Location: Maitland
Do Not Show Listings
766 TERRA PL, MAITLAND, FL 32751
$1,149,90041 Days on yellowkey MLS ID: O6411881
2 Days Off yellowkey (back on 6/19/2026)
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3040 Built: 1986 Tax: $8,473 (2025)Community: Terra PlaceSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,473
Elementary School: Lake Sybelia Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Maitland Middle
Remarks: Under contract-accepting backup offers. Virtually Staged. Private Pool Retreat with Two Primary Suites in Terra Place. Nestled in Terra Place, one of Maitland’s best-kept-secret neighborhoods, where every street ends in a cul-de-sac and a community park is just steps away, this custom one-story pool home offers space, privacy, and functionality—with no mandatory HOA. Soaring cathedral ceilings, including in the kitchen, and an abundance of windows fill the home with natural light. The open-concept layout flows seamlessly between the kitchen, dining, and living spaces, making everyday living and entertaining effortless. At the center of the home, the spacious kitchen offers casual bar-top seating, stainless steel appliances including a GAS RANGE, and an abundance of storage and workspace for effortless everyday living and entertaining. The kitchen also enjoys direct views of the backyard, covered patio, and saltwater pool, offering the kind of sight lines families love and making hosting feel effortless. With TWO PRIMARY SUITES and a highly-desirable THREE-WAY SPLIT floor plan allowing for maximum privacy, EACH BEDROOM features its own ENSUITE BATH. The spacious primary retreat offers a spa-like bath experience with dual sinks, private water closet, a large shower and soaking tub under a perfectly placed window. Large-format tile and wood flooring throughout (no carpet), generous room sizes, and thoughtfully designed spaces provide a clean, timeless backdrop ready for your personal style. This north-facing property provides soft, steady natural light year-round to enjoy whether you're under the covered patio, playing with the pets in the fully fenced backyard, or posting up on the sun shelf in the saltwater pool. An oversized two-car garage with an epoxy floor and mini split AC unit, NEW ROOF (2026) and SMART HOME (All Lutron light switches/fans, smart thermostats, door locks, alarm, and cameras) features add even more value and peace of mind. Boat Parking on the right side of the home through the double gate can accommodate all of your recreational vehicles. Enjoy walking or biking to Maitland Community Park, a 25-acre wooded park with tennis courts, basketball courts, playgrounds, trails, and pavilions. Conveniently located just minutes from downtown Maitland, Park Avenue in Winter Park, downtown Orlando, major roadways, area hospitals, and both executive and international airports. Zoned for highly regarded Lake Sybelia Elementary, Maitland Middle, and Winter Park High School, this exceptional home is a rare opportunity in one of Maitland’s most secluded and desirable neighborhoods. Call today for your private showing.
Listing is courtesy of: CREEGAN GROUP (407-622-1111)
Listing Agent: Chris Creegan (407-622-1111)
206 MOSELEY AVE, MAITLAND, FL 32751
$449,00037 Days on yellowkey MLS ID: O6414097
0 Days Off yellowkey (back on 6/18/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1838 Built: 2026 Tax: $3,007 (2025)Community: Pindar SubSingle Family
Taxes:$3,007
Elementary School: Hungerford Elem
High School: Edgewater High
Remarks: Under contract-accepting backup offers. Inside, the home opens into a bright and airy open-concept living space highlighted by high tray ceilings, recessed lighting, oversized glossy tile flooring, and an abundance of natural light. The seamless flow between the living, dining, and kitchen areas creates the perfect setting for both entertaining and everyday luxury living.
Listing is courtesy of: SYCHAR REALTY (407-921-0069)
Listing Agent: Brianna Grant (407-764-8436)
570 DOMMERICH DR, MAITLAND, FL 32751
$795,000136 Days on yellowkey MLS ID: O6377363
0 Days Off yellowkey (back on 6/17/2026)
REDUCED by $80,000 (9.1%) on 06/13/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2956 Built: 1963 Tax: $5,529 (2024)Community: Dommerich Estates 2Nd AddSpa: NoSingle Family
Taxes:$5,529
Elementary School: Dommerich Elem
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Virtually Staged. ONE OF A KIND for Dommerich Estates, this LAKE VIEW Home is designed for soaking in unforgettable sunsets and unwinding after a long day. Located directly across the street from the neighborhood lake lot, you will enjoy unobstructed views of the water, easy access to the boat ramp and fishing dock or launch your canoe or kayak for a peaceful paddle on the lake that also connects to the Winter Park Chain of Lakes! 4 generous bedrooms and 3 baths provide plenty of space for family and guests. Beautiful wood floors flow throughout and are complemented by crown molding for a classic touch. The spacious living room has a wood-burning fireplace and built-in cabinets to display all your treasures. It’s also large enough to be used for a combination living room/dining room and enjoy the lake views while you dine. The open kitchen and family room look out onto the screened patio and pool with a relaxing water feature. Feel secure during hurricane season with an installed and powerful Briggs and Stratton generator that will keep the power going to the kitchen, 4th bedroom and bath during the storm! Upgraded electrical system and the home has been replumbed for your peace of mind. Dommerich Estates has a strong sense of community and was designed and built around A rated schools so walking and biking to school is safe and easy. Social events at the lake lot provide a fun opportunity for neighbors to meet neighbors and there is a boardwalk that connects you to Maitland Park with playgrounds, tennis courts, walking trails and basketball courts. The City of Maitland is vibrant with a small-town feel providing events designed to foster connections among residents with multiple parks and downtown events and concerts! Don’t pass on this opportunity to own this rare, lake view home in one of the best neighborhoods in the area!
Listing is courtesy of: BHHS FLORIDA REALTY (407-406-5300)
Listing Agent: Shirley Welch (407-718-1450)
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
Taxes:$11,362
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
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)
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)
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)
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
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: South Seminole Middle
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)
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
Middle School: Lockhart Middle
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
Elementary School: None
High School: None
Middle School: None
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)
448 STONEWOOD LN, MAITLAND, FL 32751
$624,990138 Days on yellowkey MLS ID: O6385060
INCREASED by $19,990 (3.3%) on 05/04/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3308 Built: 1980Monthly Fee: $33 Tax: $11,256 (2025)Community: StonewoodSpa: NoSingle Family
Taxes:$11,256
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4-bedroom, 3-bathroom pool home offering the perfect blend of space, style, and location! From the moment you walk in, you’ll love the open layout and rich hardwood floors that create a warm and inviting atmosphere throughout. Designed for both everyday living and entertaining, this home features a dedicated office plus separate living, dining, and family rooms—giving everyone their own space while still feeling connected. The updated fireplace serves as a stunning focal point in the main living area, enhanced by natural light pouring in through the skylights. Recent upgrades provide added peace of mind and value, including a paver driveway and new gutters installed in 2019, full home re-pipe in 2021, air ducts sealed and new insulation added in 2021, a new pool pump and new AC compressor (one unit) in 2022, and new bedroom flooring in 2023.The kitchen is a true standout with 42” cabinetry, granite countertops, and newer stainless steel appliances, all overlooking the main living areas for seamless entertaining. A built-in wet bar adds the perfect touch for hosting gatherings and holiday celebrations. Retreat to the spacious primary suite and enjoy large closets throughout the home, providing ample storage for every lifestyle. Step outside to your private backyard oasis featuring a sparkling pool and expansive deck—ideal for relaxing weekends, outdoor dining, and Florida sunshine year-round. Located with easy access to Uptown Altamonte, I-4, 436, and Maitland Boulevard, this home places you just minutes from Lake Lily, Winter Park Village, Downtown Winter Park, and Cranes Roost—offering endless options for dining, shopping, parks, and entertainment. This home truly checks every box—space, updates, location, and a pool to top it all off! ????
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Dominick Florio (321-377-4045)
2642 BROOKSIDE CT, MAITLAND, FL 32751
$629,00073 Days on yellowkey MLS ID: O6403669
Bed: 5 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2360 Built: 1970 Tax: $5,909 (2025)Community: Forest Brook 3Rd SecSingle Family
Taxes:$5,909
Remarks: Indulge in the epitome of modern living with this fully renovated masterpiece! Boasting a thoughtfully designed split floor plan, 5 bedrooms, and 2 bathrooms, this home offers the perfect blend of space, style, and versatility. The heart of the home, the sleek kitchen, is a culinary haven equipped with stainless steel appliances, and ample counter space with upscale quartz countertops and storage. It's a canvas for your culinary creations. Whether you're a passionate collector or a lover of occasional indulgence, the built-in wine cooler transforms ordinary moments into extraordinary ones. Beyond elegant glass doors, unveil an expansive living room that is sure to captivate. Bathed in natural light, this grand space invites relaxation, entertainment, and cherished family moments. With 5 well-appointed bedrooms, there's ample space for everyone. The split floor plan ensures privacy and convenience for all members of the household. The master bedroom is a sanctuary of sophistication and comfort. With its spacious design and thoughtful layout, it provides an inviting escape from the world outside. The en-suite bathroom complements the master suite with its lavish features, double vanities, and a spa-like shower - experience the touch of rainfall from above and immerse yourself in the lap of luxury with the ceiling-mounted shower head. A dedicated bonus room adds an extra layer of versatility, it's ideal for a home office, playroom, or creative studio, the space adapts to your unique needs. Don't miss the chance to call this fully renovated gem your own. With its spacious layout, and modern finishes.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Giancarlo Chavez (312-869-1888)
987 BRIGHTWATER CIR, MAITLAND, FL 32751
$1,100,00079 Days on yellowkey MLS ID: O6401747
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3270 Built: 1996Monthly Fee: $395 Tax: $12,450 (2025)Community: Maitland ClubSpa: YesSingle Family
Taxes:$12,450
Remarks: Your dream home awaits. Welcome to this exquisitely Renovated 4/4 PLUS OFFICE PLUS BONUS ROOM POOL HOME. Located in the gorgeous guard gated enclave of Maitland Club. From the moment you enter, soaring ceilings and an elegant 3-way split floor plan create a sense of openness and refined comfort. At the heart of the home lies a beautiful updated kitchen, complete with a spacious center island, induction cooktop, and newer appliances - seamlessly flowing in to the sunlit breakfast nook and invitation family room, where a gas fireplace adds warmth and charm. All of these living spaces overlook a breathtaking outdoor retreat featuring a sparkling oversized swimming pool, perfect for both quiet relaxation and lively entertaining. Designed with versatility in mind this 3 way split plan has an upstairs bonus room with a full bath, - ideal as a playroom, home theater, exercise room or even a combination of spaces due to it's large size. Set on a generous one-third acre lot, the property offers ample room for outdoor enjoyment, from a potential playground to a thoughtfully designed lanai with dedicated areas for dining and lounging. Every corner of this home invites you to linger and enjoy. Ideally located near everything you love, this home offers easy access to premier grocery destinations, vibrant shopping and dining, major roadways, perfectly blending luxury with everyday convenience. Just minutes from Whole Foods, Trader Joe’s, Altamonte Mall, and the renowned shops and restaurants along Park Avenue in Winter Park, you’ll enjoy the best of Central Florida living right at your doorstep. Well-maintained home with A/C replaced in 2017. Interior upgrades completed in 2020, including a updated kitchen, newer appliances, new flooring, and three beautifully renovated bathrooms. No pool heater. Homes of this caliber do not last long.... come experience it for yourself.
Listing Agent: Gale Milgrim (407-443-9832)
360 LAKE SEMINARY CIR, MAITLAND, FL 32751
$4,999,000234 Days on yellowkey MLS ID: O6362152
Bed: 5 Bath: 7.0 Gar: 3 Liv Area Sq Ft: 6466 Built: 2026 Tax: $3,536 (2024)Community: FloridahavenSpa: YesSingle Family
Taxes:$3,536
Remarks: Pre-Construction. To be built. An extraordinary opportunity to claim one of Lake Seminary’s desired shorelines awaits. Masterfully envisioned by Heathrow Custom Homes, this newly built lakefront estate introduces a fresh standard of modern luxury for Maitland and Winter Park. Poised on an expansive 0.69-acre parcel, the residence spans nearly 6,500 square feet of impeccably curated living space, where sophisticated architecture and bespoke finishes harmonize with the tranquil beauty of the lake. A striking floating staircase framed by floor-to-ceiling glass offers a captivating first impression, while the grand entry reveals uninterrupted vistas of the pool terrace and shimmering water beyond. The chef’s kitchen, anchored by a remarkable 20-foot island, features premier appliances, exceptional storage and a concealed full-service scullery, creating an environment for hosting with grace and ease. The great room continues the home’s celebration of light and space with walls of glass that welcome breathtaking lake views at every turn. The primary suite is a serene retreat, showcasing a spa-inspired bath with floating vanities, a freestanding soaking tub, an expansive glass-enclosed shower and extravagant walk-in closets designed for the discerning owner. A secondary bedroom suite and oversized laundry enrich the main level, while an expansive lanai with an extraordinary summer kitchen invites effortless alfresco living, an experience only genuine lakefront living can provide. The second floor unfolds into a generous game room, complete with a wet bar and kitchenette. Three beautifully appointed bedroom suites, two scenic balconies, and a purpose-built home theater create an environment tailor-made for indulgence and entertainment. A new boathouse, soon to be constructed, further elevates the lakefront lifestyle. With three garages, a contemporary parking court, and meticulously executed architectural detail, this residence embodies modern luxury at its most refined. Lake Seminary, home to just 35 exclusive residences, offers coveted privacy while remaining moments from boutique shopping, celebrated dining and best of Winter Park. Immediate access to Interstate 4 and surrounding beltways ensures effortless connectivity throughout Central Florida.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Mel Bernstein (407-810-4726)
1033 HAMLET DR, MAITLAND, FL 32751
$350,000244 Days on yellowkey MLS ID: O6359229
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1146 Built: 1994Monthly Fee: $52 Tax: $474 (2024)Community: Hamlet At MaitlandSingle Family
Taxes:$474
Remarks: This charming 3-bedroom, 2-bathroom single-family home with the best of Florida living. Located in the north of Orlando (Maitland - Winter Park area). 1.3 miles to the Center of Winter Park Shopping Plaza (Office Depot, UPS, Ross, Marshalls, Home Goods, Five Below, LA Fitness, Petco and Michaels, Whole Foods Markets, and Banking). Access to major highways, minutes to downtown, and Orlando's world-renowned theme parks. This 1,146 square foot home features an open-concept floor plan. Primary suite includes a walk-in closet and a private suite bathroom, plus two additional bedrooms that provide flexibility for guests, family or a home office. 1 car garage with a large driveway that accommodates 2 more cars. The property's best feature is solar panels owned outright! With an average monthly bill of $35.00!!! Don't miss your chance to make it yours - schedule a private showing today!
Listing is courtesy of: BOX REAL ESTATE LLC (954-526-3900)
Listing Agent: Bennie Olivo (954-305-0844)
1074 HAMLET DR, MAITLAND, FL 32751
$308,000347 Days on yellowkey MLS ID: O6331672
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1076 Built: 1994Monthly Fee: $52 Tax: $1,135 (2024)Community: Hamlet At MaitlandSingle Family
Taxes:$1,135
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bathroom home that blends comfort, convenience, and an unbeatable location. From the moment you step inside, you’ll notice the inviting layout featuring a spacious living area filled with natural light and a functional kitchen equipped with newer stainless steel appliances—perfect for everyday living and entertaining alike. The home sits on a fully fenced lot with durable vinyl fencing, offering both privacy and a secure space for pets or play. Just beyond your backyard, enjoy direct access to a public playground—an ideal setup for families or anyone who loves being outdoors without losing the comfort of home. With a low HOA and a prime location, this home offers easy access to some of the area’s most exciting new developments and local favorites. You’ll be just minutes from the brand-new Lifetime Fitness currently under construction, the state-of-the-art HostDime data center, Winter Park Village, Whole Foods, and Amtrak. Plus, with quick access to I-4, commuting and weekend getaways are a breeze. Whether you’re a first-time buyer, downsizing, or looking for a solid investment in a growing area, this property offers the perfect blend of value, lifestyle, and location. Don’t miss your chance to make it yours!
570 MANOR RD, MAITLAND, FL 32751
$12,500,000451 Days on yellowkey MLS ID: O6300040
Bed: 6 Bath: 8.5 Gar: 6 Liv Area Sq Ft: 11668 Built: 1996 Tax: $61,937 (2024)Community: Lake Maitland ManorSpa: YesSingle Family
Taxes:$61,937
Remarks: Welcome to Maison du Lac – a breathtaking lakefront estate that epitomizes unrivaled luxury, timeless elegance, and an extraordinary lifestyle. Situated on an expansive 2.7-acre lot along the prestigious Winter Park Chain of Lakes, this extraordinary residence showcases over 120 feet of pristine lakefront with sweeping panoramic views of the longest stretch of Lake Maitland. Blending classic Mediterranean architecture with state-of-the-art modern enhancements, Maison du Lac is a stunning fusion of enduring charm and contemporary sophistication. Originally constructed with timeless materials – including stucco exteriors and expansive windows – the home has been meticulously transformed into an 11,668-square-foot architectural masterpiece. Clean lines and open-concept living harmonize with rich textures and refined details, resulting in an environment that is both stately and smart. Upon entering through the grand 14-foot custom iron door, you are greeted by soaring dual staircases and exquisite finishes in marble, granite, and intricate moldings that reflect the home’s bespoke craftsmanship. A showstopping, $250,000 crystal chandelier—custom-designed and operable at the touch of a button—crowns the expansive great room, setting a dazzling tone for the professionally curated interiors. A private elevator adds convenience and accessibility across all levels of the home. The fully reimagined kitchen is a culinary showpiece, featuring top-of-the-line Wolf appliances, gleaming Cambria countertops, a large walk-in pantry, and expansive prep space ideal for entertaining at any scale. Whether hosting a lavish dinner or a relaxed brunch, the kitchen delivers both impeccable style and everyday functionality. The private master wing is an indulgent retreat, complete with a cozy fireplace, executive office, sauna, fitness room, and dual custom walk-in closets. Five additional en-suite bedrooms are thoughtfully positioned for maximum privacy, offering luxurious accommodations for family and guests. With seven full bathrooms and three half baths, the residence is ideally equipped for both refined daily living and grand-scale entertaining. For effortless indoor-outdoor living, multiple entertainment spaces flow seamlessly onto a sprawling lakefront patio. The outdoor summer kitchen, complete with a powered screen enclosure, provides the perfect setting for alfresco dining while enjoying sunset views over the water. A brand-new dock with a boat lift invites leisurely days spent boating, fishing, or simply relaxing on the lake. Outside, the estate continues to impress. Two serene fishponds with fountains create a tranquil sense of arrival, while the fully fenced and gated grounds ensure ultimate privacy. The residence is equipped with a full-home LUTRON smart system, offering intuitive control of lighting, ambiance, and automation. Additional features include a six-car garage, a resort-style swimming pool, newly updated landscaping, and custom exterior lighting. Maison du Lac is more than a home, it’s a lifestyle of distinction, privacy, and effortless sophistication. This is the lakefront living at its finest.
Listing is courtesy of: FORTUNE INTERNATIONAL REALTY (305-400-6393)
Listing Agent: Maggie Walas (407-701-0144)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.