Maitland, FL Homes for Sale with Garage

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  $1,249,900

  • 4 Beds
  • 4 Baths
  • 3,902 Sq Ft

  873 Cranes Ct, Maitland, FL 32751

  Beautifully Maintained Original-Owner Pool Home in Gated Lake Sybelia Cove. Pride of ownership shines throughout this beautifully maintained original-owner home tucked away on a quiet cul-de-sac in the gated community of Sybelia Cove. Offering 4 bedrooms, 4 bathrooms, a side-entry 3-car garage, and 3,902 square feet, this spacious residence blends timeless design with thoughtful updates in one of

  Chris Creegan CREEGAN GROUP

  873 Cranes Ct, Maitland, FL 32751
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  /26

  $509,900

  • 3 Beds
  • 2 Baths
  • 1,683 Sq Ft

  370 Sultana Ln, Maitland, FL 32751

  Welcome to 370 Sultana Lane, a beautifully renovated 3-bedroom, 2-bathroom home located in the highly desirable Druid Hills community of Maitland. With over $60,000 in thoughtful upgrades, this move-in-ready residence offers modern comfort without the hassle of future projects. Step inside to a fully reimagined open floor plan designed for both everyday living and entertaining. A redesigned foyer

  Melissa Osborne EQUITYPRO LLC

  370 Sultana Ln, Maitland, FL 32751
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  /38

  $639,000

  Open Sun 1PM - 4PM $40K 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.The living spaces feel intentional and uncluttered, with natural light highlighting the

  Brian Rotenberger COMPASS FLORIDA LLC

  1750 Pocahontas Path, Maitland, FL 32751
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  /39

  $670,000

  Open Sun 1PM - 3PM

  • 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. A private spa pool 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 mind with a dedicated laundry room featuring a brand-new washer

  Sarah Tomlinson COMPASS FLORIDA LLC

  910 Gamewell Ave, Maitland, FL 32751
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  /43

  $379,000

  • 3 Beds
  • 2.5 Baths
  • 1,674 Sq Ft

  1393 Benevolent St, Maitland, FL 32751

  This beautiful Maitland Florida town home feels like living in a gated resort! 3 bedrooms, 2 1/2 baths, plus garage and loaded with upgrades including hardwood floors on both levels, crown molding, tall wood cabinets, stone counters and so much more. Welcoming entry foyer with half bath, kitchen with island sink, large breakfast bar, stainless appliances, granite counters and custom backsplash.

  Daniel Rencher RENCHER REALTY GROUP

  1393 Benevolent St, Maitland, FL 32751
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  /31

  $725,000

  $59K PRICE DROP

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

  1732 Ridgewood Ave Unit S, Maitland, FL 32751

  This custom two-story townhome delivers what most properties in this category simply don’t; space, light, and a layout that actually makes sense. Open, airy, and thoughtfully designed, every detail feels intentional. Perfectly positioned between Maitland and Winter Park, you’re just minutes from Park Avenue, Winter Park Village, and some of the best dining and shopping in Central Florida. Step

  Brandon Geers COMPASS FLORIDA LLC

  1732 Ridgewood Ave Unit S, Maitland, FL 32751
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  /52

  $599,900

  $150K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 2,484 Sq Ft

  933 and 935 Robinhood Ct, Maitland, FL 32751

  HUGE PRICE DROP! Whole Duplex. 6/4 (3 bed 2 bath in each unit). The Duplex is located in a cul-de-sac on a large lot that backs up to walking trail. Oakmont neighborhood has access directly to Sunrail Maitland Station. No HOA. Unit 933 has a fireplace for those cold Florida winters. The backyard is fully fenced and has an above-the-ground pool and a fully functionable bar with electric and

  Olaf Stenger KGV REALTY GROUP

  933 and 935 Robinhood Ct, Maitland, FL 32751
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  /67

  $949,900

  Open Sun 2PM - 4PM

  • 4 Beds
  • 2.5 Baths
  • 2,312 Sq Ft

  1851 Huron Trail, Maitland, FL 32751

  Beautifully updated 4-bedroom, 2.5-bath home in the heart of Dommerich Estates — one of Maitland’s most loved neighborhoods known for its top-rated schools, tree-lined streets, and access to the Winter Park Chain of Lakes. Just steps from the neighborhood lake lot and nearby Maitland Community Park, this home offers over 2,300 square feet with warm wood flooring, crisp light walls, and thoughtful

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  1851 Huron Trail, Maitland, FL 32751
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  /39

  $1,895,000

  Open Sun 2PM - 4PM

  • 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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  /53

  $998,000

  Open Sun 1PM - 3PM $52K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,625 Sq Ft

  1001 Versailles Ct, Maitland, FL 32751

  One or more photo(s) has been virtually staged. Nestled within the quiet, established community of Versailles, this exceptional residence invites you to slow down and savor the good life. Offering over 3,600 sq. ft., this home features 4 spacious bedrooms and 3 full baths, with a layout that is both functional and flexible. The PRIMARY SUITE is conveniently located on the MAIN FLOOR and features

  Heather Frazee FANNIE HILLMAN & ASSOCIATES

  1001 Versailles Ct, 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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  /63

  $965,000

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

  2112 Chippewa Trail, Maitland, FL 32751

  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

  Laura Heidrich COLDWELL BANKER REALTY

  2112 Chippewa Trail, Maitland, FL 32751
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  /22

  $585,000

  $15K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,959 Sq Ft

  2453 Worthington Rd, Maitland, FL 32751

  A lovely well designed 4bdr. 2 bath home with an eat in kitchen open to a spacious family rm. A formal din.rm. and formal lvg.rm. are ready for any occasion. The long 2 lane brick driveway can accommodate multiple vehicles. Nearby schools for all levels and the amenities for recreation and entertainment are too numerous to list. This house should be added to your list when searching for your new

  Stephen Hachey REALTY OF RIVERVIEW LLC

  2453 Worthington Rd, Maitland, FL 32751
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  /55

  $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. Perfectly positioned between Lake Sybelia and Lake Catherine, this one owner estate offers a rare blend of sophistication, comfort, and versatility with five

  Jo-Ann Lamar PREMIER SOTHEBY'S INTL. REALTY

  755 Cranes Ct, Maitland, FL 32751
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  /46

  $625,000

  • 4 Beds
  • 2 Baths
  • 2,038 Sq Ft

  1241 Manchester Rd, Maitland, FL 32751

  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,

  Ricardo Araque LA ROSA REALTY LLC

  1241 Manchester Rd, 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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  /39

  $485,000

  • 3 Beds
  • 2.5 Baths
  • 1,652 Sq Ft

  245 Quayside Cir, Maitland, FL 32751

  Welcome to The Moorings on Lake Maitland, one of the most in-demand communities in the area. Consider this unit, 3-bedrooms and 2-1/2 baths, approximately 1700 square feet of living space with a 1-car garage, and overlooking the beautiful peaceful courtyard, to be your blank slate. Gleaming wood floors and fresh painted throughout, it is just waiting for you to make it your own. You'll love this

  Sue Gilman KELLER WILLIAMS WINTER PARK

  245 Quayside Cir, Maitland, FL 32751
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  /13

  $527,300

  $23K PRICE DROP

  • 2 Beds
  • 2 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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  /30

  $490,000

  $10K PRICE DROP

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

  612 Green Meadow Ave, Maitland, FL 32751

  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

  Stacy Wayne FLORIDA HOME TEAM REALTY LLC

  612 Green Meadow Ave, Maitland, FL 32751
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  /39

  $521,800

  Open Sun 11AM - 2PM

  • 4 Beds
  • 2 Baths
  • 1,864 Sq Ft

  1905 Poinsetta Ln, Maitland, FL 32751

  Big vibes and even bigger possibilities! Say Hello to easy Florida living! This stylish 4-bedroom, 2-bath Maitland home delivers bright natural light, functional living spaces, and room for everyone to spread out. Whether you’re hosting game nights, working from home, or enjoying quiet mornings with coffee on the patio, this home checks all the boxes. A backyard perfect for entertaining and

  Michelle Terry SYNCHRONICITY REAL ESTATE SOLUTIONS

  1905 Poinsetta Ln, Maitland, FL 32751

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