Maitland Single Family Homes for sale by Neighborhood

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ACREAGE & UNREC homes for sale ADAMS GROVE homes for sale
CLARK HOMES ACRES homes for sale COOL-MORE SUB homes for sale
DIXIE TERRACE homes for sale DOMMERICH ESTATES homes for sale
DOMMERICH ESTATES 1ST ADD homes for sale DOMMERICH ESTATES 2ND ADD homes for sale
DOMMERICH HILLS homes for sale DOMMERICH HILLS 2 ND ADD homes for sale
DOMMERICH HILLS 3RD ADD homes for sale DOMMERICH HILLS 6TH ADD homes for sale
DOMMERICH HILLS SECOND ADD homes for sale DOMMERICH WOODS homes for sale
DOMMERICH WOODS UNIT 2 homes for sale DOMMERICH/ HIGHLAND PARK homes for sale
DRUID HILLS PARK homes for sale DRUID ISLE homes for sale
ENGLISH ESTATES UNIT 1 homes for sale ENGLISH ESTATES UNIT 2 homes for sale
ENGLISH ESTATES UNIT 3 homes for sale ENGLISH WOODS homes for sale
FLORIDAHAVEN homes for sale FOREST BROOK 3RD SEC homes for sale
HAMLET AT MAITLAND homes for sale HIGHLAND PARK ESTATES homes for sale
HIGHLAND PARK ESTATES FIRST ADD homes for sale HIGHLAND PARK ESTS homes for sale
HOLLIEANNA SHORES homes for sale HOLLIEANNA SHORES 1ST ADD homes for sale
KINGS ROW homes for sale LAKE MAITLAND MANOR homes for sale
LAKE MAITLAND OWL PRESERVE homes for sale LAKE SYBELIA COVE homes for sale
MAITLAND COVE homes for sale MAITLAND GROVE homes for sale
MAITLAND GROVE UNIT 1 homes for sale MAITLAND HIGHLANDS DOMMERICH homes for sale
MAITLAND ISLE homes for sale MAITLAND PARK SOUTH homes for sale
MAITLAND SHORES homes for sale MAITLAND WOODS THIRD ADD homes for sale
MINNEHAHA SHORES homes for sale N/A homes for sale
NORTHGATE homes for sale NORTHWOOD HEIGHTS homes for sale
OAKLAND SHORES homes for sale OAKLEIGH THIRD ADD homes for sale
ORANGEDALE PARK REP homes for sale STONEWOOD homes for sale
SUNSET RIDGE homes for sale SYBELIA PLACE homes for sale
WELLINGTON homes for sale WESTMINSTER homes for sale
WINFIELD homes for sale WINFIELD UNIT 2 homes for sale

Newest Single Family Homes for Sale in Maitland by Neighborhood

View all Maitland Single Family Homes for Sale

  • 2150 TORTOISE SHELL DR, MAITLAND, FL - MLS# O6392895

    WINFIELD - O6392895 - 2150 TORTOISE SHELL DR, MAITLAND, FL 32751
    Just Added on 04/23/2026 12:52PM

    $429,900 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    One or more photo(s) has been virtually staged. 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.

    Contact Yellowkey Agent

    Listing is courtesy of: LPT REALTY, LLC

  • 140 WIGWAM PL, MAITLAND, FL - MLS# O6401560

    DOMMERICH ESTATES - O6401560 - 140 WIGWAM PL, MAITLAND, FL 32751
    1 Day on yellowkey

    $649,900 | Single Family Home | 3 beds | 3.0 baths | 2 gar

    One or more photo(s) has been virtually staged. 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. 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!

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    Listing is courtesy of: LPT REALTY, LLC

  • 612 GREEN MEADOW AVE, MAITLAND, FL - MLS# O6401412

    FOREST BROOK 3RD SEC - O6401412 - 612 GREEN MEADOW AVE, MAITLAND, FL 32751
    1 Day on yellowkey

    $500,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Welcome to a home that doesn’t just check boxes — it supports your lifestyle. Tucked into one of Maitland’s beloved neighborhoods, Forest Brook, this delightful property blends comfort, practicality, and a little everyday serenity. *Lots of new since 2023: Whole house generator, 20’x12’ shed, front and back sod (just completed 4/2026), renovated driveway, gutters, vinyl fence in backyard & so much more!!* Home oozes charm showcasing a sunny yellow exterior with shutter details, white columns on covered front porch, fresh Florida style landscaping, finished concrete driveway, all leading you to covered front entry with pretty leaded glass front door. Step inside to tiled foyer entry and you’ll find a split floor plan offering privacy, flow, and room to spread out — whether you’re hosting, working from home, or simply enjoying a quiet morning. Separate formal dining room complete with sparkling chandelier and French door to patio has yard views. Generous living room has wood floors, new ceiling fan and wall of windows with double French doors to patio plus Plantation shutters. Inviting kitchen is a true gathering spot with a large island with seating on both sides, not to mention all the counter space, white cabinetry, complete stainless steel appliance package and new window above sink. Dedicated office/bonus space has ceiling fan and French door to patio with Plantation shutters. Spacious primary suite flaunts Plantation shutters, new ceiling fan, a walk-in closet plus an en-suite bath with adult height dual vanities, private commode and tiled shower stall. Two guest bedrooms on the other side of the home share updated bath with stylish modern vanity, dual sinks, decorative framed mirrors, chic light and a tub/shower combo. Unwind out back on the oversized covered and screened patio with dual ceiling fans offering lots of gathering space. Every room on the backside of the home contains a French door making it the perfect opportunity for that indoor-outdoor feel. Oversized backyard is fully fenced, freshly sodded and creates the perfect lush, green space ready for play, pets, gardening or gatherings. 20’x12’ shed is a dream for storage lovers or anyone who needs extra space – double doors, tons of room and endless possibilities. No power outages here! A whole house generator keeps life running smoothly no matter the weather. No scrambling, no stress — just uninterrupted comfort and security. Tree lined streets and quick access to parks, major connectors like 436, 414, N Orlando Avenue, Howell Branch Rd/Horatio, Red Bug Rd plus the YMCA, Advent Health and endless dining and shopping options like the Maitland City Center, Downtown Winter Park and so much more— it’s the kind of place where life feels a little easier and a lot more enjoyable!

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    Listing is courtesy of: FLORIDA HOME TEAM REALTY LLC

  • 1511 E HORATIO AVE, MAITLAND, FL - MLS# O6401235

    MINNEHAHA SHORES - O6401235 - 1511 E HORATIO AVE, MAITLAND, FL 32751
    3 Days on yellowkey

    $719,000 | Single Family Home | 4 beds | 3.0 baths

    Welcome to your dream home located in the heart of Maitland, FL. This stunning 4-bedroom, 3-bathroom residence is a perfect blend of modern comfort and timeless elegance. Lease Purchase available with a downpayment. Total Living Area 2760 Sq Ft. As you step inside, you'll be greeted by an inviting foyer that leads to a spacious open-concept living area, featuring high ceilings and abundant natural light. The gourmet kitchen boasts quartz countertops, new appliances, and ample cabinet space, ideal for culinary enthusiasts. The adjoining dining area is perfect for entertaining guests or enjoying family meals. The master suite is a true retreat with a walk-in closet and an en-suite bathroom featuring a luxurious soaking tub, dual vanities, and a separate shower. Three additional bedrooms provide plenty of space for family or guests, while the three full bathrooms ensure convenience and privacy for all. Outside, the large backyard offers a serene setting with a covered fenced-in yard, perfect for outdoor dining or relaxing in the Florida sunshine. The newly meticulously landscaped yard is designed for low maintenance, allowing you to enjoy the beautiful surroundings without the hassle. This property is located in a prime location, just minutes away from top-rated schools such as Maitland Middle School and Winter Park High School. Enjoy easy access to local landmarks and attractions including the Maitland Art Center, Lake Lily Park, and the Enzian Theater. For your shopping and dining needs, the Maitland City Centre and Winter Park Village are just a short drive away, offering a variety of upscale boutiques, restaurants, and entertainment options. Don't miss this incredible opportunity to own a piece of Maitland's finest real estate. Schedule your private tour today and experience the elegance and convenience of 1511 East Horatio Avenue. This home won't last long!

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    Listing is courtesy of: FLORIDA REALTY INVESTMENTS

  • 1281 WELLINGTON TER, MAITLAND, FL - MLS# TB8499961

    WELLINGTON - TB8499961 - 1281 WELLINGTON TER, MAITLAND, FL 32751
    4 Days on yellowkey

    $979,000 | Single Family Home | 4 beds | 3.5 baths | 2 gar

    Beautiful and spacious home at 1281 Wellington Terrace featuring high beam ceilings and elegant tile floors throughout. The open layout offers wonderful natural light and two master bedrooms, perfect for flexible living. New windows add comfort and efficiency. Enjoy a private, low-maintenance backyard ideal for relaxing or entertaining. Located in a beautiful neighborhood just minutes from Winter Park shopping and dining, with easy access to I-4 for convenient commuting.

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    Listing is courtesy of: LISTED SIMPLY

  • 921 N THISTLE LN, MAITLAND, FL - MLS# R4911080

    HIGHLAND PARK ESTATES - R4911080 - 921 N THISTLE LN, MAITLAND, FL 32751
    7 Days on yellowkey

    $1,049,000 Reduced | Single Family Home | 4 beds | 3.0 baths | 2 gar

    Central location, fully renovated, A-rated schools, a resort-style pool - this Dommerich home checks every box - and it is move-in ready, turnkey for your lifestyle. Situated in one of Central Florida’s most sought-after neighborhoods for over 60 years, Dommerich is known for its top-rated schools, tree-lined streets, parks, and unmatched convenience. This home sits right in the heart of it all. Originally built in 1967 and thoughtfully reimagined in a top-to-bottom renovation completed in 2019, the property blends classic charm with modern design and systems. Major updates include roof, HVAC, plumbing, electrical, windows, doors, insulation, appliances, kitchen, primary wing addition, natural gas connection, and a Rinnai tankless water heater. Inside, the open-concept living and dining spaces flow seamlessly to a designer pool and screened patio, creating an ideal indoor-outdoor lifestyle. The modern kitchen features extensive cabinetry with drawer-based storage, a coffee bar, and easy access to the garage and main living areas. A standout feature is the 2019-built primary suite addition, offering vaulted ceilings, a custom walk-in closet, en-suite bath, laundry, utility closet, and direct access to the pool area. The home also includes a second primary bedroom with its own en-suite bath that doubles as a pool bath, plus two additional bedrooms and a shared hall bath. The curb appeal is anchored by a mature, storybook-style shade tree, setting the tone for the character found throughout the property. Enjoy a short walk to the schools on a secluded sidewalk or take in the open sports fields across the street and Maitland Community park a few streets over.

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    Listing is courtesy of: VISTA NATIONAL MANAGEMENT INC

  • 2809 WAUMPI TRL, MAITLAND, FL - MLS# O6399820

    DOMMERICH HILLS 6TH ADD - O6399820 - 2809 WAUMPI TRL, MAITLAND, FL 32751
    8 Days on yellowkey

    $745,000 | Single Family Home | 5 beds | 3.0 baths | 2 gar

    Completely Remodeled 2026 | Single-Story | Split Floorplan | The redesigned kitchen features 42" shaker cabinetry, Calcutta quartz countertops, a marble backsplash, and new stainless steel Fisher & Paykel appliances. Bathrooms have been completely remodeled with updated finishes. Luxury vinyl flooring extends through all common areas, complemented by LED recessed lighting and updated fixtures throughout. The open layout provides clear sight-lines between the kitchen and family room, creating a connected main living area. The pavers meet manicured lawns and fresh landscaping for a clean, contemporary finish that is 100% move-in ready. Additional features include an interior laundry room and a fully fenced backyard with a pool. Enjoy being just minutes from Park Avenue, Lake Lily, and Maitland City Centre where you'll find farmers markets, local dining, and boutique shopping. With easy access to I-4, 417, and the Maitland Exchange, you're well connected to everything Central Florida has to offer.

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    Listing is courtesy of: EXP REALTY LLC

  • 2113 FALKNER RD, MAITLAND, FL - MLS# V4948473

    WINFIELD - V4948473 - 2113 FALKNER RD, MAITLAND, FL 32751
    8 Days on yellowkey

    $399,900 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Under contract-accepting backup offers. Welcome to this beautifully maintained 3-bedroom, 2-bathroom home with a 2-car garage, nestled in the desirable community of Maitland. Recently installed laminate flooring and a freshly painted interior enhance the home’s comfort and style—perfect for Central Florida living. Step inside to a bright, open-concept layout where the kitchen and living areas flow seamlessly together—ideal for both everyday living and entertaining. The kitchen is a true highlight, showcasing granite countertops, stainless steel appliances, ample workspace, and generous cabinet storage, all overlooking the main living area. Natural light fills the home through sliding glass doors that open to a spacious, fully fenced backyard—perfect for entertaining, relaxing, or enjoying Florida’s year-round sunshine. The primary suite welcomes you with an elegant double-door entry and features a well-appointed en-suite bathroom with generous counter space, a separate shower and soaking tub, and a large walk-in closet. Ideally located just minutes from RDV Sportsplex and its popular Ice Den, with shopping, dining, and everyday conveniences just 10 minutes away. Outdoor enthusiasts will appreciate the close proximity to Wekiwa Springs State Park, known for its crystal-clear springs, kayaking, swimming, and scenic trails. Don’t miss your opportunity to own this move-in ready home in desirable Maitland—schedule your private showing today! **Please allow 2 business days for a response from the seller. Seller’s preferred title company is BCHH, Inc.**

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    Listing is courtesy of: LOCAL LIVING REALTY GROUP

  • 1665 KING ARTHUR CIR, MAITLAND, FL - MLS# O6399064

    KINGS ROW - O6399064 - 1665 KING ARTHUR CIR, MAITLAND, FL 32751
    9 Days on yellowkey

    $1,100,000 | Single Family Home | 4 beds | 2.5 baths | 2 gar

    Under contract-accepting backup offers. 1665 King Arthur Circle

    Contact Yellowkey Agent

    Listing is courtesy of: KELLER WILLIAMS WINTER PARK

  • 51 OAKLEIGH LN, MAITLAND, FL - MLS# O6399404

    OAKLEIGH THIRD ADD - O6399404 - 51 OAKLEIGH LN, MAITLAND, FL 32751
    9 Days on yellowkey

    $1,240,000 | Single Family Home | 4 beds | 4.0 baths | 2 gar

    Come see 51 Oakleigh Ln, a functional residence arranged for everyday practicality. A comfortable living space features a fireplace. The kitchen includes an accent backsplash and all stainless steel appliances. The primary bedroom has a walk in closet, and its bathroom features double sinks and a separate tub and shower. Outside, a covered patio connects to an in ground pool within a fenced in backyard. This property is a must-see for comfort and outdoor living. Included 100-Day Home Warranty with buyer activation

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    Listing is courtesy of: OPENDOOR BROKERAGE LLC

  • 354 HICKORY DR, MAITLAND, FL - MLS# O6398112

    DRUID HILLS PARK - O6398112 - 354 HICKORY DR, MAITLAND, FL 32751
    10 Days on yellowkey

    $375,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Under contract-accepting backup offers. Multiple offers received, asking for highest and best before Sunday, April 19th at 5pm! Welcome Home to 354 Hickory Drive — Where Your Next Chapter Begins! Nestled in the friendly Druid Hills community of Maitland, FL, this beautifully renovated 3-bedroom, 2-bathroom home is the perfect place to plant roots and make lasting memories. Whether you're buying your first home or looking for the ideal space to grow your family, this one was made for you. The open-concept floor plan makes everyday life easy and fun — from homework at the kitchen table to hosting friends and family on the weekends. The fully updated kitchen, renovated bathrooms, and new flooring throughout mean you can move right in and start living without the stress of costly upgrades. When it's time to unwind or play, the huge enclosed screen porch and deck deliver the outdoor lifestyle Florida is known for — shaded space to play or a relaxed spot to decompress after a long day. The .20-acre lot gives the whole family room to run, garden, or just enjoy the Florida sunshine. Big-ticket items are already taken care of, so you can focus on building your future rather than your repair list — featuring a 2025 AC, 2024 tankless water heater, 2023 water softener, whole house water filtration system, 2018 roof, and propane tank that feeds the water heater. For added convenience a stub out is readily available for future appliances. Located in the heart of Maitland with easy access to top-rated schools, family-friendly parks, local shopping and dining, major commuter routes — everything you need is right at your doorstep. Schedule your showing today!

    Contact Yellowkey Agent

    Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY

  • 344 BANYAN DR, MAITLAND, FL - MLS# O6397900

    DRUID HILLS PARK - O6397900 - 344 BANYAN DR, MAITLAND, FL 32751
    14 Days on yellowkey

    $398,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    STUNNING MODERN REVIVAL IN THE HEART OF MAITLAND. Welcome to 344 Banyan Drive, where classic Maitland charm meets contemporary elegance. Experience the pinnacle of move-in-ready luxury at 344 Banyan Dr. This impeccably renovated residence has been transformed from top to bottom with sophisticated finishes and meticulous attention to detail. The open-concept interior shines with all-new flooring, contemporary baseboards, and a fresh, designer paint palette. The newly renovated kitchen is a true showstopper, boasting new custom cabinetry, sleek stone countertops, a stylish tile backsplash, and a premium stainless steel appliance package. Both the living spaces and the fully renovated bathrooms feature all-new designer lighting that creates a warm, inviting ambiance throughout. Every inch of this home feels brand new. Don't miss your chance to own a masterpiece in 32751!

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    Listing is courtesy of: REMAX SUNSTATE REALTY

  • 2466 FIELDINGWOOD RD, MAITLAND, FL - MLS# O6396883

    ENGLISH WOODS - O6396883 - 2466 FIELDINGWOOD RD, MAITLAND, FL 32751
    14 Days on yellowkey

    $599,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar

    Welcome to 2466 Fieldingwood Rd, a fully re-imagined pool home in Maitland, FL. This 4 bedroom, 2 bathroom home has been completely renovated from top to bottom with a fresh, modern feel that is move-in ready and designed for today’s lifestyle. From the moment you arrive, you will notice the clean exterior, updated landscaping, and quiet street that sets the tone for the rest of the home. ALL major systems have been updates: Roof 2022, Plumbing 2024, Hot Water Heater 2024, AC 2016, and newer pool equiptment. Inside, the layout flows effortlessly with light-filled living spaces, updated flooring, and a bright, open feel throughout. The kitchen and main living areas connect seamlessly, making it perfect for both everyday living and entertaining. Step outside to your private backyard retreat featuring a newly refreshed pool and spacious deck area. This is the kind of space that feels like Florida living should. Whether you are hosting friends or enjoying a quiet evening at home, this backyard delivers. The bedrooms offer comfortable, flexible space for families, guests, or a home office, while the primary suite provides a clean and calming place to unwind. Located in English Estates, you are just minutes from Winter Park with easy access to 17-92, 436, and Red Bug Lake Road. Commuting is simple with quick access to I-4 and the express lane entrance, getting you to downtown Orlando efficiently. If you are looking for a fully updated home with a pool in a central location that actually makes your day-to-day life easier, this is one you need to see in person.

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    Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY

  • 101 MARINER WAY, MAITLAND, FL - MLS# O6396663

    MAITLAND ISLE - O6396663 - 101 MARINER WAY, MAITLAND, FL 32751
    15 Days on yellowkey

    $769,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar

    Under contract-accepting backup offers. Welcome to an exceptional residence in the Maitland Isle subdivision, where timeless elegance meets modern comfort. This beautifully updated four-bedroom, two-bath home spans 2,413 square feet and offers exclusive private lake access to Lake Maitland on the prestigious Winter Park Chain of Lakes. Designed for refined living and effortless entertaining, the home features a thoughtfully curated interior with upgraded finishes, including laminate flooring, enhanced baseboards, wet bar in family room and a seamless, light-filled layout. The kitchen, enhanced with quality wood cabinetry, flows seamlessly into the main living areas, while generously sized split bedroom plan provides flexibility for family, guests or a home office. A comprehensive list of upgrades reflects pride of ownership such as a newer roof (2020), resurfaced pool (2020), advanced air-conditioning system with Enviracare Elite air purification (2019), updated electrical panels (2012), replumbing (2006) and a water heater (2022). More recent enhancements include full interior and exterior painting (2025), a newly installed wooden fence and a serviced sprinkler system with a new impeller (2026). Outdoors, enjoy a private retreat with a sparkling pool and covered deck with an outdoor entertainment area, ideal for year-round Florida living. Residents of Maitland Isle benefit from exclusive access to Lake Maitland, offering a rare opportunity for boating and waterfront recreation within one of Central Florida’s desirable communities. Ideally in a top-rated school district and just a short distance to the charm of downtown Maitland, this home delivers a lifestyle of convenience, prestige and tranquility. A rare offering where location, quality and lifestyle converge.

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    Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY

  • 2130 DELORAINE TRL, MAITLAND, FL - MLS# O6397018

    HIGHLAND PARK ESTATES FIRST ADD - O6397018 - 2130 DELORAINE TRL, MAITLAND, FL 32751
    17 Days on yellowkey

    $829,000 Reduced | Single Family Home | 3 beds | 2.0 baths | 2 gar

    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.

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    Listing is courtesy of: COMPASS FLORIDA LLC

  • 1662 BOBTAIL DR, MAITLAND, FL - MLS# O6395347

    WINFIELD UNIT 2 - O6395347 - 1662 BOBTAIL DR, MAITLAND, FL 32751
    17 Days on yellowkey

    $525,000 | Single Family Home | 5 beds | 2.5 baths | 2 gar

    Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to your new home in the vibrant Winfield neighborhood. With close to $70,000 in recent upgrades, this spacious 5-bedroom, 2.5-bathroom home offers 2,330 square feet, ideal for those needing extra space. Enjoy cooking in the brand new remodeled kitchen, featuring soft close cabinetry, upgraded fixtures and lighting. You'll love the three renovated bathrooms too, especially the primary suite which has an extra large soaking tub, dual vanities and high end counters and fixtures. The open floor plan allows natural light to fill the home, showcasing the beautiful wide plank luxury flooring throughout the main living spaces. Step outside to an inviting screened patio, perfect for relaxing or entertaining. Plus the fully fenced backyard is perfect for letting your dogs run free or for a quick game of soccer or tag football. The home is freshly paint inside and out and has new landscaping and fresh sod. Situated near the Maitland Business District and Orlando Sportsplex, you will have quick access to shopping, dining, and entertainment. The Maitland Art Center is also close by. This home suits those wanting a beautiful and serene neighborhood, situated just outside the city bustle, while still being near expressways and top restaurants in Winter Park and Maitland. Make an appointment today!

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    Listing is courtesy of: MAINFRAME REAL ESTATE

  • 361 HICKORY DR, MAITLAND, FL - MLS# O6395765

    DRUID HILLS PARK - O6395765 - 361 HICKORY DR, MAITLAND, FL 32751
    22 Days on yellowkey

    $369,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    One or more photo(s) has been virtually staged. Welcome to 361 Hickory Drive, a truly special opportunity in a quiet, well-established community in the heart of Maitland. This charming home offers the perfect blend of comfort, mid-century historic charm and an unbeatable location making it ideal for those seeking both tranquility and convenience. Set on an oversized lot, this property provides ample space to entertain or enjoy the peaceful surroundings. The neighborhood is known for its quiet atmosphere with NO HOA, giving you the freedom to truly make this home your own without added restrictions. Upon walking in, you are greeted with an open concept living room space with the dining room to the left. The kitchen features ample cabinet space and a separate cooktop. The 2nd and 3rd bedrooms are generously sized with the primary including an en-suite bathroom. A BRAND NEW ROOF will be installed prior to closing, offering peace of mind. Upgrades include a New Water Heater (2026) and A/C(2019) ensuring comfort and efficiency. This home is also zoned in Top Rated Seminole County School Districts. Whether you're looking to settle into a serene neighborhood or invest in a property with strong fundamentals, this one checks all the boxes. Don’t miss your chance to call this Maitland gem home today!

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    Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS

  • 2112 CHIPPEWA TRL, MAITLAND, FL - MLS# O6394702

    DOMMERICH HILLS - O6394702 - 2112 CHIPPEWA TRL, MAITLAND, FL 32751
    22 Days on yellowkey

    $965,000 | Single Family Home | 4 beds | 3.5 baths | 2 gar

    LONG AWAITED ARRIVAL IN DESIRABLE MAITLAND SUBDIVISION This beautiful, impeccably maintained and updated four bedroom three and a half bath pool home absolutely has it all! 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 four 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 double 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 newly resurfaced pool and brick paver deck, open patio and super fun gazebo with gas grill and nighttime lighting for entertaining! This home is fully supported by a full 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. Beautiful landscape and outdoor lighting add to its charm and warmth. THIS opportunity does not come along often. Look forward to meeting you there!

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    Listing is courtesy of: COLDWELL BANKER REALTY

  • 551 RUFFEL ST, MAITLAND, FL - MLS# S5146986

    CLARK HOMES ACRES - S5146986 - 551 RUFFEL ST, MAITLAND, FL 32751
    23 Days on yellowkey

    $299,900 Reduced | Single Family Home | 3 beds | 1.5 baths | 1 car

    Situated at the end of a cul-de-sac in the Eatonville/Maitland area, this home offers a great opportunity for a first-time buyer or someone looking to downsize. According to the owner, the property was rehabilitated by the county in 2017, with updates that included the HVAC, plumbing, and electrical systems, and the roof was replaced approximately 10 years ago. Conveniently located near I-4 and Winter Park, this home is just minutes from local eateries, the library, and public transportation.

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    Listing is courtesy of: RESIDENTIAL MATCHMAKERS LLC

  • 1241 MANCHESTER RD, MAITLAND, FL - MLS# S5146896

    ENGLISH ESTATES UNIT 2 - S5146896 - 1241 MANCHESTER RD, MAITLAND, FL 32751
    24 Days on yellowkey

    $625,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar

    Step into this beautifully renovated 4-bedroom, 2-bathroom home located in the heart of Maitland, where space, comfort, and modern design come together effortlessly. From the moment you walk in, you’ll notice the bright open-concept layout that creates a warm and inviting atmosphere, perfect for both everyday living and unforgettable family moments. The seamless flow between the living, dining, and kitchen areas makes this home ideal for gatherings, entertaining, or simply enjoying time at home. Natural light fills the space, enhancing every detail and making each room feel open, airy, and welcoming. Each bedroom offers comfort and versatility, whether you need space for a growing family, a home office, or guest accommodations. The thoughtful updates throughout the home provide a true move-in ready experience. As part of the renovations, the seller has a new roof scheduled, adding even more value for the future owner. Enjoy the charm and convenience of living in Maitland, with easy access to shopping, dining, parks, and major roadways. This is more than just a house—it’s a place where everyday life feels a little more special.

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    Listing is courtesy of: LA ROSA REALTY LLC

  • 2600 MOHAWK TRL, MAITLAND, FL - MLS# O6392479

    DOMMERICH HILLS SECOND ADD - O6392479 - 2600 MOHAWK TRL, MAITLAND, FL 32751
    24 Days on yellowkey

    $669,000 | Single Family Home | 4 beds | 2.5 baths | 3 gar

    Dommerich Hills – Maitland Positioned in the heart of Maitland, this inviting single-story home in the highly desirable Dommerich Hills community combines comfort, character, and location. Offered for the first time in 60 years, this property reflects true pride of ownership and long-term care. Set on a spacious .24-acre lot, the home offers 4 bedrooms, 2.5 baths, and 2,265 sq. ft. of living space. A timeless brick exterior and side-entry two-car garage create strong curb appeal, while the single-level floor plan provides effortless everyday living. The kitchen flows naturally into the connected living and dining areas, promoting an open, comfortable layout perfect for gatherings or flexible work-from-home use. Enjoy a fully fenced backyard great for pets, gardening, play, or weekend entertaining in your own outdoor retreat. Recent updates include: roof (Nov 2021), HVAC (May 2023), garage door (Apr 2022), and now connected to the city sewer (Nov 2025). Dommerich Hills is a well-established, tree-lined neighborhood known for its spacious lots, mid-century architecture, and strong sense of community. Zoned for Dommerich Elementary, Maitland Middle, and Winter Park High, with the convenience of walking or biking to nearby schools. Minutes from Downtown Winter Park dining, boutique shopping, and easy access to major roadways and everyday conveniences. A rare opportunity to own a meticulously maintained home in one of Maitland’s most established and sought-after communities—offering the perfect blend of location, lifestyle, and long-term value.

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    Listing is courtesy of: FLORIDA ONE REAL ESTATE LLC

  • 210 ALPINE DR, MAITLAND, FL - MLS# O6395056

    SUNSET RIDGE - O6395056 - 210 ALPINE DR, MAITLAND, FL 32751
    24 Days on yellowkey

    $550,000 | Single Family Home | 2 beds | 2.0 baths | 1 gar

    Under contract-accepting backup offers. Don't miss this Great opportunity in the Maitland-Winter Park area! There's Potential for Renovation, Expansion or Development with this property. Imagine the Improvements that can be made for the Future. This is a One Owner Home held be the same family since the 1960s. New roof in 2022. The adjacent property at 220 Alpine is also available for purchase.

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    Listing is courtesy of: PREMIUM PROPERTIES R.E SERVICE

  • 200 SPARTAN DR, MAITLAND, FL - MLS# O6394981

    COOL-MORE SUB - O6394981 - 200 SPARTAN DR, MAITLAND, FL 32751
    24 Days on yellowkey

    $540,000 | Single Family Home | 3 beds | 2.0 baths

    More photos to come soon! Welcome to 200 Spartan Dr, a beautifully updated 3/2 (with bonus room and large laundry room) pool home in the heart of Maitland. The interior has been thoughtfully opened up by removing walls between the living area and kitchen, creating a much more spacious and modern feel, and a large island was added to make the kitchen the center of the home. The home also features a bonus room offering great flexibility for a home office, workout space, or hobby room. Outside, enjoy a private pool and backyard space perfect for relaxing or entertaining. Conveniently located near shopping, dining, parks, and major roadways, this home offers comfort, functionality, and a great Maitland location. Roof, HVAC, and Water heater from 2018.

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    Listing is courtesy of: EXP REALTY LLC

  • 502 OAK LN, MAITLAND, FL - MLS# O6394681

    OAKLAND SHORES - O6394681 - 502 OAK LN, MAITLAND, FL 32751
    24 Days on yellowkey

    $629,000 | Single Family Home | 3 beds | 3.5 baths | 2 gar

    Welcome to 502 Oak Lane in Maitland, a beautifully updated pool home that blends comfort, character, and peace of mind. This fully improved 3 bedroom, 3.5 bathroom home has been thoughtfully updated throughout, including the replacement of the cast iron plumbing, offering both charm and important system improvements. Inside, you will find a well designed layout with spacious living areas, updated finishes, and plenty of natural light. Each bedroom offers its own bathroom, creating privacy and flexibility for guests or family. The home has been meticulously maintained and improved, making it truly move in ready. Step outside to your private backyard oasis featuring a pool, perfect for relaxing afternoons or entertaining friends and family. Located on a quiet street in Maitland, this home offers a great combination of location, updates, and lifestyle. This is a rare opportunity to own a fully improved pool home in one of Maitland’s most desirable areas.

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    Listing is courtesy of: KRESSLER REAL ESTATE

  • 1750 POCAHONTAS PATH, MAITLAND, FL - MLS# O6394358

    DOMMERICH ESTATES 1ST ADD - O6394358 - 1750 POCAHONTAS PATH, MAITLAND, FL 32751
    25 Days on yellowkey

    $659,000 Reduced | Single Family Home | 3 beds | 2.0 baths | 1 gar

    Set along a quiet, tree-lined street in Maitland, this 3 bedroom, 2 bathroom home with 1,922 square feet captures the essence of mid-century modern design with a fresh, updated edge. Clean lines, open flow, and a strong connection to the outdoors define the home from the moment you step inside. The living spaces feel intentional and uncluttered, with natural light highlighting the architectural simplicity that makes this style so enduring. An updated kitchen anchors the home with modern finishes and functionality, complemented by an eat-in dining area that invites everyday gathering. A dedicated bar area adds character and ease for entertaining, creating a space that feels both relaxed and refined. A separate office/flex space provides flexibility for today’s lifestyle, offering a quiet place to work or create without disrupting the flow of the home. Updated bathrooms carry a cohesive, minimalist design throughout, staying true to the home’s architectural roots. The outdoor space continues the story. Minimalist landscaping and open, usable areas create a calm and private setting that feels like a natural extension of the interior. It is a setting designed for both quiet mornings and easy evenings with friends. An optional HOA provides deeded lake access, adding a lifestyle component that is increasingly hard to find. All of this is paired with access to some of the most highly regarded schools in Central Florida and a location just minutes from Park Avenue, dining, and shopping. This is not just a home with style. It is a home with intention.

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    Listing is courtesy of: COMPASS FLORIDA LLC

  • 2801 WAUMPI TRL, MAITLAND, FL - MLS# S5146322

    DOMMERICH HILLS 6TH ADD - S5146322 - 2801 WAUMPI TRL, MAITLAND, FL 32751
    32 Days on yellowkey

    $864,900 Reduced | Single Family Home | 5 beds | 3.0 baths | 2 gar

    Welcome to Dommerich Hills! This fully renovated property delivers clean modern design with real functionality with NO HOA with a paver driveway, and double-door entry set the tone from the start. Inside, a bright open layout is anchored by a statement kitchen featuring sleek cabinetry, stainless steel appliances, and a waterfall island with custom wood detailing. The bathrooms follow with spa-inspired finishes, glass-enclosed showers, and modern fixtures throughout. Step outside to a covered lanai overlooking a private pool and expansive paver patio built for true Florida indoor outdoor living. Move in ready and designed to stand out, Located just minutes major highways, premium shopping, dining, and entertainment, this home delivers convenience and lifestyle all in one to the city beautiful. call to make a appointment to see this amazing Home.

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    Listing is courtesy of: AVANTI WAY REALTY LLC





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