$814,359
4 Beds ⋅ 3 Baths ⋅ Hamlin Meadows At Hamlin SubDv. ⋅ 34787 Zip Code
Virtually Staged. Under Construction. The BISCAYNE floorplan offers a spacious two-story design that perfectly balances functionality and flexibility, ideal for growing families. With three bedrooms and two and a half bathrooms, this layout provides ample space for everyday living and special moments alike. On the first floor, you'll find a flex room that can serve as a home office, gym, or an optional guest bedroom, depending on your needs. The open-concept design flows seamlessly from the dining room into the expansive great room, making it perfect for entertaining. A covered patio extends your living space outdoors, ideal for relaxing or hosting gatherings. The second floor offers all four bedrooms, including an extended primary suite with a walk-in closet and private bath, ensuring a peaceful retreat. An extended bonus room on this level provides additional versatility, perfect for a playroom or media space. Laundry is conveniently located upstairs to make daily chores easier. This floorplan is designed to accommodate diverse lifestyles, giving you the perfect combination of open spaces and private retreats. With options to add an additional bedroom.

17332 Wild Daisy Drive, Winter Garden
17326 Wild Daisy Drive, Winter Garden
$722,222
4 Beds ⋅ 3 Baths ⋅ Hamlin Meadows At Hamlin SubDv. ⋅ 34787 Zip Code
Virtually Staged. Under Construction. The Anna Maria floor plan is a beautifully designed one-story home offering four bedrooms and three bathrooms, thoughtfully arranged for comfortable everyday living. The open-concept layout features a spacious great room that flows effortlessly into the kitchen and dining area, creating an inviting space for entertaining or relaxing at home. The private primary suite includes a well-appointed ensuite bath and a generous walk-in closet. A covered patio extends the living space outdoors, while the two-car garage adds convenience and functionality. With 2,235 square feet of well-designed living space, the Anna Maria delivers both style and practicality in a layout that truly works for today’s lifestyle.

17326 Wild Daisy Drive, Winter Garden
Start Your Search

How much is your home worth?

Get instant property value now!