About Berkshire Park Neighborhood
Berkshire Park sits in the southwest corner of Windermere's 34786 ZIP code, off Overstreet Road south of CR 535. The development was built out in phases between 2006 and 2014 by two production builders — Pulte Homes and Ashton Woods Homes — with traditional and neo-traditional architecture, brick or stucco fronts, two-car garages, and consistent setbacks across the streetscape.
Home sizes run from approximately 1,600 square feet on the smaller townhomes up to roughly 3,750 square feet on the largest single-family floor plans, with bedroom counts ranging from 3 to 6 and bathrooms from 2 to 4. Townhomes are clustered in the southern portion of the community furthest from the Overstreet entrances and closest to the CR 535 access point; single-family homes occupy the larger interior lots and pond-fronting parcels. Pricing typically falls in the mid-$300s through low-$700s depending on home type, size, and lot position.
The community is structured around a central amenity area with a swimming pool, cabana with restrooms, and a fenced playground. Several large stormwater ponds with fountains anchor the interior of the neighborhood, and walking paths trace the pond perimeters — a notable advantage for families looking for low-traffic places to bike, run, or push a stroller. A separately gated section, the Enclave at Berkshire Park, occupies the larger-lot portion of the community and shares amenities with the broader neighborhood. The result is a connected, family-oriented address with stronger amenities than most production-builder communities of its era.
📊 Quick Facts
🏠 Home Features
Most homes in Berkshire Park share a consistent set of mid-2000s through early-2010s production-builder features:
- Open-concept floor plans with combined kitchen, dining, and family rooms
- Granite or quartz kitchen counters (original or updated) with 42-inch upper cabinets
- Tile flooring in main living areas, carpet in bedrooms — many resales now feature wood-look LVP or engineered hardwood updates
- Two-car attached garages on single-family homes; one- to two-car garages on townhomes
- Master suites typically downstairs on single-story plans, upstairs on most two-story plans
- Covered lanais or screened porches; private pools on a subset of homes
- Pond views or preserve views on the most desirable lots
- Builder-grade impact-resistant or storm-rated windows on later phases (verify per home)
✨ What Makes Berkshire Park Distinct
- Full amenity package at a more accessible price point than most established Windermere addresses — pool, cabana, playground, and pond-front walking paths
- Mixed inventory of single-family homes and townhomes within the same HOA, allowing residents to right-size up or down without leaving the neighborhood
- Pond-front lots on a meaningful share of homes, with fountain water features and walking paths around the perimeters
- No CDD fee — a meaningful annual savings versus newer Horizon West master-planned communities
- Two access points (Overstreet Road on the east, CR 535 on the south for townhomes), useful for commuting in different directions
- The Enclave at Berkshire Park sub-community offers a separately gated entry on larger lots while still sharing the main amenity package
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Berkshire Park Location & Connections
Berkshire Park is located in the southwest corner of Windermere, accessed primarily off Overstreet Road south of Winter Garden Vineland Road (CR 535). The neighborhood sits between two established Windermere communities — Windermere Terrace to the north and Windermere Sound to the east — with wetland conservation areas bordering the south and west sides, providing a natural buffer that limits through-traffic and preserves the interior pond and walking-path system.
The location offers strong commuter access to two major thoroughfares: CR 535 heading north toward downtown Windermere and Winter Garden, and the SR 429 Western Beltway for fast access to Disney, the Turnpike, and points north and south. Disney's Magic Kingdom is roughly a 15-minute drive; Universal and SeaWorld are 20 minutes via I-4.
🏘️ Adjacent Neighborhoods & Areas
- North: Windermere Terrace
- South: Wetland conservation area
- East: Windermere Sound
- West: Wetland conservation area
- Nearby corridor: CR 535 (Winter Garden Vineland Road) with shopping, dining, and medical services minutes away
🚗 Detailed Commute Times
- Downtown Orlando: ~30 minutes (~19 miles)
- UCF Campus: ~40 minutes (~28 miles)
- Walt Disney World: ~15 minutes (~7 miles)
- Universal Orlando: ~20 minutes (~12 miles)
- SeaWorld Orlando: ~20 minutes (~10 miles)
- Disney Springs: ~15 minutes (~8 miles)
- Lake Nona Medical City: ~35 minutes (~25 miles)
- Cocoa Beach: ~70 minutes (~65 miles)
- Winter Garden Village: ~10 minutes (~5 miles)
✈️ Airport Access
- Orlando International Airport (MCO): ~30 minutes (~22 miles)
- Orlando Sanford International Airport (SFB): ~45 minutes (~38 miles)
- Orlando Executive Airport (ORL): ~30 minutes (~21 miles)
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Berkshire Park Amenities & Lifestyle
Berkshire Park is built around a family-oriented amenity package that's unusual for production-builder communities of its era. The central pool overlooks one of the larger interior ponds with a fountain, the cabana provides shaded seating and restrooms, and the fenced playground sits adjacent to the pool — a layout that lets parents supervise both at once. Walking paths trace the perimeter of the larger ponds, and the wetland buffers along the south and west sides keep the neighborhood quiet and visually green.
Day-to-day living leans on the CR 535 corridor: Cornerstone at Summerport sits a short drive north for groceries and services, Winter Garden Village handles bigger-box shopping and dining 5 miles away, and downtown Windermere's historic Town Square is reachable for events, the farmers market, and Friday-night gatherings.
🏊 Neighborhood Amenities
Amenities found within Berkshire Park:
- Community swimming pool with cabana and restrooms
- Fenced shaded playground (tot-lot)
- Multiple large interior ponds with fountains
- Walking paths along pond perimeters
- Wetland conservation buffers on the south and west sides
- Gated sub-community (Enclave at Berkshire Park)
- Pond-front and conservation-front homesites
🛍️ Shopping & Services
Cornerstone at Summerport on CR 535 is the closest neighborhood center for groceries, pharmacies, and everyday services. Winter Garden Village — an 80-store outdoor center — is a short drive north for big-box and apparel shopping, and The Mall at Millenia handles luxury retail roughly 15 minutes away.
For comprehensive shopping information: View our Windermere Shopping Guide →
🍽️ Restaurants
Casual and family dining clusters at The Grove at Isleworth, Lakeside Village, and Summerport centers on the CR 535 corridor. For date-night and waterfront tables, downtown Windermere's wine bars and romantic dining rooms are 10 minutes away. Sand Lake Road's Restaurant Row is the area's closest fine-dining corridor.
For comprehensive restaurant information: View our Windermere Restaurants Guide →
🎭 Arts & Culture
Downtown Windermere's Town Square hosts the annual Fine Art Show and the Isleworth Sculpture Collection (with works by Henry Moore, Dalí, and Philip Jackson) is open to the public. The Dr. Phillips Center for the Performing Arts in downtown Orlando is the closest major venue.
For comprehensive arts & culture information: View our Windermere Arts & Culture Guide →
🏃 Health & Wellness
Orlando Health Medical Pavilion Summerport is the closest multispecialty facility on CR 535 for imaging, labs, and primary care. Orlando Health Horizon West Hospital is the closest full-service hospital with ER and inpatient services, and Dr. P. Phillips Hospital is a short drive east.
For comprehensive health & wellness information: View our Windermere Health & Wellness Guide →
🌳 Parks & Recreation
R.D. Keene Park — 52 acres of soccer fields, playgrounds, and a public Butler Chain boat ramp — is roughly 3 miles away and is Windermere's flagship community park. Tibet-Butler Preserve on CR 535 offers 3.6 miles of nature trails, and Fernwood Park provides Lake Butler boat-ramp and pier access for residents who want Butler Chain recreation.
For comprehensive parks & recreation information: View our Windermere Parks & Recreation Guide →
⚽ Sports & Athletics
Butler Chain watersports — wakeboarding, water-skiing, and tubing — are accessible via the public ramps at R.D. Keene and Fernwood. Tennis and pickleball are available at town courts and private clubs, and LA Fitness Signature, Orangetheory, and boutique studios serve the 34786 ZIP. Premier golf is available nearby at Bay Hill Club & Lodge (PGA Tour host).
For comprehensive sports & athletics information: View our Windermere Sports & Athletics Guide →
🎉 Fun Things to Do
Downtown Windermere hosts the Friday-morning Farmers Market, monthly Food Truck Night at Town Square, and seasonal events like the Halloween Parade, PetFest, and Light Up Windermere. Walt Disney World, Universal Orlando, and SeaWorld are all 15–20 minutes away.
For comprehensive events & activities information: View our Windermere Events & Things To Do Guide →
🎓 Schools
Berkshire Park is served by Orange County Public Schools (OCPS):
- Elementary: Sunset Park Elementary
- Middle: Bridgewater Middle School (Horizon West Middle is also reported by some sources for nearby addresses — verify per parcel)
- High: West Orange High School (Windermere High School is also reported by some sources for nearby addresses — verify per parcel)
Note: Berkshire Park sits at the intersection of multiple OCPS attendance zones, and middle/high school assignments vary by sub-community and address. Always verify current zoning with the Orange County Public Schools attendance lookup tool using the specific parcel address before making purchase decisions.
For comprehensive school information: View our Windermere Schools Guide →
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How Berkshire Park Compares
Berkshire Park's value proposition becomes clearer alongside two common alternatives in the area: newer Horizon West master-planned communities (which carry CDD fees on top of HOA dues) and older established Windermere subdivisions without comparable amenity packages.
| Feature | Berkshire Park | Newer Horizon West Master-Planned | Older Established Windermere |
|---|---|---|---|
| Year Built | 2006 – 2014 | 2015 – 2026 | 1980s – early 2000s |
| CDD Fee | No | Yes (~$1,500 – $3,500/yr) | No |
| Community Pool | Yes | Yes (often resort-style) | Varies (often none) |
| Home Type Mix | Single-Family + Townhomes | Single-Family + Townhomes | Single-Family only (typical) |
| Tree/Pond Maturity | Established (12–20 yrs) | Newer plantings, less canopy | Mature canopy |
| Lot Size Profile | Modest – pond-front available | Modest production lots | Often larger (0.25 – 1+ acre) |
| 34786 ZIP / Windermere Address | Yes | Often Winter Garden / Orlando ZIPs | Yes |
💡 Value Proposition: Berkshire Park offers a Windermere 34786 address with a full amenity package (pool, cabana, playground, pond walking paths) and no CDD fee — at price points that often beat both newer Horizon West master-planned communities (which carry CDD assessments) and older Windermere subdivisions that lack comparable amenities. The mix of single-family and townhome inventory also gives families flexibility to enter the neighborhood at different price points and sizes.
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Berkshire Park HOA & CDD Information
Berkshire Park is governed by a homeowners association that maintains the central amenity area (pool, cabana, playground), the pond walking paths, the entry features, and the common landscaping. The HOA umbrella covers Berkshire Park, the Enclave at Berkshire Park, and Berkshire Place — though the gated Enclave sub-community has its own gate-access protocols on top of the shared amenities.
The neighborhood has no CDD (Community Development District) fee, which is a meaningful annual cost advantage versus newer master-planned communities in nearby Horizon West that typically carry CDD assessments of $1,500 – $3,500 or more per year on top of HOA dues.
💰 HOA Fees & Management Contact
HOA fees and management company information often change. Please contact us and we will be happy to provide you with the current HOA fee, payment schedule, and direct contact information for the HOA management company. We can also check for you to see if there are any current or upcoming special assessments.
📋 What HOA Fees Cover
- Community pool, cabana, and pool deck maintenance
- Playground equipment upkeep and safety inspections
- Common-area landscaping and entry features
- Pond fountain maintenance and walking-path upkeep
- Street lighting in common areas
- Architectural Review Board operations and standards enforcement
- HOA management company fees and reserve contributions
- General liability insurance for common areas
🔐 Enclave at Berkshire Park: Gated Sub-Community
The Enclave at Berkshire Park is a separately gated section within the broader Berkshire Park HOA, occupying the larger-lot, single-family portion of the neighborhood. Enclave residents access the same shared amenities (pool, cabana, playground, walking paths) as the rest of the community while benefiting from a gated entry and smaller cluster of homes. If gated security is a priority, ask your agent to filter listings specifically to the Enclave subdivision when searching Berkshire Park.
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David Myers
