Oakland Park Homes with Pool Community Features

Oakland Park Homes with Pool Community Features

Welcome to Oakland Park, a vibrant and inviting subdivision nestled in the heart of Winter Garden, Florida. This charming community is located in Orange County, where the sun shines brightly and the spirit of Florida living thrives. Oakland Park is designed for those who seek a blend of modern convenience and a laid-back lifestyle, making it the perfect place to call home.

One of the standout features of Oakland Park is its stunning homes, many of which come complete with private pools. Imagine stepping out into your backyard oasis, where you can relax in the sun, host summer barbecues, or enjoy a refreshing dip on a warm Florida day. These homes are designed with comfort and style in mind, featuring spacious layouts and contemporary finishes that cater to both families and individuals alike.

The community itself is a treasure trove of amenities that enhance your living experience. Residents enjoy beautifully landscaped common areas, walking trails, and parks, perfect for leisurely strolls or family outings. The sense of community is palpable, with friendly neighbors and organized events that foster connections and create lasting friendships.

Located just a stone's throw away from Winter Garden's bustling downtown, residents of Oakland Park have easy access to an array of shopping, dining, and entertainment options. With its perfect blend of serene living and convenient access to urban amenities, Oakland Park is more than just a place to live; it’s a lifestyle choice that embodies the best of Florida living. Come discover your dream home in Oakland Park today!

Newest Oakland Park Homes with Pool Community Features

$675,000
3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Seller may consider buyer concessions if made in an offer ~ LIKE-NEW LIVING in one of Winter Garden’s most sought-after communities! Just four years old, this beautiful DAVID WEEKLEY SUMMERTON MODEL is located in McKinnon Square within award-winning Oakland Park – and the GOLF CART IS INCLUDED! High ceilings, abundant natural light and an OPEN CONCEPT design create a bright, welcoming interior made for everyday living and entertaining. At the heart of the home, the GOURMET CHEF’S KITCHEN flows seamlessly into the main living and dining spaces, while the inviting FRONT PORCH adds to the neighborhood feel Oakland Park is known for. All of the bedrooms are upstairs along with a versatile BONUS/LOFT offering endless possibilities as a home office, playroom, media space or second living area. Life here extends well beyond the front door – Oakland Park is a GOLF CART-FRIENDLY COMMUNITY offering a clubhouse, COMMUNITY POOLS, parks, playgrounds, a dog park and recreational amenities, plus easy access to the WEST ORANGE TRAIL and LAKE APOPKA. Cruise by golf cart to HISTORIC DOWNTOWN WINTER GARDEN for award-winning restaurants, boutique shopping, breweries, coffee shops, live entertainment, seasonal festivals and the popular Winter Garden Farmers Market. Everyday convenience is equally impressive, with the elementary school approximately .5 miles away, middle school 1.1 miles, high school 3 miles and Orlando Health Hospital approximately 1.8 miles away. Hamlin Town Center, SR-429, SR-50 and Florida’s Turnpike are easily accessible, with shopping, dining, Disney and Central Florida attractions within reach. MOVE-IN READY, nearly new and complete with a golf cart, this Oakland Park home delivers the lifestyle that makes Winter Garden such a desirable place to call HOME!

923 Colie Alley, Winter Garden
$1,649,999
6 Beds ⋅ 5 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Virtually Staged. Modern Luxury in the Heart of Winter Garden’s Golf Cart District! Welcome to 1101 Eagles Pass Way, an exquisite 6-bedroom, 5-bathroom home situated on a desirable corner lot in the sought-after Oakland Park community—one of the few neighborhoods within Winter Garden’s beloved golf cart district. Just one block from Lake Apopka and less than two miles from the historic downtown shops and restaurants, this home beautifully blends modern luxury with small-town charm. Step inside to discover designer finishes and thoughtful craftsmanship throughout. The gourmet kitchen features top-end Monogram appliances, including a 36” dual-fuel range, warming oven, and a 48” side-by-side refrigerator and freezer. Upgraded quartz countertops, a brick backsplash and hearth with built-in electric fireplace, and engineered hardwood floors elevate the open-concept main living areas. Additional luxury touches include Brizo faucets, custom plantation shutters, and floating shelving systems in every bedroom closet. The owner’s suite offers a spa-inspired retreat with a 6-foot soaking tub, while the upgraded pantry with butcher block countertop, dimmer switches, and ceiling fans throughout enhance everyday comfort. An in-law suite featuring a full bath, family room, and a private staircase above the garage provides the perfect space for guests, extended family, or a private home office. Enjoy peaceful mornings and sunset evenings from the screened front and side porches, adding to the home’s charm and livability. Located in Oakland Park, residents enjoy resort-style amenities including two community pools, multiple parks and playgrounds, scenic walking and biking trails, a clubhouse, and direct access to the West Orange Trail. With tree-lined streets, lake views, and friendly front-porch living, this award-winning community captures the very best of Winter Garden living.

1101 Eagles Pass Way, Winter Garden
$859,000
3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
OAKLAND PARK---a PARADE of HOMES winning community! Nestled beneath a canopy of mature trees and perfectly positioned across from a PARK, this charming home welcomes you with a spacious covered front porch where you can relax and enjoy nature and the peaceful surroundings. Thoughtfully designed with warmth and character throughout, the home features rich WOOD flooring, beautiful custom ACCENT WALLS, and a stunning staircase that adds style and sophistication to the inviting interior. Offering 3 bedrooms, 2.5 baths, a dedicated formal dining space, and a small bonus area upstairs suitable for an OFFICE—-a functional yet elegant layout, this home was designed with the homeowner in mind. The kitchen is beautifully appointed with stone countertops, tile backsplash, abundant cabinetry, and a built-in desk area that adds both charm and convenience. A dedicated COFFEE BAR creates the perfect morning retreat, while the walk-in pantry and additional secondary pantry provide exceptional storage space. The downstairs spacious laundry room is equally impressive, featuring a utility sink and extensive counter space ideal for organization and everyday functionality. The living room is embraced with natural light from an abundance of windows overlooking the backyard, while extended FRENCH DOORS create a seamless connection to the covered outdoor living space, enhancing the home’s warm and welcoming atmosphere. A convenient half bath and entry door are located adjacent to the covered porch, offering seamless indoor-outdoor living. The outdoor space is already enhanced with pavers, creating a polished and low-maintenance setting ideal for entertaining, relaxing, or future customization. With ample room to design and build a POOL, the backyard offers endless possibilities to create your dream oasis. The upstairs PRIMARY SUITE offers a relaxing retreat complete with dual sinks, an oversized walk-in shower, linen closet, a separate private water closet, and a generously sized walk-in closet. Two additional bedrooms and one full bath are located upstairs. Blending comfort, charm, and thoughtful design, this beautifully customized home offers an exceptional opportunity to enjoy cozy living spaces, stunning outdoor potential, and timeless character in a picturesque PARK setting. Just a short GOLF CART ride away, you’ll find the charm and vibrancy of Historic Downtown Winter Garden, known for its award-winning restaurants, boutique shopping, outdoor dining, farmers market, & events. This is more than a home — it’s a lifestyle defined by luxury, walkability, connection, & the unmatched charm of Winter Garden living. This golf-cart-approved WATERFRONT community offers year-round activities, from golf cart parades to book clubs & social gatherings, making it an extraordinary place to call home. The community features parks, playgrounds, two pools, a clubhouse, dog park, & trails, including access to the 22 mile long WEST ORANGE TRAIL. Don’t miss this opportunity to live in one of the areas most sought-after neighborhoods, with easy access to interstate travel, shops, restaurants, golf courses, & world-renowned theme parks!

907 Easley Avenue, Winter Garden
$2,098,000
4 Beds ⋅ 4 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Pre-Construction. To be built. Pre-Construction. To be built. A Custom home in the Reserve of the sought-after Oakland Park community. This is a RCB Homes custom-built two story, four-bedroom, four-bath floor plan that you will customize with all the luxury finishes you will pick yourself! The floorplan is an open concept design, but you can still make changes to the floorplan if you want! The lot affords beautiful views of Lake Apopka on a secluded cul-de-sac. The community is conveniently located minutes away from downtown Winter Garden, with a plethora of restaurants, shopping, and more. If outdoor recreation is up your alley, enjoy the various walking trails in the community or explore the 22-mile paved West Orange Trail connecting Oakland/Winter Garden to Apopka! Seize your opportunity to become a part of the luxury lifestyle inside Oakland Park with its multiple community living spaces, pools, playgrounds, and more. Don't settle for a community or home that doesn't have your wants and needs; build this home one to your specifications. Call us to find out more!

1258 Ridge Lake Way, Oakland
Start Your Search