Maitland, FL Homes

• 

  

  

  /35

  $449,990 Pending

  • 3 Beds
  • 2 Baths
  • 1,430 Sq Ft

  2065 Derbyshire Rd, Maitland, FL 32751

  Under contract-accepting backup offers. Beautifully renovated and move-in ready, this 3-bedroom, 2-bath home offers modern design in a .24 acre lots, solid upgrades, and comfortable living in a prime Maitland location. Featuring an open-concept layout filled with abundant natural light, the home delivers a warm and inviting atmosphere from the moment you enter. The updated kitchen serves as the

  

  Ceila Morales

  EXP REALTY LLC

  (321) 326-7610

  2065 Derbyshire Rd, Maitland, FL 32751
• 

  

  

  /25

  Starting at $1,430

  Total Monthly Price

  • 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

  Courtney At Lake Shadow

  (689) 207-3528

  

  545 S Keller Rd, Orlando, FL 32810
• 

  

  /2

  $6,650,000 Sold Jun 27, 2025

  119 Whitecaps Cir, Maitland, FL 32751

  • 4 Beds
  • 5.5 Baths
  • 6,800 Sq Ft
  • Built 2004

  Last Sold Summary

  • $978/SF

  Current Estimated Value $6,631,006

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

  119 Whitecaps Cir, Maitland, FL 32751
• 

  

  

  /11

  Est $427,228 Not Listed For Sale

  1100 S Orlando Ave Unit 704, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,285 Sq Ft
  • Built 1973

  1100 S Orlando Ave Unit 704, Maitland, FL 32751

  Last Sold Summary

  • 2% Above List Price
  • $327/SF
  • 49 Days On Market

  • Last Sold Price $420,000
  • Sep 13, 2023

  Last Listing Agent Joann Beck BECK REALTY LLC
• 

  

  

  /45

  $249,900

  • 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

  (321) 850-5396

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

  

  /37

  Starting at $1,977 Per Month

  • 1 - 3 Beds

  100 Boucle Jeanne Cir, Maitland, FL 32751

  Drink in the waterfront views. Drop your kayak in for an evening cruise. Dip your toes in the saltwater pool. When you’re here, every day feels like a waterside retreat. Only it’s not a vacation, it’s your home. With nature-inspired interior design, multiple outdoor living spaces and direct lake access, Perla Gem Lake is luxury lakeside living.

  Perla Gem Lake

  (689) 209-1332

  

  100 Boucle Jeanne Cir, Maitland, FL 32751
• 

  /2

  $660,000 Sold May 27, 2025

  460 Forestwood Ln, Maitland, FL 32751

  • 4 Beds
  • 2 Baths
  • 2,049 Sq Ft
  • Built 1979

  Last Sold Summary

  • 12% Below List Price
  • $322/SF
  • 23 Days On Market

  Current Estimated Value $662,353

  Last Listing Agent Kevin Asenjo COLDWELL BANKER REALTY

  460 Forestwood Ln, Maitland, FL 32751
• 

  

  /21

  Est $297,178 Not Listed For Sale

  1000 Winderley Place Unit 126, Maitland, FL 32751

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

  1000 Winderley Place Unit 126, Maitland, FL 32751

  Last Sold Summary

  • 4% Below List Price
  • $202/SF
  • 73 Days On Market

  • Last Sold Price $310,000
  • Feb 21, 2024

  Last Listing Agent Raul Veitia BELMONT REALTY
• 

  

  /55

  $649,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,877 Sq Ft

  106 Oakwood Dr, Maitland, FL 32751

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. FINAL SUBMISSION WINDOW – SELLER HAS SET A FIRM DEADLINE TO SECURE CONTRACT. ALL PROPOSALS DUE MAY 11. FULLY RENOVATED Maitland home offered for a limited time only. Seller will review all submitted contracts, including those below list price, and is open to structuring terms that work - including potential

  

  Kikzeny Cartagena

  LPT REALTY, LLC

  (321) 850-2430

  106 Oakwood Dr, Maitland, FL 32751
• 

  

  /38

  Starting at $1,720

  Total Monthly Price

  • 1 - 3 Beds

  9000 Summit Centre Way, Orlando, FL 32810

  Dawson Apartments delivers elevated lakeside living in North Orlando, pairing upscale design with a location that keeps you connected to the best of Central Florida. Surrounded by water views and lush landscaping, this luxury community offers a refined retreat while placing shopping, dining, recreation and major roadways just minutes from home. Choose from spacious one-, two- and three-bedroom

  Dawson

  (689) 220-0109

  

  9000 Summit Centre Way, Orlando, FL 32810
• 

  /2

  $455,000 Sold Nov 10, 2025

  741 Robinhood Dr, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,239 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Above List Price
  • $367/SF
  • 18 Days On Market

  Current Estimated Value $443,236

  Last Listing Agent Dan Samatulski MAINFRAME REAL ESTATE

  741 Robinhood Dr, Maitland, FL 32751
• 

  

  /15

  Est $105,924 Not Listed For Sale

  551 Flemming Way Unit 101, Maitland, FL 32751

  • 1 Bed
  • 1 Bath
  • 550 Sq Ft
  • Built 1973

  551 Flemming Way Unit 101, Maitland, FL 32751

  Last Sold Summary

  • 4% Below List Price
  • $200/SF
  • 1 Day On Market

  • Last Sold Price $110,000
  • Feb 05, 2024

  Last Listing Agent Kathryn Stieger ORLANDO INLAND REALTY LLC
• 

  

  /30

  $157,500

  • 1 Bed
  • 1 Bath
  • 672 Sq Ft

  1275 Lake Shadow Cir Unit 13206, Maitland, FL 32751

  One or more photo(s) has been virtually staged. Seller to offer credit of up to $5000 towards buyer closing costs. Water views, brand-new mechanicals, and the best price in the building. This 1-bedroom, 1-bath condo at Visconti is offered at $9,000 less than the only comparable unit in the same building — and comes with a new Goodman 2-ton, 14.3 SEER HVAC system (2025), new water heater with

  Trevin Perez REDFIN CORPORATION

  1275 Lake Shadow Cir Unit 13206, Maitland, FL 32751
• 

  

  /47

  Starting at $1,787 Per Month

  • 1 - 3 Beds

  400 N Orlando Ave, Maitland, FL 32751

  At 400 North, thoughtful home design meets effortless living in one of Maitland?s most connected neighborhoods. From the resort-style pool and fire pit lounge to the tranquil Zen courtyard, every outdoor space invites you to slow down and recharge. Inside, curated apartment features such as eat-in kitchen countertop seating and tiled baths meet spectacular lakeside views. With on-site retail and

  400 North

  (689) 219-8784

  

  400 N Orlando Ave, Maitland, FL 32751
• 

  /2

  $550,000 Sold Jul 01, 2025

  2040 Mohawk Trail, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,754 Sq Ft
  • Built 1961

  Last Sold Summary

  • 6% Below List Price
  • $314/SF
  • 17 Days On Market

  Current Estimated Value $555,602

  Last Listing Agent Nicole Seybold FANNIE HILLMAN & ASSOCIATES

  2040 Mohawk Trail, Maitland, FL 32751
• 

  

  /25

  Est $305,405 Not Listed For Sale

  437 Poplar Ct, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft
  • Built 1983

  437 Poplar Ct, Maitland, FL 32751

  Last Sold Summary

  • 1% Below List Price
  • $262/SF
  • 1 Day On Market

  • Last Sold Price $310,000
  • Jul 28, 2023

  Last Listing Agent Chris Creegan CREEGAN GROUP
• 

  

  /55

  $974,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,872 Sq Ft

  1817 Braeloch Ct, Maitland, FL 32751

  Under contract-accepting backup offers. Welcome to this stunning home in Maitland, located at 1817 Braeloch Ct. A welcoming foyer opens to elegant formal living and dining rooms featuring gorgeous fixtures, plantation shutters throughout, 51⁄2-inch baseboards, and beautiful manufactured wood flooring. Vaulted ceilings and skylights fill the home with natural light, while a cozy wood-burning

  Abby Nelson RE/MAX 200 REALTY

  1817 Braeloch Ct, Maitland, FL 32751
• 

  

  /35

  $2,399 Per Month

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

  1776 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

  (321) 216-9563

  1776 Pembrook Dr, Orlando, FL 32810
• 

  /2

  $3,950,000 Sold Jun 17, 2025

  33 Eastwind Ln, Maitland, FL 32751

  • 5 Beds
  • 4.5 Baths
  • 4,715 Sq Ft
  • Built 2024

  Last Sold Summary

  • $838/SF
  • 0 Days On Market

  Current Estimated Value $3,736,269

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

  33 Eastwind Ln, Maitland, FL 32751
• 

  /2

  Est $314,435 Not Listed For Sale

  1902 Water Ln, Maitland, FL 32751

  • 3 Beds
  • 2.5 Baths
  • 1,483 Sq Ft
  • Built 1983

  1902 Water Ln, Maitland, FL 32751

  Last Sold Summary

  • 2% Below List Price
  • $216/SF
  • 30 Days On Market

  • Last Sold Price $320,000
  • Nov 28, 2024

  Last Listing Agent Keith Moore HOMEVEST REALTY
• 

  

  /43

  $769,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,413 Sq Ft

  101 Mariner Way, Maitland, FL 32751

  Under contract-accepting backup offers. Welcome to an exceptional residence in the Maitland Isle subdivision, where timeless elegance meets modern comfort. This beautifully updated four-bedroom, two-bath home spans 2,413 square feet and offers exclusive private lake access to Lake Maitland on the prestigious Winter Park Chain of Lakes. Designed for refined living and effortless entertaining, the

  MaryAnne Branner PREMIER SOTHEBY'S INTL. REALTY

  101 Mariner Way, Maitland, FL 32751
• 

  

  /35

  $2,039 Per Month

  • Studio
  • 1 Bath
  • 300 Sq Ft
  • Furnished Studio-Orlando - Maitland - Summit Tower Blvd

  1951 Summit Tower Blvd, 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

  Furnished Studio-Orlando - Maitland - Summit Tower Blvd

  (321) 490-3256

  1951 Summit Tower Blvd, Orlando, FL 32810
• 

  /2

  $515,000 Sold Sep 10, 2025

  204 Quayside Cir Unit 601, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,270 Sq Ft
  • Built 1984

  Last Sold Summary

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

  Current Estimated Value $489,490

  Last Listing Agent Travis Cepregi KELLER WILLIAMS WINTER PARK

  204 Quayside Cir Unit 601, Maitland, FL 32751
• 

  

  /28

  Est $306,131 Not Listed For Sale

  1979 Water Ln, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,351 Sq Ft
  • Built 1983

  1979 Water Ln, Maitland, FL 32751

  Last Sold Summary

  • 6% Below List Price
  • $241/SF
  • 0 Days On Market

  • Last Sold Price $325,000
  • Jul 01, 2024

  Last Listing Agent Alexais Montenegro LA ROSA REALTY INTERNACIONAL L
• 

  

  /55

  $332,500

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft

  1000 S Orlando Ave Unit B25, Maitland, FL 32751

  Offered at a newly improved price, this highly desirable residence at Maitland Harbour is located within a boutique 38-unit lakefront condominium community nestled in the heart of Maitland. Ideally positioned on Lake Maitland—the largest lake on the Winter Park Chain of Lakes—this intimate and picturesque enclave offers access to the entire chain and a truly exceptional waterfront lifestyle. A

  Padgett McCormick KELLY PRICE & COMPANY LLC

  1000 S Orlando Ave Unit B25, Maitland, FL 32751
• 

  

  /30

  $2,069 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

  (321) 850-3424

  1760 Pembrook Dr, Orlando, FL 32810
• 

  /2

  $279,000 Sold Mar 06, 2026

  920 Park Lake Cir Unit 36, Maitland, FL 32751

  • 3 Beds
  • 2.5 Baths
  • 1,486 Sq Ft
  • Built 1972

  Last Sold Summary

  • 4% Above List Price
  • $188/SF
  • 72 Days On Market

  Current Estimated Value $264,750

  Last Listing Agent Melissa Johnson EXP REALTY LLC

  920 Park Lake Cir Unit 36, Maitland, FL 32751
• 

  

  /33

  Est $298,250 Not Listed For Sale

  436 Poplar Ct, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft
  • Built 1983

  436 Poplar Ct, Maitland, FL 32751

  Last Sold Summary

  • 3% Below List Price
  • $261/SF
  • 6 Days On Market

  • Last Sold Price $308,500
  • Jun 05, 2024

  Last Listing Agent Nick Romero CHARLES RUTENBERG REALTY ORLANDO
• 

  

  /20

  $979,000

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

  1281 Wellington Terrace, Maitland, FL 32751

  Beautiful and spacious home at 1281 Wellington Terrace featuring high beam ceilings and elegant tile floors throughout. The open layout offers wonderful natural light and two master bedrooms, perfect for flexible living. New windows add comfort and efficiency. Enjoy a private, low-maintenance backyard ideal for relaxing or entertaining. Located in a beautiful neighborhood just minutes from Winter

  Sinan Zakaria LISTED SIMPLY

  1281 Wellington Terrace, Maitland, FL 32751
• 

  

  /20

  $1,892 Per Month

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

  9301 Summit Centre Way Unit 2313, Orlando, FL 32810

  Landing is a top-rated, fully furnished apartment network with thousands of homes across 250+ U.S. cities. With premium amenities, a mobile app to manage your stay, and 24/7 support. Our apartments have everything you need for monthly and longer stays. 6-Month+ Stay base rent: starts at $1977/mo12-Month+ Stay base rent: starts at $1892/moLanding's apartments at The Tiffany at

  (628) 227-6546

  9301 Summit Centre Way Unit 2313, Orlando, FL 32810
• 

  /2

  $970,000 Sold Jul 31, 2025

  91 Minnehaha Cir, Maitland, FL 32751

  • 4 Beds
  • 2 Baths
  • 2,826 Sq Ft
  • Built 1971

  Last Sold Summary

  • 1% Below List Price
  • $343/SF
  • 6 Days On Market

  Current Estimated Value $954,817

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

  91 Minnehaha Cir, Maitland, FL 32751
• 

  

  /46

  Est $265,349 Not Listed For Sale

  1000 Winderley Place Unit 144, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,275 Sq Ft
  • Built 1982

  1000 Winderley Place Unit 144, Maitland, FL 32751

  Last Sold Summary

  • 2% Below List Price
  • $212/SF
  • 4 Days On Market

  • Last Sold Price $270,000
  • Jun 30, 2023

  Last Listing Agent James Lacovara FLORIDA ONE REAL ESTATE LLC
• 

  

  /60

  $1,100,000

  • 5 Beds
  • 4 Baths
  • 3,270 Sq Ft

  987 Brightwater Cir, Maitland, FL 32751

  Your dream home awaits. Welcome to this exquisitely Renovated 4/4 PLUS OFFICE PLUS BONUS ROOM POOL HOME. Located in the gorgeous guard gated enclave of Maitland Club. From the moment you enter, soaring ceilings and an elegant 3-way split floor plan create a sense of openness and refined comfort. At the heart of the home lies a beautiful updated kitchen, complete with a spacious center island,

  Gale Milgrim KELLER WILLIAMS WINTER PARK

  987 Brightwater Cir, Maitland, FL 32751
• 

  

  /20

  $1,892 Per Month

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

  9301 Summit Centre Way Unit 1223, Orlando, FL 32810

  Landing is a top-rated, fully furnished apartment network with thousands of homes across 250+ U.S. cities. With premium amenities, a mobile app to manage your stay, and 24/7 support. Our apartments have everything you need for monthly and longer stays. 6-Month+ Stay base rent: starts at $1977/mo12-Month+ Stay base rent: starts at $1892/moLanding's apartments at The Tiffany at

  (628) 250-5806

  9301 Summit Centre Way Unit 1223, Orlando, FL 32810
• 

  /2

  $458,000 Sold Dec 26, 2025

  2133 Falkner Rd, Maitland, FL 32751

  • 4 Beds
  • 3 Baths
  • 1,779 Sq Ft
  • Built 1998

  Last Sold Summary

  • 2% Above List Price
  • $257/SF
  • 5 Days On Market

  Current Estimated Value $453,593

  Last Listing Agent Jason Asa LPT REALTY, LLC

  2133 Falkner Rd, Maitland, FL 32751
• 

  

  /11

  Est $112,556 Not Listed For Sale

  2422 Branch Way Unit 200, Maitland, FL 32751

  • 1 Bed
  • 1 Bath
  • 550 Sq Ft
  • Built 1973

  2422 Branch Way Unit 200, Maitland, FL 32751

  Last Sold Summary

  • 13% Below List Price
  • $236/SF
  • 19 Days On Market

  • Last Sold Price $130,000
  • Jul 18, 2023

  Last Listing Agent Ada Sanchez HOME BUYER HELPER REAL ESTATE LLC
• 

  

  /28

  $739,990

  • 3 Beds
  • 2 Baths
  • 1,495 Sq Ft

  1741 Lyndale Blvd, Maitland, FL 32751

  Charming Newly Renovated Bungalow in Prime Maitland Location – Move-In Ready with Endless Potential!Discover this beautifully updated 3-bedroom, 2-bath bungalow at 1741 Lyndale Blvd, Maitland, FL 32751 – perfectly positioned on the edge of Winter Park for an unbeatable blend of tranquility and convenience. Freshly renovated and move-in ready, this home offers immediate comfort while sitting

  Matías Ugarte CHARLES RUTENBERG REALTY ORLANDO

  1741 Lyndale Blvd, Maitland, FL 32751
• 

  

  /20

  $1,892 Per Month

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

  9301 Summit Centre Way Unit 4303, Orlando, FL 32810

  Landing is a top-rated, fully furnished apartment network with thousands of homes across 250+ U.S. cities. With premium amenities, a mobile app to manage your stay, and 24/7 support. Our apartments have everything you need for monthly and longer stays. 6-Month+ Stay base rent: starts at $1977/mo12-Month+ Stay base rent: starts at $1892/moLanding's apartments at The Tiffany at

  (415) 653-0687

  9301 Summit Centre Way Unit 4303, Orlando, FL 32810
• 

  /2

  $235,000 Sold Mar 30, 2026

  1550 Gulfview Dr Unit 444B, Maitland, FL 32751

  • 3 Beds
  • 3 Baths
  • 1,328 Sq Ft
  • Built 1982

  Last Sold Summary

  • 2% Below List Price
  • $177/SF
  • 22 Days On Market

  Current Estimated Value $237,443

  Last Listing Agent Tom Graves FUN HOMES

  1550 Gulfview Dr Unit 444B, Maitland, FL 32751
• 

  

  /13

  Est $149,960 Not Listed For Sale

  1275 Lake Shadow Cir Unit 13208, Maitland, FL 32751

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

  1275 Lake Shadow Cir Unit 13208, Maitland, FL 32751

  Last Sold Summary

  • 11% Below List Price
  • $251/SF
  • 136 Days On Market

  • Last Sold Price $169,000
  • Jan 18, 2024

  Last Listing Agent Courtney Davis ABSOLUTE REALTY GROUP, LLC

Showing Results 41 - 80, Page 2 of 18