Maitland, FL Homes

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  $419,900 Pending

  • 3 Beds
  • 2 Baths
  • 2,426 Sq Ft

  135 Roosevelt Place, Maitland, FL 32751

  This charming home boasts a wealth of valuable upgrades and improvements, making it an enticing opportunity for anyone seeking a move-in ready property The roof was replaced in 2006, ensuring long-lasting durability. A significant renovation in 2017 introduced modern conveniences, including all-new kitchen appliances and luxurious vinyl plank flooring, with extra flooring thoughtfully

  Julimar Barreiro Pastrana SERHANT

  135 Roosevelt Place, Maitland, FL 32751
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  /65

  $1,600 - $3,550 per month

  Bell Trelago

  Studio - 3 Beds

  601 Trelago Way, Maitland, FL 32751

  Bell Trelago welcomes you to a refined lakeside retreat where luxury, comfort, and convenience shape every moment. You can enjoy a relaxed yet sophisticated lifestyle enhanced by thoughtful amenities, beautiful waterfront views, and effortless access to dining, retail, and entertainment. The community blends style and function with elegant finishes, spacious studio, one-, two-, and three-bedroom

  601 Trelago Way, Maitland, FL 32751
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  /2

  $475,000 Sold Dec 29, 2025

  1938 Michael Tiago Cir, Maitland, FL 32751

  • 4 Beds
  • 2.5 Baths
  • 2,708 Sq Ft
  • Built 2011

  Last Sold Summary

  • 4% Below List Price
  • $175/SF
  • 74 Days On Market

  Last Listing Agent Robin Mitchell ROBIN MITCHELL REALTY

  1938 Michael Tiago Cir, Maitland, FL 32751
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  /2

  Est $791,447 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,416 Sq Ft

  2440 Deloraine Trail, Maitland, FL 32751

  2440 Deloraine Trail, Maitland, FL 32751
• 

  

  

  /20

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,146 Sq Ft

  1033 Hamlet Dr, Maitland, FL 32751

  This charming 3-bedroom, 2-bathroom single-family home with the best of Florida living. Located in the north of Orlando (Maitland - Winter Park area). 1.3 miles to the Center of Winter Park Shopping Plaza (Office Depot, UPS, Ross, Marshalls, Home Goods, Five Below, LA Fitness, Petco and Michaels, Whole Foods Markets, and Banking). Access to major highways, minutes to downtown, and Orlando's

  Bennie Olivo BOX REAL ESTATE LLC

  1033 Hamlet Dr, Maitland, FL 32751
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  /29

  $2,000 per month

  • 3 Beds
  • 2 Baths
  • 1,160 Sq Ft
  • House for Rent

  319 Eaton St, Maitland, FL 32751

  Welcome to this beautifully maintained single-family home featuring 3 bedrooms and 2 full bathrooms with 1,160 sq. ft. of living space. Bright and open living areas with abundant natural light, modern finishes, and a comfortable layout. Enjoy a 2-car attached garage, central air, ceiling fans, and a great neighborhood location with convenient access to local parks, amenities, and community

  William Jusme, II MILLENNIUM REALTY CENTER LLC

  319 Eaton St, Maitland, FL 32751
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  /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 $6,535,764

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

  119 Whitecaps Cir, Maitland, FL 32751
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  /2

  Est $965,255 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,423 Sq Ft

  2081 Geronimo Trail, Maitland, FL 32751

  2081 Geronimo Trail, Maitland, FL 32751
• 

  

  /23

  $269,000 Pending

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

  920 Park Lake Cir Unit 36, Maitland, FL 32751

  Under contract-accepting backup offers. Welcome to 920 Park Lake Circle in charming Maitland, FL — a beautifully updated 3 bedroom, 2 bath condo offering style, warmth, and unbeatable location. Step into a bright, open living space with an upgraded kitchen featuring shaker cabinetry, quartz countertops, stainless steel appliances, and designer lighting. Wood laminate flooring runs throughout all

  Melissa Johnson EXP REALTY LLC

  920 Park Lake Cir Unit 36, Maitland, FL 32751
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  /89

  $1,495 - $2,945 per month

  The Tiffany at Maitland West

  1 - 3 Beds

  9301 Summit Centre Way, Orlando, FL 32810

  Submerge yourself into our culture. This resort-style, all-inclusive residential apartment community will take care of it all for you. 1-2 and 3-bedroom apartment homes feature beautiful, modern fixtures and appliances. Grey faux wood tile adorns the kitchen and living spaces. Cabinets that are a gorgeous, modern, two-toned zebra pattern with more storage space than you'd expect. Most units

  9301 Summit Centre Way, Orlando, FL 32810
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  /2

  $550,000 Sold May 02, 2025

  1870 Geronimo Trail, Maitland, FL 32751

  • Land
  • 0.27 Acre
  • $2,037,037 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 113 Days On Market

  Current Estimated Value $549,795

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

  1870 Geronimo Trail, Maitland, FL 32751
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  /16

  Est $161,356 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 672 Sq Ft

  1400 Lake Shadow Cir Unit 10304, Maitland, FL 32751

  1400 Lake Shadow Cir Unit 10304, Maitland, FL 32751
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  /34

  $850,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft

  2270 Deloraine Trail, Maitland, FL 32751

  Under contract-accepting backup offers. This beautifully updated 4-bedroom, 2-bath pool home offers 2,000 square feet of inviting living space on a spacious corner lot in highly desirable Maitland. The open living, kitchen, and dining area features a striking limestone fireplace, crown molding, custom built-ins, laminate wood flooring, and abundant natural light through French doors and

  Amy Turner KELLER WILLIAMS WINTER PARK

  2270 Deloraine Trail, Maitland, FL 32751
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  /14

  $1,149 per month

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

  476 Banyon Tree Cir Unit 102, Maitland, FL 32751

  This 1st floor 1bed 1 bath condo is located in the community of Carrington Park in Maitland! It has a living/dining room combo with vinyl flooring throughout and a fresh coat of paint! The kitchen has a refrigerator, range and dishwasher as well as a large pantry. The bedroom is very spacious and has a walk in closet. The unit also comes with a patio! *ADDITIONAL HOA APPROVAL**WATER, SEWER

  Nancy Guadagnino SPECIALIZED PROPERTY MANAGEMENT

  476 Banyon Tree Cir Unit 102, Maitland, FL 32751
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  /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 $675,512

  Last Listing Agent Kevin Asenjo COLDWELL BANKER RESIDENTIAL RE

  460 Forestwood Ln, Maitland, FL 32751
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  /25

  Est $676,099 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft

  2222 Chippewa Trail, Maitland, FL 32751

  2222 Chippewa Trail, Maitland, FL 32751
• 

  

  /23

  $399,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,394 Sq Ft

  210 Magnolia Rd Unit 106, Maitland, FL 32751

  Under contract-accepting backup offers. RARE 3-BEDROOM GROUND FLOOR UNIT IN MAITLAND HOUSE. Enter this unit just steps from the assigned covered parking space to find a comfortable three bedroom unit that looks out to the tranquil pool area. The great room focus is the wood burning fireplace, and it has plenty of space for your dining table and living room furniture. The bright, well-equipped

  Sue Gilman KELLER WILLIAMS WINTER PARK

  210 Magnolia Rd Unit 106, Maitland, FL 32751
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  /20

  $1,735 - $3,467 per month

  The Adeline

  1 - 3 Beds

  304 Lake Ave, Maitland, FL 32751

  Find the perfect balance of sophistication and relaxation at The Adeline in urban Maitland. Our community offers 1, 2, and 3 bedroom residences with modern features and luxurious amenities. Whether you live alone, are happy in love, or enjoy having roommates, feel at home in our elegant, French-inspired units. In the heart of the Greater Orlando area, The Adeline provides a warm, engaging

  304 Lake Ave, Maitland, FL 32751
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  /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

  Last Listing Agent Dan Samatulski MAINFRAME REAL ESTATE

  741 Robinhood Dr, Maitland, FL 32751
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  /30

  Est $449,065 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,193 Sq Ft

  2027 Michael Tiago Cir, Maitland, FL 32751

  2027 Michael Tiago Cir, Maitland, FL 32751
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  /10

  $459,000

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft

  1140 S Orlando Ave Unit E16, Maitland, FL 32751

  Lovely direct waterfront condominium with large screen porch overlooking beautiful 451 acre Lake Maitland. Screened terrace is wonderful for enjoying the lake. Share the same view as multimillion dollar homes. Updated floor plan with open kitchen, tile throughout, French doors. Maitland is a very central community of greater Orlando. Close to many great restaurants along Orlando Avenue and

  Jack Keller JACK KELLER INC

  1140 S Orlando Ave Unit E16, Maitland, FL 32751
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  /10

  $1,950 per month

  • 3 Beds
  • 2.5 Baths
  • 1,583 Sq Ft
  • Condo for Rent

  1825 Shadow View Cir, Maitland, FL 32751

  Stunning 3 story Townhome with 2 car garage in resort style community of Visconti. Featuring 3 bed and 2.5 bath, this light and bright unit offers wood flooring and ceramic tile throughout, an open floor plan with brand new paint and light fixtures. Located within minutes to shopping, entertainment and I-4. Available now !

  Andreas Kunert KUNERT REALTY INC

  1825 Shadow View Cir, Maitland, FL 32751
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  /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 $558,382

  Last Listing Agent Nicole Seybold FANNIE HILLMAN & ASSOCIATES

  2040 Mohawk Trail, Maitland, FL 32751
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  /46

  Est $451,278 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,249 Sq Ft

  2030 Michael Tiago Cir, Maitland, FL 32751

  2030 Michael Tiago Cir, Maitland, FL 32751
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  /62

  $920,000

  • 5 Beds
  • 4 Baths
  • 3,769 Sq Ft

  1619 Druid Rd, Maitland, FL 32751

  Tucked into prestigious Maitland Florida on coveted Druid Road, this one-of-a-kind residence offers the kind of flexibility—and lifestyle—that’s hard to find and even harder to forget. With 5 bedrooms and 4 full baths, this meticulously cared-for property is designed to fit real life beautifully: a 4-bedroom, 3-bath main home, plus a private 1-bedroom, 1-bath apartment with a brand-new kitchen

  Mark Adams KELLER WILLIAMS REALTY AT THE PARKS

  1619 Druid Rd, Maitland, FL 32751
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  /47

  $1,690 - $3,842 per month

  400 North

  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 N Orlando Ave, Maitland, FL 32751
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  /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 $3,822,637

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

  33 Eastwind Ln, Maitland, FL 32751
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  /22

  Est $177,646 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,206 Sq Ft

  2333 Coawood Ct Unit 103, Maitland, FL 32751

  2333 Coawood Ct Unit 103, Maitland, FL 32751
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  /45

  $700,000 Pending

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

  1100 Willowbrook Trail, Maitland, FL 32751

  Under contract-accepting backup offers. Incredible Opportunity to create your own dream home in the coveted Lake Sybelia / Maitland Woods neighborhood !! Spacious, One Story Living in this 4 bedroom, 3 bathroom home. Located just steps from Lake Sybelia Park. Convenient to I-4, Maitland Center, Winter Park, Altamonte Springs and downtown Orlando. After decades of being the stage for shared love

  Skip Kirst COLLADO REAL ESTATE

  1100 Willowbrook Trail, Maitland, FL 32751
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  /32

  $2,200 per month

  • 3 Beds
  • 3 Baths
  • 1,328 Sq Ft
  • Condo for Rent

  1718 Gulfview Dr Unit 429 B, Maitland, FL 32751

  3 Bedroom/3Bathroom two story condo with a one car garage. The main living areas are on the first level, including a laundry room, living/dining combo and a kitchen with lots of cabinets, one bedroom overlooking the back patio, and a full bath. There are two bedrooms upstairs with their own private bathrooms. The front bedroom has a balcony overlooking the green space and wooded area. The back of

  Dawn Slaughter TRUSTHOME PROPERTIES INC

  1718 Gulfview Dr Unit 429 B, Maitland, FL 32751
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  /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 $487,546

  Last Listing Agent Travis Cepregi KELLER WILLIAMS WINTER PARK

  204 Quayside Cir Unit 601, Maitland, FL 32751
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  /11

  Est $434,826 Not Listed For Sale

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

  1100 S Orlando Ave Unit 704, Maitland, FL 32751

  1100 S Orlando Ave Unit 704, Maitland, FL 32751
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  /50

  $1,199,000

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

  791 Sequoia Trail, Maitland, FL 32751

  Discover a rare opportunity in Dommerich Woods, a distinguished and established Maitland neighborhood celebrated for its rich heritage. Situated on .33 acre of lushly landscaped grounds, this remarkable property welcomes with paver drive and enjoys a tranquil setting along apeaceful creek connecting Lake Minnehaha and Lake of the Woods - creating an atmosphere of natural elegance and

  David Van Wormer VANWORMER REALTY & DEVELOPMENT

  791 Sequoia Trail, Maitland, FL 32751
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  /37

  $2,097 - $3,839 per month

  Perla Gem Lake

  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.

  100 Boucle Jeanne Cir, Maitland, FL 32751
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  /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 $964,159

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

  91 Minnehaha Cir, Maitland, FL 32751
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  /21

  Est $301,519 Not Listed For Sale

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

  1000 Winderley Place Unit 126, Maitland, FL 32751

  1000 Winderley Place Unit 126, Maitland, FL 32751
• 

  

  /32

  $1,200,000 Pending

  • 5 Beds
  • 3 Baths
  • 2,868 Sq Ft

  1750 Cheyenne Trail, Maitland, FL 32751

  Built in 2014 and set within the highly sought-after Dommerich Estates neighborhood of Maitland, this thoughtfully maintained two-story home offers a rare blend of space, function, and location. With five bedrooms, three full bathrooms, and a flexible bonus room, the layout is designed to adapt easily to modern living. The entry opens to a formal dining space, while an additional room just off

  Kyle Grafton FANNIE HILLMAN & ASSOCIATES

  1750 Cheyenne Trail, Maitland, FL 32751
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  /19

  $1,450 per month

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

  1515 Legacy Club Dr, Maitland, FL 32751

  One-bedroom, one-bath residence with an attached one-car garage located in the desirable gated community of Visconti. Upon entry, stairs lead to the main living area featuring a spacious open floor plan. The kitchen offers ample cabinet and countertop space and opens to the dining area and family room, creating an ideal layout for everyday living and entertaining. The upper level includes the

  Kathryn Stieger ORLANDO INLAND REALTY LLC

  1515 Legacy Club Dr, Maitland, FL 32751
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  /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

  Last Listing Agent Jason Asa LPT REALTY, LLC

  2133 Falkner Rd, Maitland, FL 32751
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  /15

  Est $110,513 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 550 Sq Ft

  551 Flemming Way Unit 101, Maitland, FL 32751

  551 Flemming Way Unit 101, Maitland, FL 32751

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