Maitland, FL Homes

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  /2

  $525,000

  Sold Sep 18, 2025

  503 Lake Shore Dr, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 2,054 Sq Ft
  • Built 1959

  Last Sold Summary

  • $256/SF
  • 17 Days On Market

  Current Estimated Value $534,627

  Last Listing Agent Tanya McDonnell RE/MAX TOWN & COUNTRY REALTY

  503 Lake Shore Dr, Maitland, FL 32751
• 

  

  

  /40

  Est $767,266

  Not Listed For Sale

  21 Minnehaha Cir, Maitland, FL 32751

  • 5 Beds
  • 2 Baths
  • 2,371 Sq Ft
  • Built 1961

  21 Minnehaha Cir, Maitland, FL 32751

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Taylor Paris FLORIDA HOMES REALTY & MORTGAGE
• 

  

  

  /19

  $959,000

  $38K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,470 Sq Ft

  1889 Berkeley Ct, Maitland, FL 32751

  Tucked at the end of a quiet cul-de-sac beneath a canopy of mature oaks, this beautifully maintained Maitland home offers space, privacy, and thoughtful updates throughout — all within a top school zone just minutes from Winter Park and downtown Orlando. A paver driveway winds through lush, established landscaping to a covered entry framed by an arched transom window, with a tile roof crowning

  Matt Merdian MERDIAN REALTY LLC

  1889 Berkeley Ct, Maitland, FL 32751
• 

  

  /2

  $251,500

  Sold Oct 28, 2025

  1140 S Orlando Ave Unit F9, Maitland, FL 32751

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft
  • Built 1969

  Last Sold Summary

  • 1% Above List Price
  • $308/SF
  • 2 Days On Market

  Current Estimated Value $253,204

  Last Listing Agent Allie George CORCORAN PREMIER REALTY

  1140 S Orlando Ave Unit F9, Maitland, FL 32751
• 

  

  

  /52

  Not Listed For Sale

  3102 Legacy Lake Dr, Maitland, FL 32751

  • 4 Beds
  • 2 Baths
  • 1,707 Sq Ft
  • Built 2000

  3102 Legacy Lake Dr, Maitland, FL 32751

  Last Sold Summary

  • 76 Days On Market

  Last Listing Agent Matthew Matin CLOCK TOWER REALTY
• 

  

  /21

  $1,798,999

  New Construction Pending

  • 5 Beds
  • 4.5 Baths
  • 3,203 Sq Ft

  105 Tangelo Ct, Maitland, FL 32751

  Under contract-accepting backup offers. Under Construction. A masterpiece of luxury design by LUIH Luxury Homes, perfectly positioned in the prestigious neighborhood of Hollieanna Shores. As you arrive, a striking façade with an elegant arched entryway sets an unforgettable tone. Beyond the front door, soaring ceilings and designer finishes frame an expansive living room where glass sliders

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  105 Tangelo Ct, Maitland, FL 32751
• 

  /2

  $985,000

  Sold Jun 25, 2026

  400 W Trotters Dr, Maitland, FL 32751

  • 4 Beds
  • 4 Baths
  • 3,397 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Below List Price
  • $290/SF
  • 8 Days On Market

  Current Estimated Value $980,868

  Last Listing Agent Mark Adams KELLER WILLIAMS REALTY AT THE PARKS

  400 W Trotters Dr, Maitland, FL 32751
• 

  

  /18

  Est $251,123

  Not Listed For Sale

  1140 S Orlando Ave Unit I16, Maitland, FL 32751

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft
  • Built 1971

  1140 S Orlando Ave Unit I16, Maitland, FL 32751

  Last Sold Summary

  • 70 Days On Market

  Last Listing Agent Desi Wehrs OPENDOOR BROKERAGE LLC
• 

  

  /18

  $235,000

  $24K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,496 Sq Ft

  916 Park Lake Cir Unit 34, Maitland, FL 32751

  **Listing price is seller's bottom line, he won't accept anything lower than asking** Gorgeous 3-bedroom, 3-bath, two-story townhome available now! This move-in-ready home features an updated kitchen with all appliances included, a convenient mudroom with washer and dryer hookups, fresh interior paint, and luxury vinyl plank (LVP) flooring throughout. Each spacious bedroom offers its own private

  Samantha Hafner DON ASHER & ASSOCIATES, INC.

  916 Park Lake Cir Unit 34, Maitland, FL 32751
• 

  /2

  $350,000

  Sold Aug 21, 2026

  501 Fitzgerald Dr, Maitland, FL 32751

  • 4 Beds
  • 2 Baths
  • 1,640 Sq Ft
  • Built 1967

  Last Sold Summary

  • 1% Above List Price
  • $213/SF
  • 4 Days On Market

  Current Estimated Value $316,158

  Last Listing Agent Joaquim Haynes JASON MITCHELL REAL ESTATE FLO

  501 Fitzgerald Dr, Maitland, FL 32751
• 

  /2

  Est $326,430

  Not Listed For Sale

  1140 S Orlando Ave Unit D1, Maitland, FL 32751

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

  1140 S Orlando Ave Unit D1, Maitland, FL 32751

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC
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  /36

  $1,150,000

  $100K PRICE DROP Under Contract

  • 4 Beds
  • 4 Baths
  • 3,902 Sq Ft

  873 Cranes Ct, Maitland, FL 32751

  Under contract-accepting backup offers. Now offered below recent appraised value, this exceptional residence combines luxury, location, and outstanding value in one of Maitland's most sought-after enclaves.Pride of ownership shines throughout this beautifully maintained original-owner home tucked away on a quiet cul-de-sac in the gated community of Sybelia Cove. Offering 4 bedrooms, 4

  Chris Creegan CREEGAN GROUP

  873 Cranes Ct, 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 $398,519

  Last Listing Agent Sonia Dublis COLDWELL BANKER REALTY

  518 Oak Ln, Maitland, FL 32751
• 

  /2

  Est $271,999

  Not Listed For Sale

  1140 S Orlando Ave Unit F3, Maitland, FL 32751

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft
  • Built 1969

  1140 S Orlando Ave Unit F3, Maitland, FL 32751

  Last Sold Summary

  • 49 Days On Market

  Last Listing Agent Angela Carney CORCORAN PREMIER REALTY
• 

  

  /16

  $355,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,351 Sq Ft

  1982 Water Ln, Maitland, FL 32751

  Beautifully updated 3-bedroom, 2-bath home in Maitland, conveniently located approximately 10 minutes from Park Avenue. Major improvements include hurricane-impact windows and a new roof in 2021, an updated kitchen with granite countertops in 2022, new tile flooring in 2023, a new A/C system and ductwork installed in August 2025, and new appliances in 2026. The home features a comfortable open

  Marledy Tabares COLDWELL BANKER REALTY

  1982 Water Ln, Maitland, FL 32751
• 

  /2

  $1,065,000

  Sold Jul 29, 2026

  766 Terra Place, Maitland, FL 32751

  • 4 Beds
  • 4.5 Baths
  • 3,040 Sq Ft
  • Built 1986

  Last Sold Summary

  • 7% Below List Price
  • $350/SF
  • 16 Days On Market

  Current Estimated Value $1,140,943

  Last Listing Agent Chris Creegan CREEGAN GROUP

  766 Terra Place, Maitland, FL 32751
• 

  /2

  Est $426,824

  Not Listed For Sale

  206 Quayside Cir Unit 504, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,270 Sq Ft
  • Built 1985

  206 Quayside Cir Unit 504, Maitland, FL 32751

  Last Sold Summary

  • 101 Days On Market

  Last Listing Agent Dee Morgan KELLY PRICE & COMPANY LLC
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  /44

  $595,000

  $35K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,975 Sq Ft

  741 Brookside Rd, Maitland, FL 32751

  Welcome to 741 Brookside Road in the heart of Maitland! This beautifully updated 4-bedroom, 2-bath pool home offers the perfect blend of modern upgrades, spacious living, and an unbeatable location. No expense was spared during the home's extensive renovations, creating a truly move-in-ready property that combines quality craftsmanship with timeless style.The recently remodeled kitchen is

  Jacob Hara TRANSCEND REALTY

  741 Brookside Rd, 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 $332,680

  Last Listing Agent Shirley Welch BHHS FLORIDA REALTY

  2352 Sierra Ln, Maitland, FL 32751
• 

  /2

  Est $204,271

  Not Listed For Sale

  1140 S Orlando Ave Unit A3, Maitland, FL 32751

  • 1 Bed
  • 1 Bath
  • 612 Sq Ft
  • Built 1964

  1140 S Orlando Ave Unit A3, Maitland, FL 32751

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Miriam Furey EXP REALTY LLC
• 

  

  /21

  $239,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  444 Banyon Tree Cir Unit 202, Maitland, FL 32751

  Beautifully well-maintained 3 bedroom, 2 bathroom condo located in the desirable Maitland area. This second floor unit features an updated kitchen, laminate flooring throughout, and an ope-concept layout that offers abundant natural light, including a bright and inviting porch space. The spacious primary-suite includes two walk-in closets. The communit offers a playground, fitness center,

  Lidia Gloria THE KEYES COMPANY

  444 Banyon Tree Cir Unit 202, 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 $1,049,768

  Last Listing Agent Erin Baker FANNIE HILLMAN & ASSOCIATES

  904 Brightwater Cir, Maitland, FL 32751
• 

  /2

  Est $403,958

  Not Listed For Sale

  1100 S Orlando Ave Unit 308, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1973

  1100 S Orlando Ave Unit 308, Maitland, FL 32751

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Alex Vastardis COLDWELL BANKER REALTY
• 

  

  /25

  $188,900

  $7K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 612 Sq Ft

  1140 S Orlando Ave Unit E11, Maitland, FL 32751

  LAKE ACCESS LIVING in one of Central Florida's most desirable locations! Welcome to 1140 S. Orlando Ave E11, a move in ready condo ideally located on the Winter Park and Maitland border in the sought after Lake Maitland Terrace community. Enjoy private access to Lake Maitland, part of the prestigious Winter Park Chain of Lakes, where you can spend your days paddle boarding, kayaking, boating,

  Abby Green IAD REAL ESTATE

  1140 S Orlando Ave Unit E11, 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 $399,510

  Last Listing Agent Heather Travis LOCAL LIVING REALTY GROUP

  2113 Falkner Rd, Maitland, FL 32751
• 

  

  /59

  Est $240,152

  Not Listed For Sale

  1140 S Orlando Ave Unit E14, Maitland, FL 32751

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft
  • Built 1971

  1140 S Orlando Ave Unit E14, Maitland, FL 32751

  Last Sold Summary

  • 59 Days On Market

  Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC
• 

  

  /25

  $340,000

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

  2362 Sierra Ln, Maitland, FL 32751

  Welcome to this beautifully maintained 3-bedroom, 2-bathroom condo with private garage in the desirable Sierra Condominium Association, offering a comfortable split-bedroom floor plan, exceptional curb appeal, and a serene outdoor setting. The meticulously maintained landscaping features a stunning bougainvillea plant, adding vibrant color and charm to the home's inviting exterior.Inside,

  Blake Safford SAFFORD REAL ESTATE LLC

  2362 Sierra Ln, 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 $326,802

  Last Listing Agent Karen Albright OPENDOOR BROKERAGE LLC

  214 Cherrywood Dr, Maitland, FL 32751
• 

  /2

  Est $277,677

  Not Listed For Sale

  1140 S Orlando Ave Unit B8, Maitland, FL 32751

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft
  • Built 1964

  1140 S Orlando Ave Unit B8, Maitland, FL 32751

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Vince Indiveri LIVE FLORIDA NOW LLC
• 

  

  /52

  $715,000

  $30K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,242 Sq Ft

  550 Arapaho Trail, Maitland, FL 32751

  This charming 4-bedroom, 3-bath home is in sought-after Dommerich Estates, one of the area’s most desirable neighborhoods. Designed for comfort, style, and everyday living, the home features a unique open floor plan with vaulted ceilings, a warm wood-burning fireplace, and an updated kitchen with solid wood cabinetry and granite countertops. Fresh interior and exterior paint, an oversized garage

  Shirley Welch BHHS FLORIDA REALTY

  550 Arapaho Trail, 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 $381,982

  Last Listing Agent Ivanhoe Alvarez LOKATION

  314 Banyan Dr, Maitland, FL 32751
• 

  /2

  Est $461,995

  Not Listed For Sale

  1100 S Orlando Ave Unit 301, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1973

  1100 S Orlando Ave Unit 301, Maitland, FL 32751

  Last Sold Summary

  • 129 Days On Market

  Last Listing Agent Renato Braga ON ME REALTY
• 

  

  /28

  $495,000

  $55K PRICE DROP Under Contract

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

  140 E Faith Terrace, Maitland, FL 32751

  Under contract-accepting backup offers. 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

  Gregory Roberts LPT REALTY LLC

  140 E Faith Terrace, 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 $514,750

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

  1411 Glastonberry Rd, Maitland, FL 32751
• 

  

  /48

  Est $479,363

  Not Listed For Sale

  1100 S Orlando Ave Unit 802, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,118 Sq Ft
  • Built 1973

  1100 S Orlando Ave Unit 802, Maitland, FL 32751

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Julie Bombardo PREMIER SOTHEBY'S INTL. REALTY
• 

  

  /34

  $619,900

  $40K PRICE DROP

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

  1404 Caring Ct, Maitland, FL 32751

  "NEW PRICE" ON THIS 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 private 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 with

  Joel Bornstein ROCK SPRINGS REALTY, LLC

  1404 Caring Ct, 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 $700,662

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

  814 N Thistle Ln, Maitland, FL 32751
• 

  

  /26

  Est $347,628

  Not Listed For Sale

  1000 S Orlando Ave Unit B33, Maitland, FL 32751

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

  1000 S Orlando Ave Unit B33, Maitland, FL 32751

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Amanda Wood RE/MAX EXCLUSIVE COLLECTION
• 

  

  /50

  $409,000

  $60K PRICE DROP Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,596 Sq Ft

  499 Julian Ln, Maitland, FL 32751

  Under contract-accepting backup offers. Location, Location, Location. Welcome to your new home in Maitland! This conviently located gated community home is a charming dwelling place featuring a cozy fireplace to uplift the ambiance of your living space. The home benefits from a tasteful neutral color paint scheme throughout, providing a welcoming canvas for your interior design aspirations. The

  Charles Munk SAND DOLLAR REALTY GROUP INC

  499 Julian Ln, Maitland, FL 32751
• 

  /2

  $415,000

  Sold Jun 30, 2026

  2154 Fennell St, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,642 Sq Ft
  • Built 1997

  Last Sold Summary

  • 3% Below List Price
  • $253/SF
  • 19 Days On Market

  Current Estimated Value $417,523

  Last Listing Agent Barrett Espinola PARK PLACE REALTY ASSOCIATES

  2154 Fennell St, Maitland, FL 32751

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