Maitland, FL Homes

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  /20

  $719,990

  $10K PRICE DROP

  • 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 situated in

  Robert Dion D & D PROPERTY MANAGEMENT SOLUTIONS LLC

  1741 Lyndale Blvd, Maitland, FL 32751
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  /20

  $1,892 Per Month

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

  9301 Summit Centre Way Unit 1317, 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 $1892/mo12-Month+ Stay base rent: starts at $1892/moLanding's apartments at The Tiffany at

  9301 Summit Centre Way Unit 1317, Orlando, FL 32810
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  /2

  $255,000

  Sold Dec 08, 2025

  240 Cherrywood Dr, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,161 Sq Ft
  • Built 1959

  Last Sold Summary

  • 9% Below List Price
  • $220/SF
  • 6 Days On Market

  Current Estimated Value $261,426

  Last Listing Agent Martha Grasty EXP REALTY LLC

  240 Cherrywood Dr, Maitland, FL 32751
• 

  

  /2

  Est $403,920

  Not Listed For Sale

  1930 Rogers Ave, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,625 Sq Ft
  • Built 2024

  1930 Rogers Ave, Maitland, FL 32751

  Last Sold Summary

  • 4 Days On Market
• 

  

  

  /9

  $3,990,900

  $500K PRICE DROP

  • Land
  • 7.82 Acres
  • $510,345 per Acre

  1250 N Maitland Ave, Maitland, FL 32751

  Exceptional opportunity for commercial developers, residential builders, or those seeking a private estate within the City of Maitland, Orange County. This rare offering includes approximately ±8 acres of usable land comprising multiple contiguous parcels and rights-of-way. The property is designated as a Traditional Neighborhood and zoned RS-2. A previously submitted Planned Development

  Armando Gonzalez AG REALTY SERVICES LLC

  1250 N Maitland Ave, Maitland, FL 32751
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  /20

  $1,892 Per Month

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

  9301 Summit Centre Way Unit 1303, 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 $1892/mo12-Month+ Stay base rent: starts at $1892/moLanding's apartments at The Tiffany at

  9301 Summit Centre Way Unit 1303, Orlando, FL 32810
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  /2

  $330,000

  Sold Dec 30, 2025

  735 Gamewell Ave, Maitland, FL 32751

  • 2 Beds
  • 1 Bath
  • 938 Sq Ft
  • Built 1952

  Last Sold Summary

  • $352/SF
  • 2 Days On Market

  Current Estimated Value $332,641

  Last Listing Agent Heather Pryor KELLER WILLIAMS ADVANTAGE REALTY

  735 Gamewell Ave, Maitland, FL 32751
• 

  

  /22

  Est $259,616

  Not Listed For Sale

  1714 Gulfview Dr Unit 427-C, Maitland, FL 32751

  • 3 Beds
  • 3 Baths
  • 1,328 Sq Ft
  • Built 1981

  1714 Gulfview Dr Unit 427-C, Maitland, FL 32751

  Last Sold Summary

  • 1 Day On Market
• 

  

  /34

  $1,800,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,567 Sq Ft

  1130 Mechanic St, Maitland, FL 32751

  Pre-Construction. To be built. Come build your dream home on this exceptional homesite in the heart of Maitland.This stunning new construction single-family residence will feature 4 bedrooms, 4.5 bathrooms, and 3,567 square feet of thoughtfully designed living space across two stories, showcasing sleek modern finishes and open-concept living ideal for today’s lifestyle. Set on a 0.26-acre

  Richard Palmano PALMANO GROUP RE BROKERAGE LLC

  1130 Mechanic St, Maitland, FL 32751
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  /20

  $1,892 Per Month

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

  9301 Summit Centre Way Unit 1313, 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 $1892/mo12-Month+ Stay base rent: starts at $1892/moLanding's apartments at The Tiffany at

  9301 Summit Centre Way Unit 1313, Orlando, FL 32810
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  /2

  $385,000

  Sold Feb 24, 2026

  210 Magnolia Rd Unit 106, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,394 Sq Ft
  • Built 1971

  Last Sold Summary

  • 4% Below List Price
  • $276/SF
  • 16 Days On Market

  Current Estimated Value $383,417

  Last Listing Agent Sue Gilman KELLER WILLIAMS WINTER PARK

  210 Magnolia Rd Unit 106, Maitland, FL 32751
• 

  /2

  Est $334,819

  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
• 

  

  /46

  $999,000

  $101K PRICE DROP Pending

  • 4 Beds
  • 3 Baths
  • 2,300 Sq Ft

  921 N Thistle Ln, Maitland, FL 32751

  Under contract-accepting backup offers. Fully renovated pool home in the heart of Dommerich featuring a rare dual-primary layout and a 2019-built owner’s suite addition—designed for modern living and effortless maintenance. Originally built in 1967 and completely reimagined in 2019, the home blends timeless character with major system upgrades including roof, HVAC, plumbing, electrical, windows,

  Garrett McGinnis VISTA NATIONAL MANAGEMENT INC

  921 N Thistle Ln, Maitland, FL 32751
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  /20

  $1,956 Per Month

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

  9301 Summit Centre Way Unit 4218, 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 $1956/mo12-Month+ Stay base rent: starts at $1956/moLanding's apartments at The Tiffany at

  9301 Summit Centre Way Unit 4218, Orlando, FL 32810
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  /2

  $555,000

  Sold Oct 01, 2025

  1771 Chinook Trail, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,704 Sq Ft
  • Built 1959

  Last Sold Summary

  • 4% Below List Price
  • $326/SF
  • 20 Days On Market

  Current Estimated Value $564,761

  Last Listing Agent Hazel Sun RE/MAX 200 REALTY

  1771 Chinook Trail, Maitland, FL 32751
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  /2

  Est $273,528

  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
• 

  

  /30

  $598,000

  • 4 Beds
  • 2 Baths
  • 2,667 Sq Ft

  1241 Manchester Rd, Maitland, FL 32751

  Welcome to English Estates, one of Maitland’s most desirable neighborhoods. This 4-bedroom, 2-bath home has been thoughtfully updated and is ready for its next owner. The home features an open living area, updated kitchen and bathrooms, new plumbing, a new roof, a flex room, screened lanai, and a spacious backyard. Conveniently located near shopping, restaurants, parks, and major roadways,

  1241 Manchester Rd, Maitland, FL 32751
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  /11

  $1,850 Per Month

  • 3 Beds
  • 1 Bath
  • 1,409 Sq Ft
  • House for Rent

  523 Oak Ave, Maitland, FL 32751

  Nestled in a peaceful, wooded setting in desirable Maitland, this charming 3-bedroom, 1-bath home offers a comfortable layout and convenient location. The home features both a spacious living room and a separate family room, providing plenty of space for relaxing, entertaining, or working from home. A dedicated laundry room with washer and dryer hookups adds everyday convenience, while the

  523 Oak Ave, Maitland, FL 32751
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  /2

  $595,000

  Sold May 05, 2026

  2466 Fieldingwood Rd, Maitland, FL 32751

  • 4 Beds
  • 2 Baths
  • 1,765 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Below List Price
  • $337/SF
  • 2 Days On Market

  Current Estimated Value $553,297

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

  2466 Fieldingwood Rd, Maitland, FL 32751
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  /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
• 

  

  /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
• 

  

  /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 $1892/mo12-Month+ Stay base rent: starts at $1892/moLanding's apartments at The Tiffany at

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

  /2

  $239,000

  Sold May 08, 2026

  602 Villa Cir Unit 543, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,256 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Below List Price
  • $190/SF
  • 49 Days On Market

  Current Estimated Value $245,485

  Last Listing Agent Odel Ximinies COLDWELL BANKER REALTY

  602 Villa Cir Unit 543, Maitland, FL 32751
• 

  /2

  Est $214,656

  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
• 

  

  /35

  $619,900

  $30K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,236 Sq Ft

  140 Wigwam Place, Maitland, FL 32751

  Virtually Staged. Tucked away on a cul-de-sac in beautiful Maitland, this 3-bedroom, 3-bath home with a bonus room offers space, comfort, and privacy on a generous 1/3-acre lot. With 2,236 square feet of living space and a 2-car garage, the home features an updated kitchen and upgraded bathrooms, blending modern touches with everyday functionality. Enjoy cozy evenings by the fireplace or relax in

  Blake Bolton LPT REALTY, LLC

  140 Wigwam Place, 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 $1892/mo12-Month+ Stay base rent: starts at $1892/moLanding's apartments at The Tiffany at

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

  /2

  $515,000

  Sold Nov 07, 2025

  2162 Lake Howell Preserve Ct, Maitland, FL 32751

  • 3 Beds
  • 3.5 Baths
  • 2,188 Sq Ft
  • Built 2021

  Last Sold Summary

  • 6% Below List Price
  • $235/SF
  • 27 Days On Market

  Last Listing Agent Mark Raumaker SERHANT

  2162 Lake Howell Preserve Ct, Maitland, FL 32751
• 

  /2

  Est $213,255

  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
• 

  

  /62

  $975,000

  $25K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 3,049 Sq Ft

  755 Woodside Rd, Maitland, FL 32751

  This is the one you've been waiting for- a SLEEK MODERN HOME, where EVERY MAJOR SYSTEM AND FINISH has been REPLACED, REFRESHED and ELEVATED to perfection and minutes from Winter Park without the WP price tag! 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 with 2 Car

  Diane Heiken EMPIRE NETWORK REALTY

  755 Woodside Rd, Maitland, FL 32751
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  /15

  $2,400 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,015 Sq Ft
  • House for Rent

  31 Bel Air St, Eatonville, FL 32751

  Step into comfort and convenience with this 3-bedroom, 1.5-bath home that offers room to live and relax. Featuring both a welcoming living room and a separate family room, this layout provides the perfect balance of gathering spaces and cozy retreats.The kitchen and common areas flow seamlessly, making everyday living easy and enjoyable. A dedicated laundry room with washer and dryer

  31 Bel Air St, Eatonville, FL 32751
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  /2

  $335,000

  Sold Oct 03, 2025

  180 N Lakewood Cir, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,050 Sq Ft
  • Built 1971

  Last Sold Summary

  • 22% Below List Price
  • $319/SF
  • 301 Days On Market

  Current Estimated Value $319,739

  Last Listing Agent Todd Norwood BESPOKE REAL ESTATE

  180 N Lakewood Cir, Maitland, FL 32751
• 

  

  /40

  Est $320,667

  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
• 

  

  /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
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  /13

  $1,575

  Total Monthly Price

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

  1408 Lake Shadow Cir Unit 1105, Maitland, FL 32751

  Beautiful 2-Bedroom Condo in Gated Community – Visconti West, MaitlandWelcome to your new home in one of Maitland’s most sought-after gated communities! This spacious and stylish 2-bedroom, 2-bathroom condo offers comfort, convenience, and access to top-notch amenities.Features:- Granite countertops in both kitchen and bathrooms- Two large bedrooms with walk-in

  1408 Lake Shadow Cir Unit 1105, Maitland, FL 32751
• 

  /2

  $1,350,000

  Sold Oct 01, 2025

  2047 Howell Branch Rd, Maitland, FL 32751

  • 4 Beds
  • 2 Baths
  • 2,960 Sq Ft
  • Built 1986

  Last Sold Summary

  • 10% Below List Price
  • $456/SF
  • 28 Days On Market

  Current Estimated Value $1,342,541

  Last Listing Agent Shelby Smith KELLY PRICE & COMPANY LLC

  2047 Howell Branch Rd, Maitland, FL 32751
• 

  

  /22

  Est $185,119

  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
• 

  

  /37

  $1,149,900

  Pending

  • 4 Beds
  • 4.5 Baths
  • 3,040 Sq Ft

  766 Terra Place, Maitland, FL 32751

  Under contract-accepting backup offers. Virtually Staged. Private Pool Retreat with Two Primary Suites in Terra Place. Nestled in Terra Place, one of Maitland’s best-kept-secret neighborhoods, where every street ends in a cul-de-sac and a community park is just steps away, this custom one-story pool home offers space, privacy, and functionality—with no mandatory HOA. Soaring cathedral ceilings,

  Chris Creegan CREEGAN GROUP

  766 Terra Place, Maitland, FL 32751
• 

  

  /3

  $1,375

  Total Monthly Price

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

  1125 Lake Shadow Cir Unit 5-101, Maitland, FL 32751

  Located in the Beautiful Gated Visconti condos in Maitland, FL. Clubhouse and pool amenities, work out room and more.This unit is 1st floor (no stairs) corner unit (More privacy).Washer and dryer included. Water and trash pick up included.No pets allowed.

  1125 Lake Shadow Cir Unit 5-101, Maitland, FL 32751
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  /2

  $960,000

  Sold Sep 02, 2025

  2106 Tuscarora Trail, Maitland, FL 32751

  • 4 Beds
  • 3 Baths
  • 2,949 Sq Ft
  • Built 1961

  Last Sold Summary

  • 2% Below List Price
  • $326/SF
  • 65 Days On Market

  Current Estimated Value $947,520

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY

  2106 Tuscarora Trail, Maitland, FL 32751
• 

  

  /34

  Est $265,021

  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

Showing Results 161 - 200, Page 5 of 18