Costs of owning

What it really costs to own in Florida.

Grayson Square HOA fees

Winter Park, Seminole County · 32792

Homes in Grayson Square (Winter Park) pay a median $4,500 a year in HOA dues, about $375 a month, based on 5 listings. Half fall between $4,500 and $4,500. None of the listings we reviewed report a CDD.

HOA, median
$4,500/yr
About $375 a month
CDD, median
None reported
Property tax, median
$6,887/yr
Seller's bill; resets after a sale
Monthly, before mortgage
$949
HOA + tax at the medians

What the dues cover

  • Cable TV80% of listings
  • Pool80% of listings
  • Internet80% of listings
  • Maintenance Grounds80% of listings
  • Maintenance Structure40% of listings
  • Management20% of listings

Amenities listed: Cable TV, Pool, Maintenance, Gated, Park.

Live inventory

For sale in Grayson Square right now

4 active listings

2857 Clever Ln
ActivePrice reduced
Townhouse for sale
$399,995
$18k
3 bed3 bath1,782 sqft0.05 acre lot
2857 Clever Ln
Winter Park, FL, 32792
Brokered by MAINFRAME REAL ESTATE
2017 Canny CV
ActivePrice reduced
Townhouse for sale
$379,998
$20k
3 bed3 bath1,907 sqft0.04 acre lot
2017 Canny CV
Winter Park, FL, 32792
Brokered by KELLER WILLIAMS WINTER PARK
2033 Canny CV
ActivePrice reduced
Townhouse for sale
$389,000
$10k
3 bed3 bath1,907 sqft0.04 acre lot
2033 Canny CV
Winter Park, FL, 32792
Brokered by LPT REALTY, LLC
1995 Canny CV
ActivePrice reduced
Townhouse for sale
$399,000
$26k
3 bed3 bath1,907 sqft0.04 acre lot
1995 Canny CV
Winter Park, FL, 32792
Brokered by KELLER WILLIAMS ELITE PARTNERS III REALTY
See all 4 Grayson Square homes

Grayson Square cost questions

How much are HOA fees in Grayson Square?

Homes in Grayson Square (Winter Park) pay a median $4,500 a year in HOA dues, about $375 a month, based on 5 listings. Half fall between $4,500 and $4,500.

Does Grayson Square have a CDD?

None of the listings we reviewed report a CDD. Check the tax bill on any home you're serious about: a CDD shows up there as a separate assessment.

What does it cost each month to own in Grayson Square, before the mortgage?

HOA and property tax come to about $949 a month at the medians (property tax median $6,887 a year). Insurance and the mortgage come on top. Property tax resets after a sale under Florida's homestead rules, so a buyer's bill can be higher than the seller's.

Where do these numbers come from?

Stellar MLS via Repliers listings in Grayson Square from January 2026 to October 2026: homes for sale now plus closed sales in that period, one data point per address (rentals excluded). Fees are converted to annual figures. Individual homes vary by association and home type, so confirm the exact fee on any home before you make an offer.

Source: Stellar MLS via Repliers, January 2026 to October 2026. Medians from 5 addressesin subdivisions matching “GRAYSON SQUARE”, phases combined. Listing data is reported by listing agents and can be out of date. Updated 2026-10-11.

Compare nearby communities

Own in Grayson Square?

Get a real value review from our team.

We'll pull the recent sales in your community and tell you what your home would sell for today. No obligation.

Book a callCall now