Maitland Homes For Sale & Real Estate - 114 homes

Remarks: Updated & Move-In Ready Maitland Condo in Gated Community with Office/Flex Room & Rare 2-Car Garage — New Carpet, Paint & Appliances (2026) Beautifully updated three-level condo offering exceptional space, modern finishes, and a rare 2-car garage. This 2-bedroom, 2-bath home also includes a dedicated office/flex room—perfect for remote work or additional living space. Interior highlights include high ceilings, wood flooring, walk-in closets, and abundant natural light. Recent 2026 upgrades feature fresh interior paint, brand-new carpet, new stainless steel appliances (refrigerator 2024), renovated bathrooms, new window blinds, and a full-size in-unit washer and dryer. The Association has recently replaced the roof, and fees include exterior building maintenance, landscaping, valet trash service, water, sewer, and pest control—providing true low-maintenance living. Community amenities include two resort-style swimming pools, a fitness center, clubhouse, tennis and basketball courts, recreational areas, and a playground. Prime Maitland location just minutes from I-4, major highways, shopping, dining, and everyday conveniences. Home is offered with a Home Warranty. Available now for immediate occupancy.

Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)

Listing Agent: Nilufer Rohleder (407-962-7494)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 3-bedroom, 2-bathroom home that blends comfort, convenience, and an unbeatable location. From the moment you step inside, you’ll notice the inviting layout featuring a spacious living area filled with natural light and a functional kitchen equipped with newer stainless steel appliances—perfect for everyday living and entertaining alike. The home sits on a fully fenced lot with durable vinyl fencing, offering both privacy and a secure space for pets or play. Just beyond your backyard, enjoy direct access to a public playground—an ideal setup for families or anyone who loves being outdoors without losing the comfort of home. With a low HOA and a prime location, this home offers easy access to some of the area’s most exciting new developments and local favorites. You’ll be just minutes from the brand-new Lifetime Fitness currently under construction, the state-of-the-art HostDime data center, Winter Park Village, Whole Foods, and Amtrak. Plus, with quick access to I-4, commuting and weekend getaways are a breeze. Whether you’re a first-time buyer, downsizing, or looking for a solid investment in a growing area, this property offers the perfect blend of value, lifestyle, and location. Don’t miss your chance to make it yours!

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Dominick Florio (321-377-4045)

Remarks: Welcome to Visconti! A Gated Waterfront Community in the Heart of Maitland. Step into an easy, low-maintenance living with this move-in ready 2-bedroom, 2-bath condo located on the third floor, offering added privacy and a peaceful, elevated feel. With all new flooring and fresh interior paint, this home is completely refreshed and ready for its next owner. The split floor plan layout offers a comfortable and functional flow, ideal for both everyday living and entertaining. Natural light fills the space, creating a bright and inviting atmosphere throughout. Whether you’re starting your day or winding down in the evening, this home delivers a relaxed, low-stress environment that truly feels like home. Located within the highly desirable Visconti community, residents enjoy resort-style amenities including a sparkling pool, fitness center, clubhouse, tennis and basketball courts, playground, and scenic walking paths with a waterfront gazebo. The gated entry and beautifully maintained grounds enhance both privacy and curb appeal. The HOA includes water service and valet trash, helping simplify your monthly expenses and making condo living even more convenient. Positioned in one of Maitland’s most central locations, you’ll have quick access to I-4, 414, and 434, with nearby shopping, dining, and entertainment options including Maitland Promenade, Winter Park Village, Cranes Roost Park, and Uptown Altamonte. Downtown Orlando is just a short drive away. If you’re looking for a fully updated, move-in ready condo in a gated community with strong amenities and an unbeatable location, this one checks all the boxes.

Listing is courtesy of: INNOVATIVE REALTY, LLC (407-772-5555)

Listing Agent: Michael Rogers (407-782-3200)

Remarks: Great opportunity to own this 1-bedroom, 1-bathroom first-floor unit in a desirable and well-maintained community! This property offers a comfortable and functional layout with easy first-floor access, perfect for both homeowners and investors alike. Currently tenant-occupied with a lease in place through June 30, 2026, providing immediate rental income with future flexibility for personal use. Residents enjoy access to excellent community amenities, including a sparkling pool, fitness center, and playground, all within a lovely and welcoming environment. Conveniently located near major highways, shopping, dining, and entertainment, this property offers both lifestyle and investment potential. Don’t miss this versatile opportunity!

Listing is courtesy of: MIAMI TANGO INVESTMENTS REALTY (786-464-8803)

Listing Agent: Moses Nae (407-499-0240)

Remarks: One or more photo(s) has been virtually staged. HUGE PRICE IMPROVEMENT 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.

Listing is courtesy of: STRICKLAND REALTY GROUP INC (407-448-5068)

Listing Agent: Amanda Binns (407-448-5068)

Remarks: HUGE PRICE DROP! Whole Duplex. 6/4 (3 bed 2 bath in each unit). The Duplex is located in a cul-de-sac on a large lot that backs up to walking trail. Oakmont neighborhood has access directly to Sunrail Maitland Station. No HOA. Unit 933 has a fireplace for those cold Florida winters. The backyard is fully fenced and has an above-the-ground pool and a fully functionable bar with electric and running water. Great Investment Opportunity! Reroofed in 2018.

Listing is courtesy of: KGV REALTY GROUP (407-474-0844)

Listing Agent: Olaf Stenger (407-325-4147)

Remarks: A lovely well designed 4bdr. 2 bath home with an eat in kitchen open to a spacious family rm. A formal din.rm. and formal lvg.rm. are ready for any occasion. The long 2 lane brick driveway can accommodate multiple vehicles. Nearby schools for all levels and the amenities for recreation and entertainment are too numerous to list. This house should be added to your list when searching for your new home.

Listing is courtesy of: REALTY OF RIVERVIEW LLC (813-863-3948)

Listing Agent: Stephen Hachey (813-863-3948)

Remarks: Welcome home to this truly move-in-ready, beautifully updated 1-bedroom, 1-bath ground-floor condo located in the highly desirable Visconti West community in Maitland. This unit stands out from others of its size by offering upgrades and features that provide both comfort and peace of mind. From the moment you walk in, you’ll notice the new modern flooring throughout the living and bedrooms, creating a clean, updated look that flows seamlessly across the entire space. The kitchen has been completely refreshed and features a full suite of brand-new, high-efficiency appliances, including a built-in microwave, designed not only for style but also to help save money on your monthly utility bills. The home continues to impress with additional upgrades that are hard to find in comparable units, including a brand-new washer and dryer for added convenience. The bathroom has been fully updated with a sleek, modern design, featuring a step-in glass-enclosed shower that elevates the entire space. One of the standout features is the brand-new double pane glass window in the bedroom, offering enhanced insulation, reduced outside noise, and improved energy efficiency—another added benefit for comfort and cost savings. The open and functional layout provides a bright living space filled with natural light, while the private screened patio with additional storage offers the perfect place to relax or enjoy your morning coffee. What truly makes this property special is that no other unit of this size in the community offers this level of upgrades, modern finishes, and energy-efficient improvements. It’s a rare opportunity to own a condo where the big-ticket items have already been taken care of, allowing you to move in with confidence and peace of mind. Located in a gated, resort-style community with amenities including a pool, fitness center, basketball and tennis courts, playground, and beautifully maintained grounds, and just minutes from Winter Park, Downtown Orlando, Altamonte Springs, shopping, dining, and major highways—this home offers both lifestyle and convenience.

Listing is courtesy of: SHAWFIELD REALTY GROUP (407-963-7749)

Listing Agent: Carrie Sue Shawfield (407-963-7749)

Remarks: ENTERTAINING MAITLAND GROVE POOL HOME. Step inside to discover oversized rooms, including a spacious great room overlooking the covered lanai and swimming pool in a private setting perfect for gatherings. Back yard includes a vinyl privacy fence, Pool resurfaced with Pebble Tec. Patio and pool decking have pavers with plenty of room for extra lounging. Lots of Room for everyone, including lIving Room, Dining Room and 4 bedrooms. Kitchen features all new SS appliances and sink w/ faucet, a separate breakfast room and laundry room. Primary room features en suite updated bathroom with dual vanity, shower, w/ tub, walk in closet and large slider doors overlooking the serene pool. Home offers lots of closet and ample storage. Extra Long driveway with side entry oversized garage includes utility sink. Home has been lovingly cared for. Call to view today!

Listing is courtesy of: OVERSTREET REAL ESTATE INC (407-595-5546)

Listing Agent: Susan Filebark (407-595-5546)

Remarks: LAKESIDE LIVING in Maitland, Florida! Nestled canal front with direct access to Lake Charity, this vintage block home is built like a fortress with all the modern luxuries of today. A unique home for those who desire authenticity in both design and quality. A side entry garage leads to a courtyard like entrance with a marble path and asian influenced landscape. Double doors open into an expansive footprint with 3 large bedrooms, 2 baths and over 3,000 sq ft of living space. A 42 x 12 sunroom overlooking the water pays homage to the nostalgic Florida charm of this decade. No expense was spared when renovating this interior. Luxurious finishings and professional installation can make all the difference! Especially noted in the kitchen and baths! Upon entering, a Balsato Beige Porcelain fireplace surround wall anchors the space with plenty of areas to create conversational seating, a designer’s dream! The kitchen island is open to the entire living space with tons of storage and a double waterfall edge in Taj Mahal Quartzite. The perimeter counters are done in beautiful Bora Bora Quartz by Sharifstone. Real wood cabinetry in white dove compliments the earth tones giving a more transitional than modern vibe. Brushed gold hardware, lighting & plumbing fixtures are the perfect “jewelry” for the space! All new high end appliances convey. A brick fireplace graces the dining/living room wall (sounding like a song), yet another functional design opportunity to really create a home that works for YOU. There’s plenty of spots for an office, although not formally mentioned and the ability to use some of the square footage to create an additional “room” if needed. The primary suite closet takes the cake with all the fun features a dream closet should have! The ensuite bath has a lovely vanity with Quartz tops, dual sinks and a gorgeous shower with designer tile and a frameless glass door. Hardware is all in a matte black. The additional 2 bedrooms share a bath that has also had a complete remodel! This home is move in ready with a timeless style throughout. Flooring is a cohesive blend of tile and luxury vinyl plank. New roof 2024. With ideal proximity to fine dining & shopping in Maitland, Winter Park’s infamous Park Avenue and the Theme Parks, you’ll find yourself “staycationing” a little more often!

Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)

Listing Agent: Autumn Makin (352-455-0044)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Spacious one-story home featuring 4 bedrooms and 2.5 bathrooms with a functional, open layout. The kitchen offers a convenient breakfast bar overlooking the dining area. Step outside to enjoy the screened-in back porch and private in-ground pool, perfect for relaxing or hosting gatherings. The wood-fenced backyard provides added privacy, and the 2-car garage offers ample storage and parking. A fantastic opportunity with great indoor and outdoor living space!

Listing is courtesy of: MAINSTAY BROKERAGE LLC (800-583-2914)

Listing Agent: Eva Hockenberry (800-583-2914)

Remarks: Under contract-accepting backup offers. Welcome home to one of the established Maitland neighborhoods in a pristine location close to everything, Maitland Groves. A lovely brick walkway invites you up to a charming entrance with a bricked front porch. A four- or five-bedroom, four-bath home features nearly 3,000 square feet with a generous flex space, checks all the boxes. The spaces have been opened with living spilling into dining and a bay window adding charm to an ideal gathering room to entertain in. Custom tile throughout for seamless design with an abundance of light making the spaces inviting and easy to relax in. Kitchen is updated with custom 42-inch wood cabinets, custom moldings, stainless appliances with new dishwasher, gas range and oven, granite counters with counter seating, and unbelievable storage and cabinet space. Florida room spans the back of the house with a bricked floor, a wet bar and a dedicated office/bedroom. Updated primary bedroom with a large walk-in closet. Main bath with dual sinks and new rainfall shower heads, tower storage cabinets, seamless glass with walk-in shower, stone floor and custom tile. Outside patio enjoys a paver deck with large Florida pool and plenty of green space with room to grow. Other updates include roof (2021), solar energy system so energy bills are low, recently painted in select areas, wood laminate floors in all bedrooms, renovated second and third baths, spacious indoor laundry and mudroom for organization, fenced yard, recessed lighting in living spaces, re-plumbed, plantation shutters, 2021 pool pump, pool converted to saltwater system and new garage door. If you need space, this has it. Terrific schools, close to Interstate 4, downtown Maitland which is home to Lake Lily with a weekly farmers market, independently owned Enzian Theatre, world-class restaurants and fantastic community parks home to many community events.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Alison Mosley (407-304-6458)

Remarks: STUNNING MODERN REVIVAL IN THE HEART OF MAITLAND. Welcome to 344 Banyan Drive, where classic Maitland charm meets contemporary elegance. Experience the pinnacle of move-in-ready luxury at 344 Banyan Dr. This impeccably renovated residence has been transformed from top to bottom with sophisticated finishes and meticulous attention to detail. The open-concept interior shines with all-new flooring, contemporary baseboards, and a fresh, designer paint palette. The newly renovated kitchen is a true showstopper, boasting new custom cabinetry, sleek stone countertops, a stylish tile backsplash, and a premium stainless steel appliance package. Both the living spaces and the fully renovated bathrooms feature all-new designer lighting that creates a warm, inviting ambiance throughout. Every inch of this home feels brand new. Don't miss your chance to own a masterpiece in 32751!

Listing is courtesy of: REMAX SUNSTATE REALTY (416-450-7436)

Listing Agent: Ketan Patel (416-508-9037)

Remarks: Opportunity in the Maitland / Winter Park area! This one-owner home, held by the same family since the 1960s, is ideally located near shopping, dining, parks, and major roadways, providing convenient access throughout Central Florida. The property offers potential for renovation, expansion, or redevelopment, with a lot that provides space for future improvements. Ideal for homeowners, builders, or investors seeking a property in a desirable and established area. The adjacent property to the west (210 Alpine) is also available for purchase. Contact the listing agent for additional information and pricing on the neighboring parcel.

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

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

Remarks: Under contract-accepting backup offers. Welcome to 1529 Glastonberry Rd, a 4 bedroom, 2 bath pool home in the heart of Maitland. You will love this tastefully updated home. Upon entering, you will love the open floor plan and the way the homes flows from the spacious living room to the airy dining room straight into the bright, sparkling kitchen with stainless steel appliances. The whole area overlooks the inviting salt water pool and enclosed lanai. It's a dream space for entertaining. The primary overlooks the pool with a separate entrance, an updated bath and walk in closet. With three other great sized rooms, there is plenty of room and storage. Located in vibrant Maitland, shopping, restaurants, entertainment and night life are close.

Listing is courtesy of: RE/MAX TOWN CENTRE (407-996-3200)

Listing Agent: Tamara Rorman (407-491-1642)

Remarks: Welcome to 2466 Fieldingwood Rd, a fully re-imagined pool home in Maitland, FL. This 4 bedroom, 2 bathroom home has been completely renovated from top to bottom with a fresh, modern feel that is move-in ready and designed for today’s lifestyle. From the moment you arrive, you will notice the clean exterior, updated landscaping, and quiet street that sets the tone for the rest of the home. ALL major systems have been updates: Roof 2022, Plumbing 2024, Hot Water Heater 2024, AC 2016, and newer pool equiptment. Inside, the layout flows effortlessly with light-filled living spaces, updated flooring, and a bright, open feel throughout. The kitchen and main living areas connect seamlessly, making it perfect for both everyday living and entertaining. Step outside to your private backyard retreat featuring a newly refreshed pool and spacious deck area. This is the kind of space that feels like Florida living should. Whether you are hosting friends or enjoying a quiet evening at home, this backyard delivers. The bedrooms offer comfortable, flexible space for families, guests, or a home office, while the primary suite provides a clean and calming place to unwind. Located in English Estates, you are just minutes from Winter Park with easy access to 17-92, 436, and Red Bug Lake Road. Commuting is simple with quick access to I-4 and the express lane entrance, getting you to downtown Orlando efficiently. If you are looking for a fully updated home with a pool in a central location that actually makes your day-to-day life easier, this is one you need to see in person.

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Kristine Mckinley (407-415-2412)

Remarks: Set along a quiet, tree-lined street in Maitland, this 3 bedroom, 2 bathroom home with 1,922 square feet captures the essence of mid-century modern design with a fresh, updated edge. Clean lines, open flow, and a strong connection to the outdoors define the home from the moment you step inside. The living spaces feel intentional and uncluttered, with natural light highlighting the architectural simplicity that makes this style so enduring. An updated kitchen anchors the home with modern finishes and functionality, complemented by an eat-in dining area that invites everyday gathering. A dedicated bar area adds character and ease for entertaining, creating a space that feels both relaxed and refined. A separate office/flex space provides flexibility for today’s lifestyle, offering a quiet place to work or create without disrupting the flow of the home. Updated bathrooms carry a cohesive, minimalist design throughout, staying true to the home’s architectural roots. The outdoor space continues the story. Minimalist landscaping and open, usable areas create a calm and private setting that feels like a natural extension of the interior. It is a setting designed for both quiet mornings and easy evenings with friends. An optional HOA provides deeded lake access, adding a lifestyle component that is increasingly hard to find. All of this is paired with access to some of the most highly regarded schools in Central Florida and a location just minutes from Park Avenue, dining, and shopping. This is not just a home with style. It is a home with intention.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Brian Rotenberger (407-948-8478)

Remarks: Set on one of the most sought-after streets in Dommerich, this completely renovated home combines the solid construction of a 1963 block home with thoughtful modern updates throughout. From the moment you arrive, the circular driveway, classic brick accents, and welcoming front porch set the tone. Inside, a bright foyer opens to beautiful solid maple wood floors and a light, airy feel that carries throughout the home. To the right, the formal living room features built-in shelving and a striking brick wood-burning fireplace, while the adjoining formal dining room connects directly to the kitchen and can be closed off with pocket doors if you want a little separation. The eat-in kitchen is truly the heart of the home, showcasing rich solid cherry cabinetry, unique man-made glass countertops, a large farmhouse sink, and top-of-the-line stainless Bosch appliances including a built-in oven and gas cooktop. A generous peninsula overlooks the oversized family room, where French doors open to a stunning Florida room that fills the home with natural light. This space is a showstopper—large, lined with windows, and finished with soaring shiplap ceilings—creating the kind of room you’ll use year-round, with direct access to the backyard. The primary suite is spacious and refined with crown molding, a built-in closet plus a walk-in, and a beautifully renovated bath featuring matching glass countertops, a Kohler vanity, and a glass shower with both a large rain head and handheld fixture. Two additional bedrooms are generously sized and share an updated hall bath with a large vanity, classic subway tile, and a soaking tub. The interior also includes a well-equipped laundry room with cabinetry, a cedar storage closet, and access to the two-car garage. Out back, the fully fenced private yard offers plenty of room for entertainment, recently re-sodded with irrigation and enclosed with a brand new wood fence installed in 2025—leaving ample space for a future pool or patio if desired. Additional upgrades include smooth flat ceilings with recessed lighting throughout, new drywall, plantation shutters, updated windows and doors, and an energy-efficient hybrid water heater. Beyond the home itself, the location is hard to beat—just a short walk to Dommerich Elementary, Maitland Middle School, and Maitland Community Park offering tennis courts, indoor racquetball, and playgrounds. Zoned for highly regarded Winter Park High School. Call today to schedule your private showing!

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

Listing Agent: Maria Van Warner (407-256-8066)

Remarks: One or more photo(s) has been virtually staged. Welcome to 361 Hickory Drive, a truly special opportunity in a quiet, well-established community in the heart of Maitland. This charming home offers the perfect blend of comfort, mid-century historic charm and an unbeatable location making it ideal for those seeking both tranquility and convenience. Set on an oversized lot, this property provides ample space to entertain or enjoy the peaceful surroundings. The neighborhood is known for its quiet atmosphere with NO HOA, giving you the freedom to truly make this home your own without added restrictions. Upon walking in, you are greeted with an open concept living room space with the dining room to the left. The kitchen features ample cabinet space and a separate cooktop. The 2nd and 3rd bedrooms are generously sized with the primary including an en-suite bathroom. A BRAND NEW ROOF will be installed prior to closing, offering peace of mind. Upgrades include a New Water Heater (2026) and A/C(2019) ensuring comfort and efficiency. This home is also zoned in Top Rated Seminole County School Districts. Whether you're looking to settle into a serene neighborhood or invest in a property with strong fundamentals, this one checks all the boxes. Don’t miss your chance to call this Maitland gem home today!

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Emma Nelson (224-703-9190)

Remarks: Under contract-accepting backup offers. Prepare to be captivated by this fully renovated gem located in the highly sought after English Estates neighborhood. Offering 1,798 square feet of meticulously designed living space, this three bedroom, two bathroom home blends timeless charm with modern luxury. Every inch has been thoughtfully updated, including a brand new air conditioning system, new thermostat, and a newer roof. The home features an open layout with custom details such as designer sconces, a fluted accent wall, and an abundance of natural light throughout. The spacious primary suite includes a spa inspired bathroom designed to feel like a private retreat. Step outside to a fully fenced backyard oasis complete with a sparkling pool and outdoor shower, perfect for entertaining or relaxing in total privacy. Located in a no flood zone, this property offers peace of mind and lifestyle convenience. Just minutes from I-4, the Altamonte Mall, and a short walk or bike ride to the scenic Kawannee Trail, this location provides easy access to everything Orlando has to offer. This is a rare opportunity to own a stunning home in a well established neighborhood. Schedule your private showing today.

Listing is courtesy of: KELLER WILLIAMS TAMPA CENTRAL (813-865-0700)

Listing Agent: Andrea Heck (813-777-7219)