9,991

Maitland, FL Homes

Section Image
  • /20

    $719,990

    $10K 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

    $1,892 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 $1892/mo12-Month+ Stay base rent: starts at $1892/moLanding's apartments at The Tiffany at

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

    $255,000

    Sold Dec 08, 2025

    240 Cherrywood Dr, Maitland, FL 32751

    • 3 Beds
    • 2 Baths
    • 1,161 Sq Ft
    • Built 1959

    Last Sold Summary

    • 9% Below List Price
    • $220/SF
    • 6 Days On Market

    Current Estimated Value $261,426

    Last Listing Agent Martha Grasty EXP REALTY LLC

    240 Cherrywood Dr, Maitland, FL 32751
    • /2

      Est $403,920

      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

  • /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

    $1,892 Per Month

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

    9301 Summit Centre Way Unit 1303, 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 $1892/mo12-Month+ Stay base rent: starts at $1892/moLanding's apartments at The Tiffany at

    9301 Summit Centre Way Unit 1303, Orlando, FL 32810
  • /2

    $330,000

    Sold Dec 30, 2025

    735 Gamewell Ave, Maitland, FL 32751

    • 2 Beds
    • 1 Bath
    • 938 Sq Ft
    • Built 1952

    Last Sold Summary

    • $352/SF
    • 2 Days On Market

    Current Estimated Value $332,641

    Last Listing Agent Heather Pryor KELLER WILLIAMS ADVANTAGE REALTY

    735 Gamewell Ave, Maitland, FL 32751
    • /22

      Est $259,616

      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

  • /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
  • /20

    $1,892 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 $1892/mo12-Month+ Stay base rent: starts at $1892/moLanding's apartments at The Tiffany at

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

    $385,000

    Sold Feb 24, 2026

    210 Magnolia Rd Unit 106, Maitland, FL 32751

    • 3 Beds
    • 2 Baths
    • 1,394 Sq Ft
    • Built 1971

    Last Sold Summary

    • 4% Below List Price
    • $276/SF
    • 16 Days On Market

    Current Estimated Value $383,417

    Last Listing Agent Sue Gilman KELLER WILLIAMS WINTER PARK

    210 Magnolia Rd Unit 106, Maitland, FL 32751
    • /2

      Est $334,819

      Not Listed For Sale

      472 Citrus Ln, Maitland, FL 32751

      • 3 Beds
      • 2.5 Baths
      • 1,665 Sq Ft
      • Built 1983
      472 Citrus Ln, Maitland, FL 32751

      Last Sold Summary

      • 91 Days On Market

  • /46

    $999,000

    $101K PRICE DROP Pending
    • 4 Beds
    • 3 Baths
    • 2,300 Sq Ft

    921 N Thistle Ln, Maitland, FL 32751

    Under contract-accepting backup offers. Fully renovated pool home in the heart of Dommerich featuring a rare dual-primary layout and a 2019-built owner’s suite addition—designed for modern living and effortless maintenance. Originally built in 1967 and completely reimagined in 2019, the home blends timeless character with major system upgrades including roof, HVAC, plumbing, electrical, windows,

    Garrett McGinnis VISTA NATIONAL MANAGEMENT INC

    921 N Thistle Ln, Maitland, FL 32751
  • /20

    $1,956 Per Month

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

    9301 Summit Centre Way Unit 4218, 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 $1956/mo12-Month+ Stay base rent: starts at $1956/moLanding's apartments at The Tiffany at

    9301 Summit Centre Way Unit 4218, Orlando, FL 32810
  • /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 $564,761

    Last Listing Agent Hazel Sun RE/MAX 200 REALTY

    1771 Chinook Trail, Maitland, FL 32751
    • /2

      Est $273,528

      Not Listed For Sale

      854 Town Cir Unit 116, Maitland, FL 32751

      • 3 Beds
      • 2.5 Baths
      • 1,565 Sq Ft
      • Built 1974
      854 Town Cir Unit 116, Maitland, FL 32751

      Last Sold Summary

      • 18 Days On Market

  • /30

    $598,000

    • 4 Beds
    • 2 Baths
    • 2,667 Sq Ft

    1241 Manchester Rd, Maitland, FL 32751

    Welcome to English Estates, one of Maitland’s most desirable neighborhoods. This 4-bedroom, 2-bath home has been thoughtfully updated and is ready for its next owner. The home features an open living area, updated kitchen and bathrooms, new plumbing, a new roof, a flex room, screened lanai, and a spacious backyard. Conveniently located near shopping, restaurants, parks, and major roadways,

    1241 Manchester Rd, Maitland, FL 32751
  • /11

    $1,850 Per Month

    • 3 Beds
    • 1 Bath
    • 1,409 Sq Ft
    • House for Rent

    523 Oak Ave, Maitland, FL 32751

    Nestled in a peaceful, wooded setting in desirable Maitland, this charming 3-bedroom, 1-bath home offers a comfortable layout and convenient location. The home features both a spacious living room and a separate family room, providing plenty of space for relaxing, entertaining, or working from home. A dedicated laundry room with washer and dryer hookups adds everyday convenience, while the

    523 Oak Ave, Maitland, FL 32751
  • /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 $553,297

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

    2466 Fieldingwood Rd, Maitland, FL 32751
    • /2

      Not Listed For Sale

      1000 S Orlando Ave Unit 5, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 952 Sq Ft
      • Built 1964
      1000 S Orlando Ave Unit 5, Maitland, FL 32751

      Last Sold Summary

      • 41 Days On Market

  • /24

    $139,900

    $10K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,048 Sq Ft

    1150 Lake Shadow Cir Unit 3304, Maitland, FL 32751

    Sought-after Visconti community of Maitland. The lowest 2-2 entry point currently available. This third-floor, 2-bed, 2-bath, 1,048 sqft condo features updated flooring, designer paint, LED lighting, new ceiling fans, updated faucets, and a screened patio with exterior storage. Community amenities include two pools overlooking Lake Shadow, tennis courts, lakeside walking paths, dog stations, and

    Scott Fader JOSEPH WALTER REALTY LLC

    1150 Lake Shadow Cir Unit 3304, Maitland, FL 32751
  • /20

    $1,892 Per Month

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

    9301 Summit Centre Way Unit 2313, 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 $1892/mo12-Month+ Stay base rent: starts at $1892/moLanding's apartments at The Tiffany at

    9301 Summit Centre Way Unit 2313, 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 $245,485

    Last Listing Agent Odel Ximinies COLDWELL BANKER REALTY

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

      Est $214,656

      Not Listed For Sale

      1501 Grove St Unit 560, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 1,087 Sq Ft
      • Built 1979
      1501 Grove St Unit 560, Maitland, FL 32751

      Last Sold Summary

      • 57 Days On Market

  • /35

    $619,900

    $30K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,236 Sq Ft

    140 Wigwam Place, Maitland, FL 32751

    Virtually Staged. Tucked away on a cul-de-sac in beautiful Maitland, this 3-bedroom, 3-bath home with a bonus room offers space, comfort, and privacy on a generous 1/3-acre lot. With 2,236 square feet of living space and a 2-car garage, the home features an updated kitchen and upgraded bathrooms, blending modern touches with everyday functionality. Enjoy cozy evenings by the fireplace or relax in

    Blake Bolton LPT REALTY, LLC

    140 Wigwam Place, Maitland, FL 32751
  • /20

    $1,892 Per Month

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

    9301 Summit Centre Way Unit 1223, 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 $1892/mo12-Month+ Stay base rent: starts at $1892/moLanding's apartments at The Tiffany at

    9301 Summit Centre Way Unit 1223, 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 $213,255

      Not Listed For Sale

      1225 Lake Shadow Cir Unit 14202, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 1,111 Sq Ft
      • Built 2000
      1225 Lake Shadow Cir Unit 14202, Maitland, FL 32751

      Last Sold Summary

      • 55 Days On Market

  • /62

    $975,000

    $25K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 3,049 Sq Ft

    755 Woodside Rd, Maitland, FL 32751

    This is the one you've been waiting for- a SLEEK MODERN HOME, where EVERY MAJOR SYSTEM AND FINISH has been REPLACED, REFRESHED and ELEVATED to perfection and minutes from Winter Park without the WP price tag! Located at 755 Woodside Road in the community of Forest Brook in Maitland with 3,054 Sq Ft. of living space, in a quiet CUL-DE- SAC, this 3 BEDROOM 3 FULL BATHROOM POOL home with 2 Car

    Diane Heiken EMPIRE NETWORK REALTY

    755 Woodside Rd, Maitland, FL 32751
  • /15

    $2,400 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,015 Sq Ft
    • House for Rent

    31 Bel Air St, Eatonville, FL 32751

    Step into comfort and convenience with this 3-bedroom, 1.5-bath home that offers room to live and relax. Featuring both a welcoming living room and a separate family room, this layout provides the perfect balance of gathering spaces and cozy retreats.The kitchen and common areas flow seamlessly, making everyday living easy and enjoyable. A dedicated laundry room with washer and dryer

    31 Bel Air St, Eatonville, FL 32751
  • /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 $319,739

    Last Listing Agent Todd Norwood BESPOKE REAL ESTATE

    180 N Lakewood Cir, Maitland, FL 32751
    • /40

      Est $320,667

      Not Listed For Sale

      1010 Winderley Place Unit 131, Maitland, FL 32751

      • 3 Beds
      • 2.5 Baths
      • 1,563 Sq Ft
      • Built 1997
      1010 Winderley Place Unit 131, Maitland, FL 32751

      Last Sold Summary

      • 17 Days On Market

  • /33

    $467,000

    $15K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,270 Sq Ft

    204 Quayside Cir Unit 201, Maitland, FL 32751

    Updated 2 bedroom 2 bathroom located on the second floor of sought after Moorings Lakefront Community with spectacular views of Lake Maitland of the Winter Park Chain of Lakes. The condo offers a large screened-in balcony overlooking Lake Maitland. The open floorpan offers a split plan with a generous size master retreat with a private door to the balcony and a secondary ensuite. The updated

    Angel Reyes COLDWELL BANKER REALTY

    204 Quayside Cir Unit 201, Maitland, FL 32751
  • /13

    $1,575

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,048 Sq Ft
    • Condo for Rent

    1408 Lake Shadow Cir Unit 1105, Maitland, FL 32751

    Beautiful 2-Bedroom Condo in Gated Community – Visconti West, MaitlandWelcome to your new home in one of Maitland’s most sought-after gated communities! This spacious and stylish 2-bedroom, 2-bathroom condo offers comfort, convenience, and access to top-notch amenities.Features:- Granite countertops in both kitchen and bathrooms- Two large bedrooms with walk-in

    1408 Lake Shadow Cir Unit 1105, 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 $1,342,541

    Last Listing Agent Shelby Smith KELLY PRICE & COMPANY LLC

    2047 Howell Branch Rd, Maitland, FL 32751
    • /22

      Est $185,119

      Not Listed For Sale

      216 Cherrywood Gardens Dr Unit 216, Maitland, FL 32751

      • 2 Beds
      • 1.5 Baths
      • 953 Sq Ft
      • Built 1974
      216 Cherrywood Gardens Dr Unit 216, Maitland, FL 32751

      Last Sold Summary

      • 3 Days On Market

  • /37

    $1,149,900

    Pending
    • 4 Beds
    • 4.5 Baths
    • 3,040 Sq Ft

    766 Terra Place, Maitland, FL 32751

    Under contract-accepting backup offers. Virtually Staged. Private Pool Retreat with Two Primary Suites in Terra Place. Nestled in Terra Place, one of Maitland’s best-kept-secret neighborhoods, where every street ends in a cul-de-sac and a community park is just steps away, this custom one-story pool home offers space, privacy, and functionality—with no mandatory HOA. Soaring cathedral ceilings,

    Chris Creegan CREEGAN GROUP

    766 Terra Place, Maitland, FL 32751
  • /3

    $1,375

    Total Monthly Price

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

    1125 Lake Shadow Cir Unit 5-101, Maitland, FL 32751

    Located in the Beautiful Gated Visconti condos in Maitland, FL. Clubhouse and pool amenities, work out room and more.This unit is 1st floor (no stairs) corner unit (More privacy).Washer and dryer included. Water and trash pick up included.No pets allowed.

    1125 Lake Shadow Cir Unit 5-101, Maitland, FL 32751
  • /2

    $960,000

    Sold Sep 02, 2025

    2106 Tuscarora Trail, Maitland, FL 32751

    • 4 Beds
    • 3 Baths
    • 2,949 Sq Ft
    • Built 1961

    Last Sold Summary

    • 2% Below List Price
    • $326/SF
    • 65 Days On Market

    Current Estimated Value $947,520

    Last Listing Agent Brian Teach COLDWELL BANKER REALTY

    2106 Tuscarora Trail, Maitland, FL 32751
    • /34

      Est $265,021

      Not Listed For Sale

      852 Park Lake Cir Unit 49, Maitland, FL 32751

      • 3 Beds
      • 3 Baths
      • 1,496 Sq Ft
      • Built 1972
      852 Park Lake Cir Unit 49, Maitland, FL 32751

      Last Sold Summary

      • 43 Days On Market

Showing Results 161 - 200, Page 5 of 18

How to Buy a Home How to Finance a Home How to Sell a Home