9,826

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
  • /31

    Starting at $1,855 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

    $230,000

    Sold Feb 27, 2026

    1460 Lake Shadow Cir Unit 7107, Maitland, FL 32751

    • 4 Beds
    • 2 Baths
    • 1,372 Sq Ft
    • Built 2000

    Last Sold Summary

    • 8% Below List Price
    • $168/SF
    • 148 Days On Market

    Current Estimated Value $237,029

    Last Listing Agent Alie Gattis MAINFRAME REAL ESTATE

    1460 Lake Shadow Cir Unit 7107, Maitland, FL 32751
    • /2

      Est $695,081

      Not Listed For Sale

      1850 Geronimo Trail, Maitland, FL 32751

      • 3 Beds
      • 2 Baths
      • 1,736 Sq Ft
      • Built 1959
      1850 Geronimo Trail, Maitland, FL 32751

      Last Sold Summary

      • 42 Days On Market

      Last Listing Agent Bobby Livera BALDWIN PARK REALTY LLC

  • /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 $1,475

    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
  • /81

    $520,000

    Sold Sep 09, 2026

    1511 Glastonberry Rd, Maitland, FL 32751

    • 5 Beds
    • 3 Baths
    • 2,376 Sq Ft
    • Built 1969

    Last Sold Summary

    • 8% Below List Price
    • $219/SF
    • 27 Days On Market

    Current Estimated Value $548,555

    Last Listing Agent Maydelin Munoz FLORIDA REALTY INVESTMENTS

    1511 Glastonberry Rd, Maitland, FL 32751
    • /16

      Est $154,817

      Not Listed For Sale

      1400 Lake Shadow Cir Unit 10304, Maitland, FL 32751

      • 1 Bed
      • 1 Bath
      • 672 Sq Ft
      • Built 2000
      1400 Lake Shadow Cir Unit 10304, Maitland, FL 32751

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Isabel Sirizzotti SUNNY 365 REALTY GROUP

  • /7

    $440,000

    New Construction Coming Soon
    • 4 Beds
    • 2 Baths
    • 1,809 Sq Ft

    27 N Calhoun Ave, Maitland, FL 32751

    BRAND-NEW CONSTRUCTION IN MAITLAND, FL! Welcome to this beautifully designed 4-bedroom, 2-bath home offering 1,809 sq. ft. under air and 2,359 total sq. ft., with NO HOA and an oversized driveway providing plenty of parking.Step inside to a bright, open-concept floor plan where the family and dining areas flow seamlessly into a spacious modern kitchen designed for both everyday living and

    Nohora Gomez COLDWELL BANKER REALTY

    27 N Calhoun Ave, Maitland, FL 32751
  • /37

    Starting at $2,479 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

    $338,000

    Sold Oct 27, 2025

    500 Vereen Dr, Maitland, FL 32751

    • 4 Beds
    • 2 Baths
    • 1,605 Sq Ft
    • Built 1966

    Last Sold Summary

    • 6% Below List Price
    • $211/SF
    • 83 Days On Market

    Current Estimated Value $342,424

    Last Listing Agent Husain Jaffer CHARLES RUTENBERG REALTY ORLANDO

    500 Vereen Dr, Maitland, FL 32751
    • /25

      Est $670,427

      Not Listed For Sale

      2222 Chippewa Trail, Maitland, FL 32751

      • 3 Beds
      • 2 Baths
      • 1,960 Sq Ft
      • Built 1961
      2222 Chippewa Trail, Maitland, FL 32751

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Shirley Jones COLDWELL BANKER REALTY

  • /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
  • /39

    Starting at $1,769 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

    $835,000

    Sold Aug 21, 2026

    1633 Choctaw Trail, Maitland, FL 32751

    • 4 Beds
    • 2 Baths
    • 2,061 Sq Ft
    • Built 1957

    Last Sold Summary

    • 1% Above List Price
    • $405/SF
    • 3 Days On Market

    Current Estimated Value $796,860

    Last Listing Agent Ingrid Livingston COLDWELL BANKER REALTY

    1633 Choctaw Trail, Maitland, FL 32751
    • /30

      Est $390,601

      Not Listed For Sale

      2027 Michael Tiago Cir, Maitland, FL 32751

      • 3 Beds
      • 2.5 Baths
      • 2,193 Sq Ft
      • Built 2014
      2027 Michael Tiago Cir, Maitland, FL 32751

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Doug Woehr COLDWELL BANKER REALTY

  • /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 $1,882

    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

    $475,000

    Sold Dec 29, 2025

    1938 Michael Tiago Cir, Maitland, FL 32751

    • 4 Beds
    • 2.5 Baths
    • 2,708 Sq Ft
    • Built 2011

    Last Sold Summary

    • 4% Below List Price
    • $175/SF
    • 74 Days On Market

    Current Estimated Value $488,862

    Last Listing Agent Robin Mitchell ROBIN MITCHELL REALTY

    1938 Michael Tiago Cir, Maitland, FL 32751
    • /46

      Est $405,503

      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

      Last Listing Agent Heather Ward WATSON REALTY CORP

  • /2

    $215,000

    • 3 Beds
    • 2 Baths
    • 1,612 Sq Ft

    2308 Haywood Ct Unit 100, Maitland, FL 32751

    Need Room! Welcome home to this spacious 1612 S.F. first-floor condominium featuring three bedrooms and two full baths in a well-maintained community conveniently located near shopping, dining, and Full Sail University. Step inside to find brand-new luxury plank flooring throughout the living and bedroom areas, ceramic tile in the kitchen and bathrooms, and absolutely no carpet! Blinds on all

    Frank Kusiak MY FLORIDA HOME CENTER REAL ESTATE

    2308 Haywood Ct Unit 100, Maitland, FL 32751
  • /38

    Starting at $1,832

    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

    $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 $461,953

    Last Listing Agent Dan Samatulski MAINFRAME REAL ESTATE

    741 Robinhood Dr, Maitland, FL 32751
    • /22

      Est $156,520

      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

      Last Listing Agent Lisa Sabo ALFANO PROPERTY MANAGEMENT

  • /71

    $2,999,000

    $101K PRICE DROP
    • 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
  • /30

    $1,289 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

    $424,000

    Sold Jun 30, 2026

    775 Woodside Rd, Maitland, FL 32751

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1973

    Last Sold Summary

    • 6% Below List Price
    • $291/SF
    • 9 Days On Market

    Current Estimated Value $449,552

    Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

    775 Woodside Rd, Maitland, FL 32751
    • /2

      Est $482,022

      Not Listed For Sale

      510 W Faith Terrace, Maitland, FL 32751

      • 3 Beds
      • 2 Baths
      • 1,672 Sq Ft
      • Built 1960
      510 W Faith Terrace, Maitland, FL 32751

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  • /67

    $979,000

    $16K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 4,055 Sq Ft

    229 Flame Ave, Maitland, FL 32751

    LOWER YOUR RATE FOR THE FIRST 2 YEARS! SPECIAL FINANCING INCENTIVE! Seller will contribute toward a temporary mortgage rate buydown for a qualified buyer, potentially providing reduced monthly mortgage payments during the first two years. Contact listing agent for additional details. Welcome to Hidden Estates, where luxury, space, and flexibility come together in one of Maitland's most

    Heather Meglino BHHS FLORIDA REALTY

    229 Flame Ave, Maitland, FL 32751
  • /35

    $1,589 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

    $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 $276,225

    Last Listing Agent Melissa Johnson EXP REALTY LLC

    920 Park Lake Cir Unit 36, Maitland, FL 32751
    • /11

      Est $432,171

      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

      Last Listing Agent Joann Beck BECK REALTY LLC

  • /2

    $218,400

    • 2 Beds
    • 2 Baths
    • 1,111 Sq Ft

    1225 Lake Shadow Cir Unit 14102, Maitland, FL 32751

    Auction Property. Auction Property. AUCTION/OCCUPIED. Buyers will be required to sign a occupancy declaration. 2-bedroom 2-bathroom condominium in gated community of Visconti West situated off Lake Shadow. Quick access to interstate 4 and Florida turnpike. Property is sold “as is” with NO property disclosures, NO inspection reports, NO interior photos, NO lease in place, NO access- The seller

    Jamarr Zellner REALHOME SERVICE & SOLUTIONS INC

    1225 Lake Shadow Cir Unit 14102, Maitland, FL 32751
  • /22

    $2,500

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    2923 Shadow View Cir Unit 2923 Shadow View Cir, Maitland, FL 32751

    12 Month Lease, $2,500 deposit, available NOW! Rent includes water and trash pick up, just set up electricity and internet!Work, live, and play in the elegant Visconti gated community a desirable townhouse in Maitland City, Florida. This elegant Updated and upgraded 2 bedrooms and 2 bathrooms townhouse with a 2 car garage + 2 extra parking spaces. This property has a stunning new

    2923 Shadow View Cir Unit 2923 Shadow View Cir, Maitland, FL 32751
  • /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 $234,896

    Last Listing Agent Tom Graves FUN HOMES

    1550 Gulfview Dr Unit 444B, Maitland, FL 32751
    • /21

      Est $307,367

      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

      Last Listing Agent Raul Veitia BELMONT REALTY

  • /38

    $950,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 2,145 Sq Ft

    823 Woods Ct, Maitland, FL 32751

    Under contract-accepting backup offers. Outstanding Dommerich Woods location on .28 acre lot with serene views of the nature preserve! This immaculate home offers the perfect blend of comfort, style and privacy. Tucked away on a charming tree-lined cul-de-sac, 823 Woods Court welcomes you with exceptional curb appeal. Step inside to a spacious foyer introducing gleaming wood floors, elegant crown

    Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

    823 Woods Ct, Maitland, FL 32751
  • /35

    $1,409 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 $808,951

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    2270 Deloraine Trail, Maitland, FL 32751
    • /15

      Est $101,942

      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

      Last Listing Agent Sangita Khatri BRIC REALTY LLC

Showing Results 41 - 80, Page 2 of 18

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