Maitland, FL Homes

• 

  

  /2

  $395,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,822 Sq Ft

  2155 Fennell St, Maitland, FL 32751

  Back to Market -This is a three-bedroom two-bathroom pool house well located that needs some tender love and care (TLC). This is an opportunity to exert the buyer’s creativity to update it. Great neighborhood, low HOA, close to Geminis sport and health facilities, Seminole Community College, the I-4, 15 minutes away from downtown Orlando, main grocery chains in less than two miles. Make your

  Benjamin Urrutia CHARLES RUTENBERG REALTY ORLANDO

  2155 Fennell St, Maitland, FL 32751
• 

  

  /2

  $689,000 Sold Sep 10, 2025

  1850 Geronimo Trail, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,736 Sq Ft
  • Built 1959

  Last Sold Summary

  • 7% Below List Price
  • $397/SF
  • 42 Days On Market

  Current Estimated Value $678,263

  Last Listing Agent Bobby Livera BALDWIN PARK REALTY LLC

  1850 Geronimo Trail, Maitland, FL 32751
• 

  

  

  /21

  Est $216,701 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,612 Sq Ft

  428 Banyon Tree Cir Unit 102, Maitland, FL 32751

  428 Banyon Tree Cir Unit 102, Maitland, FL 32751
• 

  

  

  /55

  $1,300,000

  • 4 Beds
  • 2.5 Baths
  • 2,116 Sq Ft

  1421 Sunnyside Dr, Maitland, FL 32751

  Welcome to 1421 Sunnyside Drive in Maitland, a beautifully maintained home where timeless design meets modern luxury. This 4-bedroom, 2.5-bath corner lot residence with a pool has a thoughtfully designed indoor and outdoor living space. Its location provides quick access to top-rated schools, boutique shopping, and local dining in one of the most desirable neighborhoods in the Maitland and Winter

  Amanda Binns STRICKLAND REALTY GROUP INC

  1421 Sunnyside Dr, Maitland, FL 32751
• 

  

  /2

  $595,000 Sold Feb 24, 2025

  1415 Caring Ct, Maitland, FL 32751

  • 3 Beds
  • 2.5 Baths
  • 2,110 Sq Ft
  • Built 2006

  Last Sold Summary

  • 6% Below List Price
  • $282/SF
  • 39 Days On Market

  Current Estimated Value $598,925

  Last Listing Agent Donna Bryant COLDWELL BANKER RESIDENTIAL RE

  1415 Caring Ct, Maitland, FL 32751
• 

  

  /40

  Est $784,878 Not Listed For Sale

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

  21 Minnehaha Cir, Maitland, FL 32751

  21 Minnehaha Cir, Maitland, FL 32751
• 

  

  /33

  $270,000

  • 3 Beds
  • 2.5 Baths
  • 1,583 Sq Ft

  2824 Shadow View Cir, Maitland, FL 32751

  VISCONTI - It doesn't feel like a "home" - you'll feel like you're checking into a RESORT! This gated, spacious three-story condominium offers an oversized double car garage. Venture upstairs to an open concept layout for living-kitchen-dining area. This home has been updated with all NEW wood floors, freshly painted with lovely crown and base molding and ALL new fans. The kitchen has ALL new

  Susan Taliaferro COLDWELL BANKER RESIDENTIAL RE

  2824 Shadow View Cir, Maitland, FL 32751
• 

  /2

  $800,000 Sold May 22, 2025

  2031 Dyan Way, Maitland, FL 32751

  • 4 Beds
  • 2 Baths
  • 2,213 Sq Ft
  • Built 1970

  Last Sold Summary

  • $362/SF

  Current Estimated Value $785,014

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  2031 Dyan Way, Maitland, FL 32751
• 

  

  /52

  Not Listed For Sale

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

  3102 Legacy Lake Dr, Maitland, FL 32751

  3102 Legacy Lake Dr, Maitland, FL 32751
• 

  

  /20

  $135,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,206 Sq Ft

  420 Banyon Tree Cir Unit 102, Maitland, FL 32751

  Under contract-accepting backup offers. Discover your dream condo in the tranquil Carrington Park neighborhood of Maitland! This charming 2-bedroom, 2-bathroom residence is perfect as your smart investment. Enjoy an open living area, a spacious Owner's Suite with an ensuite bathroom, and a generous closet. The community offers fantastic amenities, including a lovely pool, gym, and playground,

  Gregorio Henriques CENTURY 21 CARIOTI

  420 Banyon Tree Cir Unit 102, Maitland, FL 32751
• 

  /2

  $510,000 Sold Feb 10, 2025

  1450 Ridgewood Ave, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,549 Sq Ft
  • Built 1950

  Last Sold Summary

  • 34% Below List Price
  • $329/SF
  • 76 Days On Market

  Current Estimated Value $534,658

  Last Listing Agent Ashley Swindell DIBS REALTY, LLC

  1450 Ridgewood Ave, Maitland, FL 32751
• 

  

  /18

  Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft

  1140 S Orlando Ave Unit I16, Maitland, FL 32751

  1140 S Orlando Ave Unit I16, Maitland, FL 32751
• 

  

  /57

  $10,950,000

  • 5 Beds
  • 8 Baths
  • 8,174 Sq Ft

  1640 E Adams Dr, Maitland, FL 32751

  Behind private gates along the shores of Lake Maitland, this elegant Mizner-style Mediterranean estate offers an extraordinary opportunity to own a timeless lakefront masterpiece on the Winter Park Chain of Lakes. Encompassing approximately two acres of meticulously manicured grounds framed by soaring palms and mature live oaks, this exceptional property blends classic architecture with

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1640 E Adams Dr, Maitland, FL 32751
• 

  /2

  $410,000 Sold Jul 18, 2025

  326 Banyan Dr, Maitland, FL 32751

  • 4 Beds
  • 3 Baths
  • 2,538 Sq Ft
  • Built 1960

  Last Sold Summary

  • 22% Below List Price
  • $162/SF
  • 476 Days On Market

  Current Estimated Value $443,570

  Last Listing Agent Karen Albright OPENDOOR BROKERAGE LLC

  326 Banyan Dr, Maitland, FL 32751
• 

  

  /50

  Est $657,806 Not Listed For Sale

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

  206 Quayside Cir Unit 203, Maitland, FL 32751

  206 Quayside Cir Unit 203, Maitland, FL 32751
• 

  

  /23

  $699,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft

  1655 Sunnyside Dr, Maitland, FL 32751

  Under contract-accepting backup offers. Welcome to 1655 Sunnyside Drive, a beautifully charming home nestled on a picturesque corner lot in the heart of Maitland. Set on classic brick-lined roads, this 3-bedroom, 2-bathroom residence offers 1,418 square feet of thoughtfully designed living space filled with character and warmth. From the moment you arrive, you'll notice the inviting curb appeal,

  Joseph Sipp KELLER WILLIAMS WINTER PARK

  1655 Sunnyside Dr, Maitland, FL 32751
• 

  /2

  $221,647 Sold Sep 23, 2025

  802 Park Lake Cir Unit 2, Maitland, FL 32751

  • 2 Beds
  • 2.5 Baths
  • 1,432 Sq Ft
  • Built 1972

  Last Sold Summary

  • 18% Below List Price
  • $155/SF
  • 119 Days On Market

  Current Estimated Value $223,048

  Last Listing Agent Tom Graves FUN HOMES

  802 Park Lake Cir Unit 2, Maitland, FL 32751
• 

  

  /20

  Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft

  1140 S Orlando Ave Unit D11, Maitland, FL 32751

  1140 S Orlando Ave Unit D11, Maitland, FL 32751
• 

  

  /20

  $779,500 Pending

  • 3 Beds
  • 2 Baths
  • 1,813 Sq Ft

  421 Arapaho Trail, Maitland, FL 32751

  Welcome to this charming, move-in ready home nestled in the desirable, family-friendly Dommerich neighborhood. Featuring 3 bedrooms, 2 full bathrooms, and an open-concept living area filled with natural light, this home has the perfect blend of comfort and style. Featuring 2 additional dedicated office rooms, ideal for remote work or creative space, this home is ideal for modern living. The

  Steven Koleno BEYCOME OF FLORIDA LLC

  421 Arapaho Trail, Maitland, FL 32751
• 

  /2

  $315,000 Sold Apr 30, 2025

  1000 S Orlando Ave Unit 5, Maitland, FL 32751

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

  Last Sold Summary

  • 6% Below List Price
  • $331/SF
  • 41 Days On Market

  Current Estimated Value $327,677

  Last Listing Agent Laura Napoleon KELLER WILLIAMS WINTER PARK

  1000 S Orlando Ave Unit 5, Maitland, FL 32751
• 

  

  /28

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft

  1140 S Orlando Ave Unit C11, Maitland, FL 32751

  1140 S Orlando Ave Unit C11, Maitland, FL 32751
• 

  

  /18

  $525,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,753 Sq Ft

  1231 Glastonberry Rd, Maitland, FL 32751

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Don’t miss this beautifully updated 3-bedroom, 2-bathroom English Estates pool home with a versatile bonus room that can serve as a 4th bedroom, office, gym, or playroom—complete with its own private entrance. Priced below appraised value, this home is packed with thoughtful upgrades and modern conveniences.

  Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1231 Glastonberry Rd, Maitland, FL 32751
• 

  /2

  $417,500 Sold May 19, 2025

  2295 Park Maitland Ct, Maitland, FL 32751

  • 3 Beds
  • 2.5 Baths
  • 1,742 Sq Ft
  • Built 2002

  Last Sold Summary

  • 6% Below List Price
  • $240/SF
  • 174 Days On Market

  Current Estimated Value $422,020

  Last Listing Agent Christopher Soucy REALTY ONE GROUP MVP

  2295 Park Maitland Ct, Maitland, FL 32751
• 

  /2

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft

  1140 S Orlando Ave Unit D1, Maitland, FL 32751

  1140 S Orlando Ave Unit D1, Maitland, FL 32751
• 

  

  /33

  $309,000

  • 2 Beds
  • 2 Baths
  • 1,164 Sq Ft

  1000 Winderley Place Unit 222, Maitland, FL 32751

  Discover Sun Bay Club – Maitland’s Hidden Gem on Lake Destiny!Behind the signature blue gates lies this exclusive 68-residence community perfectly situated on the shimmering shores of Lake Destiny. Just minutes from Winter Park and downtown Orlando, this 2-bedroom, 2-bath second-floor condo offers a perfect blend of luxury and low-maintenance living.Completely remodeled in 2022, this home

  Jackie Swisher TRUST EQUITY GROUP LLC

  1000 Winderley Place Unit 222, Maitland, FL 32751
• 

  /2

  $396,000 Sold Jun 13, 2025

  1379 Benevolent St, Maitland, FL 32751

  • 3 Beds
  • 2.5 Baths
  • 1,789 Sq Ft
  • Built 2005

  Last Sold Summary

  • 1% Below List Price
  • $221/SF
  • 14 Days On Market

  Current Estimated Value $403,516

  Last Listing Agent John Stearns EXP REALTY LLC

  1379 Benevolent St, Maitland, FL 32751
• 

  

  /30

  Est $299,190 Not Listed For Sale

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

  210 Magnolia Rd Unit 210, Maitland, FL 32751

  210 Magnolia Rd Unit 210, Maitland, FL 32751
• 

  

  /43

  $625,000

  • 3 Beds
  • 2 Baths
  • 2,162 Sq Ft

  2167 Mohawk Trail, Maitland, FL 32751

  One or more photo(s) has been virtually staged. Celebrate the holidays in this charming 3 bedroom, 2 bath home nestled in one of Maitland’s most sought-after communities. As you step onto the inviting front porch and enter the foyer, you’re greeted by a sense of home, a perfect ambiance for festive celebrations and cherished family moments. This traditional residence features a spacious kitchen

  Lisa Gould KELLER WILLIAMS WINTER PARK

  2167 Mohawk Trail, Maitland, FL 32751
• 

  /2

  $855,000 Sold May 07, 2025

  1601 Lyndale Blvd, Maitland, FL 32751

  • 5 Beds
  • 2.5 Baths
  • 3,597 Sq Ft
  • Built 1967

  Last Sold Summary

  • 2% Below List Price
  • $238/SF
  • 45 Days On Market

  Current Estimated Value $1,097,093

  Last Listing Agent Carol van den Berg FLORIDA ONE REAL ESTATE LLC

  1601 Lyndale Blvd, Maitland, FL 32751
• 

  

  /33

  Est $417,959 Not Listed For Sale

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

  1100 S Orlando Ave Unit 508, Maitland, FL 32751

  1100 S Orlando Ave Unit 508, Maitland, FL 32751
• 

  

  /26

  $199,999

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

  500 Banyon Tree Cir Unit 104, Maitland, FL 32751

  One or more photo(s) has been virtually staged. Welcome to this beautifully renovated 3-bedroom, 2-bathroom first-floor condominium located in the established Carrington Park community. Offering 1,428 square feet of thoughtfully designed living space, this home combines modern upgrades with everyday functionality. Step inside to find a fresh, clean interior featuring tile and NEW beautiful luxury

  Amy Turner KELLER WILLIAMS WINTER PARK

  500 Banyon Tree Cir Unit 104, Maitland, FL 32751
• 

  /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 $522,595

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

  503 Lake Shore Dr, Maitland, FL 32751
• 

  

  /22

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft

  1140 S Orlando Ave Unit F12, Maitland, FL 32751

  1140 S Orlando Ave Unit F12, Maitland, FL 32751
• 

  

  /52

  $699,900

  • 6 Beds
  • 4 Baths
  • 2,484 Sq Ft

  933 and 935 Robinhood Ct, Maitland, FL 32751

  PRICE IMPROVEMENT! Whole Duplex. 6/4 (3 bed 2 bath in each unit). The Duplex is located in a cul-de-sac on a large lot that backs up to walking trail. Oakmont neighborhood has access directly to Sunrail Maitland Station. No HOA. Unit 933 has a fireplace for those cold Florida winters. The backyard is fully fenced and has an above-the-ground pool and a fully functionable bar with electric and

  Olaf Stenger CENTURY 21 INTEGRA

  933 and 935 Robinhood 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

  Last Listing Agent Allie George CORCORAN PREMIER REALTY

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

  /2

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 612 Sq Ft

  1140 S Orlando Ave Unit A3, Maitland, FL 32751

  1140 S Orlando Ave Unit A3, Maitland, FL 32751
• 

  

  /28

  $1,485,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,004 Sq Ft

  123 Hollie Ct, Maitland, FL 32751

  Under contract-accepting backup offers. Sophisticated and timeless, this stunning one-story home was completely reimagined in 2019 by multi-award-winning builder and design through Z-Properties. Taken down to the studs and rebuilt with the finest materials, this split-plan three-bedroom, three-bath residence blends modern design with an inviting, incredible design feel. Gorgeous high grade wood

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  123 Hollie Ct, Maitland, FL 32751
• 

  /2

  $515,000 Sold May 22, 2025

  1913 South Blvd, Maitland, FL 32751

  • 4 Beds
  • 3 Baths
  • 2,416 Sq Ft
  • Built 1969

  Last Sold Summary

  • 12% Below List Price
  • $213/SF
  • 243 Days On Market

  Current Estimated Value $520,345

  Last Listing Agent Juan Rijos LA ROSA REALTY ORLANDO LLC

  1913 South Blvd, Maitland, FL 32751
• 

  /2

  Est $388,314 Not Listed For Sale

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

  1100 S Orlando Ave Unit 308, Maitland, FL 32751

  1100 S Orlando Ave Unit 308, Maitland, FL 32751
• 

  

  /5

  $4,999,000 New Construction

  • 5 Beds
  • 8 Baths
  • 6,466 Sq Ft

  360 Lake Seminary Cir, Maitland, FL 32751

  Pre-Construction. To be built. An extraordinary opportunity to claim one of Lake Seminary’s desired shorelines awaits. Masterfully envisioned by Heathrow Custom Homes, this newly built lakefront estate introduces a fresh standard of modern luxury for Maitland and Winter Park. Poised on an expansive 0.69-acre parcel, the residence spans nearly 6,500 square feet of impeccably curated living space,

  Mel Bernstein PREMIER SOTHEBYS INT'L REALTY

  360 Lake Seminary Cir, Maitland, FL 32751

Showing Results 281 - 320, Page 8 of 18