Location: Maitland
Do Not Show Listings
545 CLARK ST, MAITLAND, FL 32751
$325,0001 Day on yellowkey MLS ID: O6425541
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1950 Built: 1997 Tax: $5,473 (2025)Community: Eatonville LawrenceSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,473
Elementary School: Hungerford Elem
High School: Edgewater High
Tax Year: 2025
Middle School: Maitland Middle
Remarks: Great home in an excellent location,. Inside is a canvas ready for your design work. There is an enclosed front and rear porch. Separate formal living and dining rooms. The kitchen is spacious with a large eat in space. The family room off the kitchen is quiet and perfect for movie nights. All 3 bedrooms are spacious. The primary has a huge walk in closet and large bathroom with a water closet for privacy. Also inside is a roomy laundry room for extra space for storage. The property features a spacious 2 car garage at the rear of the property. Excellent opportunity to make this property your own! Roof over home and garage replaced in 2024.
Listing is courtesy of: MOREHOUSE REALTY INC (407-331-4444)
Listing Agent: Alvin Moore (407-331-4444)
140 WIGWAM PL, MAITLAND, FL 32751
$599,90086 Days on yellowkey MLS ID: O6401560
REDUCED by $10,000 (1.6%) on 07/15/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2236 Built: 1957 Tax: $3,978 (2025)Community: Dommerich EstatesSingle Family
Taxes:$3,978
Elementary School: Dommerich Elem
High School: Winter Park High
Remarks: One or more photo(s) has been virtually staged. Motivated seller! Move-in ready. Tucked away on a cul-de-sac in beautiful Maitland, this 3-bedroom, 3-bath home with a bonus room offers space, comfort, and privacy on a generous 1/3-acre lot. With 2,236 square feet of living space and a 2-car garage, the home features an updated kitchen and upgraded bathrooms, blending modern touches with everyday functionality. Enjoy cozy evenings by the fireplace or relax in the bright sunroom overlooking the fully fenced backyard with a concrete wall for added privacy. A screened-in porch provides the perfect spot to enjoy Florida living year-round. Homeowners have access to Lake Minnehaha and by the way of the Winter Park chain of lakes, Lake Maitland. Access can use for boat launch or watercraft, dock for fishing, picnic area, kayak storage. It’s only $200 year annually. Only $100 year if no boats or watercraft privileges needed. This home’s prime location in Maitland provides easy access to top-rated schools, parks, shopping, dining, and major highways, making it both a peaceful retreat and a convenient base for daily living!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Blake Bolton (407-318-0361)
751 SEQUOIA TRL, MAITLAND, FL 32751
$875,00066 Days on yellowkey MLS ID: O6400821
REDUCED by $24,000 (2.7%) on 06/25/2026
Bed: 5 Bath: 3.5 Liv Area Sq Ft: 3138 Built: 1967 Tax: $4,080 (2025)Community: Dommerich WoodsSingle Family
Taxes:$4,080
Elementary School: None
High School: None
Middle School: None
Remarks: Virtually Staged. Located in one of Maitland’s established and tree-lined communities, this distinctive Mid-Century Inspired Chalet residence offers exceptional space, dramatic design elements, and endless potential for modern transformation. Positioned within sought-after school district the home benefits from access to some of the area’s most well-regarded schools. The home’s impressive pavered approach sets the stage for its chalet-inspired architecture, where soaring A-frame rooflines, dramatic window walls, and natural stone detailing create an unforgettable presence beneath a canopy of mature trees — where “Colorado ski chalet meets Old Florida.” With 5 bedrooms and 3.5 bathrooms, the home is filled with high ceilings, expansive windows, and retro-inspired details that create character throughout. A striking open staircase with vintage styling showcases craftsmanship and design elements rarely found in today’s construction, while a massive paver courtyard welcomes guests and enhances the home’s unique indoor-outdoor lifestyle. Inside, the formal dining and sunken living room feature coffered ceilings and a dramatic circular brick fireplace centerpiece, while walls of windows flood the interiors with natural light. The spacious kitchen includes a cooking island, double wall ovens, closet pantry, breakfast nook, and an abundance of windows overlooking the private backyard area. Adding exceptional flexibility, the home also features a private in-law suite with its own separate entrance. The space includes a sleeping area, small seating/living space, private bathroom, kitchenette area with refrigerator and countertop workspace, and an eat-in area — ideal for multigenerational living, long-term guests, a private home office setup, or potential income-producing opportunities. The upstairs bedrooms open onto a rear balcony, creating a true retreat feel among the mature trees and landscaped surroundings. The primary bath features angular ceilings, oversized triangular windows, and a custom mosaic tile tub and double vanity that reflect the home’s original retro contemporary character. Outdoors, enjoy a sparkling swimming pool surrounded by shade trees, an expansive paver deck, and a fully fenced yard ideal for entertaining, gardening, or creating a private oasis. Recent updates include new roof 2024, along with a transferrable shingle warranty, both A/C HVAC units replaced 2019 and 2023, hot water heater was replaced in 2019, 2023 electrical work done, 2022 high end Samsung dishwasher installed, transferrable premium home appliance warranty expiring Feb 3 2027, gas-powered portable generator and underground utilities. This home presents an exciting opportunity for buyers seeking architectural character and the chance to personalize a spacious residence with cosmetic updates including flooring, wall finishes, and modern design enhancements. Conveniently located near top-rated dining, shopping, parks, and major commuter routes, Maitland remains one of Central Florida’s most desirable established communities, known for its timeless charm, mature landscapes, and exceptional location.
Listing is courtesy of: THOMAS LYNNE REALTY GROUP LLC (407-808-0899)
Listing Agent: Patrick Hancock (407-808-0899)
229 FLAME AVE, MAITLAND, FL 32751
$995,0009 Days on yellowkey MLS ID: O6422450
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4055 Built: 1971Monthly Fee: $17 Tax: $7,127 (2025)Community: Hidden Estates Unit 3Spa: YesSingle Family
Taxes:$7,127
Remarks: Welcome to Hidden Estates, where luxury, space, and flexibility come together in one of Maitland's most sought-after neighborhoods. Nestled on a quiet cul-de-sac, this rare single-story custom residence offers over 4,000 square feet of thoughtfully designed living space on an expansive three-quarter-acre lot. From the moment you arrive, you'll appreciate the impressive curb appeal, oversized driveway, and exceptional parking with plenty of room for multiple vehicles, boats, RVs, trailers, and recreational equipment. Inside, the home's spacious open layout is designed for both everyday living and entertaining, featuring soaring ceilings, hardwood flooring, crown molding, skylights, custom built-ins, plantation shutters, and a wood-burning fireplace. At the center of the home is a beautifully appointed chef's kitchen with custom mahogany cabinetry, granite countertops, a Thermador refrigerator, six-burner gas cooktop, double ovens, an oversized island with bar seating, and a generous walk-in pantry. The luxurious primary suite serves as a private retreat with its own sitting area, walk-in closet, heated bathroom floors, dual vanities, oversized walk-in shower, and freestanding soaking tub. One of the home's most unique features is its flexible layout, including a private guest suite situated on the opposite side of the home and a separate office overlooking a tranquil atrium, offering endless possibilities for guests, multigenerational living, a home office, or creative space. Step outside to your own private backyard oasis featuring a screened saltwater pool and spa with waterfall, an expansive covered lanai, and abundant outdoor living space designed for year-round Florida enjoyment. The oversized lot provides exceptional privacy while offering ample room to relax, entertain, or personalize the outdoor space. Additional highlights include a metal roof with copper fascia (2018), new septic drain field, and an unbeatable Maitland location convenient to shopping, dining, parks, major roadways, and everyday conveniences. This is a rare opportunity to experience the space, privacy, and versatility that define luxury living in Maitland.
Listing is courtesy of: BHHS FLORIDA REALTY (407-406-5300)
Listing Agent: Heather Meglino (813-810-7530)
703 NICOMA TRAIL, MAITLAND, FL 32751
$725,00058 Days on yellowkey MLS ID: O6408335
REDUCED by $10,000 (1.4%) on 07/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1842 Built: 1961 Tax: $4,767 (2025)Community: Dommerich HillsSpa: YesSingle Family
Taxes:$4,767
Remarks: Located in the sought after Dommerich neighborhood, this beautifully maintained pool home is just a short walk to Dommerich Elementary and Maitland Middle School. Hardwood floors and an open floor plan create an easy flow for everyday living and entertaining, centered around a spacious kitchen with a gas range, breakfast bar, and generous gathering space. Additional features include a wood burning fireplace and an indoor laundry room. Major updates provide peace of mind, including a roof replaced four years ago, a six year old HVAC system, a water heater less than one year old, updated electrical and plumbing completed during the 2010 renovation, and a whole house generator powered by a 500 gallon propane tank. Outside, enjoy a large backyard with a pool, heated spa, and plenty of room to entertain, while a welcoming covered front porch with pavers and a tongue and groove ceiling adds warmth and curb appeal.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Jennifer King (407-595-3272)
2040 GERONIMO TRL, MAITLAND, FL 32751
$725,000127 Days on yellowkey MLS ID: O6390221
REDUCED by $24,900 (3.3%) on 07/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2375 Built: 1963 Tax: $3,301 (2025)Community: Highland Park EstsSingle Family
Taxes:$3,301
Remarks: Virtually Staged. Set on one of the most sought-after streets in Dommerich, this completely renovated home combines the solid construction of a 1963 block home with thoughtful modern updates throughout. From the moment you arrive, the circular driveway, classic brick accents, and welcoming front porch set the tone. Inside, a bright foyer opens to beautiful solid maple wood floors and a light, airy feel that carries throughout the home. To the right, the formal living room features built-in shelving and a striking brick wood-burning fireplace, while the adjoining formal dining room connects directly to the kitchen and can be closed off with pocket doors if you want a little separation. The eat-in kitchen is truly the heart of the home, showcasing rich solid cherry cabinetry, unique man-made glass countertops, a large farmhouse sink, and top-of-the-line stainless Bosch appliances including a built-in oven and gas cooktop. A generous peninsula overlooks the oversized family room, where French doors open to a stunning Florida room that fills the home with natural light. This space is a showstopper—large, lined with windows, and finished with soaring shiplap ceilings—creating the kind of room you’ll use year-round, with direct access to the backyard. The primary suite is spacious and refined with crown molding, a built-in closet plus a walk-in, and a beautifully renovated bath featuring matching glass countertops, a Kohler vanity, and a glass shower with both a large rain head and handheld fixture. Two additional bedrooms are generously sized and share an updated hall bath with a large vanity, classic subway tile, and a soaking tub. The interior also includes a well-equipped laundry room with cabinetry, a cedar storage closet, and access to the two-car garage. Out back, the fully fenced private yard offers plenty of room for entertainment, recently re-sodded with irrigation and enclosed with a brand new wood fence installed in 2025—leaving ample space for a future pool or patio if desired. Additional upgrades include smooth flat ceilings with recessed lighting throughout, new drywall, plantation shutters, updated windows and doors, and an energy-efficient hybrid water heater. Beyond the home itself, the location is hard to beat—just a short walk to Dommerich Elementary, Maitland Middle School, and Maitland Community Park offering tennis courts, indoor racquetball, and playgrounds. Zoned for highly regarded Winter Park High School. Call today to schedule your private showing!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Maria Van Warner (407-256-8066)
448 STONEWOOD LN, MAITLAND, FL 32751
$599,900143 Days on yellowkey MLS ID: O6385060
REDUCED by $25,090 (4.0%) on 07/15/2026
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
Elementary School: Lake Orienta Elementary
High School: Lyman High
Middle School: Milwee Middle
Remarks: Virtually Staged. Short Sale. 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)
2666 TUSCARORA TRL, MAITLAND, FL 32751
$549,99014 Days on yellowkey MLS ID: O6422193
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1960 Built: 1968Monthly Fee: $8 Tax: $1,734 (2025)Community: Forest BrookSingle Family
Taxes:$1,734
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: South Seminole Middle
Remarks: Welcome home to this exceptional 4-bedroom, 3-bathroom residence in the heart of Maitland, where timeless style meets modern updates and meticulous care. From the moment you pull into the driveway, you'll immediately notice the incredible pride of ownership that sets this home apart. Completely renovated and lovingly maintained, this move-in-ready property is sure to impress even the most discerning buyers. The beautifully remodeled 2025 kitchen is the centerpiece of the home, featuring contemporary finishes, updated cabinetry, quality stone countertops, and a functional layout that makes cooking, entertaining, and everyday living a pleasure. Just steps away, the spacious living and dining areas provide the perfect setting for family gatherings or hosting friends. The luxurious primary suite offers a peaceful retreat, highlighted by a stunning primary bathroom renovation completed in 2025 with elegant finishes and a spa-inspired feel. Both guest bathrooms were tastefully updated in 2023, ensuring every space in the home feels fresh, modern, and inviting. This home also offers the peace of mind that comes from knowing the major improvements have already been completed. The roof was replaced in 2021, while all windows and sliding glass doors were replaced in 2022, enhancing both energy efficiency and curb appeal. In 2025, the plumbing system received significant updates, including new sewer lines and a new water heater, allowing you to move in with confidence. Even the details have been thoughtfully addressed, with the garage floor and back porch both professionally refinished with durable epoxy coatings in recent years. Step outside and you'll discover an expansive backyard that's ready for whatever lifestyle you envision. There's plenty of room for children and pets to run and play, space to entertain family and friends, or simply relax and enjoy Florida's beautiful weather. Gardening enthusiasts will especially appreciate the raised planter beds, which are ideal for growing fresh vegetables, herbs, flowers, or your favorite fruit plants. Whether you dream of creating your own backyard oasis or simply enjoying the open space, this yard offers endless possibilities. Located in one of Maitland's most desirable areas, you'll enjoy convenient access to outstanding shopping, dining, parks, entertainment, and major roadways while still coming home to a quiet, established neighborhood. Combining extensive renovations, quality craftsmanship, major system upgrades, and impeccable maintenance, this is a home that truly stands out from the competition. Every expensive project has already been completed, allowing you to simply unpack, settle in, and start making memories. The only thing this incredible Maitland home is missing is its new owner.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Jonathan Cole (407-928-9516)
204 QUAYSIDE CIR #504, MAITLAND, FL 32751
$458,500146 Days on yellowkey MLS ID: O6383019
0 Days Off yellowkey (back on 6/24/2026)
REDUCED by $500 (0.1%) on 05/02/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1270 Built: 1984Monthly Fee: $590 Tax: $6,851 (2024)Community: Moorings On Lake Maitland CondoCondo
Taxes:$6,851
Elementary School: Lake Sybelia Elem
Tax Year: 2024
Remarks: Seller to pay up to one year of HOA! Wake up to shimmering lake views and unwind each evening with breathtaking Florida sunsets in this beautifully refreshed 2-bedroom, 2-bathroom condo. From the moment you step off the elevator, you’re welcomed into a light-filled, open-concept living space highlighted by oversized glass sliding doors that lead to a private enclosed patio—seamlessly blending indoor and outdoor living. The kitchen is both bright and inviting, featuring upgraded cabinetry, a spacious eat-in area, and a large island designed for effortless entertaining. Thoughtful updates throughout include upgraded flooring, brand-new carpet installed just six months ago, and a newer AC unit replaced two years ago for added comfort and peace of mind. Custom-tailored curtains complete the space with a refined, polished finish. cThe primary suite offers a quiet, private retreat with its own bath, while the split-bedroom layout ensures comfort and privacy for guests. Life at The Moorings is centered around a relaxed, lakeside lifestyle—complete with a community pool, heated spa, clubhouse, lushly landscaped grounds, and direct access to Lake Maitland on the Winter Park Chain of Lakes. Spend your days on the lakefront dock or hosting poolside gatherings, then enjoy the convenience of walking to local favorites like Luke’s and Antonio’s or exploring Maitland’s newly designed downtown with green spaces, farmers markets, and vibrant community events.
Listing is courtesy of: LUXE HUNTER REAL ESTATE (407-984-4888)
Listing Agent: Allison Hunter (407-221-4669)
2150 TORTOISE SHELL DR, MAITLAND, FL 32751
$399,90085 Days on yellowkey MLS ID: O6392895
REDUCED by $10,000 (2.4%) on 07/15/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1512 Built: 1997Monthly Fee: $17 Tax: $5,334 (2025)Community: WinfieldSingle Family
Taxes:$5,334
Middle School: Lockhart Middle
Remarks: One or more photo(s) has been virtually staged. PRICE REDUCED. Owner Motivated! 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 Agent: Claire Sims, Llc (203-767-8109)
2130 DELORAINE TRL, MAITLAND, FL 32751
$779,000101 Days on yellowkey MLS ID: O6397018
REDUCED by $20,000 (2.5%) on 07/11/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2175 Built: 1964 Tax: $10,394 (2025)Community: Highland Park Estates First AddSpa: NoSingle Family
Taxes:$10,394
Remarks: HUGE PRICE REDUCTION. Welcome to this beautifully renovated pool home in the highly sought-after Dommerich neighborhood of Maitland. Offering over 2,000 square feet of living space, this 3-bedroom, 2-bath residence perfectly blends modern upgrades with comfortable, functional living. Inside the home is designed for both everyday living and entertaining. The spacious living room serves as the heart of the home, featuring a stunning marble fireplace and seamless flow into multiple gathering areas, including a dedicated dining space just off the kitchen, a family room that leads to the outside and access to the bedrooms. The fully renovated chef’s kitchen is a true standout, showcasing soft-gray shaker cabinetry, quartz countertops, a Carrera marble backsplash, and stainless steel appliances. With ample counter space and a built-in water filtration system, this kitchen is as functional as it is beautiful. Throughout the home, you’ll find upgraded Italian wood-plank porcelain tile flooring, offering both durability and elegance. The primary suite provides a peaceful retreat with a walk-in closet and a fully updated ensuite bathroom featuring a double-sink vanity, granite countertops, and a spacious walk-in shower with marble and porcelain finishes. Step outside into your private backyard oasis. Designed for true Florida living, this space features a Pebble Tec pool, paver deck, covered gazebo with ceiling fan, a 65” outdoor TV, and a premium sound system perfect for entertaining or relaxing year-round. The lush landscaping, grassy area, and additional storage shed complete the outdoor experience. Additional highlights include a new roof (2019), A/C system (2021), WiFi-enabled irrigation system, fresh interior paint, and new LG washer, dryer, and dishwasher. Located in the desirable Dommerich area, just minutes from top-rated schools, dining, shopping, and major roadways, this home offers the perfect combination of location, upgrades, and lifestyle. This is the one you’ve been waiting for.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Mario Zendeli (407-325-3893)
1424 RIDGEWOOD AVE, MAITLAND, FL 32751
$975,0007 Days on yellowkey MLS ID: O6424220
0 Days Off yellowkey (back on 7/14/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3070 Built: 2020 Tax: $8,712 (2025)Community: Coffins SubTownhouse
Taxes:$8,712
Remarks: Under contract-accepting backup offers. Built in 2020, this pristine townhome offers over 3,000 square feet of thoughtfully designed living space with NO HOA, two primary suites (one on each floor), 10-foot ceilings throughout, a private fully fenced backyard, and an unbeatable location just north of Park Avenue, tucked behind the Enzian Theater. Enjoy easy access to downtown Winter Park, Whole Foods, the recently revitalized Winter Park Village, Maitland, and Orlando. Designed for effortless, move-in-ready living, this modern 4-bedroom, 3.5-bath home features a spacious 2-car garage, abundant storage, and an ideal floor plan. The main level showcases distinctive stained and sealed concrete floors, while the open-concept living spaces are filled with natural light from 8-foot glass sliders overlooking the private backyard and patio. The beautifully appointed kitchen features white cabinetry extending to the 10-foot ceilings, granite countertops, a large center island, walk-in pantry, stainless steel appliances, a new Bosch dishwasher (Nov. 2024), a range, second built-in oven, and warming drawer. The adjoining dining and living areas are enhanced by a custom wood-plank accent wall and an open wood staircase. With over $60,000 in recent upgrades and improvements, this home has been thoughtfully enhanced with fresh interior paint, upgraded LED lighting and ceiling fans, custom accent walls, artificial turf, new gutters and drainage, UV window film, whole-house surge protection, an electric vehicle charging station, epoxy garage flooring, custom garage storage, and more. The first-floor primary suite offers two closets, including a walk-in closet and a second closet with washer/dryer hookups, plus a luxurious bath with a zero-entry glass shower and private water closet. Upstairs, a second primary suite features dual walk-in closets and a spacious bath, while two additional bedrooms, a full bath with dual sinks, a generous bonus room, and a large laundry room provide exceptional flexibility. Combining newer construction, quality upgrades, an exceptional floor plan, and a prime location, this move-in-ready home truly offers the best of low-maintenance living. Zoned for sought-after Dommerich Elementary, Maitland Middle School, and Winter Park High School.
Listing Agent: Marystuart Day (407-620-8683)
499 JULIAN LN, MAITLAND, FL 32751
$449,00061 Days on yellowkey MLS ID: O6408583
REDUCED by $6,000 (1.3%) on 07/14/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1596 Built: 1997Monthly Fee: $79 Tax: $2,495 (2025)Community: Brittany GardensSingle Family
Taxes:$2,495
Remarks: Location, Location, Location. Welcome to your new home in Maitland! This conviently located gated community home is a charming dwelling place featuring a cozy fireplace to uplift the ambiance of your living space. The home benefits from a tasteful neutral color paint scheme throughout, providing a welcoming canvas for your interior design aspirations. The kitchen is a cook's paradise, complete with a natural gas range, a stunning accent backsplash that truly makes the room pop and new applicances. Enjoy the luxury of a generous walk-in closet in the primary bedroom, perfect for all your storage needs. The primary bathroom offers the convenience of double sinks, making morning routines smooth and efficient. The shower in the primary bathroom add an opulent touch to your personal spa-like retreat. Relax or entertain with ease with a patio for outdoor gatherings. The fenced-in backyard promises privacy for all your outdoor activities. The home benefits from a newer roof, new AC, new hot water tank, ensuring peace of mind for years to come. The appeal of the property is enhanced by fresh interior paint and fresh exterior paint to the entire home. The comfort features continue with new flooring throughout, ensuring all areas of the home are updated. Take advantage of this home's remarkable attributes and turn this dwelling place into your personal sanctuary. Some pictures virtually staged.
Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)
Listing Agent: Charles Munk (407-417-7709)
119 HOLLIE CT, MAITLAND, FL 32751
$975,000177 Days on yellowkey MLS ID: O6375808
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2192 Built: 1964 Tax: $12,057 (2024)Community: Hollieanna ShoresSingle Family
Taxes:$12,057
Remarks: Located in a premier Maitland neighborhood, 119 Hollie Ct presents a rare opportunity to own a beautifully maintained home in an established pocket community where properties seldom come on the market. This secluded one-level residence sits on a private lot and includes deeded access to the neighborhood boat ramp and the renowned Chain of Lakes, bringing waterfront recreation within easy reach. Inside, you will find 2,192 square feet of bright and inviting living space across 3 bedrooms and 3 bathrooms. The kitchen opens directly into the gathering room, where a cozy fireplace creates a warm focal point for relaxing or hosting friends and family. An adjoining sunroom takes full advantage of the home's southern exposure, filling the interior with natural light throughout the day and adding a cheerful energy to everyday living. The split floor plan is designed with privacy in mind. The oversized primary suite occupies one side of the home and features a large ensuite bathroom with double sinks, a separate shower, and a soaking tub for those well-deserved moments of relaxation. On the opposite side, two additional bedroom suites provide comfortable and independent spaces for family members or visiting guests. A small bonus area adds welcome flexibility, serving nicely as a home office, hobby room, or creative studio. Outside, the backyard offers a true personal retreat. A sparkling pool and a terrace shaded by a beautiful pergola create the perfect setting for entertaining outdoors or simply unwinding in peace. The seamless blend of indoor and outdoor spaces makes this home ideal for the Florida lifestyle. Beyond the property itself, the location delivers everyday convenience with easy access to shopping, restaurants, theme parks, major roads, and the airport. You get the best of quiet suburban living without sacrificing proximity to everything Central Florida has to offer. Homes in this neighborhood rarely become available, making this a truly unique opportunity. Schedule your private showing today and see everything this special property has to offer before it is gone.
Listing Agent: Drew Belani (407-203-9441)
2112 CHIPPEWA TRL, MAITLAND, FL 32751
$899,000106 Days on yellowkey MLS ID: O6394702
REDUCED by $50,000 (5.3%) on 07/14/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2407 Built: 1961 Tax: $2,725 (2025)Community: Dommerich HillsSpa: NoSingle Family
Taxes:$2,725
Remarks: NEW PRICE…NEW OPPORTUNITY!! This beautiful, impeccably maintained and updated four bedroom and three and a half bath pool home absolutely has it all, including the added benefit of new electrical wiring throughout. Perfectly located in Maitland’s much sought after Dommerich neighborhood and walking distance to top rated elementary and middle schools. This attractive split-floor plan offers for spacious bedrooms and three full baths on the first level and a bonus room/5th bedroom with half bath on the second level. The gorgeous kitchen, boasts handsome, solid wood cabinets, granite countertops, and stainless steel appliances with double ovens. The first floor open layout includes a large dining area with brick fireplace leading into a wonderfully sized family room with fireplace and custom built-ins. Newly installed double pane, hurricane proof French doors brings in tons of natural light and leads out to your private oasis, including the newly resurfaced pool with new pool pump and filter, brick paver deck, open patio, and super fun gazebo with gas grill and nighttime lighting for entertaining! Awesome potential to install gas into the kitchen, as well. This home is fully supported by a new Generac system, never to be without power! Entire interior just freshly painted and new carpets installed in bedrooms and bonus room. Newer ROOF (2021), HVAC (2020) and tankless water heater. Samsung washer and dryer also included. Gorgeous architectural landscape with LED lighting add to its charm and warmth. This opportunity does not come along often and is absolutely MOVE-IN READY! Look forward to meeting you there!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Laura Lane Heidrich (321-662-7491)
1140 S ORLANDO AVE #E2, MAITLAND, FL 32751
$209,50062 Days on yellowkey MLS ID: O6404875
REDUCED by $5,000 (2.3%) on 07/14/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 612 Built: 1971 Tax: $539 (2025)Community: Lake Maitland Terrace AptsCondo
Taxes:$539
Remarks: Live the lake lifestyle in this beautifully updated 1-bedroom condo located in the iconic mid-century modern community of Lake Maitland Terrace. Completely refreshed in 2025, this first-floor residence features a brand-new HVAC system, new appliances including washer, dryer, and kitchen disposal, updated kitchen countertops, and new flooring throughout the living areas. Freshly painted and thoughtfully enhanced, the home blends timeless mid-century character with modern comfort and style. The spacious bedroom showcases sleek modern concrete flooring, adding to the authentic architectural aesthetic and contemporary feel. Perfectly positioned within a charming two-story mid-rise building, this residence offers effortless access to the community’s exceptional waterfront amenities and relaxed lakefront atmosphere. Set on Lake Maitland—the largest lake on the Winter Park Chain of Lakes—residents enjoy direct lake access for boating, kayaking, canoeing, fishing, and water-skiing. A private community dock is located on-site, while the City of Maitland public boat ramp sits conveniently next door. Boat slips may also be available upon request. The location is truly unbeatable. Just one block from Lake Lily and Fort Maitland Park, and only minutes from Park Avenue, residents can walk to the Maitland Farmers Market, local restaurants, coffee shops, gym, dry cleaning, barber shop, boba tea, and more—all directly across the street. Enjoy easy biking access to Park Avenue for premier shopping, dining, and entertainment. Residents of Lake Maitland Terrace enjoy outstanding amenities including a newer community pool, lakefront clubhouse with breathtaking views available for private events, on-site laundry facilities, free unlimited water, and twice-weekly valet trash service. Experience maintenance-free living where iconic mid-century modern design meets modern updates and an unmatched Central Florida lakefront lifestyle.
Listing is courtesy of: METRO CITY REALTY (407-237-3331)
Listing Agent: Beatrice Miranda (407-592-4448)
601 ORANOLE RD, MAITLAND, FL 32751
$385,900375 Days on yellowkey MLS ID: O6324872
3 Days Off yellowkey (back on 5/21/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1950 Built: 1958 Tax: $4,216 (2024)Community: Oakland Shores 3Rd Add RepSingle Family
Taxes:$4,216
Remarks: Under contract-accepting backup offers. Back on the market with renewed momentum. Nestled in one of Maitland's most sought-after neighborhoods, this fully renovated 3-bedroom, 2-bathroom home offers the perfect blend of modern comfort and timeless charm, ideal for families ready to make new memories. From the moment you step inside, you're greeted by an abundance of natural light and an open, airy layout that instantly feels like home. The heart of the house, the newly renovated kitchen features sleek stone countertops and new appliances, making it perfect for family meals and holiday gatherings. Step outside to the screened-in patio and picture slow mornings with coffee in hand, or peaceful evenings unwinding from a long day in the spacious backyard. Whether hosting a barbecue or enjoying a quiet night under the stars, this outdoor space is made for relaxation! Located just minutes from top-rated schools, grocery stores, dining, and major highways and less than 10 miles from the natural beauty of Wekiwa Springs State Park. This home offers the convenience you need and the lifestyle you've been dreaming of. Don't miss this opportunity to plant roots and grow in a home that has it all. Schedule your private tour today and discover the warmth, space, and charm waiting for your family.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Kay Shilling (407-716-9861)
249 W LAKE FAITH DR #205, MAITLAND, FL 32751
$315,00063 Days on yellowkey MLS ID: O6406744
REDUCED by $10,000 (3.1%) on 07/13/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1739 Built: 1974Monthly Fee: $620 Tax: $1,339 (2025)Community: Lake Faith VillasCondo
Taxes:$1,339
Remarks: One or more photo(s) has been virtually staged. Tucked away in this delightful and quiet lakefront community this beautifully renovated GROUND FLOOR condo offers so much, including a 2 PARKING SPACES - one is a deeded carport and the other is an open assigned parking spot... And there is a separate storage closet too! Situated on one level, this condo overlooks the charming grounds and a peek of Lake Faith from the living areas and porch. Inside is a treat for sure with a large open living and dining room layout that is light and bright. The unit has a luxury vinyl plank flooring throughout most of the unit and tile flooring in the kitchen and baths. The kitchen is updated with granite countertops and plenty of cabinetry. Off the living room is an expansive back porch that has tile flooring and was recently updated with newer windows and entry door (2024) .... And off the dining area is a charming, covered porch. So, lots of areas to enjoy day to day or if you like to entertain. The master bedroom is a spacious size and also opens to the back porch… You will love the master bath - completely redone with a large shower, a stylish vanity with ample storage as well as a make-up vanity and a generous walk-in closet. The 2 additional bedrooms are both a good size with great closet storage. Other notable features are the inside laundry closet with open shelving and newer LG washer and dryer (2024) and the custom shades installed in the living areas and bedrooms (2023). Along with these upgrades, there have been system updates including new hot water heater (2015), new AC (2016) and replumbed (2013). This complex offers a private, tranquil atmosphere and has terrific amenities including a gated entrance, clubhouse, and pool. And the location couldn’t be more convenient, with easy access to I-4 as well as a new retail and restaurant development within a short stroll. This is one not to miss!
Listing Agent: Dawn Romance (407-929-2826)
1166 N LAKE SYBELIA, MAITLAND, FL 32751
$2,999,00050 Days on yellowkey MLS ID: O6411525
REDUCED by $101,000 (3.3%) on 07/13/2026
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 Agent: Joseph Sipp (407-820-7016)
823 WOODS COURT, MAITLAND, FL 32751
$950,00011 Days on yellowkey MLS ID: O6422384
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2145 Built: 1979 Tax: $7,742 (2025)Community: Dommerich WoodsSingle Family
Taxes:$7,742
Remarks: Outstanding Dommerich Woods location on .28 acre lot with serene views of the nature preserve! This immaculate home offers the perfect blend of comfort, style and privacy. Tucked away on a charming tree-lined cul-de-sac, 823 Woods Court welcomes you with exceptional curb appeal. Step inside to a spacious foyer introducing gleaming wood floors, elegant crown molding, and an abundance of natural light. The versatile floor plan offers several inviting living spaces! At the front of the home, the formal living & dining rooms flow seamlessly into the beautifully updated kitchen, complete with a cozy breakfast nook, new cabinetry, quartz countertops, stainless steel appliances and an oversized breakfast bar overlooking bright family room. French doors open to the spectacular 28x11 sunroom with vaulted ceilings and a stunning wall of windows, providing breathtaking views of the manicured backyard, two private patios and the tranquil nature preserve- creating a peaceful retreat you'll enjoy year-round. The spacious primary suite features two closets and a generously sized en-suite bath with dual vanities and built-in storage. Two additional guest bedrooms and a large guest bathroom with built-in closets provide plenty of space for family and visitors. Additional updates and features include fresh interior paint, an inside laundry room, a two-car garage with new garage door, a new Trane HVAC system. new water heater. irrigation system with new well pump, Roof 2018 & NO HOA! Excellent schools: Dommerich Elementary, Maitland Middle & Winter Park High! Residents enjoy access to the Dommerich boat ramp on Lake Minnehaha/Chain of Lakes, as well as a short stroll to the newly refurbished boardwalk leading to Maitland Community Park. This move-in ready home combines an exceptional location, thoughtful updates, and picturesque surroundings ...WELCOME HOME!
Listing Agent: Catherine D'Amico (407-252-3210)
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