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Welcome to this old unincorporated community in Florida. Maitland has grown tremendously and the local residents are the best people that you can have as neighbors. They are charming, warm and amicable. They are proactive in every activity so as to ensure that all of them participate in the communal activities. Maitland has some of the best historical residences, which can give you the comfort that you need together with a unique blend of tradition and class.

Community Summary

Homes for Sale

The price range for this neighborhood is from $0 to $3,450,000

134 Total Listings
$499,027 Average Price
2,163 Average Square Feet
174 Average Price / SqFt


All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
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700 Manor Rd, Maitland

Phenomenal apprx 3.5-4 acre Lake Maitland estate property with water on 3 sides... Private setting on this one of a kind Chain of Lakes lakefront property with majestic live oaks & cypress trees around perimeter... A picturesque park like setting on a peninsula with panoramic water views of Lake Maitland, Lake Nina and canal frontage. Existing dock and boat lift on property. Build a lifelong dream gated estate -or- possibly split into 2 or

150 Northwind Rd, Maitland

5 Beds, 7 Baths, 5,000 SqFt
Build the home of your dreams! The opportunity is yours on this vacant lot. A talented local team has delivered an example of a stunning home that could be built on this lot. The example is designed by John Drake with Green Apple architecture and built by e2 Homes. A modern single family home located in the desirable community of Lake Maitland Owl Preserve The home focuses on clean lines and top quality finishes. From the moment you walk into

250 Northwind Rd, Maitland

4 Beds, 6 Baths, 4,500 SqFt
**Under Construction** Designed by award-winning architect Michael Wenright and built by e2 Homes, this modern single-family home is located in the brand new Lake Maitland Owl Preserve community. From the moment you walk into the home you’ll notice clean lines and high-end finishes. Boating over 4,500 SF the openness of the floor plan creates the perfect environment for family gatherings and casual entertainment. Featuring 4 bedroom, 5.5

620 Bentley Ln, Maitland

5 Beds, 5 Baths, 5,521 SqFt
The Winter Park Chain Of Lakes Lifestyle – LIVE IT in this beautiful 2 story home with a south facing heated infiniti pool and spa with a spectacular view of Lake Minnehaha. Imagine . . . wakeboarding, jet skiing, sunset cruises, and going down to Park Avenue by boat to shop and dine – they are all a part of your lifestyle. And, imagine living in this very special home . . . custom wood cabinets throughout - the kitchen with its granite

271 Shell Pt E, Maitland

5 Beds, 4 Baths, 3,917 SqFt
Pristine Lake Maitland 5 bedroom 4 bath home. This stunning Winter Park Chain of Lakes home has 92 feet of spectacular lakefront providing unparalleled views of Lake Maitland. Downstairs private master retreat with tranquil views of pool and Lake Maitland has workout room and lavish bath with his and her sinks, beautiful granite counter tops, and separate tub and shower. Top quality finishes inside and outside including Pella doors and windows,

971 N Lake Sybelia Dr, Maitland

5 Beds, 6 Baths, 5,698 SqFt
Lakefront Estate Treasure! Gorgeous - Secluded over 1.6 acres of park-like land on private side of this pristine ski lake. Southern Traditional Home by Jones-Clayton Construction & designed by Dan Delong. Impressive gated entrance with circular driveway. Formal areas & very open floorplan Detailed woodwork & trim. Beautiful hardwood floors, 3 gas fireplaces, custom wood built-ins in study. Master bedroom plus guest bedroom with its

467 Lake Howell Rd, Maitland

5,984 SqFt

940 S Lake Sybelia Dr, Maitland

Buyers have been waiting a long time for this unique opportunity! 135 Feet of spectacular LAKEFRONT vacant land on Lake Sybelia, a FRESHWATER SKI LAKE, REFRESHED BY SPRINGWATER. Lake is PRIVATE as all of the shoreline properties extend into the lake & join other shoreline properties, with no public boat launching allowed. Ideal for someone looking to build their custom dream home. Lake Sybelia is a large 81 acre lake in the beautiful

129 Whitecaps Cir, Maitland

4 Beds, 3 Baths, 2,225 SqFt
REMODELED AND UPGRADES GALORE! This breathtaking 4 bedroom, 3 bathroom home is on just over a quarter acre on Lake Maitland! No expense spared.... Fabulous open floor plan giving amazing scenic views of the lake. Gourmet kitchen with granite counter tops, lovely back-splash, stainless steel appliances, built in oven, built in microwave, flat top cook range and breakfast bar. Great room features modern accents, fireplace and french doors

131 Stone Hill Dr, Maitland

5 Beds, 6 Baths, 5,012 SqFt
Beautiful, transitional, custom-built lakefront home located in Maitland on ski-able Lake Seminary. This 5 bedroom home has a downstairs master retreat, dedicated office, and exercise room. The Home boasts gorgeous views across Lake Seminary, the pool and patio areas. Interior features include beautiful high sheen porcelain tile floors, a high end recently renovated chef’s kitchen equipped with Viking appliances and open to the family room.

90 Minnehaha Cir, Maitland

5 Beds, 5 Baths, 5,044 SqFt
Fabulous one-story sprawling lakefront property on chain of 6-lakes with oversized panoramic apprx 200 ft of lake frontage on what feels like a peninsula lot when you are on property… enjoy magnificent sunrises and sunsets!! Premium lot and a true tropical paradise with sandy beaches, majestic palms, oaks & cypress trees… Remodeled modern wide open floor plan, perfect for entertaining with high vaulted ceilings and walls of glass taking full

421 W Trotters Dr, Maitland

5 Beds, 4 Baths, 3,549 SqFt
This beautiful 5 bedroom 3 bath 3549 sq ft home is situated on 150 ft of canal frontage giving you access to the sought after “Winter Park Chain of Lakes” Nestled in the quiet Delroy Park just minutes away from shopping, restaurants and all that Maitland has to offer. Call for your private showing today!

Welcome to this old unincorporated community in Florida. Maitland has grown tremendously and the local residents are the best people that you can have as neighbors. They are charming, warm and amicable. They are proactive in every activity so as to ensure that all of them participate in the communal activities. Maitland has some of the best historical residences, which can give you the comfort that you need together with a unique blend of tradition and class.

Education in Maitland

The residential areas are conveniently located near some posh and classy schools, where your kids can have access to quality education. The Rollins College is located roughly two miles from the area and other universities are accessed with ease from Maitland. The highly educated workforce is a source of pride for the residents and this aspect will attract you too. The high quality of education has made the residents to design the historical corridor that moves from the center of the town to the lake area.

Top 5 Reasons To Buy In Maitland

  1. Community: A community rich with culture and growth
  2. Diverse & Affordable Maitland real estate opportunities
  3. Recreation: Great resturants and recreational opportunities in Maitland
  4. Employment: Young, growing population creates prosperous work futures

Amenities near Maitland

This area has a unique juxtaposition of the charm of a small town and a cool edginess. The culture of the area is preserved by the family parks, where you can go to relax and have fun as you enjoy live music from some renowned bands. Maitland has some of the best artists and it is said that they drink the water of Florida and rise to fame. If you meve to this place, you could also drink the same water and rise on your way to fame!

You are in for fun and thrill here. You can engage in historical activities that are held every year at the Maitland Art Festival, which takes place at the Lake Lily Park. You could also play other games in this park such as canoeing, boat riding and skiing.

History of Maitland

Maitland, one of the oldest incorporated municipalities in Central Florida, is a city rich in history. The area was once called Fumecheliga (Musk Mellon Place) by the Seminole Indians before it was established as Fort Maitland in 1838 by the U.S. Army. The fort was named after captain William Seton Maitland, a hero of the Seminole Wars who, ironically, was never in this area, having died in a battle near Tampa. At that time, the only way of getting to Central Florida was by boat from Jacksonville down the St. Johns River to Fort Mellon (Sanford), then by horse or foot. Fort Maitland was a small fort built on the west shore of Lake Maitland as a rest stop between Fort Mellon and Fort Gatlin (Orlando).

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Listing data comes from My Florida Regional MLS.