Maitland, FL Homes for Sale with Garage

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  /39

  $619,000

  $60K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,922 Sq Ft

  1750 Pocahontas Path, Maitland, FL 32751

  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. Major updates include the kitchen in 2019, bathrooms in 2021, Roof 2022, and HVAC in 2024. The living

  Brian Rotenberger COMPASS FLORIDA LLC

  1750 Pocahontas Path, Maitland, FL 32751
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  /45

  $355,000

  • 4 Beds
  • 2 Baths
  • 1,707 Sq Ft

  2401 Legacy Lake Dr Unit 2401, Maitland, FL 32751

  All roads lead to Visconti East! Located in Maitland, bordering nearby scenic Winter Park (Park Ave./ Rollins College) this distinctive 3 story, 4 Bed/2.5 Bath townhome is situated directly off of I-4 and SR414, within 10 minutes to Downtown Orlando, Park Avenue, and close access to SR429, Winter Garden, and North Orlando. This home offers a one-of-a-kind floor plan with the entry foyer, hall

  Trace Christian, III COLDWELL BANKER REALTY

  2401 Legacy Lake Dr Unit 2401, Maitland, FL 32751
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  /39

  $645,000

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,214 Sq Ft

  910 Gamewell Ave, Maitland, FL 32751

  Tucked away in the heart of Maitland, this thoughtfully updated three-bedroom, two bath residence blends everyday comfort with meaningful, modern upgrades. Freshly painted interior (June 2026) and a private spa pool WITH BRAND NEW POOL PUMP creates a serene outdoor retreat—perfect for unwinding or entertaining year-round in true Florida style. Inside, the home offers both function and peace of

  Sarah Tomlinson COMPASS FLORIDA LLC

  910 Gamewell Ave, Maitland, FL 32751
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  /97

  $850,000

  • 4 Beds
  • 2 Baths
  • 1,870 Sq Ft

  109 Kyle Dr, Maitland, FL 32751

  A tropical retreat in Minnehaha Shores with deeded lake access to the Winter Park Chain of Lakes. Tree-lined streets welcome you to this beautifully reimagined four-bedroom, two-bath split-plan home with coastal influences throughout. Formal living, dining and family spaces blend seamlessly together, creating great flexibility in layout. French doors line the back of the home and open to the

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  109 Kyle Dr, Maitland, FL 32751
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  /80

  $1,795,000

  • 3 Beds
  • 3 Baths
  • 2,351 Sq Ft

  631 Lake Catherine Dr, Maitland, FL 32751

  Welcome to an extraordinary lakefront sanctuary at 631 Lake Catherine Drive, where sophisticated luxury meets serene waterfront living in one of Maitland's most coveted locations. This meticulously renovated residence, rebuilt down to the studs, represents the pinnacle of modern Florida elegance and is offered at $1,795,000. Positioned on an elevated lot overlooking the sparkling waters of Lake

  Kelly Price KELLY PRICE & COMPANY LLC

  631 Lake Catherine Dr, Maitland, FL 32751
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  /30

  $429,900

  • 3 Beds
  • 2 Baths
  • 1,651 Sq Ft

  1010 Winderley Place Unit 149, Maitland, FL 32751

  This beautifully positioned residence offers an open and inviting layout designed for easy living and entertaining. Enjoy peaceful water views of Lake Destiny with no rear neighbors, creating a private backdrop and a rare sense of space and tranquility. Whether relaxing indoors or stepping outside, the serene setting delivers a true sense of comfort and escape. The home also features a spacious

  Hafid Boujidi GENSTONE REALTY

  1010 Winderley Place Unit 149, Maitland, FL 32751
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  /18

  $1,299,000

  • 5 Beds
  • 4 Baths
  • 2,695 Sq Ft

  2491 Lauder Dr, Maitland, FL 32751

  Completely reimagined and renovated, this artfully crafted stunning 5-bedroom, 4-bath residence offers approximately 2,695 square feet of on a spacious corner lot in one of Maitland's most desirable established neighborhoods. The home features an exceptional blend of modern design, luxury finishes, and functional living spaces, including a sparkling pool and expansive outdoor entertaining areas.

  Bob Holston, Jr HOLSTON PROPERTIES & DEV., INC

  2491 Lauder Dr, Maitland, FL 32751
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  /46

  $419,000

  $11K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,370 Sq Ft

  1291 Oxford Rd, Maitland, FL 32751

  Virtually Staged. HUGE PRICE IMPROVEMENT!!! Move-In Ready Maitland Gem in English Estates! Welcome home to this charming 3-bedroom, 2-bath residence offering convenient one-story living in the highly desirable English Estates community. Blending modern updates with a touch of mid-century modern character, this home is truly turnkey. Step inside to find luxury vinyl plank and ceramic tile flooring

  Fran Zvaigzne COLDWELL BANKER REALTY

  1291 Oxford Rd, Maitland, FL 32751
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  /37

  $1,790,000

  $105K PRICE DROP

  • 4 Beds
  • 5 Baths
  • 4,478 Sq Ft

  1244 E Lake Colony Dr, Maitland, FL 32751

  Modern, mediterranean lakefront residence in one of Maitland’s most desirable GATED communities, positioned on a private cul-de-sac atop a natural rise. Set on over 1.3 acres with approximately 179 feet of frontage on Lake Jackson (ski lake), the property offers a rare combination of elevation, privacy and expansive water views in a central Maitland location with quick access to I-4, downtown

  Jennifer Sloan COMPASS FLORIDA LLC

  1244 E Lake Colony Dr, Maitland, FL 32751
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  /35

  $332,500

  $7K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,563 Sq Ft

  1010 Winderley Place Unit 127, Maitland, FL 32751

  Back on the market through no fault of the property. Recently appraised at $340,000 and inspections were completed without issue. A great opportunity for a qualified buyer seeking a smooth transaction and quick closing. Tucked into one of Maitland's most coveted lakefront enclaves, this beautifully updated townhome sits within a quietly maintained, tree-lined setting with direct access to Lake

  Don Harkins DON HARKINS REALTY LLC

  1010 Winderley Place Unit 127, Maitland, FL 32751
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  /20

  $308,000

  • 3 Beds
  • 2 Baths
  • 1,076 Sq Ft

  1074 Hamlet Dr, Maitland, FL 32751

  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

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  1074 Hamlet Dr, Maitland, FL 32751
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  /45

  $1,150,000

  • 5 Beds
  • 3.5 Baths
  • 3,857 Sq Ft

  900 Brightwater Cir, Maitland, FL 32751

  Welcome to the Premier community of Maitland Club. The paver walkway and covered front patio lead you into the spacious foyer, featuring the elegant formal living and dining rooms with hardwood floors, crown molding and plantation shutters. The Kitchen features Granite countertops, 42” cabinets and lots of natural light. The warm and inviting family room area offers a woodburning fireplace with

  David Alderman ENGEL & VOLKERS ORLANDO DR PHILLIPS

  900 Brightwater Cir, Maitland, FL 32751
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  /63

  $949,000

  $16K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,407 Sq Ft

  2112 Chippewa Trail, Maitland, FL 32751

  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

  Laura Heidrich COLDWELL BANKER REALTY

  2112 Chippewa Trail, Maitland, FL 32751
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  /31

  $559,900

  • 3 Beds
  • 2 Baths
  • 1,801 Sq Ft

  726 Forest Glen Ct, Maitland, FL 32751

  This beautifully redesigned and renovated move in ready pool home sits on a quiet cul-de-sac in desirable Maitland. Inside, the open floor plan features a brand-new kitchen with quartz countertops, shaker cabinetry, waterfall island, and stainless-steel appliances. Luxury flooring, remodeled baths, and modern finishes run throughout. Major updates include a new roof, newer HVAC, newer water

  Janet Garay FLORIDA REALTY OF MIAMI CORP

  726 Forest Glen Ct, Maitland, FL 32751
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  /31

  $489,900

  • 3 Beds
  • 2 Baths
  • 1,822 Sq Ft

  2155 Fennell St, Maitland, FL 32751

  Welcome to 2155 Fennell Street, a beautifully renovated pool home nestled in the desirable Maitland community. This move-in ready residence has undergone an extensive transformation, offering the perfect blend of modern elegance, functionality, and Florida lifestyle living. From the moment you arrive, you'll appreciate the brand-new roof, new driveway, fresh exterior paint, and impressive curb

  Deidre Rios TCA REALTY, LLC

  2155 Fennell St, Maitland, FL 32751
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  /54

  $1,395,500

  $100K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,566 Sq Ft

  755 Cranes Ct, Maitland, FL 32751

  One or more photo(s) has been virtually staged. Exceptional value meets timeless elegance in this incredible home nestled in the heart of Maitland, privately situated on a cul de sac within an exclusive gated enclave of custom residences. The Saltwater pool has a brand new sparkling finish! Perfectly positioned between Lake Sybelia and Lake Catherine, this one owner estate offers a rare blend of

  Jo-Ann Lamar PREMIER SOTHEBY'S INTL. REALTY

  755 Cranes Ct, Maitland, FL 32751
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  /30

  $575,000

  • 3 Beds
  • 2 Baths
  • 1,623 Sq Ft

  9001 Lake Charity Dr, Maitland, FL 32751

  Welcome to a rare opportunity in the beautiful neighborhood of Druid Hills in Maitland—this charming single-family home is on the market for the first time in 45 years. Built with solid block construction, this home offers exceptional durability, structural soundness, and reliable weather resistance, giving peace of mind for years to come. Situated on an expansive and highly desirable corner lot,

  Joseph Sipp KELLER WILLIAMS WINTER PARK

  9001 Lake Charity Dr, Maitland, FL 32751
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  /20

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,146 Sq Ft

  1033 Hamlet Dr, Maitland, FL 32751

  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

  Bennie Olivo BOX REAL ESTATE LLC

  1033 Hamlet Dr, Maitland, FL 32751
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  /13

  $527,300

  $23K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,328 Sq Ft

  210 Alpine Dr, Maitland, FL 32751

  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.

  Beth Hathaway PREMIUM PROPERTIES R.E SERVICE

  210 Alpine Dr, Maitland, FL 32751
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  /39

  $975,000

  • 3 Beds
  • 3 Baths
  • 2,192 Sq Ft

  119 Hollie Ct, Maitland, FL 32751

  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.

  Drew Belani COMPASS FLORIDA LLC

  119 Hollie Ct, Maitland, FL 32751
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  /36

  $849,900

  Open Sun 2PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 2,055 Sq Ft

  1783 Sunnyside Dr, Maitland, FL 32751

  Perfectly positioned between Maitland and Winter Park, this beautifully maintained 3-bedroom, 2.5-bath pool home offers an exceptional combination of charm, character, and an unbeatable location just minutes from the shops and restaurants of Park Avenue.Warm hardwood floors flow throughout the home, while the impressive two-story family room showcases soaring ceilings and a wood-burning

  Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  1783 Sunnyside Dr, Maitland, FL 32751
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  /37

  $799,000

  $51K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,175 Sq Ft

  2130 Deloraine Trail, Maitland, FL 32751

  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,

  Mario Zendeli COMPASS FLORIDA LLC

  2130 Deloraine Trail, Maitland, FL 32751

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