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Home › Clermont › Westchester
📋 What's on This Page
  • About Westchester Neighborhood
  • Location & Connections
  • Neighborhood Amenities & Lifestyle
  • How Westchester Compares
  • HOA Information
  • Frequently Asked Questions
  • Available Homes

Westchester Homes for Sale

Clermont, FL 34714 | Established Neighborhood with Affordable Midsize Homes

Westchester is an established neighborhood in south Clermont, offering affordable midsize homes in a family-friendly community setting. Dating back to 1995, this neighborhood features well-maintained single-family homes ranging from 1,224 to 2,143 square feet on comfortable lots, providing excellent value for families, first-time buyers, and those seeking established neighborhoods with mature landscaping. View Available Homes

✓ Information verified current as of November 12, 2025

About Westchester Neighborhood

Westchester is situated in south Clermont in a well-established residential area that has been developing since 1995. The neighborhood features single-family homes built primarily in the mid-to-late 1990s and early 2000s, offering that sweet spot of established maturity with modern conveniences—homes old enough to have mature landscaping and tree canopy but young enough to have updated systems and contemporary floor plans.

The homes in Westchester range from approximately 1,224 to 2,143 square feet, primarily featuring 3-4 bedrooms and 2-2.5 bathrooms. This midsize range makes Westchester particularly attractive to families needing comfortable living space without the premium pricing of larger luxury homes. The neighborhood appeals to first-time buyers, growing families, and those seeking affordable housing in an established community with good schools and convenient access to employment centers.

Westchester's location in south Clermont provides residents with the benefits of suburban living while remaining connected to the region's major corridors. The neighborhood sits near Lake Louisa, one of Clermont's signature natural features, and benefits from proximity to conservation areas that preserve Florida's natural landscapes. Mature trees throughout the neighborhood create a pleasant canopy, and well-maintained homes reflect pride of ownership in this family-oriented community.

The established nature of Westchester means residents enjoy amenities like mature landscaping, established shade trees, and a sense of community that develops over decades. The neighborhood's affordability combined with its convenient location makes it an excellent value in the Clermont real estate market, particularly for buyers seeking move-in ready homes without the premium prices of brand-new construction.

📊 Quick Facts
Property Style(s):Single-family homes
Home Sizes:1,224 - 2,143 square feet
Bedrooms:Typically 3-4 bedrooms
Bathrooms:Typically 2-2.5 bathrooms
Year Built:1995-Early 2000s
HOA Fee:Contact us for current fee
CDD Fee:No (neighborhood predates CDD era)
Approximate Homes:Established residential neighborhood
Community Character:Mature landscaping, family-friendly, affordable
🏡 Home Characteristics

Typical homes in Westchester feature:

  • Split bedroom floor plans with master suite separation
  • Open-concept living areas with kitchen/family room flow
  • Two-car garages (most homes)
  • Covered front porches or entryways
  • Screened lanais or covered patios
  • Concrete block construction with stucco exteriors
  • Tile and carpet flooring (many updated to wood or luxury vinyl)
  • Inside laundry rooms
  • Comfortable lot sizes providing yards for play and relaxation
  • Some homes feature pools (check individual listings)
🌳 Established Neighborhood Benefits

Living in an established neighborhood like Westchester offers several advantages:

  • Mature tree canopy providing shade and curb appeal
  • Established landscaping with no waiting for plants to grow
  • Known neighborhood character and stable community
  • No CDD fees (major monthly savings vs. new construction)
  • Move-in ready homes avoiding 6-12 month construction wait
  • Lower purchase prices compared to brand-new homes
  • Stable home values in proven location
  • Existing school zones and established community services
  • Nearby amenities and infrastructure already in place

← Back to Top | View Available Homes →

Westchester Location & Connections

Westchester occupies a convenient location in south Clermont, positioned for easy access to the US-27 corridor and Highway 192. This strategic position places residents within minutes of Clermont's shopping, dining, and services along US-27 while providing quick connectivity to surrounding communities via Highway 192.

The neighborhood benefits from proximity to Lake Louisa and surrounding conservation areas, offering residents access to natural Florida landscapes and outdoor recreation. The location in south Clermont means shorter commutes to employment centers along the US-27 corridor and convenient access to both downtown Clermont's historic charm and newer commercial developments serving the growing region.

🏘️ Adjacent Neighborhoods & Areas
  • South Clermont area - Residential neighborhoods and developing commercial areas
  • Lake Louisa - Natural lake providing scenic views and recreation
  • Highway 27 (US-27) - Main commercial corridor with shopping and services
  • Highway 192 corridor - East-west connector to surrounding communities
  • Conservation areas - Preserved natural lands maintaining Florida ecosystems
🚗 Detailed Commute Times
  • Downtown Orlando: 40 minutes (30 miles via US-27 and Florida Turnpike)
  • Walt Disney World: 25 minutes (20 miles via Highway 192)
  • Universal Orlando: 35 minutes (28 miles via US-27)
  • SeaWorld Orlando: 32 minutes (25 miles via US-27)
  • Historic Downtown Clermont: 12 minutes (6 miles)
  • Winter Garden: 18 minutes (14 miles)
  • Lake Louisa State Park: 8 minutes (4 miles)
  • Davenport: 12 minutes (10 miles)
✈️ Airport Access
  • Orlando International Airport (MCO): 45 minutes (38 miles)
  • Orlando Sanford International Airport (SFB): 55 minutes (45 miles)

← Back to Top | View Available Homes →

Westchester Amenities & Lifestyle

Westchester offers the comfortable, established neighborhood lifestyle that appeals to families and homeowners seeking affordability without sacrificing convenience. The community's character reflects decades of stability—mature trees line the streets, well-maintained homes showcase pride of ownership, and neighbors know each other by name. This is classic Florida suburban living at its most accessible.

While Westchester doesn't feature extensive on-site amenities like newer master-planned communities, residents benefit from proximity to all of Clermont's public facilities, parks, and recreation areas. The lack of expensive amenity fees and CDD assessments translates to lower monthly costs, allowing families to enjoy Clermont's excellent public amenities without the premium pricing of resort-style communities. The neighborhood's location provides easy access to Lake Louisa State Park, Clermont's public facilities, and the region's commercial amenities.

🏡 Neighborhood Character

Westchester is characterized by:

  • Quiet residential streets with mature landscaping
  • Family-friendly atmosphere with children playing outdoors
  • Mix of original homeowners and newer residents
  • Well-maintained properties reflecting community pride
  • Established tree canopy providing shade and beauty
  • Safe, walkable streets for evening strolls
  • Sense of community built over decades
  • Convenient location without heavy traffic
🛍️ Shopping & Services

Westchester residents enjoy convenient access to comprehensive shopping along the US-27 corridor. Clermont Landing and Clermont Town Center provide Publix and Walmart Supercenter groceries, Target, Lowe's, and numerous retail stores, restaurants, and services all within 10-15 minutes.

For comprehensive shopping information: View our Clermont Shopping Guide →

🍽️ Restaurants

Dining options range from national chains along US-27 to unique local restaurants in Historic Downtown Clermont. Waterfront dining on Lake Minneola offers scenic views, and Montrose Street Market features local food vendors.

For comprehensive restaurant information: View our Clermont Restaurants Guide →

🎭 Arts & Culture

Cultural attractions include the Clermont Performing Arts Center with live performances, the Clermont Historic Village Museum, and the Clermont Arts & Recreation Center offering classes and programs for all ages.

For comprehensive arts & culture information: View our Clermont Arts & Culture Guide →

🏃 Health & Wellness

Medical facilities include Orlando Health South Lake Hospital, AdventHealth Clermont ER, UF Health ER & Urgent Care, and South Lake Hospital ER at Four Corners, providing comprehensive healthcare services for residents.

For comprehensive health & wellness information: View our Clermont Hospitals Guide →

🌳 Parks & Recreation

Westchester's location provides excellent access to outdoor recreation. Lake Louisa State Park offers camping, hiking, fishing, and kayaking. Clermont Waterfront Park features swimming beaches and waterfront activities. The South Lake Trail provides scenic paved paths for walking and biking.

For comprehensive parks & recreation information: View our Clermont Parks & Recreation Guide →

⚽ Sports & Athletics

The National Training Center where Olympic athletes train exemplifies Clermont's athletic culture. Golf courses include Legends Golf & Country Club, Green Valley Country Club, and Clermont National Golf Course. The Clermont Chain of Lakes provides fishing and watersports.

For comprehensive sports & athletics information: View our Clermont Sports & Athletics Guide →

🎉 Fun Things to Do

Attractions include the iconic Florida Citrus Tower, Lakeridge Winery & Vineyards for tastings, Showcase of Citrus for agritourism, and Southern Hill Farms for seasonal activities.

For comprehensive events & activities information: View our Clermont Events & Things To Do Guide →

🎓 Schools

Westchester is served by Lake County Public Schools:

  • Elementary: Pine Ridge Elementary or Grassy Lake Elementary
  • Middle: Windy Hill Middle School
  • High: Lake Minneola High School

Note: School assignments are subject to change. Always verify current zoning with Lake County Schools before purchasing.

Charter options include Imagine Schools at South Lake (K-8) and Pinecrest Lakes Academy (PK-8).

For comprehensive school information: View our Clermont Schools Guide →

← Back to Top | View Available Homes →

How Westchester Compares

Westchester offers exceptional value for buyers seeking established neighborhoods without the premium pricing and monthly fees associated with new construction. While newer communities come with resort-style amenities and contemporary features, they also carry significantly higher monthly costs through CDD fees, elevated HOA assessments, and premium purchase prices. Westchester provides comfortable, affordable living with mature landscaping and established community character at a fraction of the monthly cost.

The neighborhood appeals particularly to budget-conscious buyers, first-time homebuyers, and families who prefer to invest in location and savings rather than on-site amenities they may rarely use. By avoiding CDD fees alone, Westchester homeowners save $200-$400+ monthly compared to new construction communities—funds that can be invested in home improvements, family activities, or simply enjoying lower cost of living.

Feature Westchester New Construction Communities Older Neighborhoods (Pre-1990)
Year Built 1995-Early 2000s 2020-Present 1970s-1980s
Typical Home Size 1,224-2,143 sq ft 1,800-3,000+ sq ft 1,200-1,800 sq ft
Price Range Affordable (best value) Premium pricing Most affordable
CDD Fee No ($0/month savings) Yes ($200-$400+/month) No ($0/month savings)
Tree Canopy Mature (20-30 years) Newly planted or none Very mature (40+ years)
Landscaping Established and mature New plantings Very mature
Move-In Timeline Immediate 6-12 months (build time) Immediate
Amenity Center Use public facilities Resort-style (high HOA) Limited or none
Home Condition Well-maintained, move-in ready Brand new May need updates
Monthly Costs Low (no CDD, lower HOA) High (CDD + elevated HOA) Lowest (minimal HOA)

💡 Value Proposition: Westchester delivers the sweet spot of established neighborhood living—homes new enough for modern systems and layouts, old enough for mature landscaping and no CDD fees. Save $200-$400+ monthly compared to new construction while enjoying immediate move-in availability and proven neighborhood character.

← Back to Top | View Available Homes →

Westchester HOA & CDD Information

Westchester homeowners benefit from the neighborhood's established status with modest HOA fees covering essential common area maintenance and neighborhood upkeep. Unlike newer communities with extensive amenity centers and high monthly costs, Westchester focuses on core services maintaining property values and neighborhood appearance without the premium pricing of resort-style developments.

A significant advantage of Westchester is the absence of Community Development District (CDD) fees. Since the neighborhood was developed in the 1990s before the CDD financing model became common, homeowners save $200-$400+ monthly compared to new construction communities with CDD assessments. This monthly savings over the life of homeownership represents tens of thousands of dollars that stay in your pocket rather than paying off infrastructure bonds.

💰 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 Typically Cover
  • Common area landscaping and maintenance
  • Entrance signage and landscaping upkeep
  • Street lighting in common areas
  • General liability insurance for common areas
  • HOA management and administrative services
  • Reserve fund contributions for future repairs
  • Covenant enforcement ensuring neighborhood standards

Note: Westchester does not have extensive amenity facilities like pools or clubhouses, resulting in lower HOA fees compared to resort-style communities.

✅ No CDD Fees - Major Savings

Westchester has NO CDD fees, providing significant monthly savings compared to newer communities:

  • Save $200-$400+ monthly vs. typical new construction CDDs
  • Save $48,000-$96,000+ over 20 years of homeownership
  • No complex CDD bond prepayment decisions at closing
  • Simpler property tax bills without CDD assessments
  • Lower overall monthly housing costs

This represents one of Westchester's most significant financial advantages—keeping more money in your pocket every single month of homeownership.

← Back to Top | View Available Homes →

Frequently Asked Questions

What is the HOA fee in Westchester?
Please contact us for the current HOA fee, payment schedule, and HOA management company contact information. Westchester HOA fees are typically modest compared to newer communities, covering common area maintenance, landscaping, entrance upkeep, and administrative services without expensive amenity facilities.
Does Westchester have CDD fees?
No, Westchester has NO CDD fees. The neighborhood was developed in 1995 before the CDD financing model became common in Florida. This means homeowners save $200-$400+ monthly compared to newer communities with CDD assessments—a savings of $48,000-$96,000+ over 20 years of homeownership.
What schools serve Westchester?
Westchester is served by Lake County Public Schools including Pine Ridge Elementary or Grassy Lake Elementary, Windy Hill Middle School, and Lake Minneola High School. Charter options include Imagine Schools at South Lake (K-8) and Pinecrest Lakes Academy (PK-8). Always verify current school assignments with Lake County Schools before purchasing, as attendance zones may change.
When were homes in Westchester built?
Westchester homes were primarily built from 1995 through the early 2000s. This makes them new enough to have contemporary floor plans and relatively modern systems, while being old enough to feature mature landscaping, established tree canopy, and no CDD fees. It's the ideal balance of established character with functional modern living.
What size are homes in Westchester?
Homes in Westchester typically range from approximately 1,224 to 2,143 square feet, featuring 3-4 bedrooms and 2-2.5 bathrooms. This midsize range provides comfortable family living space without the premium pricing of larger luxury homes, making Westchester particularly attractive to first-time buyers and growing families.
How does Westchester compare to new construction communities?
Westchester offers significant advantages including immediate move-in availability (no 6-12 month wait), no CDD fees (save $200-$400+ monthly), mature landscaping and tree canopy, lower purchase prices, and established neighborhood character. While new construction offers brand-new homes and modern amenities, Westchester provides exceptional value with lower monthly costs and move-in ready homes in a proven location.
Does Westchester have a pool or clubhouse?
Westchester does not have on-site amenity facilities like pools or clubhouses, which is one reason for the lower HOA fees. However, residents have access to all of Clermont's excellent public parks, the Clermont Arts & Recreation Center, Lake Louisa State Park, Clermont Waterfront Park, and numerous other public facilities without paying for private amenities they may rarely use.
Is Westchester a good neighborhood for first-time buyers?
Yes, Westchester is excellent for first-time buyers due to affordable pricing, no CDD fees, modest HOA costs, comfortable home sizes, established neighborhood character, move-in ready homes, and good school zones. The combination of affordability, convenience, and established community makes Westchester one of the best values for first-time buyers in the Clermont area.

 

Available Homes in Westchester

Below are currently available listings in Westchester. This established neighborhood offers move-in ready homes without construction delays. Create a custom search for instant alerts when new homes become available.

Westchester Homes for Sale

15937 Wilkinson Drive, Clermont image
15937 Wilkinson Drive, Clermont $378,500

Welcome to this beautifully maintained one-story, 4-bedroom, 2-bathroom home offering comfort, privacy, and a functional open layout. Freshly repainted throughout, this m...

  • 4 Beds
  • 2 Baths
  • Westchester Ph 06 07 SubDv.
  • 34714 Zip Code
16249 Wilkinson Drive, Clermont image
16249 Wilkinson Drive, Clermont $378,900 ▼

Virtually Staged. Welcome to this beautifully updated 4-bedroom home situated on a desirable corner lot in Clermont! Perfectly positioned to overlook a spacious green spa...

  • 4 Beds
  • 3 Baths
  • Westchester Ph 05 SubDv.
  • 34714 Zip Code
1746 Westminster Trail, Clermont image
1746 Westminster Trail, Clermont $325,000 ▼

Welcome home to this move-in ready 3-bedroom, 2-bath home in one of Clermont’s most convenient locations - just minutes from US-27 with quick access to Highway 192, shopp...

  • 3 Beds
  • 2 Baths
  • Westchester Ph 03 SubDv.
  • 34714 Zip Code
1614 Herring Lane, Clermont image
1614 Herring Lane, Clermont $359,900 ▼

Virtually Staged. Welcome to this beautifully maintained 4-bedroom, 2.5-bath home with a versatile flex room that can easily serve as a 5th bedroom, office, or playroom. ...

  • 4 Beds
  • 3 Baths
  • Westchester Ph 06 07 SubDv.
  • 34714 Zip Code
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