9,826

Maitland, FL Homes

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  • /37

    $549,000

    Under Contract
    • 4 Beds
    • 2 Baths
    • 2,015 Sq Ft

    564 Brookside Cir, Maitland, FL 32751

    Under contract-accepting backup offers. Virtually Staged. Welcome home to this spacious 4-bedroom, 2-bath pool home in Maitland. From the moment you arrive, you'll appreciate the attractive brick exterior and inviting curb appeal. Inside, a welcoming foyer is flanked by a large formal living room with parquet flooring and abundant natural light, while the formal dining room features classic

    Maria Van Warner FANNIE HILLMAN & ASSOCIATES

    564 Brookside Cir, Maitland, FL 32751
  • /23

    $1,495 Per Month

    • 2 Beds
    • 1 Bath
    • 898 Sq Ft
    • Condo for Rent

    1375 Lake Shadow Cir Unit 11304, Maitland, FL 32751

    This beautiful two-bedroom, one bath 898 sqft condo is located in the gated community of Visconti in Maitland. Located on the third floor, the condominium features volume ceilings in the living areas for an open and expansive feeling with the living room opening to a screened in patio through the oversized sliding glass doors. The kitchen overlooks the living and dining rooms and contains a full

    1375 Lake Shadow Cir Unit 11304, Maitland, FL 32751
  • /2

    $650,000

    Sold Feb 13, 2026

    1100 Willowbrook Trail, Maitland, FL 32751

    • 4 Beds
    • 3 Baths
    • 2,964 Sq Ft
    • Built 1966

    Last Sold Summary

    • 23% Below List Price
    • $219/SF
    • 103 Days On Market

    Current Estimated Value $687,720

    Last Listing Agent Skip Kirst COLLADO REAL ESTATE

    1100 Willowbrook Trail, Maitland, FL 32751
    • /2

      Est $346,570

      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

      Last Listing Agent Mitch Mells WEICHERT REALTORS HALLMARK PROPERTIES

  • /33

    $560,000

    • 4 Beds
    • 2 Baths
    • 1,939 Sq Ft

    1540 E Horatio Ave, Maitland, FL 32751

    Welcome to Maitland living, where space and everyday convenience come together.This 3-bedroom, 2-bath home offers a surprisingly flexible floor plan with a formal living area, dining space, fireplace, open-concept kitchen and living areas, plus a separate family room and an additional flex space that could easily become a home office, playroom or 4th bedroom. Outside, a fenced backyard

    Allison Hunter LUXE HUNTER REAL ESTATE

    1540 E Horatio Ave, Maitland, FL 32751
  • /30

    $1,650 Per Month

    • 2 Beds
    • 2 Baths
    • 1,111 Sq Ft
    • Apartment for Rent

    1150 Lake Shadow Cir Unit 3102, Maitland, FL 32751

    Coming Up July 1st!!! Live the Florida Resort Life style at the Visconti Condominium. Gated community, community pool, playground, open parking.This 1st floor condo has ceramic flooring throughout, full laundry on site. Come and make this cozy condo your new home. Washer and Dryer arecomplementary appliances.

    Jose Solano FUSION FLORIDA REALTY LLC

    1150 Lake Shadow Cir Unit 3102, Maitland, FL 32751
  • /50

    $780,000

    Sold Sep 11, 2026

    791 Sequoia Trail, Maitland, FL 32751

    • 5 Beds
    • 3.5 Baths
    • 4,144 Sq Ft
    • Built 1961

    Last Sold Summary

    • 46% Below List Price
    • $188/SF
    • 322 Days On Market

    Current Estimated Value $1,031,647

    Last Listing Agent David Van Wormer VANWORMER REALTY & DEVELOPMENT

    791 Sequoia Trail, Maitland, FL 32751
    • /2

      Est $274,348

      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

      Last Listing Agent Kim North COLDWELL BANKER STEVENS RE

  • /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
  • /11

    $1,175 Per Month

    • 2 Beds
    • 1 Bath
    • 875 Sq Ft
    • Condo for Rent

    2075 Howell Branch Rd Unit 1, Maitland, FL 32751

    ***Move-In Special! Sign a lease by September 15th and receive 50% OFF your second full month's rent!*** Available Now! This charming 2-bedroom, 1-bathroom end unit in Maitland comes with large kitchen with all appliances and two spacious bedrooms with built-in closest to store all your personal items. This apartment is perfectly situated within walking distance to grocery stores, restaurants,

    2075 Howell Branch Rd Unit 1, Maitland, FL 32751
  • /2

    $255,000

    Sold Sep 29, 2025

    1140 S Orlando Ave Unit J2, Maitland, FL 32751

    • 1 Bed
    • 1 Bath
    • 816 Sq Ft
    • Built 1969

    Last Sold Summary

    • $312/SF
    • 0 Days On Market

    Current Estimated Value $251,722

    Last Listing Agent Harif Hazera LLC PREMIER SOTHEBY'S INTL. REALTY

    1140 S Orlando Ave Unit J2, 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

      Last Listing Agent Laura Napoleon KELLER WILLIAMS WINTER PARK

  • /30

    $500,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,321 Sq Ft

    7909 Chartreux Ln, Maitland, FL 32751

    Under contract-accepting backup offers. A beautifully renovated, move-in ready family home is now available in the established Winfield community in the heart of Maitland. This 4-bedroom, 3-bathroom, two-story property, set on 2,321 square feet of thoughtfully updated living space, combines fresh modern finishes with the long-term peace of mind every family deserves. Step inside to a bright, open

    Dylan Pino REALTY HUB

    7909 Chartreux Ln, Maitland, FL 32751
  • /17

    $1,650 Per Month

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

    1225 Lake Shadow Cir Unit 14106, Maitland, FL 32751

    Minutes away from the Maitland business center, I-4, Winter Park and downtown Orlando. Beautiful 2 bedroom 2 bathroom condominium in the gated community of Visconti. The first floor condominium offers community amenities include a resort style pool, fitness center, valet trash service, car wash, basketball and tennis courts.

    Matthew Angell VIDA REAL ESTATE SERVICES LLC

    1225 Lake Shadow Cir Unit 14106, Maitland, FL 32751
  • /2

    $600,000

    Sold Apr 09, 2026

    2462 Markingham Rd, Maitland, FL 32751

    • 4 Beds
    • 2 Baths
    • 2,400 Sq Ft
    • Built 1968

    Last Sold Summary

    • 4% Below List Price
    • $250/SF
    • 19 Days On Market

    Current Estimated Value $599,654

    Last Listing Agent Steven Kwong CHARLES RUTENBERG REALTY ORLANDO

    2462 Markingham Rd, Maitland, FL 32751
    • /2

      Est $231,606

      Not Listed For Sale

      818 Park Lake Cir Unit 10, Maitland, FL 32751

      • 3 Beds
      • 3 Baths
      • 1,575 Sq Ft
      • Built 1972
      818 Park Lake Cir Unit 10, Maitland, FL 32751

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

  • /2

    $108,000

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft

    559 Flemming Way Unit 203, Maitland, FL 32751

    Virtually Staged. Welcome to this well-maintained and move-in-ready second-floor condo, offering comfort, convenience, and a great location! This charming 1-bedroom, 1-bathroom unit features a spacious layout, a large walk-in closet, and a private outdoor patio where you can enjoy your morning coffee or relax after a long day. The property is currently vacant and ready to show, making it an

    Moses Nae MIAMI TANGO INVESTMENTS REALTY

    559 Flemming Way Unit 203, Maitland, FL 32751
  • /15

    $3,195 Per Month

    • 4 Beds
    • 2 Baths
    • 2,006 Sq Ft
    • House for Rent

    420 Arapaho Trail, Maitland, FL 32751

    Live in this 4 bedroom 2 bath, 2006 sqft home. This property features a 2 car garage, living room, dining room, and family room. This home also has a split floor plan with tile throughout and all appliances with washer and dryer hookups. Enjoy privacy with the fenced in back yard. Lawn care is included. This home is conveniently located just blocks from Dommerich Elementary and Maitland Middle

    420 Arapaho Trail, Maitland, FL 32751
  • /2

    $475,000

    Sold Apr 24, 2026

    1140 S Orlando Ave Unit C2, Maitland, FL 32751

    • 2 Beds
    • 2 Baths
    • 1,224 Sq Ft
    • Built 1964

    Last Sold Summary

    • 5% Below List Price
    • $388/SF
    • 15 Days On Market

    Current Estimated Value $463,836

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

    1140 S Orlando Ave Unit C2, Maitland, FL 32751
    • /2

      Est $215,324

      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

      Last Listing Agent Rebecca Hopson CHARLES RUTENBERG REALTY ORLANDO

  • /62

    $925,000

    $75K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 3,049 Sq Ft

    755 Woodside Rd, Maitland, FL 32751

    NEWLY PRICED TO SELL, UNDER APPRAISED VALUE, DO NOT MISS THIS OPPORTUNITY!! SLEEK MODERN HOME, where EVERY MAJOR SYSTEM AND FINISH has been REPLACED, REFRESHED and ELEVATED to perfection and just minutes from Winter Park. 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

    Diane Heiken EMPIRE NETWORK REALTY

    755 Woodside Rd, Maitland, FL 32751
  • /11

    $1,175 Per Month

    • 2 Beds
    • 1 Bath
    • 875 Sq Ft
    • Condo for Rent

    2075 Howell Branch Rd Unit 101, Maitland, FL 32751

    ***Move-In Special! Sign a lease by September 15th and receive 50% OFF your second full month's rent!*** Available Now! This charming 2-bedroom, 1-bathroom end unit in Maitland comes with large kitchen with all appliances and two spacious bedrooms with built-in closest to store all your personal items. This apartment is perfectly situated within walking distance to grocery stores, restaurants,

    Kevan Patel CENTRAL FLORIDA REALTY MANAGEMENT LLC

    2075 Howell Branch Rd Unit 101, Maitland, FL 32751
  • /2

    $220,000

    Sold Nov 19, 2025

    3006 Legacy Villas Dr, Maitland, FL 32751

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Built 2000

    Last Sold Summary

    • 17% Below List Price
    • $172/SF
    • 73 Days On Market

    Current Estimated Value $223,064

    Last Listing Agent Jeralia Kolb CHARLES RUTENBERG REALTY ORLANDO

    3006 Legacy Villas Dr, Maitland, FL 32751
    • /2

      Est $211,071

      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

      Last Listing Agent Kati Ettinger INNOVATIVE REALTY, LLC

  • /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
  • /24

    $1,295 Per Month

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

    1275 Lake Shadow Cir Unit 13202, Maitland, FL 32751

    Freshly painted to a nice soft gray with Sherwin Williams Paint with new kitchen, bathroom & laundry water proof floors. This condo is located on the second floor. Community offers gated community, pool, playground, fitness center, party hall, kids pool & splash, hot tub, tennis court, basketball court, walking & running trail. This condo is available for immediate move in. Please send your

    1275 Lake Shadow Cir Unit 13202, Maitland, FL 32751
  • /39

    $535,000

    Sold Apr 17, 2026

    1531 Glastonberry Rd, Maitland, FL 32751

    • 3 Beds
    • 2.5 Baths
    • 1,575 Sq Ft
    • Built 1971

    Last Sold Summary

    • 4% Below List Price
    • $340/SF
    • 18 Days On Market

    Current Estimated Value $533,361

    Last Listing Agent Brandon Frank ROUTE REAL ESTATE

    1531 Glastonberry Rd, Maitland, FL 32751
    • /40

      Est $323,000

      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

      Last Listing Agent Jean Chalifour COLDWELL BANKER REALTY

  • /29

    $250,000

    • 3 Beds
    • 2 Baths
    • 1,406 Sq Ft

    416 Banyon Tree Cir Unit 108, Maitland, FL 32751

    Move-in ready 3-bedroom, 2-bath condo in the heart of Maitland! This beautifully maintained home features an open-concept layout, abundant natural light, and ceramic tile flooring throughout. The updated kitchen offers generous cabinetry, stylish countertops, decorative backsplash, stainless steel appliances, breakfast bar, and views of the community pool. The spacious primary suite features a

    Giovanni Hernandez FORTEX REALTY INC

    416 Banyon Tree Cir Unit 108, Maitland, FL 32751
  • /10

    $1,265 Per Month

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

    385 Lime St Unit 2, Maitland, FL 32751

    Welcome home to this charming 2-bedroom, 1-bath duplex offering a spacious great room and a separate kitchen with attractive tile flooring throughout. The kitchen comes fully equipped with essential appliances making everyday living easy and convenient. Central heating and air conditioning provide year-round comfort, and lawn care is included in the rent for added peace of mind. New stove is

    David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

    385 Lime St Unit 2, 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 $554,738

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

    2021 Mohican Trail, Maitland, FL 32751
    • /22

      Est $183,264

      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

      Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  • /42

    $519,999

    $5K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,344 Sq Ft

    1776 Bobtail Dr, Maitland, FL 32751

    Welcome to 1776 Bobtail Drive, a home that offers an easy, natural flow and a layout designed for everyday living. This property is now being reintroduced with a refreshed presentation and a full 3D walkthrough experience, giving buyers the ability to explore every space at their own pace before stepping inside in person. Inside, the home features an open-concept layout where the kitchen, dining,

    Anthony Scaraggi THE FLORIDA PROPERTY SHOP SALE

    1776 Bobtail Dr, Maitland, FL 32751
  • /11

    $1,265 Per Month

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft
    • House for Rent

    385 Lime St, Maitland, FL 32751

    ***Move in Special, $500 Off First Month's Rent***Welcome home to this charming 2-bedroom, 1-bath duplex offering a spacious great room and a separate kitchen with attractive tile flooring throughout. The kitchen comes fully equipped with essential appliances making everyday living easy and convenient. Central heating and air conditioning provide year-round comfort, and lawn care is included in

    385 Lime St, 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 $511,068

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

    1220 Winston Rd, Maitland, FL 32751
    • /34

      Est $264,665

      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

      Last Listing Agent Eddie Cooper MAINFRAME REAL ESTATE

  • /25

    $90,000

    $30K PRICE DROP Pending
    • 1 Bed
    • 1 Bath
    • 658 Sq Ft

    416 Banyon Tree Cir Unit 206, Maitland, FL 32751

    Discover this beautifully maintained 1-bedroom, 1-bath condo in the highly desirable Banyan Tree Condominium of Maitland. Located on the second floor, this unit boasts abundant natural light, a functional layout, and low-maintenance living—perfect for families, first-time buyers, or savvy investors seeking rental income. Enjoy affordable HOA fees ($255.86/month) covering building insurance, pool,

    Yuleana Gil Abreu NEXUS INTERNATIONAL REALTY

    416 Banyon Tree Cir Unit 206, Maitland, FL 32751
  • /25

    $2,900 Per Month

    • 2 Beds
    • 2 Baths
    • 1,203 Sq Ft
    • Condo for Rent

    204 Quayside Cir Unit 603, Maitland, FL 32751

    COMING SOON! Experience lakefront living at its finest in this completely updated, water-facing 2-bedroom, 2-bathroom condo located in the highly sought-after Moorings community on the Winter Park Chain of Lakes! Take the elevator to the 6th-floor penthouse and enjoy spectacular views of Lake Maitland. This beautifully updated condo offers a spacious living area, a well-appointed kitchen, and

    Kevan Patel CENTRAL FLORIDA REALTY MANAGEMENT LLC

    204 Quayside Cir Unit 603, 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 $996,458

    Last Listing Agent Darein Washington KELLER WILLIAMS ADVANTAGE REALTY

    1630 Chinook Trail, Maitland, FL 32751
    • /2

      Est $167,236

      Not Listed For Sale

      1275 Lake Shadow Cir Unit 13107, Maitland, FL 32751

      • 1 Bed
      • 1 Bath
      • 672 Sq Ft
      • Built 2000
      1275 Lake Shadow Cir Unit 13107, Maitland, FL 32751

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Angel O'Brien RIGHT REALTY CONNECTION, INC.

Showing Results 201 - 240, Page 6 of 18

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