Maitland, FL Homes

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  $325,000 Pending

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

  1000 Winderley Place Unit 142, Maitland, FL 32751

  Under contract-accepting backup offers. Wake up to water views, an abundance of natural light, and tropical serenity in this beautifully appointed, private ground-floor residence.Embrace a calm, relaxing lifestyle in this light-filled, ground-floor condo surrounded by lush tropical landscaping, located in Maitland’s popular gated community of Sun Bay Club. Designed for effortless living, this

  Sandi Peery RE/MAX TOWN & COUNTRY REALTY

  1000 Winderley Place Unit 142, Maitland, FL 32751
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  /55

  $1,545 - $3,889 per month

  The Parker at Maitland Station Apartments

  1 - 3 Beds

  955 N Orlando Ave, Maitland, FL 32751

  Connect to what matters at The Parker at Maitland Station, Orlando's newest luxury apartment community. Located at the historic Parker Lumber Yard site, our Maitland, FL apartments provide easy access to the very best dining,shopping, jobs and outdoor activities Central Florida has to offer. The Parker at Maitland Station Apartments focuses on the old school friendliness while setting new

  955 N Orlando Ave, Maitland, FL 32751
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  $2,770,000 Sold Sep 11, 2025

  216 N Lake Sybelia Dr, Maitland, FL 32751

  • 5 Beds
  • 5.5 Baths
  • 4,697 Sq Ft
  • Built 2021

  Last Sold Summary

  • 4% Below List Price
  • $590/SF
  • 3 Days On Market

  Current Estimated Value $2,779,855

  Last Listing Agent Kevin Acker RE/MAX 200 REALTY

  216 N Lake Sybelia Dr, Maitland, FL 32751
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  /18

  Est $116,818 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 550 Sq Ft

  2517 Caper Ln Unit 205, Maitland, FL 32751

  2517 Caper Ln Unit 205, Maitland, FL 32751
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  $260,000

  • 2 Beds
  • 2.5 Baths
  • 1,456 Sq Ft

  335 W Lake Faith Dr Unit S, Maitland, FL 32751

  SELLER MOTIVATED. Welcome to Tranquility and Relaxation in this quiet meticulously maintained Gated Condominium Community- Lake Faith Villas. This beautiful community rests on the shores of Lake Faith in Maitland and is truly a Hidden Gem. This tastefully updated 2 bedroom 2.5 bath 2- Story END UNIT is nestled in a prime location within the community featuring an Updated Spacious Kitchen with

  Nicholas Wild GATE PROPERTIES & MANAGEMENT INC

  335 W Lake Faith Dr Unit S, Maitland, FL 32751
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  /29

  $1,875 per month

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

  2625 Legacy Villas Dr, Maitland, FL 32751

  This spacious two-bedroom, two bath 1,280 sq ft town home is located in the gated community of Visconti in Maitland. The town home features volume ceilings in the living areas for an open and expansive feeling with large windows that allow light to brighten the space. The kitchen overlooks the living and dining rooms and contains a full suite of appliances including the refrigerator, range,

  Justin Recca INNOVATIVE REALTY, LLC

  2625 Legacy Villas Dr, Maitland, FL 32751
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  /2

  $970,000 Sold Sep 04, 2025

  2031 Chippewa Trail, Maitland, FL 32751

  • 4 Beds
  • 3 Baths
  • 2,385 Sq Ft
  • Built 1961

  Last Sold Summary

  • $407/SF

  Current Estimated Value $949,387

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

  2031 Chippewa Trail, Maitland, FL 32751
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  /24

  Est $159,299 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,051 Sq Ft

  488 Banyon Tree Cir Unit 202, Maitland, FL 32751

  488 Banyon Tree Cir Unit 202, Maitland, FL 32751
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  $800,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,253 Sq Ft

  185 Birchwood Dr, Maitland, FL 32751

  Under contract-accepting backup offers. Welcome to 185 Birchwood Drive, a rare Maitland SKIABLE LAKEFRONT retreat offering the perfect combination of privacy, elevation, and effortless Florida luxury. Positioned high above the waterline with sweeping lake views, this property delivers true lake living without the typical flood insurance requirement. Inside, the home is bright and inviting with

  Chase Morton Tate COMPASS FLORIDA LLC

  185 Birchwood Dr, Maitland, FL 32751
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  $1,974 - $3,046 per month

  Maitland City Centre

  1 - 2 Beds

  160-190 Independence Ln, Maitland, FL 32751

  .custom-read-more #more {display: none;} Indulge in the upscale lifestyle you deserveour spacioushomes in the heart of Maitland have everything you need to make it happen.High-end amenities, elegant interiors, and an excellent location in the NorthOrlando area blend together to create a carefree experience. So check out our luxury apartments in Maitland, FL and find the home

  160-190 Independence Ln, Maitland, FL 32751
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  $700,000 Sold Jun 02, 2025

  1641 E Horatio Ave, Maitland, FL 32751

  • 4 Beds
  • 3 Baths
  • 2,618 Sq Ft
  • Built 1957

  Last Sold Summary

  • $267/SF
  • 22 Days On Market

  Current Estimated Value $738,818

  Last Listing Agent Erin Baker FANNIE HILLMAN & ASSOCIATES

  1641 E Horatio Ave, Maitland, FL 32751
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  /25

  Est $316,917 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft

  437 Poplar Ct, Maitland, FL 32751

  437 Poplar Ct, Maitland, FL 32751
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  $825,000

  • 3 Beds
  • 2.5 Baths
  • 2,441 Sq Ft

  312 Macarthur Place, Maitland, FL 32751

  NEW ROOF, NEWER AC, and NO HOA—this beautifully maintained home on a quiet cul-de-sac offers comfort, charm, and an unbeatable location. Nestled just steps from Lake Sybelia. This property provides a peaceful, scenic setting while still being close to all that Maitland has to offer, including popular local restaurants, shops, and community spots. A short drive takes you to the vibrant dining,

  Sean David REAL BROKER, LLC.

  312 Macarthur Place, Maitland, FL 32751
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  /21

  $1,695 per month

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

  1225 Lake Shadow Cir Unit 14305, Maitland, FL 32751

  Stunning 2 bed 2 bath condo on third floor in resort style community of Visconti. This stylish unit features designer paint, plush new carpeting, 2 master suites, LED lighting and a gourmet kitchen with direct access to laundry room with full size washer and dryer hook ups. Community offers its residents 2 swimming pools overlooking Lake Shadow, Fitness gym, Tennis - and basket ball court and

  Andreas Kunert KUNERT REALTY INC

  1225 Lake Shadow Cir Unit 14305, Maitland, FL 32751
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  /2

  $235,000 Sold Jan 29, 2026

  613 Orange Tree Ct Unit 507, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,256 Sq Ft
  • Built 1974

  Last Sold Summary

  • 3% Below List Price
  • $187/SF
  • 10 Days On Market

  Last Listing Agent Deborah Morris KELLER WILLIAMS ADVANTAGE REALTY

  613 Orange Tree Ct Unit 507, Maitland, FL 32751
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  /2

  Est $327,302 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,483 Sq Ft

  1902 Water Ln, Maitland, FL 32751

  1902 Water Ln, Maitland, FL 32751
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  $799,000

  • 3 Beds
  • 3.5 Baths
  • 2,014 Sq Ft

  183 Orange Place, Maitland, FL 32751

  HUGE Price Reduction!! There is simply nothing that compares to this deal! This exquisite attached single family home blends contemporary elegance with unbeatable convenience in a truly coveted Maitland address. Just a stroll from Maitland Preparatory School and mere minutes from the vibrant heart of Downtown Winter Park, this residence offers the best of both worlds. From the moment you arrive,

  Christine Bennett EVOLVE PROPERTY GROUP LLC

  183 Orange Place, Maitland, FL 32751
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  /25

  $1,339 - $2,792 per month

  Courtney At Lake Shadow

  1 - 3 Beds

  545 S Keller Rd, Orlando, FL 32810

  Stylishly modern. Great location. A perfect home for you. The Courtney at Lake Shadow, a luxury apartment community in Orlando, Florida, offers open-concept layouts in a variety of pet-friendly 1, 2 & 3 bedroom floor plans. Enjoy your gourmet kitchen – stir up more than coffee. It’s fully equipped and ready for you to make fantastic meals for friends or craft home-cooked meals solo. Plus, each

  545 S Keller Rd, Orlando, FL 32810
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  $649,000 Sold Oct 17, 2025

  2304 Depauw Ave, Orlando, FL 32804

  • 3 Beds
  • 2.5 Baths
  • 1,668 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $389/SF
  • 199 Days On Market

  Current Estimated Value $652,000

  David Weekley Homes Central Living - Downtown

  2304 Depauw Ave, Orlando, FL 32804
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  /28

  Est $316,188 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,351 Sq Ft

  1979 Water Ln, Maitland, FL 32751

  1979 Water Ln, Maitland, FL 32751
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  /11

  $267,900

  • 2 Beds
  • 2 Baths
  • 1,275 Sq Ft

  1000 Winderley Place Unit 128, Maitland, FL 32751

  Immaculate 2BR/2BA Condo in a Gated Maitland Community. - Spacious and well maintained 2-bedroom, 2-bath condominium offering 1,275 sq. ft. of living space.Features include a sunken living room, wood, vinly and carpet flooring. and a bright, open layout. located in a desirable gated community with access to a community swimming pool and well-kept common areas.Conveniently located near shopping,

  Armelio Fernandez Aponte, Sr DOVER INTERNATIONAL CO., INC.

  1000 Winderley Place Unit 128, Maitland, FL 32751
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  /24

  $1,390 per month

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

  1125 Lake Shadow Cir Unit 5203, Maitland, FL 32751

  Welcome home to 1125 Lake Shadow Circle Unit#5203, a second floor 1 bedroom 1 bath condo in the Visconti community! The home features an open floor plan feel with the kitchen overlooking the dining and living room. The kitchen has brand new appliances including refrigerator, range and dishwasher. The living room is spacious and overlooks the dining area and kitchen. Through the kitchen, leads

  Paula Wells PRIMAC GROUP, INC

  1125 Lake Shadow Cir Unit 5203, Maitland, FL 32751
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  /2

  $490,000 Sold Jun 20, 2025

  1171 Covewood Trail, Maitland, FL 32751

  • 4 Beds
  • 2 Baths
  • 2,054 Sq Ft
  • Built 1967

  Last Sold Summary

  • 7% Below List Price
  • $239/SF
  • 2 Days On Market

  Current Estimated Value $503,554

  Last Listing Agent Rhonda Chesmore KELLY PRICE & COMPANY LLC

  1171 Covewood Trail, Maitland, FL 32751
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  /19

  Est $1,480,792 Not Listed For Sale

  940 S Lake Sybelia Dr, Maitland, FL 32751

  940 S Lake Sybelia Dr, Maitland, FL 32751
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  /47

  $927,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,309 Sq Ft

  821 Woods Ct, Maitland, FL 32751

  LOCATION! LOCATION! LOCATION! SERENE HOME in beautiful Dommerich Woods. Located on a quiet cul-de-sac, this unique .28+ acre property offers a single story, 4 bedroom + flex room split plan surrounded by peaceful nature. Brick driveway invites you to a gated courtyard leading to front door & fenced property offering complete privacy including pool, tranquil haven overlooking lush preserve & side

  Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  821 Woods Ct, Maitland, FL 32751
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  /35

  $1,595 - $2,115 per month

  Dawson

  1 - 3 Beds

  9000 Summit Centre Way, Orlando, FL 32810

  At Dawson Apartments, residents can find all that they need for a life of comfort and convenience. In each of our 1, 2, and 3 bedroom floor plans and throughout our community, the variety of gorgeous amenities are sure to accommodate every lifestyle. Our homes will all include gourmet kitchens with stainless steel appliances, walk-in closets, and private, screened-in patios. Throughout our

  9000 Summit Centre Way, Orlando, FL 32810
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  $150,000 Sold Jul 31, 2025

  539 Clark St, Maitland, FL 32751

  • 3 Beds
  • 1 Bath
  • 936 Sq Ft
  • Built 1951

  Last Sold Summary

  • 25% Below List Price
  • $160/SF
  • 70 Days On Market

  Current Estimated Value $171,432

  Last Listing Agent Alvin Moore MOREHOUSE REALTY INC

  539 Clark St, Maitland, FL 32751
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  Est $312,320 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft

  436 Poplar Ct, Maitland, FL 32751

  436 Poplar Ct, Maitland, FL 32751
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  /29

  $689,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,531 Sq Ft

  514 W Faith Terrace, Maitland, FL 32751

  Welcome to this beautifully remodeled single-story home in a perfect location---offering no stairs and effortless open living. This truly move-in ready residence features soaring ceilings and beautiful custom energy-efficient windows allowing an abundance of natural light. The modern chef's kitchen is the heart of the home with its bright eat-in area, built-in pantry, high-end cabinets and plenty

  Donna Bryant COLDWELL BANKER RESIDENTIAL RE

  514 W Faith Terrace, Maitland, FL 32751
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  /27

  $1,925 per month

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

  2837 Shadow View Cir, Maitland, FL 32751

  PRICE ADJUSTMENT — Updated & Move-In Ready Maitland Condo with New Carpet, New Paint and Appliances - 2-Car Garage & Flex Space in Gated Community This beautifully updated three-level condo offers the space and functionality rarely found in rental properties. Featuring 2 bedrooms plus a dedicated office/flex room and a private 2-car garage, this home is ideal for remote professionals, busy

  Nilufer Rohleder COLDWELL BANKER RESIDENTIAL RE

  2837 Shadow View Cir, Maitland, FL 32751
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  $270,000 Sold Jul 17, 2025

  531 Wigman Dr, Maitland, FL 32751

  • 4 Beds
  • 1.5 Baths
  • 1,301 Sq Ft
  • Built 1965

  Last Sold Summary

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

  Current Estimated Value $278,060

  Last Listing Agent Anthony Figueroa LLC OUTLET REALTY

  531 Wigman Dr, Maitland, FL 32751
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  /31

  Est $370,309 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,651 Sq Ft

  1010 Winderley Place Unit 143, Maitland, FL 32751

  1010 Winderley Place Unit 143, Maitland, FL 32751
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  $309,000

  • 2 Beds
  • 2 Baths
  • 1,164 Sq Ft

  1000 Winderley Place Unit 222, Maitland, FL 32751

  Discover Sun Bay Club – Maitland’s Hidden Gem on Lake Destiny!Behind the signature blue gates lies this exclusive 68-residence community perfectly situated on the shimmering shores of Lake Destiny. Just minutes from Winter Park and downtown Orlando, this 2-bedroom, 2-bath second-floor condo offers a perfect blend of luxury and low-maintenance living.Completely remodeled in 2022, this home

  Jackie Swisher TRUST EQUITY GROUP LLC

  1000 Winderley Place Unit 222, Maitland, FL 32751
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  /30

  $2,029 per month

  • Studio
  • 1 Bath
  • 300 Sq Ft
  • Condo for Rent

  1760 Pembrook Dr, Orlando, FL 32810

  Enjoy a fully furnished studio suite in our hotel at an affordable rate with free wi-fi, free utilities and free premium cable. Each studio suite has a full kitchen with full-size refrigerator, stovetop and microwave, and has a flexible workspace and plenty of storage. All our hotels are pet-friendly and have on-site guest laundry available. Plus, there are no long-term commitments and you can

  1760 Pembrook Dr, Orlando, FL 32810
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  $275,000 Sold Sep 23, 2025

  1460 Lake Shadow Cir Unit 7102, Maitland, FL 32751

  • 4 Beds
  • 2 Baths
  • 1,372 Sq Ft
  • Built 2000

  Last Sold Summary

  • 8% Below List Price
  • $200/SF
  • 83 Days On Market

  Current Estimated Value $274,035

  Last Listing Agent Lorie Gullian KELLER WILLIAMS ELITE PARTNERS III REALTY

  1460 Lake Shadow Cir Unit 7102, Maitland, FL 32751
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  Est $278,213 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,275 Sq Ft

  1000 Winderley Place Unit 144, Maitland, FL 32751

  1000 Winderley Place Unit 144, Maitland, FL 32751
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  /38

  $925,000

  • 4 Beds
  • 3.5 Baths
  • 3,451 Sq Ft

  1416 Caring Ct, Maitland, FL 32751

  Beautifully maintained Maitland home in the gated community of Montacino on Lake Charity. Conveniently located near Maitland City Center, Park Ave, Downtown Orlando, and RDV Sportsplex. Engineered hardwood floors lead from the entry to a formal living and dining room, powder bath, and into the great room with soaring ceilings open to the kitchen and patio. The gourmet kitchen features custom

  Richard Palmano PALMANO GROUP RE BROKERAGE LLC

  1416 Caring Ct, Maitland, FL 32751
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  /14

  $1,150 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Apartment for Rent

  2075 Howell Branch Rd Unit 109, Maitland, FL 32751

  MOVE-IN READY WITH BRAND NEW CARPETS! This cozy and well-located 1-bedroom, 1-bathroom unit is perfect for anyone seeking comfort and convenience! Nestled in a fantastic location, you'll be within walking distance to grocery stores, restaurants, and shopping, and just minutes from Downtown Winter Park, Full Sail University, Rollins College, Advent Health Winter Park, and more. The apartment

  Kevan Patel CENTRAL FLORIDA REALTY MANAGEMENT LLC

  2075 Howell Branch Rd Unit 109, Maitland, FL 32751
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  $524,900 Sold Aug 26, 2025

  2621 Queen Mary Place, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 2,130 Sq Ft
  • Built 1998

  Last Sold Summary

  • $246/SF
  • 1 Day On Market

  Current Estimated Value $533,065

  Last Listing Agent Michael Rains, P.A. ADAIR REALTY INC

  2621 Queen Mary Place, Maitland, FL 32751
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  /11

  Est $113,205 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 550 Sq Ft

  2422 Branch Way Unit 200, Maitland, FL 32751

  2422 Branch Way Unit 200, Maitland, FL 32751

Showing Results 81 - 120, Page 3 of 18