Luxury properties in Maitland

For Sale! (Also Available For Lease) Freestanding Building located in Maitland, Florida. Maitland is a suburban city in Orange County, and part of the Greater Orlando area. It is approximately eight miles north of downtown Orlando. Affluent suburban community and strong demographics. There are several condominium and apartment complexes within a half-mile of the subject property including the Q at Maitland, The Village at Lake Lily (250+ units) and Lake Maitland Terrace Condos (181 units). 3 Bank Teller Lines. Parking: 47 Spaces. Dense Retail and Residential Corridor / Surrounding Retailers. Include: Publix, Starbucks, McDonald’s, Walgreens, Chase, PNC, Bank of America. Easy access to 17/92, Maitland Blvd, I-4 and close to Maitland SunRail Station. Excellent visible location | S Orlando Ave with 47,000+ AADT $2,975,000 Active

450 S Orlando Avenue Maitland, Florida

3,851 SqFt 1.03 Acres

Prime mixed-use commercial property perfectly situated between the vibrant cities of Maitland and Winter Park. This centrally located asset offers both visibility and versatility. The listing encompasses a 29-unit multifamily building. The adjacent commercial building 429 E. Kennedy Blvd, and a commercial lot 34 N. West St are also available for purchase—offering incredible potential for future development, expansion, or mixed-use revitalization. Whether you’re an investor or developer, this is a rare opportunity to be part of a growing community with active revitalization efforts. New roof installed in 2023. $2,875,000 Active

421 E Kennedy Boulevard Maitland, Florida

13,577 SqFt 0.85 Acres

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The Winter Park Chain is the context; the shoreline of Lake Minnehaha is the setting. A three-story, columned home opens with an honest, crafted tone: new low-profile concrete tile roof, operable cypress shutters with hand-forged hardware, Chippendale balustrades, and a beveled front door offering almost 6,200 sq. ft. curated for light, views, and everyday lake living. Inside, the home is bright and airy—sunlight does the work here. A direct foyer sightline leads you to a rear wall of French doors that draw in a calm, even glow of natural light across heart-of-pine floors and disciplined millwork: raised-panel wainscot, multi-step crown molding, and architectural beams. Those doors open to a full-length covered lanai; beyond, a heated saltwater pool and spa step down to a deep backyard and a private dock with a covered boat slip and adjoining lounge deck. The kitchen is built to perform so life feels easy. Morning coffee, weeknight pasta, Saturday crowds, it handles all of it. Sub-Zero refrigeration with additional refrigerator drawers, a Thermador six-burner gas range, two dishwashers, and a warming drawer. Granite counters surround a prep island with rinse sink; the peninsula takes the laptops and late plates. A dry bar with wine cooler ties to the dining room for effortless pours and keeps glassware close at hand. Just off the family room, the primary suite claims a quiet corner and opens to the lanai; coffee at sunrise, warm light at day’s end. A large custom walk-in closet answers storage; the bath finishes the suite with tumbled marble, Kohler fixtures, and a cast-iron vintage tub. At the center of the first floor, a deliberate service run keeps daily life organized: powder bath, temperature-controlled wine cellar, a straight sightline to the first of two laundry rooms and the garage entry ending at a private interior stair to a secluded in-law/guest suite with its own full bath. It’s independent, quiet, and ideal for long stays or live-in support. The main stair brings you to a second level arranged with intent. One wing holds three bedrooms around a shared bath. An office corridor carries you to the lake-view great room under a coffered ceiling; triple French doors open to the full-length upper veranda. Another bedroom on this wing enjoys its own veranda access with a full bath close by. Above it all, the third floor is a generous, flexible loft fit for a screening room, billiards or game lounge, studio, gym, or a collector’s library with practical storage tucked to the edges. Quiet systems match the craft: Cat-5 wiring, surround sound, central vacuum, and two laundry rooms. Recent updates keep the essentials current: new HVACs (2020, 2021) and a new dock (2024). Zoned for Maitland Middle and Winter Park High, this home is tuned to everyday rhythm: water out back, light throughout, spaces that work the way you live. From lanai shade to the last light on the lake, it delivers on its promise—an honest, crafted place where the architecture serves the life it keeps. $2,895,000 Active

604 Minnehaha Lane Maitland, Florida

6 Beds 6 Baths 6,163 SqFt 0.77 Acres

Experience the blend of timeless elegance and modern luxury in this Maitland estate a block away from Lake Sybelia. Completely renovated in 2007, every detail of this home exudes sophistication. A spacious paver driveway leads to a two-car garage, framed by lush tropical landscaping, decorative stone accents, and a charming fountain, creating an inviting first impression. The grand foyer welcomes you with soaring ceilings, intricate wrought iron railings, and abundant natural light. The Great Room is designed for both comfort and style, featuring expansive windows, French doors that open to the backyard oasis, and concert speakers embedded in the ceiling for an immersive audio experience. The gourmet kitchen is a chef’s dream, boasting custom cabinetry with glass-paneled doors, granite countertops, a farmhouse sink, and high-end stainless steel appliances. Adjacent to the kitchen, the dining area offers rich hardwood flooring, plantation shutters, concert speakers, and direct access to the outdoor spaces. The first-floor family room provides a cozy retreat with bold tropical-inspired decor, a built-in entertainment center, double-door access to the backyard, and ceiling-embedded speakers. Upstairs, the loft overlooks the grand foyer, offering a versatile space for relaxation. The primary suite is a true sanctuary with rich wood flooring, a private balcony, concert speakers, and a spa-like en-suite featuring a rain shower, shower bench, dual vanities, and a classic clawfoot tub. Outdoor living is elevated with a resort-style pool, a covered patio with elegant columns, and a second-floor balcony that spans the width of the home. The backyard is a private paradise, complete with lush greenery, a pool house, and ample space for entertaining. $1,700,000 Active

255 W George Avenue Maitland, Florida

5 Beds 4 Baths 4,814 SqFt 0.27 Acres

Under contract-accepting backup offers. Sophisticated and timeless, this stunning one-story home was completely reimagined in 2019 by multi-award-winning builder and design through Z-Properties. Taken down to the studs and rebuilt with the finest materials, this split-plan three-bedroom, three-bath residence blends modern design with an inviting, incredible design feel. Gorgeous high grade wood flooring throughout along with expansive windows and walls of glass flood the interiors with natural light, taking advantage of picturesque views! The backyard is a sanctuary setting with Signature Landscape mature landscaping and sparkling pool and separate spa. The open concept design is ideal for daily living and entertaining, with a seamless flow extremely well thought-out living areas. A designer-inspired gas fireplace in the dining area creates a sophisticated and welcoming ambiance, while two sets of glass doors in the living room open to the inviting outdoor living spaces. The stately kitchen is a showpiece, featuring Thermador Pro Series appliances, a Sub-Zero wine tower, and elegant counters that elevate form and function. The primary suite offers a private retreat with a generous walk-in closet and a spa like well-appointed bath. Two additional bedroom suites are equally refined, each with custom closets for optimal storage and organization. Outside, every detail has been thoughtfully curated. The private front courtyard, centered around a tranquil Zen fountain private courtyard, sets the tone for the home's refined elegance. The rear outdoor living area features Brazilian IPE wood decking surrounding the heated saltwater pool, alongside lush landscaping, complete with sculpted hedges and tropical palms, creates a resort-like ambiance. A built-in summer kitchen includes a gas grill and green egg off the kitchen, and flex space is framed by a beautiful bougainvillea hedge for added serenity, ideal for effortless outdoor entertaining. Lastly there is a fully finished garage with indoor/outdoor carpeting and is temperature controlled with its mini-split AC unit. Residents of Hollieanna Shores enjoy deeded lake access to Lake Maitland, part of the prestigious Winter Park Chain-of-Lakes, via a private community boat ramp. Ideally with convenient access to major roadways, this exceptional home offers easy commutes to downtown Winter Park, Orlando and area airports, a sophisticated retreat in one of Central Florida's desirable Maitland/Winter Park hidden gem neighborhoods! $1,485,000 Pending

123 Hollie Court Maitland, Florida

3 Beds 3 Baths 2,004 SqFt 0.17 Acres

Discover a rare opportunity in Dommerich Woods, a distinguished and established Maitland neighborhood celebrated for its rich heritage. Situated on .33 acre of lushly landscaped grounds, this remarkable property welcomes with paver drive and enjoys a tranquil setting along a peaceful creek connecting Lake Minnehaha and Lake of the Woods - creating an atmosphere of natural elegance and privacy. Re-roofed in 2023, this expansive 5 bedroom, 3 1/2 bath residence offers 4,144 HSF, and WHOLE HOUSE WATER SOFTNER, showcases a versatile TWO-LEVEL design, perfectly suited for refined living and gracious entertaining. The main level opens with a foyer leading into a bright, open living and dining area, where CEILING FANS throughout the main level add comfort and elegance. From here, step out onto the COVERED UPPER DECK with sweeping views of the SCREENED POOL, TROPICAL GARDEN, and serene backyard retreat - an ideal setting for morning coffee or evening gatherings. At the heart of the home, the GOURMET KITCHEN blends style and functionality with SOLID WOOD CABINETRY, a built-in WINE REFRIGERATOR and WINE RACK, granite countertops, and a CENTER ISLAND with SEATING, and REVERSE OSMOSIS WATER SYSTEM under the DOUBLE SINK. The adjacent laundry room offers exceptional storage, keeping household essentials organized. For added convenience , a two-car garage with built-in cabinets and workshop area, adjoins the spacious laundry room that has granite counters and washer and dryer. Also on the main level , adjacent to the primary bedroom with en-suite bath, a bedroom has been thoughtfully converted into a large closet featuring a CUSTOM CLOSET system, providing abundant space for wardrobe organization. Both levels feature inviting WOOD-BURNING FIREPLACES that add ambiance to the living spaces. On the lower level, a spacious family room, kitchenette, study/library/office, two bedrooms, full bath and half bath provide the perfect complement to easy living. Along the hallway, built-in wood shelving creates a refined showcase for books, art, or personal collections. While one bedroom includes a custom built in desk- ideal for work or study, a second bedroom adds flexibility for creative projects. This level opens onto the screened pool and patio area, designed for seamless indoor-outdoor living. Outside, tropical plantings, METERED IRRIGATION, and a winding private walkway leads along the soft murmur of the BORDERING CREEK. An added bonus is the storage room located below the kitchen which is approximately 375 sq.ft. Whether hosting guests or enjoying a quiet evening, this private oasis offers the ultimate backdrop for relaxed Florida living. Enjoy the opportunity to join the Dommerich Beach Civic Association with membership options including access to a private picnic area, boat ramp, canoe and kayak storage, and unforgettable evening sunsets. With its rare combination of design, flexible spaces, and an idyllic setting , this residence presents a unique opportunity to experience the very best of Maitland and Central Florida living. All this is convenient to some of Central Florida's finest schools, shopping, restaurants, parks, entertainment, businesses and more! $1,299,000 Active

791 Sequoia Trail Maitland, Florida

5 Beds 4 Baths 4,144 SqFt 0.33 Acres

Classic Colonial Brick Home on highly desired E Adama Drive across from Lake Maitland! 4 bedrooms, 4 Baths, 2 fireplaces-one in Primary bedroom! Full 2nd floor balcony porch with French doors! Terrific home for entertaining! Formal Dining room across from Formal Living room connected by large foyer! Family room/Library with built in shelves on both ends with wood burning fireplace! French door lead to huge covered screened room with summer kitchen. Sip morning coffee while overlooking inground pool! Relax on your huge front porch while watching the squirrels play in the mature trees serenaded by a variety of musical birds! Two car garage with long driveway $1,200,000 Active

1745 E Adams Drive Maitland, Florida

4 Beds 4 Baths 2,378 SqFt 0.34 Acres

Every so often, a property comes along that redefines what lake living can be, and this is that home. Thoughtfully reimagined from top to bottom, this two-bedroom, two-and-a-half-bath residence blends refined design with the effortless lifestyle of the Winter Park Chain of Lakes. Go inside to discover a fully renovated interior anchored by a showstopping 14-foot Cambria quartz waterfall island, the heart of a kitchen designed for entertaining and everyday luxury. The GE Monogram and Café appliance suite, paired with custom solid wood, soft-close cabinetry, makes every detail feel bespoke. Natural light fills the living spaces through PGT double-pane insulated windows and Andersen French doors, framing tranquil garden views that create a sense of calm and privacy. Upstairs, two spacious bedroom suites offer comfort and style, each crafted with high-end finishes and thoughtful touches throughout. Beyond the walls, enjoy the rare privilege of a dedicated boat slip on Lake Maitland, Winter Park’s largest and sought-after body of water. Cruise the connected lakes, explore the historic canals or simply unwind at sunset, all just near home. Built in 1985 and completely transformed with modern systems, including a 2023 HVAC and water heater, this residence offers peace of mind to match its beauty. A one-car garage adds convenience, while every finish reflects care, quality and craftsmanship. Here, luxury isn’t just found inside, it’s a way of life, lived by the water. $995,000 Active

219 Quayside Circle B9 Maitland, Florida

2 Beds 3 Baths 1,459 SqFt 0.56 Acres

Beautifully maintained Maitland home in the gated community of Montacino on Lake Charity. Conveniently located near Maitland City Center, Park Ave, Downtown Orlando, and RDV Sportsplex. Engineered hardwood floors lead from the entry to a formal living and dining room, powder bath, and into the great room with soaring ceilings open to the kitchen and patio. The gourmet kitchen features custom cabinetry, granite countertops, and stainless appliances. The first-floor owner’s suite offers French door access to the private patio, custom closets, and a spa-style bath with dual vanities, soaking tub, and walk-in shower. Upstairs, find three additional bedrooms (one ensuite) and a loft flex space overlooking the great room. Additional highlights include a new brick paver driveway, Pella windows and sliding doors, Carrier A/C, LED lighting, custom patio tile, and epoxy garage flooring. Private backyard with no rear neighbors plus community pool and maintenance-free lawn care. $925,000 Active

1416 Caring Court Maitland, Florida

4 Beds 4 Baths 3,451 SqFt 0.13 Acres

Under contract-accepting backup offers. Welcome to Versailles, where timeless architecture meets everyday ease just steps from the shimmering waters of Lake Minnehaha. This beautifully updated home offers peace of mind with a NEWER ROOF, 4-year-old HVAC, NEW IRRIGATION SYSTEM and APPLIANCES approximately 5 years old. Inside, the thoughtfully designed split floor plan ensures privacy for the primary suite, while elegant formal living and dining rooms create the perfect setting for entertaining. At the heart of the home, the chef’s kitchen boasts an island overlooking the inviting family room with custom built-in shelving. Enjoy the screened in lanai located off of the kitchen and family room with plenty of space for multiple seating areas. The versatile 5th bedroom currently serves as a sophisticated study. The private primary retreat features a spacious walk-in closet and a spa-inspired bath with double vanity, separate shower, and soaking tub. Updated secondary bathrooms add to the home’s refined appeal. Beyond the home, enjoy private neighborhood access to Lake Minnehaha—ideal for paddle boating, kayaking, or simply taking in golden-hour sunsets on the PRIVATE DOCK over the water. With Lake Minnehaha visible just across the street, the location is second to none. You’ll also appreciate being zoned for TOP RATED schools and just minutes from Maitland Blvd, I-4, 436, and the area’s best shopping, dining, parks, and recreation. An optional HOA adds flexibility to enjoy the community your way. $875,000 Pending

939 Versailles Circle Maitland, Florida

4 Beds 3 Baths 2,732 SqFt 0.29 Acres

Welcome Home to Your Private Lakeside Oasis! ? Step into the lifestyle you’ve been dreaming of! This stunning 4-bedroom, 2.5-bath single-family home perfectly blends modern updates with peaceful lakefront living. From the moment you arrive, you’ll feel the warmth and serenity that makes this home truly special. Imagine mornings with coffee on your back patio, watching graceful birds drift across the lake, and evenings with golden sunsets shimmering on the water. The sparkling swimming pool invites you to unwind, play, and make memories — all while enjoying unmatched privacy in your fully fenced backyard. Inside, you’ll find spacious, light-filled rooms designed for comfort and connection. Energy efficiency shines with paid-off solar panels, keeping your electric bills incredibly low — so you can enjoy your home without worrying about the cost of staying cool. And for the car enthusiast, hobbyist, or dreamer — the seller is offering an incredible $10,000 credit to help you create your ultimate garage or workshop space! Don’t miss this rare opportunity to live where tranquility meets modern living — a home that feels like a retreat, yet close to everything you need. $859,000 Active

2514 Tuscarora Trail Maitland, Florida

4 Beds 3 Baths 3,000 SqFt 0.43 Acres

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