Winter Garden Homes with Colonial Architectural style

Winter Garden Homes with Colonial Architectural style

Welcome to Winter Garden, Florida – a charming city nestled in the heart of Orange County that beautifully blends small-town charm with modern conveniences. Just a stone's throw away from the bustling city of Orlando, Winter Garden boasts a vibrant downtown area filled with delightful shops, restaurants, and a rich tapestry of cultural events. The scenic West Orange Trail winds through the city, providing residents with ample opportunities for outdoor activities, from biking to leisurely strolls amidst picturesque views.

One of the standout features of Winter Garden is its stunning array of homes, particularly those showcasing the timeless elegance of Colonial architectural style. These homes, characterized by their symmetrical facades, grand columns, and intricate detailing, evoke a sense of nostalgia and grace. Many Colonial-style residences in Winter Garden are set on spacious lots, offering families the perfect blend of indoor comfort and outdoor space for gatherings and play.

The charm of Colonial homes is further complemented by Winter Garden’s lush landscapes and friendly community atmosphere. Residents enjoy a lifestyle steeped in history, with many of the homes reflecting the city's rich heritage. Whether you’re drawn to the historic architecture or the vibrant community events, Winter Garden is a place where you can truly feel at home.

If you’re looking for a place that offers both beauty and a warm sense of community, Winter Garden is waiting to welcome you home. Explore the captivating Colonial homes that grace this delightful city and discover your dream residence today!

Newest Winter Garden Homes with Colonial Architectural style

10048 Beach Port Drive, Winter Garden
$1,199,000
5 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2b SubDv. ⋅ 34787 Zip Code
LUXURY POOL HOME on PREMIUM LAKE FRONT LOT! Enjoy serene LAKE VIEWS and captivating SUNSETS! Most POPULAR Floor Plan – North Haven – has 5 Bedrooms, 3.5 Baths, Gourmet Kitchen, First Floor Primary Suite, TONS OF STORAGE, Tile Roof and 3 Car Garage just minutes from DISNEY! The OUTDOOR LIVING Space is a Showstopper! Generous COVERED Patio – perfect space for Dining and Relaxing! DELUXE SCREENED POOL with Sun Shelf, SALT SYSTEM, LED Lights and DECK JETS! This METICULOUSLY Maintained Home has a GOURMET KITCHEN with 42” Cabinets, Large Island, Upgraded Tile Backsplash, NEW PENDANT LIGHTS, Large FARM SINK, Under Cabinet Lighting, SS APPLIANCES including Built-In CONVECTION OVEN and COOK TOP with CABINETRY VENT HOOD! Large Pantry with CUSTOM SHELVING!! OPEN FLOOR PLAN with Views of the Patio, Pool and LAKE from Family Room and Casual Dining! First Floor Primary Suite with French Door to Patio and CUSTOM CLOSET! Bath Features DOUBLE Vanities and OVERSIZED Walk-In DOUBLE SHOWER. FLEX Space can be Dining Room, Office or Living Room. Convenient Remodeled Powder Bath with NEW Vanity, Counter and Mirror and Laundry Room with Cabinetry, Included WASHER and DRYER and Utility Sink complete the First Floor. Main Living Space has Upgraded Rectangular Tile, 8’ Doors and 5 ¼ Molding. Two Story Foyer features Stairs with Wood Railings and Wrought Iron Spindles. The HUGE LOFT separates the Upstairs. ALL 4 Bedrooms have WALK-IN Closets! Bedrooms 2 and 3 share Full Bath 2 with Upgraded SHOWER instead of a tub and Bedrooms 4 and 5 share a Jack-and-Jill Bathroom. Numerous Upgrades: GUTTERS, EV NEWER Dishwasher, NEW LED Pool Lights, NEW Solonoid for Pool Salt System, Dedicated GENERATOR Hook Up, Garage with EV Charger, EPOXY FLOOR and Overhead STORAGE RACKS ! ENERGY EFFICIENT Home with LoE Double Pane Windows, 15 Seer AC & Reclaimed Water for Irrigation Saves $$ on Utilities. Waterleigh is the PREMIER LIFESTYLE COMMUNITY with 4 Resort Style Pools, 3 Clubhouses with Fitness Centers, Walking Trails, Sand Volleyball, Dog Park, Fishing and Observation Pier, Tennis, Pickleball, Playgrounds and more! HOA Does all Yard Maintenance. All this zoned for NEW Atwater Bay Elementary, Water Spring Middle School and Horizon High School! Close to Disney, Shopping, Dining, 429, I-4, 417 and a NEW PUBLIX

10048 Beach Port Drive, Winter Garden
150 Hammock Preserve Loop, Oakland
$879,000
4 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Some homes simply sit in a neighborhood. This one feels like it belongs there. Welcome to 150 Hammock Preserve Loop, a 2023 Rockwell Homes residence tucked into the heart of Oakland Park, where the front porch looks out toward mature oak trees and the best parts of the Winter Garden lifestyle are never far from home. Step inside and you’re immediately greeted by a dedicated office to the left of the entry, creating the perfect work-from-home space while keeping it separate from the main living areas. Throughout the home, thoughtful custom updates give each space a personality of its own. The primary suite is conveniently located on the main floor, while the additional bedrooms and spacious loft are upstairs, creating a layout that offers both separation and flexibility. A rare three-car garage provides the extra space that can be difficult to find in Oakland Park, whether you need room for vehicles, golf carts, bikes, storage, or all of the above. Out back, the generous yard offers plenty of room to create your own outdoor retreat, including space for a future pool. But what makes this home especially difficult to replicate is everything beyond the front door. Oakland Park is one of Winter Garden’s most sought-after communities for a reason. Tree-lined streets, front porches, parks, playgrounds, two resort-style community pools, a clubhouse, dog park, waterfront spaces, and miles of trails create a neighborhood designed to actually be enjoyed. Hop on your bike and connect to the West Orange Trail, or grab the golf cart and head toward Downtown Winter Garden for a morning at the Farmers Market, drinks at Crooked Can, dinner along Plant Street, boutique shopping, community events, and everything surrounding Plant Street Market. Here, weekends can start with coffee on the front porch beneath the oaks, turn into an afternoon by the pool or on the trail, and end with a golf cart ride into Downtown Winter Garden. Built in 2023, filled with custom touches, complete with a dedicated office, rare three-car garage, and a backyard ready for what comes next, 150 Hammock Preserve Loop offers more than a beautiful home. It offers the Oakland Park lifestyle that makes this neighborhood so special.

150 Hammock Preserve Loop, Oakland
2102 Green Ash Court, Winter Garden
$749,000
5 Beds ⋅ 3 Baths ⋅ Wintermere Harbor SubDv. ⋅ 34787 Zip Code
Set in gated Wintermere Harbor, 2102 Green Ash Ct offers space to gather, room to spread out and a layout suited to multigenerational living. This 5-bedroom, 3-bath pool home has more than 3,700 square feet, soaring ceilings and two first-floor bedrooms, including the primary suite. Generous living areas make it easy to entertain or enjoy time at home, while the screened pool and private backyard invite you to make the most of Florida living. A public playground sits in the cul-de-sac next to the property, and a public pier offers a spot for picnics or fishing. With Disney,shopping and dining nearby and convenient access to SR-429, this Winter Garden home brings together a flexible floor plan, outdoor living and a location you’ll love.

2102 Green Ash Court, Winter Garden
11031 Jackson Cove, Winter Garden
$695,000
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 4b & 4c SubDv. ⋅ 34787 Zip Code
Virtually Staged. 2023 CONSTRUCTION • PRIVATE CUL-DE-SAC • FIRST-FLOOR BEDROOM & FULL BATH • FLEX ROOM • NO CARPET • SCHOOLS APPROXIMATELY 0.2 MILES AWAY • MINUTES FROM DISNEY Tucked away on a quiet cul-de-sac with no through traffic, this upgraded 4-bedroom, 3-bath Kenton home offers 2,931 square feet of thoughtfully designed living space in the resort-style Waterleigh community. A pond and conservation area at the end of the street add to the peaceful setting, with Water Spring Elementary and Middle School conveniently located nearby. Inside, the open-concept layout features a flexible first-floor room ideal for a home office, playroom, or potential fifth bedroom, plus a separate first-floor bedroom and full bath, perfect for guests or multigenerational living. The upgraded gourmet kitchen showcases quartz countertops, 42-inch shaker cabinetry, a 7-foot island, wall oven and microwave, five-burner cooktop, walk-in pantry, and built-in coffee bar. The spacious living area opens to a covered lanai and backyard for effortless indoor-outdoor living. Upstairs, you’ll find a generous primary suite, large loft, two additional bedrooms, and a conveniently located laundry room with a utility sink. Additional upgrades include whole-house water filtration, reverse osmosis, upgraded lighting and ceiling fans, and a video doorbell. Waterleigh residents enjoy resort-style pools, clubhouses, fitness centers, tennis courts, parks, and included lawn care, all just minutes from Walt Disney World and Central Florida’s best shopping, dining, and entertainment.

11031 Jackson Cove, Winter Garden
17434 Honeybell Tangelo Court, Winter Garden
$850,000
4 Beds ⋅ 4 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. NEARLY COMPLETE! Near Walt Disney World Theme Parks! Welcome to the Eliot plan, a luxurious new home offering a perfect blend of elegance, comfort, and functionality with 4 spacious bedrooms, 3.5 bathrooms, and an expansive loft and home office area. This home features a stunning exterior design and is designed to enhance both style and livability, showcasing a covered front porch and a covered backyard lanai - perfect for outdoor relaxation and entertaining. Step into the extended entryway, which leads to a versatile home office area, offering the perfect space for productivity or leisure. The heart of this home is the chef-inspired kitchen, complete with a large island and premium stainless-steel appliances, including an electric cooktop, built-in oven/microwave combo, dishwasher, and vent hood. The luxurious primary suite is located on the first floor for ultimate convenience and privacy. Upstairs boasts an extended loft that provides an excellent space for lounging as well as three secondary bedrooms - one with its own ensuite! Additional features include an 8-foot front door and 8' doors on the 1st floor, upgraded flooring throughout, ample storage closets, and a new home warranty for peace of mind. Call today to schedule a tour!

17434 Honeybell Tangelo Court, Winter Garden
279 Zachary Wade Street, Winter Garden
$1,675,000
5 Beds ⋅ 4 Baths ⋅ Lakeview Reserve SubDv. ⋅ 34787 Zip Code
An unparalleled lakefront opportunity in Downtown Winter Garden **Seize the rare chance to own a premier waterfront estate where the true value lies in the spectacular lot, private dock, and an enviable golf-cart lifestyle ** Launch your boat from your private lift for a scenic 30-minute cruise to Mt. Dora or take your golf cart just minutes away to the historic downtown Farmers’ Market and restaurants **Positioned within a private, gated enclave directly across from the West Orange Trail, this property offers the ultimate Florida resort lifestyle outside, featuring a heated saltwater pool, raised spa, and a fully fenced, expansive lakeside yard ** Inside, the home boasts a massive primary suite +/16x26’ with tray ceiling, fireplace and a balcony with lovely lake views and massive +/-23x25 bonus room including a wet bar and fireplace** The kitchen has a large cooking island w/sink plus a separate breakfast bar, stone counters, under cabinet lighting, a Jenn-Air double convection oven and lovely dining area overlooking the lake ** There's even an open wine closet/alcove with wine refrigerator off the kitchen ** First floor bedroom with an oversized walk in closet as a 5th bedroom or den (currently being used as a dining room) ** Other home upgrades include a newer roof +/-2022, 3 newer A/C units, a whole-home Katolight 40KW generator that runs +/- 90% of the home, crown molding throughout the home, ADT security system with cameras, boat house with new roof 2025, resurfaced pool +/-5 yrs ago & Aqualink pool/spa automation system and a 10’ seawall ** Relax on the covered screened patio with the Bose speaker system and prime outdoor living space including additional yard space beyond the pool and patio ** 2 car garage plus a 1 car garage with easy access to the back yard perfect for bringing your boat or lawn equipment through ** LOW HOA fees $200 quarterly ** All room measurements in MLS and on 3d floorplan are approximate. Buyer to verify. Tax record is incorrect - property has 5 bedrooms. Dock measurement is estimated. Buyer to verify. Solar panel lease to be transferred to buyer at closing.

279 Zachary Wade Street, Winter Garden
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