Maitland Real Estate

Maitland Real Estate

Welcome to Maitland, Florida – a hidden gem nestled in the heart of Orange County! Known for its rich history, stunning lakes, and vibrant community, Maitland offers a perfect blend of suburban tranquility and urban convenience. Just a stone's throw away from the bustling city of Orlando, Maitland boasts a charming atmosphere that attracts families, professionals, and retirees alike.

One of the standout features of Maitland is its picturesque lakes, including the serene Lake Minnehaha and the expansive Lake Sybelia. These bodies of water not only provide stunning views but also offer a plethora of recreational activities such as boating, fishing, and picnicking along the scenic shores. The city is also home to the beautiful Maitland Art Center, a historic landmark that showcases local art and hosts cultural events throughout the year.

Maitland’s downtown area is a delightful mix of boutique shops, cozy cafes, and gourmet restaurants, making it a perfect spot for a leisurely stroll or a night out. The city is also well-connected, with easy access to major highways and public transportation, ensuring that you’re never far from the action.

Education is a priority in Maitland, with top-rated schools and educational institutions that cater to students of all ages. Whether you’re looking for a family-friendly neighborhood, a vibrant community, or a serene place to retire, Maitland has something to offer everyone.

Discover the charm of Maitland, where community spirit thrives, and the beauty of Florida living awaits you!

Newest Listings in Maitland

1 Beds ⋅ 1 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

Virtually Staged. Welcome to this well-maintained and move-in-ready second-floor condo, offering comfort, convenience, and a great location! This charming 1-bedroom, 1-bathroom unit features a spacious layout, a large walk-in closet, and a private outdoor patio where you can enjoy your morning coffee or relax after a long day. The property is currently vacant and ready to show, making it an excellent opportunity for a first-time homebuyer, seasonal resident, or investor looking for a low-maintenance property. The community offers a variety of desirable amenities, including a beautiful swimming pool, playground, and green spaces, and a great fitness/exercise room for residents to enjoy. The low HOA fee makes this property even more attractive for those looking for an affordable and convenient lifestyle. Laundry facilities are conveniently located outside across from the building. Located in a convenient area close to public transportation, stores, shops, restaurants, and everyday necessities, this condo provides easy access to everything you need. Whether you are looking for a comfortable place to call home or a great investment opportunity, this property offers an excellent combination of location, amenities, affordability, and convenience. Don't miss the opportunity to see this beautiful second-floor condo. The unit is vacant, in good condition, and ready for its new owner. Schedule your showing today!

559 Flemming Way Unit 203, Maitland

3 Beds ⋅ 3 Baths ⋅ Dommerich Hills First Add SubDv. ⋅ 32751 Zip Code

Expect to be impressed with this beautifully maintained 3-bed/3-bath, 1-story Dommerich pool home. With almost 2,300 square feet of thoughtfully designed living space, this home offers over $100K in impactful updates and improvements, including a newer roof (2022), newer HVAC system (Dec 2023), recent conversion from septic to sewer (2026), new pool pump and filter system, newer paver driveway and drainage, and more. Step inside to a spacious family room where a stacked stone wood-burning fireplace sits between elegant built-in shelving and cabinetry to present a warm and inviting focal point. The family room opens to the dining area and adjacent breakfast bar that overlooks the kitchen…an ideal design for both everyday living and entertaining…all anchored by timeless hardwood flooring. The sunny kitchen features skylights newer stainless appliances (all replaced within the last 5 years), a cooktop with a pot filler, and a new beverage refrigerator for added convenience. Sliding glass doors at the rear of the dining area open to the covered lanai and private backyard, offering a seamless indoor-outdoor experience with pool views. Outside you’ll enjoy a private backyard oasis, complete with a covered lanai, open paver patio deck, a covered gazebo with festive lights and a large sparkling pool, all fully-fenced creating the perfect space to relax, entertain, and enjoy Florida living. Enhancing versatility, pocket doors off the side of the dining room open to reveal a den/flex space, and a 207- sq ft Florida room with a dedicated 1.5 ton ductless AC unit. These 2 areas are perfect for a home office, workout room, or playroom. There is a 3rd full bathroom adjacent to the den. The desirable split-bedroom floor plan provides comfort and privacy, with 2 secondary bedrooms positioned off the front hallway while the Primary Suite sits at the rear of the home, featuring wood floors, a large walk-in closet, and sliding glass doors for direct access to the backyard area. Located off the 2-car garage entrance, the spacious indoor laundry room includes utility sink with storage cabinetry, along with an adjoining office nook for a cozy and functional workspace, a storage closet, and access to a 3rd full bath with extra linen storage. Zoned for A-rated Dommerich Elementary, Maitland Middle and Winter Park High School, this exceptional home combines thoughtful updates, flexible living spaces, and a fantastic outdoor setting in a highly desirable location.

2414 Chinook Trail, Maitland

2 Beds ⋅ 2 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

Welcome to Carrington Park Condominiums! This 2-BEDROOM, 2-BATHROOM condo is located on the TOP FLOOR, (only1 flight of stairs) offering added privacy with no neighbors above. The comfortable floor plan provides plenty of space for everyday living, while the SCREENED-IN BALCONY is the perfect spot to relax and enjoy the Florida weather. A STACKABLE WASHER-DRYER is conveniently located inside the unit, and the REFRIGERATOR CONVEYS for added convenience. The condo building is ideally situated NEXT to the COMMUNITY POOL, making it easy to take advantage of one of the communities most popular amenities. The community also features a LARGE FITNESS CENTER and PLAYGROUND, providing something for everyone. Conveniently located in Maitland with easy access to major highways, shopping, dining, and everyday necessities, this condo offers a great combination of location and low-maintenance living. Whether you're searching for a PRIMARY RESIDENCE OR INVESTMENT/RENTAL PROPERTY, this Carrington Park condo is a wonderful opportunity!

2313 Haywood Court Unit 201, Maitland

3 Beds ⋅ 5 Baths ⋅ Hidden Estates Unit 3 SubDv. ⋅ 32751 Zip Code

A RARE OPPORTUNITY IN HIDDEN ESTATES— NEARLY AN ACRE, LOW HOA & AN INCREDIBLE ENTERTAINER’S PARADISE! Tucked away in one of Maitland’s best-kept secrets, this expansive home offers over 3,200 square feet of living space on an oversized lot. With a long driveway providing abundant parking, a fully fenced yard and privacy sound wall, this property offers a level of space and privacy that is increasingly hard to find! The spacious and flexible floor plan features 3 bedrooms plus a large office that could easily be converted to a 4th bedroom, along with a living room, dining room, family room with a cozy fireplace, spacious eat-in kitchen, wet bar and an upstairs study area. The enormous first-floor primary suite includes a seating area, large ensuite bath with garden tub and separate shower, and two closets. One of which is oversized and large enough to create an office, dressing room, nursery or even a home gym. Upstairs, two additional bedrooms share a convenient dual Jack-and-Jill bath, offering excellent privacy and functionality. But the true showstopper is the outdoor living and entertainment space! A beautiful sunroom opens directly to the pool and an incredible backyard designed for entertaining. The sun room serves as a massive game room. The outdoor space has a beautiful freshly painted deck, multiple covered bar areas and an abundance of space for pool parties, family gatherings, game nights or simply relaxing in your own private retreat. A shed and expansive fenced yard provide even more room for hobbies, recreation and storage. The roof and HVAC were replaced in 2020. This is an incredible canvas to make your own while enjoying the space, privacy and amenities that are already here. Hidden Estates is a well-maintained, tucked-away community where homes rarely become available, yet you're still conveniently close to everything Maitland has to offer with easy access into Downtown Orlando, tons of shopping and dining options, great schools & hospitals. Call for more information and for your private showing today!

233 Flame Avenue, Maitland

4 Beds ⋅ 2 Baths ⋅ Forest Brook 4th Sec SubDv. ⋅ 32751 Zip Code

Updated 4-bedroom, 2-bath heated pool home situated on a .27-acre corner lot in the sought-after Forest Brook neighborhood. From the moment you arrive, you’ll notice the paver driveway, mature landscaping, pops of color, and warm wood accents that give the home great curb appeal. Step inside to an open floor plan with soaring ceilings and plenty of natural light. The spacious living room features vaulted ceilings and offers plenty of flexibility for different furniture layouts. At the center of the home is the updated kitchen, highlighted by a level 3 stone countertop island with breakfast bar seating and pendant lighting. Shaker-style cabinetry with under cabinet lighting, a dry bar, tile backsplash, decorative molding, single-basin sink, and updated cabinet hardware complete the space. Just off the kitchen is a bright dinette with sliding glass doors leading to the covered patio. The split-bedroom floor plan places the primary suite on one side of the home, with bedrooms 2, 3, and 4 and the second bathroom on the opposite side. The primary bedroom features a beautifully updated ensuite bath with marble tile flooring, dual-sink vanity, level 3 stone countertops, and a spacious frameless glass walk-in shower with upgraded tile and dual rainfall shower heads. A large walk-in closet provides plenty of storage. The secondary bedrooms have also been updated and include built-in closets. The indoor laundry room offers additional space for shelving and storage. Outdoor living is a big part of this home. Sliding glass doors open to a screened and covered patio with tile flooring overlooking the fenced backyard and solar-heated pool. The pool was resurfaced in 2017, and the pool pump was replaced in 2021. Make this space your own personal outdoor oasis. Major updates include a NEW ROOF in 2025, HVAC in 2024, and newer exterior paint. Forest Brook has a optional HOA and offers a convenient Maitland location with easy access to Winter Park, Baldwin Park, Audubon Park, Winter Springs, Oviedo, SR-417, UCF, shopping, dining, and more. A move-in-ready pool home with plenty of updates, indoor space, and outdoor living!

812 Woodside Road, Maitland

1 Beds ⋅ 1 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

Welcome to 484 Banyon Tree Circle, Unit #100, Maitland, a well-updated 1 bedroom, 1 bathroom FIRST-FLOOR condo offering 759 square feet of comfortable living space. This move-in ready unit features a functional layout, a modern kitchen with granite countertops, and an IN-UNIT WASHER AND DRYER COMBO for added convenience. The spacious primary bedroom offers a walk-in closet. The living room has sliding glass doors that provide direct access to the front porch, creating a great space to enjoy your morning coffee or relax outdoors. Enjoy resort-style community amenities including a community pool, fitness center, clubhouse, and playground. The first-floor location provides easy access with no stairs, making everyday living simple and convenient. Ideally located in Maitland, close to shopping, dining, entertainment, major highways, and everything Central Florida has to offer. Whether you're looking for a comfortable primary residence or an investment opportunity, this condo is a great place to call home. Schedule your showing today!

484 Banyon Tree Circle Unit 100, Maitland

2 Beds ⋅ 2 Baths ⋅ Building 14 Visconti West SubDv. ⋅ 32751 Zip Code

Auction Property. Auction Property. AUCTION/OCCUPIED. Buyers will be required to sign a occupancy declaration. 2-bedroom 2-bathroom condominium in gated community of Visconti West situated off Lake Shadow. Quick access to interstate 4 and Florida turnpike. Property is sold “as is” with NO property disclosures, NO inspection reports, NO interior photos, NO lease in place, NO access- The seller does not represent or guarantee occupancy status. NO VIEWINGS of this property. Please DO NOT DISTURB the occupant. Buyer is responsible for obtaining possession of the property upon closing.

1225 Lake Shadow Circle Unit 14102, Maitland

3 Beds ⋅ 2 Baths ⋅ Floridahaven 1st Add SubDv. ⋅ 32751 Zip Code

Rare opportunity in desirable Maitland! Bring your builder and your vision to this approximately .40-acre homesite located directly across the street from Lake Seminary. Situated in an established residential area, this property offers an excellent opportunity to create a custom home in a highly desirable Central Florida location. Home has lake access & Community Park. The existing structure is in poor condition with known mold present and is being marketed primarily for its land and redevelopment potential. Buyers should anticipate demolition or substantial redevelopment of the existing home. The backyard also features an existing in-ground swimming pool that has been drained. No representations are being made regarding the condition, functionality, or future usability of the pool. With approximately .40 acres, there is plenty of room to envision a beautiful new residence and outdoor living space designed to take advantage of this desirable Maitland setting. Enjoy being directly across from Lake Seminary while remaining convenient to Maitland, Winter Park, shopping, dining, recreation, and major roadways. Build new. Create your vision. Take advantage of a hard-to-find .40-acre homesite in an established Maitland location. Property is being sold AS-IS. Buyer and Buyer’s Agent are responsible for independently verifying all information important to Buyer, including zoning, lot dimensions, building requirements, utilities, demolition requirements, permitting, pool condition, and intended use. Do not enter the existing structure without authorization.

265 Lake Seminary Circle, Maitland

3 Beds ⋅ 4 Baths ⋅ Bretton Woods SubDv. ⋅ 32751 Zip Code

Elegant Pool Home with Classic Florida Charm & Modern Comfort in Bretton Woods. Discover timeless charm and modern convenience in this stunning brick ranch, ideally situated on an expansive lot in desirable Bretton Woods. Thoughtfully updated for today’s lifestyle, this one-of-a-kind home combines character, comfort, and exceptional functionality. It’s easy to fall in love with this special property from the moment you arrive. Mature oak trees frame the front yard, while a welcoming porch sets the stage for the beautifully updated interior, featuring engineered hardwood flooring and a gourmet kitchen outfitted with top-of-the-line stainless steel appliances, including an induction Bosch cooktop, GE Monogram French door wall oven, GE Advantium microwave/oven, GE French door refrigerator, and KitchenAid dishwasher. A butler’s pantry provides exceptional storage and a seamless extension of the gourmet kitchen, making entertaining and everyday living effortless. The spacious owner’s suite offers a private retreat with an en-suite bath and cedar sauna. French doors open to an enclosed spa for the ultimate relaxation experience. A generous guest suite includes its own full bath and walk-in closet. A centrally located half bath provides added convenience for family and guests, while a separate full pool bath offers easy access from the outdoor living spaces. Recent improvements provide added peace of mind, efficiency, and year-round comfort. These include a newer roof, kitchen and powder room remodel, new Trane HVAC system with new ductwork featuring three separate zones, each with its own thermostat, new windows, pool pump, irrigation controls, and exterior paint. Step outside to your own private oasis. The expansive, fully fenced backyard features a sparkling pool framed by a large screened lanai, offering the perfect setting for entertaining, relaxing, or enjoying Florida’s beautiful weather. A large double gate provides convenient side-yard access for boat parking, while an outdoor shower adds to the poolside experience. Practicality is just as impressive, with a sizable laundry room, abundant storage, a circular driveway, and a two-car garage. A dedicated parking pad in front of the garage can accommodated an RV. Blending the warmth and character of old Florida with thoughtful modern updates, this exceptional property offers space, privacy, and convenience just minutes from I-4 and all that the Orlando area has to offer. A truly distinctive home with an unforgettable combination of charm and amenities to accommodate your lifestyle.

1501 Oranole Road, Maitland

3 Beds ⋅ 2 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

Need Room! Welcome home to this spacious 1612 S.F. first-floor condominium featuring three bedrooms and two full baths in a well-maintained community conveniently located near shopping, dining, and Full Sail University. Step inside to find brand-new luxury plank flooring throughout the living and bedroom areas, ceramic tile in the kitchen and bathrooms, and absolutely no carpet! Blinds on all windows and ceiling fans add to the comfort and convenience of this inviting home. The kitchen comes complete with refrigerator, range, microwave, and dishwasher, while a brand-new washer and dryer are also included. Relax and enjoy Florida's beautiful weather year-round from your private screened-in lanai, with the community pool and playground conveniently located nearby. The HOA offers exceptional value by covering water, sewer, trash, building insurance, roof, grounds maintenance, and the community pool. With its desirable first-floor location, fresh updates, generous three-bedroom floor plan, and convenient location, this condo offers easy Florida living and is ready for you to make it home!

2308 Haywood Court Unit 100, Maitland

3 Beds ⋅ 3 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code

Welcome to beautiful Montacino, Enclave at Maitland, a well maintained Mediterranean inspired gated community. This well appointed town home features three bedrooms and two and 1/2 bathrooms. The first floor is a desirable open floor plan with a welcoming foyer, 1/2 bathroom, fully tiled living/dining room, kitchen with bar top and access to the first floor covered patio. The kitchen has beautiful rich cabinetry, dark granite countertops with newer stainless steel appliances as well as pantry for additional storage space. The second floor features all three bedrooms, two bathrooms and ideally located central laundry closet with 2 year old (high capacity) washer and dryer included. The primary bedroom features a private ensuite bathroom with an updated double vanity, gorgeous walk-in shower with rain shower option, a walk in closet with built-in storage cabinets and a private balcony overlooking community green space. The flooring on the second floor is luxury vinyl plank in the bedrooms and hallway and tile in the bathrooms. (carpet only on stairwell). The interior was just freshly painted and new fans were added in the living room and primary bedroom, allowing for a turnkey move-in ready experience. Additionally there are high end plantation shutters throughout! There is an attached one car garage and private paver driveway as well as open community parking. Montacino features a resort style community pool and beautiful sidewalks overlooking Lake Charity perfect for an evening stroll. All this with exceptionally easy access to I-4 and Maitland Blvd allow for convenient shopping and dining and commuting. Schedule a tour today!

1257 Blessing Street, Maitland

1 Beds ⋅ 1 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

**LOCATION, LOCATION!** Welcome to this charming and cozy 1-bedroom, 1-bathroom condo, ideally located in a convenient and desirable area near Semoran Blvd and Howell Branch Rd. This move-in-ready second-floor unit offers comfort, convenience, and easy access to everything you need. Enjoy being just walking distance from shopping, restaurants, supermarkets, and everyday essentials. The community offers a refreshing swimming pool, perfect for relaxing or enjoying quality time with family and friends, as well as ample parking for residents and guests. The property is also conveniently located near schools and educational institutions, including Rollins College, making it an excellent opportunity for professionals, or anyone looking for a convenient Central Florida location. HOA includes water, adding even more value and convenience. Whether you're looking for your next home, a low-maintenance place to live, or an investment opportunity, this condo is one you won't want to miss! Schedule your showing today and come see all this property has to provide.

2520 Caper Lane Unit 204, Maitland

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