Westchester Condos in Naples Florida

Westchester Condos is an intimate coach-home condominium community in Naples, Florida, centered along Westchester Court. With only 36 residences, Westchester offers a distinctly low-density atmosphere, spacious floor plans, attached garages and its own neighborhood pool, spa and community gathering area.

Westchester is especially appealing to buyers who want substantially more living space than a conventional condominium while retaining the convenience of condominium ownership. Residences provide approximately 2,160 to 2,686 square feet of air-conditioned living area, screened lanais and two-car garages, with views that may include golf, lake, preserve or mature landscaping.

Westchester Condos at a Glance

A Low-Density 36-Residence Community

Westchester's small size is one of its strongest distinguishing characteristics. With only 36 residences, the neighborhood feels considerably more private than a large condominium development containing hundreds of units.

The limited number of homes also means Westchester inventory can be scarce. There may be periods when only one or two residences are available, making floor level, view and condition particularly important when a property reaches the market.

Four Residences Per Building

Westchester buildings contain four coach-home residences rather than long corridors of condominium units. This configuration provides a more residential feeling with fewer immediate neighbors and private garage access.

End-unit positioning can provide additional windows and natural light, while upper-floor residences may benefit from elevated views and volume ceilings.

Westchester Court

Westchester Court forms the neighborhood's quiet internal street. The coach-home buildings are arranged around the cul-de-sac-style setting with mature landscaping and convenient access to the community recreation area.

The location of an individual building along Westchester Court can influence view, privacy and proximity to the neighborhood pool.

Two Principal Westchester Floor-Plan Sizes

Property and MLS records show two primary interior sizes throughout Westchester. The smaller residences provide approximately 2,160 square feet of air-conditioned living area, while the larger homes provide approximately 2,643 to 2,686 square feet.

That distinction is important when comparing Westchester sales because the larger coach homes provide more than 500 additional square feet of interior living space.

Buyers should compare like-sized residences whenever possible rather than relying on a neighborhood-wide price-per-square-foot average.

Approximately 2,160-Square-Foot Residences

The approximately 2,160-square-foot Westchester floor plan provides generous condominium living with two bedrooms plus flexible den or guest space represented in MLS records.

These homes can appeal to buyers who want an open main living area, private garage and large lanai without maintaining nearly 2,700 square feet.

Recent first-floor listings demonstrate how well this size can work for seasonal or full-time Naples living.

Approximately 2,643 to 2,686-Square-Foot Residences

The larger Westchester coach homes provide approximately 2,643 to 2,686 square feet of living area and can feel more like single-family homes than conventional condominiums.

Three- and four-bedroom configurations are represented, along with flexible dens, offices and guest suites.

The additional interior area can be particularly useful for buyers who regularly host family or plan to use Westchester as a full-time residence.

First-Floor Westchester Condos

First-floor Westchester residences provide direct living without interior stairs. Buyers can move easily between the garage, kitchen, bedrooms and lanai on one level.

This configuration can be especially attractive for buyers planning long-term ownership or those who prefer simplified accessibility.

First-floor homes may also provide a closer visual connection between the lanai and surrounding landscaping.

Second-Floor Westchester Coach Homes

Second-floor residences can provide elevated golf, lake, preserve or landscaped views along with greater separation from ground-level activity.

Larger upper-floor homes may include volume ceilings and additional architectural interest.

Some documented second-floor Westchester residences also include private elevators, an especially valuable feature for buyers who want an upper-level view without relying entirely on stairs.

Two-Car Attached Garages

Attached two-car garages are one of Westchester's strongest practical advantages. Unlike many Naples condominiums with detached single garages or open parking, Westchester homes provide substantial enclosed parking directly associated with the residence.

The garage can provide room for vehicles, bicycles, beach equipment, golf equipment and household storage.

Individual garages may also include workbenches, cabinets or additional owner-installed storage systems.

Large Screened Lanais

Screened lanais extend Westchester living into the outdoors and are oriented toward golf, water, preserve or landscaped surroundings depending on building location.

These covered outdoor spaces can accommodate dining tables, lounge seating and additional entertaining areas without requiring the owner to maintain a private swimming pool.

Lanai exposure and view should be compared carefully because they can create substantial differences between otherwise similar floor plans.

Golf Course Views

Some Westchester residences enjoy direct or partial golf-course views. Historical property records identify homes with golf-course exposure, and select properties combine golf views with lake or landscaped scenery.

An open fairway view can add significant visual depth to the lanai and main living areas.

Buyers should evaluate vegetation, building position and the precise angle of the view instead of relying only on an MLS view category.

Lake and Golf Views

Select Westchester homes combine lake and golf scenery, creating a layered view with water in the foreground and fairway landscaping beyond.

These homesites can provide some of the most open views available within the neighborhood.

Preserve Views

Preserve-oriented residences provide a different experience. Rather than overlooking active golf play, these homes can face mature vegetation, trees and natural scenery.

A 2026 Westchester sale specifically highlighted preserve views from a large upper-floor coach home.

Preserve settings can appeal to buyers prioritizing privacy and wildlife over fairway activity.

Landscaped Views

Other Westchester residences overlook mature community landscaping. Because the neighborhood is established, trees and tropical plantings have had decades to mature.

A landscaped view can provide privacy and a quiet residential atmosphere while keeping the property within easy walking distance of the neighborhood pool.

Westchester Community Pool

Westchester has its own private neighborhood swimming pool for residents. This allows owners to enjoy pool access without personally maintaining a private pool behind the residence.

The pool can be particularly attractive to seasonal owners who want convenient recreation while keeping individual maintenance responsibilities lower.

Community Spa

A community spa complements the neighborhood pool and provides another relaxing recreation option close to home.

Because these amenities are maintained collectively through the condominium association, buyers should review the association budget and reserve funding related to future pool and spa improvements.

Westchester Community Room

The neighborhood also includes a community gathering space that provides residents with an area for informal activities and social interaction.

Recent listings describe the Westchester recreation area as an easy walk from many residences, reinforcing the neighborhood's compact scale.

No Private Pool Maintenance

Westchester can appeal to buyers who enjoy swimming but do not want responsibility for an individual pool, heater, pumps, screen enclosure and weekly maintenance.

The shared pool arrangement reduces one major component of single-family home maintenance while still providing convenient water recreation.

Built Primarily in 2000 and 2001

Westchester's residences were constructed primarily around 2000 and 2001. The relatively concentrated construction period gives the neighborhood consistency in building style and original systems.

At the same time, more than two decades of ownership means individual units now differ significantly in renovation level.

Renovated Westchester Condos

Updated residences may include redesigned kitchens, modern cabinetry, stone countertops, newer appliances, wood or luxury flooring, renovated bathrooms and upgraded lighting.

Some Westchester homes have received extensive cosmetic improvements while others remain closer to their original design.

This creates opportunities for buyers seeking move-in-ready residences as well as those wanting to complete their own renovation.

Kitchen Improvements

Kitchen updates can have a significant effect on Westchester resale value. Recent properties include contemporary cabinetry, stone counters, stainless-steel appliances and more open relationships between the kitchen and living areas.

Because these are large coach homes, an improved kitchen can make the entire residence feel more current without requiring structural expansion.

Updated Bathrooms

Primary and guest bathrooms may also have been substantially remodeled over time. Updated showers, vanities, fixtures, cabinetry and flooring can differentiate a renovated Westchester home from one retaining original finishes.

Buyers should evaluate workmanship and permit requirements when major plumbing or structural changes have been made.

HVAC and Major Systems

Mechanical-system age should be reviewed carefully in Westchester. Current 2026 MLS activity includes homes with recently replaced HVAC equipment, while other residences may have older systems.

Water heaters, appliances, electrical components and garage-door equipment should also be included in the property inspection.

Roof and Building Exterior

Because Westchester is a condominium community, the association is responsible for significant common building components according to the governing documents.

Historical listings indicate roof and exterior projects have been completed within the community, but buyers should rely on current association records to understand future maintenance schedules and financial responsibility.

Westchester Condominium Association

Westchester at Kensington Condominium Association, Inc. is the legal condominium association governing the neighborhood. The association was established in 2000 and remains an active Florida not-for-profit corporation.

The association structure is important because Westchester owners share responsibility for common building and neighborhood expenses that differ from those of detached single-family homes.

What Westchester Condo Fees May Cover

Recent MLS records identify association services that may include items such as building insurance, cable or internet services, irrigation water, landscaping, professional management, exterior pest control, reserves, security, street-related expenses and recreation facilities.

The exact allocation can change over time and should be confirmed using the current condominium budget and estoppel.

Condo Insurance Responsibilities

Westchester buyers should understand the difference between the association's master insurance policy and the coverage an individual owner must carry for the interior residence and personal property.

Insurance deductibles, exclusions and owner responsibilities should be reviewed before closing.

Reserve Funding

Reserve funding is especially important in an established condominium community. Buyers should review current reserve schedules and planned capital projects for roofs, exterior painting, paving, recreation facilities and other common components.

A well-maintained interior does not eliminate the need to evaluate the financial condition of the condominium association.

Westchester Condo Documents

Important documents to review include:

Pet Rules

Recent Westchester listings describe the community as pet friendly subject to association limits. Buyers with pets should verify current number, size and breed restrictions directly through the condominium documents.

Rules can change and should not be assumed from an older MLS listing.

Rental Restrictions

Buyers considering seasonal or annual rental use should review Westchester's current leasing restrictions before purchasing.

Minimum lease terms, number of permitted leases, tenant approval requirements and waiting periods can materially affect investment flexibility.

Westchester Versus a Traditional Condo

Westchester differs from many conventional Naples condominiums because the residences provide single-family-style interior space, attached two-car garages and only four homes per building.

With approximately 2,160 to 2,686 square feet, many residences are larger than typical low-rise condominiums and can comfortably accommodate full-time living.

Westchester for Seasonal Owners

Seasonal buyers may appreciate Westchester's combination of substantial interior space and lower-maintenance condominium ownership. Owners can enjoy a large lanai, attached garage and neighborhood pool without maintaining a private yard or individual swimming pool.

This can make leaving the property for extended periods easier than managing a detached single-family home.

Westchester for Full-Time Residents

The larger floor plans also work well for full-time Naples residents. Multiple bedrooms, dens, large kitchens, storage and two-car garages provide the space needed for everyday living rather than only short seasonal stays.

Upper-floor residences approaching 2,700 square feet can provide a particularly strong alternative for buyers moving from a detached home.

Recent Westchester Sales

Westchester continues to generate meaningful resale activity. A large approximately 2,686-square-foot residence sold in May 2026, while additional 2026 inventory includes the approximately 2,160-square-foot floor plan.

This allows buyers and sellers to compare recent Westchester-specific activity rather than relying entirely on sales from other condominium neighborhoods.

Comparing Westchester Condos

When evaluating Westchester condos for sale in Naples, buyers should compare:

Westchester's Primary Value Drivers

The strongest Westchester value factors generally include floor-plan size, floor level, end-unit position, view, renovation quality and major-system condition.

A renovated approximately 2,686-square-foot upper-floor end unit with a private elevator may command a different level of buyer interest than an original-condition first-floor residence, even when both are located in the same small community.

Price Per Square Foot

Price per square foot can be useful when comparing similar Westchester residences but should not be used alone.

The difference between first- and second-floor homes, view quality, renovation level and private-elevator access can significantly affect market value.

The best comparable sales should closely match the subject residence in floor plan and property characteristics.

Optional Country Club Membership

Westchester ownership does not automatically require the purchase of a Kensington Golf & Country Club membership. Current MLS listings describe club membership as optional, allowing buyers to evaluate available membership categories separately from the condominium purchase.

Westchester's Naples Location

Westchester is located in the central Naples Pine Ridge Road area, placing residents close to shopping, restaurants, medical services, cultural destinations and Gulf beaches.

The combination of a quiet Westchester Court setting and convenient central location can be particularly appealing to seasonal owners who want easy access to everyday Naples destinations.

Why Buyers Choose Westchester

Westchester combines several characteristics that are difficult to find together: only 36 residences, large coach-home floor plans, attached two-car garages, private neighborhood recreation and a central Naples location.

Its approximately 2,160- to 2,686-square-foot residences provide substantially more room than many low-rise condominiums while preserving the lower-maintenance advantages of condo ownership.

Westchester as an MLS Community

Westchester is tracked separately because WESTCHESTER appears as its own condominium and subdivision designation in Southwest Florida MLS records.

Community-specific analysis is particularly useful here because Westchester's 36 coach homes differ considerably from the detached homes, villas and other condominium neighborhoods surrounding it.

Westchester Within Kensington

Westchester is located within gated Kensington Golf & Country Club, but the real estate focus of this page is the Westchester condominium neighborhood itself: its 36 residences, two principal floor-plan sizes, Westchester Court location, community pool, attached garages and condominium association.

The broader development provides location and optional club context, while Westchester's housing characteristics should drive the real estate comparison.

Explore Westchester Condos With Schulz Realty

Schulz Realty helps buyers and sellers evaluate Westchester Condos in Naples, Florida. Comparing Westchester Court residences by floor plan, floor level, view, private elevator, renovation quality, garage storage, association finances and recent Westchester sales can provide a clearer picture of each property's individual value.