9,826

Maitland, FL Homes

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  • /30

    $389,000

    $26K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,103 Sq Ft

    1994 Kenaston Rd Unit 1994, Maitland, FL 32751

    Located in the desirable city of Maitland, just three miles from Winter Park’s renowned Park Avenue, this extensively updated 3-bedroom, 3.5-bath townhouse offers modern living in a prime Central Florida location. Tucked within a quiet residential setting and zoned for highly rated Seminole County schools, the home provides easy access to dining, shopping, and entertainment while maintaining a

    Veronica Figueroa EXP REALTY LLC

    1994 Kenaston Rd Unit 1994, Maitland, FL 32751
  • /26

    $2,900 Per Month

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

    204 Quayside Cir, 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

    204 Quayside Cir, 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 $1,168,116

    Last Listing Agent Kyle Grafton FANNIE HILLMAN & ASSOCIATES

    1750 Cheyenne Trail, Maitland, FL 32751
    • /51

      Est $274,205

      Not Listed For Sale

      903 Town Cir Unit 194, Maitland, FL 32751

      • 3 Beds
      • 2.5 Baths
      • 1,565 Sq Ft
      • Built 1979
      903 Town Cir Unit 194, Maitland, FL 32751

      Last Sold Summary

      • 105 Days On Market

      Last Listing Agent Reeta Gulati RE REALTY

  • /36

    $850,000

    $145K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,459 Sq Ft

    219 Quayside Cir, Maitland, FL 32751

    Every so often, a property comes along that redefines what lake living can be, and this is that home. Thoughtfully reimagined from top to bottom, this two-bedroom, two-and-a-half-bath residence blends refined design with the effortless lifestyle of the Winter Park Chain of Lakes. Go inside to discover a fully renovated interior anchored by a showstopping 14-foot Cambria quartz waterfall island,

    Chad Isenhart PREMIER SOTHEBY'S INTL. REALTY

    219 Quayside Cir, Maitland, FL 32751
  • /24

    $1,795 Per Month

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    3011 Legacy Villas Dr Unit 3011, Maitland, FL 32751

    Impressive - nicely updated 3 story - 2 bed + DenTownhome with 2 car garage in resort style community of Visconti. Featuring designer paint, contemporary plush carpet flooring, LED light fixtures and ceiling fans. First floor with 2 car garage. Second floor offers an open concept floor plan with gourmet kitchen, granite counter tops, living / dining room combo and bonus room / den. 3rd floor

    Andreas Kunert KUNERT REALTY INC

    3011 Legacy Villas Dr Unit 3011, Maitland, FL 32751
  • /2

    $113,000

    Sold Aug 10, 2026

    550 Flemming Way Unit 100, Maitland, FL 32751

    • 2 Beds
    • 1 Bath
    • 1,051 Sq Ft
    • Built 1973

    Last Sold Summary

    • 19% Below List Price
    • $108/SF
    • 34 Days On Market

    Current Estimated Value $139,870

    Last Listing Agent Brandy Ray LOKATION

    550 Flemming Way Unit 100, Maitland, FL 32751
    • /29

      Est $380,122

      Not Listed For Sale

      1840 Rogers Ave, Maitland, FL 32751

      • 3 Beds
      • 2 Baths
      • 1,458 Sq Ft
      • Built 2024
      1840 Rogers Ave, Maitland, FL 32751

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Mario Zendeli COMPASS FLORIDA LLC

  • /18

    $460,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,740 Sq Ft

    315 Lake Seminary Cir, Maitland, FL 32751

    Under contract-accepting backup offers. Charming 3-bedroom, 2-bath pool home in Maitland with tons of potential! This home is ready for a buyer with the vision to renovate, restore, and make it their own. The property needs substantial TLC throughout, but offers a wonderful opportunity to customize it to your personal style. Features include a private pool, screened patio, spacious yard, and

    Lisa Thelemaque FLORIDA REALTY INVESTMENTS

    315 Lake Seminary Cir, Maitland, FL 32751
  • /24

    $1,650 Per Month

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

    408 Banyon Tree Cir Unit 100, Maitland, FL 32751

    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 appliances, ceramic tile & new woodlike vinyl plank flooring in

    408 Banyon Tree Cir Unit 100, 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 $313,400

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

    1000 Winderley Place Unit 142, Maitland, FL 32751
    • /2

      Est $526,342

      Not Listed For Sale

      229 Quayside Cir Unit C, Maitland, FL 32751

      • 3 Beds
      • 2.5 Baths
      • 1,652 Sq Ft
      • Built 1985
      229 Quayside Cir Unit C, Maitland, FL 32751

      Last Sold Summary

      • 92 Days On Market

      Last Listing Agent MaryAnne Branner PREMIER SOTHEBY'S INTL. REALTY

  • /27

    $225,000

    • 2 Beds
    • 1.5 Baths
    • 1,432 Sq Ft

    820 Park Lake Cir Unit 11, Maitland, FL 32751

    Welcome to 820 Park Lake Circle, a beautifully updated two-bedroom condo tucked into one of Maitland’s most convenient locations. Offering the charm and space of a townhouse with the ease of condominium living, this inviting home is just minutes from Downtown Maitland, Park Avenue, Winter Park Village, Lake Lily, major healthcare campuses, I-4, and some of Central Florida’s best shopping and

    Brian Rotenberger COMPASS FLORIDA LLC

    820 Park Lake Cir Unit 11, 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

    $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 $431,946

    Last Listing Agent Dione Collier-Larkin ADAIR REALTY INC

    637 Magnolia Dr, Maitland, FL 32751
    • /12

      Est $395,537

      Not Listed For Sale

      1920 Rogers Ave, Maitland, FL 32751

      • 3 Beds
      • 2 Baths
      • 1,559 Sq Ft
      • Built 2023
      1920 Rogers Ave, Maitland, FL 32751

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Keishawn Thomas KELLER WILLIAMS REALTY AT THE PARKS

  • /70

    $979,000

    • 4 Beds
    • 3 Baths
    • 2,931 Sq Ft

    1281 Wellington Terrace, Maitland, FL 32751

    Welcome to 1281 Wellington Terrace, a beautifully maintained 4-bedroom, 3-bath home offering 2,931 square feet in one of Maitland’s most desirable and established neighborhoods. With spacious interiors, thoughtful updates, and deeded access to Lake of the Woods, this home offers an exceptional combination of comfort, versatility, and location.One of the home’s most distinctive features is

    Tom Noelke NOELKE REALTY

    1281 Wellington Terrace, Maitland, FL 32751
  • /9

    $1,775 Per Month

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

    249 Orange Place Unit 249 Orange Pl, Maitland, FL 32751

    Step into comfort with this beautifully updated apartment that offers the perfect blend of modern convenience and unbeatable location. Nestled in a highly sought-after Maitland neighborhood, this home is perfect for those who love being close to the action. Enjoy convenient access to the iconic Enzian Theater, vibrant downtown Maitland, upscale shopping at Winter Park Village, and top-rated

    249 Orange Place Unit 249 Orange Pl, 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 $625,228

    Last Listing Agent Beth Logullo KELLER WILLIAMS WINTER PARK

    107 Tangelo Ct, Maitland, FL 32751
    • /65

      Est $252,426

      Not Listed For Sale

      804 Park Lake Cir Unit 3, Maitland, FL 32751

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

      Last Sold Summary

      • 52 Days On Market

      Last Listing Agent Amber Finch FINCH REAL ESTATE COMPANY

  • /26

    $500,000

    $25K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,920 Sq Ft

    2464 Hunterfield Rd, Maitland, FL 32751

    WELCOME HOME to 2464 Hunterfield Rd in English Estates! If you've been searching for a home with space, style, and an inviting layout, you've found it. This beautifully maintained 4-bedroom, 2-bath home offers the perfect blend of comfort and functionality in one of Maitland's most desirable neighborhoods.From the moment you walk in, you'll appreciate the light and bright interior,

    David Fraser KELLER WILLIAMS ADVANTAGE III

    2464 Hunterfield Rd, Maitland, FL 32751
  • /41

    $2,650 Per Month

    • 2 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Condo for Rent

    1100 S Orlando Ave Unit 601, Maitland, FL 32751

    LAKEFRONT Prepare to be impressed with this luxurious rare find in charming Maitland, Fl.when you enter this beautifully renovated two bedroom 2 bath lake frontcondominium in established West Cove Condominiums. The spacious corner unitoffers spectacular sunrise and lake views of Lake Maitland, the largest of the Winer ParkChain of Lakes. The updated kitchen with bright cabinets,

    Joann Beck BECK REALTY LLC

    1100 S Orlando Ave Unit 601, Maitland, FL 32751
  • /2

    $485,000

    Sold May 21, 2026

    1106 Charming St, Maitland, FL 32751

    • 3 Beds
    • 2.5 Baths
    • 1,870 Sq Ft
    • Built 2006

    Last Sold Summary

    • 2% Below List Price
    • $259/SF
    • 13 Days On Market

    Current Estimated Value $485,550

    Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY

    1106 Charming St, Maitland, FL 32751
    • /2

      Est $344,244

      Not Listed For Sale

      1980 Water Ln, Maitland, FL 32751

      • 3 Beds
      • 2 Baths
      • 1,265 Sq Ft
      • Built 1982
      1980 Water Ln, Maitland, FL 32751

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Moe Mossa SAVVY AVENUE, LLC

  • /33

    $739,000

    $11K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,066 Sq Ft

    1761 Tippicanoe Trail, Maitland, FL 32751

    Under contract-accepting backup offers. Situated on a quiet, tree-lined street in the highly sought after and desired Dommerich neighborhood this home is just a short walk or bike ride to DOMMERICH Elementary and Maitland Middle schools. This charming residence has been thoughtfully renovated and offers the best of old world charm and modern updates. Some of this homes many features include an

    David Francetic COLDWELL BANKER REALTY

    1761 Tippicanoe Trail, Maitland, FL 32751
  • /9

    $1,495 Per Month

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

    1100 Lake Shadow Cir, Maitland, FL 32751

    As the title states, this is a spacious 2 bedroom condo in the great community of Visconti in Maitland. Visconti is a gorgeous community centrally located and just minutes from I-4, 408, Winter Park, Altamonte Springs, downtown Orlando, RDV Sportsplex, Maitland Center Business Park, shopping, dining and entertainment. Visconti features incredible amenities including a resort style pool

    1100 Lake Shadow Cir, 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 $500,751

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

    113 Gem Lake Dr, Maitland, FL 32751
    • /2

      Est $304,916

      Not Listed For Sale

      466 Citrus Ln, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 1,182 Sq Ft
      • Built 1983
      466 Citrus Ln, Maitland, FL 32751

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Morgan Sloan SLOAN PROPERTIES INC

  • /21

    $375,000

    $80K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,270 Sq Ft

    204 Quayside Cir Unit 304, Maitland, FL 32751

    New Price!!! SELLER PAYING CONCESSIONS OF 3 MONTH HOA FEES. Something is very special about Lakefront Living! Come visit this beautiful Lakefront Condo located at The Moorings On Lake Maitland, part of the Winter Park chain of lakes. Enjoy the Florida lifestyle in a carefree home with lake front amenities. Imagine Entertaining Family & Friends at the Pool or Heated Spa and the Clubhouse of the

    Beatrice Palladino GALLERY PROPERTIES INTERNATIONAL

    204 Quayside Cir Unit 304, Maitland, FL 32751
  • /12

    $2,600 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,939 Sq Ft
    • House for Rent

    1695 E Horatio Ave, Maitland, FL 32751

    Great Location, this home is located on Community of Dommerich Estates, Maitland, Florida, Top Rated Schools, less than 1 mile to Lake Minnehaha and approximately 2.6 miles to Lake Maitland, and less than 1 mile to John Langdon Park, John Hudson Park, and Kings Row Park. House had tile throughout interior floor & ready to move in.

    Tuan Nguyen VISTA REALTY INVESTMENT

    1695 E Horatio Ave, 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 $365,953

    Last Listing Agent Shirley Jones COLDWELL BANKER REALTY

    1321 Benevolent St, Maitland, FL 32751
    • /40

      Est $242,947

      Not Listed For Sale

      608 Waverly Ln Unit 408-B, Maitland, FL 32751

      • 3 Beds
      • 3 Baths
      • 1,328 Sq Ft
      • Built 1980
      608 Waverly Ln Unit 408-B, Maitland, FL 32751

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Debbie Ellis EXP Realty LLC

  • /45

    $184,900

    $14K PRICE DROP
    • 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
  • /17

    $2,995 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,995 Sq Ft
    • House for Rent

    2330 Mohawk Trail, Maitland, FL 32751

    Nice Dommerich property. Well insulated in the heart of the community. Wonderful open kitchen with granite countertops and a very private fenced in backyard with lawn service included! Very clean 3 bedroom 2 1/2 bath, all bedrooms on same wing. This home also features a wood burning fireplace. *Bonus Amenity Included* - All residents are enrolled in the Resident Benefits Package (RBP) for

    2330 Mohawk Trail, 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
    • /31

      Est $274,634

      Not Listed For Sale

      277 W Lake Faith Dr Unit 149, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 1,403 Sq Ft
      • Built 1974
      277 W Lake Faith Dr Unit 149, Maitland, FL 32751

      Last Sold Summary

      • 46 Days On Market

      Last Listing Agent Mark Fuller EXIT BEACH REALTY

  • /71

    $469,000

    $59K PRICE DROP Under Contract
    • 4 Beds
    • 2 Baths
    • 1,909 Sq Ft

    653 Green Meadow Ave, Maitland, FL 32751

    Under contract-accepting backup offers. 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

    Deanna Chance A+ REALTY PROFESSIONALS, INC

    653 Green Meadow Ave, Maitland, FL 32751
  • /9

    $975 Per Month

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

    2517 Caper Ln, Maitland, FL 32751

    This 550 square foot condo is a studio that feels like a one bedroom! The bedroom area is separated from the living and dinning room with a open arched entry. It has a spacious walk in closet. Amenities include three pools, fitness center, and play ground. Water and sewer is included with rent. Qualification Must pass criminal and credit back ground check show verifiable income. Great price for

    2517 Caper Ln, 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 $524,817

    Last Listing Agent Richard Traynor FLORIDA ONE REAL ESTATE LLC

    2570 Derbyshire Rd, Maitland, FL 32751
    • /38

      Est $261,120

      Not Listed For Sale

      235 W Lake Faith Dr Unit 212, Maitland, FL 32751

      • 2 Beds
      • 2 Baths
      • 1,403 Sq Ft
      • Built 1974
      235 W Lake Faith Dr Unit 212, Maitland, FL 32751

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent Amanda Binns STRICKLAND REALTY GROUP INC

Showing Results 241 - 280, Page 7 of 18

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