9,826

Maitland, FL Homes

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  • /42

    $945,000

    Pending
    • 5 Beds
    • 3 Baths
    • 3,370 Sq Ft

    624 Tuscarora Trail, Maitland, FL 32751

    Under contract-accepting backup offers. Welcome to this impressive 5-bedroom, 3-bath split-level POOL home in desirable Dommerich Hills, perfectly nestled on a generous 0.34-acre lot backing to a quiet creek and scenic green space.. Enjoy exceptional privacy and natural beauty with no rear neighbors, creating a peaceful backyard retreat.This remarkable residence offers almost 3400 square feet

    Mary Colton FANNIE HILLMAN & ASSOCIATES

    624 Tuscarora Trail, Maitland, FL 32751
  • /2

    $510,000

    Sold Aug 07, 2026

    1065 Gregory Dr, Maitland, FL 32751

    • 3 Beds
    • 2 Baths
    • 1,929 Sq Ft
    • Built 1958

    Last Sold Summary

    • 2% Below List Price
    • $264/SF
    • 43 Days On Market

    Current Estimated Value $512,616

    Last Listing Agent Cece Wong EXP REALTY LLC

    1065 Gregory Dr, Maitland, FL 32751
    • /42

      Est $243,148

      Not Listed For Sale

      1140 S Orlando Ave Unit A14, Maitland, FL 32751

      • 2 Beds
      • 1 Bath
      • 816 Sq Ft
      • Built 1964
      1140 S Orlando Ave Unit A14, Maitland, FL 32751

      Last Sold Summary

      • 139 Days On Market

      Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

  • /5

    $4,999,000

    New Construction
    • 5 Beds
    • 8 Baths
    • 6,466 Sq Ft

    360 Lake Seminary Cir, Maitland, FL 32751

    Pre-Construction. To be built. An extraordinary opportunity to claim one of Lake Seminary’s desired shorelines awaits. Masterfully envisioned by Heathrow Custom Homes, this newly built lakefront estate introduces a fresh standard of modern luxury for Maitland and Winter Park. Poised on an expansive 0.69-acre parcel, the residence spans nearly 6,500 square feet of impeccably curated living space,

    Mel Bernstein PREMIER SOTHEBYS INT'L REALTY

    360 Lake Seminary Cir, Maitland, FL 32751
  • /2

    $769,000

    Sold Jun 26, 2026

    101 Mariner Way, Maitland, FL 32751

    • 4 Beds
    • 2 Baths
    • 2,413 Sq Ft
    • Built 1972

    Last Sold Summary

    • $319/SF
    • 7 Days On Market

    Current Estimated Value $770,421

    Last Listing Agent MaryAnne Branner PREMIER SOTHEBY'S INTL. REALTY

    101 Mariner Way, Maitland, FL 32751
    • /2

      Est $423,582

      Not Listed For Sale

      1100 S Orlando Ave Unit 206, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 1,125 Sq Ft
      • Built 1973
      1100 S Orlando Ave Unit 206, Maitland, FL 32751

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent David Francetic COLDWELL BANKER REALTY

  • /37

    $1,695,000

    $200K PRICE DROP Under Contract
    • 4 Beds
    • 5 Baths
    • 4,478 Sq Ft

    1244 E Lake Colony Dr, Maitland, FL 32751

    Under contract-accepting backup offers. Priced for quick sale! 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

    Jennifer Sloan COMPASS FLORIDA LLC

    1244 E Lake Colony Dr, Maitland, FL 32751
  • /2

    $600,000

    Sold Mar 03, 2026

    2081 Mohican Trail, Maitland, FL 32751

    • 3 Beds
    • 2 Baths
    • 1,827 Sq Ft
    • Built 1962

    Last Sold Summary

    • $328/SF

    Current Estimated Value $595,563

    Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

    2081 Mohican Trail, Maitland, FL 32751
    • /2

      Est $324,118

      Not Listed For Sale

      210 Magnolia Rd Unit 110, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 1,000 Sq Ft
      • Built 1971
      210 Magnolia Rd Unit 110, Maitland, FL 32751

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Moe Mossa SAVVY AVENUE, LLC

  • /18

    $184,900

    • 2 Beds
    • 2 Baths
    • 1,206 Sq Ft

    2305 Haywood Ct Unit 203, Maitland, FL 32751

    **Welcome to Carrington Park, a beautifully maintained community in the heart of Maitland!** This spacious **2-bedroom, 2-bathroom condo** offers **over 1,200 square feet** of comfortable living space and has been lovingly cared for as a seasonal winter home, reflecting its exceptional condition throughout. Step inside to discover a bright and inviting floor plan featuring **vaulted ceilings**,

    Sina Albekord CORCORAN PREMIER REALTY

    2305 Haywood Ct Unit 203, Maitland, FL 32751
  • /2

    $448,500

    Sold Jul 20, 2026

    204 Quayside Cir Unit 504, Maitland, FL 32751

    • 2 Beds
    • 2 Baths
    • 1,270 Sq Ft
    • Built 1984

    Last Sold Summary

    • 13% Below List Price
    • $353/SF
    • 123 Days On Market

    Current Estimated Value $457,687

    Last Listing Agent Allison Hunter LUXE HUNTER REAL ESTATE

    204 Quayside Cir Unit 504, Maitland, FL 32751
    • /2

      Est $310,755

      Not Listed For Sale

      1000 Winderley Place Unit 240, Maitland, FL 32751

      • 3 Beds
      • 2 Baths
      • 1,538 Sq Ft
      • Built 1982
      1000 Winderley Place Unit 240, Maitland, FL 32751

  • /20

    $175,000

    • 2 Beds
    • 2 Baths
    • 1,048 Sq Ft

    1150 Lake Shadow Cir Unit 3305, Maitland, FL 32751

    Welcome to 1150 Lake Shadow Circle, Unit 3305, a 2-bedroom, 2-bath condominium located in the gated Visconti community in Maitland. Situated on the third floor, this 1,048-square-foot residence offers a functional floor plan with comfortable living spaces, luxury vinyl flooring, crown molding, ceiling fans, and the convenience of an in-unit washer and dryer.Step outside onto your private

    Jai Phillips EXP REALTY SOUTH LLC

    1150 Lake Shadow Cir Unit 3305, Maitland, FL 32751
  • /2

    $765,000

    Sold Sep 30, 2025

    808 Ponca Trail, Maitland, FL 32751

    • 4 Beds
    • 3 Baths
    • 2,311 Sq Ft
    • Built 1962

    Last Sold Summary

    • $331/SF
    • 4 Days On Market

    Current Estimated Value $776,433

    Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

    808 Ponca Trail, Maitland, FL 32751
    • /2

      Est $203,865

      Not Listed For Sale

      1100 Lake Shadow Cir Unit 2305, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 1,048 Sq Ft
      • Built 2000
      1100 Lake Shadow Cir Unit 2305, Maitland, FL 32751

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Lisa Hoad HOAD REALTY GROUP LLC

  • /31

    $484,000

    $16K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,683 Sq Ft

    370 Sultana Ln, Maitland, FL 32751

    Under contract-accepting backup offers. Welcome to 370 Sultana Lane, a beautifully reimagined residence nestled within the highly sought after Druid Hills community of Maitland. Thoughtfully renovated from top to bottom with more than $60,000 in improvements, this move-in ready home delivers the perfect combination of modern design, energy efficiency, and long-term value. PAID OFF SOLAR PANELS

    Abby Greenberg COMPASS FLORIDA LLC

    370 Sultana Ln, Maitland, FL 32751
  • /2

    $390,000

    Sold Nov 04, 2025

    1277 Blessing St, Maitland, FL 32751

    • 3 Beds
    • 2.5 Baths
    • 1,751 Sq Ft
    • Built 2006

    Last Sold Summary

    • 4% Below List Price
    • $223/SF
    • 119 Days On Market

    Current Estimated Value $389,609

    Last Listing Agent Denise LeHeup KELLER WILLIAMS WINTER PARK

    1277 Blessing St, Maitland, FL 32751
    • /29

      Est $217,538

      Not Listed For Sale

      1408 Lake Shadow Cir Unit 1301, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 1,111 Sq Ft
      • Built 2000
      1408 Lake Shadow Cir Unit 1301, Maitland, FL 32751

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Mark Ramey EXP REALTY LLC

  • /27

    $340,000

    $20K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 816 Sq Ft

    1140 S Orlando Ave Unit B7, Maitland, FL 32751

    Experience the perfect blend of Mid-Century Modern charm and contemporary living in this beautifully renovated 2-bedroom, 1-bath condominium in the highly sought-after Lake Maitland Terrace community. Nestled on the shores of Lake Maitland with access to the renowned Winter Park Chain of Lakes, this waterfront community offers an exceptional lifestyle in one of Central Florida's most desirable

    Tim Boon CREEGAN GROUP

    1140 S Orlando Ave Unit B7, Maitland, FL 32751
  • /2

    $640,000

    Sold Jul 16, 2026

    245 Orange Place, Maitland, FL 32751

    • 4 Beds
    • 3 Baths
    • 1,935 Sq Ft
    • Built 1946

    Last Sold Summary

    • 5% Below List Price
    • $331/SF
    • 3 Days On Market

    Current Estimated Value $661,959

    Last Listing Agent Jessica Lee ONE LUXURY INTERNATIONAL LLC

    245 Orange Place, Maitland, FL 32751
    • /5

      Est $236,758

      Not Listed For Sale

      1175 Lake Shadow Cir Unit 4103, Maitland, FL 32751

      • 3 Beds
      • 2 Baths
      • 1,243 Sq Ft
      • Built 2000
      1175 Lake Shadow Cir Unit 4103, Maitland, FL 32751

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Jim Bals VIDA REAL ESTATE SERVICES LLC

  • /48

    $190,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,111 Sq Ft

    1100 Lake Shadow Cir Unit 2307, Maitland, FL 32751

    Virtually Staged. Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo in the sought-after Visconti community, where comfort, convenience, and lifestyle come together. Located on the third floor, this light-filled residence features soaring vaulted ceilings that create an open, airy feel, complemented by abundant natural light throughout. Ideally positioned just steps from the

    Jodi Lambiase KELLER WILLIAMS REALTY AT THE LAKES

    1100 Lake Shadow Cir Unit 2307, Maitland, FL 32751
  • /2

    $1,655,000

    Sold Oct 31, 2025

    104 E Lake Colony Dr, Maitland, FL 32751

    • 5 Beds
    • 4.5 Baths
    • 5,209 Sq Ft
    • Built 1998

    Last Sold Summary

    • 5% Below List Price
    • $318/SF
    • 18 Days On Market

    Current Estimated Value $1,672,577

    Last Listing Agent David Plasencia COLDWELL BANKER REALTY

    104 E Lake Colony Dr, Maitland, FL 32751
    • /27

      Est $162,637

      Not Listed For Sale

      1275 Lake Shadow Cir Unit 13112, Maitland, FL 32751

      • 1 Bed
      • 1 Bath
      • 746 Sq Ft
      • Built 2000
      1275 Lake Shadow Cir Unit 13112, Maitland, FL 32751

      Last Sold Summary

      • 85 Days On Market

      Last Listing Agent Tess Muccigrosso RE/MAX 200 REALTY

  • /45

    $1,125,000

    $25K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,857 Sq Ft

    900 Brightwater Cir, Maitland, FL 32751

    "Price Improvement"-Move-In Ready. 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

    David Alderman ELITE EVOLUTION PROPERTIES

    900 Brightwater Cir, Maitland, FL 32751
  • /2

    $232,000

    Sold Apr 22, 2026

    351 W Lake Faith Dr Unit 117, Maitland, FL 32751

    • 2 Beds
    • 2 Baths
    • 1,403 Sq Ft
    • Built 1974

    Last Sold Summary

    • $165/SF

    Current Estimated Value $233,738

    Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

    351 W Lake Faith Dr Unit 117, Maitland, FL 32751
    • /2

      Est $264,967

      Not Listed For Sale

      1000 Winderley Place Unit 122, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 1,164 Sq Ft
      • Built 1982
      1000 Winderley Place Unit 122, Maitland, FL 32751

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

  • /63

    $895,000

    $70K PRICE DROP Under Contract
    • 4 Beds
    • 3.5 Baths
    • 2,407 Sq Ft

    2112 Chippewa Trail, Maitland, FL 32751

    Under contract-accepting backup offers. 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

    Laura Heidrich COLDWELL BANKER REALTY

    2112 Chippewa Trail, Maitland, FL 32751
  • /2

    $1,100,000

    Sold Oct 27, 2025

    941 Versailles Cir, Maitland, FL 32751

    • 4 Beds
    • 3 Baths
    • 2,717 Sq Ft
    • Built 1981

    Last Sold Summary

    • 4% Below List Price
    • $405/SF
    • 66 Days On Market

    Current Estimated Value $1,088,056

    Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

    941 Versailles Cir, Maitland, FL 32751
    • /2

      Est $185,194

      Not Listed For Sale

      640 Robinhood Dr Unit B, Maitland, FL 32751

      • 2 Beds
      • 1 Bath
      • 765 Sq Ft
      • Built 1968
      640 Robinhood Dr Unit B, Maitland, FL 32751

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Chris Winn BLOOM HOME GROUP REALTY LLC

  • /15

    $394,000

    Pending
    • 4 Beds
    • 2 Baths
    • 2,064 Sq Ft

    2467 Fieldingwood Rd, Maitland, FL 32751

    Opportunity awaits in the established English Woods community! This 3-bedroom, 2-bath pool home is full of potential and ready for its next owner to bring it back to life. Originally designed as a 4-bedroom, the home can easily be converted back, offering added flexibility and living space. Featuring a spacious floor plan, private pool, and hot tub, this property is an excellent opportunity for

    Chris Creegan CREEGAN GROUP

    2467 Fieldingwood Rd, Maitland, FL 32751
  • /2

    $230,000

    Sold Feb 26, 2026

    551 Finchley Rd Unit 551, Maitland, FL 32751

    • 2 Beds
    • 2 Baths
    • 1,293 Sq Ft
    • Built 1982

    Last Sold Summary

    • $178/SF
    • 44 Days On Market

    Last Listing Agent Lana Larrivee PREFERRED RE BROKERS III

    551 Finchley Rd Unit 551, Maitland, FL 32751
    • /2

      Est $192,368

      Not Listed For Sale

      1375 Lake Shadow Cir Unit 11107, Maitland, FL 32751

      • 2 Beds
      • 1 Bath
      • 898 Sq Ft
      • Built 2000
      1375 Lake Shadow Cir Unit 11107, Maitland, FL 32751

      Last Sold Summary

      • 59 Days On Market

      Last Listing Agent Matt Merdian MERDIAN REALTY LLC

  • /29

    $150,000

    • 2 Beds
    • 2 Baths
    • 1,206 Sq Ft

    2313 Haywood Ct Unit 201, Maitland, FL 32751

    Welcome to Carrington Park Condominiums! This 2-BEDROOM, 2-BATHROOM condo is located on the TOP FLOOR, (only1 flight of stairs) offering added privacy with no neighbors above. The comfortable floor plan provides plenty of space for everyday living, while the SCREENED-IN BALCONY is the perfect spot to relax and enjoy the Florida weather. A STACKABLE WASHER-DRYER is conveniently located inside the

    Jennifer Wemert WEMERT GROUP REALTY LLC

    2313 Haywood Ct Unit 201, Maitland, FL 32751
  • /2

    $1,495,000

    Sold Jun 24, 2026

    221 Minnehaha Rd, Maitland, FL 32751

    • 4 Beds
    • 3 Baths
    • 3,797 Sq Ft
    • Built 1957

    Last Sold Summary

    • $394/SF
    • 5 Days On Market

    Current Estimated Value $1,471,519

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    221 Minnehaha Rd, Maitland, FL 32751
    • /2

      Est $163,779

      Not Listed For Sale

      1125 Lake Shadow Cir Unit 5109, Maitland, FL 32751

      • 1 Bed
      • 1 Bath
      • 672 Sq Ft
      • Built 2000
      1125 Lake Shadow Cir Unit 5109, Maitland, FL 32751

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Leah Marshall UNITED REAL ESTATE PREFERRED

  • /34

    $525,000

    $35K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,801 Sq Ft

    726 Forest Glen Ct, Maitland, FL 32751

    Welcome to this beautifully redesigned move-in-ready pool home, tucked away on a quiet cul-de-sac NO HOA in desirable Maitland. Step inside to a bright, open-concept layout featuring a stunning new kitchen with quartz countertops, shaker cabinetry, stainless-steel appliances, and a waterfall island perfect for entertaining. Luxury flooring, beautifully remodeled bathrooms, and modern finishes

    Janet Garay FLORIDA REALTY OF MIAMI CORP

    726 Forest Glen Ct, Maitland, FL 32751
  • /2

    $755,000

    Sold Jun 05, 2026

    312 Macarthur Place, Maitland, FL 32751

    • 3 Beds
    • 2.5 Baths
    • 2,441 Sq Ft
    • Built 1981

    Last Sold Summary

    • 8% Below List Price
    • $309/SF
    • 65 Days On Market

    Current Estimated Value $757,891

    Last Listing Agent Sean David REAL BROKER, LLC

    312 Macarthur Place, Maitland, FL 32751
    • /59

      Est $214,128

      Not Listed For Sale

      1420 Lake Shadow Cir Unit 9208, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 1,111 Sq Ft
      • Built 2000
      1420 Lake Shadow Cir Unit 9208, Maitland, FL 32751

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Susan Schneider COLDWELL BANKER REALTY

  • /43

    $825,000

    Open Sun 1PM - 3PM
    • 3 Beds
    • 2.5 Baths
    • 2,801 Sq Ft

    505 Oak Ln, Maitland, FL 32751

    **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to this gorgeous, move-in-ready 3-bedroom, 2.5-bath POOL home in the desirable Oakland Shores neighborhood of Maitland! Situated on an oversized, beautifully landscaped lot, this exceptional home welcomes you with

    Erich Adams DALTON WADE INC

    505 Oak Ln, Maitland, FL 32751

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