Westchester Condos For Sale | Longboat Key, FL
Westchester Community Guide
Westchester brings 72 residences to Longboat Key, built 1970-1974 with a community pool.
Search 900+ Neighborhoods & Condos By Name
Westchester Condominiums in Longboat Key, FL.
Westchester condos for sale sit at 4825 Gulf of Mexico Drive, north Longboat Key. Three midrise buildings, 72 units, built 1970 on 7 acres of private beachfront. Most units run around 1,393 square feet, two bedrooms, two baths. Impact windows and sliders meet Miami-Dade code, which cuts your insurance costs.
Amenities: two heated pools, tennis and shuffleboard courts, a fitness center, clubhouse, tiki huts, BBQ area. No pets allowed. Rentals capped at two per year, one month minimum each. Quarterly fees run high, average HOA around $1,858 a month, covering cable, insurance, maintenance, pest control, water, and sewer. Confirm exact current fees with the association since they vary by unit.
Photos of Westchester
Westchester Condo Facts
| Price Range: | $425kโ$925k |
| Year Built: | 1970 – 1974 |
| Size (Sq. Ft.): | 1,393 |
| Min. Lease: | 1 Month |
| Leases/ Year: | 2 |
| Gated: | ✖ No |
| Pool: | ✔ Yes |
| Pets Allowed: | ✖ No |
| Golf Course: | ✖ No |
| CDD Fee: | ✖ No |
*Accuracy of info provided is not guaranteed. All info must be verified before making a purchase decision.
Amenities:
Car Ports, Clubhouse, Tennis Court, Two Heated Pools, Outdoor Storage Locker, 3 Tiki Hut Areas, Pickle Ball, Shuffleboard, Basketball.
Fees Include:
Building Exterior, Cable, Community Pool, Ground Maintenance, Insurance Building, Manager, Pest Control, Roof, Tennis Courts, Trash Removal, Water/Sewer.
Condos For Sale in Westchester | Longboat Key, FL.
Honesty ยท Reputation ยท Experience ยท Top 2% Realtors in Sarasota

Map of Westchester
Additional Westchester Condo Information
Westchester condos feature 2-bedrooms, 2-baths consisting of about 1400 square feet. It is perfect retreat for taking in the morning sun, having your favorite beverage, making plans for the day and enjoying splendid evening sunsets. Bedrooms are split and located on either side of the living space providing privacy for owners and guests. Each bedroom has an ensuite and large walk-in-closets.
The beautiful white sands of the beach, the salt air, dolphins swimming by, families building sandcastles and wading in the warm water of the Gulf is perfection. There is a clubhouse, library, grilling section with picnic tables, tennis courts, shuffleboard, bike and kayak storage, beach cabanas, elevators and assigned covered parking. The two heated resort pools have Gulf views. There is a beautiful paver walkway adjacent to a garden setting with well-manicured lawns and mature trees throughout the complex.
It is a short drive to the grocery store, a variety of shops, dining, golfing and marinas. Explore the Cultural Coast for special events, attractions, live performances, theaters, galleries, museums and unique venues.
Westchester condominiums are situated in a stunning community with a variety of amenities, lovely grounds, and private beach that comes together to create a tropical lifestyle.
Westchester Condominiums
Westchester has about 72 condos, built between 1996-1997.
Yes, Westchester has a 2 heated pools.
No, Westchester is not a gated community.
Yes, Westchester is located in a golf course community.
No, Westchester is not located in a golf course community, but you may join the Longboat Key Club which offers the Islandside 18 Hole Golf Course and Harbourside 27 Hole Golf Course. Additionally, there are two clubhouses, 6 restaurants, an award winning tennis center with 22 Har-Tru courts, fitness center, full-service spa, and a 29 slip marina within Longboat Key Club.
Westchester is located about 10.3 miles from downtown Sarasota.
Westchester is located directly on the Beach of Longboat Key
Westchester is located about 13.6 miles from the Sarasota International Airport.
No, pets are not allowed in Westchester.
*Accuracy of info provided is not guaranteed. All info must be verified before making a purchase decision.

Our Personal Westchester Insights
Explore Longboat Key FL. Condominiums
Compare Longboat Key condo communities by location, amenities, price, and lifestyle.

Broker Associate & Realtors
Buying or Selling in Westchester?
Your local Westchester real estate experts.
Bill & Cheryl McCue and the Sarasota Homes Group know Westchester inside and out. 23 years of experience helping buyers and sellers in this market.
- Local Westchester Realtor with deep market knowledge.
- Top 2% selling Realtors in Sarasota & Manatee County.
- 23 years full-time experience.
- Current listings, sold data, and market trends for this area.
- Specializing in buying, listing, and selling homes in this market.
- Free market valuation for owners in this area.
- 100โs of 5-star reviews on Google, Realtor.com, Zillow, Homes.com and more.
- Sold over 500+ homes.
Bill & Cheryl McCue
Sarasota Homes Group



































