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CHERRYWOOD GARDENS - O6411069 - 341 CHERRYWOOD GARDENS DR #2, MAITLAND, FL 32751 4 Days on yellowkey
$185,000 | Condo | 2 beds | 2.0 baths
Under contract-accepting backup offers. 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!
Listing is courtesy of: SPHERA REALTY LLC
LAKE MAITLAND TERR - O6410595 - 1140 S ORLANDO AVE #I14, MAITLAND, FL 32751 8 Days on yellowkey
$325,000 | Condo | 2 beds | 1.5 baths
One or more photo(s) has been virtually staged. Where Maitland's pristine waters meet a modern lifestyle! This luxury condominium in the coveted Lake Maitland Terrace community offers a rare blend of elegance and convenience on the shores of Lake Maitland within the famed Winter Park Chain of Lakes. Nestled among lush green spaces, this impeccably maintained mid-century modern complex boasts easy access to boutique shops, upscale dining, and vibrant entertainment. This unit stands out with its unique two-bedroom, one-and-a-half-bath layout—a rare find in the community, where most units are built with just one bath. Sunlight floods in through large windows, and warm wood floors flow throughout. This charming efficiently designed kitchen, with light cabinetry with contrasting hardware, quartz counters, and stainless steel appliances, is perfect for entertaining. Beyond the comforts of the home, enjoy the exclusive opportunity to secure a boat slip—a prized amenity in this tranquil lakeside retreat. Complex is amenity-rich with sidewalks, community pool, generous dock, shuffleboards and more. Walk to Lake Lily Park’s events, the Enzian Theater, and be just minutes from Winter Park Village and Park Avenue. Zoned for top-rated schools—Dommerich Elementary, Maitland Middle, and Winter Park High—this is a chance to embrace the best of Maitland living. Don’t miss your chance to claim this exceptional retreat as your own.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO
PARK LAKE VILLAS CONDO - O6410478 - 616 VILLA CIR #536, MAITLAND, FL 32751 9 Days on yellowkey
$252,000 | Condo | 2 beds | 2.0 baths
Welcome home to this beautifully updated 2-bedroom, 2-bath condo offering 1,256 square feet of comfortable living in a quiet and well-maintained Central Florida community. With major upgrades already completed, this move-in-ready home combines modern style, energy efficiency, and low-maintenance living. Step inside, from your dedicated parking spot directly in front of the unit, to discover a stunning fully remodeled kitchen. Completed in 2025 and featuring granite countertops, soft-close cabinetry and drawers, recessed lighting, and an oversized island perfect for entertaining, meal prep, or casual dining. The open living space with upgraded bamboo flooring flows seamlessly through elegant French doors to a private fenced back patio and screened-in porch, creating the perfect indoor-outdoor retreat for relaxing year-round. The spacious primary suite includes a beautifully remodeled bathroom with updated shower tile and new ceramic tile flooring, completed in 2025. Additional recent upgrades provide peace of mind and long-term value, including upgraded energy-efficient windows, added insulation, a new electric panel, and a tankless hot water heater — all completed in 2025. The AC was replaced in 2020, the roof was replaced in 2024, and the exterior was freshly repainted in 2026. Enjoy the convenience of community amenities including a pool, just steps away from your front door, and exterior maintenance handled by the property management company, allowing for truly easy Florida living. Ideally located near restaurants, shopping, and major interstates, this home offers quick and convenient access throughout Central Florida while still being tucked away in a peaceful community setting. Schedule your private showing today and experience all this upgraded condo has to provide!
Listing is courtesy of: NESTA REAL ESTATE CONSULTANTS
VISCONTI EAST - O6409051 - 1927 LEGACY COVE DR #1927, MAITLAND, FL 32751 12 Days on yellowkey
$215,000 | Condo | 2 beds | 2.0 baths | 2 gar
Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Resort-style amenities, low-maintenance living at a reasonable price, and a move-in ready home come together at 1927 Legacy Cove in beautiful Maitland. As you approach this GATED COMMUNITY, you will feel at ease with the added layer of security. Parking at the condo, you will see an extremely rare feature - an ATTACHED 2 CAR GARAGE! Inside, your eyes will be immediately drawn to the kitchen features: NEW STONE COUNTERTOPS, updated cabinets, STAINLESS STEEL APPLIANCES, pantry, tile backsplash, and breakfast bar. FRESH INTERIOR PAINT and tall ceilings throughout the home give it a clean, bright feel. Laminate floors and crown molding give the main living spaces a special touch. Upstairs, you will find NEW CARPET and a walk-in closet in both bedrooms. The conveniently-located 2nd floor laundry area is situated near the main bedrooms for everyday ease. The HOA provides exceptional value with a comparatively low monthly fee that includes: water/sewer, concierge trash pickup, and exterior maintenance, and resort-style amenities including a gorgeous COMMUNITY POOL, fitness center, clubhouse, playground, a basketball court, fishing pier, and tennis courts. They also just replaced the roof on this building within the last year or so. Conveniently located less than 1.5 miles from I-4 and approx 1 mile from SR-414, this home offers easy access throughout Greater Orlando. Historic Park Avenue in Winter Park is just 5 miles away, and Lake Eola in Downtown Orlando is approx 8 miles away. Altamonte Mall, multiple hospitals, Seminole State College, Rollins College, and even Orlando’s famed theme parks are all within easy reach.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY
LAKE MAITLAND TERRACE APTS - O6404875 - 1140 S ORLANDO AVE #E2, MAITLAND, FL 32751 16 Days on yellowkey
$235,000 | Condo | 1 beds | 1.0 baths
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.
Listing is courtesy of: METRO CITY REALTY
LAKE FAITH VILLAS - O6406744 - 249 W LAKE FAITH DR #205, MAITLAND, FL 32751 17 Days on yellowkey
$345,000 | Condo | 3 beds | 2.0 baths | 1 car
Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Tucked away in this delightful lakefront community this beautifully renovated condo offers so much! Situated on the first floor, the condo overlooks the charming grounds and a peek of Lake Faith from the living areas and porch. Inside is a treat for sure with a large open living and dining room layout that is light and bright. The unit has a luxury vinyl plank flooring throughout most of the unit and tile flooring in the kitchen and baths. The kitchen is updated with granite countertops and plenty of cabinetry. Off the living room is an expansive back porch that has tile flooring and was recently updated with newer windows and door (2024) .... And off the dining area is a charming, covered porch. So, lots of areas to enjoy day to day or if you like to entertain. The master bedroom is a spacious size and also opens to the back porch… You will love the master bath - completely redone with a large shower, a stylish vanity with ample storage as well as a make-up vanity and a generous walk-in closet. The 2 additional bedrooms are both a good size with great closet storage. Other notable features are the inside laundry closet with open shelving and newer LG washer and dryer (2024) and the custom shades installed in the living areas and bedrooms (2023). This unit has an open dedicated parking space...plus a DEEDED CARPORT! And it also has an exterior dedicated STORAGE CLOSET. This complex offers a private, tranquil atmosphere and has terrific amenities including a gated entrance, clubhouse, and pool. And the location couldn’t be more convenient, with easy access to I-4 as well as a new retail and restaurant development within a short stroll. This is one not to miss!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES
VISCONTI EAST - A4693485 - 1150 LAKE SHADOW CIR #3304, MAITLAND, FL 32751 19 Days on yellowkey
$139,900 Reduced | Condo | 2 beds | 2.0 baths
Sought-after Visconti community of Maitland. The lowest 2-2 entry point currently available. This third-floor, 2-bed, 2-bath, 1,048 sqft condo features updated flooring, designer paint, LED lighting, new ceiling fans, updated faucets, and a screened patio with exterior storage. Community amenities include two pools overlooking Lake Shadow, tennis courts, lakeside walking paths, dog stations, and car wash stations, minutes to I-4, 429, downtown Orlando. Sold as-is, priced to sell.
Listing is courtesy of: JOSEPH WALTER REALTY LLC
PARK LAKE TWNHS PH 02 - O6406031 - 868 TOWN CIR #123, MAITLAND, FL 32751 24 Days on yellowkey
$260,000 | Condo | 3 beds | 2.5 baths | 1 gar
This is the kind of first home that makes life easier. With over 1,500 SqFt, 3 bedrooms, 2.5 baths, and thoughtful updates throughout, this Maitland condo gives you room to grow without the heavy upkeep of a single family home. The remodeled kitchen features quartz counters, stainless steel appliances, and updated cabinetry, while downstairs tile flooring keeps maintenance simple. Enjoy a large dining area, separate living room, laundry room, enclosed patio, and attached garage. Upstairs, the spacious primary suite opens to a balcony overlooking the courtyard. The community pool, lake access, and HOA covered exterior maintenance add even more value, all in a location close to Maitland favorites, Winter Park, and downtown Orlando.
Listing is courtesy of: EPIQUE REALTY, INC.