Maitland, FL Homes

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  /42

  $599,990 Open Sat 1PM - 4PM

  • 4 Beds
  • 2 Baths
  • 1,593 Sq Ft

  2654 Derbyshire Rd, Maitland, FL 32751

  Priced to sell! Nestled in the heart of Maitland, this 4 bedroom, 2 bath home is a sanctuary for those who demand the finest in life. Step into this stunning home, lovingly restored with attention to detail by the current owner, where modern comfort meets timeless charm. Inside discover meticulously updated spaces, where you will find a Zen-like screened porch and a serene back yard lushly

  

  Liz Morales

  FUSION FLORIDA REALTY LLC

  (321) 352-4550

  2654 Derbyshire Rd, Maitland, FL 32751
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  /72

  $1,455 - $2,327 per month

  Arbors at Maitland Summit

  1-3 Beds

  8636 Villa Point Dr, Orlando, FL 32810

  Arbors at Maitland Summit offers charming one-, two-, and three-bedroom apartment homes for rent just north of Orlando in Maitland, FL. Each pet-friendly apartment features a spacious layout, private patio or balcony, and upgraded finishes - including quartz countertops, stainless steel appliances, and wood plank flooring - in select homes. Take advantage of unique community amenities to

  8636 Villa Point Dr, Orlando, FL 32810
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  /2

  $299,999 Sold May 01, 2025

  • 1,860 Sq Ft
  • $161/SF
  • 26 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1974

  311 W Lake Faith Dr, Maitland, FL 32751

  One or more photo(s) has been virtually staged. Experience the best of Maitland living in this two-story condo nestled in the gated Lake Faith Villas community. Offering 1,860 square feet of comfortable living space, this home features an enormous open floor plan with updated vinyl flooring on the lower level. The living and dining areas flow seamlessly, opening to a private back patio with lush

  David Weiss COLDWELL BANKER REALTY

  311 W Lake Faith Dr, Maitland, FL 32751
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  /25

  Est $685,423 Not Listed For Sale

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

  2222 Chippewa Trail, Maitland, FL 32751

  2222 Chippewa Trail, Maitland, FL 32751
• 

  

  

  /30

  $479,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,231 Sq Ft

  651 Robinhood Dr, Maitland, FL 32751

  Under contract-accepting backup offers. Tucked away in one of Maitland's hidden gem neighborhoods, this charming home blends convenience and comfort effortlessly. Just a short stroll away, you'll find favorites like Publix, Kappy's Subs, and the Brightline station, while Luke’s Kitchen, Lake Lilly Farmer’s Market, and vibrant Winter Park are mere minutes from your doorstep. Easy access to I-4

  

  Heather Unger, PA

  ACME REAL ESTATE FLORIDA LLC

  (321) 850-3717

  651 Robinhood Dr, Maitland, FL 32751
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  /11

  $1,200 per month

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

  2525 Caper Ln Unit 205, Maitland, FL 32751

  Available now 1 bedroom 1 bath pool front condo for rent. Condo features plenty of natural light, full side kitchen, bathroom with bathtub shower combination and large walking closet. Community features 3 pools, fitness center and laundry facilities. One pool right in front of the unit. This is a beautiful second floor unit in CARRINGTON PARK which is a well established community within short

  David Lozano LOZMOR REALTY

  2525 Caper Ln Unit 205, Maitland, FL 32751
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  /2

  $235,000 Sold May 01, 2025

  • 1,565 Sq Ft
  • $150/SF
  • 220 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1979

  881 Town Cir Unit 129, Maitland, FL 32751

  Huge Price Improvement!!! Check out this meticulously maintained 3 bedroom 2.5 Bath Condo in the heart of Maitland. Updates include a New AC system, electrical panels, appliances, hot water heater, all new flooring upstairs, brand new exterior fenced in yard and fresh paint throughout. This two-story condo features a rear entry garage and an oversized fenced courtyard leading into the home. The

  Dean Erlandson LIVE FLORIDA NOW LLC

  881 Town Cir Unit 129, Maitland, FL 32751
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  /30

  Est $484,415 Not Listed For Sale

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

  2027 Michael Tiago Cir, Maitland, FL 32751

  2027 Michael Tiago Cir, Maitland, FL 32751
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  /46

  $669,500 Pending

  • 4 Beds
  • 2 Baths
  • 2,188 Sq Ft

  901 Ponca Trail, Maitland, FL 32751

  Under contract-accepting backup offers. Pride of home ownership shines through in this fabulous 4-bedroom 2 bath pool home. This Maitland home is in Orange County, so you have the best Winter Park Schools. No Homeowners Association. Recent enhancements to this home are an updated kitchen, 2022 Trane HVAC, a 16x20 addition (Mancave), Windows replaced in 2017 and 2020, Appliances in 2017. (Washer

  

  Walter Borgen

  RE/MAX SIGNATURE

  (321) 360-5984

  901 Ponca Trail, Maitland, FL 32751
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  /20

  $1,716 - $3,403 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

  $709,000 Sold May 01, 2025

  • 1,894 Sq Ft
  • $374/SF
  • 184 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1965

  2260 Gillis Ct, Maitland, FL 32751

  Welcome to 2260 Gillis Court, a luxurious haven nestled in the heart of the sought-after Dommerich community in Maitland, FL. This exquisite 4-bedroom, 2-bathroom residence offers a modern and personable living experience, perfect for those who appreciate elegance and comfort.Step inside to discover an open concept layout that seamlessly blends style and functionality. The home boasts 1,894

  Ahmad Hassan COMPASS FLORIDA LLC

  2260 Gillis Ct, Maitland, FL 32751
• 

  

  /17

  Est $211,824 Not Listed For Sale

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

  500 Banyon Tree Cir Unit 104, Maitland, FL 32751

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

  

  /20

  $868,000

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

  245 W George Ave, Maitland, FL 32751

  LOCATION of this amazing property in Maitland. With New ROOF -AC UNIT - WATER HEATER - FLOORING , a modern kitchen, and updated bathrooms, this home combines contemporary upgrades with classic charm, making it truly move-in ready. It features a new fence BBQ space and Pool—perfect for outdoor entertaining. The property is just a short walk to the Sybelia Lake , allowing residents to enjoy nature

  Jose Leighton Reyes MIHOUSE REALTY LLC

  245 W George Ave, Maitland, FL 32751
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  /29

  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 1,538 Sq Ft
  • Condo for Rent

  1000 Winderley Place Unit 138, Maitland, FL 32751

  Tastefully FULLY FURNISHED, FIRST , 3 bedroom condo! Golden Teak LVP Flooring throughout unit. **UPDATED and UPGRADED everything down to the oil rubbed bronze door hinges!** The kitchen (with stainless steel appliances) opens up to a spacious living/dining room with a wood burning fireplace and decorative trim makes this condo perfect for entertaining. Unit has been updated with crown molding,

  Bill Miller RE/MAX CENTRAL REALTY

  1000 Winderley Place Unit 138, Maitland, FL 32751
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  /2

  $315,000 Sold Apr 30, 2025

  • 952 Sq Ft
  • $331/SF
  • 41 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1964

  1000 S Orlando Ave Unit 5, Maitland, FL 32751

  Welcome to Maitland Harbour, a hidden gem where timeless Mid-Century Modern design meets the serenity of lakefront living. Designed by renowned architect Manfred Lopatka, a protégé of Frank Lloyd Wright, this boutique condominium was built in 1964 and embodies the unique Central Florida Mid-Century Modern architectural style. Inspired by a cruise ship, its design features wraparound balconies,

  Laura Napoleon KELLER WILLIAMS WINTER PARK

  1000 S Orlando Ave Unit 5, Maitland, FL 32751
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  /46

  Est $456,854 Not Listed For Sale

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

  2030 Michael Tiago Cir, Maitland, FL 32751

  2030 Michael Tiago Cir, Maitland, FL 32751
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  /41

  $565,000 Open Sat 10AM - 1PM

  • 4 Beds
  • 3 Baths
  • 2,304 Sq Ft

  1758 Bobtail Dr, Maitland, FL 32751

  This 4-bedroom, 3-bathroom home is packed with smart updates and sits in a prime Maitland location, close to shopping, dining, and quick access to the interstate for an easy commute to Orlando and beyond.Inside, you'll love the vaulted ceilings, new luxury vinyl flooring, and a clean, modern aesthetic throughout. The home has been freshly painted and features all-new lighting and fixtures, a

  Kelly Althof CENTRAL FLORIDA REALTY EXPERTS

  1758 Bobtail Dr, Maitland, FL 32751
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  /29

  $1,638 - $2,758 per month

  Brickstone Maitland Summit Apartments

  1-2 Beds

  9000 Summit Centre Way, Orlando, FL 32810

  Brickstone Maitland Summit is the apartment you've been looking for in Orlando, FL. With comfortable and spacious one-, two-, and three-bedroom apartments complete with upgraded finishes, private patios, and available attached garages, you're guaranteed to find a place to live with a lifestyle to love. What's more, you'll love our quaint lakeside community with a sparkling pool, 24-hour fitness

  9000 Summit Centre Way, Orlando, FL 32810
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  /2

  $889,000 Sold Apr 30, 2025

  • 3,210 Sq Ft
  • $277/SF
  • 68 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1963

  2061 Geronimo Trail, Maitland, FL 32751

  This is the ideal property, offered at the absolute lowest price you'll find in this desirable neighborhood. Don't miss out – act now before another buyer snaps it up! * Step into your private sanctuary where modern luxury meets timeless elegance. This meticulously renovated 4-bedroom, 3-bath residence exudes sophistication, featuring an open-concept floor plan, a gourmet kitchen, and exquisite,

  Sonya Dietsch TOP SAVING REALTY

  2061 Geronimo Trail, Maitland, FL 32751
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  /44

  Est $459,272 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,259 Sq Ft

  2005 Michael Tiago Cir, Maitland, FL 32751

  2005 Michael Tiago Cir, Maitland, FL 32751
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  /50

  $935,000

  • 3 Beds
  • 2 Baths
  • 2,502 Sq Ft

  195 E Faith Terrace, Maitland, FL 32751

  Welcome home to this rare hidden gem on the shores of Lake Seminary in Maitland! Nestled at the end of a quiet dead-end street, this beautifully renovated and landscaped ranch-style home offers 3 bedrooms, 2 full baths, and a spacious 2-car garage.With its inviting curb appeal and lush landscaping, this home is truly special. Inside, the open kitchen is perfect for entertaining, featuring

  Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

  195 E Faith Terrace, Maitland, FL 32751
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  /11

  $1,795 per month

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Condo for Rent

  2640 Legacy Villas Dr Unit 2640, Maitland, FL 32751

  2/2, 2 Car Garage, Three Story Condominium, Living Room, Dining Room, Kitchen Appliances Included: Stove, Refrigerator, Disposal, Microwave and Dishwasher, Bonus Room, Inside Closet Utility Room with Washer and Dryer Hookups, Walk in Closets, Carpet and Tile Throughout Home, Gated Community with Community Pool, Clubhouse, Fitness Center, Playground, BBQ Grills, Pest Control Included by HOA, Pets

  Tina Lopez LEGENDS REALTY

  2640 Legacy Villas Dr Unit 2640, Maitland, FL 32751
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  /2

  $1,520,000 Sold Apr 30, 2025

  • 5,517 Sq Ft
  • $276/SF
  • 121 Days On Market

  • 6 Beds
  • 6 Baths
  • Built 1959

  400 S Lake Sybelia Dr, Maitland, FL 32751

  Tucked away on over half an acre, this beautifully maintained lakefront home on Lake Sybelia blends modern updates with timeless charm, making it an ideal retreat for those seeking space, comfort, and privacy. Available for the first time in over 45 years, the home has been thoughtfully renovated and expanded over time, resulting in a highly functional layout featuring 6 bedrooms + an office, an

  Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  400 S Lake Sybelia Dr, Maitland, FL 32751
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  /22

  Est $193,920 Not Listed For Sale

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

  2333 Coawood Ct Unit 103, Maitland, FL 32751

  2333 Coawood Ct Unit 103, Maitland, FL 32751
• 

  

  /39

  $829,000

  • 3 Beds
  • 2 Baths
  • 1,901 Sq Ft

  2004 Mohawk Trail, Maitland, FL 32751

  Fully renovated Dommerich home in Maitland on a wrapping corner lot has been completely redesigned with entertaining at the forefront. A spacious reshape of the kitchen and living spaces create a large gathering space for ease and function with windows out to backyard yard retreat. This custom kitchen features 42-inch white shaker cabinetry with quartzite counters, enjoy a generous center island

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  2004 Mohawk Trail, Maitland, FL 32751
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  /103

  $1,771 - $9,393 per month

  Trelago Apartments

  Studio-3 Beds

  601 Trelago Way, Maitland, FL 32751

  The best way to enjoy life in Maitland, is from a vibrant lakefront community that replicates the indulgent atmosphere of a five-star resort. Trelago Apartments offers that, and much more. From the ultra-spacious one, two- & three-bedroom floor plans to the exceptional amenities, every feature of our Maitland apartments is designed to take your comfort to the next level. Your unique experience

  601 Trelago Way, Maitland, FL 32751
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  /2

  $400,000 Sold Apr 30, 2025

  • Land
  • 0.23 Acre
  • $1,739,130 per Acre

  • 121 Days On Market

  294 Macarthur Place, Maitland, FL 32751

  This is a great opportunity to build your dream home or to purchase this lot in addition to the adjacent parcel for sale at 400 S. Lake Sybelia Drive, MLS #O6255437. Both properties can be purchased together for a combined dry land lot size of approximately 0.83 acres. The location is convenient, situated close to the Maitland Farmers Market, Maitland City Centre, Lake Lily, fine restaurants, and

  Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  294 Macarthur Place, Maitland, FL 32751
• 

  

  /11

  Est $430,619 Not Listed For Sale

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

  1100 S Orlando Ave Unit 704, Maitland, FL 32751

  1100 S Orlando Ave Unit 704, Maitland, FL 32751
• 

  

  /21

  $575,000 Open Sat 12PM - 4PM

  • 4 Beds
  • 2 Baths
  • 1,655 Sq Ft

  1529 Glastonberry Rd, Maitland, FL 32751

  Welcome to 1529 Glastonberry Rd., a beautiful 4 bedroom, 2 bath pool home in an established neighborhood in Maitland. The home is bright and airy with fantastic luxury vinyl flooring, new interior paint and modern lighting. The open concept is perfect for entertaining with a spacious kitchen, updated appliances and granite countertops. The views of the sparkling pool will encourage all to step

  Tamara Rorman RE/MAX TOWN CENTRE

  1529 Glastonberry Rd, Maitland, FL 32751
• 

  

  /21

  $3,995 per month

  • 4 Beds
  • 2 Baths
  • 1,961 Sq Ft
  • House for Rent

  2430 Deloraine Trail, Maitland, FL 32751

  Live in this beautiful 4/2 pool home in the Dommerich area! Pool and lawn care are included! Enjoy the formal living and dining room with all appliances and washer/dryer. This home has wood floors and tile throughout! Great Location next to top rated schools, Dommerich Elementary, Maitland Middle, and Winter Park High! Also close to Maitland Community Parks! *Bonus Amenity Included* -All RE/MAX

  Shawn Beard RE/MAX 200 REALTY

  2430 Deloraine Trail, Maitland, FL 32751
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  /2

  $505,000 Sold Apr 28, 2025

  • 1,898 Sq Ft
  • $266/SF
  • 21 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1973

  145 Roosevelt Place, Maitland, FL 32751

  BOAT OR RV PARKING NO HOA! Welcome to this exceptional 4-bedroom, 2-bathroom split plan POOL home in the heart of Maitland! Nestled on a quiet cul-de-sac with an expansive lot, this move-in-ready home boasts an open floor plan flooded with natural light. The layout features a formal living and dining room with hardwood floors, crown moldings, spacious kitchen w/ new appliances that overlook the

  Todd Schroth EXP REALTY LLC

  145 Roosevelt Place, Maitland, FL 32751
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  /16

  Est $197,629 Not Listed For Sale

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

  2305 Haywood Ct Unit 101, Maitland, FL 32751

  2305 Haywood Ct Unit 101, Maitland, FL 32751
• 

  

  /43

  $400,000

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

  1379 Benevolent St, Maitland, FL 32751

  Welcome to Montacino—a peaceful, gated oasis where style meets convenience. This 3-bedroom, 2.5-bath townhome offers timeless character and solid craftsmanship, with no rear neighbors and tranquil rear exposure. Designed with enduring finishes, the home features granite countertops, stainless steel appliances, and classic crown molding throughout the main living areas.Enjoy a functional layout

  John Stearns EXP REALTY LLC

  1379 Benevolent St, Maitland, FL 32751
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  /127

  $1,670 - $3,105 per month

  Dwell Maitland

  1-2 Beds

  8700 Maitland Summit Blvd, Orlando, FL 32810

  Located just 10 minutes from downtown Orlando, Florida, Dwell Maitland Apartments by The Klein Company is a completely unique experience in 21st century luxury apartment living. Everywhere you want to be is within easy reach. Situated just 1 mile from I-4, Dwell Maitland offers an easy commute to major corporate centers, shopping and dining. Dwell is located directly adjacent to the RDV

  8700 Maitland Summit Blvd, Orlando, FL 32810
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  /2

  $930,000 Sold Apr 28, 2025

  • 3,189 Sq Ft
  • $292/SF
  • 122 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1960

  400 W Trotters Dr, Maitland, FL 32751

  One or more photo(s) has been virtually staged. This beautifully updated mid-century home is located in the desirable Delroy Park neighborhood of Maitland, offering the ideal setting for your dream family home. Positioned on a spacious corner lot, this residence blends classic elegance with modern comfort.As you enter, you're welcomed by the timeless beauty of hardwood floors throughout the main

  Sylvester Harding SIERRA REALTY GROUP LLC

  400 W Trotters Dr, Maitland, FL 32751
• 

  

  /21

  Est $329,913 Not Listed For Sale

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

  1000 Winderley Place Unit 126, Maitland, FL 32751

  1000 Winderley Place Unit 126, Maitland, FL 32751
• 

  

  /28

  $610,000

  • 4 Beds
  • 2.5 Baths
  • 2,621 Sq Ft

  702 Green Meadow Ave, Maitland, FL 32751

  This unique, custom-built concrete block home is nestled on a quiet cul-de-sac in the highly sought-after Forest Brook neighborhood. Lovingly maintained, this spacious residence features a grand foyer, formal living and dining rooms, and a bright, airy family room with a cozy fireplace. The open kitchen boasts a gas oven, abundant cabinetry, and a charming eat-in area with built-in desk and

  Cheryl Geluso RE/MAX ASSURED

  702 Green Meadow Ave, Maitland, FL 32751
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  /14

  $1,895 per month

  • 3 Beds
  • 2 Baths
  • 1,243 Sq Ft
  • Condo for Rent

  1460 Lake Shadow Cir Unit 7205, Maitland, FL 32751

  This beautiful three-bedroom, two bath 1,243 sqft condo is located on the second floor of the gated community of Visconti in Maitland. Located on the second floor, the condominium features volume ceilings in the living areas for an open and expansive feeling with the living room opening to a screened in patio through the oversized sliding glass doors. The kitchen overlooks the living and dining

  Justin Recca INNOVATIVE REALTY, LLC

  1460 Lake Shadow Cir Unit 7205, Maitland, FL 32751
• 

  /2

  $330,000 Sold Apr 25, 2025

  • 928 Sq Ft
  • $356/SF
  • 49 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1953

  206 Tangerine Place, Maitland, FL 32751

  Investor Special! Unique Charm in a Prime Maitland Location!Welcome to 206 Tangerine Pl, a 2-bedroom, 1-bathroom home bursting with unique charm and endless potential. Nestled on a quiet dead-end street, this property offers tons of privacy, making it a hidden gem in one of Maitland’s most desirable locations. This is a fantastic opportunity for investors or buyers looking to renovate and add

  Amanda Binns STRICKLAND REALTY GROUP INC

  206 Tangerine Place, Maitland, FL 32751
• 

  

  /15

  Est $113,741 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 550 Sq Ft

  551 Flemming Way Unit 101, Maitland, FL 32751

  551 Flemming Way Unit 101, Maitland, FL 32751

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