Maitland, FL Homes

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  $315,900

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

  1000 Winderley Place Unit 239, Maitland, FL 32751

  Discover Sun Bay Club – Maitland’s Hidden Gem on Lake Destiny!Behind the iconic blue gates awaits Sun Bay Club, a private 68-residence community nestled along the sparkling shores of Lake Destiny. Perfectly located within Maitland Center North and just 6 miles from downtown Orlando, this neighborhood offers both convenience and serenity.This 2-bedroom, 2-bath second-floor condo blends

  Christopher Nutt GALLERY PROPERTIES INTERNATIONAL

  1000 Winderley Place Unit 239, Maitland, FL 32751
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  /65

  $1,520 - $4,290 per month

  Bell Trelago

  Studio - 3 Beds

  601 Trelago Way, Maitland, FL 32751

  Bell Trelago welcomes you to a refined lakeside retreat where luxury, comfort, and convenience shape every moment. You can enjoy a relaxed yet sophisticated lifestyle enhanced by thoughtful amenities, beautiful waterfront views, and effortless access to dining, retail, and entertainment. The community blends style and function with elegant finishes, spacious studio, one-, two-, and three-bedroom

  601 Trelago Way, Maitland, FL 32751
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  /2

  $240,000 Sold Apr 21, 2025

  1000 Winderley Place Unit 122, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,164 Sq Ft
  • Built 1982

  Last Sold Summary

  • 4% Below List Price
  • $206/SF
  • 24 Days On Market

  Last Listing Agent Jean Chalifour COLDWELL BANKER REALTY

  1000 Winderley Place Unit 122, Maitland, FL 32751
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  /2

  Est $1,718,228 Not Listed For Sale

  470 Manor Rd, Maitland, FL 32751

  • 4 Beds
  • 3 Baths
  • 4,025 Sq Ft
  • Built 1981

  470 Manor Rd, Maitland, FL 32751

  Last Sold Summary

  • $429/SF
  • 2 Days On Market

  Last Sold Price $1,725,000

  Last Listing Agent Brian Hyser THE AGENCY FL
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  /30

  $160,000

  • 1 Bed
  • 1 Bath
  • 672 Sq Ft

  1275 Lake Shadow Cir Unit 13206, Maitland, FL 32751

  One or more photo(s) has been virtually staged. Water views, brand-new mechanicals, and the best price in the building. This 1-bedroom, 1-bath condo at Visconti is offered at $9,000 less than the only comparable unit in the same building — and comes with a new Goodman 2-ton, 14.3 SEER HVAC system (2025), new water heater with expansion tank (2026), and a refreshed kitchen featuring new shaker

  Trevin Perez REDFIN CORPORATION

  1275 Lake Shadow Cir Unit 13206, Maitland, FL 32751
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  /10

  $1,200 per month

  • 1 Bed
  • 1 Bath
  • 540 Sq Ft
  • House for Rent

  301 Clark St, Maitland, FL 32751

  Cozy and private 1-bedroom, 1-bath rental located at Maitland. This comfortable unit features a small living area and a functional kitchen equipped with a stove and microwave, ideal for convenient everyday living.The rent includes water, electricity, and internet, offering a simple and hassle-free living experience. Conveniently located with quick access to nearby shopping, dining, and major

  Laury Cruz Penalo De Gomez MY REALTY GROUP, LLC.

  301 Clark St, Maitland, FL 32751
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  /2

  $475,000 Sold Dec 29, 2025

  1938 Michael Tiago Cir, Maitland, FL 32751

  • 4 Beds
  • 2.5 Baths
  • 2,708 Sq Ft
  • Built 2011

  Last Sold Summary

  • 4% Below List Price
  • $175/SF
  • 74 Days On Market

  Current Estimated Value $475,644

  Last Listing Agent Robin Mitchell ROBIN MITCHELL REALTY

  1938 Michael Tiago Cir, Maitland, FL 32751
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  /2

  Est $301,375 Not Listed For Sale

  555 Ruffel St, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,162 Sq Ft
  • Built 1970

  555 Ruffel St, Maitland, FL 32751

  Last Sold Summary

  • 3% Below List Price
  • $267/SF
  • 23 Days On Market

  Last Sold Price $310,000

  Last Listing Agent Nelson Folchini WRA BUSINESS & REAL ESTATE
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  /34

  $169,000

  • 1 Bed
  • 1 Bath
  • 707 Sq Ft

  1275 Lake Shadow Cir Unit 13102, Maitland, FL 32751

  Immediately available! This refreshed 1-bedroom, 1-bath ground-floor condominium with a deeded 1-car garage is the one you’ve been waiting for in the desirable gated community of Visconti West. Tucked away in the back of the community, this home offers a peaceful retreat with a private patio and tranquil surroundings. Step inside to a bright, airy interior featuring all-tile flooring and an open

  Juan Castro REDFIN CORPORATION

  1275 Lake Shadow Cir Unit 13102, Maitland, FL 32751
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  /89

  $1,495 - $2,945 per month

  The Tiffany at Maitland West

  1 - 3 Beds

  9301 Summit Centre Way, Orlando, FL 32810

  Submerge yourself into our culture. This resort-style, all-inclusive residential apartment community will take care of it all for you. 1-2 and 3-bedroom apartment homes feature beautiful, modern fixtures and appliances. Grey faux wood tile adorns the kitchen and living spaces. Cabinets that are a gorgeous, modern, two-toned zebra pattern with more storage space than you'd expect. Most units

  9301 Summit Centre Way, Orlando, FL 32810
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  /2

  $6,650,000 Sold Jun 27, 2025

  119 Whitecaps Cir, Maitland, FL 32751

  • 4 Beds
  • 5.5 Baths
  • 6,800 Sq Ft
  • Built 2004

  Last Sold Summary

  • $978/SF

  Current Estimated Value $6,631,006

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

  119 Whitecaps Cir, Maitland, FL 32751
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  /2

  Est $551,218 Not Listed For Sale

  1100 Charming St, Maitland, FL 32751

  • 4 Beds
  • 3 Baths
  • 2,355 Sq Ft
  • Built 2006

  1100 Charming St, Maitland, FL 32751

  Last Sold Summary

  • 2% Below List Price
  • $240/SF
  • 83 Days On Market

  Last Sold Price $565,000

  Last Listing Agent Amber Finch FINCH REAL ESTATE COMPANY
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  /32

  $419,900 Pending

  • 3 Beds
  • 2 Baths
  • 2,426 Sq Ft

  135 Roosevelt Place, Maitland, FL 32751

  This charming home boasts a wealth of valuable upgrades and improvements, making it an enticing opportunity for anyone seeking a move-in ready property The roof was replaced in 2006, ensuring long-lasting durability. A significant renovation in 2017 introduced modern conveniences, including all-new kitchen appliances and luxurious vinyl plank flooring, with extra flooring thoughtfully

  Julimar Barreiro Pastrana SERHANT

  135 Roosevelt Place, Maitland, FL 32751
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  /17

  $1,600 per month

  • 2 Beds
  • 1 Bath
  • 1,051 Sq Ft
  • Condo for Rent

  492 Banyon Tree Cir Unit 206, Maitland, FL 32751

  Available NOW! Enjoy comfortable, low-maintenance living in this well-located condo in Maitland. The layout is practical and easy to settle into, with a bright living area that opens to a private balcony—perfect for relaxing after a long day. The kitchen offers good cabinet space and flows naturally into the main living space, making everyday routines simple. The bedrooms are well sized with

  Valentina Naumenko MILA REALTY

  492 Banyon Tree Cir Unit 206, Maitland, FL 32751
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  /2

  $550,000 Sold May 02, 2025

  1870 Geronimo Trail, Maitland, FL 32751

  • Land
  • 0.27 Acre
  • $2,037,037 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 113 Days On Market

  Current Estimated Value $606,611

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

  1870 Geronimo Trail, Maitland, FL 32751
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  /20

  Est $297,407 Not Listed For Sale

  395 Sultana Ln, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1978

  395 Sultana Ln, Maitland, FL 32751

  Last Sold Summary

  • 10% Above List Price
  • $201/SF
  • 102 Days On Market

  Last Sold Price $270,000

  Last Listing Agent Tansey Soderstrom REAL ESTATE FIRM OF ORLANDO
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  /20

  $350,000

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

  1033 Hamlet Dr, Maitland, FL 32751

  This charming 3-bedroom, 2-bathroom single-family home with the best of Florida living. Located in the north of Orlando (Maitland - Winter Park area). 1.3 miles to the Center of Winter Park Shopping Plaza (Office Depot, UPS, Ross, Marshalls, Home Goods, Five Below, LA Fitness, Petco and Michaels, Whole Foods Markets, and Banking). Access to major highways, minutes to downtown, and Orlando's

  Bennie Olivo BOX REAL ESTATE LLC

  1033 Hamlet Dr, Maitland, FL 32751
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  /20

  $1,795 - $4,241 per month

  The Adeline

  1 - 3 Beds

  304 Lake Ave, Maitland, FL 32751

  Find the perfect balance of sophistication and relaxation at The Adeline in urban Maitland. Our community offers 1, 2, and 3 bedroom residences with modern features and luxurious amenities. Whether you live alone, are happy in love, or enjoy having roommates, feel at home in our elegant, French-inspired units. In the heart of the Greater Orlando area, The Adeline provides a warm, engaging

  304 Lake Ave, Maitland, FL 32751
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  /2

  $660,000 Sold May 27, 2025

  460 Forestwood Ln, Maitland, FL 32751

  • 4 Beds
  • 2 Baths
  • 2,049 Sq Ft
  • Built 1979

  Last Sold Summary

  • 12% Below List Price
  • $322/SF
  • 23 Days On Market

  Current Estimated Value $648,506

  Last Listing Agent Kevin Asenjo COLDWELL BANKER REALTY

  460 Forestwood Ln, Maitland, FL 32751
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  /2

  Est $308,485 Not Listed For Sale

  997 Hamlet Ct, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,146 Sq Ft
  • Built 1996

  997 Hamlet Ct, Maitland, FL 32751

  Last Sold Summary

  • $271/SF
  • 131 Days On Market

  Last Sold Price $310,000

  Last Listing Agent Dave Zembala ZEMBALA GROUP
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  /55

  $335,000

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft

  1000 S Orlando Ave Unit B25, Maitland, FL 32751

  Highly desirable Maitland Harbour, a boutique 38-residence lakefront condominium community nestled in the heart of Maitland. Ideally positioned on Lake Maitland—the largest lake on the Winter Park Chain of Lakes—this intimate and picturesque enclave offers access to the entire chain and a truly exceptional waterfront lifestyle. A hidden gem, Maitland Harbour blends timeless Mid-Century Modern

  Padgett McCormick KELLY PRICE & COMPANY LLC

  1000 S Orlando Ave Unit B25, Maitland, FL 32751
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  /34

  $1,785 per month

  • 1 Bed
  • 1 Bath
  • 612 Sq Ft
  • Condo for Rent

  1140 S Orlando Ave Unit E2, Maitland, FL 32751

  Live the lakefront lifestyle in this beautifully updated 1-bedroom condo located in the iconic mid-century modern community of Lake Maitland Terrace. Freshly painted and completely refreshed, this residence features brand-new appliances, a brand-new air conditioning system, and stunning new wood flooring throughout the main living areas. The bedroom offers sleek, modern concrete flooring—adding

  Beatrice Miranda METRO CITY REALTY

  1140 S Orlando Ave Unit E2, Maitland, FL 32751
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  /2

  $455,000 Sold Nov 10, 2025

  741 Robinhood Dr, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,239 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Above List Price
  • $367/SF
  • 18 Days On Market

  Current Estimated Value $441,512

  Last Listing Agent Dan Samatulski MAINFRAME REAL ESTATE

  741 Robinhood Dr, Maitland, FL 32751
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  /16

  Est $155,217 Not Listed For Sale

  1400 Lake Shadow Cir Unit 10304, Maitland, FL 32751

  • 1 Bed
  • 1 Bath
  • 672 Sq Ft
  • Built 2000

  1400 Lake Shadow Cir Unit 10304, Maitland, FL 32751

  Last Sold Summary

  • 3% Below List Price
  • $238/SF
  • 12 Days On Market

  Last Sold Price $160,000

  Last Listing Agent Isabel Sirizzotti SUNNY 365 REALTY GROUP
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  /28

  $739,990

  • 3 Beds
  • 2 Baths
  • 1,495 Sq Ft

  1741 Lyndale Blvd, Maitland, FL 32751

  Charming Newly Renovated Bungalow in Prime Maitland Location – Move-In Ready with Endless Potential!Discover this beautifully updated 3-bedroom, 2-bath bungalow at 1741 Lyndale Blvd, Maitland, FL 32751 – perfectly positioned on the edge of Winter Park for an unbeatable blend of tranquility and convenience. Freshly renovated and move-in ready, this home offers immediate comfort while sitting

  Matías Ugarte CHARLES RUTENBERG REALTY ORLANDO

  1741 Lyndale Blvd, Maitland, FL 32751
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  /47

  $1,610 - $2,464 per month

  400 North

  1 - 2 Beds

  400 N Orlando Ave, Maitland, FL 32751

  At 400 North, thoughtful home design meets effortless living in one of Maitland?s most connected neighborhoods. From the resort-style pool and fire pit lounge to the tranquil Zen courtyard, every outdoor space invites you to slow down and recharge. Inside, curated apartment features such as eat-in kitchen countertop seating and tiled baths meet spectacular lakeside views. With on-site retail and

  400 N Orlando Ave, Maitland, FL 32751
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  /2

  $550,000 Sold Jul 01, 2025

  2040 Mohawk Trail, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,754 Sq Ft
  • Built 1961

  Last Sold Summary

  • 6% Below List Price
  • $314/SF
  • 17 Days On Market

  Current Estimated Value $549,023

  Last Listing Agent Nicole Seybold FANNIE HILLMAN & ASSOCIATES

  2040 Mohawk Trail, Maitland, FL 32751
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  /25

  Est $666,169 Not Listed For Sale

  2222 Chippewa Trail, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft
  • Built 1961

  2222 Chippewa Trail, Maitland, FL 32751

  Last Sold Summary

  • 3% Below List Price
  • $352/SF
  • 33 Days On Market

  Last Sold Price $689,000

  Last Listing Agent Shirley Jones COLDWELL BANKER REALTY
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  /50

  $1,199,000

  • 5 Beds
  • 3.5 Baths
  • 4,144 Sq Ft

  791 Sequoia Trail, Maitland, FL 32751

  Discover a rare opportunity in Dommerich Woods, a distinguished and established Maitland neighborhood celebrated for its rich heritage. Situated on .33 acre of lushly landscaped grounds, this remarkable property welcomes with paver drive and enjoys a tranquil setting along apeaceful creek connecting Lake Minnehaha and Lake of the Woods - creating an atmosphere of natural elegance and

  David Van Wormer VANWORMER REALTY & DEVELOPMENT

  791 Sequoia Trail, Maitland, FL 32751
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  /23

  $1,995 per month

  • 3 Beds
  • 2.5 Baths
  • 1,204 Sq Ft
  • Townhouse for Rent

  210 N East St Unit B, Maitland, FL 32751

  FANTASTIC MAITLAND 3 BEDROOM 2 1/2 BATH TOWNHOUSE FOR RENT! This bright home with rear yard is located minutes from DT Maitland, Lake Lily, Eatonville, DT Orlando, DT Winter Park and all the shopping and conveniences of the 1792 retail/shopping corridor and Winter Park Village restaurants/theaters! Also minutes from Florida Hospital Health Village (Advent Health) and many local employers! You can

  Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

  210 N East St Unit B, Maitland, FL 32751
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  /2

  $3,950,000 Sold Jun 17, 2025

  33 Eastwind Ln, Maitland, FL 32751

  • 5 Beds
  • 4.5 Baths
  • 4,715 Sq Ft
  • Built 2024

  Last Sold Summary

  • $838/SF
  • 0 Days On Market

  Current Estimated Value $3,843,313

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

  33 Eastwind Ln, Maitland, FL 32751
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  /30

  Est $441,155 Not Listed For Sale

  2027 Michael Tiago Cir, Maitland, FL 32751

  • 3 Beds
  • 2.5 Baths
  • 2,193 Sq Ft
  • Built 2014

  2027 Michael Tiago Cir, Maitland, FL 32751

  Last Sold Summary

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

  Last Sold Price $460,000

  Last Listing Agent Doug Woehr COLDWELL BANKER REALTY
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  /27

  $499,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,224 Sq Ft

  1140 S Orlando Ave Unit C2, Maitland, FL 32751

  Under contract-accepting backup offers. Take advantage of a rare opportunity to own one of only five double units at Lake Maitland Terrace, perfectly situated on the Winter Park chain of lakes. This 1,224-square-foot ground-floor residence offers 2 bedrooms and 2 baths and has been fully reimagined and renovated with designer finishes, luxury appointments, and thoughtful accessibility features,

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  1140 S Orlando Ave Unit C2, Maitland, FL 32751
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  $1,999 - $3,789 per month

  Perla Gem Lake

  1 - 3 Beds

  100 Boucle Jeanne Cir, Maitland, FL 32751

  Drink in the waterfront views. Drop your kayak in for an evening cruise. Dip your toes in the saltwater pool. When you’re here, every day feels like a waterside retreat. Only it’s not a vacation, it’s your home. With nature-inspired interior design, multiple outdoor living spaces and direct lake access, Perla Gem Lake is luxury lakeside living.

  100 Boucle Jeanne Cir, Maitland, FL 32751
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  /2

  $515,000 Sold Sep 10, 2025

  204 Quayside Cir Unit 601, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,270 Sq Ft
  • Built 1984

  Last Sold Summary

  • 3% Below List Price
  • $406/SF
  • 45 Days On Market

  Current Estimated Value $485,919

  Last Listing Agent Travis Cepregi KELLER WILLIAMS WINTER PARK

  204 Quayside Cir Unit 601, Maitland, FL 32751
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  /46

  Est $440,350 Not Listed For Sale

  2030 Michael Tiago Cir, Maitland, FL 32751

  • 3 Beds
  • 2.5 Baths
  • 2,249 Sq Ft
  • Built 2014

  2030 Michael Tiago Cir, Maitland, FL 32751

  Last Sold Summary

  • 5% Below List Price
  • $205/SF
  • 4 Days On Market

  Last Sold Price $462,000

  Last Listing Agent Heather Ward WATSON REALTY CORP
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  /38

  $359,900

  • 2 Beds
  • 2 Baths
  • 1,403 Sq Ft

  353 W Lake Faith Dr Unit 116, Maitland, FL 32751

  Discover lakeside living at its finest in this beautifully updated 2nd-floor, private lakefront condo in the highly sought-after Lake Faith Villas in Maitland. Offering 1,400+ sq ft, this spacious 2 bed, 2 bath home features stylish parquet flooring throughout, a modernized kitchen and updated baths, newer appliances, HVAC, water heater, and updated electrical wiring for peace of mind. Enjoy

  Travis Cepregi KELLER WILLIAMS WINTER PARK

  353 W Lake Faith Dr Unit 116, Maitland, FL 32751
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  /15

  $3,200 per month

  • 4 Beds
  • 3.5 Baths
  • 2,474 Sq Ft
  • Townhouse for Rent

  1224 Trust Ln, Maitland, FL 32751

  Whether you're commuting to work, heading out for dining and entertainment, or just enjoying a quiet evening at home, this location makes daily life easier. Lakefront Luxurious Mediterranean TH in Sought after Gated resort style Community of Montacino. Enjoy Maintenance free living. Largest TH floor plan in montacino, only TH building with no townhouses behind and open parking. 2 MSTR Suites with

  Tina Prothero KELLER WILLIAMS WINTER PARK

  1224 Trust Ln, Maitland, FL 32751
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  /2

  $279,000 Sold Mar 06, 2026

  920 Park Lake Cir Unit 36, Maitland, FL 32751

  • 3 Beds
  • 2.5 Baths
  • 1,486 Sq Ft
  • Built 1972

  Last Sold Summary

  • 4% Above List Price
  • $188/SF
  • 72 Days On Market

  Current Estimated Value $263,751

  Last Listing Agent Melissa Johnson EXP REALTY LLC

  920 Park Lake Cir Unit 36, Maitland, FL 32751
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  /22

  Est $174,322 Not Listed For Sale

  2333 Coawood Ct Unit 103, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,206 Sq Ft
  • Built 1973

  2333 Coawood Ct Unit 103, Maitland, FL 32751

  Last Sold Summary

  • 8% Below List Price
  • $158/SF
  • 10 Days On Market

  Last Sold Price $190,000

  Last Listing Agent Lisa Sabo ALFANO PROPERTY MANAGEMENT

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