Oakland Shores Homes with Shingle Roof

Welcome to Oakland Shores, a hidden gem nestled in the heart of Maitland, Florida, within the enchanting Seminole County. This charming subdivision is a perfect blend of suburban tranquility and urban convenience, offering residents a serene lifestyle without sacrificing access to the vibrant culture and amenities of nearby Orlando.

Oakland Shores features an array of beautiful homes, many adorned with classic shingle roofs that not only enhance their aesthetic appeal but also provide durability and protection against the Florida elements. These homes are designed with families in mind, showcasing spacious layouts and inviting outdoor spaces that encourage relaxation and social gatherings. Whether you’re enjoying a sunny afternoon in your backyard or taking a leisurely stroll through the picturesque streets, Oakland Shores fosters a sense of community that is hard to find elsewhere.

The location of Oakland Shores is a significant draw for potential homeowners. With close proximity to top-rated schools, shopping centers, and recreational parks, residents can enjoy the best of both worlds. The nearby Lake Maitland offers a plethora of outdoor activities, from boating to picnicking, ensuring that you’ll always have something fun to do with family and friends.

If you’re looking for a welcoming neighborhood that combines beautiful homes with a vibrant community spirit, Oakland Shores is the perfect place to call home. Explore the enchanting residences today and discover why so many have chosen to make this delightful subdivision their forever home. Experience the charm of Oakland Shores, where comfort meets convenience in the heart of Florida.

Newest Oakland Shores Homes with Shingle Roof

$825,000

3 Beds ⋅ 3 Baths ⋅ O6437275 MLS

**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to this gorgeous, move-in-ready 3-bedroom, 2.5-bath POOL home in the desirable Oakland Shores neighborhood of Maitland! Situated on an oversized, beautifully landscaped lot, this exceptional home welcomes you with mature landscaping, a large circular driveway, and additional side parking ideal for a boat or RV. Inside, you’ll immediately appreciate the light and bright open feel, luxury vinyl flooring, and crown molding throughout the main living areas. The formal living room flows seamlessly into the dining and family rooms, all overlooking the spectacular resort-style pool and backyard. The expansive sparkling pool is surrounded by a custom pavered patio with multiple spaces for lounging, dining, and entertaining, while the generous green space and privacy create your own backyard retreat. The beautifully appointed kitchen features quartz countertops, white shaker cabinetry, stainless steel appliances, a center island with sink, walk-in pantry, and a charming dining nook with custom seating. The spacious primary suite offers direct pool access, a huge walk-in closet with a custom organizing system, and a spa-like ensuite bath complete with dual sinks, vanity, garden tub, and separate glass-enclosed shower. Two generously sized secondary bedrooms share an upgraded full bath, while an additional upgraded half bath provides convenience for guests. A well-designed interior laundry room includes built-in cabinetry and direct access to the backyard. One of the home’s most versatile features is the large bonus room, complete with a spacious walk-in, air-conditioned storage room. Whether you envision a home gym, classroom, office, creative space, or potential mother-in-law suite, the possibilities are endless. Recent updates provide additional peace of mind, including a roof and septic system replaced in 2017. The septic was recently cleaned in 2025 with the filter replaced. Additional upgrades include electrical, fencing, water heater, pool pump, interior paint, brand new Carrier HVAC system, irrigation pump, plumbing, and windows. Oakland Shores offers a wonderful neighborhood setting for walking and includes deeded access to Lake Faith, a non-motorized lake great for paddle boarding and kayaking, with a community access point on Lake Shore Drive. Conveniently located near shopping, dining, major roadways, and within a mile of the newly planned Maitland Trader Joe’s, this home combines comfort, versatility, privacy, and an ideal Maitland location. With its beautiful pool, oversized lot, extensive updates, and flexible living spaces, this is one you won’t want to miss!

505 Oak Lane, Maitland

$578,000

3 Beds ⋅ 4 Baths ⋅ O6394681 MLS

Virtually Staged. Welcome to 502 Oak Lane in Maitland, a beautifully updated 3 bedroom, 3.5 bathroom pool home offering comfort, character, and peace of mind. Thoughtfully improved throughout, the home features fully updated plumbing, including the replacement of the original cast iron plumbing, along with a brand-new pool pump. Inside, you will find a well-designed layout with spacious living areas, updated finishes, and abundant natural light. Each bedroom has access to its own private bathroom, providing excellent privacy and flexibility for family members, overnight guests, or a home office. The home has been meticulously maintained and is truly move-in ready. Step outside to your private backyard oasis, complete with a swimming pool that is perfect for relaxing, entertaining, or enjoying Florida living year-round. Located on a quiet street in Maitland, the home is approximately 10 minutes from Winter Park and offers convenient access to major highways, shopping, dining, and everyday conveniences. This is a rare opportunity to own a fully updated pool home in one of Maitland’s most desirable and centrally located areas.

502 Oak Lane, Maitland

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