About Crestwood Heights Neighborhood
Crestwood Heights sits in one of Ocoee's most convenient pockets — directly off Montgomery Avenue, a short residential stretch running north of West Colonial Drive (SR 50) and immediately west of West Oaks Mall. The community is fully gated, giving a layer of privacy and security uncommon in townhome developments at this price point, and the interior streets are private with landscaping and exterior paint handled by the HOA.
The homes are classic mid-2000s Taylor Morrison production townhomes — two stories, stucco exteriors, attached two-car garages, and a mix of floor plans ranging from roughly 1,393 to 2,212 square feet. Most units are three-bedroom, two or two-and-a-half-bath layouts. A small subset of plans features a ground-floor primary suite, which is uncommon in this inventory and tends to move quickly when it hits the market. Rear-screened porches and enclosed lanais appear on many units, and garages face interior drives rather than the main streetscape.
What makes Crestwood Heights genuinely different from the rest of the townhome inventory in west Ocoee is the combination of three things: the gate, the pool and playground, and the location. You're walkable-to-drivable (depending on weather) to West Oaks Mall, minutes from Orlando Health – Health Central Hospital on West Colonial Drive, and one turn onto SR 429 away from Apopka, Winter Garden, or — via the Turnpike and SR 408 — downtown Orlando. For buyers prioritizing convenience and low-maintenance living over lot size or custom architecture, this is one of the strongest value propositions in the Ocoee market.
📊 Quick Facts
🏡 Home Features
- Attached two-car garages
- Open-concept main-floor living/dining/kitchen layouts
- Breakfast bar and dinette area in most kitchens
- Walk-in primary closets
- Rear screened or enclosed porches on many units
- Rare first-floor primary suite on select floor plans
- Stucco exteriors with HOA-managed repainting
- High ceilings on the main level in most plans
🔑 What Makes Crestwood Heights Different
- Gated townhome community: Gating is uncommon at this price tier in Ocoee's townhome inventory.
- Walk-level distance to West Oaks Mall: About a quarter-mile west of the mall and the broader SR 50 retail corridor.
- HOA-managed exteriors: Landscaping and exterior painting are handled by the association, which is genuinely low-maintenance ownership.
- Taylor Morrison construction: National builder product with consistent floor plans, not mixed-builder infill.
- No CDD fees: Unlike newer West Orange County townhome developments, Crestwood Heights carries no Community Development District assessment.
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Crestwood Heights Location & Connections
Crestwood Heights is positioned in west Ocoee, just north of West Colonial Drive (SR 50) and immediately west of West Oaks Mall. The address lands residents inside one of the city's busiest retail and medical corridors without being directly on it — the gated entrance sits on a quieter residential stretch of Montgomery Avenue, one block removed from the commercial frontage.
The community's immediate context is a mix of residential, commercial, and institutional uses. Ashton Park borders to one side, commercial frontage along West Colonial Drive (SR 50) borders to the south, and the Health Central Hospital campus sits a short drive east. SR 429 (the Western Beltway) is accessible within minutes via SR 50 for quick regional connections north to Apopka, south to Winter Garden, or onto Florida's Turnpike and SR 408 for downtown Orlando and theme park travel.
🏘️ Adjacent Neighborhoods & Areas
- Ashton Park neighborhood
- Commercial business frontage along West Colonial Drive (SR 50)
- Vacant land (future development parcels adjacent to the community)
- West Oaks Mall shopping area
- Montgomery Avenue residential corridor
- Orlando Health – Health Central Hospital area
🚗 Detailed Commute Times
- Downtown Orlando: Approximately 20 – 25 minutes via SR 408 (Arnold Palmer Expressway)
- UCF Campus: Approximately 35 – 40 minutes via SR 408
- Walt Disney World: Approximately 20 – 25 minutes via SR 429 and I-4
- Universal Orlando: Approximately 20 minutes via SR 408 and I-4
- SeaWorld Orlando: Approximately 25 minutes via SR 408 and International Drive
- Cocoa Beach: Approximately 70 – 80 minutes via SR 408 and SR 528
- Lake Nona Medical City: Approximately 35 – 40 minutes via SR 408
- Winter Garden: Approximately 8 – 12 minutes via SR 50 or SR 429
- Apopka: Approximately 15 – 20 minutes via SR 429
✈️ Airport Access
- Orlando International Airport (MCO): Approximately 30 – 35 minutes via SR 408 or Florida's Turnpike
- Orlando Sanford International Airport (SFB): Approximately 40 – 45 minutes via SR 429 and SR 417
- Orlando Executive Airport: Approximately 20 – 25 minutes via SR 408
🛣️ Highway & Expressway Access
- SR 429 (Western Beltway): Primary north-south toll connector — minutes away via SR 50
- Florida's Turnpike: Regional access for Miami, Tampa, and statewide travel
- SR 408 (Arnold Palmer Expressway): Fastest east-west route to downtown Orlando
- Highway 50 / West Colonial Drive: Ocoee's main commercial corridor, immediately south of the community
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Crestwood Heights Amenities & Lifestyle
Life in Crestwood Heights is built around convenience rather than amenities-on-site in the master-planned sense. Residents get a gated entry, a community pool, a playground, and HOA-handled exterior upkeep — the rest of daily life happens in the adjacent neighborhoods, at West Oaks Mall, along the West Colonial Drive corridor, and at the lakes and parks that define the broader Ocoee community.
The townhome format and the HOA structure make this a particularly strong fit for first-time buyers, downsizers, busy professionals, and anyone who values being close to shopping, dining, and medical care without taking on yard maintenance. The gated entry adds a layer of privacy most comparable townhome communities in the West Colonial corridor don't offer.
🏊 Neighborhood Amenities
Amenities found inside Crestwood Heights:
- Gated entry with limited-access community
- Community swimming pool
- Community playground
- HOA-managed exterior landscaping
- HOA-managed exterior painting on a scheduled rotation
- Private interior community roads
🛍️ Shopping & Services
West Oaks Mall sits approximately a quarter-mile east of the community, making it the closest major shopping destination. Additional everyday retail runs along the West Colonial Drive corridor, and Plantation Grove Shopping Center and Winter Garden Village are both within a short drive west.
For comprehensive shopping information: View our Ocoee Shopping Guide →
🍽️ Restaurants
The West Colonial Drive corridor just south of the community is Ocoee's densest restaurant strip, with everything from fast-casual chains to sit-down family restaurants. Toll Road Brewing Company and other Ocoee dining destinations are a short drive away.
For comprehensive restaurant information: View our Ocoee Restaurants Guide →
🎭 Arts & Culture
Ocoee's arts and culture scene is anchored in the historic downtown core — the Withers-Maguire House, the Ocoee Christian Church, and the Ocoee Lakeshore Center on Starke Lake — all reachable in a short drive from Crestwood Heights.
For comprehensive arts & culture information: View our Ocoee Arts & Culture Guide →
🏃 Health & Wellness
Crestwood Heights is exceptionally well-positioned for healthcare access. Orlando Health – Health Central Hospital — West Orange County's full-service medical anchor — sits a short drive east on West Colonial Drive, and the AdventHealth Ocoee ER provides a second 24/7 emergency option within the same corridor. AdventHealth Centra Care Ocoee handles urgent and primary care needs nearby.
For comprehensive health & wellness information: View our Ocoee Health & Wellness Guide →
🌳 Parks & Recreation
Bill Breeze Park on Starke Lake is Ocoee's civic living room and the primary public park for lakefront recreation, festivals, and community events. The West Orange Trail runs through Ocoee with a trailhead near downtown, and Vignetti Park is the city's flagship sports and recreation complex.
For comprehensive parks & recreation information: View our Ocoee Parks & Recreation Guide →
⚽ Sports & Athletics
Ocoee's sports infrastructure includes the city-owned Forest Lake Golf Club, the Jim Beech Recreation Center and Family Aquatic Center, and the forthcoming Dynasty Ocoee sports and entertainment complex.
For comprehensive sports & athletics information: View our Ocoee Sports & Athletics Guide →
🎉 Fun Things to Do
Food Truck Fridays and Movies in the Park at Bill Breeze Park anchor Ocoee's monthly community calendar, and the AMC Theaters at West Oaks Mall and independent West Orange Cinema on Maguire Road provide day-to-day entertainment options.
For comprehensive events & activities information: View our Ocoee Events & Things To Do Guide →
🎓 Schools
Crestwood Heights is likely served by:
- Elementary: Citrus Elementary (likely — verify with district)
- Middle: Ocoee Middle School (confirmed via OCPS zoning)
- High: Ocoee High School
Publisher note: Elementary school assignment for Crestwood Heights is based on geographic proximity and should be confirmed with Orange County Public Schools prior to publishing. School zoning boundaries are subject to change and should be verified at schoollocator.ocps.net for any specific address.
For comprehensive school information: View our Ocoee Schools Guide →
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How Crestwood Heights Compares
Crestwood Heights sits in a specific sub-segment of the Ocoee market: gated, low-maintenance townhomes under a national builder's consistent product line, with modest shared amenities and a strong retail-adjacent location. Benchmarking it against nearby townhome and single-family inventory helps clarify the trade-offs.
| Feature | Crestwood Heights | Villages at West Oaks | Wesmere (Townhome Sections) |
|---|---|---|---|
| Property Type | Gated townhomes | Townhomes / single-family | Master-planned mix |
| Year Built | 2006 – 2007 | Mid-2000s | Late 1990s – 2000s |
| Builder | Taylor Morrison | Production | Multiple |
| Gated | Yes | No | Selected sections |
| CDD Fee | No | No | No |
| Distance to West Oaks Mall | ~0.25 mile | Adjacent | ~1 – 2 miles |
| Exterior Maintenance | HOA-managed | Varies | Varies by section |
💡 Value Proposition: Crestwood Heights is one of the few gated townhome communities in the West Colonial Drive corridor, pairing builder-grade Taylor Morrison construction with HOA-managed exterior upkeep and a location within a quarter-mile of West Oaks Mall and Health Central Hospital. For buyers who want privacy, convenience, and low-maintenance ownership without a CDD fee, the trade-off of smaller footprints (versus single-family homes) and shared walls (versus detached homes) is compensated by a genuinely central west-Ocoee location.
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Crestwood Heights HOA & CDD Information
Crestwood Heights is governed by a mandatory homeowners association that handles substantial exterior maintenance — a structural feature of living in the community rather than an add-on benefit. The HOA maintains the gated entry, the community pool and playground, common-area landscaping, private community roads, and exterior painting on a scheduled rotation. This shifts meaningful ownership costs and effort from individual homeowners to the association, which is a defining characteristic of the community's value proposition.
Crestwood Heights does not carry a Community Development District (CDD) fee. Many newer West Orange County townhome developments — particularly those built after 2010 in Horizon West and parts of the SR 429 corridor — impose CDD assessments on top of HOA dues. The absence of a CDD here is a genuine cost advantage compared to newer inventory.
💰 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
- Gated entry maintenance and access control
- Community swimming pool upkeep and operations
- Community playground maintenance
- Common-area landscaping
- Private community road maintenance
- Exterior building painting on a scheduled rotation
- Common-area building insurance
- Reserve funding for long-term repairs and replacement
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David Myers
