9,991

Maitland, FL Homes

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  • /37

    $325,000

    • 2 Beds
    • 1.5 Baths
    • 816 Sq Ft

    1140 S Orlando Ave Unit I14, Maitland, FL 32751

    One or more photo(s) has been virtually staged. Where Maitland's pristine waters meet a modern lifestyle! This luxury condominium in the coveted Lake Maitland Terrace community offers a rare blend of elegance and convenience on the shores of Lake Maitland within the famed Winter Park Chain of Lakes. Nestled among lush green spaces, this impeccably maintained mid-century modern complex boasts easy

    Michele Ostrander CHARLES RUTENBERG REALTY ORLANDO

    1140 S Orlando Ave Unit I14, Maitland, FL 32751
  • /55

    Starting at $1,780 Per Month

    • 1 - 3 Beds

    955 N Orlando Ave, Maitland, FL 32751

    Connect to what matters at The Parker at Maitland Station, Orlando's newest luxury apartment community. Located at the historic Parker Lumber Yard site, our Maitland, FL apartments provide easy access to the very best dining,shopping, jobs and outdoor activities Central Florida has to offer. The Parker at Maitland Station Apartments focuses on the old school friendliness while setting new

    The Parker at Maitland Station Apartments

    955 N Orlando Ave, Maitland, FL 32751
  • /2

    $6,650,000

    Sold Jun 27, 2025

    119 Whitecaps Cir, Maitland, FL 32751

    • 4 Beds
    • 5.5 Baths
    • 6,800 Sq Ft
    • Built 2004

    Last Sold Summary

    • $978/SF

    Current Estimated Value $6,381,318

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

    119 Whitecaps Cir, Maitland, FL 32751
    • /46

      Est $446,463

      Not Listed For Sale

      2030 Michael Tiago Cir, Maitland, FL 32751

      • 3 Beds
      • 2.5 Baths
      • 2,249 Sq Ft
      • Built 2014
      2030 Michael Tiago Cir, Maitland, FL 32751

      Last Sold Summary

      • 4 Days On Market

  • /52

    $899,000

    $60K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,485 Sq Ft

    614 Brookwood Ln, Maitland, FL 32751

    JUST REDUCED - Welcome to this meticulously updated, one-story masterpiece situated on a sprawling, professionally landscaped 1/3-acre lot. This 5-bedroom, 3.5-bath sanctuary plus bonus room seamlessly blends high-end design with modern efficiency. At the heart of the home lies an extra-large gourmet kitchen designed for the serious chef, featuring double ovens, dual microwaves, and two

    Gale Milgrim KELLER WILLIAMS WINTER PARK

    614 Brookwood Ln, Maitland, FL 32751
  • /31

    Starting at $1,927 Per Month

    • 1 - 2 Beds

    160-190 Independence Ln, Maitland, FL 32751

    .custom-read-more #more {display: none;} Indulge in the upscale lifestyle you deserve—our spacioushomes in the heart of Maitland have everything you need to make it happen.High-end amenities, elegant interiors, and an excellent location in the NorthOrlando area blend together to create a carefree experience. So check out our luxury apartments in Maitland, FL and find the home

    Maitland City Centre

    160-190 Independence Ln, Maitland, FL 32751
  • /2

    $455,000

    Sold Nov 10, 2025

    741 Robinhood Dr, Maitland, FL 32751

    • 3 Beds
    • 2 Baths
    • 1,239 Sq Ft
    • Built 1985

    Last Sold Summary

    • 1% Above List Price
    • $367/SF
    • 18 Days On Market

    Current Estimated Value $443,745

    Last Listing Agent Dan Samatulski MAINFRAME REAL ESTATE

    741 Robinhood Dr, Maitland, FL 32751
    • /22

      Est $151,482

      Not Listed For Sale

      2333 Coawood Ct Unit 103, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 1,206 Sq Ft
      • Built 1973
      2333 Coawood Ct Unit 103, Maitland, FL 32751

      Last Sold Summary

      • 10 Days On Market

  • /62

    $575,000

    $22K PRICE DROP Pending
    • 4 Beds
    • 3.5 Baths
    • 2,551 Sq Ft

    572 Green Meadow Ct, Maitland, FL 32751

    Nestled within the established community of Forest Brook, on a quiet cul-de-sac, you will find an immaculately kept pool home that is ready for a new owner to enjoy! This mid-century design boasts gorgeous, vaulted hardwood ceilings, charm & character throughout, as well as natural light. As you enter the home you are immediately greeted by an atrium/music room with multiple glass walls &

    Stacie Brown Kelly KELLER WILLIAMS ADVANTAGE REALTY

    572 Green Meadow Ct, Maitland, FL 32751
  • /25

    Starting at $1,460

    Total Monthly Price

    • 1 - 3 Beds

    545 S Keller Rd, Orlando, FL 32810

    Stylishly modern. Great location. A perfect home for you. The Courtney at Lake Shadow, a luxury apartment community in Orlando, Florida, offers open-concept layouts in a variety of pet-friendly 1, 2 & 3 bedroom floor plans. Enjoy your gourmet kitchen – stir up more than coffee. It’s fully equipped and ready for you to make fantastic meals for friends or craft home-cooked meals solo. Plus, each

    Courtney At Lake Shadow

    545 S Keller Rd, Orlando, FL 32810
  • /2

    $550,000

    Sold Jul 01, 2025

    2040 Mohawk Trail, Maitland, FL 32751

    • 3 Beds
    • 2 Baths
    • 1,754 Sq Ft
    • Built 1961

    Last Sold Summary

    • 6% Below List Price
    • $314/SF
    • 17 Days On Market

    Current Estimated Value $567,360

    Last Listing Agent Nicole Seybold FANNIE HILLMAN & ASSOCIATES

    2040 Mohawk Trail, Maitland, FL 32751
    • /11

      Est $420,423

      Not Listed For Sale

      1100 S Orlando Ave Unit 704, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 1,285 Sq Ft
      • Built 1973
      1100 S Orlando Ave Unit 704, Maitland, FL 32751

      Last Sold Summary

      • 49 Days On Market

  • /49

    $469,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,856 Sq Ft

    2319 Falmouth Rd, Maitland, FL 32751

    Under contract-accepting backup offers. Welcome to this wonderful 3 bedroom, 2 bathroom mid-century home with amazing curbside appeal in the desirable English Estates neighborhood. This home is located on a generous corner lot with a brick paver walkway flanked by beautifully manicured landscape and an impressively large camphor tree. The light blue front door adds a touch of charm and elegance

    Lisa Gould KELLER WILLIAMS WINTER PARK

    2319 Falmouth Rd, Maitland, FL 32751
  • /37

    Starting at $2,422 Per Month

    • 1 - 3 Beds

    100 Boucle Jeanne Cir, Maitland, FL 32751

    Drink in the waterfront views. Drop your kayak in for an evening cruise. Dip your toes in the saltwater pool. When you’re here, every day feels like a waterside retreat. Only it’s not a vacation, it’s your home. With nature-inspired interior design, multiple outdoor living spaces and direct lake access, Perla Gem Lake is luxury lakeside living.

    Perla Gem Lake

    100 Boucle Jeanne Cir, Maitland, FL 32751
  • /2

    $515,000

    Sold Sep 10, 2025

    204 Quayside Cir Unit 601, Maitland, FL 32751

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

    Last Sold Summary

    • 3% Below List Price
    • $406/SF
    • 45 Days On Market

    Current Estimated Value $523,972

    Last Listing Agent Travis Cepregi KELLER WILLIAMS WINTER PARK

    204 Quayside Cir Unit 601, Maitland, FL 32751
    • /21

      Est $309,629

      Not Listed For Sale

      1000 Winderley Place Unit 126, Maitland, FL 32751

      • 3 Beds
      • 2 Baths
      • 1,538 Sq Ft
      • Built 1982
      1000 Winderley Place Unit 126, Maitland, FL 32751

      Last Sold Summary

      • 73 Days On Market

  • /33

    $409,900

    $20K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,512 Sq Ft

    2150 Tortoise Shell Dr, Maitland, FL 32751

    Virtually Staged. FRESHLY UPDATED CABINETRY, FOURTH BEDROOM OPTION ADDED! 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

    Claire Sims LLC LPT REALTY, LLC

    2150 Tortoise Shell Dr, Maitland, FL 32751
  • /39

    Starting at $1,826 Per Month

    • 1 - 3 Beds

    2200 Flagler Promenade Way, Maitland, FL 32751

    There's a special appeal to living lakeside. An almost magical draw that brings clarity and calmness to the forefront. Where resolutions are revealed... Troubles washed away. The lake remains familiar, reliable, trustworthy. Always there, welcoming you home. Come find the serene lifestyle you've been dreaming of here at Luna at Lake Shadow. Featuring spacious one, two and three bedroom apartments

    Luna at Lake Shadow

    2200 Flagler Promenade Way, Maitland, FL 32751
  • /2

    $279,000

    Sold Mar 06, 2026

    920 Park Lake Cir Unit 36, Maitland, FL 32751

    • 3 Beds
    • 2.5 Baths
    • 1,486 Sq Ft
    • Built 1972

    Last Sold Summary

    • 4% Above List Price
    • $188/SF
    • 72 Days On Market

    Current Estimated Value $274,358

    Last Listing Agent Melissa Johnson EXP REALTY LLC

    920 Park Lake Cir Unit 36, Maitland, FL 32751
    • /15

      Est $104,125

      Not Listed For Sale

      551 Flemming Way Unit 101, Maitland, FL 32751

      • 1 Bed
      • 1 Bath
      • 550 Sq Ft
      • Built 1973
      551 Flemming Way Unit 101, Maitland, FL 32751

      Last Sold Summary

      • 1 Day On Market

  • /12

    $265,000

    $35K PRICE DROP
    • Land
    • 11,761 Sq Ft
    • $981,481 per Acre

    0 Mechanic St, Maitland, FL 32751

    Unlock the Potential of Your Dream Property in Maitland, Florida!Discover a prime opportunity to build your vision in the heart of Maitland, a charming and thriving community just minutes from downtown Orlando. This vacant land offers a blank canvas for your dream home or investment property. Nestled in a highly desirable area, you'll enjoy easy access to top-rated schools, tranquil parks,

    Cheree Graham KELLER WILLIAMS REALTY AT THE PARKS

    0 Mechanic St, Maitland, FL 32751
  • /47

    Starting at $1,671

    Total Monthly Price

    • 1 - 3 Beds

    400 N Orlando Ave, Maitland, FL 32751

    At 400 North, thoughtful home design meets effortless living in one of Maitland?s most connected neighborhoods. From the resort-style pool and fire pit lounge to the tranquil Zen courtyard, every outdoor space invites you to slow down and recharge. Inside, curated apartment features such as eat-in kitchen countertop seating and tiled baths meet spectacular lakeside views. With on-site retail and

    400 North

    400 N Orlando Ave, Maitland, FL 32751
  • /2

    $970,000

    Sold Jul 31, 2025

    91 Minnehaha Cir, Maitland, FL 32751

    • 4 Beds
    • 2 Baths
    • 2,826 Sq Ft
    • Built 1971

    Last Sold Summary

    • 1% Below List Price
    • $343/SF
    • 6 Days On Market

    Current Estimated Value $950,650

    Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    91 Minnehaha Cir, Maitland, FL 32751
    • /2

      Est $485,981

      Not Listed For Sale

      1998 Michael Tiago Cir, Maitland, FL 32751

      • 4 Beds
      • 2.5 Baths
      • 2,691 Sq Ft
      • Built 2013
      1998 Michael Tiago Cir, Maitland, FL 32751

      Last Sold Summary

      • 2 Days On Market

  • /53

    $534,900

    $50K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,641 Sq Ft

    1230 Hollyridge Trail, Maitland, FL 32751

    Dommerich Woods gem! Tucked away on a cul-de-sac street in one of Maitland’s most sought-after neighborhoods, this beautifully updated 3-bedroom, 2-bath block home is the one you’ve been waiting for. Move-in ready and genuinely charming from the moment you walk in. The open floor plan feels airy and welcoming, with vaulted ceilings and natural light pouring through every room. The living room

    Stephanie Doucette BOWERBIRD REALTY

    1230 Hollyridge Trail, Maitland, FL 32751
  • /38

    Starting at $1,754

    Total Monthly Price

    • 1 - 3 Beds

    9000 Summit Centre Way, Orlando, FL 32810

    Dawson Apartments delivers elevated lakeside living in North Orlando, pairing upscale design with a location that keeps you connected to the best of Central Florida. Surrounded by water views and lush landscaping, this luxury community offers a refined retreat while placing shopping, dining, recreation and major roadways just minutes from home. Choose from spacious one-, two- and three-bedroom

    Dawson

    9000 Summit Centre Way, Orlando, FL 32810
  • /2

    $458,000

    Sold Dec 26, 2025

    2133 Falkner Rd, Maitland, FL 32751

    • 4 Beds
    • 3 Baths
    • 1,779 Sq Ft
    • Built 1998

    Last Sold Summary

    • 2% Above List Price
    • $257/SF
    • 5 Days On Market

    Current Estimated Value $451,912

    Last Listing Agent Jason Asa LPT REALTY, LLC

    2133 Falkner Rd, Maitland, FL 32751
    • /25

      Est $315,436

      Not Listed For Sale

      437 Poplar Ct, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 1,182 Sq Ft
      • Built 1983
      437 Poplar Ct, Maitland, FL 32751

      Last Sold Summary

      • 1 Day On Market

  • /71

    $3,100,000

    • 6 Beds
    • 4.5 Baths
    • 5,355 Sq Ft

    1166 N Lake Sybelia Dr, Maitland, FL 32751

    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,

    Joseph Sipp KELLER WILLIAMS WINTER PARK

    1166 N Lake Sybelia Dr, Maitland, FL 32751
  • /35

    $1,889 Per Month

    • Studio
    • 1 Bath
    • 300 Sq Ft
    • Condo for Rent

    1776 Pembrook Dr, Orlando, FL 32810

    Enjoy a fully furnished studio suite in our hotel at an affordable rate with free wi-fi, free utilities and free premium cable. Each studio suite has a full kitchen with full-size refrigerator, stovetop and microwave, and has a flexible workspace and plenty of storage. All our hotels are pet-friendly and have on-site guest laundry available. Plus, there are no long-term commitments and you can

    1776 Pembrook Dr, Orlando, FL 32810
  • /2

    $235,000

    Sold Mar 30, 2026

    1550 Gulfview Dr Unit 444B, Maitland, FL 32751

    • 3 Beds
    • 3 Baths
    • 1,328 Sq Ft
    • Built 1982

    Last Sold Summary

    • 2% Below List Price
    • $177/SF
    • 22 Days On Market

    Current Estimated Value $235,808

    Last Listing Agent Tom Graves FUN HOMES

    1550 Gulfview Dr Unit 444B, Maitland, FL 32751
    • /2

      Est $325,817

      Not Listed For Sale

      1902 Water Ln, Maitland, FL 32751

      • 3 Beds
      • 2.5 Baths
      • 1,483 Sq Ft
      • Built 1983
      1902 Water Ln, Maitland, FL 32751

      Last Sold Summary

      • 30 Days On Market

  • /81

    $549,000

    $16K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,376 Sq Ft

    1511 Glastonberry Rd, Maitland, FL 32751

    This AMAZING!, spacious 5-bedroom, 3-bath split-level home is located in a fantastic neighborhood and is packed with standout features. Upstairs, you’ll find beautiful engineered hardwood flooring throughout the main living areas, with carpet in the bedrooms and tile in the baths. A stunning screened-in porch overlooks the backyard and pool, offering a perfect spot to relax or entertain. The

    Maydelin Munoz FLORIDA REALTY INVESTMENTS

    1511 Glastonberry Rd, Maitland, FL 32751
  • /35

    $1,589 Per Month

    • Studio
    • 1 Bath
    • 300 Sq Ft
    • Furnished Studio-Orlando - Maitland - Summit Tower Blvd

    1951 Summit Tower Blvd, Orlando, FL 32810

    Enjoy a fully furnished studio suite in our hotel at an affordable rate with free wi-fi, free utilities and free premium cable. Each studio suite has a full kitchen with full-size refrigerator, stovetop and microwave, and has a flexible workspace and plenty of storage. All our hotels are pet-friendly and have on-site guest laundry available. Plus, there are no long-term commitments and you can

    Furnished Studio-Orlando - Maitland - Summit Tower Blvd

    1951 Summit Tower Blvd, Orlando, FL 32810
  • /2

    $820,000

    Sold Feb 18, 2026

    2270 Deloraine Trail, Maitland, FL 32751

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • Built 1964

    Last Sold Summary

    • 4% Below List Price
    • $410/SF
    • 15 Days On Market

    Current Estimated Value $812,195

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    2270 Deloraine Trail, Maitland, FL 32751
    • /28

      Est $315,855

      Not Listed For Sale

      1979 Water Ln, Maitland, FL 32751

      • 3 Beds
      • 2 Baths
      • 1,351 Sq Ft
      • Built 1983
      1979 Water Ln, Maitland, FL 32751

      Last Sold Summary

      • 0 Days On Market

  • /40

    $174,900

    • 2 Beds
    • 1 Bath
    • 898 Sq Ft

    1375 Lake Shadow Cir Unit 11203, Maitland, FL 32751

    Amazing upgraded two-bedroom, one bath Condo in the gated waterfront community at Visconti in Maitland with features of spacious living and comfortability. This stunning Condo Unit features with large windows letting in plenty of natural light and giving the common living area a fresh air feel. The dining/living combo opens to a big, screened patio through sliding glass doors. The kitchen

    Simon Colak USCO CAPITAL GROUP

    1375 Lake Shadow Cir Unit 11203, Maitland, FL 32751
  • /30

    $1,499 Per Month

    • Studio
    • 1 Bath
    • 300 Sq Ft
    • Condo for Rent

    1760 Pembrook Dr, Orlando, FL 32810

    Enjoy a fully furnished studio suite in our hotel at an affordable rate with free wi-fi, free utilities and free premium cable. Each studio suite has a full kitchen with full-size refrigerator, stovetop and microwave, and has a flexible workspace and plenty of storage. All our hotels are pet-friendly and have on-site guest laundry available. Plus, there are no long-term commitments and you can

    1760 Pembrook Dr, Orlando, FL 32810
  • /2

    $2,770,000

    Sold Sep 11, 2025

    216 N Lake Sybelia Dr, Maitland, FL 32751

    • 5 Beds
    • 5.5 Baths
    • 4,697 Sq Ft
    • Built 2021

    Last Sold Summary

    • 4% Below List Price
    • $590/SF
    • 3 Days On Market

    Current Estimated Value $2,693,733

    Last Listing Agent Kevin Acker RE/MAX 200 REALTY

    216 N Lake Sybelia Dr, Maitland, FL 32751
    • /33

      Est $292,222

      Not Listed For Sale

      436 Poplar Ct, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 1,182 Sq Ft
      • Built 1983
      436 Poplar Ct, Maitland, FL 32751

      Last Sold Summary

      • 6 Days On Market

Showing Results 41 - 80, Page 2 of 18

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