Refine Search
Sort by
$180,000
2 Beds 2 Baths Cherrywood Gardens SubDv. 32751 Zip Code
Under contract-accepting backup offers. Are you an investor looking for a passive income? This may be the answer to your goal! A 2-Bedroom, 1 Full Bath & 1/2 Bath with tenants in place is ready for a steal at Cherrywood Gardens! A quiet, small, and well- maintained community tucked in the heart of Maitland where most tenants stay long-term due to its strategic location and great features. Unit 341 has its own 2 reserved parking space right in front, plus available guests parking. This cozy unit with a covered front porch has its own closet laundry, a sliding door at the back end allowing natural lights indoor and overviewing the courtyard. The unit is beautifully maintained with tenants in place. The community is also surrounded with mature trees and pathways on the sides of units with a small pool the occupants can enjoy. And, of course guests parking slots are also available. This is truly an investor’s dream. Tenant's lease expires October 31, 2026. The occupancy rate is high at Cherrywood Gardens according to the Property Manager. Come and view the property before it’s gone in the market!

450 Cherrywood Gardens Dr Unit 450, Maitland

$189,900
2 Beds 2 Baths Visconti West SubDv. 32751 Zip Code
Welcome home to this beautifully updated and maintained 2-bedroom, 2-bath corner unit condo at Visconti West in Maitland! Located on the third floor, this light filled home features vaulted ceilings and an open, airy floor plan designed for comfortable living. The spacious primary suite includes an en-suite bathroom, while both bedrooms offer generous walk-in closets. The kitchen and bathrooms feature upgraded granite countertops and luxury vinyl plank flooring throughout the entryway, kitchen and bathrooms. Enjoy your morning coffee or unwind in the evening on the screened balcony. Additional highlights include an in-unit laundry room with washer and dryer, AC unit (2023), and hot water heater (2025). Residents enjoy gated access and resort style amenities including a pool, fitness center, clubhouse, tennis court, basketball court, valet trash pickup Monday through Friday, and a scenic pond and lake. Conveniently located just minutes from I-4, shopping, dining and entertainment, this home offers the perfect blend of style, comfort, and an unbeatable location.

1475 Lake Shadow Circle Unit 6307, Maitland

$199,000
2 Beds 2 Baths Visconti East SubDv. 32751 Zip Code
Experience resort-style living in the heart of Maitland at the highly desirable gated community of Visconti. This beautifully maintained three-story townhome offers 1,280 square feet of thoughtfully designed living space plus an oversized attached garage, providing the perfect combination of comfort, functionality, and low-maintenance living. The open-concept main living level features luxury vinyl flooring, soaring ceilings, abundant natural light, and a spacious kitchen with stainless steel appliances, updated countertops, tile backsplash, breakfast bar seating, and generous cabinet space. The spacious primary suite offers a large walk-in closet and private bath, while the additional bedrooms provide flexibility for guests, a home office, or growing families. A full-size interior laundry room, ample storage, and neutral finishes make this home truly move-in ready. Visconti residents enjoy an impressive collection of amenities including a gated entrance, resort-style swimming pool, a state-of-the-art fitness center, playground, scenic walking paths, car wash station, and beautifully landscaped grounds shaded by mature oak trees. Conveniently located just minutes from I-4, Winter Park, Downtown Orlando, AdventHealth, RDV Sportsplex, shopping, dining, and entertainment, this home offers the perfect blend of convenience, lifestyle, and value.

1952 Legacy Cove Drive Unit 1952, Maitland

$195,900
1 Beds 1 Baths Lake Maitland Terrace Apts SubDv. 32751 Zip Code
LAKE ACCESS LIVING in one of Central Florida's most desirable locations! Welcome to 1140 S. Orlando Ave E11, a move in ready condo ideally located on the Winter Park and Maitland border in the sought after Lake Maitland Terrace community. Enjoy private access to Lake Maitland, part of the prestigious Winter Park Chain of Lakes, where you can spend your days paddle boarding, kayaking, boating, fishing, or simply relaxing by the water. Community amenities include a brand new lakefront pool, clubhouse available for private events, shuffleboard, putting green, community laundry facilities, COMMUNITY DOCK and additional storage. Inside, you'll find a functional floor plan with separate living and dining spaces, abundant natural light, and a well maintained interior that's ready to enjoy or personalize over time. Whether you're looking for a primary residence, seasonal retreat, or investment opportunity, this condo offers exceptional value in an unbeatable location. Just minutes from Park Avenue and walking distance to local favorites including the Enzian Theater, Eden Bar, Luke's Kitchen and Bar, Antonio's, Francesco's, the Shoppes at Maitland, and beautiful Lake Lily Park. With easy access to downtown Winter Park, downtown Orlando, I 4, shopping, dining, and entertainment, this is low maintenance Florida living at its best.

1140 S Orlando Avenue Unit E11, Maitland

$140,000
2 Beds 2 Baths Carrington Park A Condo SubDv. 32751 Zip Code
Welcome to Carrington Park — one of Maitland’s most conveniently located communities! This ground-floor 2-bedroom, 2-bathroom condo offers 1,200+ square feet of comfortable living space at an unbeatable price point, making it an ideal primary residence or a smart addition to any investment portfolio.The open living and dining area flows naturally to a private screened patio perfect for enjoying Florida’s year-round weather without the bugs. Both bedrooms are generously sized, and the split-style layout offers privacy for owners and guests alike.Residents enjoy access to community amenities including a sparkling pool, fitness center, and more, all just steps from your front door. Situated at the corner of Howell Branch and SR-436, you’re minutes from shopping, dining, and major employers, with easy access to UCF, Full Sail, and Downtown Orlando.Whether you’re looking for a place to call home or a turnkey rental opportunity in a high-demand corridor, this one checks all the boxes. Priced at $140,000, schedule your showing before it’s gone.

2329 Coawood Unit 103, Maitland

$184,900
2 Beds 2 Baths Visconti West Condo SubDv. 32751 Zip Code
If you are looking for a terrific property, look no further! You or your tenant can live the lifestyle deserved in this RESORT-STYLE, video-monitored GATED COMMUNITY located on beautiful Lake Shadow in the heart of Maitland Center. This two-bed/two-bath, 2nd-story, CORNER UNIT features an OPEN floor plan with a LIVING/DINING COMBO and 9-FOOT CEILINGS. The KITCHEN includes a breakfast bar, closet pantry, INSIDE UTILITY CLOSET with washer and dryer, and neutral tile. All appliances convey at closing. DOUBLE MASTERS each offer an en-suite bath and a walk-in closet. The 20 X 20 living area provides lots of sunlight and features a built-in nook with glass shelving you can use as you choose. In 2024, the interior was painted, and carpet was installed. Through sliders, you can unwind at the end of a busy day on the SCREEN-ENCLOSED tiled LANAI and enjoy a TRUE ESCAPE. If extra storage is needed, a patio closet awaits! This GORGEOUSLY LANDSCAPED and PET-FRIENDLY community offers two LAKESIDE POOLS with Wi-Fi access, a club-quality FITNESS CENTER, grand CLUB ROOM with CATERING KITCHEN, fully-equipped BUSINESS CENTER, lighted TENNIS courts, BASKETBALL court, car wash area, two laundry facilities, 24-HOUR MAINTENANCE, WATER, SEWER, and a Monday-Friday VALET WASTE REMOVAL SERVICE. The condo community boasts a newer tile roof, reflecting ongoing care and investment in the property. Located minutes away from SR 414, I-4, 429, Routes 434 and 436; it is a quick drive to downtown Orlando, Cranes Roost Park, and to the upscale shopping and dining at Altamonte Mall, Altamonte Towne Center, Winter Park Village, and Winter Park’s quaint Park Avenue. Enjoy Florida living at its best! This property may be under audio & visual surveillance.

1440 Lake Shadow Circle Unit 8201, Maitland

$185,600
2 Beds 2 Baths Cherrywood Gardens SubDv. 32751 Zip Code
Looking for an investment with passive income? This may be the answer to your goal! A 2-Bedroom, 2-Full Bath with tenants in place is ready for steal at Cherrywood Gardens! A quiet, small, and well- maintained community tucked in the heart of Maitland where most tenants stay long-term due to its strategic location and great features. Unit 341 has its own 2 reserved parking space right in front, plus available guests parking. This cozy unit with a covered front porch has its own closet laundry, a sliding door at the back end allowing natural lights indoor and overviewing the courtyard. The unit is beautifully maintained with updates: cabinets, countertops, lights and tile floorings. The community is also surrounded with mature trees and pathways on the sides of units with a small pool the occupants can enjoy. And, of course guests parking slots are also available.This is truly an investor’s dream. Tenants renewed for another year until January 31, 2027. The occupancy rate is very high at Cherrywood Gardens according to the Property Manager. Come and view the property before it’s gone in the market!

341 Cherrywood Gardens Dr Unit 2, Maitland

$194,995
1 Beds 1 Baths Lake Maitland Terrace Apts SubDv. 32751 Zip Code
PRICE IMPROVEMENT! Live the lake lifestyle in this beautifully updated 1-bedroom condo located in the iconic mid-century modern community of Lake Maitland Terrace. Completely refreshed in 2025, this first-floor residence features a brand-new HVAC system, new appliances including washer, dryer, and kitchen disposal, updated kitchen countertops, and new flooring throughout the living areas. Freshly painted and thoughtfully enhanced, the home blends timeless mid-century character with modern comfort and style. The spacious bedroom showcases sleek modern concrete flooring, adding to the authentic architectural aesthetic and contemporary feel. Perfectly positioned within a charming two-story mid-rise building, this residence offers effortless access to the community’s exceptional waterfront amenities and relaxed lakefront atmosphere. Set on Lake Maitland—the largest lake on the Winter Park Chain of Lakes—residents enjoy direct lake access for boating, kayaking, canoeing, fishing, and water-skiing. A private community dock is located on-site, while the City of Maitland public boat ramp sits conveniently next door. Boat slips may also be available upon request. The location is truly unbeatable. Just one block from Lake Lily and Fort Maitland Park, and only minutes from Park Avenue, residents can walk to the Maitland Farmers Market, local restaurants, coffee shops, gym, dry cleaning, barber shop, boba tea, and more—all directly across the street. Enjoy easy biking access to Park Avenue for premier shopping, dining, and entertainment. Residents of Lake Maitland Terrace enjoy outstanding amenities including a newer community pool, lakefront clubhouse with breathtaking views available for private events, on-site laundry facilities, free unlimited water, and twice-weekly valet trash service. Experience maintenance-free living where iconic mid-century modern design meets modern updates and an unmatched Central Florida lakefront lifestyle.

1140 S Orlando Avenue Unit E2, Maitland

$169,900
2 Beds 1 Baths Visconti West SubDv. 32751 Zip Code
Amazing upgraded two-bedroom, one bath Condo in the gated waterfront community at Visconti in Maitland with features of spacious living and comfortability. This stunning Condo Unit features with large windows letting in plenty of natural light and giving the common living area a fresh air feel. The dining/living combo opens to a big, screened patio through sliding glass doors. The kitchen overlooks the living and dining room and contains a full suite, including the refrigerator, range, dishwasher, disposal and plenty of cabinet and countertop. The bedroom is also including a large walk-in closet. This unit has oversized laundry room that includes full-size washer and dryer.Visconti community comes with professional maintenance of Ponds, professionally landscaped and well-maintained common areas as well as a BEAUTIFUL Resort Style Pool and Club House along with tennis court, fitness, basketball court, car washing area ext. Primely located close to all shopping, entertainment areas and just minutes to major highways, I4. You don't need to look any further for your Dream Home! Schedule your viewing today! Note: Some of the pictures are showing the virtual staging of the unit and the furnitures are not included to the listing

1375 Lake Shadow Circle Unit 11203, Maitland

$190,000
2 Beds 2 Baths Visconti West SubDv. 32751 Zip Code
Virtually Staged. Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo in the sought-after Visconti community, where comfort, convenience, and lifestyle come together. Located on the third floor, this light-filled residence features soaring vaulted ceilings that create an open, airy feel, complemented by abundant natural light throughout. Ideally positioned just steps from the clubhouse, you’ll enjoy effortless access to resort-style amenities, including a sparkling pool and fully equipped fitness center—perfect for both relaxation and an active lifestyle. This move-in ready condo is an excellent opportunity for both homeowners and investors alike. With quick access to I-4, commuting to Downtown Orlando is easy, while the shopping, dining, and entertainment of Altamonte Springs are just minutes away. Opportunities like this in Visconti don’t last—schedule your private showing today.

1100 Lake Shadow Circle Unit 2307, Maitland

$175,000
2 Beds 2 Baths Visconti West Condo SubDv. 32751 Zip Code
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.

1440 Lake Shadow Circle Unit 8305, Maitland

$113,000
1 Beds 1 Baths Carrington Park A Condo SubDv. 32751 Zip Code
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!

2422 Branch Way Unit 100, Maitland

$111,000
1 Beds 1 Baths Carrington Park A Condo SubDv. 32751 Zip Code
Discover this beautifully maintained 1-bedroom, 1-bath condo in the highly desirable Banyan Tree Condominium of Maitland. Located on the second floor, this unit boasts abundant natural light, a functional layout, and low-maintenance living—perfect for families, first-time buyers, or savvy investors seeking rental income. Enjoy affordable HOA fees ($255.86/month) covering building insurance, pool, landscaping, and common areas. Situated in Seminole County, close to top-rated schools, shopping, dining, and major highways. Flood Zone X, no CDD, not currently homesteaded. This is an exceptional opportunity to own a comfortable home or a turnkey investment property. Act now—buyer to verify all information including school zoning, rental restrictions, and flood insurance requirements.

416 Banyon Tree Circle Unit 206, Maitland

$120,000
3 Beds 2 Baths Carrington Park A Condo SubDv. 32751 Zip Code
Welcome to this spacious 3-bedroom, 2 bath main floor condo in Carrington Park, offering comfort, convenience and strong investment potential. This unit features numerous updates including a new HVAC system, new front door, new tub/shower combo and new updated bathroom vanities. The kitchen has been refreshed with new cabinets, updated countertops and newer appliances, along with some new flooring throughout. The open layout provides generous living and dining space, while the screened in porch offers a relaxing outdoor retreat. With three well-sized bedrooms and easy ground floor access, this condo is ideal for anyone seeking low maintenance living in a desirable community. Carrington Park offers inground pool, playgrounds, green space, security guard, fitness center and is in the heart of Maitland.

2423 Branch Way Unit 105, Maitland

$99,000
1 Beds 1 Baths Carrington Park A Condo SubDv. 32751 Zip Code
Welcome to this well-located condominium in Maitland, featuring fresh interior paint, brand-new carpet, a new air conditioning system, and a new refrigerator. This comfortable unit offers a functional layout and is conveniently located near shopping, dining, and major roadways, providing easy access throughout the Orlando metropolitan area. The property is also ideally situated near several well-known educational institutions, including Rollins College (founded in 1885), Full Sail University, and Valencia College, making it an attractive option for students, faculty, and investors seeking rental potential. A great opportunity for homeowners or investors looking for value in a desirable and centrally located area.

2426 Branch Way Unit 200, Maitland

$130,000
1 Beds 1 Baths Visconti West Condo SubDv. 32751 Zip Code
Virtually Staged. Water views, major system upgrades, and the best value in Visconti. This beautifully updated 1-bedroom, 1-bath condo is priced $16,000 below the next comparable unit in the community and features over $15,000 in recent improvements, including a brand-new Goodman 2-ton 14.3 SEER HVAC system (2025), a new water heater with an expansion tank (2026), and stylish shaker kitchen cabinets (2025). Enjoy tranquil pond views from both the living room and bedroom, with a large sliding glass door leading to your private balcony. The open-concept layout offers abundant natural light, built-in shelving, and a functional floor plan designed for comfortable everyday living. A separate laundry room adds extra convenience and storage. Located within the gated Visconti community, residents enjoy resort-style amenities including two swimming pools, a fitness center, clubhouse, tennis and basketball courts, and scenic paths. HOA fees include water, sewer, and trash service. Conveniently located just minutes from I-4, Downtown Orlando, Winter Park, Altamonte Springs, major employers, shopping, dining, Walt Disney World, Universal Orlando, and Orlando International Airport. Whether you're a first-time homebuyer, downsizing, or seeking a low-maintenance investment property, this move-in-ready condo offers exceptional value and location. Mortgage savings may be available for buyers of this listing.

1275 Lake Shadow Circle Unit 13206, Maitland

$199,000
2 Beds 2 Baths Visconti West SubDv. 32751 Zip Code
*HUGE PRICE REDUCTION* Step into effortless living with this beautifully maintained 2-bedroom, 2-bath condo nestled in a highly sought-after gated community! From the moment you enter, you’re greeted by stunning luxury vinyl flooring that flows seamlessly throughout, setting the stage for a bright, open-concept layout that’s perfect for both relaxing and entertaining. The stylish kitchen shines with updated granite countertops and a convenient breakfast bar—ideal for morning coffee or hosting friends. Each spacious bedroom offers its own private retreat, complete with walk-in closets and en-suite bathrooms featuring upgraded vanities for a sleek, modern feel. Unwind on your private balcony with new travertine flooring, where peaceful fountain views create the perfect backdrop for your morning or evening escape. Enjoy added convenience with in-unit laundry and the peace of mind of an AC system replaced in 2021. This vibrant community truly has it all—resort-style pool, clubhouse, fully equipped fitness center, tennis and basketball courts, scenic walking paths, and a charming gazebo overlooking serene lake views. Perfectly located in Maitland, you’re just minutes from shopping, dining, the charm of Park Avenue in Winter Park, and major highways—giving you the ideal blend of tranquility and accessibility. This is the lifestyle you’ve been waiting for!

1325 Lake Shadow Circle Unit 12202, Maitland

$130,000
2 Beds 2 Baths Carrington Park A Condo SubDv. 32751 Zip Code
Discover your dream condo in the tranquil Carrington Park neighborhood of Maitland! This charming 2-bedroom, 2-bathroom residence is perfect as your smart investment. Enjoy an open living area, a spacious Owner's Suite with an ensuite bathroom, and a generous closet. The community offers fantastic amenities, including a lovely pool, gym, and playground, providing endless opportunities for relaxation and recreation. Conveniently located near 436 and I-4, you’ll be just minutes away from shopping, dining, entertainment, hospitals, and the Altamonte Mall. Don't miss out on this incredible opportunity! Schedule your viewing today and start picturing a life of comfort and serenity in your new condo.

420 Banyon Tree Circle Unit 102, 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

$178,900
2 Beds 2 Baths Cherrywood Gardens SubDv. 32751 Zip Code
Welcome to Cherrywood Gardens! This charming 2-bedroom, 1.5-bath condominium offers 953 sq. ft. of comfortable living space in the heart of Maitland. Step inside to find an inviting living and dining room combo, a bright kitchen with included appliances, and a primary suite with a walk-in closet. Enjoy your mornings on the front porch or take advantage of the community’s amenities, including a pool & clubhouse. Association fees cover water, sewer, trash, exterior maintenance, and grounds upkeep—making for worry-free living. Located near top-rated schools, shopping, dining, and major roadways, this home provides both comfort and convenience. Whether you’re a first-time buyer, downsizing, or looking for an investment, this condo is a great opportunity to own in a desirable Maitland community.

107 Cherrywood Gardens Drive Unit 8, Maitland