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Winter Park and Maitland

Winter Park and Maitland are two neighboring historic towns, well-located just to the north of Downtown Orlando. Winter Park is the most famous area in Central Florida for locals for having its well-known “Park Avenue” downtown district with high-end shopping, award-winning dining, and art galleries. Winter Park has its own chain of lakes with the historic Rollins College and multimillion-dollar homes located along with them, where you can even take a boat tour. The city is diverse in that it has modest, older homes next door to larger, ultra-luxury homes built more recently, which has risen the value of all properties in the area substantially, making it a very hot real estate market. Many buyers opt to renovate these older homes or completely tear them down to build the larger, more luxurious ones due to
the inherent land value.

Maitland is located just north of Winter Park and it too has lakes connected to the famous chain of lakes, with a mix of modest homes and luxury homes. Maitland is famous for its art & history museums, and sports & recreation complexes, such as the RDV Sportsplex. There are several office buildings here too, with many national corporate headquarters located here.

$799,900 Active

5274 Baskin Street Orlando, Florida

3 Beds 3 Baths 1,757 SqFt 0.080 Acres

$797,300 Active

251 W Horatio Avenue Maitland, Florida

4 Beds 2 Baths 1,648 SqFt 0.470 Acres

$789,900 Active

400 W Trotters Drive Maitland, Florida

4 Beds 4 Baths 3,189 SqFt 0.290 Acres

$780,000 Active

4510 Lower Park Road Orlando, Florida

3 Beds 4 Baths 2,179 SqFt 0.050 Acres

$695,000 Active

706 Ponca Trail Maitland, Florida

3 Beds 2 Baths 1,798 SqFt 0.220 Acres

$692,000 Active

1862 Sipes Alley Orlando, Florida

3 Beds 4 Baths 2,038 SqFt 0.030 Acres

$689,000 Active

750 N Thistle Lane Maitland, Florida

4 Beds 2 Baths 2,310 SqFt 0.230 Acres

$445,900 Active

1806 Linden Road Winter Park, Florida

3 Beds 2 Baths 1,748 SqFt 0.270 Acres

$445,000 Pending

6324 Boyer Street Orlando, Florida

4 Beds 3 Baths 2,156 SqFt 0.160 Acres

$445,000 Active

6718 Pomeroy Circle Orlando, Florida

4 Beds 3 Baths 2,149 SqFt 0.150 Acres

$437,500 Active

1840 Maywood Road Winter Park, Florida

4 Beds 2 Baths 1,570 SqFt 0.210 Acres

$435,000 Pending

7303 Anstead Circle Orlando, Florida

3 Beds 2 Baths 1,353 SqFt 0.390 Acres

$435,000 Active

6456 Pomeroy Circle Orlando, Florida

4 Beds 3 Baths 2,001 SqFt 0.150 Acres

$429,000 Active

5524 Shasta Orlando, Florida

3 Beds 2 Baths 1,551 SqFt 0.220 Acres

$425,000 Pending

1988 Kenaston Road Maitland, Florida

3 Beds 4 Baths 2,103 SqFt 0.030 Acres

$375,000 Active

7915 Bates Road Winter Park, Florida

4 Beds 2 Baths 1,800 SqFt 0.580 Acres

$368,500 Active

Winter Park, Florida

3 Beds 2 Baths 1,524 SqFt 0.200 Acres

$360,000 Active

5315 Ashmeade Road Orlando, Florida

3 Beds 2 Baths 1,438 SqFt 0.220 Acres

$360,000 Active

8011 Lake Eve Drive Orlando, Florida

3 Beds 2 Baths 1,770 SqFt 0.560 Acres

$359,900 Active

5616 Shasta Drive Orlando, Florida

3 Beds 2 Baths 1,518 SqFt 0.220 Acres

$345,000 Active

3814 Groome Drive Orlando, Florida

3 Beds 2 Baths 1,040 SqFt 0.200 Acres

$345,000 Active

2704 Falkner Road Orlando, Florida

3 Beds 2 Baths 1,280 SqFt 0.360 Acres

$342,000 Active

8402 Tamarino Way Orlando, Florida

3 Beds 2 Baths 1,421 SqFt 0.220 Acres

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