Winter Garden/Oakland Homes with Colonial Architectural style

Winter Garden/Oakland Homes with Colonial Architectural style

Welcome to Winter Garden and Oakland, two charming communities nestled in the heart of Orange County, Florida. Known for their picturesque landscapes and vibrant local culture, these areas offer a delightful blend of history, modern amenities, and a welcoming atmosphere.

Winter Garden, with its historic downtown, is a hub for local shops, farmers' markets, and delightful eateries. The scenic West Orange Trail winds through the area, perfect for biking, walking, or simply enjoying the beautiful Florida weather. Just a stone's throw away, the quaint town of Oakland boasts a serene setting with lush greenery and stunning lake views, making it a perfect escape from the hustle and bustle of city life.

One of the standout features of homes in this region is their captivating Colonial architectural style. These homes exude timeless elegance with their symmetrical facades, grand columns, and classic brickwork. The Colonial style is known for its spacious interiors and traditional layouts, making them ideal for families and those who appreciate a touch of history in their living spaces. Many of these homes are surrounded by lush gardens and mature oak trees, enhancing the charm of the neighborhood.

Whether you're looking for a cozy family home or a spacious estate, Winter Garden and Oakland offer a variety of options that cater to different tastes and lifestyles. Embrace the warm community spirit and rich history of these areas, where every street tells a story, and every home is a gateway to a vibrant life in sunny Florida. Come explore your dream home in this enchanting corner of the Sunshine State!

Newest Winter Garden/Oakland Homes with Colonial Architectural style

$775,000
5 Beds ⋅ 4 Baths ⋅ Lakeview Pointe At Horizon West SubDv. ⋅ 34787 Zip Code
WELCOME TO LAKEVIEW POINTE AT HORIZON WEST! This 5-bedroom, 4-full-bath Pulte Creekview floorplan offers a flexible two-story layout with a downstairs primary suite, upstairs loft, flex room, 3-car garage, and a fully fenced corner-lot backyard. Hardwood flooring extends throughout the first floor, complemented by tray ceilings in the foyer and primary suite, plantation shutters, neutral interior paint, and updated lighting in the flex space and breakfast nook. The open kitchen, café, and family room create a central gathering space, featuring 42-inch maple cabinetry with crown molding and hardware, granite countertops, an oversized island with breakfast bar seating, built-in wall oven and microwave, corner walk-in pantry, and extended cabinetry along the breakfast nook for additional storage. Glass sliders with a remote-controlled window treatment open to the covered, extended screened brick-paver patio overlooking the private fenced yard. The downstairs primary suite includes a tray ceiling, oversized walk-in closet, dual-sink granite vanity, glass-enclosed tiled walk-in shower, and private water closet. Three additional bedrooms are located downstairs, including one adjacent to a full bath with dual-sink granite vanity, while two bedrooms share another full bath. Upstairs, a loft, storage room, fifth bedroom with extensive closet space, and a fourth full bath provide versatile space for guests, work, hobbies, or media use. Recent improvements include interior and exterior paint, two new AC systems installed in 2025, ceiling fans, bathroom mirrors, front door hardware, epoxy-finished garage floor, and overhead garage storage racks. Kitchen appliances, washer, and dryer convey. A transferable Choice Home Warranty is included through May 2027, subject to warranty terms. Lakeview Pointe HOA includes lawn care, irrigation, community pool, fitness center, playground, and additional community amenities. Convenient Horizon West location near Hamlin shopping and dining, SR-429, Winter Garden Village, Walt Disney World Resort, and major Central Florida attractions.

7052 Enchanted Lake Drive, Winter Garden
$599,000
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
$715,000
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!** Tucked away on a **PRIVATE, QUIET CUL-DE-SAC WITH NO THROUGH TRAFFIC**, this beautifully upgraded 4-BEDROOM, 3-BATHROOM home offers an exceptional layout with a **FIRST-FLOOR BEDROOM & FULL BATH**, a **FLEX ROOM WITH POTENTIAL FOR A 5TH BEDROOM OR HOME OFFICE**, and **LUXURY VINYL PLANK FLOORING UPSTAIRS WITH NO CARPET THROUGHOUT THE HOME**. Step inside to a welcoming foyer with a TRAY CEILING that opens to the versatile FLEX ROOM. The heart of the home is the **UPGRADED GOURMET KITCHEN**, featuring 42" UPGRADED SHAKER CABINETS WITH CROWN MOLDING, QUARTZ COUNTERTOPS, UPGRADED TILE BACKSPLASH, 7-FOOT ISLAND, STAINLESS STEEL APPLIANCES, VENT HOOD, WALL OVEN & MICROWAVE COMBO, 5-BURNER COOKTOP, OVERSIZED SINGLE-BASIN SINK, WALK-IN PANTRY, and a BUILT-IN COFFEE BAR/DROP ZONE. WOOD-LOOK TILE flows throughout the main living areas, creating a seamless and elegant design. The OPEN-CONCEPT FAMILY ROOM overlooks the COVERED LANAI and backyard, while the **FIRST-FLOOR BEDROOM & FULL BATH** provide an ideal GUEST SUITE or MULTIGENERATIONAL LIVING SPACE. Upstairs, the spacious PRIMARY SUITE features a TRAY CEILING, OVERSIZED WALK-IN CLOSET, and a SPA-INSPIRED BATH with DUAL QUARTZ VANITIES, GARDEN TUB, and GLASS-ENCLOSED SHOWER. A generous LOFT offers additional living space, while BEDROOMS THREE AND FOUR share a bathroom with DUAL SINKS. The OVERSIZED LAUNDRY ROOM includes a UTILITY SINK, WASHER, and DRYER. Additional upgrades include BLOCK-ON-BLOCK CONSTRUCTION, WHOLE-HOUSE WATER FILTRATION, REVERSE OSMOSIS SYSTEM, UPGRADED LIGHTING & CEILING 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 RESORT-STYLE AMENITIES featuring FOUR POOLS, THREE CLUBHOUSES, FITNESS CENTERS, TENNIS COURTS, PLAYGROUNDS, PARKS, WALKING TRAILS, and a FISHING PIER. **WALKABLE TO WATER SPRING ELEMENTARY AND WATER SPRING MIDDLE SCHOOL**, making school drop-offs incredibly convenient. Zoned for HORIZON HIGH SCHOOL and located just MINUTES FROM DISNEY, SHOPPING, DINING, and major highways including 429, 417, and 408, this home combines LUXURY, CONVENIENCE, and an UNBEATABLE LIFESTYLE.

11031 Jackson Cove, Winter Garden
$844,000
4 Beds ⋅ 4 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. 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
$2,199,000
4 Beds ⋅ 5 Baths ⋅ Oakland Park Un # 2a SubDv. ⋅ 34787 Zip Code
Experience elevated living in this exceptional custom home by J&J Building, perfectly positioned in one of Winter Garden’s most desirable locations directly across from the iconic West Orange Trail. Offering over 5,000 square feet of thoughtfully designed luxury, 811 Civitas Way blends sophisticated style, flexible living spaces, and impressive functionality rarely found in today’s market. Designed for both everyday comfort and unforgettable entertaining, the home features a truly jaw-dropping media room that delivers the ultimate cinematic experience. Multiple office and flex space options provide incredible versatility for remote work, creative pursuits, fitness, or multigenerational living. With bedrooms thoughtfully positioned on both the first and second floors, the layout offers ideal privacy and convenience for guests and family alike. Luxury details and custom upgrades are showcased throughout, including a whole-home generator, a one-year-old Sub-Zero refrigerator, two stunning crystal chandeliers installed last year, and elegant solid brass door hardware throughout the home. You'll fall in love with the large island in the garage that even includes a built-in gift wrapping station! Every space reflects exceptional craftsmanship and thoughtful design, with countless additional custom touches that elevate the home’s overall sophistication and character. One of the property’s standout features is its exceptionally rare amount of parking for 7 cars plus a golf cart— a coveted luxury that sets this home apart. Combined with its prime location near Downtown Winter Garden, scenic trail access, dining, shopping, and commuter routes, this residence offers a lifestyle that is as refined as it is practical. **There is room to add a pool and ADU on this lot, as well! Artist renderings with the pool included in the photos.

811 Civitas Way, 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
Start Your Search