9,826

Maitland, FL Homes

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  • /2

    $499,900

    • 4 Beds
    • 2 Baths
    • 1,674 Sq Ft

    812 Woodside Rd, Maitland, FL 32751

    Updated 4-bedroom, 2-bath heated pool home situated on a .27-acre corner lot in the sought-after Forest Brook neighborhood. From the moment you arrive, you’ll notice the paver driveway, mature landscaping, pops of color, and warm wood accents that give the home great curb appeal.Step inside to an open floor plan with soaring ceilings and plenty of natural light. The spacious living room

    Steven Kwong CHARLES RUTENBERG REALTY ORLANDO

    812 Woodside Rd, Maitland, FL 32751
  • /20

    $2,375 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,721 Sq Ft
    • House for Rent

    2000 Sunderland Rd, Maitland, FL 32751

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2519.90. That covers your base rent, $2375.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    2000 Sunderland Rd, Maitland, FL 32751
  • /2

    $555,000

    Sold Oct 01, 2025

    1771 Chinook Trail, Maitland, FL 32751

    • 2 Beds
    • 2 Baths
    • 1,704 Sq Ft
    • Built 1959

    Last Sold Summary

    • 4% Below List Price
    • $326/SF
    • 20 Days On Market

    Current Estimated Value $570,315

    Last Listing Agent Hazel Sun RE/MAX 200 REALTY

    1771 Chinook Trail, Maitland, FL 32751
    • /2

      Est $379,958

      Not Listed For Sale

      294 Macarthur Place, Maitland, FL 32751

      294 Macarthur Place, Maitland, FL 32751

      Last Sold Summary

      • 121 Days On Market

      Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  • /41

    $830,000

    $45K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,136 Sq Ft

    2051 Dyan Way, Maitland, FL 32751

    Fantastic Maitland location! Situated on quiet cul-de-sac, this one-story 5 bedroom/4 bath, 3,136 sq ft ranch-style home is a short walk to A-rated Dommerich Elementary, Maitland Middle and Winter Park High. This one-story home sits on .29 of an acre that backs up to the preserved conservation. Functional floor plan with separate formal living and dining rooms, perfect for entertaining. Eat-in

    Megan Cross FANNIE HILLMAN & ASSOCIATES

    2051 Dyan Way, Maitland, FL 32751
  • /20

    $2,307 Per Month

    • 2 Beds
    • 2 Baths
    • 1,115 Sq Ft
    • Condo for Rent

    9301 Summit Centre Way Unit 1203, Orlando, FL 32810

    Landing is a top-rated, fully furnished apartment network with thousands of homes across 250+ U.S. cities. With premium amenities, a mobile app to manage your stay, and 24/7 support. Our apartments have everything you need for monthly and longer stays. 6-Month+ Stay base rent: starts at $2370/mo 12-Month+ Stay base rent: starts at $2307/mo Landing's apartments at The Tiffany at

    9301 Summit Centre Way Unit 1203, Orlando, FL 32810
  • /2

    $595,000

    Sold May 05, 2026

    2466 Fieldingwood Rd, Maitland, FL 32751

    • 4 Beds
    • 2 Baths
    • 1,765 Sq Ft
    • Built 1972

    Last Sold Summary

    • 1% Below List Price
    • $337/SF
    • 2 Days On Market

    Current Estimated Value $566,078

    Last Listing Agent Kristine McKinley RE/MAX TOWN & COUNTRY REALTY

    2466 Fieldingwood Rd, Maitland, FL 32751
    • /2

      Est $268,293

      Not Listed For Sale

      914 Park Lake Cir Unit 33, Maitland, FL 32751

      • 3 Beds
      • 3 Baths
      • 1,496 Sq Ft
      • Built 1972
      914 Park Lake Cir Unit 33, Maitland, FL 32751

      Last Sold Summary

      • 112 Days On Market

      Last Listing Agent Kim Foy SOUTHERN TRADITIONS REALTY LLC

  • /22

    $325,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,240 Sq Ft

    7917 Plunkett Ave, Orlando, FL 32810

    Under contract-accepting backup offers. Welcome to 7917 Plunkett Avenue, a move-in-ready 3-bedroom, 2-bath Orlando home with a 2-car garage on nearly a 1/4 acre with a fenced backyard. Fresh interior paint (2026) gives the home a clean, updated feel, while the backyard offers plenty of room to entertain, play, garden, or simply enjoy the Florida sunshine.Improvements include whole home

    Jill Healey KELLER WILLIAMS WINTER PARK

    7917 Plunkett Ave, Orlando, FL 32810
  • /20

    $1,827 Per Month

    • 1 Bed
    • 1 Bath
    • 712 Sq Ft
    • Condo for Rent

    9301 Summit Centre Way Unit 1317, Orlando, FL 32810

    Landing is a top-rated, fully furnished apartment network with thousands of homes across 250+ U.S. cities. With premium amenities, a mobile app to manage your stay, and 24/7 support. Our apartments have everything you need for monthly and longer stays. 6-Month+ Stay base rent: starts at $1878/mo 12-Month+ Stay base rent: starts at $1827/mo Landing's apartments at The Tiffany at

    9301 Summit Centre Way Unit 1317, Orlando, FL 32810
  • /2

    $239,000

    Sold May 08, 2026

    602 Villa Cir Unit 543, Maitland, FL 32751

    • 3 Beds
    • 2 Baths
    • 1,256 Sq Ft
    • Built 1979

    Last Sold Summary

    • 4% Below List Price
    • $190/SF
    • 49 Days On Market

    Current Estimated Value $240,108

    Last Listing Agent Odel Ximinies COLDWELL BANKER REALTY

    602 Villa Cir Unit 543, Maitland, FL 32751
    • /2

      Est $351,004

      Not Listed For Sale

      1010 Winderley Place Unit 139, Maitland, FL 32751

      • 3 Beds
      • 2.5 Baths
      • 1,651 Sq Ft
      • Built 1999
      1010 Winderley Place Unit 139, Maitland, FL 32751

      Last Sold Summary

      • 84 Days On Market

      Last Listing Agent Jesse Sobel COMPASS FLORIDA LLC

  • /29

    $315,000

    • 2 Beds
    • 1.5 Baths
    • 816 Sq Ft

    1140 S Orlando Ave Unit G3, Maitland, FL 32751

    Completely renovated and move-in ready, a desired first-floor unit in the sought-after Lake Maitland Terrace! This impeccably updated two-bedroom, 1.5-bath condominium blends modern style with an unbeatable lakeside location in the heart of the Maitland/Winter Park area. Thoughtfully redesigned throughout, the home showcases a new kitchen with fresh cabinetry, granite countertops and stainless

    Drew Henner PREMIER SOTHEBY'S INTL. REALTY

    1140 S Orlando Ave Unit G3, Maitland, FL 32751
  • /20

    $1,826 Per Month

    • 1 Bed
    • 1 Bath
    • 712 Sq Ft
    • Condo for Rent

    9301 Summit Centre Way Unit 1313, Orlando, FL 32810

    Landing is a top-rated, fully furnished apartment network with thousands of homes across 250+ U.S. cities. With premium amenities, a mobile app to manage your stay, and 24/7 support. Our apartments have everything you need for monthly and longer stays. 6-Month+ Stay base rent: starts at $1883/mo 12-Month+ Stay base rent: starts at $1826/mo Landing's apartments at The Tiffany at

    9301 Summit Centre Way Unit 1313, Orlando, FL 32810
  • /2

    $515,000

    Sold Nov 07, 2025

    2162 Lake Howell Preserve Ct, Maitland, FL 32751

    • 3 Beds
    • 3.5 Baths
    • 2,188 Sq Ft
    • Built 2021

    Last Sold Summary

    • 6% Below List Price
    • $235/SF
    • 27 Days On Market

    Last Listing Agent Mark Raumaker SERHANT

    2162 Lake Howell Preserve Ct, Maitland, FL 32751
    • /2

      Est $310,859

      Not Listed For Sale

      1000 Winderley Place Unit 143, Maitland, FL 32751

      • 3 Beds
      • 2 Baths
      • 1,538 Sq Ft
      • Built 1982
      1000 Winderley Place Unit 143, Maitland, FL 32751

      Last Sold Summary

      • 135 Days On Market

      Last Listing Agent Sandi Peery RE/MAX TOWN & COUNTRY REALTY

  • /20

    $714,990

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,495 Sq Ft

    1741 Lyndale Blvd, Maitland, FL 32751

    Charming Newly Renovated Bungalow in Prime Maitland Location – Move-In Ready with Endless Potential! Discover this beautifully updated 3-bedroom, 2-bath bungalow at 1741 Lyndale Blvd, Maitland, FL 32751 – perfectly positioned on the edge of Winter Park for an unbeatable blend of tranquility and convenience. Freshly renovated and move-in ready, this home offers immediate comfort while situated in

    Robert Dion D & D PROPERTY MANAGEMENT SOLUTIONS LLC

    1741 Lyndale Blvd, Maitland, FL 32751
  • /20

    $1,881 Per Month

    • 1 Bed
    • 1 Bath
    • 805 Sq Ft
    • Condo for Rent

    9301 Summit Centre Way Unit 3225, Orlando, FL 32810

    Landing is a top-rated, fully furnished apartment network with thousands of homes across 250+ U.S. cities. With premium amenities, a mobile app to manage your stay, and 24/7 support. Our apartments have everything you need for monthly and longer stays. 6-Month+ Stay base rent: starts at $1931/mo 12-Month+ Stay base rent: starts at $1881/mo Landing's apartments at The Tiffany at

    9301 Summit Centre Way Unit 3225, Orlando, FL 32810
  • /2

    $335,000

    Sold Oct 03, 2025

    180 N Lakewood Cir, Maitland, FL 32751

    • 3 Beds
    • 2 Baths
    • 1,050 Sq Ft
    • Built 1971

    Last Sold Summary

    • 22% Below List Price
    • $319/SF
    • 301 Days On Market

    Current Estimated Value $324,463

    Last Listing Agent Todd Norwood BESPOKE REAL ESTATE

    180 N Lakewood Cir, Maitland, FL 32751
    • /2

      Est $313,832

      Not Listed For Sale

      416 Citrus Ln, Maitland, FL 32751

      • 3 Beds
      • 2 Baths
      • 1,254 Sq Ft
      • Built 1983
      416 Citrus Ln, Maitland, FL 32751

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Rick Bosley KELLER WILLIAMS ADVANTAGE REALTY

  • /63

    $249,000

    $10K PRICE DROP
    • 2 Beds
    • 3 Baths
    • 1,328 Sq Ft

    1713 Gulfview Dr Unit 435B, Maitland, FL 32751

    Welcome home to this beautifully updated two-story condo nestled in one of Maitland's most established communities, where lush mature landscaping, winding sidewalks, a community pool, lake access and a private dock create a peaceful setting just minutes from some of Central Florida's favorite restaurants, shopping and entertainment. Enjoy easy access to Enzian Theater, Winter Park Village, Trader

    Becki Douglas MAINFRAME REAL ESTATE

    1713 Gulfview Dr Unit 435B, Maitland, FL 32751
  • /3

    $799 Per Month

    • 1 Bed
    • 1 Bath
    • House for Rent

    312 Orange St, Maitland, FL 32751

    Property Id: 1769832 Maitland, FL 32751 Beautiful house with shared living space.

    312 Orange St, Maitland, FL 32751
  • /2

    $1,350,000

    Sold Oct 01, 2025

    2047 Howell Branch Rd, Maitland, FL 32751

    • 4 Beds
    • 2 Baths
    • 2,960 Sq Ft
    • Built 1986

    Last Sold Summary

    • 10% Below List Price
    • $456/SF
    • 28 Days On Market

    Current Estimated Value $1,359,075

    Last Listing Agent Shelby Smith KELLY PRICE & COMPANY LLC

    2047 Howell Branch Rd, Maitland, FL 32751
    • /2

      Est $293,804

      Not Listed For Sale

      1000 Winderley Place Unit 221, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 1,275 Sq Ft
      • Built 1982
      1000 Winderley Place Unit 221, Maitland, FL 32751

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Jean Chalifour COLDWELL BANKER REALTY

  • /9

    $3,990,900

    $500K PRICE DROP
    • Land
    • 7.82 Acres
    • $510,345 per Acre

    1250 N Maitland Ave, Maitland, FL 32751

    Exceptional opportunity for commercial developers, residential builders, or those seeking a private estate within the City of Maitland, Orange County. This rare offering includes approximately ±8 acres of usable land comprising multiple contiguous parcels and rights-of-way. The property is designated as a Traditional Neighborhood and zoned RS-2. A previously submitted Planned Development

    Armando Gonzalez AG REALTY SERVICES LLC

    1250 N Maitland Ave, Maitland, FL 32751
  • /20

    $2,291 Per Month

    • 2 Beds
    • 2 Baths
    • 1,115 Sq Ft
    • Condo for Rent

    9301 Summit Centre Way Unit 2324, Orlando, FL 32810

    Landing is a top-rated, fully furnished apartment network with thousands of homes across 250+ U.S. cities. With premium amenities, a mobile app to manage your stay, and 24/7 support. Our apartments have everything you need for monthly and longer stays. 6-Month+ Stay base rent: starts at $2325/mo 12-Month+ Stay base rent: starts at $2291/mo Landing's apartments at The Tiffany at

    9301 Summit Centre Way Unit 2324, Orlando, FL 32810
  • /2

    $469,450

    Sold Jul 01, 2026

    1928 South Blvd, Maitland, FL 32751

    • 4 Beds
    • 2 Baths
    • 1,879 Sq Ft
    • Built 1969

    Last Sold Summary

    • 2% Below List Price
    • $250/SF
    • 3 Days On Market

    Current Estimated Value $477,615

    Last Listing Agent Doori Sung LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

    1928 South Blvd, Maitland, FL 32751
    • /2

      Not Listed For Sale

      1000 S Orlando Ave Unit 2, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 952 Sq Ft
      • Built 1964
      1000 S Orlando Ave Unit 2, Maitland, FL 32751

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Loralee Rider RIDER REALTY, LLC

  • /36

    $229,000

    • 2 Beds
    • 1.5 Baths
    • 1,353 Sq Ft

    856 Park Lake Cir Unit 51, Maitland, FL 32751

    LOCATION LOCATION LOCATION! The Park Lake Townhome Community is Maitland's hidden treasure! Offering for sale this well-maintained townhome with 2 levels of comfortable living, a one-car garage, a nice sized laundry room under air, along with a private screened back patio. As you step inside, look over your shoulder at the community pool that is literally steps from your front door! Once inside

    Jill Henry COLDWELL BANKER REALTY

    856 Park Lake Cir Unit 51, Maitland, FL 32751
  • /2

    $3,950 Per Month

    • 4 Beds
    • 2 Baths
    • 1,992 Sq Ft
    • House for Rent

    1911 Mohican Trail, Maitland, FL 32751

    Welcome home to 1911 Mohican Drive, a beautifully maintained 4-bedroom, 2-bathroom rental nestled in the highly sought-after Dommerich neighborhood of Maitland. Perfectly situated on a large corner lot, this home offers wonderful separation of space with distinct living, dining, and family rooms, giving everyone room to spread out and relax. The family room flows seamlessly outdoors through glass

    Kelly Price KELLY PRICE & COMPANY LLC

    1911 Mohican Trail, Maitland, FL 32751
  • /2

    $650,000

    Sold May 21, 2026

    2600 Mohawk Trail, Maitland, FL 32751

    • 4 Beds
    • 2.5 Baths
    • 2,265 Sq Ft
    • Built 1965

    Last Sold Summary

    • 3% Below List Price
    • $287/SF
    • 42 Days On Market

    Current Estimated Value $655,574

    Last Listing Agent Anthony Consalvo FLORIDA ONE REAL ESTATE LLC

    2600 Mohawk Trail, Maitland, FL 32751
    • /2

      Est $173,178

      Not Listed For Sale

      222 Cherrywood Gardens Dr Unit 7, Maitland, FL 32751

      • 2 Beds
      • 1.5 Baths
      • 953 Sq Ft
      • Built 1974
      222 Cherrywood Gardens Dr Unit 7, Maitland, FL 32751

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent Allison Day RE/MAX TOWN & COUNTRY REALTY

  • /34

    $1,800,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 3,567 Sq Ft

    1130 Mechanic St, Maitland, FL 32751

    Pre-Construction. To be built. Come build your dream home on this exceptional homesite in the heart of Maitland.This stunning new construction single-family residence will feature 4 bedrooms, 4.5 bathrooms, and 3,567 square feet of thoughtfully designed living space across two stories, showcasing sleek modern finishes and open-concept living ideal for today’s lifestyle. Set on a 0.26-acre

    Richard Palmano PALMANO GROUP RE BROKERAGE LLC

    1130 Mechanic St, Maitland, FL 32751
  • /18

    $2,550 Per Month

    • 2 Beds
    • 1 Bath
    • 1,104 Sq Ft
    • Condo for Rent

    245 Orange Place Unit 245 Orange Pl, Maitland, FL 32751

    Updated 2/1 House Available Now!245 Orange Place, Maitland, FL 32751This property has 2 bedrooms, 1 bathroom and approximately 1100 sqft of floor space.This unit will not last long!Apartment Features:2 cozy bedrooms1 updated bathroomIn-unit washer & dryerDedicated off-street parkingUnbeatable location just 2 blocks from Winter

    245 Orange Place Unit 245 Orange Pl, Maitland, FL 32751
  • /2

    $900,000

    Sold Mar 03, 2026

    1619 Druid Rd, Maitland, FL 32751

    • 5 Beds
    • 4 Baths
    • 3,769 Sq Ft
    • Built 1958

    Last Sold Summary

    • 5% Below List Price
    • $239/SF
    • 30 Days On Market

    Current Estimated Value $904,452

    Last Listing Agent Mark Adams KELLER WILLIAMS REALTY AT THE PARKS

    1619 Druid Rd, Maitland, FL 32751
    • /2

      Est $409,612

      Not Listed For Sale

      1930 Rogers Ave, Maitland, FL 32751

      • 3 Beds
      • 2 Baths
      • 1,625 Sq Ft
      • Built 2024
      1930 Rogers Ave, Maitland, FL 32751

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Adrian Shipp KELLER WILLIAMS CLASSIC

  • /39

    $450,000

    $9K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,154 Sq Ft

    761 Robinhood Dr, Maitland, FL 32751

    Virtually Staged. PRICED BELOW APPRAISAL! Exceptional value in a desirable Maitland location! Whether you’re starting out, slowing down or somewhere in between, this home is a must see. Beautifully renovated in 2026, this move-in-ready home features new windows, flooring, hot water tank, entry and garage doors, as well as new exterior siding and the roof and HVAC were replaced in 2023. Soaring

    Cheryl Geluso RE/MAX ASSURED

    761 Robinhood Dr, Maitland, FL 32751
  • /27

    $2,200 Per Month

    • 2 Beds
    • 2 Baths
    • 1,275 Sq Ft
    • Condo for Rent

    1000 Winderley Place Unit 128, Maitland, FL 32751

    Welcome to your own tropical retreat! This spacious 2-bedroom, 2-bath residence invites you in with warmth, light, and character.Rich cherry wood floors enhance the living and dining areas, while bathrooms feature elegant travertine stone finishes. The kitchen shines with granite countertops and stainless-steel appliances, while the open layout, cozy fireplace, and oversized sliding doors

    Roxana Barea DOVER INTERNATIONAL CO., INC.

    1000 Winderley Place Unit 128, Maitland, FL 32751
  • /2

    $410,000

    Sold Aug 03, 2026

    200 Moseley Ave, Maitland, FL 32751

    • 3 Beds
    • 2 Baths
    • 1,625 Sq Ft
    • Built 2026

    Last Sold Summary

    • 11% Below List Price
    • $252/SF
    • 34 Days On Market

    Current Estimated Value $350,799

    Last Listing Agent Brianna Grant SYCHAR REALTY

    200 Moseley Ave, Maitland, FL 32751
    • /22

      Est $260,162

      Not Listed For Sale

      1714 Gulfview Dr Unit 427-C, Maitland, FL 32751

      • 3 Beds
      • 3 Baths
      • 1,328 Sq Ft
      • Built 1981
      1714 Gulfview Dr Unit 427-C, Maitland, FL 32751

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Yien Yao KELLER WILLIAMS ADVANTAGE 2 REALTY

Showing Results 161 - 200, Page 5 of 18

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