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$243,000
3 Beds ⋅ 3 Baths ⋅ Park Lake Twnhs Ph 02 SubDv. ⋅ 32751 Zip Code
Experience lakeside living in this elegant 3-bed, 3-bath townhome in the heart of Maitland! This 1,575 sq ft residence offers refined, comfortable living with tranquil lake views. The townhome features two upstairs ensuite bedrooms—one with a private balcony overlooking the lake, a perfect spot to enjoy your morning coffee—and a convenient first-floor bedroom that provides space and ease. Enjoy a large patio ideal for entertaining, plus community amenities including a pool and park. Prime Maitland location near Maitland City Centre, SunRail, I-4, and upscale dining and shops. Currently leased through 2/2026, this serene lakeside townhome offers the rare flexibility of a strong investment today and a sophisticated primary home tomorrow. Experience the beauty and convenience of Maitland living—book your private tour today!

806 Town Circle Unit 156, Maitland
$350,000
3 Beds ⋅ 2 Baths ⋅ Hamlet At Maitland SubDv. ⋅ 32751 Zip Code
This charming 3-bedroom, 2-bathroom single-family home with the best of Florida living. Located in the north of Orlando (Maitland - Winter Park area). 1.3 miles to the Center of Winter Park Shopping Plaza (Office Depot, UPS, Ross, Marshalls, Home Goods, Five Below, LA Fitness, Petco and Michaels, Whole Foods Markets, and Banking). Access to major highways, minutes to downtown, and Orlando's world-renowned theme parks. This 1,146 square foot home features an open-concept floor plan. Primary suite includes a walk-in closet and a private suite bathroom, plus two additional bedrooms that provide flexibility for guests, family or a home office. 1 car garage with a large driveway that accommodates 2 more cars. The property's best feature is solar panels owned outright! With an average monthly bill of $35.00!!! Don't miss your chance to make it yours - schedule a private showing today!

1033 Hamlet Drive, Maitland
$279,000
3 Beds ⋅ 3 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code
Welcome to 920 Park Lake Circle in charming Maitland, FL — a beautifully updated 3 bedroom, 2 bath condo offering style, warmth, and unbeatable location. Step into a bright, open living space with an upgraded kitchen featuring shaker cabinetry, quartz countertops, stainless steel appliances, and designer lighting. Wood laminate flooring runs throughout all living areas, with the exception of the stairs, offering a clean and low maintenance feel. This peaceful lakefront community offers a sparkling pool and private lake access, perfect for Florida weekends. HOA covers all exterior maintenance, so you will never need to worry about lawn care or tree work. The garage door has also been recently replaced, offering added convenience and curb appeal. You’re just minutes from Maitland Community Park, with scenic walking trails, tennis courts, and playgrounds. Explore the nearby Art and History Museums Maitland, local cafés, boutiques, and downtown Maitland’s farmers market. Zoned for top rated Domerich Elementary and Maitland Middle School, and just a short drive to Winter Park and downtown Orlando, this condo blends lifestyle and location like few others.

920 Park Lake Circle Unit 36, Maitland
$571,000
3 Beds ⋅ 4 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code
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1240 Trust Lane, Maitland
$225,000
3 Beds ⋅ 3 Baths ⋅ Visconti East SubDv. ⋅ 32751 Zip Code
One or more photo(s) has been virtually staged. Welcome home to 1514 Legacy Club Drive, nestled in the highly sought-after Visconti East community. Live the true Florida lifestyle in this resort-style, gated neighborhood where affordable and quality living are still a reality. This stunning three-story condo with attached 2 car garage home has just been enhanced with a freshly painted interior and a brand-new tile roof currently being installed, hot water heater was replaced in 2025, and the AC replaced in 2018. The property is a perfect blend of style, comfort, and peace of mind. As you arrive, you’ll be greeted by a spacious two-car garage on the first floor, providing ample room for parking and storage. The second floor opens to a bright and airy open-concept living area, ideal for relaxing or entertaining. The well-appointed kitchen includes a full appliance package, and a convenient closet pantry for additional storage. Adjacent to the kitchen is a versatile third bedroom that can easily serve as a private den or home office, along with a half bath for guests. On the third floor, you’ll find two generous bedrooms, two full bathrooms, and a conveniently located laundry closet. Gated Visconti East community offers an impressive array of resort-style amenities, including two sparkling pools, a dock and gazebo overlooking beautiful Lake Shadow, a 24-hour fitness center, a playground, tennis, pickleball and basketball courts. Whether you prefer an active lifestyle or simply want to unwind in a peaceful setting, this community has it all. Water, sewer, pest control, and valet trash services are included in your HOA dues. Ideally located just 15 minutes from downtown Winter Park and downtown Orlando, and only about 30 minutes from the world-famous theme parks, this home provides unbeatable convenience. It’s close to the RDV Sportsplex, and the Maitland Exchange business center, and top rated schools—making it an excellent choice for both professionals and families. Easy access to I-4 and the 414/429 expressways ensures seamless commuting and travel. With excellent rental potential and a minimum one-year lease, this townhome is not only a wonderful place to live but also a smart investment opportunity. Don’t miss your chance to make this beautiful home yours—schedule your showing today before it’s gone!

1514 Legacy Club Drive Unit 1514, Maitland
$159,000
2 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code
Welcome to Lake Maitland Terrace, a charming lakeside community of Mid-Century Miami Modern condos set within eleven cottage-style buildings along the shores of Lake Maitland. Residents enjoy resort-style amenities, including a recently renovated lakeside pool, fishing dock, putting green, shuffleboard courts, and a clubhouse with kitchen. This first-floor, two-bedroom, one-bath condo in the Arlington Building has been maintained by the same owner for nearly 30 years. Updates include a 2021 AC, 4-year-old water heater, newer windows and front door, and a new roof (2023–2024). The open great room flows into the dining area, and the adjacent kitchen features a 2nd entrance. Much of the interior remains in original condition, and the old carpet has been removed, providing an ideal opportunity for a new owner to update and make it their own.  Additional features include one designated parking space, ample guest parking, enclosed bicycle storage, convenient laundry facilities, and racks for kayaks and paddleboards. The location is unbeatable—walk to the Enzian Theater and Lake Lily, or drive just five minutes to downtown Winter Park with easy access to I-4. Condo is being sold AS IS.

1140 S Orlando Avenue Unit A5, Maitland
$540,000
2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo Bldg 03 SubDv. ⋅ 32751 Zip Code
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.

206 Quayside Circle Unit 404, 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
$490,000
3 Beds ⋅ 2 Baths ⋅ Maitland Club SubDv. ⋅ 32751 Zip Code
Special Opportunity in the heart of Maitland! Own a piece of history or build your dream home on this generous quarter acre lot that is just a five-minute walk from the Maitland Arts Center. The existing 3-bedroom, 2 bath home has all the character of a historical home, including gorgeous 6-panel doors, unique floor plan, and built-in details. Relish the extensive mature landscaping and block workshop with electric and water. With Lake Sybella within a minute walk from the doorstep, you'll never want for natural beauty. You'll also have all the conveniences that come with living in the heart of Maitland.

400 Boynton Road, Maitland
$330,000
2 Beds ⋅ 1 Baths ⋅ Greenwood Gardens Rep SubDv. ⋅ 32751 Zip Code
COZY, 2 bedroom, 1 bath, 1 car garage home with a HUGE lot in a central location is ready for its new owners! As you enter, you will notice the OPEN living room and kitchen. The kitchen has custom wood cabinets, tile counters and backsplash. A large breakfast bar and eat-in nook area for your comfort. The bathroom is modern and sleek. Outside in the backyard, your OASIS awaits! There are fruit trees, areas for relaxing and a shed for storage. This home is in a NO HORN area of the railroad tracks that service the Sunrail and Amtrak. The Sunrail Station is within walking distance to the home for an easy work commute. NEWER ROOF, NEWER WINDOWS, updated electrical panel, tankless water heater, GAS stove, surround sound throughout as well. NO HOA. 30 minutes to downtown Orlando, 15 minutes to I-4 interstate and 5 minutes to 17-92. Whether you are looking for a great starter home, investment property or want to start from scratch and build your dream home, this one could be yours!!

735 Gamewell Avenue, 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
$385,000
3 Beds ⋅ 2 Baths ⋅ Druid Hills Park SubDv. ⋅ 32751 Zip Code
Experience Modern Florida Living at Its Finest Step inside this fully remodeled 3-bedroom, 2-bathroom residence and discover a seamless blend of sophistication, comfort, and everyday functionality. With a spacious 2-car garage, a welcoming front porch, and a large screened-in patio, this home offers the ideal balance of indoor elegance and outdoor tranquility. From the moment you enter, natural light fills the open-concept living and dining areas, highlighting the exquisite craftsmanship and premium finishes throughout. The gourmet chef’s kitchen is the true centerpiece — boasting custom cabinetry, sleek quartz countertops, a designer tile backsplash, and top-of-the-line stainless steel appliances. Whether you’re preparing weekday meals or hosting a dinner party, this kitchen delivers style and performance in perfect harmony. The home’s layout is thoughtfully designed for both comfort and connection. The living spaces flow effortlessly toward the screened-in patio, creating an inviting atmosphere for entertaining, relaxing, or enjoying quiet evenings in your own private retreat. Each of the two spa-inspired bathrooms has been completely transformed with luxury tile, contemporary vanities, and premium fixtures — evoking the serenity of a high-end resort. The primary suite serves as a peaceful haven, featuring generous space, soft natural light, and a modern ensuite designed for relaxation and rejuvenation. Step outside and enjoy the Florida lifestyle from your oversized screened patio, ideal for morning coffee, weekend gatherings, or simply unwinding under the stars. The 2-car garage provides plenty of room for vehicles and storage, adding convenience to your daily routine. Perfectly situated with easy access to major highways, this home offers unbeatable proximity to fine dining, upscale shopping, and world-famous theme parks. Whether you’re commuting, exploring, or entertaining, you’ll find yourself at the center of it all — without sacrificing peace and privacy at home. Every element of this remodel has been thoughtfully chosen to create a residence that feels brand new, yet instantly welcoming. From the modern finishes to the open layout and outdoor living space, this property captures the essence of effortless Florida living. Come experience the perfect combination of design, comfort, and location — and fall in love with the home you’ve been waiting for.

314 Banyan Drive, 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
$350,000
3 Beds ⋅ 2 Baths ⋅ Druid Hills Park SubDv. ⋅ 32751 Zip Code
One or more photo(s) has been virtually staged. GREAT OPPORTUNITY FOR FIRST TIME HOMEBUYERS AND INVESTORS TO TAKE ADVANTAGE OF THIS BELOW MEDIAN PRICE, $420,000 FOR SINGLE FAMILY AS OF MAY 2025, PROPERTY IN SOUGHT AFTER MAITLAND COMMUNITY OF DRUID HILLS. THIS PROPERTY BOASTS 3 BEDROOMS AND 2 BATHROOMS WITH A 2 CAR GARAGE NOT TO MENTION A DRIVEWAY FOR 4 OTHER CARS. ROOF IS NEW AS OF 2022, COMPLETE HVAC SYSTEM AIR HANDLER AND COMPRESSOR NEW AS OF 2023, CROWN MOLDING THRU OUT, SPACIOUS LOT WITH MATURE LANDSCAPING, RECENTLY REPLACED SEPTIC TANK PLUMBING PIPE, AND MORE. THIS PROPERTY IS CLOSE TO EVERYTHING. DOWNTOWN MAITLAND, WINTER PARK, AND ORLANDO JUST MINUTES AWAY. GREAT ACCESS TO I4 & THE 414. ORANGEWOOD CHRISTIAN SCHOOL JUST A FEW BLOCKS AWAY AND ALTAMONTE MALL JUST DOWN THE STREET. THIS WOULD BE A FANTASTIC STARTER HOME TO BEGIN TO BUILD A REAL ESTATE PORTFOLIO.

363 Croton Drive, Maitland
$335,000
2 Beds ⋅ 2 Baths ⋅ Sierra Condominiums SubDv. ⋅ 32751 Zip Code
Price improved! CONDO WITH PRIVATE GARAGE - JUST REPLUMBED WITH WARRANTY! Discover the perfect blend of comfort, elegance, and convenience in this beautifully updated 2-bedroom, 2-bath condominium in the highly sought-after Sierra Condominiums of Maitland. This move-in ready condo welcomes you with a screened front porch and an inviting living room with a wood-burning fireplace with an electric insert. The bonus room can be used as a television room, as a Florida room (offering a sunny spot to enjoy morning coffee while watching butterflies in the garden), or as a hobby room; leaving the living room free for formal entertaining. The upgraded kitchen features quartz countertops, under-cabinet lighting, new appliances, and accessible cupboards for easy access. A versatile breakfast nook (which is currently used as an office), includes a beautiful built-in cabinet perfect for dishes, collectibles or files. Tile floors in the kitchen and baths complement attractive laminate flooring throughout the living areas. Double-pane windows with plantation shutters, a new front door, gas heat, and a gas water heater provide comfort and efficiency year-round. Surrounded by mature trees and lush landscaping, this friendly, walkable neighborhood (with no traffic going through it), offers a warm community feel. Sierra residents enjoy a sparkling pool, tennis/pickleball court, and a welcoming clubhouse. HOA fees cover exterior maintenance, reserves for roofs, painting, roadway and pool upkeep, lawn care and cable television. A wonderful opportunity for those looking to downsize while maintaining an independent lifestyle – or an ideal first home with a coveted Maitland location!

2344 Sierra Lane, Maitland
$583,900
3 Beds ⋅ 2 Baths ⋅ Brittany Gardens SubDv. ⋅ 32751 Zip Code
Welcome to this beautifully appointed single-story, single-family home located in one of Maitland’s most exclusive gated communities. Nestled on the tranquil shores of Howell Creek and overlooking protected conservation land in the front, this residence offers a rare combination of privacy, natural beauty, and refined living. Step inside to an open and airy layout filled with natural light and serene water views. This residence features a split floor plan with 3 Bedrooms and 2 Full Bathrooms. The Floor Plan includes a Foyer, Formal Dining room with architectural designs, spacious living room with a gas fireplace, Open concept kitchen with generous cabinetry and countertop space, and a cozy dinette. The living spaces are thoughtfully designed for both relaxation and entertaining, featuring new vinyl plank flooring throughout the home. The primary suite offers a tranquil retreat with its own en-suite bath, while the additional bedrooms are ideal for family, guests, or a home office. Enjoy the outdoors in your private backyard oasis, where mature landscaping and direct frontage to Howell Creek create a serene setting for morning coffee or evening sunsets on the tiled screened porch or extended tile patio. The gated community provides added security all within a quiet, well-maintained environment. Just minutes to Park Avenue in Winter Park, Maitland Social, City Centre and Lake Lilly where you can enjoy Local Dining, Kelly's Ice Cream, Boutique Shopping, Farmer's Markets and Parks. Interlachen Country Club, The Racquet Club, WP9 are easily accessible. I-4, 417, Maitland Exchange and all the daily living needs such as Publix, Walgreens and CVS are within reach. Brittany Gardens Residents enjoy beautiful Common Areas that include Access to Howell Creek from the shore for fishing or non motor boat adventures and Brittany Park.

2634 Ultra Vista Drive, Maitland
$675,000
3 Beds ⋅ 2 Baths ⋅ Dixie Terrace SubDv. ⋅ 32751 Zip Code
Welcome to 1655 Sunnyside Drive, a beautifully charming home nestled on a picturesque corner lot in the heart of Maitland. Set on classic brick-lined roads, this 3-bedroom, 2-bathroom residence offers 1,418 square feet of thoughtfully designed living space filled with character and warmth. From the moment you arrive, you'll notice the inviting curb appeal, mature landscaping, and the undeniable charm that sets this home apart from the rest. Inside, the home exudes personality with unique architectural touches, cozy living spaces, and abundant natural light throughout. The well-appointed kitchen flows effortlessly into the main living area, making it perfect for both relaxing and entertaining. Each bedroom is spacious and comfortable, while the bathrooms offer tasteful finishes. Whether you're sipping coffee on the front porch or enjoying the peaceful surroundings, you'll feel right at home in this special space. Situated just minutes from the vibrant shops and restaurants of Park Avenue, this home also features two separate driveways, offering plenty of parking for guests or multiple vehicles—a rare find in this area. With its unbeatable location, timeless charm, and practical layout, 1655 Sunnyside Drive is the perfect blend of convenience and character. Don’t miss your opportunity to own a true gem in one of Maitland’s most desirable neighborhoods. ROOF: 2021 PLUMBING: 2021 AC: 2021 ELECTRICAL: 2021

1655 Sunnyside Drive, Maitland
$600,000
Hollieanna Shores SubDv. ⋅ 32751 Zip Code
Perfect opportunity to make this your dream home or add to your investment portfolio. This home is located on a 8x100 lot in the heart of Maitland and is walking to distance to Dommerich Elementary and Maitland Middle schools. This property provides loads of potential and offers a fenced backyard and a 2-car garage. Set up your showing today.

107 Tangelo Court, Maitland
$600,000
3 Beds ⋅ 3 Baths ⋅ Hollieanna Shores SubDv. ⋅ 32751 Zip Code
Perfect opportunity to make this your dream home or add to your investment portfolio. This home is located on an 80x100 lot in the heart of Maitland and is walking to distance to Dommerich Elementary and Maitland Middle schools. This property provides loads of potential and offers a fenced backyard and a 2-car garage. Set up your showing today.

107 Tangelo Court, Maitland
$575,000
4 Beds ⋅ 2 Baths ⋅ Forest Brook 3rd Sec SubDv. ⋅ 32751 Zip Code
Experience refined living in this impeccably maintained 4Bd/2Ba pool home with a spacious layout, perfectly situated in a desirable, well-established neighborhood close to shopping, dining and everyday essentials. The customized kitchen is a true showpiece—featuring an expansive pull-out pantry, double pull-out corner cabinet system, built-in spice rack, and a spacious island designed for both function and elegance. Abundant natural light, updated flush mount lighting, and ample storage create a space that is as beautiful as it is practical. Throughout the home, you’ll find timeless finishes including crown molding, wood-look porcelain tile, and double-pane windows that enhance both style and comfort. Step outside to your private oasis—an extra-large refinished pool (2017) surrounded by premier artificial turf and lush landscaping offering the perfect balance of luxury and low maintenance. The oversized garage impresses with extra shelving, an insulated door with DC quiet opener and battery backup, and the refrigerator is included. Peace of mind comes with thoughtful updates: Roof (2021), HVAC (2016), and new ductwork, R30 insulation and aluminum soffits (2024). A home where craftsmanship meets comfort—modern sophistication and meticulous care make this a rare opportunity not to be missed. CALL TODAY to schedule your private viewing.

671 Brookside Road, Maitland
$571,430
3 Beds ⋅ 2 Baths ⋅ Indian Hills Unit 9 SubDv. ⋅ 32751 Zip Code
RENOVATIONS OF THE HIGHEST STANDARD!! Sunshine State Home’s experienced design team continues to exceed the expectations of today’s discerning Buyer’s. The renovation of this classic Mid-Century Maitland home brings delightful charm within a highly sought after NON-HOA neighborhood of Indian Hills. The finished product “punches above it’s weight” in every possible way. KITCHEN offers two-tone, solid wood cabinetry topped with contemporary quartz counters. Stylish finishes including an undermount sink with long-neck faucet, upgraded black-matte cabinet door pulls and a modern stainless steel appliance package create a delightful cooking environment. LARGE LIVING SPACES including living / bonus / dinette and separate family rooms offer an abundance of options catering to a variety of lifestyle preferences and activities. BEDROOMS within this split-plan layout include His/Hers closets in the primary suite and a large 2nd bedroom and 3rd bedroom situated privately in the far corner of home. FLOORING throughout the home, upgraded Luxury Vinyl Plank was laid “wall-to-wall” and topped with upgraded 5 ¼“ baseboards, creating a peaceful yet contemporary feel to every room. BATHROOMS (both primary and secondary) have been fully remodeled including sinks, faucets, shower, tub, toilets, lighting and more. FINISHES including modern door hardware & hinges, ceiling fan and LED lighting throughout, wire rack shelving in all closets, updated electrical outlets and switches all combine to bring this vintage home up to today’s look & feel. OUTSIDE, a covered area on the back patio lanai provides the perfect shaded gathering place amidst a sun-filled day splashing in the inground swimming pool. Fully fenced and private, the backyard offers an oasis for sunbathing and a midnight swim. 4-POINT inspection items including roof (2023), hot-water heater (2025), HVAC (2019) will provide peace of mind. COMMUNITY events and activities abound within Indian Hills. Kewannee Park, a county park, offers walking trails and a boardwalk, fishing ponds, basketball court, and playgrounds all within walking distance. A-Rated Seminole County Public School district.

2666 Derbyshire Road, Maitland
$779,500
3 Beds ⋅ 2 Baths ⋅ Dommerich Estates 1st Add SubDv. ⋅ 32751 Zip Code
Welcome to this charming, move-in ready home nestled in the desirable, family-friendly Dommerich neighborhood. Featuring 3 bedrooms, 2 full bathrooms, and an open-concept living area filled with natural light, this home has the perfect blend of comfort and style. Featuring 2 additional dedicated office rooms, ideal for remote work or creative space, this home is ideal for modern living. The updated kitchen boasts stainless steel appliances, marble countertops, and ample cabinet space. Step into an open, light-filled interior with brand new flooring throughout and breathtaking floor-to-ceiling windows that has panoramic views of the sparkling saltwater pool. In the cooler months enjoy your own wood burning fireplace. Outside, enjoy a spacious paver driveway, a large 2-car garage, and a private backyard oasis. Major upgrades include a brand new roof (2025), ensuring peace of mind for years to come. Additional upgrades include recessed lighting, new flooring throughout, marble bathroom tiling, energy-efficient windows, new paver driveway and fresh interior/exterior paint. Enjoy private boat ramp access to the Winter Park Chain of Lakes. Zoned for A-rated Dommerich Elementary, Maitland Middle School and Winter Park High School. Walking distance to the Maitland Community Park, Maitland Social and the Maitland City Center. Minutes from Winter Park’s Park Avenue, known for its exquisite shopping and dining. Don’t miss out on this opportunity!

421 Arapaho Trail, Maitland
$680,000
3 Beds ⋅ 4 Baths ⋅ Orangedale Park SubDv. ⋅ 32751 Zip Code
HUGE Price Reduction!! There is simply nothing that compares to this deal! This exquisite attached single family home blends contemporary elegance with unbeatable convenience in a truly coveted Maitland address. Just a stroll from Maitland Preparatory School and mere minutes from the vibrant heart of Downtown Winter Park, this residence offers the best of both worlds. From the moment you arrive, you’ll sense the refined lifestyle within. soaring ceilings, abundant natural light, and premium finishes throughout. The chef’s kitchen is a showpiece sleek cabinetry, stone countertops, and top-tier appliances. Entertain effortlessly with open living spaces that flow seamlessly to relaxing patios or balconies. With 3 bedrooms and 3½ baths, each space is a sanctuary. The primary suite impresses with its spa-style bath and custom closets. Upstairs, the laundry is tucked neatly beside the bedrooms for ease and efficiency. Thoughtfully designed storage niches and built-ins complete the picture. The real magic is the location. You’re only 5 minutes from Winter Park’s world-class dining, boutique shops, cultural venues, riverside parks, and Sunday farmer’s market. Stroll through cobbled streets, enjoy al fresco cafés, or catch live music on Park Avenue this home gives you that full lifestyle. Live luxuriously in a community where neighbors share the same roof and an unspoken sense of sophistication reigns. While it feels like condominium living, this is fee simple ownership in a four-unit enclave with NO HOA fees. You get the benefits without the burden. This is more than just a home it’s a statement. Don’t miss your opportunity to own a residence that’s as beautiful as it is brilliantly located.

183 Orange Place, Maitland
$970,000
4 Beds ⋅ 3 Baths ⋅ Dommerich Hills SubDv. ⋅ 32751 Zip Code
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2031 Chippewa Trail, Maitland
$365,000
3 Beds ⋅ 3 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code
Welcome to Montacino, a gated community offering both convenience and charm. This updated 3-bedroom, 2.5-bath townhome combines modern finishes with a comfortable, functional layout. The first floor features an open design with spacious living, dining, and kitchen areas that flow seamlessly for everyday living or entertaining. The kitchen includes granite countertops, stainless steel appliances, and a stylish backsplash, with views of the covered back porch overlooking a peaceful green space. A convenient half bath is also located downstairs. Upstairs, the primary suite offers a private balcony, walk-in closet, and en-suite bath with dual vanities and a walk-in shower. Two additional bedrooms, a full bathroom, and a conveniently located laundry closet with washer and dryer complete the second level. Recent updates include new laminate flooring downstairs, along with a new microwave and refrigerator. The home also includes a one-car garage. Residents enjoy truly maintenance-free living, with the HOA fee covering internet, cable TV, exterior pest/termite control, roof repair and/or replacement, and exterior upkeep, as well as access to a resort-style pool, beautifully landscaped grounds, and lakeside sidewalks perfect for a stroll. A transferable home warranty is also available for added peace of mind. Ideally located near I-4, Winter Park, and Downtown Orlando, this home offers the perfect balance of a peaceful retreat and city convenience.

1291 Blessing Street, 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
$251,500
2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code
Live on Lake Maitland, part of the Winter Park Chain of Lakes, for just $250,000! This 2-bedroom, 1.5-bath condo in Lake Maitland Terrace is one of the most desirable units in the community, offering 816 square feet and a prime second-floor corner location with a screened-in front porch. Inside, you’ll find spacious living areas with bamboo flooring, plantation shutters, and abundant natural light. The porch extends your living space and is the perfect spot to quietly sip your morning coffee. Thoughtful upgrades set this home apart. The washer and dryer are conveniently located in the hallway, preserving closet space in both bedrooms. The primary bedroom features a true walk-in closet, and both bedrooms include custom closet systems that maximize storage and style. Opportunities to live on the Winter Park Chain of Lakes at this price point are incredibly rare. With its generous layout, upgraded features, and unbeatable location, this condo is a standout that won’t last long.

1140 S Orlando Avenue Unit F9, Maitland
$285,000
3 Beds ⋅ 2 Baths ⋅ Lake Eulalia Heights SubDv. ⋅ 32751 Zip Code
Tucked away in a tranquil setting, this charming 1958 split-level home offers a peaceful retreat surrounded by lush, thoughtfully landscaped gardens. As you arrive, you’ll feel an immediate sense of calm, greeted by a welcoming stairway and a serene garden path that invites you to explore before you even step inside. The main level features a spacious, light-filled living and dining area—perfect for entertaining or relaxing with loved ones. Large windows frame picturesque views of the gardens, flooding the space with natural light. Beneath the main level carpet, discover the timeless beauty of original terrazzo flooring, just waiting to be uncovered and restored. The lower-level bonus room is designed for both fun and function, complete with custom cabinetry and a sleek granite bar—ideal for hosting game nights or casual gatherings. Whether you’re entertaining or unwinding, this space offers flexibility and comfort. Step outside into your own tropical oasis, where mature landscaping, stone pathways, and private garden nooks create a perfect environment for relaxation and connection with nature. *The info in MLS is thought to be correct but not guaranteed*

721 Lake Avenue, Maitland
$255,000
1 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code
Step inside this beautifully reimagined Lake Maitland Terrace condo, where every detail has been thoughtfully updated for style and function. Renovated in 2021, this spacious one-bedroom residence embraces a modern design with clean lines, custom finishes, and a touch of industrial character from the exposed ceiling piping. The open layout features a bright great room that flows seamlessly into the kitchen, designed with both cooking and entertaining in mind. Highlights include Caesarstone quartz countertops, a mirrored backsplash, a farmhouse sink, KraftMaid soft-close cabinetry, and an oversized island with seating. Premium appliances such as a KitchenAid convection oven with induction cooktop, Bosch dishwasher, French-door refrigerator, and in-unit washer and dryer add convenience and sophistication. Originally configured as a two-bedroom, the condo has been transformed into a larger one-bedroom retreat but can easily be converted back if desired. The bathroom offers a tub/shower combination and an extra-wide pedestal sink. Enjoy a low-maintenance lifestyle with resort-style amenities, including a community pool, shuffleboard courts, fishing pier, and access to Lake Maitland and the Chain of Lakes. The unbeatable location puts you within walking distance of the Enzian Theater and Lake Lily, while Winter Park Village, Park Avenue, and A-rated schools are just minutes away.

1140 S Orlando Avenue Unit J2, Maitland
$545,000
4 Beds ⋅ 2 Baths ⋅ English Estates Unit 3 SubDv. ⋅ 32751 Zip Code
Seller is willing to assist with buyer closing costs or assist with interest rate buy down. This stunning 4-bedroom, 2-bathroom home has been completely reimagined from the ground up, offering flawless design, and premium finishes. Situated on a generous lot in a sought-after Maitland neighborhood, this home combines comfort, function, and style in every detail. Step inside to an inviting open-concept layout with luxury vinyl plank flooring, new lighting, and abundant natural light streaming through vinyl windows. The designer kitchen steals the spotlight with updates cabinetry, granite countertops with, and new appliances—crafted for the modern entertainer. The primary suite offers a tranquil retreat with a spa-inspired en suite bathroom featuring beautiful tilework and elegant fixtures. Both bathrooms have been tastefully renovated to reflect timeless design. Enjoy the added flexibility of a dedicated laundry room and a 2 car garage offering extra storage and workspace. Outside, the expansive backyard with a newly resurfaced in ground pool is your canvas for creating the outdoor lifestyle you've always wanted—whether it's hosting gatherings, gardening, or relaxing in the Florida sunshine. Located just minutes from top-rated schools, parks, shopping, and dining, 1470 Winston isn’t just move-in ready—it’s transformation perfected. Schedule your private showing today and fall in love with everything this exceptional home has to show. Clean 4 point inspection available by request.

1470 Winston Road, Maitland