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, located in beautiful Orange County, offers a perfect blend of suburban tranquility and modern conveniences, making it an ideal place to call home.

One of the standout features of Oakland Park is its stunning homes, many of which come with private pools, allowing residents to enjoy the Florida sunshine in style. Imagine relaxing by your own sparkling pool, hosting summer barbecues, or enjoying a refreshing dip after a long day. The allure of a poolside lifestyle is just one of the many reasons families and individuals are drawn to this exceptional community.

Beyond the beautiful homes, Oakland Park boasts a range of community features that enhance the overall living experience. Residents have access to well-maintained parks, walking trails, and recreational areas, perfect for outdoor activities and family gatherings. The community fosters a friendly atmosphere, where neighbors become friends and families can thrive.

Conveniently located, Oakland Park provides easy access to Winter Garden's vibrant downtown, featuring a variety of shops, restaurants, and entertainment options. With top-rated schools and nearby amenities, everything you need is just a stone’s throw away.

Whether you’re looking for a peaceful retreat or a place to build lasting memories with family and friends, Oakland Park offers a welcoming environment that truly feels like home. Come discover the charm of Oakland Park, where your dream home with a pool awaits!

Newest Oakland Park Homes with Pool Community Features

1021 Huntspoint Street, Winter Garden
$865,000
4 Beds ⋅ 4 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
RARE opportunity in Oakland Park, a Parade of Homes-winning community: a 2018 home with approximately $145K in owner upgrades that YOU and your family can enjoy, including a premium SOLAR plus whole-home battery system (paid off at closing). This home is PRICED to MOVE. Offering 4 bedrooms, 3.5 baths, and 2,445 square feet, with a flexible main-floor suite, loft, dining space, tile flooring, newer AC (2024), and a screened balcony, it is built for everyday living, entertaining, and working from home, and is fully fenced for privacy. The main-floor suite is framed by statement doors, with a built-in MURPHY BED and private patio. It works as a 4th bedroom, guest suite, or home office, ideal for multigenerational living. Upstairs, each bedroom enjoys its own en-suite bath, and one opens to the screened balcony. The PRIMARY SUITE includes dual sinks, ample counter space, a soaking TUB, tiled shower, and walk-in closet. The stylish, highly functional kitchen features QUARTZ counters, tile backsplash, custom wood-trim island, and a water filtration system, with APPLIANCES UPDATED in recent years (Bosch dishwasher, LG ThinQ refrigerator, built-in oven and microwave). Just off the kitchen are two pantries, a built-in desk, and extra under-stair storage. CUSTOM finishes add warmth throughout: an electric FIREPLACE with shiplap in the living area, board-and-batten in the primary bedroom, a shiplap accent wall in the secondary bedroom, custom staircase wall, plantation shutters, updated lighting, and a remodeled half bath. Custom closet systems in every bedroom, two linen closets, multiple pantry closets, and added laundry-room cabinetry with a drying rack keep everything organized. The standout garage offers a dedicated mini-split AC, EV charger, epoxy flooring, and abundant built-in storage with an overhead lift system, and connects to the home by a covered walkway, a rarity in the neighborhood. The crown jewel: a premium 12.64 kW solar and whole-home battery system (installed 2024, an approximately $86K value paid off at closing) with 32 Mission Solar panels and four Enphase IQ Battery 5P units (~20 kWh storage) that can power virtually the entire home during outages. Enjoy a monthly energy bill of about $35. A short GOLF-CART ride from Historic Downtown Winter Garden's award-winning restaurants, shopping, farmers market, and events. This golf-cart-friendly waterfront community offers two pools, a clubhouse, parks, playgrounds, a dog park, and access to the 22-mile West Orange Trail, with easy reach to interstates, golf, and world-renowned theme parks. More than a home, it is the Winter Garden lifestyle.

1021 Huntspoint Street, 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
910 Trowman Aly, Winter Garden
$638,000
3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Welcome to this modern 3-bedroom, 2 and 1/2-bath residence, 1650 square feet located in McKinnon Square at Oakland Park, nestled within Winter Garden's coveted golf cart district. This Home has a nice welcoming front porch and showcases timeless architecture, upscale designer finishes. Step inside to discover soaring ceilings, beautiful luxury vinyl plank flooring throughout the main living areas. At the heart of the home on the 2nd Story, the Executive kitchen features custom cabinetry with updated hardware, quartz countertops, an island, a gas range, vent hood, tile backsplash, and abundant storage. The open-concept design flows effortlessly into the spacious family room with a Balcony to have coffee in the morning or tea in the evening. The upstairs has a lofty feel has a nice living space. Cathedral ceilings, walk-in closet. One of Winter Garden's most desirable lifestyles. This award-winning, master-planned community of Oakland Park features tree-lined streets, scenic parks, resort-style pools, playgrounds, and miles of walking and biking trails, including direct access to the renowned West Orange Trail. Residents enjoy a true neighborhood atmosphere just a golf cart ride from Historic Downtown Winter Garden, where you'll find award-winning restaurants, boutique shopping, breweries, coffee shops, live entertainment, and the nationally recognized Winter Garden Farmers Market close to Winter Garden Village at Fowler Groves the outdoor Mall and the Orlando International Airport. With convenient access to Florida's Turnpike, SR-429, 408, to downtown Orlando, and Central Florida's world-famous attractions and Themed Parks, this exceptional residence offers the perfect blend of luxury, convenience, community, and lifestyle.

910 Trowman Aly, Winter Garden
1101 Eagles Pass Way, Winter Garden
$1,644,999
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
907 Easley Avenue, Winter Garden
$840,000
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
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