Displaying: For Sale
Location: Maitland
Property Type(s): Condos
Price: $300,000 to $399,000
Do Not Show Listings
Maitland - 9 properties found
1000 WINDERLEY PL #141, MAITLAND, FL 32751
$300,0007 Days on yellowkey MLS ID: O6417569
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1275 Built: 1982Monthly Fee: $526 Tax: $2,725 (2025)Community: Sun Bay Club Condo Ut 1Condo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,725
Elementary School: Lake Sybelia Elem
High School: Edgewater High
Tax Year: 2025
Middle School: Lockhart Middle
Remarks: Updated GROUND-FLOOR condo in the secluded gated community of Sun Bay Club in Maitland, Florida overlooking Lake Destiny. Many units sit on lake fed ponds with fountains which offer a tranquil and peaceful atmosphere. Enjoy Florida life with a tennis court, a beautiful LAKE FRONT POOL, and LAKE ACCESS for residents to use boats and jet skis. The open-concept layout makes this 2 bedroom/2 bath condo feel so spacious. The LARGE KITCHEN (renovated 2023) features white kitchen cabinets, quartz countertops, a newer microwave (2024), and a 2025 dishwasher. Wood-look tile flooring flows through living areas connected to wood flooring throughout - no carpet! Extended sliding glass doors open to an ENCLOSED SUNROOM with windows and a peaceful pond view. Use it as a home office, reading room, or morning coffee retreat. Additionally, each bedroom has it's own screened in patio! The primary suite features double entry doors, access to both the enclosed sunroom and it’s own screened patio. It’s also equipped with a WALK-IN CLOSET with built-in shelving and an UPDATED 2026 ENSUITE BATHROOM with a new double sink vanity, modern mirrors, lighting, and a pocket door providing privacy to the shower and water closet room. The second bedroom offers DOUBLE CLOSETS with built-in shelving as well. HALLWAY BATHROOM UPDATED in 2026 with new vanity, mirror and lighting. HOA INCLUDES internet/cable and takes care of everything exterior including roof. Minutes from Maitland and Winter Park shopping, dining, and just a few minutes drive to highway I-4. Schedule a viewing today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Cece Wong (407-809-1440)
249 W LAKE FAITH DR #205, MAITLAND, FL 32751
$325,00041 Days on yellowkey MLS ID: O6406744
REDUCED by $14,000 (4.1%) on 06/22/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1739 Built: 1974Monthly Fee: $620 Tax: $1,339 (2025)Community: Lake Faith VillasCondo
Taxes:$1,339
Middle School: Maitland Middle
Remarks: One or more photo(s) has been virtually staged. Tucked away in this delightful lakefront community this beautifully renovated GROUND FLOOR condo offers so much, including a 2 PARKING SPACES - one is a deeded carport and the other is an open assigned parking spot... And there is a separate storage closet too! Situated on one level, this 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 entry 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). Along with these upgrades, there have been system updates including new hot water heater (2015), new AC (2016) and replumbed (2013). 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 (407-644-1234)
Listing Agent: Dawn Romance (407-929-2826)
1000 WINDERLEY PL #226, MAITLAND, FL 32751
$315,00058 Days on yellowkey MLS ID: O6402450
REDUCED by $10,000 (3.1%) on 06/09/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1538 Built: 1982 Tax: $1,318 (2025)Community: Sun Bay Club CondoCondo
Taxes:$1,318
Elementary School: None
High School: None
Middle School: None
Remarks: ***PRICE IMPROVEMENT***Welcome to this beautifully maintained 3-bedroom, 2-bath condo located in the highly desirable Sun Bay Club in Maitland. Offering 1,538 square feet of living space, this second-floor unit combines comfort, style, and convenience in a serene, gated community setting. Step inside to an impressive open floor plan featuring soaring 20-foot ceilings that create a bright and airy atmosphere, seamlessly connecting the living and dining areas—perfect for both everyday living and entertaining. The cozy fireplace adds warmth and charm, making this space feel like home from the moment you walk in. The newly remodeled kitchen is a standout, offering modern finishes and functionality for any home chef. Just beyond, enjoy your private sunroom with peaceful views of the community’s water fountain—an ideal spot for morning coffee or unwinding at the end of the day. Residents of Sun Bay Club enjoy access to exceptional amenities, including a clubhouse, pool, tennis courts, and scenic walking paths around the expansive lake. The location is unbeatable—just a short walk to the RDV Sportsplex and conveniently close to shopping, major highways, and everyday essentials. Plus, you’re only a short drive to downtown Orlando, world-famous theme parks, and Orlando International Airport. Additional highlights include a roof that is only 2 years old, offering added peace of mind. This is a fantastic opportunity to own a spacious, updated condo in a prime location—schedule your private showing today!
Listing is courtesy of: INVESTOR'S REAL ESTATE LLC (407-688-4355)
Listing Agent: Cece Mercado (407-300-8823)
2401 LEGACY LAKE DR #2401, MAITLAND, FL 32751
$355,00021 Days on yellowkey MLS ID: O6412788
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1707 Built: 2000Monthly Fee: $589 Tax: $2,250 (2025)Community: Visconti EastCondo
Taxes:$2,250
Remarks: All roads lead to Visconti East! Located in Maitland, bordering nearby scenic Winter Park (Park Ave./ Rollins College) this distinctive 3 story, 4 Bed/2.5 Bath townhome is situated directly off of I-4 and SR414, within 10 minutes to Downtown Orlando, Park Avenue, and close access to SR429, Winter Garden, and North Orlando. This home offers a one-of-a-kind floor plan with the entry foyer, hall closet, half bath and uniquely set up two car garage on the first floor, living room/kitchen + primary bedroom/bath on the second floor, and 3 bedrooms/ full bathroom, large hallway closet on the third level. All bedrooms feature spacious walk-in closets. Situated next to two fountain ponds that are overlooked from both sides of the unit on 2nd/3rd floors. No need to worry about additional projects, this very special and unique townhouse is move-in ready with top-quality updated features and architectural design, including imported Bianca Antico granite countertops, Italian travertine flooring and showers, stylish arches, and a massive built in bookcase. Shopping, Entertainment and Major Retail are all within miles, including downtown Maitland and Winter Park Village. Premier luxury gyms Genesis Health Club and Lifetime Fitness minutes away for ice skating, pickleball, aquatics and wellness community. Beautiful and safe bike trails accessible just by a short walk/ride. Come see all that this home and community has to offer! Call today for your private showing!
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Trace Christian, Iii (407-202-8135)
1000 S ORLANDO AVE #A31, MAITLAND, FL 32751
$300,00021 Days on yellowkey MLS ID: O6413581
1 Days Off yellowkey (back on 6/9/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 952 Built: 1964 Tax: $2,259 (2025)Community: Maitland Harbour AptsCondo
Taxes:$2,259
High School: Winter Park High
Remarks: Experience the best of lakeside living in this beautifully updated third-floor corner residence with panoramic views of Lake Maitland. Perfectly positioned along Orlando Avenue and adjacent to Fort Maitland boat ramp, the home combines convenience with a truly unique lifestyle just minutes from Winter Park’s shopping, dining, and cultural attractions. Inside, you’ll find luxury vinyl plank flooring throughout and a stunning kitchen designed for modern living, showcasing quartz countertops, sleek stainless steel appliances, custom cabinetry, and stylish finishes that create an inviting atmosphere for both cooking and entertaining. The spacious primary suite is highlighted by a custom-designed closet for optimal storage and comfort. Enjoy community amenities that make every day feel like a retreat, including a pool overlooking the lake and access to boat slips (via waitlist) on the highly coveted Winter Park Chain of Lakes. Whether you’re seeking a serene escape or a vibrant, connected lifestyle, this condo delivers the rare combination of location, water views, and thoughtful updates in one of Central Florida’s most desirable areas.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Chase Tate, Pllc (217-899-2619)
1140 S ORLANDO AVE #I14, MAITLAND, FL 32751
$325,00032 Days on yellowkey MLS ID: O6410595
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 816 Built: 1971Monthly Fee: $535 Tax: $2,086 (2026)Community: Lake Maitland TerrCondo
Taxes:$2,086
Elementary School: Dommerich Elem
Tax Year: 2026
Remarks: 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, a community pool where residents enjoy lake access with beautiful views. The amenities include a clubhouse with a full kitchen, kayak racks, a fishing pier, and a personal storage unit. 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 (407-622-2122)
Listing Agent: Michele Ostrander (407-435-3863)
204 QUAYSIDE CIR #304, MAITLAND, FL 32751
$395,000278 Days on yellowkey MLS ID: O6345967
REDUCED by $20,000 (4.8%) on 06/03/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1270 Built: 1984 Tax: $1,928 (2024)Community: Moorings On Lake Maitland CondoCondo
Taxes:$1,928
Tax Year: 2024
Remarks: SELLER PAYING CONCESSIONS OF 6 MONTH HOA FEES. Something is very special about Lakefront Living! Come visit this beautiful Lakefront Condo located at The Moorings On Lake Maitland, part of the Winter Park chain of lakes. Enjoy the Florida lifestyle in a carefree home with lake front amenities. Imagine Entertaining Family & Friends at the Pool or Heated Spa and the Clubhouse of the Moorings on Lake Maitland. Enjoy relaxing on the Lake Front Dock or on your own Private Enclosed Patio! Step inside this spacious 2 bedroom 2 bath great room plan, perfect for relaxing or entertaining. The beautifully upgraded kitchen has stainless steel appliances and granite counters and a charming dining nook. The master suite features an updated ensuite bath with dual sinks and a walk in shower with a custom glass enclosure. There is a generous walk in closet with custom built ins. Imagine coffee in the morning with lake views from your living room or your spacious patio. Only 5 minute drive to Winter Park's shops & Sidewalk Dining along the famed Park Avenue. Stroll over to Maitland's lovely Lake Lilly Park for Seasonal Events, Art Festivals, Concerts and local Farmer's Market! Incredible Location & Lifestyle!!!!
Listing is courtesy of: GALLERY PROPERTIES INTERNATIONAL (407-340-8487)
Listing Agent: Beatrice Cohen-Palladino, Pa (407-312-1820)
1140 S ORLANDO AVE #F11, MAITLAND, FL 32751
$349,000111 Days on yellowkey MLS ID: O6388276
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 816 Built: 1969 Tax: $3,419 (2025)Community: Lake Maitland Terrace AptsCondo
Taxes:$3,419
Remarks: This luxury condominium is in the established complex of Lake Maitland Terrace which sits on the shores of Lake Maitland, Winter Park Chain of Lakes. This immaculately maintained complex includes 11, 2-story, mid-century modern buildings sprawled across several acres, creating beautiful green space and picturesque views across the lake. This unit is special. A complete renovation with every detail accounted for, it is turnkey with enduring design. Warm wood floors are carried through spaces, kitchen has been opened to living room and flanked with windows allowing natural light to shine. Kitchen features white 42-inch shaker style cabinetry, quartz counters, subway tile backsplash, open shelving and stainless appliances. Counter seating is inviting and creates great kitchen function with loads of counter space for the aspiring chef. Primary suite is spacious with large closet storage, and renovated bath. Secondary bedroom and additional bath add to the flexibility of the unit, a guest room or home office. Indoor laundry makes this lock-and-go lifestyle even more appealing. Custom window treatments, closet system storage, updated HVAC, and fresh paint throughout. The location is pristine with walkability to the Enzian independent theatre, Lake Lily Park with a recreational trail and park, and home to community events, many restaurants and more. A short distance to Winter Park Village and Park Avenue and zoned for incredible schools with Dommerich Elementary, Maitland Middle & Winter Park Highschool. Complex is amenity-rich with sidewalks, community pool, generous dock, shuffleboards and more. Make this rare opportunity yours to own a little slice of this Maitland treasure.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Alison Mosley (407-304-6458)
1994 KENASTON RD #1994, MAITLAND, FL 32751
$399,000160 Days on yellowkey MLS ID: O6374243
REDUCED by $16,000 (3.9%) on 04/28/2026
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2103 Built: 1982 Tax: $4,582 (2025)Community: Ultra Vista CondoSpa: NoCondo
Taxes:$4,582
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: South Seminole Middle
Remarks: Located in the desirable city of Maitland, just three miles from Winter Park’s renowned Park Avenue, this extensively updated 3-bedroom, 3.5-bath townhouse offers modern living in a prime Central Florida location. Tucked within a quiet residential setting and zoned for highly rated Seminole County schools, the home provides easy access to dining, shopping, and entertainment while maintaining a sense of privacy and comfort. The thoughtfully designed layout offers flexibility and convenience across two levels. The main floor features a spacious primary bedroom complete with a walk-in closet and private bathroom. Also on the first level is a welcoming living area with vaulted ceilings, creating an open and airy feel, along with a dining space that looks out through French doors. The kitchen is well-appointed with stainless steel appliances, stone countertops, and ample workspace, making it ideal for everyday living and entertaining. A screened rear porch extends the living space outdoors, perfect for relaxing or enjoying Florida evenings. Upstairs, you’ll find a second primary bedroom with an attached bathroom, offering a private retreat for guests or multi-generational living. A third bedroom, also with its own bathroom, is located just off a landing that overlooks the living area below, adding architectural interest and an open-concept feel. Significant updates completed in 2024 enhance both comfort and long-term value, including a new roof, upgraded air conditioning system with a 10-year manufacturer warranty, fully updated plumbing, and modern electrical improvements with new breaker boxes, switches, and receptacles. Interior finishes include wood flooring on the main level, luxury vinyl plank flooring upstairs, tile in wet areas, energy-efficient Low-E double-pane windows, recessed LED lighting throughout, and updated fixtures in the kitchen and closets. The exterior was freshly painted in 2025, adding to the home’s curb appeal and move-in-ready condition. With its low-maintenance design, versatile floor plan, and unbeatable location near Winter Park’s Park Avenue and the scenic Chain of Lakes, this home presents
Listing Agent: Veronica Figueroa (407-519-3980)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.