Maitland, FL Homes

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  /27

  $499,990

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

  2065 Derbyshire Rd, Maitland, FL 32751

  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 heart of the home, showcasing sleek

  Ceila Morales EXP REALTY LLC

  2065 Derbyshire Rd, Maitland, FL 32751
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  /2

  $565,000 Sold Mar 27, 2025

  2595 Sweetwater Trail, Maitland, FL 32751

  • 4 Beds
  • 2.5 Baths
  • 2,208 Sq Ft
  • Built 1971

  Last Sold Summary

  • $256/SF
  • 10 Days On Market

  Current Estimated Value $566,957

  Last Listing Agent Teresa Parker PREMIER SOTHEBYS INT'L REALTY

  2595 Sweetwater Trail, Maitland, FL 32751
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  /2

  Est $296,285 Not Listed For Sale

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

  1000 Winderley Place Unit 240, Maitland, FL 32751

  1000 Winderley Place Unit 240, Maitland, FL 32751
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  /39

  $510,000

  • 3 Beds
  • 2 Baths
  • 1,798 Sq Ft

  1231 Sidcup Rd, Maitland, FL 32751

  Prepare to be captivated by this fully renovated gem located in the highly sought after English Estates neighborhood. Offering 1,798 square feet of meticulously designed living space, this three bedroom, two bathroom home blends timeless charm with modern luxury. Every inch has been thoughtfully updated, including a brand new air conditioning system, new thermostat, and a newer roof. The home

  Andrea Heck KELLER WILLIAMS TAMPA CENTRAL

  1231 Sidcup Rd, Maitland, FL 32751
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  /2

  $309,800 Sold Feb 27, 2025

  1068 Hamlet Dr, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,146 Sq Ft
  • Built 1994

  Last Sold Summary

  • 2% Below List Price
  • $270/SF
  • 117 Days On Market

  Current Estimated Value $305,661

  Last Listing Agent andre visser HOME PRO REALTY CORP.

  1068 Hamlet Dr, Maitland, FL 32751
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  /29

  Est $220,680 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,111 Sq Ft

  1408 Lake Shadow Cir Unit 1301, Maitland, FL 32751

  1408 Lake Shadow Cir Unit 1301, Maitland, FL 32751
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  /26

  $525,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,520 Sq Ft

  400 Boynton Rd, Maitland, FL 32751

  Special Opportunity in the heart of Maitland! Own a piece of history or build your dream home on this generous quarter acre lot that is just a five-minute walk from the Maitland Arts Center. The existing 3-bedroom, 2 bath home has all the character of a historical home, including gorgeous 6-panel doors, unique floor plan, and built-in details. Relish the extensive mature landscaping and block

  Lauren Fletcher WEICHERT REALTORS HALLMARK PROPERTIES

  400 Boynton Rd, Maitland, FL 32751
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  /2

  $540,000 Sold Jan 27, 2026

  2525 Native Ct, Maitland, FL 32751

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft
  • Built 1966

  Last Sold Summary

  • 14% Below List Price
  • $241/SF
  • 33 Days On Market

  Last Listing Agent Jennifer Johnson Perez REAL ESTATE PROS

  2525 Native Ct, Maitland, FL 32751
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  /27

  Est $167,403 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 746 Sq Ft

  1275 Lake Shadow Cir Unit 13112, Maitland, FL 32751

  1275 Lake Shadow Cir Unit 13112, Maitland, FL 32751
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  /14

  $2,875,000

  • Land
  • 0.42 Acre
  • $6,845,238 per Acre

  125 Whitecaps Cir, Maitland, FL 32751

  Wonderful lakefront lot opportunity to create a custom legacy estate on Lake Maitland, part of the Maitland-Winter Park Chain of Lakes. Lakefront homesites are becoming increasingly rare, and this offering is truly special. Tucked away on a quiet street, the property enjoys a very private setting with the ability to be gated, along with sweeping southern lake views that capture both sunrise and

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  125 Whitecaps Cir, Maitland, FL 32751
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  /2

  $490,000 Sold Dec 23, 2025

  515 W Faith Terrace, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 2,205 Sq Ft
  • Built 1956

  Last Sold Summary

  • 11% Below List Price
  • $222/SF
  • 75 Days On Market

  Last Listing Agent Chris Creegan CREEGAN GROUP

  515 W Faith Terrace, Maitland, FL 32751
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  /38

  Est $307,830 Not Listed For Sale

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

  1000 Winderley Place Unit 242, Maitland, FL 32751

  1000 Winderley Place Unit 242, Maitland, FL 32751
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  /29

  $199,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,243 Sq Ft

  1460 Lake Shadow Cir Unit 7204, Maitland, FL 32751

  Under contract-accepting backup offers. OWNER MOTIVATED! PRICED TO SELL!! Resort style living in this sought after gated community located near the Maitland Exchange. A rare find to have a 3 bedroom with Dual Master suites, 2 full baths located on the 2nd floor in Building 7 just steps away from the 2 Lakefront Pools, Fitness Room and a well appointed Clubhouse for special events. This unit

  Jason Asa LPT REALTY, LLC

  1460 Lake Shadow Cir Unit 7204, Maitland, FL 32751
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  /2

  $378,000 Sold Feb 21, 2025

  2201 Sunderland Rd, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,798 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $210/SF
  • 3 Days On Market

  Last Listing Agent Pam Tucker BETTER HOMES AND GARDENS REAL ESTATE MANN GLOBAL P

  2201 Sunderland Rd, Maitland, FL 32751
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  /43

  Est $278,468 Not Listed For Sale

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

  1000 Winderley Place Unit 229, Maitland, FL 32751

  1000 Winderley Place Unit 229, Maitland, FL 32751
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  /22

  $250,000

  • Land
  • 0.26 Acre
  • $961,538 per Acre

  1130 Mechanic St, Maitland, FL 32751

  This 0.26 acre cleared lot is ready for you to create the home of your dreams! Nestled among majestic oak trees, it provides a serene and private setting while maintaining easy access to everything you need. Enjoy the perfect blend of a peaceful, country-like atmosphere right in the heart of the city. Located less than a mile from Maitland Community Park, you'll have access to sports courts,

  Richard Palmano PALMANO GROUP RE BROKERAGE LLC

  1130 Mechanic St, Maitland, FL 32751
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  /2

  $253,000 Sold Aug 15, 2025

  1152 Grove St Unit 185, Maitland, FL 32751

  • 3 Beds
  • 3 Baths
  • 1,575 Sq Ft
  • Built 1979

  Last Sold Summary

  • 14% Below List Price
  • $161/SF
  • 86 Days On Market

  Current Estimated Value $260,519

  Last Listing Agent Ingrid Livingston COLDWELL BANKER RESIDENTIAL RE

  1152 Grove St Unit 185, Maitland, FL 32751
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  /2

  Est $192,633 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 898 Sq Ft

  1375 Lake Shadow Cir Unit 11107, Maitland, FL 32751

  1375 Lake Shadow Cir Unit 11107, Maitland, FL 32751
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  /74

  $559,000

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

  1470 Winston Rd, Maitland, FL 32751

  Seller is willing to assist with buyer closing costs or assist with interest rate buy down. This stunning 4-bedroom, 2-bathroom home has been completely reimagined from the ground up, offering flawless design, and premium finishes. Situated on a generous lot in a sought-after Maitland neighborhood, this home combines comfort, function, and style in every detail. Step inside to an inviting

  Ricardo Adames LA ROSA REALTY CW PROPERTIES L

  1470 Winston Rd, Maitland, FL 32751
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  /2

  $263,500 Sold Apr 18, 2025

  1615 Grove St Unit 545, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,087 Sq Ft
  • Built 1979

  Last Sold Summary

  • 1% Below List Price
  • $242/SF
  • 17 Days On Market

  Current Estimated Value $257,257

  Last Listing Agent Eric Soto TC ORLANDO HOMES LLC

  1615 Grove St Unit 545, Maitland, FL 32751
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  /59

  Est $224,054 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,111 Sq Ft

  1420 Lake Shadow Cir Unit 9208, Maitland, FL 32751

  1420 Lake Shadow Cir Unit 9208, Maitland, FL 32751
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  /15

  $450,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft

  1100 S Orlando Ave Unit 208, Maitland, FL 32751

  Under contract-accepting backup offers. Breathtaking views of Lake Maitland, the largest lake of the desirable Winter Park Chain of Lakes. Enjoy sunrises across the lake from the privacy of your balcony overlooking the pool. This 2-bedroom, 2-bath condo within West Cove Condos is centrally located in close proximity to a variety of restaurants, Lake Lily Park, Enzian Theater and easy access to

  Jeff Crandall SHORESTONE PROPERTY GROUP

  1100 S Orlando Ave Unit 208, Maitland, FL 32751
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  /2

  $191,000 Sold Aug 15, 2025

  39 S College Ave, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,702 Sq Ft
  • Built 1962

  Last Sold Summary

  • 20% Below List Price
  • $112/SF
  • 45 Days On Market

  Current Estimated Value $196,268

  Last Listing Agent Brenden Rando NEXTHOME NEIGHBORHOOD REALTY

  39 S College Ave, Maitland, FL 32751
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  /28

  Est $162,839 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 672 Sq Ft

  1400 Lake Shadow Cir Unit 10205, Maitland, FL 32751

  1400 Lake Shadow Cir Unit 10205, Maitland, FL 32751
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  /28

  $418,500 Pending

  • 4 Beds
  • 2 Baths
  • 1,664 Sq Ft

  1913 Poinsetta Ln, Maitland, FL 32751

  Motivated Seller | Renovated Pool Home in Prime Maitland Location This solid concrete block 4-bedroom, 2-bath residence has been fully refreshed inside and is truly move-in ready. Ideally situated just 1⁄2 mile from English Estates Elementary and minutes from Kewannee Park, shopping, dining, scenic trails, I-4, and the airport, the location gives both convenience and neighborhood charm. The

  Jonathan Minerick HOMECOIN.COM

  1913 Poinsetta Ln, Maitland, FL 32751
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  /2

  $235,000 Sold Aug 01, 2025

  6 Barnard Ct, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,521 Sq Ft
  • Built 1956

  Last Sold Summary

  • 26% Below List Price
  • $155/SF
  • 133 Days On Market

  Last Listing Agent Brian Opre THE REAL ESTATE PRINCIPLE, INC

  6 Barnard Ct, Maitland, FL 32751
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  /10

  Est $219,442 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,111 Sq Ft

  1420 Lake Shadow Cir Unit 9307, Maitland, FL 32751

  1420 Lake Shadow Cir Unit 9307, Maitland, FL 32751
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  /16

  $169,900 Pending

  • 2 Beds
  • 1 Bath
  • 520 Sq Ft

  2031 Warrens Ave, Maitland, FL 32751

  Ready for a weekend project with big upside? With a little love and light renovations, 2031 Warrens Avenue can shine as Maitland’s next tiny-home success story. This 2-bed, 1-bath cottage (approx. 560 sq ft) already boasts a bright, open living-kitchen core and fresh interior paint; add new flooring, modern fixtures, and your own style to unlock instant equity. The ~0.10-acre lot—rare at this

  Brenden Rando NEXTHOME NEIGHBORHOOD REALTY

  2031 Warrens Ave, Maitland, FL 32751
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  /2

  $630,000 Sold Jul 18, 2025

  2318 Mohawk Trail, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,736 Sq Ft
  • Built 1963

  Last Sold Summary

  • 5% Below List Price
  • $363/SF
  • 34 Days On Market

  Current Estimated Value $629,825

  Last Listing Agent Marina Munoz OUTLET REALTY

  2318 Mohawk Trail, Maitland, FL 32751
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  /52

  Est $221,041 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,111 Sq Ft

  1420 Lake Shadow Cir Unit 9201, Maitland, FL 32751

  1420 Lake Shadow Cir Unit 9201, Maitland, FL 32751
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  /39

  $595,000 Open Sun 2PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 1,734 Sq Ft

  225 Quayside Cir, Maitland, FL 32751

  Discover the perfect blend of style and location in this beautifully updated 3-bedroom, 2.5-bathroom townhome in the sought-after Moorings community. With 1,734 square feet of thoughtfully designed living space, this residence offers a bright, open floor plan enhanced by vaulted ceilings and an abundance of natural light.The heart of the home is the stunning kitchen, showcasing white

  Kelly Price KELLY PRICE & COMPANY LLC

  225 Quayside Cir, Maitland, FL 32751
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  /2

  $228,000 Sold Feb 04, 2026

  1601 Grove St Unit 552, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,087 Sq Ft
  • Built 1979

  Last Sold Summary

  • 9% Below List Price
  • $210/SF
  • 92 Days On Market

  Last Listing Agent Chris Creegan CREEGAN GROUP

  1601 Grove St Unit 552, Maitland, FL 32751
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  /22

  Est $218,838 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,111 Sq Ft

  1440 Lake Shadow Cir Unit 8302, Maitland, FL 32751

  1440 Lake Shadow Cir Unit 8302, Maitland, FL 32751
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  /28

  $695,000

  • 2 Beds
  • 2 Baths
  • 1,203 Sq Ft

  204 Quayside Cir Unit 202, Maitland, FL 32751

  Elegant lakefront on the shores of Lake Maitland! Experience timeless refinement in this exquisitely renovated lakefront condominium, where bespoke craftmanship meets modern luxury. Every detail has been thoughtfully curated - from the custom millworker and intricate moldings to the tailored built-ins that evoke charm of a grand London flat. Light filled living spaces open to serene lake views,

  Nicole Seybold FANNIE HILLMAN & ASSOCIATES

  204 Quayside Cir Unit 202, Maitland, FL 32751
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  /2

  $750,000 Sold Jul 02, 2025

  2337 Worthington Rd, Maitland, FL 32751

  • 4 Beds
  • 2.5 Baths
  • 2,050 Sq Ft
  • Built 1968

  Last Sold Summary

  • 21% Below List Price
  • $366/SF
  • 103 Days On Market

  Current Estimated Value $738,636

  Last Listing Agent Ahmad Hassan COMPASS FLORIDA LLC

  2337 Worthington Rd, Maitland, FL 32751
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  /41

  Est $216,747 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,111 Sq Ft

  1440 Lake Shadow Cir Unit 8207, Maitland, FL 32751

  1440 Lake Shadow Cir Unit 8207, Maitland, FL 32751
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  /54

  $3,299,000

  • 5 Beds
  • 4.5 Baths
  • 4,819 Sq Ft

  350 Northwind Rd, Maitland, FL 32751

  Nestled within the gated 9-acre Lake Maitland Owl Preserve, this striking contemporary residence—crafted by acclaimed green builder E2 Homes offers a rare blend of architectural distinction, privacy, and natural beauty. Surrounded by protected conservation land, the home delivers a serene retreat just minutes from the vibrant lifestyle of Winter Park. Designed by internationally recognized

  Lianna D'Angelo SOTERA LIVING

  350 Northwind Rd, Maitland, FL 32751
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  /2

  $299,999 Sold May 01, 2025

  311 W Lake Faith Dr, Maitland, FL 32751

  • 3 Beds
  • 3 Baths
  • 1,860 Sq Ft
  • Built 1974

  Last Sold Summary

  • $161/SF
  • 26 Days On Market

  Current Estimated Value $308,436

  Last Listing Agent David Weiss COLDWELL BANKER REALTY

  311 W Lake Faith Dr, Maitland, FL 32751
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  /2

  Est $243,945 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,243 Sq Ft

  1460 Lake Shadow Cir Unit 7203, Maitland, FL 32751

  1460 Lake Shadow Cir Unit 7203, Maitland, FL 32751
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  /2

  $765,000 Sold Sep 30, 2025

  808 Ponca Trail, Maitland, FL 32751

  • 4 Beds
  • 3 Baths
  • 2,311 Sq Ft
  • Built 1962

  Last Sold Summary

  • $331/SF
  • 4 Days On Market

  Current Estimated Value $753,071

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  808 Ponca Trail, Maitland, FL 32751

Showing Results 401 - 440, Page 11 of 18