Maitland, FL Homes

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  $199,995

  • 2 Beds
  • 2 Baths
  • 1,048 Sq Ft

  1100 Lake Shadow Cir Unit 2203, Maitland, FL 32751

  Welcome home to this beautifully renovated 2-bedroom, 2-bath first-floor condo offering 1,111 sq. ft. of comfortable, open-concept living. The home features a bright split floor plan, a newly updated kitchen with fresh ceramic tile flooring, and spacious living areas perfect for relaxing or entertaining. Enjoy plush carpet, new paint throughout, and ceramic tile in the kitchen and bathrooms for a

  Sangita Khatri BRIC REALTY LLC

  1100 Lake Shadow Cir Unit 2203, Maitland, FL 32751
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  /40

  $1,000,000 Sold May 09, 2025

  1606 The Oaks Dr, Maitland, FL 32751

  • 4 Beds
  • 3.5 Baths
  • 3,862 Sq Ft
  • Built 1979

  Last Sold Summary

  • 33% Below List Price
  • $259/SF
  • 68 Days On Market

  Current Estimated Value $1,050,576

  Last Listing Agent Cheryl Gray RIDER REALTY, LLC

  1606 The Oaks Dr, Maitland, FL 32751
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  /27

  Est $168,435 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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  /28

  $225,000

  • 2 Beds
  • 1.5 Baths
  • 1,353 Sq Ft

  1009 Grove St Unit 1009, Maitland, FL 32751

  This beautifully updated 2 bedroom, 1.5 bath condo in Maitland is located minutes from shops, restaurants and offers easy access to I-4!. The stylish kitchen features granite countertops, 42 inch cabinetry, built-in wine glass rack, stainless appliances, pass thru window, and a long breakfast bar. Updated half bath downstairs for convenience. Both spacious bedrooms are located upstairs and share

  Ingrid Livingston COLDWELL BANKER RESIDENTIAL RE

  1009 Grove St Unit 1009, 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 $573,161

  Last Listing Agent Teresa Parker PREMIER SOTHEBYS INT'L REALTY

  2595 Sweetwater Trail, Maitland, FL 32751
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  /38

  Est $307,148 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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  /42

  $285,000

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

  1618 Gulfview Dr Unit 417, Maitland, FL 32751

  One or more photo(s) has been virtually staged. Welcome to this exquisitely renovated home offering the best value in the maintenance-free community of Park Lake Grove! This stunning 3-bedroom, 3-bathroom property features 1,328 square feet of beautifully updated living space and a rear-facing, fully enclosed one-car garage. Every inch of this home has been thoughtfully renovated with quality and

  Wendy Aldana LLC NETWORTH REALTY OF ORLANDO, LLC

  1618 Gulfview Dr Unit 417, 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 $305,570

  Last Listing Agent andre visser HOME PRO REALTY CORP.

  1068 Hamlet Dr, Maitland, FL 32751
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  /43

  Est $290,163 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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  /51

  $595,000

  • 4 Beds
  • 2.5 Baths
  • 1,845 Sq Ft

  1024 Kewannee Trail, Maitland, FL 32751

  One or more photo(s) has been virtually staged. Welcome home to this well outfitted 4 Bed 2.5 Bath home in sought after Maitland. Tastefully upgraded home on a generous lot, with in ground pool. Great upgraded kitchen with custom cabinets for extra storage complemented with upgraded Stainless Appliances and granite counters. Thoughtful upgrades at every turn. Currently zoned for Winter Park HS.

  Patrick D'Agostino GLORY INTL. REAL ESTATE CO

  1024 Kewannee Trail, 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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  /2

  Est $193,749 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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  /39

  $540,000

  • 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

  $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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  /59

  Est $228,356 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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  /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

  $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 $265,112

  Last Listing Agent Ingrid Livingston COLDWELL BANKER RESIDENTIAL RE

  1152 Grove St Unit 185, Maitland, FL 32751
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  /28

  Est $161,719 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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  /8

  $2,995,000

  • Land
  • 0.42 Acre
  • $7,130,952 per Acre

  125 Whitecaps Cir, Maitland, FL 32751

  Wonderful lakefront lot opportunity to create a custom legacy estate on Lake Maitland, part of the prestigious Maitland-Winter Park Chain of Lakes. Lakefront lots are becoming more and more exceedingly rare, and this homesite is truly one of a kind. A very private setting, perfectly positioned on a quiet street, the property sets up well to be gated and offers sweeping southern lake views where

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  125 Whitecaps Cir, 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 $260,807

  Last Listing Agent Eric Soto TC ORLANDO HOMES LLC

  1615 Grove St Unit 545, Maitland, FL 32751
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  /10

  Est $226,609 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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  /77

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 2,110 Sq Ft

  1447 Caring Ct, Maitland, FL 32751

  Beautiful move-in ready home in the highly sought-after gated community of Montacino, located in the heart of Maitland. This single-story Mediterranean inspired home boasts three spacious bedrooms, including the grand Primary bedroom suite with its private spa-inspired bathroom with a jacuzzi tub, another inviting full bathroom, a convenient half bath, and a separate office or den great for

  Thomas Siciliano KELLER WILLIAMS HERITAGE REALTY

  1447 Caring Ct, 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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  /52

  Est $226,143 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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  /23

  $679,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,995 Sq Ft

  10 Minnehaha Cir, Maitland, FL 32751

  Welcome to this beautifully refined 4-bedroom, 3-bath POOL HOME in the highly sought-after Minnehaha Shores community of Maitland. Situated on a prominent corner lot with picturesque views of Minnehaha Park, this residence offers thoughtful enhancements, generous indoor–outdoor living, and exclusive neighborhood lake access to the Winter Park Chain of Lakes. Step inside to an airy, open layout

  Chris Creegan CREEGAN GROUP

  10 Minnehaha Cir, 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 $629,016

  Last Listing Agent Marina Munoz OUTLET REALTY

  2318 Mohawk Trail, Maitland, FL 32751
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  /41

  Est $224,268 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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  /29

  $219,900

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

  1460 Lake Shadow Cir Unit 7204, Maitland, FL 32751

  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 features a fully equipped kitchen with

  Jason Asa LPT REALTY, LLC

  1460 Lake Shadow Cir Unit 7204, 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 $741,375

  Last Listing Agent Ahmad Hassan COMPASS FLORIDA LLC

  2337 Worthington Rd, Maitland, FL 32751
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  /2

  Est $247,824 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

  $205,000

  • 2 Beds
  • 2 Baths
  • 1,048 Sq Ft

  1100 Lake Shadow Cir Unit 2206, Maitland, FL 32751

  Gated community of Visconti. Easy access to I4, beaches, downtown Orlando. Altamonte Springs. This community offers a resort style living. Valet trash pick up, water, trash, sewer, pest control included in hoa dues as well as building insurance. Community offers fitness, two pools on the lake. Basketball court, tennis courts, play ground.

  Didem Isik Widener PARK AVENUE REALTY LLC

  1100 Lake Shadow Cir Unit 2206, 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 $312,350

  Last Listing Agent David Weiss COLDWELL BANKER REALTY

  311 W Lake Faith Dr, Maitland, FL 32751
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  /37

  Est $271,406 Not Listed For Sale

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

  1460 Lake Shadow Cir Unit 7108, Maitland, FL 32751

  1460 Lake Shadow Cir Unit 7108, Maitland, FL 32751
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  /25

  $129,900

  • 1 Bed
  • 1 Bath
  • 550 Sq Ft

  2521 Caper Ln Unit 101, Maitland, FL 32751

  Welcome to this charming 1-bedroom, 1-bath first-floor condo in the heart of Maitland! Perfectly located just minutes from shopping, dining, and entertainment, this home offers both convenience and comfort. Step inside to find a bright living space with neutral tones and an open layout, ready for your personal touch. The kitchen features stainless steel appliances, ample cabinet space, and a

  Michael Rogers INNOVATIVE REALTY, LLC

  2521 Caper Ln Unit 101, 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

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  808 Ponca Trail, Maitland, FL 32751
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  /35

  Est $216,157 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,048 Sq Ft

  1475 Lake Shadow Cir Unit 6306, Maitland, FL 32751

  1475 Lake Shadow Cir Unit 6306, Maitland, FL 32751
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  /74

  $569,000

  • 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

  $390,000 Sold Nov 04, 2025

  1277 Blessing St, Maitland, FL 32751

  • 3 Beds
  • 2.5 Baths
  • 1,751 Sq Ft
  • Built 2006

  Last Sold Summary

  • 4% Below List Price
  • $223/SF
  • 119 Days On Market

  Last Listing Agent Denise LeHeup KELLER WILLIAMS WINTER PARK

  1277 Blessing St, Maitland, FL 32751
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  /2

  Est $212,641 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,048 Sq Ft

  1475 Lake Shadow Cir Unit 6305, Maitland, FL 32751

  1475 Lake Shadow Cir Unit 6305, Maitland, FL 32751
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  /15

  $450,000

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

  1100 S Orlando Ave Unit 208, Maitland, FL 32751

  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 I-4 and Maitland Blvd. Your association

  Jeff Crandall SHORESTONE PROPERTY GROUP

  1100 S Orlando Ave Unit 208, Maitland, FL 32751

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