Homes for Sale Near Maitland Middle in Maitland - 47 homes

Remarks: Under contract-accepting backup offers. In the heart of Dommerich, this thoughtfully renovated mid-century pool home offers deeded access to the Winter Park Chain of Lakes & a well-executed floor plan designed for everyday living. Set on a .20-acre lot measuring 79’ x 111’, the home balances indoor comfort with outdoor livability, beginning with a welcoming front entry that opens to a casual foyer. To the left is a shared formal living and dining space filled with natural light from large-format windows. Wide plank engineered wood flooring, charming built-ins & updated finishes continue throughout the main living areas, creating a cohesive & visually consistent interior. Toward the back of the home, the layout transitions to a family room & adjoining Florida room, which, when used together, create a spacious secondary living area, or may function separately as a family room, casual dining area, office or reading room, all overlooking the pool and functionally connected to the kitchen. The kitchen is positioned at the center of the home & features white shaker cabinetry, grey quartz countertops, a large island with a butcher block countertop, seating and storage on all sides, a vent hood over the range, stainless steel appliances & a large white ceramic single-bowl farmhouse sink with a pull-down commercial-style faucet, along with windows overlooking the pool & backyard. The home offers an ideal split-bedroom plan, with the primary suite located on the back left side of the home and added in 2018 by Winter Brothers Construction. The suite includes a spacious bedroom with recessed lighting, separate closets with built-in organization & a well-appointed bath with dual vanities, a freestanding soaking tub, a glass-enclosed walk-in shower with rain shower head & a private water closet. On the opposite side of the home are three additional bedrooms, including one with an en-suite bath designed with a pedestal sink, wall-mounted storage & a glass-enclosed walk-in shower, along with a full hall-entry bath which comes with a tub/shower combination & new vanity (2026). Highlights of the backyard include a paver deck, saltwater swimming pool with a generous shallow shelf, child safety fence, play set, raised garden bed, lawn space for people and pets and a mature peach tree that produces fresh peaches. The home also features an attached two-car garage with a laundry area, professional landscaping and a newly installed white privacy fence with gated access on both sides. In addition to its charm & interior updates, the home offers meaningful system improvements, including electrical panels (2018), two HVAC systems (2018 and 2022), a full re-pipe to PVC/CPVC, roof replacement (2017–2018) & an electric water heater (2018). The property owner has the option to join the Dommerich Estates Beach Civic Association, which provides access to a private boat ramp, picnic area and lakefront amenities on Lake Minnehaha. Residents also enjoy convenient access via the neighborhood boardwalk to Maitland Community Park, offering tennis and basketball courts, trails, pavilions and year-round activities. Zoned for Dommerich Elementary, Maitland Middle and Winter Park High and located just minutes to Park Avenue, Lake Lily, the Maitland SunRail station and major roadways, this is an opportunity to own a move-in ready home in a well-established neighborhood with strong school zoning, a true sense of community and lake access to the Winter Park Chain of Lakes.

Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)

Listing Agent: Padgett Mccormick (407-645-4321)

Remarks: Under contract-accepting backup offers. RARE opportunity to own a Maitland Shores home offering access to Lake Minnehaha AND the Winter Park Chain of Lakes. Residents enjoy exclusive use of the HOA lakefront park with a fishing dock and paved boat ramp that creates quick access to the Nina Canal and Lake Maitland — the largest lake in the Winter Park Chain. The unique location of this home offers an oversized .34-acre homesite that is thoughtfully landscaped with rare tropical plants, rose gardens, and a peaceful front courtyard complete with a bubbling fountain. Ample driveway and garage space accommodate boat or vehicle storage, ideal for enjoying skiable Lake Minnehaha. Inside, this 3 bedroom, 2.5 bath home offers 2,249 square feet of living space in a split floorplan. A unique highlight of the floorplan is the dual primary suites, each with private access to the screened pool, making the home ideal for multi-generational living. Equally beautiful pool views are also visible from the kitchen, breakfast nook, and spacious family room. If you are staying inside, the family room features a large fireplace that creates a cozy focal point. Just off the family room is the remodeled kitchen that is both bright and functional with abundant cabinetry, granite counters, stainless steel appliances, breakfast bar seating, a built-in desk, and a breakfast nook with patio access. Beauty abounds from the patio with a resort-style screened pool, complete with decorative palms surrounding the pool. Steps from the pool begin the meandering gardens with colorful blooms. To aid the avid gardener is a covered and secure garden shed. With such an expansive homesite - more than 15,000 square feet - possibilities for adding a full workshop or even an Accessory Dwelling Unit/ADU could be explored. Adjacent to this estate is Minnehaha Park, a 7.5-acre City of Maitland park offering multiple tennis courts, pickleball courts, walking trails, picnic pavilions, and playgrounds. While the setting of this property is quiet and serene, the home is minutes from Winter Park shopping and dining; downtown Maitland and Maitland City Centre; I-4 access; and zoned Winter Park High School. Additional home updates include a full roof replacement and AC replacement in 2021, making move-in and insurance smooth and easy. Don't miss this chance to get Winter Park Chain of Lakes access for yourself at this exceptional price!

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Erin Baker (407-719-0030)

Remarks: NEW ROOF, NEWER AC, and NO HOA—this beautifully maintained home on a quiet cul-de-sac offers comfort, charm, and an unbeatable location. Nestled just steps from Lake Sybelia. This property provides a peaceful, scenic setting while still being close to all that Maitland has to offer, including popular local restaurants, shops, and community spots. A short drive takes you to the vibrant dining, shopping, and cultural scene of Park Avenue, making this home perfectly positioned for both relaxation and convenience. Inside, the home features a bright and inviting open floor plan, ideal for entertaining and everyday living. The seamless flow between the living, dining, and kitchen areas creates a spacious feel filled with natural light. Step outside to a large backyard that offers plenty of room for outdoor enjoyment, gardening, or entertainment. With its mature landscaping and charming appeal, this property is a true garden oasis with central living at its best. A fantastic opportunity in a highly desirable Maitland neighborhood—don’t miss your chance to make this home your own.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Sean David (407-712-4698)

Remarks: Don't miss this Great opportunity in the Maitland-Winter Park area! There's Potential for Renovation, Expansion or Development with this property. Imagine the Improvements that can be made for the Future. This is a One Owner Home held be the same family since the 1960s. New roof in 2022. The adjacent property at 220 Alpine is also available for purchase.

Listing is courtesy of: PREMIUM PROPERTIES R.E SERVICE (407-380-2800)

Listing Agent: Beth Hathaway (407-314-1300)

Remarks: One or more photo(s) has been virtually staged. Welcome home to this well outfitted 4 Bed 2.5 Bath home in sought after Maitland. Tastefully upgraded home on a generous lot, with in ground pool. Great upgraded kitchen with custom cabinets for extra storage complemented with upgraded Stainless Appliances and granite counters. Thoughtful upgrades at every turn. Currently zoned for Winter Park HS. Close to everything that Maitland and Winter Park known for, shopping dining and more. Don’t wait, come see today.

Listing is courtesy of: GLORY INTL. REAL ESTATE CO (386-775-7778)

Listing Agent: Patrick D'Agostino (321-467-4555)

Remarks: Welcome to The Moorings, a rarely available lakeside community perfectly positioned across from beautiful Lake Lily. This fully renovated 4th-floor condo combines modern elegance with stunning water views of Lake Maitland, visible right from your living room and screened-in balcony. Inside, you’ll find an open, light-filled layout with white-oak luxury vinyl flooring that sets a clean, contemporary tone. The kitchen has been completely updated with premium appliances, quartz countertops, and brass fixtures, creating a space that’s both stylish and functional. The primary bedroom suite features a spacious walk-in closet and a beautifully finished en-suite bathroom with a large walk-in shower. A second bedroom and full bath offer plenty of room for guests or a home office. Additional conveniences include an in-unit laundry room with washer and dryer, plus elevator access for easy entry. Residents of The Moorings enjoy a host of amenities, including a sparkling community pool, private boat docks, a scenic pier with seating area, a fitness center, and a clubhouse for gatherings. Located just minutes from top-rated restaurants, shopping, and entertainment in Maitland and Winter Park, this condo offers the ideal blend of tranquility and city convenience. Come experience lakefront living at its finest.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Damian Bergler (650-398-5968)

Remarks: Welcome to your dream home! This beautifully updated 4-bedroom, 3 bath residence is in one of the area's most desirable neighborhoods. Enjoy a perfect blend of comfort, style, and functionality, complete with modern renovations and exceptional outdoor living spaces. This corner lot home with multiple picturesque windows provides an abundance of natural light! Generously sized bedrooms provide ample space for family, guests, or a home office and include 2 master suites, both with 2 closets. Enjoy cooking and entertaining in the stunning, updated kitchen featuring modern appliances, sleek countertops, and plenty of storage. Luxury vinyl flooring throughout but still the charm of original wood floors in 3 of the bedrooms. Step outside to your own backyard oasis with a sparkling pool with a waterfall feature and paver patio, perfect for relaxing or hosting gatherings. Eco-friendly and convenient, the property includes an electric vehicle charging station. Tucked away yet ready in a moment’s notice is space for your boat, camper, or recreational vehicles. The attached one car garage offers secure storage for tools, bikes, toys, golf cart, hobbies or projects. You are just steps from the neighborhood lake lot where members can enjoy incredible sunsets, fishing, or launch your watercraft and enjoy a day on the lake. Dommerich Estates has a strong sense of community and was designed and built around A rated schools so walking and biking to school is safe and easy. The City of Maitland, despite its close proximity to Orlando, is vibrant with a small-town feel providing events designed to foster connections among residents with walkable neighborhoods, multiple parks and downtown street parties and concerts!

Listing is courtesy of: BHHS FLORIDA REALTY (407-406-5300)

Listing Agent: Shirley Welch (407-718-1450)