Location: Maitland
Keyword(s): Lockhart Middle
Keyword(s) Middle School: Lockhart Middle
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1000 WINDERLEY PL #141, MAITLAND, FL 32751
$300,00020 Days on yellowkey MLS ID: O6417569
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1275 Built: 1982Monthly Fee: $523 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)
1275 LAKE SHADOW CIR #13206, MAITLAND, FL 32751
$139,000140 Days on yellowkey MLS ID: O6383068
2 Days Off yellowkey (back on 7/6/2026)
REDUCED by $6,500 (4.5%) on 06/16/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 672 Built: 2000Monthly Fee: $400 Tax: $1,942 (2024)Community: Visconti West CondoSpa: NoCondo
Taxes:$1,942
Tax Year: 2024
Remarks: Under contract-accepting backup offers. 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.
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: Trevin Perez (305-793-6807)
1952 LEGACY COVE DR #1952, MAITLAND, FL 32751
$199,0006 Days on yellowkey MLS ID: O6422110
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1280 Built: 2000 Tax: $3,285 (2025)Community: Visconti EastTownhouse
Taxes:$3,285
Remarks: 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.
Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)
Listing Agent: Patricia Sullivan (407-719-6550)
2847 SHADOW VIEW CIR #2847, MAITLAND, FL 32751
$210,00027 Days on yellowkey MLS ID: O6414837
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1280 Built: 2000 Tax: $3,285 (2025)Community: Visconti East Bldg 27Condo
Remarks: Visconti Condo - Gated Community with lots of amenities only 8 miles from Downtown Orlando. This community situated on the north shore of Lake Shadow offers swimming pool, fitness center, clubhouse, tennis and basketball courts. Conveniently located close to I-4 and Maitland Blvd. Multi level home features an open floor plan with kitchen living/dining and office on main 2nd floor and 2 bedrooms 2 bathrooms on the 3rd floor. This home also features an attached 2 car garage with plenty of room for your vehicles or extra storage. HOA includes exterior maintenance, landscaping, valet trash, water, sewer and pest control.
Listing is courtesy of: MARKET CONNECT REALTY LLC (407-250-4708)
Listing Agent: Brian Piekos (407-414-8230)
1927 LEGACY COVE DR #1927, MAITLAND, FL 32751
$215,00049 Days on yellowkey MLS ID: O6409051
0 Days Off yellowkey (back on 7/1/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1280 Built: 2000 Tax: $2,025 (2025)Community: Visconti EastCondo
Taxes:$2,025
Remarks: Under contract-accepting backup offers. 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 (407-977-7600)
Listing Agent: Kristin Duncan (407-274-5911)
2150 TORTOISE SHELL DR, MAITLAND, FL 32751
$409,90076 Days on yellowkey MLS ID: O6392895
REDUCED by $15,000 (3.5%) on 06/18/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1512 Built: 1997Monthly Fee: $17 Tax: $5,334 (2025)Community: WinfieldSingle Family
Taxes:$5,334
Remarks: Virtually Staged. FRESHLY UPDATED CABINETRY, FOURTH BEDROOM OPTION ADDED! Welcome to this beautifully maintained home in the heart of Maitland, offering the perfect blend of comfort, functionality, and Florida lifestyle living. This thoughtfully designed residence features a bright and open layout with spacious living areas, soaring ceilings, and an abundance of natural light throughout. The kitchen serves as the heart of the home, complete with ample cabinetry, generous counter space, and a convenient breakfast bar that opens seamlessly to the main living and dining areas, ideal for both everyday living and entertaining. Sliding glass doors lead to a private backyard with a paver patio, creating the perfect space to relax or host gatherings. The primary suite offers a peaceful retreat with plenty of space, natural light, and an en-suite bathroom for added convenience. Additional bedrooms are well-sized and versatile, perfect for guests, a home office, or growing households. Situated on a quiet street, this home features a fully fenced yard, mature landscaping, and a two-car garage. Conveniently located near shopping, dining, major roadways, and top-rated schools, this property combines tranquility with accessibility. Don’t miss the opportunity to make this move-in ready Maitland gem your own, schedule your private showing today.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Claire Sims, Llc (203-767-8109)
1000 WINDERLEY PL #239, MAITLAND, FL 32751
$299,00098 Days on yellowkey MLS ID: O6395472
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1164 Built: 1982Monthly Fee: $523 Tax: $489 (2025)Community: Sun Bay Club CondoSpa: NoCondo
Taxes:$489
Remarks: Elegantly renovated two-bedroom, two-bath second-floor condo in the gated community of Sun Bay Club on Lake Destiny in Maitland. Vaulted ceilings and abundant windows create a bright, airy atmosphere throughout. The gourmet kitchen has been fully updated with 42-inch custom hardwood cabinets, Zodiaq (Cambrian) quartz countertops, a Kohler farmhouse sink, stainless steel appliances, and porcelain wood-plank floors. The kitchen opens to the dining and living areas, featuring a built-in desk, wood-burning fireplace, custom built-ins, clerestory windows, and triple sliding doors leading to a private balcony with a storage closet. The split floorplan includes the primary suite with a walk-in closet and a renovated bath with dual vanities, hardwood cabinets, designer fixtures, a glass-block shower, and natural light from a private skylight. The secondary bedroom has two wall closets and an upgraded bathroom with custom cabinets, a tub, and a skylight. Meticulously maintained with pride of ownership reflected throughout. Features include double-door entry, knockdown ceilings, designer finishes, ample storage, and an interior laundry closet. Additional updates include a new Carrier AC (2023), a new hot water heater (2025), and a new tile roof with gutters, downspouts, and skylights (2024). Sun Bay Club offers a beautiful lakefront pool, lake access with a boat ramp, a tennis court, a dog park, a community meeting room, and a car wash area for residents. Its central location is just minutes from I-4, RDV Sportsplex, Publix, shopping, and dining. Downtown Maitland, Winter Park, and Orlando are only a short drive away.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Nancy Bagby (407-620-8868)
1010 WINDERLEY PL #149, MAITLAND, FL 32751
$429,90019 Days on yellowkey MLS ID: O6417777
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1651 Built: 1999Monthly Fee: $375 Tax: $4,525 (2025)Community: Villas Lake DestinyTownhouse
Taxes:$4,525
Remarks: This beautifully positioned residence offers an open and inviting layout designed for easy living and entertaining. Enjoy peaceful water views of Lake Destiny with no rear neighbors, creating a private backdrop and a rare sense of space and tranquility. Whether relaxing indoors or stepping outside, the serene setting delivers a true sense of comfort and escape. The home also features a spacious 2-car garage, providing convenience and additional storage. Thoughtfully updated and move-in ready, this home offers valuable recent improvements including a new A/C unit (2022), water heater (2022), tile roof replacement (2022), updated paint and modern light fixtures (2023), and both bathrooms beautifully renovated in 2021. The kitchen is complemented by newer appliances, adding both style and functionality. Step outside and enjoy even more value with the outdoor deck currently being replaced, creating an enhanced outdoor living space to take in the beautiful lake setting. Residents enjoy access to exceptional community amenities including a pool, tennis courts, and access to Lake Destiny, all within a dog-friendly community designed to support an active and enjoyable lifestyle. Ideally located with quick access to major highways, dining, shopping, business centers, and everything Maitland and the greater Orlando area have to offer, this property delivers the perfect blend of lifestyle and accessibility. Whether enjoying your morning coffee overlooking Lake Destiny or coming home after a busy day, this residence offers the privacy, views, updates, and location today’s buyers are searching for.
Listing is courtesy of: GENSTONE REALTY (407-237-0905)
Listing Agent: Hafid Boujidi (407-729-3894)
1440 LAKE SHADOW CIR #8201, MAITLAND, FL 32751
$199,00025 Days on yellowkey MLS ID: O6416664
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1111 Built: 2000Monthly Fee: $532 Tax: $3,298 (2025)Community: Visconti West CondoCondo
Taxes:$3,298
Remarks: 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.
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Susan Schneider (407-461-1150)
1010 WINDERLEY PL #127, MAITLAND, FL 32751
$332,50099 Days on yellowkey MLS ID: O6395028
REDUCED by $6,500 (1.9%) on 05/01/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1563 Built: 1997Monthly Fee: $375 Tax: $4,625 (2025)Community: Villas Lake DestinyTownhouse
Taxes:$4,625
Remarks: Back on the market through no fault of the property. Recently appraised at $340,000 and inspections were completed without issue. A great opportunity for a qualified buyer seeking a smooth transaction and quick closing. Tucked into one of Maitland's most coveted lakefront enclaves, this beautifully updated townhome sits within a quietly maintained, tree-lined setting with direct access to Lake Destiny, a private community boat ramp, resort-style pool, and tennis courts, all just minutes from I-4, the 414, RDV Sportsplex, and the dining and shopping corridors of Maitland Center. First impressions set a private and secluded tone with a wrought-iron gated courtyard leads to a covered entry porch before you reach the front door. Inside, soaring vaulted ceilings and a dramatic arched transom window above the sliding glass doors flood the main level with natural light, creating an airy, open feel that far exceeds the square footage on paper. Wide-plank tile flooring runs throughout the main living areas, connecting the open living and dining spaces to a thoughtfully updated kitchen featuring white shaker cabinetry with crown accents, solid stone countertops, stainless steel appliances including a French door refrigerator and built-in microwave, pendant lighting above the breakfast bar peninsula, and a subway tile backsplash. The sliding doors open directly to a private screened patio framed by mature landscaping, creating the kind of indoor-outdoor flow that defines Florida living at its best. Upstairs, three generously sized bedrooms each offer ceiling fans, ample closet space, and brand new carpet and paint. The primary suite stands out with a 26ft footprint, two closets including a walk-in, and an ensuite bath featuring dual vanities, a full-wall vanity mirror, and a walk-in shower. Two additional bedrooms and a full bath complete the upper level, with the layout providing genuine separation and privacy between spaces. Back on the main floor, a versatile 9x9 bonus room with indoor laundry handles the day-to-day, and the full-size washer and dryer convey. The big-ticket items are handled: 30-year tile roof replaced in 2023, HVAC installed in 2020, and brushed nickel fixtures updated throughout. The one-car garage with additional driveway parking and the gated courtyard entry give this unit a sense of privacy and security rare in townhome living. Whether you are looking for a low-maintenance primary residence, a lock-and-leave second home, or a smart investment in a well-managed community with real amenities and a lakefront address, this one makes an easy case.
Listing is courtesy of: DON HARKINS REALTY LLC (321-377-0341)
Listing Agent: Donald Harkins, Iii (321-377-0341)
1375 LAKE SHADOW CIR #11103, MAITLAND, FL 32751
$199,00062 Days on yellowkey MLS ID: O6405605
REDUCED by $10,777 (5.1%) on 05/29/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 898 Built: 2000 Tax: $2,714 (2025)Community: Visconti West CondominiumCondo
Taxes:$2,714
Remarks: Stunning fully renovated 2-bedroom, 1-bath condo featuring a complete top-to-bottom remodel completed in 2026, located in the highly desirable gated Visconti West community in Maitland. This move-in ready unit features luxury vinyl plank flooring throughout, a beautifully updated kitchen with modern soft-close cabinetry, sleek finishes, and stainless steel appliances, as well as a bright open-concept living and dining area. The living and dining room combination opens to a screened-in patio through large sliding glass doors, allowing for abundant natural light throughout the home. The kitchen includes a full suite of brand-new appliances, including a range, over-the-range microwave, dishwasher, refrigerator, and disposal, along with modern soft-close cabinetry and ample countertop space. Additional upgrades include a new water heater (2026) and AC system (2020). The unit also features a full-size washer and dryer and an additional storage closet on the patio. Community amenities include a resort-style pool, fitness center, clubhouse, tennis courts, and lake access. Conveniently located near shopping, dining, major highways, and downtown Orlando. Excellent opportunity for owner-occupants or investors.
Listing is courtesy of: M2M REALTY (407-401-2275)
Listing Agent: Margo Ford (407-761-6408)
1776 BOBTAIL DR, MAITLAND, FL 32751
$519,99990 Days on yellowkey MLS ID: G5110747
REDUCED by $5,000 (1.0%) on 05/27/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2344 Built: 1998Monthly Fee: $17 Tax: $2,578 (2025)Community: WinfieldSpa: NoSingle Family
Taxes:$2,578
Remarks: Welcome to 1776 Bobtail Drive — the kind of home that doesn’t just check boxes… it creates emotion, urgency, and that unmistakable “we need this one” reaction the moment your buyers walk through the door. From the very first glance, the curb appeal sets the stage with a warm, polished presence that immediately stands out from the competition. Inside, you’re welcomed by a light-filled, open-concept layout that feels expansive yet comfortable — the perfect balance of elegance and livability. Every space has been thoughtfully designed to flow effortlessly, creating an atmosphere that feels both elevated and inviting. The heart of the home is a beautifully positioned kitchen that seamlessly connects to the main living areas, making it ideal for entertaining, gathering, and everyday life. Whether hosting friends or enjoying a quiet night in, this home delivers the versatility today’s buyers demand. Generously sized living spaces and bedrooms provide comfort, privacy, and flexibility, while the overall layout offers a sense of ease and functionality that appeals to a broad range of buyers — from families to professionals to those simply looking to upgrade their lifestyle. Step outside and experience your own private Florida escape — a backyard setting that invites relaxation, weekend gatherings, and year-round enjoyment. It’s the kind of outdoor space that sells the lifestyle just as much as the home itself. Perfectly positioned in a highly desirable Maitland location, this property offers unbeatable convenience to top-rated dining, shopping, entertainment, and major highways — putting everything Central Florida has to offer right at your fingertips. This is not just another listing — it’s a high-impact, high-demand opportunity that shows beautifully, lives effortlessly, and is primed to sell quickly. Homes with this combination of appeal, location, and lifestyle don’t sit… they move. Bring your buyers with confidence — this is the one they’ve been waiting for.
Listing is courtesy of: THE FLORIDA PROPERTY SHOP SALE (352-346-7857)
Listing Agent: Anthony Scaraggi (516-749-6675)
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