Maitland Real Estate Search

Maitland Homes for Sale

With an incredible location in the Orlando Metro Area, the small community of Maitland, Florida, is a great place to live in Orange County. Roughly six miles north of Orlando and eighty-one miles northeast of Tampa, Maitland homes are in proximity to many exciting attractions, including a senior center, a public library, and several art centers. Likewise, there are many outstanding recreation opportunities in Maitland, such as swimming, boating, baseball, hiking, biking, fishing, soccer, and water sports. These opportunities are found at places like Nina Canal in Covered Bridge Park on Old Horatio Avenue and Bellamy Park on Kentucky Avenue. Lake Sybelia Point’s Homer Hough Park is another great example, as is Hill Park on Hillcrest Avenue.

Specific points of interest near Maitland homes include the RDV Sportsplex, Maitland Community Park, the Enzian Theater, Waterhouse Carpentry Museum, and the Maitland Art Center. Maitland residents also enjoy easy access to multiple modes of transportation, including the nearby Orlando International Airport. As one of Central Florida’s oldest incorporated municipalities, Maitland also encompasses a gorgeous historic corridor consisting of heritage homes in the heart of the community and stretching out and into the Lake Catherine and Lake Lily areas. 

The attractions, services, and amenities in Maitland collectively add to the appeal of the city’s housing options. Real estate in Maitland is diverse and includes attached housing like apartments and condos, as well as semi-detached options like townhomes. Likewise, you’ll find an array of detached single-family homes for sale in Maitland of many floor plans, styles, sizes, and ages. For specific details about available properties in Maitland, Florida, please connect with us today, and we will happily help you with your Maitland home search.

Our website features the best Maitland real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

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Newest Maitland Homes and Condos for Sale

$4,399,000
4 Beds 5.5 Baths Lake Maitland Manor SubDv. 32751 Zip Code
Embrace the epitome of luxury living with this extraordinary lakefront estate located in the heart of Maitland, where endless possibilities await. This expansive custom-built residence, spanning nearly 6,000 square feet, presents the rarest of opportunities. Whether you envision moving right in, updating the existing custom residence, or building anew on this coveted 2-acre high-and-dry lakefront lot, the potential is limitless. The maturely landscaped driveway meanders to a circular paver roundabout leading you to the custom leaded glass entry doors. The foyer makes way to the expansive light filled formal living room boasting high ceilings, a wall of windows, a gas fireplace, and spectacular views of the lush backyard rolling gently down to unobstructed views of Lake Maitland. The chef’s kitchen, equipped with custom cabinetry, a stunning copper stove hood, double ovens, and spacious countertops, making way to the open glass breakfast nook inviting you to create a culinary haven tailored to your every desire. Adjacent to the kitchen, lies the formal dining room, complete with slate tile and majestic front garden vistas! The first-floor primary bedroom, with its panoramic water views, dual walk-in closets, and spa-inspired bathroom, presents an opportunity to enjoy a luxurious retreat that exceeds your expectations. Just outside the primary bedroom is a stately office with custom wood paneling, a morning bar, and two-story bookshelves complete with a sliding ladder and French doors that lead to the covered porch with stunning lake views. Downstairs, two additional bedrooms and a Jack and Jill bathroom offers ample space for family and guests, while the upstairs in-law suite, complete with a private balcony overlooking the lake provides a spacious family room area, and full kitchenette, making it the perfect retreat for your most coveted guests, they'll never want to leave their very own sanctuary! The media and game room is second to none boasting an oversized wet bar with counter seating, an additional full bath and a generous closet behind hidden glass doors. The oversized 4-car garage with a spacious storage room ensures that your vehicle and hobby needs will all be met. The nearby oversized laundry area and mudroom, complete with an additional full bathroom is beyond practical. Relish in early morning sunrises, daily duck visits from your massive screened-in rear patio, and private composite dock with a covered boat lift assures you appreciate the extraordinary views of Dog Island, Isle of Sicily, and the Winter Park Racquet Club. The original regulation-size tennis court, partly shaded by an abundance of Florida citrus trees, has the potential for pickleball courts, basketball or multi-sports court, offering a blank slate for creating your ultimate recreational space. Situated walking distance from famed Luke's Kitchen and Bar, Antonio’s, and other fine restaurants, and with Winter Park’s--Park Avenue Boutiques and restaurants only 2.5 miles away, this extraordinary lakefront estate presents a once-in-a-lifetime opportunity to build or update your dream home in one of Central Florida’s most sought-after locations. Seize this chance to make your mark on luxury waterfront living and create a legacy that will endure for generations to come!

580 Manor Road, Maitland

$1,090,000
5 Beds 4 Baths Dommerich Estates 4th Add SubDv. 32751 Zip Code
Welcome to 1020 Tuckaseegee Trail where your mailman still delivers the mail on foot to your doorstep. Tucked away in the back of sought-after Dommerich Estates. You are footsteps away from the boardwalk to Maitland Community park and to the neighborhood boat ramp. Launch your boat or kayak at Lake Minnehaha and tour the Chain of Lakes. You will be walking distance to school and the baseball fields that will have you feeling like you are living in The Sandlot days. This home was completely renovated in 2018. 2,114 sq ft in the main home with 4 bedrooms and 3 baths. The inviting kitchen is open concept with a large island and wood burning fireplace perfect for entertaining your guests. All new duct work in 2020 and electrical was updated in 2019. Two sets of French doors lead you to the back lanai and a heated pool with a spa. Large spacious backyard with a firepit and garden bed. Overlooking the pool is a brand new 489 sq ft detached guest home that overlooks the pool and was built in February 2023 with all you need for your in-laws or out of town guests. There is a private entrance and driveway for the guest home. Whole home water filtration system and whole home generator with 2 propane tanks. You can swim year around with a pool heater purchased in 2020. Large oversized corner lot with the perfect view to catch the sunsets from your front porch. Come see for yourself and fall in love with Dommerich Estates. There are countless events that happen right outside your door including neighborhood 5ks, a massive Halloween celebration, neighborhood gatherings at the lake lot, Farmer’s markets and First Fridays in downtown Maitland just to name a few. Take a quick bike ride to the SunRail station where you can hop on the train to Park Ave. in Winter Park or catch a Magic game in downtown Orlando. Top rated schools- Dommerich Elementary, Maitland Middle and Winter Park High. So much to offer and ready for a new owner!

1020 Tuckaseegee Trail, Maitland

$289,000
3 Beds 3 Baths Park Lake Grove Condo Ph C SubDv. 32751 Zip Code
Experience the epitome of lakeside living in beautiful Park Lake Grove with this remarkable Maitland condo. Discover the perfect fusion of urban convenience and serene comfort within this meticulously maintained, rare 3-bedroom, 3-full bath townhouse, boasting not one, but two master suites. Nestled in the heart of picturesque Maitland, FL, this cozy abode offers 1,328 square feet of carefully crafted space, blending functionality with style seamlessly. The community covers essential maintenance services including pool, roof, exterior, and landscape upkeep, ensuring a worry-free lifestyle. Plus, with lake access to the dock included, you'll have the luxury of enjoying the tranquility of the water just steps from your door. Step inside to be greeted by the inviting embrace of tile and laminate flooring, combining aesthetic charm with easy maintenance. The open-concept layout effortlessly connects the well-appointed kitchen to the welcoming living room, creating an ideal space for entertaining loved ones. Relish in the spacious master ensuite complete with a walk-in closet and a serene outdoor balcony, offering a quiet retreat after a long day. But the true highlight of this condo awaits outdoors on the delightful patio, perfect for enjoying your morning coffee or hosting memorable al fresco dinners. Beyond your private sanctuary, you'll find convenience at every turn, with an array of attractions, shops, and dining options just moments away. Maitland's scenic beauty, serene lakes, and vibrant arts scene provide the perfect backdrop for your new home. Experience the warmth of the neighborhood's friendly community spirit, where city life meets tranquility seamlessly. Don't miss your chance to make this Maitland gem yours. Schedule a showing today and discover the convenience and comfort that awaits. With a recently installed roof and new fence, along with a freshly painted exterior, this home is ready for you to move in and make it your own. All of this nestled in the meticulously maintained community of Park Lake Grove, conveniently located near I-4, Winter Park Village, Rollins College, and a plethora of shopping and dining options. Come see it for yourself and fall in love today!

1627 Gulfview Drive Unit 441-B, Maitland

$869,000
4 Beds 2 Baths Hidden Estates Unit 2 SubDv. 32751 Zip Code
Welcome to your own private oasis in the charming neighborhood of Hidden Estates. This home is located on a cul-de-sac, nestled on a lot just under an acre in size, adorned with mature oak trees. As you step through the foyer, you will be greeted by an inviting open floorplan featuring a spacious great room and dining room bathed in natural light. The spacious kitchen overlooks the great room and dining room. It boasts a large walk-in pantry, granite countertops, soft close drawers and ample cabinetry. Off of the kitchen, you will find the indoor laundry room with additional storage space. The den/office provides a versatile space for work or relaxation. The great room features 2 sets of sliding doors which open to the expansive outdoor area. There are four bedrooms tucked away to the left of the foyer as you enter the home. A centrally located bathroom features a double vanity sink and a bathtub shower combo. The primary retreat has a stunning view of the backyard and has a walk-in closet and an en-suite bathroom with a walk-in shower. Step outside into your own private sanctuary. You can lounge under the covered patio area, take a swim in the beautiful pool and admire the serene pond view. Enjoy gardening or relaxing around a firepit for cozy evenings under the stars. The home also offers RV parking and 30amp electrical hookup is available. Recent updates include: A/C 2022, water heater: 2023, roof and home renovations: 2015, EV charger, security system owned. This home is zoned for great Seminole County Schools. Conveniently located close to I-4, the Maitland Sunrail Station, Altamonte Springs and is located close to Winter Park, this home offers easy access to all of the wonderful attractions that the Orlando area offers. Don't miss the opportunity to make this hidden gem your own!

410 Melanie Way Way, Maitland

$199,500
2 Beds 1.5 Baths Cherrywood Gardens SubDv. 32751 Zip Code
Welcome to your new home in the heart of Maitland! Nestled in the charming and conveniently located Cherrywood Gardens community, this delightful 2-story condo offers both comfort and convenience. As you step through the ground floor entrance, you'll appreciate the ease of access with 2 designated parking spaces right at your front door, along with ample visitor parking for guests. With only 4 buildings in this secluded and intimate community, you'll enjoy a sense of privacy while still being part of a vibrant neighborhood. Explore the nearby amenities within minutes - from parks and coffee shops to fine dining and shops, everything you need is within a mile or so radius. Commuting is a breeze with the new SunRail station, Maitland Community Park, and Maitland City Cultural Center just a stone's throw away, not to mention easy access to I-4 and Highway 414. Cherrywood Gardens exudes a serene energy with its landscaped outdoor spaces, perfect for leisurely strolls with family or small pets. Take a dip in the eye-catching community pool or host gatherings in the clubhouse. Inside, the condo boasts a spacious dining and living room combo adorned with bamboo wood flooring - an ideal space for entertaining guests. The cozy kitchen features tile floors, granite countertops, and modern cabinets, providing both style and functionality. Step out onto the enclosed rear patio, which opens up to a courtyard, offering a warm spot for your morning coffee or al fresco dining. Adjacent is a multipurpose utility room with washer and dryer hookups, adding to the convenience of everyday living. Don't miss out on this wonderful opportunity to own a beautiful condo in one of Maitland's most sought-after communities. Schedule your showing today and make this your new home sweet home!

218 Cherrywood Gardens Drive Unit 218, Maitland

$359,900
3 Beds 2.5 Baths Villas Lake Destiny SubDv. 32751 Zip Code
One or more photo(s) has been virtually staged. AMAZING LOCATION for this updated 3 Bed, 2.5 Bath townhome in the heart of Maitland tucked away in the secluded, Gated Community of Villas of Lake Destiny. Upon entering the Private Courtyard with lush landscaping, you will feel right at home. At the end of the entry hall is the spacious, bright Living Room with soaring 2 story ceilings and Transom Window above the massive Sliding Glass Doors that lead out to the private 22' x 10' Patio surrounded by more lush landscaping and mature trees making it the perfect place to relax and unwind. The large Dining Area is located adjacent to the Living Room and Kitchen which features Corian counters with a Breakfast Bar, Dual Oven Range, Built-In Microwave, plenty of counter space and storage. Head up to the second floor where you will find all the bedrooms featuring High Ceilings. The owner's suite offers a Walk-In Closet AND Wall Closet. The updated En-Suite Bath has a Granite Top double sink vanity with a Corner Cabinet and a Glass Enclosed Shower. Bedroom two has Cathedral Ceilings and access to the Updated Hall Bath while the third bedroom has a Vaulted Ceiling. Completing your future home on the first floor are a Half Bath, Utility Closet with Washer and Dryer, a large Under Stair Storage Closet, a Cozy Space overlooking the Courtyard that can be used as a Breakfast Nook and an oversized One Car Garage. Additional features include Tile Roof replacement in 2023, A/C in 2022 and newer Pella Double-Paned Low-E Windows and Sliding Door. Community amenities include a Lakefront Pool and Spa, Community Boat Ramp and Tennis Courts. Villas at Lake Destiny is located Close to Maitland Office Park, I-4, 414 Maitland Exchange, RDV Sportsplex, Hospitals, Shopping and so much more!

1010 Winderley Place Unit 131, Maitland

$4,995,000
6 Beds 5.5 Baths Maitland Forest SubDv. 32751 Zip Code
Pre-Construction. To be built. Stunning modern estate perfectly positioned along the shores of the Winter Park Chain of Lakes. This architectural masterpiece, designed and built by Vimaro Homes is sure to be a showstopper. As you pull up the elegant circular driveway you’re greeted by lush landscaping, and an oversized three car garage. Stepping though the front doors, your eyes are immediately drawn to the bright open floor plan and exquisite architectural details. From the custom three-story staircase to the double sided fireplace and wall of windows overlooking the lake this is truly a bespoke property. The chef in the family will love the open kitchen with its top-of-the-line appliances, custom cabinetry, porcelain counter tops, oversized pantry, and massive center island overlooking the great room. The primary bedroom suite features a bird’s eye view of the lake, an exquisite bathroom that will rival even the most prominent spas, and a huge walk-in closet to house even the largest show collection. Additional features include a home office, two laundry rooms, a guest suite on the first floor, 4 additional bedrooms on the second floor, and a game room with a powder bath on the lower level. For entertaining, simply lower the retractable screens on the covered lanai and open the entire back of the home bringing the outdoors in. Exterior amenities include a summer kitchen, oversized outdoor patio with glass railings, and an amazing pool with a double-sided infinity edge. Last but not least, there is an impressive staircase leading down to the back yard and your own private boat dock. The massive peninsula lot steals the show with one-of-a-kind lake views and plenty of room for a detached guest house or additional garages for the car enthusiast. Don’t miss this opportunity to enjoy living on the Winter Park Chain of lakes for a fraction of typical the cost.

656 Bentley Lane, Maitland

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