Winter Park Homes with Maintenance Free Community Extras

Welcome to Winter Park, a charming city located in the sunny state of Florida. Known for its tree-lined streets, beautiful parks, and vibrant community, Winter Park is a highly sought-after destination for those looking to enjoy a high quality of life in a picturesque setting.

If you're in the market for a home with maintenance-free community extras, Winter Park has a range of options to choose from. Imagine coming home to a beautifully landscaped neighborhood where all exterior maintenance is taken care of for you, allowing you to spend your time enjoying the many amenities that these communities have to offer. From swimming pools and fitness centers to walking trails and social activities, living in a maintenance-free community in Winter Park provides a lifestyle of ease and convenience.

Whether you're looking for a cozy condo or a spacious townhome, Winter Park's homes with maintenance-free community extras offer a variety of floor plans and styles to suit your needs. Say goodbye to the hassle of yard work and exterior upkeep, and say hello to a more relaxed way of living in this vibrant city.

Come and explore the homes with maintenance-free community extras in Winter Park – where convenience meets luxury, and where you can truly enjoy all that this wonderful city has to offer.

Newest Winter Park Homes with Maintenance Free Community Extras

7605 Aloma Pines Court Unit 7605, Winter Park image

7605 Aloma Pines Court Unit 7605, Winter Park — 7605 $359,000

Virtually Staged! Amazing Townhome! GATED Community of Aloma Trails Townhomes in a great Winter Park location, 3 bedroom, 2.5 bathroom with features of spacious living an...

3 Beds
4 Baths
Aloma Trails SubDv.
32792 Zip Code

311 E Morse Boulevard Unit 4-5, Winter Park image

311 E Morse Boulevard Unit 4-5, Winter Park — Building 4 $1,050,000

Experience effortless Winter Park living in Whispering Waters, a premier 55+ lakefront community beautifully situated along the shores of Lake Osceola & just a short stro...

2 Beds
2 Baths
Phillips Circle Rep SubDv.
32789 Zip Code

2017 Canny Cove, Winter Park — 37 $399,900

Welcome home to this beautifully maintained, nearly new Pulte Townhome in the heart of Winter Park! Built in 2023, in the gated community of Grayson Square, this stylish...

3 Beds
3 Baths
Grayson Square SubDv.
32792 Zip Code

7450 Wynnewood Square Unit 189, Winter Park image

7450 Wynnewood Square Unit 189, Winter Park — Na $185,000

This charming 2-bedroom, 2.5-bathroom townhome style condo offers the perfect blend of comfort and convenience. Enjoy the peace of mind that comes with a new AC (2025), a...

2 Beds
3 Baths
Hidden Oaks Condo Ph 10 SubDv.
32792 Zip Code

1500 Gay Road Unit 4D, Winter Park image

1500 Gay Road Unit 4D, Winter Park — 4 $169,900 ▼

PRICE ADJUSTMENT! Lakefront Community! Enjoy Glorious Sunsets, Cocktails on the Deck and the Peace of Water and the Amazing Joy of Nature! All this near the heart of Wint...

1 Beds
1 Baths
Chateaux Du Lac SubDv.
32789 Zip Code

101 S New York Avenue Unit 311, Winter Park image

101 S New York Avenue Unit 311, Winter Park — Douglas Grand $1,849,900

Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of W...

3 Beds
4 Baths
Winter Park Residential SubDv.
32789 Zip Code

2500 Lee Road Unit 104, Winter Park image

2500 Lee Road Unit 104, Winter Park $249,900 ▼

At under $250,000, this renovated 2-bedroom, 2-bath condominium is truly move-in ready. The heart of the home is the custom kitchen (2025), which features soft-close cabi...

2 Beds
2 Baths
Lakeside Manor Apts Condo SubDv.
32789 Zip Code

193 Lewfield Circle, Winter Park — N/A $248,900

Virtually Staged. Welcome to 193 Lewfield Cir, Winter Park, FL 32792, a spacious two-story end-unit townhome offering 2 bedrooms, 2.5 bathrooms, and 1,300 square feet of ...

2 Beds
3 Baths
Stratford A Winter Park Condo SubDv.
32792 Zip Code

300 Carolina Avenue Unit 402C, Winter Park image

300 Carolina Avenue Unit 402C, Winter Park — C $710,000 ▼

Virtually Staged. Welcome to Park West Condominiums — one of Winter Park’s most coveted and rarely available condominium communities, ideally located just one block from ...

3 Beds
2 Baths
Park West Condo SubDv.
32789 Zip Code

1500 Gay Road Unit 17D, Winter Park image

1500 Gay Road Unit 17D, Winter Park — 17 $234,900 ▼

PRICE REDUCED TOTAL OF $25,000! AMAZING VALUE!!! Fantastic Winter Park Location on Lake Killarney. This 2 Bedroom 2 Bath Upstairs Unit has Lake and Pool Views. Spacious ...

2 Beds
2 Baths
Chateaux Du Lac SubDv.
32789 Zip Code

910 Enclave Place, Winter Park $1,899,000

Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneat...

5 Beds
5 Baths
The Enclave Winter Park SubDv.
32792 Zip Code

1090 Wildmeadow Run, Winter Park $835,000 ▼

One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buy-down that red...

4 Beds
4 Baths
Meadows At Hawks Crest SubDv.
32792 Zip Code