Location: Maitland
Keyword(s): Lockhart Middle
Keyword(s) Middle School: Lockhart Middle
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1375 LAKE SHADOW CIR #11103, MAITLAND, FL 32751
$199,00025 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,714
Elementary School: Lake Sybelia Elem
High School: Edgewater High
Tax Year: 2025
Middle School: Lockhart Middle
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)
2154 FENNELL ST, MAITLAND, FL 32751
$420,00018 Days on yellowkey MLS ID: O6406585
REDUCED by $10,000 (2.3%) on 05/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1642 Built: 1997Monthly Fee: $18 Tax: $1,809 (2025)Community: WinfieldSingle Family
Taxes:$1,809
Remarks: Welcome to this meticulously maintained, one-owner home on a quiet corner lot bordering Fennell Park in Winfield. This 3-bedroom, 2-bath split floor plan features a freshly painted interior and new luxury vinyl plank flooring throughout the main areas. Recent upgrades include a 2021 HVAC for peace of mind going into summer. Relax in the oversized family room or retreat to the private primary suite with access to the back patio. Step through sliding glass doors to a fully fenced backyard oasis, complete with mature landscaping and a custom outdoor kitchen featuring granite counters and a built-in grill—perfect for hosting. Located in a family-friendly community with a low HOA, you'll enjoy top-rated schools and a prime location near the Maitland Business Center and Downtown Orlando. This home is situated near shopping, dining, entertainment, and key Central Florida roadways. Tranquility meets total convenience; schedule your private showing today!
Listing is courtesy of: PARK PLACE REALTY ASSOCIATES (407-878-0607)
Listing Agent: Barrett Espinola (407-617-3189)
1927 LEGACY COVE DR #1927, MAITLAND, FL 32751
$215,00012 Days on yellowkey MLS ID: O6409051
0 Days Off yellowkey (back on 5/27/2026)
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. 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 (407-977-7600)
Listing Agent: Kristin Duncan (407-274-5911)
1776 BOBTAIL DR, MAITLAND, FL 32751
$519,99953 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)
2150 TORTOISE SHELL DR, MAITLAND, FL 32751
$429,90039 Days on yellowkey MLS ID: O6392895
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: One or more photo(s) has been 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)
2837 SHADOW VIEW CIR #2837, MAITLAND, FL 32751
$225,000103 Days on yellowkey MLS ID: O6382993
3 Days Off yellowkey (back on 5/16/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1280 Built: 2000 Tax: $3,600 (2025)Community: Visconti EastCondo
Taxes:$3,600
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. LIMITED TIME ONLY THROUGH MAY 11! Seller is offering a $5,000 contribution towards buyer’s closing costs. Move-In Ready Maitland Condo with Rare 2-Car Garage & Flexible Work-From-Home Layout Welcome to this beautifully updated three-level condo in a gated Maitland community—offering the space, flexibility, and low-maintenance lifestyle today’s buyers are looking for. This 2-bedroom, 2-bath home features a versatile office/flex room, ideal for working from home, a guest space, gym, or creative studio. Soaring ceilings, abundant natural light, and a smart multi-level layout create a bright and open feel throughout. Recent 2026 upgrades include fresh interior paint, brand-new carpet, updated bathrooms, new window blinds, and stainless steel appliances (refrigerator 2024), along with a full-size in-unit washer and dryer—making this home truly move-in ready. One of the standout features is the rare 2-car garage—hard to find in this area—offering added convenience and storage. Enjoy a low-maintenance lifestyle with HOA coverage that includes exterior maintenance, landscaping, valet trash, water, sewer, and pest control. The community offers resort-style amenities including two pools, fitness center, clubhouse, tennis and basketball courts, and playground. Ideally located just minutes from I-4, shopping, dining, and daily conveniences, this home offers both comfort and connectivity. Home includes a warranty and is available for immediate occupancy.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Nilufer Rohleder (407-962-7494)
2040 BOBTAIL DR, MAITLAND, FL 32751
$370,00013 Days on yellowkey MLS ID: O6408698
0 Days Off yellowkey (back on 5/22/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1382 Built: 1998Monthly Fee: $18 Tax: $3,097 (2025)Community: Winfield Ut 1Single Family
Taxes:$3,097
Remarks: Cute home alert! Finally — an updated, move-in ready home in an amazing Maitland location priced under $400K! Imagine hosting friends and family in the spacious separate dining room, gathering around the oversized kitchen island while dinner cooks, and spending evenings relaxing on the screened patio and playing safely in the fully fenced backyard. Tucked inside the quiet Winfield community with a low HOA, this beautifully maintained 3-bedroom, 2-bath home with split floor plan is an excellent balance of modern style and everyday functionality. Step inside to discover a bright, open-concept layout featuring vaulted ceilings, recessed lighting, and consistent hard-surface flooring throughout. The spacious living area flows seamlessly into the fully updated gourmet kitchen, complete with beautiful countertops, 42” solid wood soft-close cabinetry, and high-end stainless steel appliances — creating a welcoming space in the heart of your home. This split floor plan offers both privacy and flexibility, with an expansive primary suite featuring a walk-in closet with custom built-ins and a beautifully updated bathroom with dual vanities, a relaxing garden tub, and separate shower. On the opposite side of the home, two additional bedrooms are ideal for a nursery, guest room, playroom, or home office. The living space flows to a covered and screened patio, creating a perfect space for year-round indoor-outdoor living. Whether you’re enjoying slow mornings with coffee, hosting weekend get-togethers, or relaxing after work, the fully fenced backyard offers both comfort and privacy. Fresh landscaping, mature shade trees, and the perfect mix of filtered sunlight and greenery give the outdoor space a calm, inviting feel, while the tiled flooring adds a clean, polished touch that’s both stylish and low maintenance. ROOF: 2018
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Michael Wathen (407-205-7660)
2134 KORAT LN, MAITLAND, FL 32751
$364,50015 Days on yellowkey MLS ID: O6401286
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1642 Built: 1998Monthly Fee: $18 Tax: $5,340 (2025)Community: WinfieldSingle Family
Taxes:$5,340
Remarks: All highest and best offers due by 10:00 AM EST on 5/21/26. Welcome home! This inviting three-bedroom, two-bathroom residence in the heart of Maitland combines everyday convenience with a comfortable living environment ready for years of memories. As you step inside, vaulted ceilings draw the eye upward, creating a sense of openness throughout the interior, while its functional design delivers multiple living areas, a spacious primary suite, and flexible secondary bedrooms, perfect for life’s ever-changing needs. The thoughtful floor plan boasts a natural flow between living areas, bedrooms, and the screened patio, creating a residence that feels both spacious and intimate; ideal for day-to-day life and entertaining guests. The new HVAC System, new Water Heater, and fresh exterior paint add to the list of positives, allowing for peace of mind for years to come. Beyond the interior, a partially covered screened lanai extends the living space, offering a sheltered retreat, with a fenced backyard to maximize privacy. Location-wise, this property places you in the heart of the action near vibrant shopping, dining, and entertainment options. Within one mile, you will find multiple restaurants, shopping plazas, and the Orlando Sportsplex/Ice Den, providing everyday needs at your doorstep. For days when you want to venture further, you are less than five miles from the Winter Park Village, Altamonte Mall, College Park, medical services, multiple golf courses and sports fields, various parks and nature trails, and immediate highway access, which allows for a straightforward journey to anywhere in Central Florida and beyond. Schedule your private showing today and experience the convenience of this move-in-ready property firsthand.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY (407-203-0007)
Listing Agent: Joseph Doher (407-203-0007)
1275 LAKE SHADOW CIR #13206, MAITLAND, FL 32751
$145,500103 Days on yellowkey MLS ID: O6383068
REDUCED by $12,000 (7.6%) on 05/18/2026
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: One or more photo(s) has been virtually staged. Water views, brand-new mechanicals, and the best price in the building. This 1-bedroom, 1-bath condo at Visconti is offered at $9,000 less than the only comparable unit in the same building — and comes with a new Goodman 2-ton, 14.3 SEER HVAC system (2025), new water heater with expansion tank (2026), and a refreshed kitchen featuring new shaker cabinets (2025), representing over $15,000 in recent improvements. Enjoy peaceful pond views from your private balcony and bedroom, accessed through a large sliding glass door off the open living area, which features built-in shelving and a bright, functional layout. A separate laundry room adds everyday convenience. Residents enjoy two resort-style pools, a fitness center, a clubhouse, and sports courts in a gated community where HOA fees include trash, water, and sewer. Minutes to I-4 with easy access to downtown Orlando, Winter Park, Walt Disney World, Universal, and Orlando International Airport. Ideal for first-time buyers, those right-sizing, or investors seeking a low-maintenance rental. 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)
1010 WINDERLEY PL #127, MAITLAND, FL 32751
$332,50062 Days on yellowkey MLS ID: O6395028
5 Days Off yellowkey (back on 5/15/2026)
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: Under contract-accepting backup offers. 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)
1175 LAKE SHADOW CIR #4308, MAITLAND, FL 32751
$234,000193 Days on yellowkey MLS ID: O6361097
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1372 Built: 2000 Tax: $3,355 (2024)Community: Visconti WestSpa: NoCondo
Taxes:$3,355
Remarks: Experience true resort-style living at its finest in this lovely 4-bedroom, 2-bath condominium in the beautiful, gated community Visconti West. As you enter the home, you are welcomed by an open and spacious floor plan filled with abundant natural light, vaulted ceilings and decorative cutouts. Enjoy a split-plan layout that offers comfort and privacy for family and guests. The kitchen features a breakfast bar, track lighting, kitchen appliances, pantry closet and a separate inside laundry space for convenience. Step out onto your private balcony from the main living space and take in the breathtaking water views, perfectly positioned for stunning sunsets – your own peaceful retreat at the end of the day. The primary bedroom offers stunning water views, a private bath and walk in closet. Guest bedrooms are spacious and are light and bright. This highly sought-after community offers exceptional amenities, including a resort-style lakefront pool, dock, walking trails with lake views, state-of-the-art fitness center, clubhouse, tennis & pickleball court, basketball court, and a recreational playground—providing something for everyone to enjoy. It is conveniently located in the heart of Maitland, close to Maitland Ballfield Complex, Genesis Sporting Complex and minutes from downtown Winter Park. Easy access to all major highways, restaurants, retail and shopping. This home is perfect for those who are seeking a low-maintenance lifestyle. Schedule your showing today.
Listing Agent: Julie Ruh (407-587-9654)
1000 WINDERLEY PL #239, MAITLAND, FL 32751
$299,00061 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)
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