Location: Maitland , 32751
Do Not Show Listings
908 VERSAILLES CIR, MAITLAND, FL 32751
$899,00037 Days on yellowkey MLS ID: O6413200
2 Days Off yellowkey (back on 6/17/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2151 Built: 1979 Tax: $11,362 (2025)Community: VersaillesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$11,362
Elementary School: Lake Sybelia Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Maitland Middle
Remarks: Under contract-accepting backup offers. Ideally in one of Maitland’s desired neighborhoods, Versailles, this fully renovated home blends timeless architecture with modern comfort. With sun-filled interiors, an open-concept layout, a serene primary suite and freshly landscaped grounds, every detail supports effortless living. This three-bed, two-bath home stretches over 2,151 square feet and is situated on 0.29 of an acre. This classic ranch style offers a split bedroom plan with endless function. A gracious foyer welcomes you into this serene space with blonde oak flooring, limewash accent walls, a vaulted ceiling with wood beam accents, fresh neutral tones, designer fixtures and ambient lighting that softens the spaces. This home features formal dining and a flex space that could be a fourth bedroom or office, offering many layout choices. The combined kitchen and living room showcases a wood-burning fireplace with a fluted marble surround as the focal point. The kitchen combines crisp, clean-lined cabinets and warm-wood-toned floor-to-ceiling storage cabinets finished with brushed-gold hardware. A waterfall center island with quartz counters that continue up the backsplash for a stylish design. Clear view sliders open to a covered porch with a tongue and groove ceiling feature and is part of a screened pool, making entertaining a breeze. Recently installed turf grass for ease of maintenance and keeps it all looking very fresh. The pool was recently refinished and a side-yard sauna rounds out this oasis. The primary suite is a private retreat with an oversized walk-in shower with beautiful vertical Zellige tile. Dual vanities with custom arched mirrors, sconce lighting and porcelain-marble floors add to the space. Built-in linen closets and dual bedroom closets make organization simple. Additional highlights include both baths completely renovated, new kitchen appliances (LG/GE stainless steel) induction range, new interior doors and hardware, new ceiling fans, new Pella front doors and Impervia slider doors across the back of the home, new Pella front windows, a new Hass garage door (2025), the whole yard professionally designed and landscaped (2026), a sauna (2024), a roof (approximately 2018) and a water heater (2023). This neighborhood enjoys a community lake lot with access to Lake Minnehaha, part of the Winter Park lake chain. Strategic location close to major roadways, short distance to the Sunrail and close to all amenities that make Maitland special. Zoned for some of the best Orange County schools: Lake Sybelia, Maitland Middle and Winter Park High, a nationally renowned school for its International Baccalaureate Program.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Alison Mosley (407-304-6458)
1781 TONTO TRL, MAITLAND, FL 32751
$600,00030 Days on yellowkey MLS ID: O6414036
1 Days Off yellowkey (back on 6/17/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1880 Built: 1968Monthly Fee: $17 Tax: $2,220 (2025)Community: Dommerich Estates 1St AddSingle Family
Taxes:$2,220
Elementary School: Dommerich Elem
Remarks: Under contract-accepting backup offers. Welcome to 1781 Tonto Trail, a 4-bedroom home in one of Maitland's most desirable neighborhoods, offering just under 1,900 square feet of living space, a split bedroom floor plan, and access to the Winter Park Chain of Lakes. Located on a corner lot just under a quarter acre, this move-in ready residence combines functionality, comfort, and an exceptional Maitland location. Inside, you'll find a formal living room and formal dining room that provide flexible spaces for entertaining, working from home, or everyday living. The spacious family room serves as a central gathering area and connects seamlessly to the home's thoughtful layout. The private primary suite features an ensuite bathroom and double closets, creating a comfortable retreat. Bedrooms two and three offer large walk-in closets, providing abundant storage and flexibility for family, guests, or home office needs. The split bedroom design enhances privacy while maintaining a practical flow throughout the home. Residents of Dommerich Estates enjoy access to highly regarded schools including Dommerich Elementary, Maitland Middle School, and Winter Park High School. A voluntary low-cost HOA provides access to a private boat ramp on the Winter Park Chain of Lakes, creating opportunities for boating, fishing, paddleboarding, and waterfront recreation. The location places you short distance to the Maitland Community Park, Maitland Social, and Maitland City Centre, offering convenient access to local dining, recreation, events, and community amenities. Whether you're looking for more space, access to top-rated schools, or the lifestyle benefits of a lake-access community, this 4-bed home in Dommerich Estates delivers a rare opportunity to enjoy one of Maitland's most established and sought-after neighborhoods.
Listing is courtesy of: EXP REALTY LLC (407-641-2808)
Listing Agent: Todd Schroth, Pa (407-641-2808)
204 QUAYSIDE CIR #201, MAITLAND, FL 32751
$467,00086 Days on yellowkey MLS ID: O6394791
REDUCED by $15,000 (3.1%) on 06/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1270 Built: 1984 Tax: $6,566 (2025)Community: Moorings On Lake Maitland CondoCondo
Taxes:$6,566
Remarks: Updated 2 bedroom 2 bathroom located on the second floor of sought after Moorings Lakefront Community with spectacular views of Lake Maitland of the Winter Park Chain of Lakes. The condo offers a large screened-in balcony overlooking Lake Maitland. The open floorpan offers a split plan with a generous size master retreat with a private door to the balcony and a secondary ensuite. The updated spacious kitchen features stainless steel appliances and a breakfast nook situated in a bay window. The dining living room combo is very spacious making it perfect for relaxing or entertaining. The condo offers washer and dryer in the unit as well as a private storage closet on the same floor just across the hall. The Moorings Lakefront community offers an amazing recently updated pool and spa area along a large clubhouse. Whether you're looking for a primary residence or a low-maintenance lakefront retreat, this condo and community offers an amazing combination of comfort and convenience.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Angel Reyes (407-697-3313)
1400 LAKE SHADOW CIR #10103, MAITLAND, FL 32751
$155,00086 Days on yellowkey MLS ID: S5147962
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 672 Built: 2000 Tax: $2,238 (2025)Community: Visconti West CondoCondo
Taxes:$2,238
Elementary School: None
High School: None
Middle School: None
Remarks: Nice one-bedroom unit on the ground floor featuring brand-new laminate countertops in both the kitchen and bathroom, along with stainless steel appliances. Located in a gated, resort-style community offering top amenities including a pool, fitness center, tennis and basketball courts, playground, clubroom, and car wash. All in an excellent Maitland location!
Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)
Listing Agent: Gilgra Valduz Sandoval (321-310-3259)
1106 CHARMING ST, MAITLAND, FL 32751
$490,00038 Days on yellowkey MLS ID: O6413431
0 Days Off yellowkey (back on 6/15/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1870 Built: 2006Monthly Fee: $520 Tax: $6,232 (2025)Community: Enclave/Maitland A-FSpa: NoTownhouse
Taxes:$6,232
High School: Edgewater High
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained lakefront townhome in a highly desirable gated community in Maitland with almost 1900 square feet of thoughtfully designed living space. This 3-bedroom, 2.5-bath residence combines comfort, functionality, and picturesque lake views. Enjoy serene views of Lake Charity from the charming front porch, formal dining room, and two upstairs bedrooms. Soaring ceilings and abundant natural light create an airy, inviting atmosphere throughout the home. The spacious open-concept kitchen overlooks the family room and features ample counter seating for barstools, generous cabinetry, and a nice pantry. A private courtyard provides a welcoming outdoor retreat and leads to the oversized 2-car garage with abundant attic storage above. The separate dining room offers a perfect setting for entertaining while enjoying tranquil lake views. A convenient guest bathroom is located on the first floor as well. Upstairs, the massive Primary suite serves as a true retreat, featuring a custom walk-in closet and a spa-inspired en-suite bath with a soaking tub, separate shower, and dual vanities. Two additional bedrooms have stunning views of the lake. One includes a Murphy bed with beautiful built-ins and a custom closet. Another full bath, and a spacious laundry room with plenty of storage complete the second floor. The reasonable HOA fee includes use of the sparkling pool, the secure gate, all landscaping, all maintenance of the exterior of this townhome including the roof, repairs, and paint, and high-speed internet with cable TV, through Spectrum. Offering exceptional space, beautiful water views, and a sought-after gated location, this townhome is the ideal place to call home. *A complimentary complete one-year Home Warranty is provided for extra peace of mind. (A recent Lender's appraisal is also available.)
Listing Agent: Donna Bryant (407-509-8047)
2401 LEGACY LAKE DR #2401, MAITLAND, FL 32751
$355,00038 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)
1191 WILLOWBROOK TRL, MAITLAND, FL 32751
$765,00045 Days on yellowkey MLS ID: O6410813
0 Days Off yellowkey (back on 6/11/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2287 Built: 1966 Tax: $4,636 (2025)Community: Maitland WoodsSpa: NoSingle Family
Taxes:$4,636
Remarks: Under contract-accepting backup offers. Don't miss this rare opportunity to purchase your dream home in the established Maitland Woods neighborhood. This charming 4-bedroom, 2-bath home has been meticulously maintained and contains premium finishes throughout. The open floor plan includes a large family/great room, dining room, and an enclosed patio, perfect for entertaining. The updated kitchen features a handmade subway tile backsplash, quartzite countertops, stainless steel appliances, a coffee bar, and a versatile indoor laundry/ second office or crafting room. The primary bathroom has been completely renovated, with a double-sink marble vanity, large shower, and walk-in closet. The second full bathroom is centrally located, with additional access to the enclosed patio, making it also an optional (future) pool bath. This home includes a large (0.29-acre) fully fenced backyard, ideal for children and/or pets to play. Some notable exterior improvements include: a new front brick patio, a new firepit area for entertaining, a vegetable/flower garden and beautiful landscaping. Maitland Woods is conveniently located near I-4, making commuting to either downtown Orlando or Lake Mary a breeze. In addition, the home is within walking distance to Orangewood Christian School, Lake Sybelia Elementary, the shops and restaurants of downtown Maitland (home of a weekly farmer’s market), city events at Lake Lily, and Lake Sybelia’s very own Homer Hough Park. Homer Hough Park is the area’s best-kept secret, with a playground, fishing, and pavilions for family events. This home will not last, call to schedule your private showing today! Age of major components includes water heater 2022; NEW front patio 2026; roof 2016; HVAC 2024/2025; Replumb CPVC 2020; inside and outside electrical panels 2025; and double-pane windows 2016-2023 – with lifetime warranty.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Marti Hornell (407-222-1443)
747 N LAKE SYBELIA DR, MAITLAND, FL 32751
$3,895,00061 Days on yellowkey MLS ID: O6406879
5 Days Off yellowkey (back on 6/9/2026)
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 5347 Built: 2023 Tax: $23,099 (2025)Community: Sybelia Shores Second AddSpa: YesSingle Family
Taxes:$23,099
Remarks: Under contract-accepting backup offers. Welcome to 747 N Lake Sybelia Drive, an extraordinary lakefront estate gracefully positioned along the desired northern shoreline of beautiful Lake Sybelia. Completed in late 2023, this breathtaking California Coastal-inspired residence spans 4,755 square feet on an expansive 0.76-acre homesite, blending timeless architecture with refined finishes to create a lifestyle defined by elegance, comfort and effortless lakefront living. Ideally situated on a gently sloping lot, the home captures stunning elevated views of the water, offering a rare sense of privacy, tranquility and perspective. Thoughtfully designed interiors are filled with natural light and crafted for everyday living and exceptional entertaining. The main level showcases a beautifully appointed chef’s kitchen anchored by an oversized island and complemented by a spacious walk-in butler’s pantry. Open-concept dining and living spaces are framed by picturesque lake views, while the expansive great room seamlessly connects indoor and outdoor living. A private office, guest suite and dedicated pool bath complete the first floor. Upstairs, a versatile loft and homework nook provide flexible living space, while two en-suite bedrooms and a serene primary retreat offer exceptional comfort and privacy. The luxurious primary suite and one secondary bedroom open to a spacious lakeside balcony, an idyllic place to enjoy morning coffee, evening sunsets and sweeping water views. Exceptional outdoor living spaces surround the home. A welcoming covered front porch offers the perfect vantage point to enjoy lake views and watch boating activity, while the expansive rear covered lanai is designed for year-round entertaining with a summer kitchen and generous space for lounging and dining. Overlooking the beautifully landscaped backyard, complete with bamboo-lined fencing for privacy, is a sparkling saltwater pool and spa by Titan Pools, thoughtfully designed for resort-style enjoyment and capable of both gas and electric heating. Uniquely embraced by water and recreation, the home enjoys tranquil lake vistas to the south and the stunning pool retreat to the north. The waterfront experience is elevated by a newly constructed composite dock with a heavy-duty dual-motor lift, while a thoughtfully designed shell-base boat ramp provides seamless, eco-conscious access for launching watercraft directly from your property. Adding even more versatility, a 500+ square-foot unfinished bonus room above the garage offers incredible potential for customization, ideal for a media room, guest retreat, fitness studio or creative space. Plumbing has been extended for a future bath or bar, and the space is currently enjoyed as a golf simulator. Car enthusiasts will appreciate the impressive four-car tandem garage featuring soaring 15-foot ceilings designed to accommodate vehicle lifts, premium wall-mounted jackshaft openers for maximum overhead clearance and a separate side-access bay ideal for golf cart storage. Engineered for longevity as much as luxury, the home features an extensive stormwater drainage system with hard-piped gutters designed to protect the land and prevent erosion. Ideally located, enjoy a short visit or golf cart ride to Maitland City Centre and Homer Hough Park at Sybelia Point, while the shopping and dining of Park Avenue are just minutes away. Convenient access to Interstate 4 and express lanes ensures effortless travel throughout the greater Orlando area.
Listing Agent: Mick Night (407-629-4446)
1393 BENEVOLENT ST, MAITLAND, FL 32751
$379,00087 Days on yellowkey MLS ID: O6399560
0 Days Off yellowkey (back on 6/8/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1674 Built: 2005Monthly Fee: $520 Tax: $3,322 (2025)Community: Enclave/Maitland A-FTownhouse
Taxes:$3,322
Remarks: This beautiful Maitland Florida town home feels like living in a gated resort! 3 bedrooms, 2 1/2 baths, plus garage and loaded with upgrades including hardwood floors on both levels, crown molding, tall wood cabinets, stone counters and so much more. Welcoming entry foyer with half bath, kitchen with island sink, large breakfast bar, stainless appliances, granite counters and custom backsplash. Inviting living room and dining area offer plenty of space for entertaining, french door opens to private covered porch which overlooks the rear yard. Upstairs the ensuite primary bedroom has a walk-in closet, great covered balcony area and a dual sink bathroom with glass enclosed shower. Additional 2 bedrooms in the front of the upstairs share a hall bath and laundry closet with washer and dryer included. Montacino is a gated European feeling award winning community with amazing pool area, lake frontage and a convenient location to shopping and i4. This townhouse has a quiet location within the community offering privacy in the back area. All exterior maintenance is included (roof and paint too)! HOA dues include new fiber with internet and channel package and all Montacino amenities.
Listing is courtesy of: RENCHER REALTY GROUP (321-325-2040)
Listing Agent: Daniel Rencher (407-279-1946)
1140 S ORLANDO AVE #I14, MAITLAND, FL 32751
$325,00049 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
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 Agent: Michele Ostrander (407-435-3863)
204 QUAYSIDE CIR #304, MAITLAND, FL 32751
$395,000295 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)
480 BANYON TREE CIR #100, MAITLAND, FL 32751
$106,000468 Days on yellowkey MLS ID: O6294907
REDUCED by $13,000 (10.9%) on 05/18/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 759 Built: 1973 Tax: $1,617 (2024)Community: Carrington Park A CondoCondo
Taxes:$1,617
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: South Seminole Middle
Remarks: Spacious 1/1 Carrington Park Condo; New community. Great amenities, pools, gym & club house. Close to Winter Park, Downtown Orlando & schools. The unit is in excellent condition. Floor and kitchen renovated. New air conditioning. Rented until Feb-28-2027 at $1000
Listing is courtesy of: MIAMI TANGO INVESTMENTS REALTY (786-464-8803)
Listing Agent: Moses Nae (407-499-0240)
1010 GREGORY DR, MAITLAND, FL 32751
$520,00046 Days on yellowkey MLS ID: O6411422
0 Days Off yellowkey (back on 6/1/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2227 Built: 1969 Tax: $4,288 (2025)Community: Druid Hills Estates 1St AddSpa: NoSingle Family
Taxes:$4,288
Elementary School: Lake Orienta Elementary
High School: Lyman High
Middle School: Milwee Middle
Remarks: Nestled in the heart of highly desirable Maitland, this spacious 4-bedroom, 2-bath pool home offers the perfect blend of location, functionality, and outdoor living on an oversized .28-acre lot with more than 12,000 square feet of property. Surrounded by mature trees and established neighborhoods, this prime location places you just minutes from Downtown Maitland, Historic Winter Park, Downtown Orlando, world-class shopping, dining, entertainment, and Central Florida’s renowned attractions. Maitland is loved for its charming restaurants, weekend farmer’s market, beautiful lakes, and scenic tree-lined streets, all while bordering some of the most prestigious real estate in Central Florida.The backyard is truly the showstopper of this property, featuring a sparkling open pool, beautiful vinyl fencing, and an expansive yard that is far larger than many homes in the area. Recent landscaping enhancements include a hardscaped entertaining space and decorative stone half wall, creating the perfect setting for relaxing, hosting guests, or enjoying Florida outdoor living under the shade of the beautiful oak tree.Inside, the home features a desirable split-bedroom floor plan with formal living and dining rooms, plus a spacious family room offering plenty of flexibility for everyday living and entertaining. The galley-style kitchen is equipped with granite countertops and overlooks the living areas for easy functionality. Attractive laminate wood flooring and tile flow throughout the home, while all bedrooms have been updated with new ceiling fans. Additional improvements include electrical upgrades, new exterior doors, a new roof installed in 2020, and added attic insulation for enhanced energy efficiency. Built with sturdy concrete block construction, this home offers lasting durability and peace of mind. The indoor laundry room includes the washer and dryer for added convenience. This is a rare opportunity to own a pool home with a large backyard in one of Central Florida’s most established and desirable locations.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Kelly Hildebrand (407-310-5035)
1375 LAKE SHADOW CIR #11103, MAITLAND, FL 32751
$199,00066 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
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)
1166 N LAKE SYBELIA, MAITLAND, FL 32751
$3,100,00045 Days on yellowkey MLS ID: O6411525
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 5355 Built: 1998 Tax: $11,303 (2025)Community: Lake Sybelia ShoresSingle Family
Taxes:$11,303
Remarks: Welcome to luxury lakefront living at its absolute finest in the heart of Maitland, Florida. Nestled along the pristine shores of Lake Sybelia, this extraordinary three-story estate offers an unparalleled combination of elegance, comfort, and breathtaking waterfront views. Boasting 5,355 square feet of thoughtfully designed living space, this stunning residence features six spacious bedrooms, four and a half bathrooms, and an open-concept floor plan perfectly crafted for both entertaining and everyday living. Expansive walls of glass fill the home with natural light while showcasing panoramic lake views from nearly every room. The main living area seamlessly connects the gourmet kitchen, dining room, living room, and family room, all overlooking the sparkling waters of skiable Lake Sybelia. Designed with indoor-outdoor living in mind, each floor features a balcony spanning the entire width of the rear of the home, creating multiple spaces to relax and enjoy Florida’s spectacular sunsets. Step outside to your private resort-style oasis complete with a gorgeous pool, lush landscaping, and direct lake access with your own private boat dock and lift, perfect for boating, skiing, and waterfront recreation year-round. The upstairs retreat is anchored by an impressive primary suite featuring serene lake views and private balcony access. The upper level also includes a dedicated private office, ideal for working from home while enjoying stunning lakefront views. Two additional bedrooms share a beautifully designed Jack-and-Jill bathroom, while another flexible bedroom space can easily serve as a nursery, fitness room, or additional guest bedroom. Every level of the home has been carefully designed to maximize comfort, privacy, and functionality while maintaining a sophisticated and timeless aesthetic throughout. The lower level offers endless entertainment possibilities with a spacious game room, a full movie theatre, an additional guest bedroom, and a full bathroom ideal for visitors or multi-generational living. Completing this exceptional property is a beautiful temperature controlled wine cellar holding almost 2,000 wine bottles, a two-car garage with additional storage space, a large home generator, and countless luxury details throughout. This one-of-a-kind Lake Sybelia estate delivers the perfect balance of upscale living, modern convenience, and the ultimate waterfront lifestyle in one of Central Florida’s most desirable locations.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Joseph Sipp (407-820-7016)
1230 HOLLYRIDGE TRL, MAITLAND, FL 32751
$534,900123 Days on yellowkey MLS ID: O6389346
0 Days Off yellowkey (back on 5/22/2026)
REDUCED by $40,000 (7.0%) on 05/05/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1641 Built: 1983 Tax: $1,955 (2024)Community: Dommerich Woods Unit 2Single Family
Taxes:$1,955
Remarks: Dommerich Woods gem! Tucked away on a cul-de-sac street in one of Maitland’s most sought-after neighborhoods, this beautifully updated 3-bedroom, 2-bath block home is the one you’ve been waiting for. Move-in ready and genuinely charming from the moment you walk in. The open floor plan feels airy and welcoming, with vaulted ceilings and natural light pouring through every room. The living room centers around a classic brick fireplace that anchors the space perfectly, while the kitchen is a true standout-quartz countertops, stainless appliances, 40-inch soft-close shaker cabinets and a built-in pantry. The layout flows effortlessly between living, dining and family spaces, making it as functional as it is inviting. The split bedroom layout offers great privacy for everyone. The primary suite is a real retreat- vaulted ceiling, spacious walk-in closet and a completely redone en-suite bath with a lovely garden window. Both bathrooms have been given a fresh, modern look that feels clean and polished. The updates list is long and impressive: newer LVP flooring throughout, AC (2022), water heater (2023), roof replaced in 2016, replumbed in 2008, newer paint inside and out, newer light fixtures and ceiling fans. Laundry is indoors and connects right to the two-car garage-a detail you’ll appreciate daily. Out back, the expansive yard is a genuine sanctuary. Mature trees, lush landscaping and total privacy make it the kind of space you’ll actually use. A large shed with 50-amp power is ready for a workshop, hobby space or serious storage-and with NO HOA, bring the toys too! Just minutes from Kewannee Park, the Seminole bike trail and easy access to major roads and local shops and restaurants. It’s a rare find in a neighborhood where homeowners rarely leave. Come take a look.
Listing is courtesy of: BOWERBIRD REALTY (407-716-0239)
Listing Agent: Stephanie Doucette (407-716-0239)
616 VILLA CIR #536, MAITLAND, FL 32751
$252,00050 Days on yellowkey MLS ID: O6410478
0 Days Off yellowkey (back on 5/28/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1256 Built: 1979 Tax: $2,360 (2025)Community: Park Lake Villas CondoCondo
Taxes:$2,360
Remarks: 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 (407-442-0299)
Listing Agent: Jessica Loomis (407-953-9893)
1776 BOBTAIL DR, MAITLAND, FL 32751
$519,99994 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)
1111 AUDUBON WAY, MAITLAND, FL 32751
$1,825,000139 Days on yellowkey MLS ID: O6382602
REDUCED by $150,000 (7.6%) on 05/27/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3754 Built: 1985 Tax: $13,827 (2025)Community: Maitland CoveSpa: NoSingle Family
Taxes:$13,827
Remarks: Welcome to a rare opportunity on the shores of Lake Sybelia, one of Maitland’s most desirable recreational lakes. This custom, one-owner home offers 3,754 square feet of thoughtfully designed living space that has been well-maintained with potential for cosmetic enhancements. A brick-paved horseshoe driveway and inviting front porch set the tone. Inside, rich wood floors, vaulted wood ceilings in the living and family rooms, two fireplaces, and custom built-ins showcase quality rarely found today. The spacious layout features four bedrooms and 3.5 baths, including two primary suites ideal for multi-generational living. Generous walk-in closets and a blend of wood, tile, and carpet add comfort and function. A new A/C (Oct 2025) and a 6.5-year-old roof provide peace of mind. Living areas open to a bright rear sunroom with tranquil lake views. Whether you’re entertaining by the fire, enjoying coffee on the porch, or heading out onto the lake, this property delivers the Florida lifestyle at its finest.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Melissa Shipp (407-748-7163)
105 TANGELO CT, MAITLAND, FL 32751
$1,798,999220 Days on yellowkey MLS ID: O6364116
2 Days Off yellowkey (back on 5/25/2026)
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3203 Built: 2026 Tax: $6,909 (2024)Community: Hollieanna ShoresSpa: NoSingle Family
Taxes:$6,909
Remarks: Under contract-accepting backup offers. Under Construction. A masterpiece of luxury design by LUIH Luxury Homes, perfectly positioned in the prestigious neighborhood of Hollieanna Shores. As you arrive, a striking façade with an elegant arched entryway sets an unforgettable tone. Beyond the front door, soaring ceilings and designer finishes frame an expansive living room where glass sliders dissolve the boundary between indoor and outdoor living, creating a seamless transition to the lanai and resort-style backyard. At the heart of the home, a chef’s kitchen designed for both performance and beauty exceeds every expectation. Sleek quartz countertops, a full Thermador appliance suite, custom cabinetry, and an oversized walk-in pantry elevate culinary experiences to a professional standard. The primary suite is a private sanctuary intentionally crafted to evoke a spa-like retreat. A stunning bathroom showcases a freestanding tub, an expansive walk-in shower, dual vanities, and exquisite finishes, while a large boutique-style closet with custom built-ins ensures every piece has its place. The upstairs level offers a generous loft and beautifully appointed secondary bedrooms, creating the ideal separation of space for family or guests. Outdoor living is nothing short of extraordinary, featuring a huge covered lanai with a full summer kitchen overlooking a shimmering pool and expansive, fully fenced backyard. Situated in the sought-after Hollieanna Shores neighborhood, this residence places you moments from Maitland City Centre, local parks, the iconic Enzian Theatre, and Park Ave. shopping and dining. If you’re seeking a home that feels both artful and effortless, this is where elevated living becomes reality.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Christopher Christensen (407-312-8003)
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