The Westchester

The Westchester is an oceanfront condominium building in Longboat Key, Florida, with a range of options priced between $675,000 and $890,000 depending on the floor location and the view of the Atlantic Ocean. There are currently a total of 7 condos for sale in The Westchester. The smallest Westchester condo presently available is a two bedroom two bathroom residence that is 1,604 square feet (1,393SF Under Air living space).

Property management fees in Sarasota County vary depending on the community and sometimes vary between units in the building. The current Condo fees for The Westchester are $5,575. This fee includes common area maintenance, grounds maintenance, building maintenance, maintaining the community roads, the community pool, and real estate taxes for common areas. Also included is property insurance, water, trash removal, sewer, pest control, Cable TV & internet, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular The Westchester condo.

Building amenities include a clubhouse, swimming pool, and laundry facilities. Sports facilities include tennis courts, pickleball courts, and shuffleboard. There is also private beach access.

There are two commercial airports that serve The Westchester - Sarasota Bradenton International (SRQ), which is six miles away, and Tampa International (TPA), which is 40 miles away.

The Westchester real estate activity on the Longboat Key MLS during the past year (as of May 2026) reflects two condos changing hands, with an average asking price of $710,000 and an average selling price of $672,500. This represents a healthy list-to-sell price ratio of 95% and $419 per square foot. During this period, The Westchester condos for sale have taken an average of 143 days to sell.

In addition, there are numerous other condo buildings in Longboat Key to choose from, many with direct ocean views, or you may browse all available Condos for sale in Longboat Key. Condos for sale in The Westchester are selling quickly. Set up a new listing alert, and we will notify you immediately when a new oceanfront condo in The Westchester hits the market. You can also always contact your ZFC Real Estate agent, who would happily assist you further with all your Florida real estate needs.

The Westchester Condos For Sale

Reduced

$890,000

$925,000

MLS#MFRA4674248

4825 Gulf Of Mexico Dr #202
Longboat Key, FL 34228

2

2

1,604 Sq Ft

Pool

Ocean Front

157 Days

Reduced

$849,900

$1,250,000

MLS#MFRA4642701

4835 Gulf Of Mexico Dr #302b
Longboat Key, FL 34228

2

2

1,604 Sq Ft

Pool

Water Front

1.55 Acres

433 Days

Reduced

$839,900

$899,000

MLS#MFRA4667044

4825 Gulf Of Mexico Dr #105
Longboat Key, FL 34228

2

2

1,604 Sq Ft

Water Front

221 Days

$825,000

MLS#MFRA4689724

4825 Gulf Of Mexico Dr #504
Longboat Key, FL 34228

2

2

1,393 Sq Ft

Pool

Ocean Front

1.09 Acres

9 Days

$749,900

MLS#MFRA4677656

4835 Gulf Of Mexico Dr #106
Longboat Key, FL 34228

2

2

1,604 Sq Ft

Pool

Ocean Front

1.55 Acres

93 Days

Under Contract

$699,000

$849,900

MLS#MFRA4677568

4805 Gulf Of Mexico Dr #103
Longboat Key, FL 34228

2

2

1,604 Sq Ft

Pool

Water Front

115 Days

Reduced

$675,000

$725,000

MLS#MFRA4684056

4835 Gulf Of Mexico Dr #105
Longboat Key, FL 34228

2

2

1,604 Sq Ft

Ocean Front

1.55 Acres

73 Days

7 Active Listings in The Westchester