9,992

Maitland, FL Homes

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  • /45

    $199,000

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

    1440 Lake Shadow Cir Unit 8201, Maitland, FL 32751

    If you are looking for a terrific property, look no further! You or your tenant can live the lifestyle deserved in this RESORT-STYLE, video-monitored GATED COMMUNITY located on beautiful Lake Shadow in the heart of Maitland Center. This two-bed/two-bath, 2nd-story, CORNER UNIT features an OPEN floor plan with a LIVING/DINING COMBO and 9-FOOT CEILINGS. The KITCHEN includes a breakfast bar, closet

    Susan Schneider COLDWELL BANKER REALTY

    1440 Lake Shadow Cir Unit 8201, Maitland, FL 32751
  • /25

    $2,149 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,201 Sq Ft
    • Townhouse for Rent

    916 Robinhood Ct, Maitland, FL 32751

    Welcome home! This 3-bedroom, 1.5-bath DUPLEX is available for June 10th 2026. Includes a fenced-in backyard. Located conveniently in the desirable City of Maitland, this property is close to the shopping district, Hospital district, Winter Park shopping, and I-4. This property features a comfortable layout with well-apportioned bedrooms and bathrooms. Washer and dryer included. Act now! This one

    916 Robinhood Ct, Maitland, FL 32751
  • /2

    $549,000

    Sold Jun 01, 2026

    2021 Mohican Trail, Maitland, FL 32751

    • 3 Beds
    • 2 Baths
    • 1,798 Sq Ft
    • Built 1962

    Last Sold Summary

    • $305/SF
    • 0 Days On Market

    Current Estimated Value $567,139

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

    2021 Mohican Trail, Maitland, FL 32751
    • /19

      Est $362,838

      Not Listed For Sale

      215 Eaton St, Maitland, FL 32751

      • 3 Beds
      • 2 Baths
      • 1,982 Sq Ft
      • Built 2023
      215 Eaton St, Maitland, FL 32751

      Last Sold Summary

      • 5 Days On Market

  • /37

    $519,000

    Open Sun 11AM - 1PM
    • 3 Beds
    • 2 Baths
    • 1,929 Sq Ft

    1065 Gregory Dr, Maitland, FL 32751

    VIDEO/VIRTUAL TOUR AVAILABLE! This Maitland pool home features 3 bed/2 bath in the main house with a 4th room addition on the other side of the garage. The 4th room has it's own separate entrance and it's own rear door access to the pool! Use it as a home office, creative studio, home gym, or income-producing suite — with no HOA to answer to. The cozy fireplace, hardwood floors, and split bedroom

    Cece Wong EXP REALTY LLC

    1065 Gregory Dr, Maitland, FL 32751
  • /12

    $1,575 Per Month

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • House for Rent

    301 Clark St Unit 2, Maitland, FL 32751

    Charming 2-Bedroom, 1-Bath Rental in the Heart of MaitlandWelcome to this cozy and private 2-bedroom, 1-bath rental, perfectly situated in the desirable Maitland area. This well maintained unit offers a warm and inviting living area along with a functional kitchen equipped with a stove and microwave, ideal for comfortable, everyday living.Enjoy true peace of mind with water and

    Laury Cruz Penalo De Gomez MY REALTY GROUP, LLC.

    301 Clark St Unit 2, Maitland, FL 32751
  • /2

    $525,000

    Sold Jun 26, 2025

    510 W Faith Terrace, Maitland, FL 32751

    • 3 Beds
    • 2 Baths
    • 1,672 Sq Ft
    • Built 1960

    Last Sold Summary

    • $314/SF
    • 7 Days On Market

    Current Estimated Value $501,911

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    510 W Faith Terrace, Maitland, FL 32751
    • /29

      Est $194,314

      Not Listed For Sale

      1375 Lake Shadow Cir Unit 11301, Maitland, FL 32751

      • 2 Beds
      • 1 Bath
      • 898 Sq Ft
      • Built 2000
      1375 Lake Shadow Cir Unit 11301, Maitland, FL 32751

      Last Sold Summary

      • 124 Days On Market

  • /33

    $458,500

    $57K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,270 Sq Ft

    204 Quayside Cir Unit 504, Maitland, FL 32751

    Seller to pay up to one year of HOA! Wake up to shimmering lake views and unwind each evening with breathtaking Florida sunsets in this beautifully refreshed 2-bedroom, 2-bathroom condo. From the moment you step off the elevator, you’re welcomed into a light-filled, open-concept living space highlighted by oversized glass sliding doors that lead to a private enclosed patio—seamlessly blending

    Allison Hunter LUXE HUNTER REAL ESTATE

    204 Quayside Cir Unit 504, Maitland, FL 32751
  • /12

    $1,300 Per Month

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • Townhouse for Rent

    1820 Rogers Ave, Maitland, FL 32751

    Introducing a stunning renovated 2 bedroom, 1 bathroom duplex with top-of-the-line upgrades. This property boasts beautiful stainless steel appliances, sleek new flooring, and gorgeous granite countertops that are sure to impress. The modern cabinets provide ample storage space and complete the sleek and stylish design. With attention to detail and quality craftsmanship, this duplex offers a

    1820 Rogers Ave, Maitland, FL 32751
  • /2

    $525,000

    Sold Jan 22, 2026

    1220 Winston Rd, Maitland, FL 32751

    • 4 Beds
    • 2 Baths
    • 1,724 Sq Ft
    • Built 1964

    Last Sold Summary

    • 5% Above List Price
    • $305/SF
    • 3 Days On Market

    Current Estimated Value $510,076

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

    1220 Winston Rd, Maitland, FL 32751
    • /34

      Est $306,397

      Not Listed For Sale

      810 Town Cir Unit 158, Maitland, FL 32751

      • 3 Beds
      • 2.5 Baths
      • 1,565 Sq Ft
      • Built 1975
      810 Town Cir Unit 158, Maitland, FL 32751

      Last Sold Summary

      • 7 Days On Market

  • /23

    $675,000

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

    245 Orange Place, Maitland, FL 32751

    Location, location!! Discover a rare opportunity to own a single family home plus 2 ADUs, just steps from the iconic Enzian Theater and vibrant Downtown Maitland. This property features three separate units, each with three separate electric meters, water meters and IN-UNIT washer and dryers - a highly sought-after feature for both tenants and owner-occupants alike.With all exterior siding

    Jessica Lee ONE LUXURY INTERNATIONAL LLC

    245 Orange Place, Maitland, FL 32751
  • /30

    $2,250 Per Month

    • 3 Beds
    • 2 Baths
    • 1,323 Sq Ft
    • House for Rent

    16 Eaton St, Maitland, FL 32751

    Bright and airy 3-bedroom, 2-bath home with laminate flooring throughout. The spacious kitchen offers ample counter space and opens to the living area. Enjoy a large, low-maintenance backyard with turf. Convenient to everything Maitland and Winter Park have to offer. Washer and dryer included.

    Franki Gonzalez DALTON WADE INC

    16 Eaton St, Maitland, FL 32751
  • /2

    $995,000

    Sold Oct 27, 2025

    1630 Chinook Trail, Maitland, FL 32751

    • 3 Beds
    • 3 Baths
    • 2,742 Sq Ft
    • Built 1966

    Last Sold Summary

    • $363/SF
    • 33 Days On Market

    Current Estimated Value $980,055

    Last Listing Agent Darein Washington KELLER WILLIAMS ADVANTAGE REALTY

    1630 Chinook Trail, Maitland, FL 32751
    • /33

      Est $271,383

      Not Listed For Sale

      800 Town Cir Unit 153, Maitland, FL 32751

      • 3 Beds
      • 2.5 Baths
      • 1,565 Sq Ft
      • Built 1975
      800 Town Cir Unit 153, Maitland, FL 32751

      Last Sold Summary

      • 54 Days On Market

  • /71

    $495,000

    $33K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,909 Sq Ft

    653 Green Meadow Ave, Maitland, FL 32751

    One or more photo(s) has been virtually staged. Seller Motivated. Location, Location, Welcome to your new 4 BED 2 BATH home tucked away on a quiet cul-de-sac street in the desirable Maitland community of "Forest Brook"This one-of-a-kind home offers the perfect blend of charm, space, and functionality. Lovingly maintained, the home welcomes youwith a grand Foyer, Formal Living and Dinng

    Deanna Chance A+ REALTY PROFESSIONALS, INC

    653 Green Meadow Ave, Maitland, FL 32751
  • /11

    $2,595 Per Month

    • 3 Beds
    • 2 Baths
    • 1,893 Sq Ft
    • House for Rent

    510 Oak Ln, Maitland, FL 32751

    Beautiful 3-Bedroom, 2-Bath Home Available Now!This well-maintained home features a spacious family room that is perfect for entertaining and everyday living. The upgraded kitchen offers abundant counter space, stainless steel appliances, and a cozy breakfast nook/dining area.Additional features include:• Indoor laundry room with washer and dryer included• No carpet throughout

    510 Oak Ln, Maitland, FL 32751
  • /2

    $1,165,000

    Sold Feb 17, 2026

    1750 Cheyenne Trail, Maitland, FL 32751

    • 5 Beds
    • 3 Baths
    • 2,868 Sq Ft
    • Built 2014

    Last Sold Summary

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

    Current Estimated Value $1,162,819

    Last Listing Agent Kyle Grafton FANNIE HILLMAN & ASSOCIATES

    1750 Cheyenne Trail, Maitland, FL 32751
    • /11

      Not Listed For Sale

      0 Lake Howell Rd Unit MFRO6116578, Maitland, FL 32751

      0 Lake Howell Rd Unit MFRO6116578, Maitland, FL 32751

      Last Sold Summary

      • 6 Days On Market

  • /42

    $1,125,000

    • 4 Beds
    • 4 Baths
    • 3,314 Sq Ft

    1911 Belford Ct, Maitland, FL 32751

    This elegant Mediterranean-inspired one-story residence is in the gated community of Maitland Club overlooking a tranquil pond. A well maintained 4 bedroom, 4 bath Plus home office with recent updates that include a new roof, hot water heater, pool heater, and a re-pipe. The home features a soft neutral interior palette throughout with an elegant formal living room filled with natural light

    Anne Rogers ANNE ROGERS REALTY GROUP INC

    1911 Belford Ct, Maitland, FL 32751
  • /29

    $2,350 Per Month

    • 4 Beds
    • 2 Baths
    • 1,372 Sq Ft
    • Condo for Rent

    1175 Lake Shadow Cir Unit 4208, Maitland, FL 32751

    Stunning - fully remodeled 4 bed waterfront condo in resort style community of Visconti.Condo features all new vinyl plank flooring throughout, designer paint, a gourmet kitchen with brand new espresso cabinets, granite counters and stainless steel appliances.New bathrooms with custom tile, vanities and light fixtures. Screened in patio with outside storage overlooking the pond. Community offers

    Andreas Kunert KUNERT REALTY INC

    1175 Lake Shadow Cir Unit 4208, Maitland, FL 32751
  • /2

    $315,000

    Sold Feb 20, 2026

    1000 Winderley Place Unit 142, Maitland, FL 32751

    • 3 Beds
    • 2 Baths
    • 1,538 Sq Ft
    • Built 1982

    Last Sold Summary

    • 2% Below List Price
    • $205/SF
    • 23 Days On Market

    Current Estimated Value $314,326

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

    1000 Winderley Place Unit 142, Maitland, FL 32751
    • /19

      Est $417,535

      Not Listed For Sale

      517 W Faith Terrace, Maitland, FL 32751

      • 4 Beds
      • 2 Baths
      • 1,540 Sq Ft
      • Built 1963
      517 W Faith Terrace, Maitland, FL 32751

      Last Sold Summary

      • 47 Days On Market

  • /39

    $649,000

    • 2 Beds
    • 2 Baths
    • 1,125 Sq Ft

    1100 S Orlando Ave Unit 306, Maitland, FL 32751

    TURN KEY AND RENOVATED IN SOUGHT-AFTER WEST COVE!! Wake up to breathtaking sunrises with a stunning, unobstructed view stretching across Lake Maitland—the largest lake in the highly sought-after Winter Park Chain of Lakes—from this beautifully renovated, truly turnkey condominium. All flooring, bathrooms, fixtures, paint, AC, water heater, sliding door to balcony, kitchen/appliances, and closet

    Frank Benevento COLDWELL BANKER REALTY

    1100 S Orlando Ave Unit 306, Maitland, FL 32751
  • /2

    $1,999 Per Month

    • 2 Beds
    • 1 Bath
    • 1,407 Sq Ft
    • House for Rent

    620 Central Ave, Maitland, FL 32751

    AVAILABLE MID JULY-SHOWING AVAIL AFTER 6/30Charming Maitland pool home with 1 car garage and large open pool with fenced in back yard. This home is in a lovely neighborhood close to Lake Lilly & Sun Rail depot with many upgraded & newer homes. The lovely home is full of character, all flooring is wood laminate or tile, no carpet!! The kitchen overlooks an enclosed sunroom/bonus room

    620 Central Ave, Maitland, FL 32751
  • /2

    $395,000

    Sold Nov 20, 2025

    637 Magnolia Dr, Maitland, FL 32751

    • 3 Beds
    • 2 Baths
    • 1,851 Sq Ft
    • Built 1968

    Last Sold Summary

    • 18% Below List Price
    • $213/SF
    • 89 Days On Market

    Current Estimated Value $420,632

    Last Listing Agent Dione Collier-Larkin ADAIR REALTY INC

    637 Magnolia Dr, Maitland, FL 32751
    • /44

      Est $140,605

      Not Listed For Sale

      2407 Branch Way Unit 101, Maitland, FL 32751

      • 2 Beds
      • 1 Bath
      • 1,051 Sq Ft
      • Built 1973
      2407 Branch Way Unit 101, Maitland, FL 32751

      Last Sold Summary

      • 5 Days On Market

  • /30

    $629,000

    • 5 Beds
    • 2 Baths
    • 2,360 Sq Ft

    2642 Brookside Ct, Maitland, FL 32751

    Indulge in the epitome of modern living with this fully renovated masterpiece! Boasting a thoughtfully designed split floor plan, 5 bedrooms, and 2 bathrooms, this home offers the perfect blend of space, style, and versatility. The heart of the home, the sleek kitchen, is a culinary haven equipped with stainless steel appliances, and ample counter space with upscale quartz countertops and

    Giancarlo Chavez EMPIRE NETWORK REALTY

    2642 Brookside Ct, Maitland, FL 32751
  • /8

    $119,900 Per Month

    • Property for Rent

    0 Ridgewood Ave, Maitland, FL 32751

    Vacant parcel likely and ideally suitable for RV, Boat and other residential storage uses. Recorded 14' access easement to Ridgewood Avenue. Partially fenced parcel. Sign on property visible from Ridgewood Avenue. MOTIVATED SELLER WILL PROVIDE FINANCING TO QUALIFIED BUYER. LOW TAXES (Legal Description to be revised to reflect recent sale.)

    Michael Dabby DABBY REAL ESTATE ADVISORS, LLC

    0 Ridgewood Ave, Maitland, FL 32751
  • /2

    $600,000

    Sold Nov 10, 2025

    107 Tangelo Ct, Maitland, FL 32751

    • 3 Beds
    • 3 Baths
    • 1,820 Sq Ft
    • Built 1956

    Last Sold Summary

    • 9% Above List Price
    • $330/SF
    • 4 Days On Market

    Current Estimated Value $607,696

    Last Listing Agent Beth Logullo KELLER WILLIAMS WINTER PARK

    107 Tangelo Ct, Maitland, FL 32751
    • /11

      Not Listed For Sale

      2520 Caper Ln Unit 102, Maitland, FL 32751

      • 1 Bed
      • 1 Bath
      • 759 Sq Ft
      • Built 1973
      2520 Caper Ln Unit 102, Maitland, FL 32751

      Last Sold Summary

      • 56 Days On Market

  • /52

    $534,900

    $54K PRICE DROP Pending
    • 5 Beds
    • 3 Baths
    • 2,592 Sq Ft

    778 Lake Howell Rd, Maitland, FL 32751

    This stunning 5 bedroom, 3 bath home in Maitland, FL has been professionally staged to show off all its amazing upgrades. From a brand new roof to luxury vinyl planking and carpet, a kitchen cabinet with an island on wheels, granite counters, sink, and faucet, stainless steel appliances, HVAC and mini-split, interior and exterior paint, vanities for all 3 bathrooms, 5 ceiling fans, and a

    Ronald Gentile ORLANDO REO PROF I INC

    778 Lake Howell Rd, Maitland, FL 32751
  • /24

    $1,765 Per Month

    • 2 Beds
    • 2 Baths
    • 1,206 Sq Ft
    • Condo for Rent

    408 Banyon Tree Cir Unit 100, Maitland, FL 32751

    ***TENANT OCCUPIED, PLEASE SCHEDULE SHOWING***Welcome home to Carrington Park. This 2BD/2BTH freshly updated 1,206 sqft condo is now available for rent. Amenities Include 3 Pools, Fitness, and playgrounds. The entrance to your new home is through the doors and into a tiled foyer. Follow the stairs down to the first floor. Open the door and see a freshly painted unit featuring SS

    408 Banyon Tree Cir Unit 100, Maitland, FL 32751
  • /2

    $500,000

    Sold Dec 16, 2025

    113 Gem Lake Dr, Maitland, FL 32751

    • 3 Beds
    • 2 Baths
    • 1,538 Sq Ft
    • Built 1939

    Last Sold Summary

    • 13% Below List Price
    • $325/SF
    • 642 Days On Market

    Current Estimated Value $503,164

    Last Listing Agent Darryl Donkel HOME WISE REALTY GROUP, INC.

    113 Gem Lake Dr, Maitland, FL 32751
    • /17

      Est $180,701

      Not Listed For Sale

      329 Cherrywood Gardens Dr Unit 329, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 905 Sq Ft
      • Built 1974
      329 Cherrywood Gardens Dr Unit 329, Maitland, FL 32751

      Last Sold Summary

      • 27 Days On Market

  • /22

    $115,000

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft

    2422 Branch Way Unit 100, Maitland, FL 32751

    Great opportunity to own this 1-bedroom, 1-bathroom first-floor unit in a desirable and well-maintained community! This property offers a comfortable and functional layout with easy first-floor access, perfect for both homeowners and investors alike. Currently tenant-occupied with a lease in place through June 30, 2026, providing immediate rental income with future flexibility for personal use.

    Moses Nae MIAMI TANGO INVESTMENTS REALTY

    2422 Branch Way Unit 100, Maitland, FL 32751
  • /24

    $2,149 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,201 Sq Ft
    • Townhouse for Rent

    916 Robinhood Ct, Maitland, FL 32751

    Welcome home! This 3-bedroom, 1.5-bath DUPLEX is available for June 10th 2026. Includes a fenced-in backyard. Located conveniently in the desirable City of Maitland, this property is close to the shopping district, Hospital district, Winter Park shopping, and I-4. This property features a comfortable layout with well-apportioned bedrooms and bathrooms. Washer and dryer included. Act now! This one

    Steve Simpson 407 PROPERTIES

    916 Robinhood Ct, Maitland, FL 32751
  • /2

    $364,000

    Sold Jun 23, 2026

    1321 Benevolent St, Maitland, FL 32751

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

    Last Sold Summary

    • 8% Below List Price
    • $208/SF
    • 97 Days On Market

    Current Estimated Value $369,107

    Last Listing Agent Shirley Jones COLDWELL BANKER REALTY

    1321 Benevolent St, Maitland, FL 32751
    • /30

      Not Listed For Sale

      0 S Lake Destiny Rd Unit O6003665, Maitland, FL 32751

      0 S Lake Destiny Rd Unit O6003665, Maitland, FL 32751

      Last Sold Summary

      • 406 Days On Market

Showing Results 241 - 280, Page 7 of 18

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