Oakland Shores Homes for Sale in Maitland - 3 homes

Remarks: Under contract-accepting backup offers. Seller has received MULTIPLE OFFERS, and are accepting offers until 5pm on Saturday, JULY 11, 2026. Welcome to your own private resort in the heart of Maitland! Perfectly situated on a beautifully landscaped .27-acre lot in the established Oakland Shores neighborhood, this exceptional three-bedroom, two-bathroom home offers close to 1,800 square feet of thoughtfully updated living space designed for both everyday comfort and unforgettable entertaining. The backyard is truly the star of the show, featuring a spectacular saltwater pool and spa completed in 2023. Designed to impress, this outdoor oasis showcases a stunning Tahoe Blue pebble finish, expansive sun shelf, elegant waterfall and scupper features, dramatic integrated fire bowls, and a heater/chiller for year-round enjoyment. The surrounding travertine pool deck, professionally designed landscape lighting, mature landscaping, and fully fenced backyard create an incredibly private setting, while the Paradise Grill summer kitchen(negotiable with the sale) makes outdoor entertaining effortless. The lush, beautifully manicured landscaping is effortlessly maintained by a 10-zone irrigation system with spray heads, back-flow prevention, and convenient Wi-Fi connectivity, allowing you to monitor and control watering schedules from virtually anywhere. Additionally, a comprehensive underground gutter drainage system directs all roof water to the street, minimizing standing water and protecting the home's foundation and landscaping. Inside, the home is equally impressive with an open and inviting layout enhanced by wood laminate flooring installed in 2019, custom white oak interior doors, crown molding, and large picture windows that frame picturesque views of the backyard retreat. The spacious living room, expanded in 2018, features a beautiful wood-burning fireplace added in 2019 along with custom built-in cabinetry and a built-in desk, creating the perfect gathering space. A newly added laundry/utility room(2026) includes the washer and dryer for added convenience. The kitchen is designed for both function and style with custom wood cabinetry, granite countertops, stainless steel appliances, a pantry, and a center island with seating for three, all overlooking the pool through a large picture window. The private primary suite offers custom cabinetry designed for a king-sized bed, custom blackout shades, white oak closet doors, a ceiling fan, and a beautifully remodeled ensuite bathroom completed in 2026 featuring floor-to-ceiling tile, a custom wood vanity, and a spacious frameless glass walk-in shower. Additional highlights include an oversized paver driveway, two-car garage, and an unbeatable location just minutes from Lake Lily Park, the skiable Lake Orienta boat ramp, I-4, and the shopping, dining, and entertainment destinations of Maitland and Winter Park. This is a rare opportunity to own a home where every day feels like a vacation. ROOF - 2016 HVAC - 2018 ELECTRICAL - 2026 WATER HEATER - 2026

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Amy Turner (407-803-3885)

Remarks: Under contract-accepting backup offers. Back on the market with renewed momentum. Nestled in one of Maitland's most sought-after neighborhoods, this fully renovated 3-bedroom, 2-bathroom home offers the perfect blend of modern comfort and timeless charm, ideal for families ready to make new memories. From the moment you step inside, you're greeted by an abundance of natural light and an open, airy layout that instantly feels like home. The heart of the house, the newly renovated kitchen features sleek stone countertops and new appliances, making it perfect for family meals and holiday gatherings. Step outside to the screened-in patio and picture slow mornings with coffee in hand, or peaceful evenings unwinding from a long day in the spacious backyard. Whether hosting a barbecue or enjoying a quiet night under the stars, this outdoor space is made for relaxation! Located just minutes from top-rated schools, grocery stores, dining, and major highways and less than 10 miles from the natural beauty of Wekiwa Springs State Park. This home offers the convenience you need and the lifestyle you've been dreaming of. Don't miss this opportunity to plant roots and grow in a home that has it all. Schedule your private tour today and discover the warmth, space, and charm waiting for your family.

Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)

Listing Agent: Kay Shilling (407-716-9861)

Remarks: Welcome to 502 Oak Lane in Maitland, a beautifully updated pool home that blends comfort, character, and peace of mind. This fully improved 3 bedroom, 3.5 bathroom home has been thoughtfully updated throughout, including the replacement of the cast iron plumbing, offering both charm and important system improvements. Inside, you will find a well designed layout with spacious living areas, updated finishes, and plenty of natural light. Each bedroom offers its own bathroom, creating privacy and flexibility for guests or family. The home has been meticulously maintained and improved, making it truly move in ready. Step outside to your private backyard oasis featuring a pool, perfect for relaxing afternoons or entertaining friends and family. Located on a quiet street in Maitland, this home offers a great combination of location, updates, and lifestyle. This is a rare opportunity to own a fully improved pool home in one of Maitland’s most desirable areas.

Listing is courtesy of: KRESSLER REAL ESTATE (407-864-2184)

Listing Agent: Andre Kressler (407-864-2184)