9,992

Maitland, FL Homes

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  • /37

    $225,000

    Open Sun 12PM - 3PM $10K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,353 Sq Ft

    892 Park Lake Cir Unit 69, Maitland, FL 32751

    Maitland's Hidden Gem! Discover comfort, style, and convenience in this BEAUTIFULLY MAINTAINED 2-bedroom, 1.5-bath condo in the desirable Park Lake Townhouses community of Maitland with NEW A/C 2026 and NEW Water Heater 2026. Located minutes from Park Ave, Trader Joes, Lifetime Fitness and all Winter Park/Maitland has to offer! Offering the FEEL OF A TOWNHOME with two spacious levels, a private

    Jennifer Wemert WEMERT GROUP REALTY LLC

    892 Park Lake Cir Unit 69, Maitland, FL 32751
  • /25

    $1,999 Per Month

    • 2 Beds
    • 1 Bath
    • 1,174 Sq Ft
    • Townhouse for Rent

    914 Robinhood Ct, Maitland, FL 32751

    Welcome home! This 2-bedroom, 1-bath DUPLEX is available for Jun 9th 2026. This property has been renovated from top to bottom and includes a new 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

    914 Robinhood Ct, Maitland, FL 32751
  • /2

    $178,900

    Sold Nov 26, 2025

    107 Cherrywood Gardens Dr Unit 8, Maitland, FL 32751

    • 2 Beds
    • 1.5 Baths
    • 953 Sq Ft
    • Built 1974

    Last Sold Summary

    • 2% Above List Price
    • $188/SF
    • 5 Days On Market

    Last Listing Agent Francis Zipeto KELLER WILLIAMS CLASSIC

    107 Cherrywood Gardens Dr Unit 8, Maitland, FL 32751
    • /2

      Est $428,182

      Not Listed For Sale

      504 W Faith Terrace, Maitland, FL 32751

      • 3 Beds
      • 2 Baths
      • 1,411 Sq Ft
      • Built 1957
      504 W Faith Terrace, Maitland, FL 32751

      Last Sold Summary

      • 7 Days On Market

  • /36

    $699,000

    $26K PRICE DROP Pending
    • 4 Beds
    • 2.5 Baths
    • 2,257 Sq Ft

    151 White Oak Cir, Maitland, FL 32751

    Under contract-accepting backup offers. Offering endless possibilities in the highly sought-after Maitland Grove neighborhood, this spacious 4-bedroom, 2.5-bath pool home offers the perfect opportunity to create something truly special. Major improvements are already in place, including a newer roof (2023), A/C (2021), updated electrical panel (2026), also appears to have been replumbed,

    Mary Colton FANNIE HILLMAN & ASSOCIATES

    151 White Oak Cir, Maitland, FL 32751
  • /20

    $2,750 Per Month

    • 4 Beds
    • 2 Baths
    • 1,934 Sq Ft
    • House for Rent

    719 Kewannee Trail, Maitland, FL 32751

    Virtually Staged. Highly Sought-After Dommerich Hills Gem | 4 Bedrooms in Top-Rated Winter Park School District!Marketing DescriptionWelcome to this rare opportunity to rent a beautifully updated 4-bedroom, 2-bath home in the highly desirable Dommerich Hills community of Maitland, located within the prestigious A-rated Winter Park school district. Just a short stroll from Dommerich Elementary

    Jacob Hara TRANSCEND REALTY

    719 Kewannee Trail, Maitland, FL 32751
  • /2

    $361,200

    Sold Oct 31, 2025

    2570 Derbyshire Rd, Maitland, FL 32751

    • 4 Beds
    • 3 Baths
    • 1,857 Sq Ft
    • Built 1964

    Last Sold Summary

    • 16% Below List Price
    • $195/SF
    • 19 Days On Market

    Current Estimated Value $522,575

    Last Listing Agent Richard Traynor FLORIDA ONE REAL ESTATE LLC

    2570 Derbyshire Rd, Maitland, FL 32751
    • /18

      Est $222,035

      Not Listed For Sale

      416 Banyon Tree Cir Unit 108, Maitland, FL 32751

      • 3 Beds
      • 2 Baths
      • 1,406 Sq Ft
      • Built 1973
      416 Banyon Tree Cir Unit 108, Maitland, FL 32751

      Last Sold Summary

      • 10 Days On Market

  • /48

    $715,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,245 Sq Ft

    2450 Derbyshire Rd, Maitland, FL 32751

    Under contract-accepting backup offers. Located in the highly desirable English Estates community, this beautifully renovated home blends modern updates with comfortable Florida living. Thoughtfully redesigned throughout, the home offers four spacious bedrooms and updated bathrooms, including a private primary suite featuring a spa-inspired bath and a custom walk-in closet with built-in shelving

    Kyle Grafton FANNIE HILLMAN & ASSOCIATES

    2450 Derbyshire Rd, Maitland, FL 32751
  • /36

    $2,200 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,160 Sq Ft
    • Townhouse for Rent

    911 Robinhood Ct, Maitland, FL 32751

    Come view this fully refurbished 3 bed/1.5 bath home featuring all-new flooring, updated fixtures, and renovated bathrooms. Conveniently located near Maitland's shopping district, Winter Park, I-4, and more, this home is just two blocks from the SunRail station and only an 8-minute train ride to downtown and the hospital district. Inside, you'll find vaulted ceilings, spacious bedrooms,

    911 Robinhood Ct, Maitland, FL 32751
  • /2

    $305,000

    Sold Jul 15, 2025

    1000 Winderley Place Unit 143, Maitland, FL 32751

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

    Last Sold Summary

    • 6% Below List Price
    • $198/SF
    • 135 Days On Market

    Current Estimated Value $309,474

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

    1000 Winderley Place Unit 143, Maitland, FL 32751
    • /30

      Est $277,692

      Not Listed For Sale

      291 W Lake Faith Dr Unit 142, Maitland, FL 32751

      • 2 Beds
      • 2.5 Baths
      • 1,456 Sq Ft
      • Built 1974
      291 W Lake Faith Dr Unit 142, Maitland, FL 32751

      Last Sold Summary

      • 59 Days On Market

  • /100

    $12,500,000

    • 6 Beds
    • 10 Baths
    • 10,172 Sq Ft

    570 Manor Rd, Maitland, FL 32751

    Lakefront estate featuring 6 bed, 7 full and 3 half baths. over 11,000 SqFt on 2,7 acres. Resort-style pool, summer kitchen, 6-car garage, fully fenced with a private gate. 120 feet of lake front on Winter Park Chain of Lakes, private boat dock, and boat lift. All bedrooms with en-suite bathrooms, fireplace, sauna, fitness room, office room, and expansive walk-in closets. Lutron system, crystal

    Maggie Walas Fortune Christie's International Real Estate

    570 Manor Rd, Maitland, FL 32751
  • /14

    $1,049 Per Month

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

    2517 Caper Ln Unit 205, Maitland, FL 32751

    **GREAT LOCATION**CLOSE TO EVERYTHING** Cozy one Bedroom 2nd floor with no upstairs neighbors and pool view. New laminate floors and granite countertop. The mailbox, laundry room and pool are only few steps away. Water, sewer & Trash included in rent.Walking distance to Publix, Starbucks and many other stores (Casselberry Commons Plaza). It is also just a 10 min drive to Full Sail University and

    MAYOLET BORNAS MAYOLET REALTY LLC

    2517 Caper Ln Unit 205, Maitland, FL 32751
  • /2

    $650,000

    Sold Jun 30, 2025

    1055 Thunder Trail, Maitland, FL 32751

    • 4 Beds
    • 2.5 Baths
    • 2,351 Sq Ft
    • Built 1968

    Last Sold Summary

    • $276/SF

    Current Estimated Value $683,912

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

    1055 Thunder Trail, Maitland, FL 32751
    • /22

      Not Listed For Sale

      1140 S Orlando Ave Unit 1, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 816 Sq Ft
      • Built 1969
      1140 S Orlando Ave Unit 1, Maitland, FL 32751

      Last Sold Summary

      • 16 Days On Market

  • /47

    $1,995,000

    • 4 Beds
    • 3.5 Baths
    • 3,005 Sq Ft

    220 Adams Dr, Maitland, FL 32751

    Welcome to 220 Adams Drive — a breathtaking, completely remodeled single-story masterpiece nestled in the heart of Maitland's coveted Kings Row neighborhood. Thoughtfully reimagined from the studs out with exquisite craftsmanship and elevated design, this stunning home offers 4 bedrooms, a dedicated private office, 3.5 baths, and over 3,000 square feet of refined living on a fully fenced,

    Kelly Price KELLY PRICE & COMPANY LLC

    220 Adams Dr, Maitland, FL 32751
  • /22

    $3,995 Per Month

    • 4 Beds
    • 2 Baths
    • 1,961 Sq Ft
    • House for Rent

    2430 Deloraine Trail, Maitland, FL 32751

    Live in this beautiful 4/2 pool home in the Dommerich area! Pool and lawn care are included! Enjoy the formal living and dining room with all appliances and washer/dryer. This home has wood floors and tile throughout! Great Location next to top rated schools, Dommerich Elementary, Maitland Middle, and Winter Park High! Also close to Maitland Community Parks! *Bonus Amenity Included* -All

    2430 Deloraine Trail, Maitland, FL 32751
  • /2

    $740,000

    Sold Jul 18, 2025

    986 Stonewood Ln, Maitland, FL 32751

    • 4 Beds
    • 2.5 Baths
    • 2,195 Sq Ft
    • Built 1978

    Last Sold Summary

    • 5% Below List Price
    • $337/SF
    • 30 Days On Market

    Current Estimated Value $729,968

    Last Listing Agent Steven Luppert COMPASS FLORIDA LLC

    986 Stonewood Ln, Maitland, FL 32751
    • /21

      Est $190,384

      Not Listed For Sale

      428 Banyon Tree Cir Unit 102, Maitland, FL 32751

      • 3 Beds
      • 2 Baths
      • 1,612 Sq Ft
      • Built 1973
      428 Banyon Tree Cir Unit 102, Maitland, FL 32751

      Last Sold Summary

      • 186 Days On Market

  • /43

    $999,000

    $340K PRICE DROP Pending
    • 4 Beds
    • 3 Baths
    • 2,292 Sq Ft

    67 Cypress Ln, Maitland, FL 32751

    Under contract-accepting backup offers. Welcome to 67 Cypress Lane, a stunning single-owner custom residence nestled among majestic Cypress and Oak trees across from Lake Maitland in one of the area's most coveted neighborhoods. This architectural gem, expertly crafted from Western Red Cedar, offers two stories of thoughtfully designed living space with 4 bedrooms and 3 full baths.Step inside

    Kelly Price KELLY PRICE & COMPANY LLC

    67 Cypress Ln, Maitland, FL 32751
  • /19

    $3,450 Per Month

    • 4 Beds
    • 2 Baths
    • 1,662 Sq Ft
    • House for Rent

    738 Lake Howell Rd, Maitland, FL 32751

    Fully furnished, beautifully maintained 4 bedroom. 2 bathroom pool home with flexible lease terms of 6 months or longer. Available July 1, 2026! Inside, you’ll find an open and inviting layout featuring no carpet throughout, making for easy maintenance and a clean, modern feel. The kitchen is equipped with stainless steel appliances, granite countertops, and ample cabinet space, perfect for

    Kevin Asenjo COLDWELL BANKER REALTY

    738 Lake Howell Rd, Maitland, FL 32751
  • /2

    $507,500

    Sold Dec 04, 2025

    702 Green Meadow Ave, Maitland, FL 32751

    • 4 Beds
    • 2.5 Baths
    • 2,621 Sq Ft
    • Built 1969

    Last Sold Summary

    • 17% Below List Price
    • $194/SF
    • 181 Days On Market

    Current Estimated Value $538,669

    Last Listing Agent Cheryl Geluso RE/MAX ASSURED

    702 Green Meadow Ave, Maitland, FL 32751
    • /2

      Est $129,815

      Not Listed For Sale

      440 Banyon Tree Cir Unit 102, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 1,206 Sq Ft
      • Built 1973
      440 Banyon Tree Cir Unit 102, Maitland, FL 32751

      Last Sold Summary

      • 215 Days On Market

  • /32

    $229,500

    $6K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 612 Sq Ft

    1140 S Orlando Ave Unit E2, Maitland, FL 32751

    Live the lake lifestyle in this beautifully updated 1-bedroom condo located in the iconic mid-century modern community of Lake Maitland Terrace. Completely refreshed in 2025, this first-floor residence features a brand-new HVAC system, new appliances including washer, dryer, and kitchen disposal, updated kitchen countertops, and new flooring throughout the living areas. Freshly painted and

    Beatrice Miranda METRO CITY REALTY

    1140 S Orlando Ave Unit E2, Maitland, FL 32751
  • /18

    $1,550 Per Month

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

    1440 Lake Shadow Cir Unit 8304, Maitland, FL 32751

    Beautiful 2-bedroom, 2-bathroom condo located in the highly sought-after, gated community of Visconti in Maitland. This bright and airy floor plan offers an exceptionally open layout designed to maximize natural light throughout. The kitchen overlooks a spacious living and dining area, creating a seamless flow that is perfect for both everyday living and entertaining. Step outside to your private

    Carissa Lawhun FLORIDA REALTY INVESTMENTS

    1440 Lake Shadow Cir Unit 8304, Maitland, FL 32751
  • /2

    $150,000

    Sold Oct 24, 2025

    1125 Lake Shadow Cir Unit 5305, Maitland, FL 32751

    • 1 Bed
    • 1 Bath
    • 672 Sq Ft
    • Built 2000

    Last Sold Summary

    • 6% Below List Price
    • $223/SF
    • 32 Days On Market

    Current Estimated Value $152,192

    Last Listing Agent Shelby Kirsch REAL PROPERTY MANAGEMENT AND REALTY

    1125 Lake Shadow Cir Unit 5305, Maitland, FL 32751
    • /40

      Est $779,768

      Not Listed For Sale

      21 Minnehaha Cir, Maitland, FL 32751

      • 5 Beds
      • 2 Baths
      • 2,371 Sq Ft
      • Built 1961
      21 Minnehaha Cir, Maitland, FL 32751

      Last Sold Summary

      • 41 Days On Market

  • /37

    $3,895,000

    Pending
    • 4 Beds
    • 4.5 Baths
    • 5,347 Sq Ft

    747 N Lake Sybelia Dr, Maitland, FL 32751

    Under contract-accepting backup offers. Welcome to 747 N Lake Sybelia Drive, an extraordinary lakefront estate gracefully positioned along the desired northern shoreline of beautiful Lake Sybelia. Completed in late 2023, this breathtaking California Coastal-inspired residence spans 4,755 square feet on an expansive 0.76-acre homesite, blending timeless architecture with refined finishes to create

    Mick Night PREMIER SOTHEBY'S INTL. REALTY

    747 N Lake Sybelia Dr, Maitland, FL 32751
  • /7

    $1,099 Per Month

    • 1 Bed
    • 1 Bath
    • 540 Sq Ft
    • House for Rent

    301 Clark St, Maitland, FL 32751

    Charming and private 1-bedroom, 1-bath rental located in the heart of Maitland. This well maintained unit features a comfortable living space, a functional kitchen equipped with a stove and microwave, and a cozy layout designed for easy living. One of the best features of this rental is that water and electricity are included in the monthly rent, offering added convenience and predictable monthly

    Laury Cruz Penalo De Gomez MY REALTY GROUP, LLC.

    301 Clark St, Maitland, FL 32751
  • /2

    $380,000

    Sold Sep 17, 2025

    2041 Warrens Ave, Maitland, FL 32751

    • 3 Beds
    • 2.5 Baths
    • 1,549 Sq Ft
    • Built 2025

    Last Sold Summary

    • 10% Below List Price
    • $245/SF
    • 101 Days On Market

    Current Estimated Value $384,715

    Last Listing Agent Marcela Fischer PRISTINE INTERNATIONAL REALTY LLC

    2041 Warrens Ave, Maitland, FL 32751
    • /52

      Not Listed For Sale

      3102 Legacy Lake Dr, Maitland, FL 32751

      • 4 Beds
      • 2 Baths
      • 1,707 Sq Ft
      • Built 2000
      3102 Legacy Lake Dr, Maitland, FL 32751

      Last Sold Summary

      • 76 Days On Market

  • /51

    $321,406

    $4K PRICE INCREASE Pending
    • 2 Beds
    • 2 Baths
    • 1,403 Sq Ft

    377 W Lake Faith Dr Unit 104, Maitland, FL 32751

    Under contract-accepting backup offers. Lake Faith is a quiet community with picturesque views and beautiful landscaping a true retreat to call your own. This 2 bedroom 2 bathroom condo has been completely renovated and is turn key ready for you. The white-oak look luxury vinyl plank flooring runs throughout the space. The Kitchen overlooks the family room providing a open concept and a beautiful

    Randy Fontanez, II CHARLES RUTENBERG REALTY ORLANDO

    377 W Lake Faith Dr Unit 104, Maitland, FL 32751
  • /10

    $1,850 Per Month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Townhouse for Rent

    250 Cedarwood Dr, Maitland, FL 32751

    Spacious one-story DUPLEX - 2 bedroom, 2 bath - located on a quiet cul-de-sac in Maitland. Exterior painted last year, but all photo's do not reflect the new blue/grey paint color. This clean and well-maintained unit features tile flooring throughout the main living areas, carpet in the bedrooms, a separate dining room, inside laundry room, and an additional bonus room or enclosed porch that

    Debbie Lombardi Lemay SANDRONI HOLDINGS REAL ESTATE LLC

    250 Cedarwood Dr, Maitland, FL 32751
  • /2

    $450,000

    Sold Mar 06, 2026

    736 Forest Glen Ct, Maitland, FL 32751

    • 4 Beds
    • 2 Baths
    • 1,647 Sq Ft
    • Built 1973

    Last Sold Summary

    • 14% Below List Price
    • $273/SF
    • 188 Days On Market

    Current Estimated Value $463,958

    Last Listing Agent Dominick Florio RE/MAX TOWN & COUNTRY REALTY

    736 Forest Glen Ct, Maitland, FL 32751
    • /18

      Est $241,288

      Not Listed For Sale

      1140 S Orlando Ave Unit I16, Maitland, FL 32751

      • 2 Beds
      • 1.5 Baths
      • 816 Sq Ft
      • Built 1971
      1140 S Orlando Ave Unit I16, Maitland, FL 32751

      Last Sold Summary

      • 70 Days On Market

  • /32

    $624,990

    $20K PRICE INCREASE
    • 4 Beds
    • 3 Baths
    • 3,308 Sq Ft

    448 Stonewood Ln, Maitland, FL 32751

    One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4-bedroom, 3-bathroom pool home offering the perfect blend of space, style, and location! From the moment you walk in, you’ll love the open layout and rich hardwood floors that create a warm and inviting atmosphere throughout. Designed for both everyday living and entertaining, this home features a dedicated

    Dominick Florio RE/MAX TOWN & COUNTRY REALTY

    448 Stonewood Ln, Maitland, FL 32751
  • /10

    $2,050 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,565 Sq Ft
    • Townhouse for Rent

    1135 Grove St Unit 146, Maitland, FL 32751

    Welcome home to this two-story corner-unit townhome, offering both privacy and convenience just minutes from I-4. This residence features 3 bedrooms and 2.5 bathrooms with a comfortable and functional layout designed. The main level includes open living and dining areas and kitchen. A conveniently located first-floor laundry room. Upstairs, primary suite stands out with its own private balcony

    Johany Utrera AVID REALTY LLC

    1135 Grove St Unit 146, Maitland, FL 32751
  • /2

    $552,000

    Sold Jan 07, 2026

    1135 Thunder Trail, Maitland, FL 32751

    • 4 Beds
    • 4 Baths
    • 2,651 Sq Ft
    • Built 1967

    Last Sold Summary

    • 20% Below List Price
    • $208/SF
    • 75 Days On Market

    Current Estimated Value $747,340

    Last Listing Agent Brian Rotenberger COMPASS FLORIDA LLC

    1135 Thunder Trail, Maitland, FL 32751
    • /2

      Est $304,487

      Not Listed For Sale

      1140 S Orlando Ave Unit D1, Maitland, FL 32751

      • 2 Beds
      • 1 Bath
      • 816 Sq Ft
      • Built 1964
      1140 S Orlando Ave Unit D1, Maitland, FL 32751

      Last Sold Summary

      • 47 Days On Market

Showing Results 281 - 320, Page 8 of 18

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