Maitland, FL Homes

• 

  

  /2

  $2,850,000

  Sold Sep 12, 2025

  640 Old Horatio Ave, Maitland, FL 32751

  • 5 Beds
  • 4 Baths
  • 4,042 Sq Ft
  • Built 2025

  Last Sold Summary

  • 17% Below List Price
  • $705/SF
  • 156 Days On Market

  Current Estimated Value $2,860,000

  Last Listing Agent Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

  640 Old Horatio Ave, Maitland, FL 32751
• 

  

  

  /34

  Est $419,606

  Not Listed For Sale

  1100 S Orlando Ave Unit 604, Maitland, FL 32751

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

  1100 S Orlando Ave Unit 604, Maitland, FL 32751

  Last Sold Summary

  • 11 Days On Market
• 

  

  

  /28

  $500,000

  $50K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,748 Sq Ft

  140 E Faith Terrace, Maitland, FL 32751

  One or more photo(s) has been virtually staged. NEW ROOF 2022 - NEW AC 2022 - NEW ELECTRICAL PANELS 2022 - REPLUMB 2022 - NEW SEPTIC 2023 - Seperate detached GUEST HOUSE offering built-in monthly income potential. Previously rented under market value at $900/month, the guesthouse is currently vacant and ready for a new tenant, a private space for adult children, or a comfortable in-law suite.

  Gregory Roberts LPT REALTY LLC

  140 E Faith Terrace, Maitland, FL 32751
• 

  

  /2

  $250,000

  Sold Aug 22, 2025

  20 People St, Maitland, FL 32751

  • Land
  • 25,264 Sq Ft
  • $431,034 per Acre

  Last Sold Summary

  • 10 Days On Market

  Current Estimated Value $248,496

  Last Listing Agent Julia Meffen FLORIDA HOMES & LOANS INC.

  20 People St, Maitland, FL 32751
• 

  

  /2

  Est $343,133

  Not Listed For Sale

  1000 S Orlando Ave Unit A24, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft
  • Built 1964

  1000 S Orlando Ave Unit A24, Maitland, FL 32751

  Last Sold Summary

  • 28 Days On Market
• 

  

  /34

  $490,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,870 Sq Ft

  1106 Charming St, Maitland, FL 32751

  Under contract-accepting backup offers. Welcome to this beautifully maintained lakefront townhome in a highly desirable gated community in Maitland with almost 1900 square feet of thoughtfully designed living space. This 3-bedroom, 2.5-bath residence combines comfort, functionality, and picturesque lake views. Enjoy serene views of Lake Charity from the charming front porch, formal dining room,

  Donna Bryant COLDWELL BANKER REALTY

  1106 Charming St, Maitland, FL 32751
• 

  /2

  $235,000

  Sold Aug 14, 2025

  1140 S Orlando Ave Unit K15, Maitland, FL 32751

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft
  • Built 1966

  Last Sold Summary

  • 24% Below List Price
  • $288/SF
  • 194 Days On Market

  Current Estimated Value $239,998

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1140 S Orlando Ave Unit K15, Maitland, FL 32751
• 

  /2

  Est $488,346

  Not Listed For Sale

  202 Quayside Cir Unit 201, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,203 Sq Ft
  • Built 1984

  202 Quayside Cir Unit 201, Maitland, FL 32751

  Last Sold Summary

  • 64 Days On Market
• 

  

  /33

  $415,000

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

  1327 Chipola Trail, Maitland, FL 32751

  Discover a beautifully transformed 4-bedroom, 2-bath Maitland gem, a turnkey showpiece that blends modern style, smart upgrades, and undeniable curb appeal. The home greets you with a fresh look, mature landscaping, manicured hedges, and a custom front deck with modern horizontal railing, creating a welcoming entry and the perfect spot to enjoy your morning coffee.Step inside to an open and

  Abbas Sultanali ALPHA EQUITY REALTY & MANAGEMENT INC

  1327 Chipola Trail, Maitland, FL 32751
• 

  /2

  $379,000

  Sold Dec 29, 2025

  518 Oak Ln, Maitland, FL 32751

  • 3 Beds
  • 3 Baths
  • 1,999 Sq Ft
  • Built 1957

  Last Sold Summary

  • 10% Below List Price
  • $190/SF
  • 21 Days On Market

  Current Estimated Value $391,922

  Last Listing Agent Sonia Dublis COLDWELL BANKER REALTY

  518 Oak Ln, Maitland, FL 32751
• 

  

  /39

  Est $441,174

  Not Listed For Sale

  1140 S Orlando Ave Unit K9, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,246 Sq Ft
  • Built 1966

  1140 S Orlando Ave Unit K9, Maitland, FL 32751

  Last Sold Summary

  • 0 Days On Market
• 

  

  /39

  $659,900

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

  1404 Caring Ct, Maitland, FL 32751

  "RARE OPPORTUNITY" MOVE-IN READY 3-BED, 2.5-BATH SINGLE FAMILY HOME IN THE "EXCLUSIVE GATED COMMUNITY OF ENCLAVE AT MAITLAND", FL 32751. Nestled within the highly sought-after & gated community of Enclave at Maitland, Single Family Homes rarely come on the market and this home offers a Luxury Interior Footprint that's a perfect balance of privacy, elegance, and convenience. Fully updated & loaded

  Joel Bornstein ROCK SPRINGS REALTY, LLC

  1404 Caring Ct, Maitland, FL 32751
• 

  /2

  $678,500

  Sold Jul 18, 2025

  1921 Geronimo Trail, Maitland, FL 32751

  • 4 Beds
  • 3 Baths
  • 2,167 Sq Ft
  • Built 1970

  Last Sold Summary

  • $313/SF
  • 4 Days On Market

  Current Estimated Value $696,750

  Last Listing Agent Kayla Mcclean COMPASS FLORIDA LLC

  1921 Geronimo Trail, Maitland, FL 32751
• 

  

  /50

  Est $340,487

  Not Listed For Sale

  1000 S Orlando Ave Unit A26, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft
  • Built 1964

  1000 S Orlando Ave Unit A26, Maitland, FL 32751

  Last Sold Summary

  • 64 Days On Market
• 

  

  /28

  $499,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,683 Sq Ft

  370 Sultana Ln, Maitland, FL 32751

  PRICE IMPROVEMENT: Welcome to 370 Sultana Lane, a fully renovated 3-bedroom, 2-bathroom home located in the highly desirable Druid Hills community of Maitland. With over $60,000 in thoughtful upgrades and paid off solar, this move-in-ready residence offers modern comfort without the hassle of future projects. Step inside to a fully reimagined open floor plan designed for both everyday living and

  Melissa Osborne EQUITYPRO LLC

  370 Sultana Ln, Maitland, FL 32751
• 

  /2

  $340,000

  Sold Jan 16, 2026

  2352 Sierra Ln, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,343 Sq Ft
  • Built 1984

  Last Sold Summary

  • $253/SF
  • 6 Days On Market

  Current Estimated Value $332,815

  Last Listing Agent Shirley Welch BHHS FLORIDA REALTY

  2352 Sierra Ln, Maitland, FL 32751
• 

  

  /31

  Est $377,401

  Not Listed For Sale

  1000 S Orlando Ave Unit A4, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft
  • Built 1964

  1000 S Orlando Ave Unit A4, Maitland, FL 32751

  Last Sold Summary

  • 19 Days On Market
• 

  

  /47

  $749,900

  Open Sat 1PM - 4PM $75K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,375 Sq Ft

  2040 Geronimo Trail, Maitland, FL 32751

  Virtually Staged. Set on one of the most sought-after streets in Dommerich, this completely renovated home combines the solid construction of a 1963 block home with thoughtful modern updates throughout. From the moment you arrive, the circular driveway, classic brick accents, and welcoming front porch set the tone. Inside, a bright foyer opens to beautiful solid maple wood floors and a light,

  Maria Van Warner FANNIE HILLMAN & ASSOCIATES

  2040 Geronimo Trail, Maitland, FL 32751
• 

  /2

  $410,000

  Sold Sep 05, 2025

  2132 Tortoise Shell Dr, Maitland, FL 32751

  • 4 Beds
  • 2 Baths
  • 1,809 Sq Ft
  • Built 1996

  Last Sold Summary

  • 4% Below List Price
  • $227/SF
  • 15 Days On Market

  Current Estimated Value $414,289

  Last Listing Agent Gale Milgrim KELLER WILLIAMS WINTER PARK

  2132 Tortoise Shell Dr, Maitland, FL 32751
• 

  

  /34

  Est $255,528

  Not Listed For Sale

  1140 S Orlando Ave Unit H12, Maitland, FL 32751

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft
  • Built 1966

  1140 S Orlando Ave Unit H12, Maitland, FL 32751

  Last Sold Summary

  • 4 Days On Market
• 

  

  /39

  $619,000

  $60K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,922 Sq Ft

  1750 Pocahontas Path, Maitland, FL 32751

  Set along a quiet, tree-lined street in Maitland, this 3 bedroom, 2 bathroom home with 1,922 square feet captures the essence of mid-century modern design with a fresh, updated edge. Clean lines, open flow, and a strong connection to the outdoors define the home from the moment you step inside. Major updates include the kitchen in 2019, bathrooms in 2021, Roof 2022, and HVAC in 2024. The living

  Brian Rotenberger COMPASS FLORIDA LLC

  1750 Pocahontas Path, Maitland, FL 32751
• 

  /2

  $1,035,000

  Sold Sep 30, 2025

  904 Brightwater Cir, Maitland, FL 32751

  • 4 Beds
  • 3.5 Baths
  • 3,099 Sq Ft
  • Built 1997

  Last Sold Summary

  • 1% Below List Price
  • $334/SF
  • 9 Days On Market

  Current Estimated Value $1,038,335

  Last Listing Agent Erin Baker FANNIE HILLMAN & ASSOCIATES

  904 Brightwater Cir, Maitland, FL 32751
• 

  

  /34

  Est $193,778

  Not Listed For Sale

  1140 S Orlando Ave Unit E3, Maitland, FL 32751

  • 1 Bed
  • 1 Bath
  • 612 Sq Ft
  • Built 1971

  1140 S Orlando Ave Unit E3, Maitland, FL 32751

  Last Sold Summary

  • 23 Days On Market
• 

  

  /25

  $199,000

  $11K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 898 Sq Ft

  1375 Lake Shadow Cir Unit 11103, Maitland, FL 32751

  Stunning fully renovated 2-bedroom, 1-bath condo featuring a complete top-to-bottom remodel completed in 2026, located in the highly desirable gated Visconti West community in Maitland. This move-in ready unit features luxury vinyl plank flooring throughout, a beautifully updated kitchen with modern soft-close cabinetry, sleek finishes, and stainless steel appliances, as well as a bright

  Margo Ford M2M REALTY

  1375 Lake Shadow Cir Unit 11103, Maitland, FL 32751
• 

  /2

  $398,400

  Sold May 21, 2026

  2113 Falkner Rd, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,708 Sq Ft
  • Built 1998

  Last Sold Summary

  • $233/SF
  • 5 Days On Market

  Current Estimated Value $397,208

  Last Listing Agent Heather Travis LOCAL LIVING REALTY GROUP

  2113 Falkner Rd, Maitland, FL 32751
• 

  

  /42

  Est $227,135

  Not Listed For Sale

  1140 S Orlando Ave Unit A14, Maitland, FL 32751

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft
  • Built 1964

  1140 S Orlando Ave Unit A14, Maitland, FL 32751

  Last Sold Summary

  • 139 Days On Market
• 

  

  /45

  $355,000

  • 4 Beds
  • 2 Baths
  • 1,707 Sq Ft

  2401 Legacy Lake Dr Unit 2401, Maitland, FL 32751

  All roads lead to Visconti East! Located in Maitland, bordering nearby scenic Winter Park (Park Ave./ Rollins College) this distinctive 3 story, 4 Bed/2.5 Bath townhome is situated directly off of I-4 and SR414, within 10 minutes to Downtown Orlando, Park Avenue, and close access to SR429, Winter Garden, and North Orlando. This home offers a one-of-a-kind floor plan with the entry foyer, hall

  Trace Christian, III COLDWELL BANKER REALTY

  2401 Legacy Lake Dr Unit 2401, Maitland, FL 32751
• 

  /2

  $321,500

  Sold Dec 19, 2025

  214 Cherrywood Dr, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,178 Sq Ft
  • Built 1958

  Last Sold Summary

  • 16% Below List Price
  • $273/SF
  • 288 Days On Market

  Current Estimated Value $321,118

  Last Listing Agent Karen Albright OPENDOOR BROKERAGE LLC

  214 Cherrywood Dr, Maitland, FL 32751
• 

  /2

  Est $316,303

  Not Listed For Sale

  210 Magnolia Rd Unit 110, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Built 1971

  210 Magnolia Rd Unit 110, Maitland, FL 32751

  Last Sold Summary

  • 9 Days On Market
• 

  

  /39

  $645,000

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,214 Sq Ft

  910 Gamewell Ave, Maitland, FL 32751

  Tucked away in the heart of Maitland, this thoughtfully updated three-bedroom, two bath residence blends everyday comfort with meaningful, modern upgrades. Freshly painted interior (June 2026) and a private spa pool WITH BRAND NEW POOL PUMP creates a serene outdoor retreat—perfect for unwinding or entertaining year-round in true Florida style. Inside, the home offers both function and peace of

  Sarah Tomlinson COMPASS FLORIDA LLC

  910 Gamewell Ave, Maitland, FL 32751
• 

  /2

  $385,000

  Sold Mar 31, 2026

  314 Banyan Dr, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,234 Sq Ft
  • Built 1972

  Last Sold Summary

  • 4% Below List Price
  • $312/SF
  • 122 Days On Market

  Current Estimated Value $379,363

  Last Listing Agent Ivanhoe Alvarez LOKATION

  314 Banyan Dr, Maitland, FL 32751
• 

  

  /8

  Est $256,041

  Not Listed For Sale

  1000 Winderley Place Unit 146, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 1985

  1000 Winderley Place Unit 146, Maitland, FL 32751

  Last Sold Summary

  • 27 Days On Market
• 

  

  /24

  $799,000

  $70K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,681 Sq Ft

  320 White Oak Cir, Maitland, FL 32751

  ENTERTAINING MAITLAND GROVE POOL HOME. Step inside to discover oversized rooms, including a spacious great room overlooking the covered lanai and swimming pool in a private setting perfect for gatherings. Back yard includes a vinyl privacy fence, Pool resurfaced with Pebble Tec. Patio and pool decking have pavers with plenty of room for extra lounging. Lots of Room for everyone, including lIving

  Susan Filebark OVERSTREET REAL ESTATE INC

  320 White Oak Cir, Maitland, FL 32751
• 

  /2

  $515,000

  Sold Oct 11, 2025

  1411 Glastonberry Rd, Maitland, FL 32751

  • 5 Beds
  • 2 Baths
  • 2,082 Sq Ft
  • Built 1965

  Last Sold Summary

  • 4% Below List Price
  • $247/SF
  • 17 Days On Market

  Current Estimated Value $511,985

  Last Listing Agent Patrick Urbainczyk P.A. KELLER WILLIAMS HERITAGE REALTY

  1411 Glastonberry Rd, Maitland, FL 32751
• 

  /2

  Est $304,212

  Not Listed For Sale

  1000 Winderley Place Unit 240, Maitland, FL 32751

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

  1000 Winderley Place Unit 240, Maitland, FL 32751
• 

  

  /97

  $850,000

  • 4 Beds
  • 2 Baths
  • 1,870 Sq Ft

  109 Kyle Dr, Maitland, FL 32751

  A tropical retreat in Minnehaha Shores with deeded lake access to the Winter Park Chain of Lakes. Tree-lined streets welcome you to this beautifully reimagined four-bedroom, two-bath split-plan home with coastal influences throughout. Formal living, dining and family spaces blend seamlessly together, creating great flexibility in layout. French doors line the back of the home and open to the

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  109 Kyle Dr, Maitland, FL 32751
• 

  /2

  $700,000

  Sold Mar 27, 2026

  814 N Thistle Ln, Maitland, FL 32751

  • 4 Beds
  • 2 Baths
  • 2,136 Sq Ft
  • Built 1960

  Last Sold Summary

  • $328/SF
  • 2 Days On Market

  Current Estimated Value $696,472

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

  814 N Thistle Ln, Maitland, FL 32751
• 

  /2

  Est $208,107

  Not Listed For Sale

  1100 Lake Shadow Cir Unit 2305, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,048 Sq Ft
  • Built 2000

  1100 Lake Shadow Cir Unit 2305, Maitland, FL 32751

  Last Sold Summary

  • 39 Days On Market
• 

  

  /43

  $379,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,674 Sq Ft

  1393 Benevolent St, Maitland, FL 32751

  This beautiful Maitland Florida town home feels like living in a gated resort! 3 bedrooms, 2 1/2 baths, plus garage and loaded with upgrades including hardwood floors on both levels, crown molding, tall wood cabinets, stone counters and so much more. Welcoming entry foyer with half bath, kitchen with island sink, large breakfast bar, stainless appliances, granite counters and custom backsplash.

  Daniel Rencher RENCHER REALTY GROUP

  1393 Benevolent St, Maitland, FL 32751
• 

  /2

  $359,706

  Sold Feb 10, 2026

  2464 Derbyshire Rd, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,860 Sq Ft
  • Built 1963

  Last Sold Summary

  • 16% Below List Price
  • $193/SF
  • 68 Days On Market

  Current Estimated Value $526,760

  Last Listing Agent Jennifer Vilayvong VYLLA HOME

  2464 Derbyshire Rd, Maitland, FL 32751

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