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$700,000
4 Beds 2 Baths Dommerich SubDv. 32751 Zip Code
A midcentury modern influenced Florida ranch offers a special location just a block from the school with a walking path behind providing a unique lifestyle for this special home. Natural Coquina stone accents are the focal point of the exterior elevation with seamless windows that allow incredible light in and are in keeping with the architecture of the era. This four-bedroom, two-bath home was thoughtfully renovated with vintage polished terrazzo, ceramic tile and some vaulted ceilings creating a spacious layout for ease of living. Kitchen is renovated with clean lined shaker cabinets, subway tile back splash, floating shelves, stainless appliances and sliding barn door for pantry. Kitchen blends with living space which can serve as dining or formal living, function possibilities are endless. Family spaces open through clear glass doors to back patio making entertaining a breeze with plenty of room to add on or grow. The backyard and side yard are spacious and possibilities endless. The fourth bedroom or home office is separate and off the family room while other three bedrooms are banked down another hallway. Baths are fully updated with timeless appointments. A spacious laundry room for great organization, provides easy day-to-day function. Other system updates include 2025 Lenox air conditioning, roof 2020, insulated garage door, vinyl fencing, irrigation system, vaulted ceilings and more. In the heart of Dommerich, this location allows you to enjoy an easy distance to schools, the Quad and close to the boardwalk to Maitland Community Park. Maitland is full of life, home to terrific parks, fabulous restaurants, shopping, home to the Enzian Theatre, Lake Lily and more. This is a rare find.

814 N Thistle Lane, Maitland

$689,000
4 Beds 3 Baths Dommerich Hills 2 Nd Add SubDv. 32751 Zip Code
Priced below Appraised Value — and the seller is ready to move. This classic 4-bedroom, 2.5-bath Maitland pool home sits on a spacious quarter-to-half-acre lot with peaceful lake views and delivers 3,000 square feet of open, comfortable living. The updated kitchen and open floor plan make the interior as functional as it is inviting, but the real showstopper is outside — a sparkling pool (Resurface 2025) and generous outdoor living area with a lake backdrop that makes every evening feel like a retreat. The big-ticket items are already handled: 7-year roof, 7-year AC, updated plumbing, and a fully paid-off solar system that virtually eliminates your monthly electric bill — and under Florida law, it won't raise your property taxes. Zoned for top-rated schools and just minutes to Winter Park's dining, shopping, and culture. This is a home with more value than the price tag suggests. Motivated seller. Bring your

2514 Tuscarora Trail, Maitland

$2,150,000
5 Beds 5 Baths Hollieanna Shores 1st Add SubDv. 32751 Zip Code
Under contract-accepting backup offers. Under Construction. An elite expression of sophisticated design and elevated living, this remarkable residence offers a resort-style experience that stands apart in Maitland. This home is positioned on a sprawling corner lot and immediately captivates with a grand façade and undeniable curb appeal. From the moment you step inside, the experience is dramatic and refined. An impressive foyer sets the stage for the elegant interiors beyond, where high ceilings, natural light, and thoughtfully curated finishes create an atmosphere of sophistication and comfort. Designed for both effortless daily living and elevated entertaining, the open-concept layout flows beautifully from the expansive living room into the formal dining space, framed by a striking wall of oversized sliders that open up to the spacious backyard/pool area. The heart of the home is the show-stopping chef’s kitchen featuring stunning Chantilly quartz countertops, a full Thermador appliance suite, and an oversized walk-in pantry. The primary suite is designed to feel like a five-star retreat, featuring a spa-inspired bath offering a freestanding soaking tub, dual vanities, a glass-enclosed walk-in shower, and an expansive closet. Adding to the home’s rarity and versatility, the main level also features a true guest suite perfect for hosting in comfort, as well as a dedicated office. Outside, the backyard is the definition of resort-style living. The sparkling pool and spa anchor the space, surrounded by a generous covered lanai with a summer kitchen and abundant room for lounge seating and al fresco dining. And beyond the home itself, the lifestyle is exceptional. Residents of Hollieanna Shores enjoy access to a shared boat slip giving you access to the Winter Park Chain of Lakes, offering a level of exclusivity and lake-life convenience that takes this property to another level. All of this is just minutes from Maitland City Centre, beloved local parks, the iconic Enzian Theater, and the upscale dining, shopping, and charm of Park Avenue. This home redefines what luxury living looks like in Maitland, where location, design, and lifestyle come together in a home that feels truly unforgettable.

101 Whitecaps Circle, Maitland

$1,800,000
4 Beds 5 Baths Woodbridge SubDv. 32751 Zip Code
Pre-Construction. To be built. Come build your dream home on this exceptional homesite in the heart of Maitland. This stunning new construction single-family residence will feature 4 bedrooms, 4.5 bathrooms, and 3,567 square feet of thoughtfully designed living space across two stories, showcasing sleek modern finishes and open-concept living ideal for today’s lifestyle. Set on a 0.26-acre cleared lot surrounded by majestic oak trees, the home offers a rare sense of privacy and tranquility while still enjoying all the conveniences of city living. Designed for both comfort and entertaining, the home will include spacious living and dining areas, a gourmet kitchen, and generously sized bedrooms, plus a luxurious primary suite retreat. The outdoor space provides ample room to create your ideal backyard oasis, perfectly complementing the home’s modern design. Located less than a mile from Maitland Community Park, you’ll enjoy nearby sports courts, scenic trails, picnic pavilions, and playgrounds. Just a short walk away are Seminary Lake and the SunRail Maitland station, offering effortless access to recreation and commuting alike. This pre-construction opportunity is a rare chance to own a brand-new custom-style home in one of Maitland’s most desirable and well-connected neighborhoods.

1130 Mechanic Street, Maitland

$2,850,000
5 Beds 5 Baths Lake Maitland Owl Preserve SubDv. 32751 Zip Code
Nestled within the 9-acre Lake Maitland Owl Preserve, this striking contemporary residence—crafted by acclaimed green builder E2 Homes offers a rare blend of architectural distinction, privacy, and natural beauty. Surrounded by protected conservation land, the home delivers a serene retreat just minutes from the vibrant lifestyle of Winter Park. Designed by internationally recognized architect Jose Vengas, the home showcases dramatic ceiling heights, clean modern lines, and expansive glass walls that flood the interiors with natural light while blurring the line between indoor and outdoor living. The thoughtfully designed open-concept floor plan centers around a show-stopping chef’s kitchen featuring custom cabinetry, a statement marble backsplash, and a full suite of premium Sub-Zero and Wolf appliances perfect for both elevated entertaining and everyday living. Living and dining spaces flow effortlessly to a covered outdoor lounge with a fully equipped summer kitchen, overlooking a resort-style pool and spa designed for year-round enjoyment. Whether hosting guests or unwinding in private, this outdoor sanctuary is truly exceptional. All five bedrooms are generously sized private suites, each offering spa-inspired bathrooms with refined finishes and custom detailing. The primary suite is a true retreat, featuring a luxurious bath experience and expansive walk-in closets designed for both beauty and function. A first-floor owner’s suite provides exceptional flexibility for multi-generational living or guest accommodations, while the upper level reveals gallery-style walkways and an elegant terrace that highlights the home’s architectural artistry. With nearly 5,000 square feet of meticulously curated living space, this exceptional estate delivers modern sophistication in one of Central Florida’s most exclusive and private enclaves—just moments from Winter Park’s renowned dining, boutiques, and cultural destinations.

350 Northwind Road, Maitland

$815,000
4 Beds 3 Baths Lakewood Shores 1st Add SubDv. 32751 Zip Code
Welcome to 185 Birchwood Drive, a rare Maitland SKIABLE LAKEFRONT retreat offering the perfect combination of privacy, elevation, and effortless Florida luxury. Positioned high above the waterline with sweeping lake views, this property delivers true lake living without the typical flood insurance requirement. Inside, the home is bright and inviting with luxury vinyl plank flooring throughout and a functional layout designed for both everyday comfort and entertaining. The open-concept main living space is highlighted by vaulted ceilings and a dramatic wall of glass framing the water, flowing seamlessly into the kitchen with generous cabinetry, stainless appliances, and a large center island ideal for gathering. The home also features beautifully updated bathrooms, and a split floor plan that provides ideal separation for guests, a home office, or multi-generational living. Outdoors, enjoy a private waterfront oasis complete with a resort-style pool, expansive entertaining space, and fully fenced yard perfect for dogs, and a updated 2019 roof. And because the lake is private, you can enjoy boating without the hassle of registering your boat—a rare convenience for waterfront owners. Perfectly located near I-4 with express lane access, 17-92, and just minutes to Park Avenue / Winter Park, this home offers the lifestyle buyers want most: stunning views, privacy, convenience, and true lakefront enjoyment.

185 Birchwood Drive, Maitland

$1,199,500
5 Beds 4 Baths Wellington SubDv. 32751 Zip Code
Welcome home to one of the best-kept Maitland secrets, the neighborhood of Wellington. This lakefront home enjoys over 125 feet of linear frontage on Lake of Woods, a spring-fed skiable lake. Home is nearly 3,200 square feet, four bedrooms, three baths with incredible sunset views. Home is spacious with a first-floor primary suite and other bedrooms upstairs with generous flex space. Living space features a wood-burning fireplace with a vaulted ceiling and wood beam architectural accents. Two separate covered porches and screened pool make entertaining a breeze. Other features include solar power energy system (paid in full), newer roof, 2024 air conditioner, updated Hardie board siding, new windows, leaf guard gutter system, replumbed and more. This location is pristine close to many amenities and major roadways. This is a unique opportunity to enjoy lake life at its best.

1232 Wellington Terrace, Maitland

$717,000
4 Beds 2 Baths Dommerich/Maitland Highlands SubDv. 32751 Zip Code
Fantastic opportunity in a sought-after neighborhood near top-rated Dommerich Elementary and Maitland Middle schools. Located on a cul-de-sac, this 4 bedroom, 2 bath, 2,274 sq foot split plan home is walking distance to the schools. This well-maintained home is ready for your personal touch and offers solid bones, a functional floor plan and a .22-acre lot - perfect for buyers looking to renovate and create their dream home. With a large formal living room and dining room there is plenty of space for entertaining and family time. The galley kitchen has real wood cabinets, an eat-in space, and a breakfast bar. The updated primary bedroom has access to the screened patio and a spacious walk-in closet. The primary bath has dual sinks and a large walk-in shower. The 3 additional bedrooms are anchored by the secondary bath with a tub and dual sinks and functions as a pool bath too. Inside laundry with an adjoining storage room. Enjoy the back yard view of the mature landscaping and the sparkling pool from the comfort of the screened patio. A/C and hot water heater were replaced in February 2026. Roof was replaced in 2023. Located on a quiet street with sidewalks, nearby parks and easy access to shopping and dining. Welcome home!

761 Goldwater Court, Maitland

$1,100,000
4 Beds 4 Baths Lake Sybelia Cove Ph 01 SubDv. 32751 Zip Code
Nestled in the QUIET, oak tree lined and GATED community of LAKE SYBELIA COVE, this CUSTOM-built TUSCAN-style home offers a respite from the outside world and over 3,000 sq. ft of incredibly beautiful and tranquil living space along with the convenience of daily walks around Lake Sybelia. This IMMACULATE 4-bedroom, 3.5-bath residence features thoughtful design and QUALITY CRAFTSMANSHIP throughout. The GOURMET KITCHEN is equipped with custom cabinetry, granite countertops, an onyx backsplash, a GAS cooktop, and stainless steel appliances, including premium additions like a Viking FRENCH DOOR wall oven, Wolf steam oven, and Bosch dishwasher. On the main floor, the primary suite provides convenience and privacy, along with a second bedroom and full bath. Upstairs, two additional bedrooms each open to private BALCONIES—one offering an impressive VIEW of LAKE SYBELIA. Elegant tray ceilings with crown molding accent the living room, dining room, and primary bedroom. Marble tile flooring flow seamlessly throughout the home, complemented by red oak stairs with wrought iron railings and wide 7.5-inch baseboards. Built for comfort and efficiency, the home includes a RADIANT BARRIER for energy savings, foam-insulated masonry walls on the first floor for better insulation and sound reduction, a whole-house water filtration system, and a GAS water heater. Outdoor spaces include a screened back patio, updated balconies with new drains and flooring, front porch pavers, French drains, and gutters on both the front and back.Recent updates ensure the home is move-in ready. Here are a few of the most recent improvements. NEW tile roof (2023), Exterior painting (2023), Marble flooring installation (2023), Interior painting (2024), Upstairs and downstairs Carrier heat pump HVAC systems (2024 and 2025). Additional enhancements from prior years include CUSTOM front doors and Plantation Shutters on all windows. Located in an excellent school district and just 3 miles from the RDV Sportsplex, this home is conveniently close to the dining, shopping, and all the cultural amenities of MAITLAND and nearby WINTER PARK. Make sure to see the attached video and 3D VIRTUAL Walk Through.

890 Cranes Court, Maitland

$630,000
4 Beds 3 Baths Druid Isle SubDv. 32751 Zip Code
Nestled in the highly desirable Druid Isle neighborhood, this single-family residence offers the perfect blend of comfort, style, and waterfront living. Boasting 2,162 square feet of thoughtfully designed living space, this 4-bedroom, 3-bathroom home is ideal for both everyday living and entertaining. A welcoming layout and abundant natural light create a warm, inviting atmosphere throughout. Step outside to your own private oasis, where a sparkling pool overlooks serene lakefront views, providing a picturesque backdrop for relaxation and outdoor gatherings. Whether enjoying morning coffee by the water or hosting sunset get-togethers, the outdoor space is designed to make the most of Florida living. The peaceful lake setting adds a sense of privacy and tranquility rarely found so close to it all. Completing the home is a spacious 2-car garage and a prime location in one of the area’s most sought-after neighborhoods. Druid Isle is known for its charm, convenience, and strong sense of community, making this property an exceptional opportunity. This lakefront pool home truly offers the lifestyle you’ve been looking for—comfort, beauty, and an unbeatable location.

1301 Druid Isle Road, Maitland

$760,000
4 Beds 3 Baths Windsor Park SubDv. 32751 Zip Code
Welcome to 901 Camelot Road, a beautifully maintained residence in the heart of Dommerich. Across from the Quad, near the newly renovated Maitland Boardwalk that leads to Maitland Community Park, short distance to Dommerich Elementary and Maitland Middle, this home is ideal for families and individuals alike. This inviting home boasts a blend of modern amenities and classic charm, featuring four bedrooms, 2.5 baths and almost 2,400 square feet! Natural light draws you into the entry with views of the wooden ceiling beams in the living room and double French doors leading out to the backyard oasis. The centrally located kitchen features quartz countertops and stainless steel appliances, while making a seamless transition into the family room with a wood-burning fireplace. Updates throughout the home include 2023 HVAC, recessed lighting in various rooms with smart dimmer switches, 2024 fence, Nest thermostat, plantation shutters and indoor laundry room. The backyard has plenty of room to make your own, get creative and even add a spool or cocktail pool. This home is must-see. Contact me today to schedule a private showing.

901 Camelot Road, Maitland

$900,000
5 Beds 4 Baths Druid Hills SubDv. 32751 Zip Code
Tucked into prestigious Maitland Florida on coveted Druid Road, this one-of-a-kind residence offers the kind of flexibility—and lifestyle—that’s hard to find and even harder to forget. With 5 bedrooms and 4 full baths, this meticulously cared-for property is designed to fit real life beautifully: a 4-bedroom, 3-bath main home, plus a private 1-bedroom, 1-bath apartment with a brand-new kitchen and its own separate entrance—perfect for guests, multi-generational living, a home office suite, or income potential. Step inside and feel the difference immediately. Freshly painted and thoughtfully updated, the home shines with new flooring, new lighting with sleek LEDs, and a layout that gives everyone room to breathe. The heart of the home is the recently remodeled chef’s kitchen—a true culinary showpiece with high-end appliances, a large island, and modern finishes that make everyday meals and entertaining feel effortless. Beyond the primary living space, a versatile secondary living room invites you to create your ideal retreat—cozy lounge, media room, game room, or quiet escape. And the upgrades go well beyond what you can see: enjoy the peace of mind and efficiency of paid-off solar panels, plus two whole-home water filtration systems with reverse osmosis for crisp, clean water throughout. Outside, the magic continues. The home opens to a private backyard oasis where the sound of a waterfall sets the tone, koi fish glide below, and gatherings naturally gravitate to the outdoor kitchen—perfect for effortless entertaining. Then, tucked away in a second outdoor living space, you’ll find the ultimate wellness setup: a pergola, cold plunge, and sauna, and an outdoor shower creating a true healthy living retreat right in your own backyard. If you’ve been waiting for a home that feels special—updated, versatile, energy-smart, and built for both connection and calm—this Maitland gem is the one.

1619 Druid Road, Maitland

$1,025,000
4 Beds 4 Baths Dommerich Woods SubDv. 32751 Zip Code
On a quiet street in one of Maitland's desirable neighborhoods, this home blends timeless elegance with modern comfort. This stunning residence offers a combination of sophistication and functionality, making it the ideal place to call home. Boasting four bedrooms, 3.5 baths and plenty of flex space, this residence spans over 2,600 square feet and sits on a generous .33-acre lot. Natural light draws you into the entry with views of the backyard oasis. The abundance of outdoor living that includes a covered porch with vaulted ceilings, private pool, two separate sitting areas with composite decking and garden areas, provide the backdrop for hosting family and friends. The kitchen is outfitted with stainless appliances (2025), ample cabinetry, a large walk-in pantry and granite/butcher block countertops. This split plan offers three bedrooms and two baths on the second level, one bedroom is complete with an en-suite bath. The peaceful owner's retreat is on the lower ground floor and is completely private from the rest of the living areas. It features a flex space/office as you enter the primary bedroom with a set of solid double doors. Once inside, you will notice two walk-in closets, an en-suite bath with a jacuzzi tub and separate shower, along with a walkout to a private courtyard area. Updates include roof in 2025, exterior paint in 2025, new wood fence in 2024, one HVAC in 2024 and solid wood doors with Baldwin hardware. Other features of the home include optional access to the Lake Minnehaha boat ramp, which leads to the exclusive Chain of Lakes. With easy access to downtown Maitland, Interstate 4, Maitland Community Park, Dommerich Elementary and Maitland Middle Schools, this home is a must-see!

798 Sequoia Trail, Maitland

$230,000
2 Beds 2 Baths Ultra Vista Condo SubDv. 32751 Zip Code
One or more photo(s) has been virtually staged. This beautiful condo in the heart of Maitland—just minutes from Winter Park, Altamonte Springs, and more—truly has it all! Featuring new floors, a new roof, new windows, new HVAC, new plumbing, fresh interior and exterior paint, new fixtures, and new vanities, this home offers years of worry-free living with everything already taken care of. Outside, enjoy a private parking space, a crystal-blue community pool surrounded by stunning mature trees, and the most welcoming neighbors. Inside, you’ll love the soaring ceilings in the main living space filled with abundant natural light, plantation shutters throughout that elevate every room, beautifully remodeled bathrooms, and a shopper’s dream primary closet—fully walk-in and wraparound. The open living area leads to a screened patio, perfect for relaxing or entertaining, while the primary bedroom even has its own private patio. And you can cozy up by the wood-burning fireplace in the cooler months. With FHA and VA approval, along with conventional and cash options, this move-in-ready condo is accessible to a wide range of buyers. Schedule your private showing today and see for yourself what makes this home so special!

551 Finchley Road Unit 551, Maitland

$595,000
3 Beds 3 Baths Enclave/Maitland A-F SubDv. 32751 Zip Code
Beautiful move-in ready home in the highly sought-after gated community of Montacino, located in the heart of Maitland. This single-story Mediterranean inspired home boasts three spacious bedrooms, including the grand Primary bedroom suite with its private spa-inspired bathroom with a jacuzzi tub, another inviting full bathroom, a convenient half bath, and a separate office or den great for remote work or hobbies. The split plan allows for plenty of privacy and includes a formal dining room, a chef's kitchen with a spacious eat-in area overlooking the gorgeous family room with a gas-ready fireplace, which leads to the peaceful screened-in back porch. Elegant Tray ceilings, eight-foot doors, charming archways and recessed lighting add to the allure of this home. With an oversized two-car garage and a nicely appointed interior laundry room, this low-maintenance home offers plenty of storage, and carefree living. The affordable HOA fee provides privacy and security with the gated entrance, access to the sparkling community pool, professional maintenance of all the lush landscaping, and scenic paved paths overlooking tranquil Lake Charity. Don't miss your chance to live in this elegant community, which is zoned for top-rated schools, and is perfectly located near Interstate 4, the Maitland Town Center and popular downtown Winter Park. Schedule your private showing today!

1447 Caring Court, Maitland

$235,000
3 Beds 2 Baths Park Lake Villas Condo SubDv. 32751 Zip Code
Come to your new home centrally located between Downtown Maitland and Winter Park. Close to the conveniences of retail shopping, restaurants, the Sunrail Station and I-4 to get you around Central Florida quickly. Enter into your one story condo to an open living, dining and kitchen floorplan for lots of space and flexibility. Ceramic tile throughout, 5" base molding, 6 panel doors and updated hardware, energy efficient, double paned front windows (2018), granite counter tops in the kitchen with wood cabinets that have upper and under cabinet lighting (2017), pendant island lighting and a NEW stainless steel refrigerator. The kitchen peninsula provides extra seating for bar stool, causal eating. Hot water heater was changed to tankless (2018)to open up more space in the closet to use as a pantry. Enter the front bedroom that can also be used as an office through FRENCH DOORS. This room also has a large walk in closet for lots of storage. Down the hallway, there is an inside laundry closet with a NEW washer and dryer and a folding station for convenience. Both bathrooms were renovated with granite counters in 2017. Walk further down the hall to the two back bedrooms that each have their own sliding glass doors to the private back screened in porch with tile floors. Attic access in the hallway provides extra storage. Roof and exterior paint 2024, interior paint 2025, A/C 2020, plumbing 2018, electrical 2005.

613 Orange Tree Court Unit 507, Maitland

$1,798,999
5 Beds 5 Baths Hollieanna Shores SubDv. 32751 Zip Code
Under contract-accepting backup offers. Under Construction. A masterpiece of luxury design by LUIH Luxury Homes, perfectly positioned in the prestigious neighborhood of Hollieanna Shores. As you arrive, a striking façade with an elegant arched entryway sets an unforgettable tone. Beyond the front door, soaring ceilings and designer finishes frame an expansive living room where glass sliders dissolve the boundary between indoor and outdoor living, creating a seamless transition to the lanai and resort-style backyard. At the heart of the home, a chef’s kitchen designed for both performance and beauty exceeds every expectation. Sleek quartz countertops, a full Thermador appliance suite, custom cabinetry, and an oversized walk-in pantry elevate culinary experiences to a professional standard. The primary suite is a private sanctuary intentionally crafted to evoke a spa-like retreat. A stunning bathroom showcases a freestanding tub, an expansive walk-in shower, dual vanities, and exquisite finishes, while a large boutique-style closet with custom built-ins ensures every piece has its place. The upstairs level offers a generous loft and beautifully appointed secondary bedrooms, creating the ideal separation of space for family or guests. Outdoor living is nothing short of extraordinary, featuring a huge covered lanai with a full summer kitchen overlooking a shimmering pool and expansive, fully fenced backyard. Situated in the sought-after Hollieanna Shores neighborhood, this residence places you moments from Maitland City Centre, local parks, the iconic Enzian Theatre, and Park Ave. shopping and dining. If you’re seeking a home that feels both artful and effortless, this is where elevated living becomes reality.

105 Tangelo Court, Maitland

$820,000
4 Beds 2 Baths Highland Park Estates First Add SubDv. 32751 Zip Code
This beautifully updated 4-bedroom, 2-bath pool home offers 2,000 square feet of inviting living space on a spacious corner lot in highly desirable Maitland. The open living, kitchen, and dining area features a striking limestone fireplace, crown molding, custom built-ins, laminate wood flooring, and abundant natural light through French doors and skylights. The designer kitchen includes white and espresso cabinetry, white café appliances with antique brass accents, quartz countertops, a Venetian plaster–wrapped hood, a pot filler, a generous island with seating for four, and charming antique pantry doors. The primary suite offers a private retreat with direct access to the pool and a recently renovated ensuite bathroom with a quartz and wood vanity, a beautifully tiled shower with frameless glass doors, and dual shower heads. Additional interior highlights include a renovated hall bathroom, blinds and ceiling fans throughout, and a well-appointed laundry/mud room with floor-to-ceiling cabinetry offering tons of storage, a stainless sink, and included washer and dryer. The outdoor living space is exceptional! Start your day with a cup of coffee within the sanctuary of your ivy-lined courtyard with the serene sounds of the custom water feature. Finish the day with friends and family in your screened-in pool. Many other thoughtful outdoor details such as low-maintenance turf, paver walkway areas and front porch - perfect for relaxing, entertaining and enjoying year-round outdoor living. A side-entry two-car garage provides both convenience and curb appeal. Located within minutes of shopping, dining, and local parks, this home is zoned for top-rated schools including Dommerich Elementary, Maitland Middle, and Winter Park High School, and offers quick access to I-4, Maitland Community Park, and Lake Lily Park. This is the perfect blend of style, comfort, and unbeatable location. ROOF - 2025 HVAC - 2020 WATER HEATER - 2021 POOL HEATER & PUMP - 2023

2270 Deloraine Trail, Maitland

$835,000
4 Beds 2 Baths Maitland Grove SubDv. 32751 Zip Code
One or more photo(s) has been virtually staged. Stately brick home in a premier Maitland neighborhood—set beneath a canopy of mature oaks on a lush 1/3-acre lot, this 4-bedroom, 2-bathroom home offers just under 2,500 SF of timeless elegance and modern comfort. A covered front porch perfect for rocking chairs, brick-paver walkway, double entry doors, and side-entry garage create an inviting first impression. The open layout makes everyday living and entertaining effortless. The heart of the home is the remodeled kitchen, featuring a large floating island with seating, pendant lighting, custom cabinetry, granite countertops, stainless steel appliances—including a built-in oven and 6-burner propane cooktop—and a coffee/beverage bar. Sunlight pours through the home, illuminating engineered hardwood floors, crown molding, built-ins, and a stacked-stone wood-burning fireplace, all adding warmth and character. The split-floor plan offers privacy and functionality. The spacious primary suite provides a serene retreat with a remodeled bathroom featuring a seamless-glass walk-in shower, private water closet, marble countertops, custom cabinetry, and a jetted/heated tub with brand-new pump and heater (2025). Guest bedrooms are generously sized, including one with a huge walk-in closet providing ample storage, while the remodeled guest bath features dual sinks, granite countertops, and custom cabinetry, with direct pool access. An indoor laundry room adds convenience. Step outside to a private backyard oasis: a fully fenced paradise with a large saltwater pool, water feature, expansive brick-covered patio with bar, mini-fridge, hot/cold sink, stub-out for future grill, cypress tongue & groove ceilings, lighting, fans, and retractable screens. Enjoy an outdoor hot/cold shower, wood deck, gazebo, mature landscaping with avocado, lemon, and lime trees, two sheds, and an 8x12 greenhouse with power and irrigation. Meticulous care is evident with upgrades including a new roof with hurricane straps (2021), AC ductwork (2022), electrical panels (2023), on-demand tankless water heaters (<5 years), full spray-foam insulation, high-wind-rated double-pane windows, whole-house water softener (2025), and fresh exterior (2023) and interior paint (2025). Perfectly positioned across from Orangewood School (K–12) and minutes from Lake Sybelia Elementary, enjoy peaceful walks around the shores of Lake Sybelia, visit the lakeside park, or bike to Independence Lane and Lake Lily for farmers markets, dining, and community events. Quick access to I-4 keeps the city within reach while preserving the tranquility of a quiet, tree-lined enclave. A rare combination of style, upgrades, and lifestyle—this home is ready for your next chapter.

221 White Oak Circle, Maitland

$975,000
4 Beds 3 Baths Maitland Park South SubDv. 32751 Zip Code
One or more photo(s) has been virtually staged. Priced below appraised value for a limited opportunity to capture instant equity. Welcome to 1421 Sunnyside Drive, Maitland, FL, a beautifully maintained 4-bedroom, 2.5-bath single-family home with a pool, located on a corner lot directly adjacent to Winter Park. While this home carries a Maitland address, it sits just steps from Winter Park homes, offering the best of both locations. This move-in-ready residence features thoughtfully designed indoor and outdoor living spaces and is zoned for the top-rated Dommerich Elementary School. From the moment you arrive, manicured landscaping and an inviting covered front porch create a warm first impression. Inside, natural light fills the home through skylights and bay windows, highlighting hardwood floors and a wood-burning fireplace. The open layout provides a seamless flow between living spaces, ideal for everyday living and entertaining. The chef’s kitchen serves as the heart of the home and features custom hardwood cabinetry, granite countertops, stainless steel appliances, a wine chiller, and a spacious breakfast island with ample seating. The kitchen opens to the main living areas, creating a functional and welcoming space. The primary suite offers a private retreat with wood floors and French doors leading directly to the porch. The ensuite bathroom includes an oversized shower with spa-style jets and customized storage. Three additional bedrooms and a full bathroom are located down a terrazzo-finished hallway and include custom upgrades. The dining area captures beautiful morning light through the bay window, while the living room features French doors that open to the outdoor living space. The private backyard oasis is designed for year-round enjoyment and includes a heated pool enclosed by a full screened deck and patio, creating a true indoor-outdoor lifestyle. Additional features include a custom built-in home office with abundant storage, a freshly refinished two-car garage, and an oversized driveway with a 30-amp electrical hookup for an RV or boat. The home has been freshly painted inside and out, includes new carpet, and reflects quality craftsmanship throughout. Enjoy quick access to Winter Park’s shops, dining, parks, and cultural offerings, along with the conveniences of Maitland living, making this home an exceptional opportunity in a highly desirable Central Florida location.

1421 Sunnyside Drive, Maitland

$4,999,000
5 Beds 8 Baths Floridahaven SubDv. 32751 Zip Code
Pre-Construction. To be built. An extraordinary opportunity to claim one of Lake Seminary’s desired shorelines awaits. Masterfully envisioned by Heathrow Custom Homes, this newly built lakefront estate introduces a fresh standard of modern luxury for Maitland and Winter Park. Poised on an expansive 0.69-acre parcel, the residence spans nearly 6,500 square feet of impeccably curated living space, where sophisticated architecture and bespoke finishes harmonize with the tranquil beauty of the lake. A striking floating staircase framed by floor-to-ceiling glass offers a captivating first impression, while the grand entry reveals uninterrupted vistas of the pool terrace and shimmering water beyond. The chef’s kitchen, anchored by a remarkable 20-foot island, features premier appliances, exceptional storage and a concealed full-service scullery, creating an environment for hosting with grace and ease. The great room continues the home’s celebration of light and space with walls of glass that welcome breathtaking lake views at every turn. The primary suite is a serene retreat, showcasing a spa-inspired bath with floating vanities, a freestanding soaking tub, an expansive glass-enclosed shower and extravagant walk-in closets designed for the discerning owner. A secondary bedroom suite and oversized laundry enrich the main level, while an expansive lanai with an extraordinary summer kitchen invites effortless alfresco living, an experience only genuine lakefront living can provide. The second floor unfolds into a generous game room, complete with a wet bar and kitchenette. Three beautifully appointed bedroom suites, two scenic balconies, and a purpose-built home theater create an environment tailor-made for indulgence and entertainment. A new boathouse, soon to be constructed, further elevates the lakefront lifestyle. With three garages, a contemporary parking court, and meticulously executed architectural detail, this residence embodies modern luxury at its most refined. Lake Seminary, home to just 35 exclusive residences, offers coveted privacy while remaining moments from boutique shopping, celebrated dining and best of Winter Park. Immediate access to Interstate 4 and surrounding beltways ensures effortless connectivity throughout Central Florida.

360 Lake Seminary Circle, Maitland

$415,000
3 Beds 2 Baths Lake Eulalia Heights SubDv. 32751 Zip Code
Step into timeless style with this completely updated mid-century modern home tucked away on a quiet Maitland cul-de-sac. This 3-bedroom, 2-bath residence offers 1,521 sq ft of thoughtfully designed living space featuring refinished terrazzo floors, brand-new windows, and abundant natural light. The modern kitchen shines with new cabinets, stone countertops, and stainless-steel appliances, while both bathrooms have been beautifully remodeled with contemporary finishes. Fresh interior and exterior paint, new lighting and ceiling fans throughout, and lush new landscaping make this home truly move-in ready. Enjoy the best of Central Florida living—just steps from Maitland’s shops and restaurants and minutes from charming downtown Winter Park

6 Barnard Court, Maitland

$1,425,000
3 Beds 3 Baths Hollieanna Shores SubDv. 32751 Zip Code
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!

123 Hollie Court, Maitland

$575,000
4 Beds 3 Baths Stonewood SubDv. 32751 Zip Code
Nestled on a gorgeous tree-lined street, this charming residence exudes warmth, elegance, and timeless appeal. From the moment you arrive, the excellent curb appeal draws you in — with an established landscaped yard, paver driveway and walkways, classic brick exterior with shutters, and newer front and garage doors that set the tone for what awaits inside. Step into an inviting home where quality craftsmanship meets modern updates. The updated kitchen is a true showpiece, featuring granite countertops, solid wood cabinetry, tiled backsplash, breakfast bar with pendant lighting, and stainless steel appliances, including a Bosch dishwasher (2024) and a new double oven (2021). Throughout the main living areas, you’ll find gleaming hardwood floors and crown molding, enhancing the home’s sophisticated style. Large windows and solar tubes in the kitchen and family room fill the space with beautiful natural light. Enjoy two cozy wood-burning fireplaces — one in the family room and one in the living room — each flanked by built-in shelving and cabinetry. The living room’s large picturesque window offers the perfect spot for seasonal décor or simply enjoying the tranquil view. A separate dining room with built-in cabinets, crown molding, and sliders to the back porch makes entertaining effortless. The primary suite is spacious and serene, featuring a walk-in closet, crown molding, and a beautifully updated en suite bath with granite counters, tiled shower with glass enclosure, updated lighting and fixtures, and a new TOTO toilet. The three oversized secondary bedrooms offer ample closet space; one is currently used as an office. The updated guest bath includes granite countertops and modern finishes. The large inside laundry room, conveniently located off the kitchen, provides abundant cabinet and counter space, a utility sink, and two pantries, plus a private half bath with a new high-rise toilet for guests. Step into the tiled Florida room, where large windows and motorized retractable screens invite you to relax and enjoy the gorgeous, manicured backyard views. Off the Florida room, a brick porch with a retractable awning and coach lights provides a peaceful spot for morning coffee or evening gatherings. The fenced backyard features a paver-lined walkway and lush landscaping for added privacy and charm. Recent updates include: HVAC (2023) • Whole House Water Softener (2021) • Washer (2023) • Dryer (2019) • Water Heater (2021) • Porch Awning (2016) • Range (2021) • Refrigerator (2016) • Bosch Dishwasher (2024) • Roof (2013) replumbed (2002) Located near Maitland Avenue, I-4, and 414, this home offers easy access to dining, shopping, parks, the Maitland Farmers Market, and top-rated schools. Come see why homes in Stonewood are so highly sought-after — this one truly has it all: charm, comfort, and convenience in one of Maitland’s most picturesque neighborhoods.

448 Plumhollow Lane, Maitland

$221,000
2 Beds 2 Baths Park Lake Townhouses SubDv. 32751 Zip Code
Incredible location! This beautifully updated 2 bedroom, 1.5 bath condo in Maitland is located minutes from shops, restaurants and offers easy access to I-4!. New windows! New electrical panels 2026, New water heater 2026. The stylish kitchen features granite countertops, 42 inch cabinetry, built-in wine glass rack, stainless appliances, pass thru window, and a long breakfast bar. Updated half bath downstairs for convenience. Both spacious bedrooms are located upstairs and share an updated bath with a glass enclosed tiled shower with rain shower fixtures. Laminate wood and tile flooring throughout! No carpet! Indoor laundry room with lots of storage with Maytag appliances. French doors lead you to a private fenced patio and one car garage! Step right outside the front door to the sparkling pool! Security system included. Zoned for sought-after schools, Dommerich Elementary, Maitland Middle, and Winter Park High. The neighborhood features a community pool, dock on Lake Gem and gorgeous landscaping and trees.

1009 Grove St Unit 1009, Maitland

$613,000
2 Beds 2 Baths Moorings On Lake Maitland Condo SubDv. 32751 Zip Code
Elegant lakefront on the shores of Lake Maitland! Experience timeless refinement in this exquisitely renovated lakefront condominium, where bespoke craftmanship meets modern luxury. Every detail has been thoughtfully curated - from the custom millworker and intricate moldings to the tailored built-ins that evoke charm of a grand London flat. Light filled living spaces open to serene lake views, creating an atmosphere of both grace and tranquility. The gourmet kitchen is a study in elegance and function, featuring hand finished cabinetry, premium appliances, and stone surfaces. Gracious living room flows seamlessly into a charming sunroom, featuring French doors and classic brick flooring. The primary suite offers a peaceful, retreat with lake views, spa-inspired finishes and impeccable attention to detail. With rich textures, layered lighting, and designer finishes throughout, this home balances sophistication and warmth in perfect measure. Located in an exclusive building with exceptional amenities including pool, spa, clubhouse, a BOAT SLIP and 1 covered carport space. This residence embodies elevated lakefront living, with distinctive character. Call today for your private viewing of this exquisite condo. Please note there is a $640 transfer fee for boat slip paid at closing by Buyer.

204 Quayside Circle Unit 202, Maitland

$228,000
2 Beds 2 Baths Park Lake Villas Condo SubDv. 32751 Zip Code
One or more photo(s) has been virtually staged. **2024 ROOF, 2025 HVAC** FULLY RENOVATED TOP TO BOTTOM. Discover this stunning, newly renovated one story end unit boasting over 1,000 sq ft of modern living space. This spacious 2 bedroom, 2 bath condo features luxury vinyl plank flooring throughout, a stylish new kitchen with white shaker cabinets, quartz countertops, and stainless steel appliances, plus all new light fixtures and fresh interior and exterior paint. Both bathrooms have been tastefully updated, including a stand up shower with designer finishes. Additional upgrades include a newer water heater, 2024 exterior paint, new attic insulation and more. Enjoy outdoor living on the private fenced patio, perfect for relaxing or entertaining. With the HOA maintaining the exterior, roof, and landscaping, you’ll enjoy truly worry free living. Conveniently located just steps from the community pool and minutes from shopping, dining, the Maitland Farmers Market, SunRail, Park Avenue, Winter Park Village, and I4. Schedule your showing today!

1601 Grove Street Unit 552, Maitland

$770,000
4 Beds 5 Baths Oakleigh 3rd Add SubDv. 32751 Zip Code
In the Heart of Maitland Winter Park boundary ~ 0.36 Acre Pool Home ~ 4200 Square Foot ~ 4 Bedrooms ~ 5 Bathrooms ~ Pool Home **For those with vision!** This rare opportunity in Maitland’s coveted Oakleigh neighborhood offers the ideal canvas for renovation or redesign. Surrounded by lakefront estates on an oversized lot, this expansive 4,200 sq ft traditional ranch sits on over one-third of an acre and is filled with natural light. The great room overlooks a private outdoor oasis with a pool, mature landscaping, and a brick-paved patio—perfect for entertaining. The chef’s kitchen features a commercial gas range, double ovens, built-in refrigerator, and a cozy dinette with a wood-burning fireplace—ready for your modern touch. A flexible double-primary split floor plan includes 4 bedrooms, 5 baths, and multiple living spaces, offering endless potential for customization. The primary suite showcases wood beams, hardwood floors, and a sitting area with pool views. The spacious en-suite includes dual showers, walk-in closets, and a skylit garden tub awaiting your personal style. Just minutes from Downtown Maitland, Minnehaha Park, and Lake Maitland, with easy I-4 access, this property offers both prime location and unmatched potential. Whether you’re an investor, designer, or homeowner ready to create your dream home, **51 Oakleigh Lane** is ready to become a masterpiece.

51 Oakleigh Lane, Maitland

$500,000
4 Beds 2 Baths Indian Hills Unit 1 Rep SubDv. 32751 Zip Code
**2025 ROOF** | **POOL HOME** Start your new life to one of Orlando's most prestigious suburbs! Located in the heart of Maitland and zoned for great schools! This 4 bedroom, 2 bath home is a sanctuary for a growing family or to start yours. In this stunning home comfort meets timeless charm. Outside you will find a Zen-like screened pool area and a serene back yard lushly landscaped with mature fruit trees. Enjoy the benefits of a newly installed roof and upgraded insulation, providing energy efficiency and cost savings. This home offers the perfect blend of value and comfort, situated minutes from downtown Winter Park, downtown Orlando and just walking distance from Kewanee Park. Here you’ll enjoy proximity to upscale boutiques, cafés and fine dining, making this home convenient and comfortable for everyday living. This is a rare opportunity to own a meticulously maintained and perfectly situated home. Ready for you to move in and enjoy!

2632 Derbyshire Road, Maitland

$375,000
3 Beds 3 Baths Ultra Vista Condo SubDv. 32751 Zip Code
Stunning, renovated condo in Maitland’s Ultra Vista community with attached one-car garage. Expect to be impressed as you enter this luxury residence boasting vaulted ceilings which fill the home with natural light! Fall in love with this remodeled kitchen with a butcher block island, 42-inch white cabinetry, soft-close drawers, pantry, tile flooring, and stainless-steel appliances. Wonderful great room with wood-burning fireplace, dining room, and sliding doors leading to the enclosed outdoor porch, perfect for entertaining! Gorgeous wood flooring brings warmth to the home. Retreat to the primary suite with an impressive, updated bath featuring stone counters, walk-in closet, and spacious walk-in shower. The 2nd bedroom is bright and spacious with an updated en-suite bath with soaking tub. The downstairs bedroom with updated en-suite bath is perfectly positioned for a guest suite, home office or den. Enjoy the privacy outdoors with the stone patio and beautiful landscaping overlooking a conservation area. Updates include a new roof (2024), new electrical panel (2024), replumbed, AC (2016) and new exterior paint coming soon. This private community offers a sparkling swimming pool and dog park for its residence. Incredible location, minutes to Winter Park’s Park Ave for shopping and dining. This is the one you have been waiting for!

1990 Kenaston Road Unit 1990, Maitland