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Country Crossing Homes for Sale

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

Country Crossing Homes for Sale

Kissimmee, FL 34744 | Established Single-Family Neighborhood on the North Kissimmee / BVL Border

Country Crossing is a small, established single-family neighborhood in the 34744 ZIP code of north Kissimmee, positioned at the boundary between Kissimmee proper and the Buenaventura Lakes community along the Simpson Road and Fortune Road corridors. Developed in the early 1990s, this compact neighborhood offers traditional Florida ranch-style homes on quarter-acre lots with the kind of quiet residential atmosphere that comes from a well-settled, owner-occupied community. For buyers looking for an accessible, no-frills address in Kissimmee with strong highway connectivity, Country Crossing is worth a close look. View Available Homes

✔ Information verified current as of April 2026

About Country Crossing Neighborhood

Country Crossing is a small, established residential subdivision located in the 34744 ZIP code of north Kissimmee, tucked between Simpson Road to the north and Fortune Road to the south. The neighborhood was developed in the early 1990s — homes are documented built in 1992 and 1993 — making Country Crossing one of the earlier residential communities established in this particular corridor of Osceola County. Access is from Country Crossing Court, a residential street entered from Simpson Road just west of Fortune Road.

Homes in Country Crossing are single-story concrete block construction in the traditional Florida ranch style. They are modest in square footage — typically running 1,000 to 1,300 square feet of living area — but sit on generous 0.25-acre lots that provide meaningful backyard space, a rarity in today's tight-lot developments. With 3 bedrooms and 2 bathrooms as the standard layout, the homes are right-sized for first-time buyers, small families, downsizers, and investors seeking a stable, well-located Kissimmee property.

The neighborhood's position on the border of the established Buenaventura Lakes (BVL) community to the north gives Country Crossing residents access to BVL's broader amenity network while residing within the Kissimmee 34744 ZIP code. The Florida Turnpike corridor runs nearby, and US Highway 192 (Irlo Bronson Memorial Highway) is accessible within a short drive, connecting residents to the full sweep of Kissimmee's commercial and employment corridors. Parsons Pond neighborhood lies adjacent, and the broader north Kissimmee / BVL area is one of the more established and affordable residential markets in Osceola County.

📊 Quick Facts
Property Style(s):Single-Family Homes (concrete block, single-story)
Home Sizes:Approximately 991–1,304 sq ft (living area)
Bedrooms:Typically 3 bedrooms
Bathrooms:Typically 2 bathrooms
Lot Sizes:Approximately 0.25 acres (±10,890 sq ft)
Year Built:1992–1993
HOA Fee:Contact us for current information
CDD Fee:No
ZIP Code:34744
🏡 Home Character & Construction

Country Crossing's homes reflect the solid, practical construction standards of early 1990s Florida residential development. Single-story concrete block layouts with attached garages, traditional floor plans, and quarter-acre lots give each home a sense of space and privacy that is uncommon in modern Kissimmee developments. Many homes have been maintained and updated by long-term owners, and the neighborhood carries the feel of a stable, owner-occupied community rather than an investor-heavy subdivision.

📍 BVL Border Location Advantage

Country Crossing's position at the north Kissimmee / Buenaventura Lakes border gives residents convenient access to BVL's extensive commercial corridor along US 192, including grocery stores, pharmacies, restaurants, and professional services. The Parsons Pond neighborhood lies directly adjacent, and the Florida Turnpike is accessible within a few minutes for regional commuting in any direction.

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Country Crossing Location & Connections

Country Crossing is located in Kissimmee's north 34744 corridor, directly at the boundary with the Buenaventura Lakes (BVL) community. The neighborhood is accessed from Simpson Road — which runs east-west through this stretch of north Kissimmee — just west of Fortune Road. This specific location puts residents at a natural geographic crossroads: within the Kissimmee city area for school and municipal services, yet immediately adjacent to BVL's well-established commercial and residential fabric.

US Highway 192 (Irlo Bronson Memorial Highway) is nearby to the south, providing access to Kissimmee's main commercial corridor and connections toward Walt Disney World to the west. The Florida Turnpike corridor runs to the east, with ramp access connecting residents to Orlando International Airport (roughly 15–20 minutes north), Lake Nona Medical City, and points south toward Polk County.

🏘️ Adjacent Neighborhoods & Areas
  • Buenaventura Lakes (BVL) — Large established community directly to the north, sharing the US 192 commercial corridor
  • Parsons Pond — Adjacent neighborhood along the Fortune Road / Simpson Road intersection area
  • Simpson Road corridor — Primary east-west access route through north Kissimmee connecting to US 192
  • US Highway 192 / Irlo Bronson Memorial Highway corridor — Major commercial spine to the south with retail, dining, and services
  • Florida's Turnpike corridor — Regional highway to the east providing fast connections to MCO, Lake Nona, and Orlando
🚗 Detailed Commute Times
  • Downtown Orlando: Approximately 30–35 minutes (27 miles via Florida Turnpike north)
  • UCF Campus: Approximately 30–35 minutes (28 miles via Turnpike and SR 417)
  • Walt Disney World: Approximately 20–25 minutes (18 miles via US 192 west or Turnpike)
  • Universal Orlando: Approximately 25–30 minutes (24 miles via Turnpike north)
  • SeaWorld Orlando: Approximately 20–25 minutes (19 miles via Turnpike)
  • Cocoa Beach: Approximately 60–70 minutes (60 miles via Turnpike and SR 528)
  • Lake Nona Medical City: Approximately 15–20 minutes (14 miles via Turnpike north to SR 417)
  • Downtown Kissimmee: Approximately 8–12 minutes (6 miles via US 192 or Simpson Road)
  • St. Cloud: Approximately 15–18 minutes (13 miles via US 192 east)
✈️ Airport Access
  • Orlando International Airport (MCO): Approximately 15–20 minutes (14 miles via Florida Turnpike north)
  • Orlando Sanford International Airport (SFB): Approximately 45–55 minutes (42 miles via Turnpike and SR 417)
  • Kissimmee Gateway Airport (ISM): Approximately 10–14 minutes (8 miles via US 192 west)

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Country Crossing Amenities & Lifestyle

Country Crossing's lifestyle is shaped by its north Kissimmee location and its proximity to the Buenaventura Lakes community — one of the most well-established residential areas in Osceola County. Residents have immediate access to BVL's commercial fabric along Kissimmee's US 192 corridor, where grocery stores, pharmacies, restaurants, medical offices, and everyday services are concentrated within a short drive. The neighborhood itself is quiet and residential, with the calm that comes from a settled, owner-occupied community.

The Turnpike's proximity means that while Country Crossing is an understated, no-frills neighborhood by design, it is anything but isolated. Orlando International Airport is roughly 15–20 minutes away — among the shortest airport commutes of any established Kissimmee neighborhood. Walt Disney World, Universal, and SeaWorld are all 20–30 minutes via the Turnpike or US 192, making this a practical base for theme park employment or leisure.

🏊 Neighborhood Amenities

Country Crossing is a small single-family neighborhood without a formal community amenity complex. There is no community pool, clubhouse, or managed recreation facility within the subdivision itself. Residents benefit from the quarter-acre lots that provide private outdoor space, and the surrounding BVL and north Kissimmee area offers extensive community amenities nearby.

🛍️ Shopping & Services

The US 192 corridor and Simpson Road commercial areas provide immediate access to Publix, Walmart, Walgreens, and a range of national and local retailers. The Loop Shopping Center on John Young Parkway is accessible within 15–20 minutes for additional retail. BVL's commercial strip adds further convenience directly north.

For comprehensive shopping information: View our Kissimmee Shopping Guide →

🍽️ Restaurants

The north Kissimmee / BVL corridor along US 192 delivers an especially rich dining landscape, with extensive Latin cuisine options — Cuban, Venezuelan, Puerto Rican — alongside family restaurants, fast casual chains, and local independents that reflect Kissimmee's diverse community character.

For comprehensive restaurant information: View our Kissimmee Restaurants Guide →

🎭 Arts & Culture

Osceola Arts serves as Kissimmee's primary performing arts venue, offering live theater, concerts, and community programming. The Pioneer Village at Shingle Creek and the Osceola County Welcome Center & History Museum provide cultural depth within short driving distance.

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

🏃 Health & Wellness

AdventHealth Kissimmee and HCA Florida Osceola Hospital are both within 15–20 minutes of Country Crossing. Numerous urgent care clinics, medical offices, and specialty providers are distributed along the US 192 corridor and Simpson Road area, providing comprehensive healthcare access for 34744 residents.

For comprehensive health & wellness information: View our Kissimmee Health & Wellness Guide →

🌳 Parks & Recreation

Kissimmee Lakefront Park on Lake Tohopekaliga — with its marina, boardwalk, and event space — is approximately 10–12 minutes away. Shingle Creek Regional Park offers kayaking and wildlife viewing, and the broader Kissimmee park system includes splash pads, athletic fields, and community centers throughout the 34744 area.

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

⚽ Sports & Athletics

The Bob Makinson Aquatic Center provides competitive swimming and aquatic recreation within the Kissimmee park system. Youth sports leagues through Osceola County Parks & Recreation operate fields and courts throughout the 34744 ZIP code. Golf options include Falcon's Fire Golf Club and Kissimmee Bay Country Club for golfers in the area.

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

🎉 Fun Things to Do

Gatorland — the Alligator Capital of the World — is among Kissimmee's most beloved attractions and is accessible in about 15 minutes. Old Town Kissimmee with its retro rides and classic car shows is nearby on US 192. Walt Disney World, Universal, and SeaWorld are all within easy reach for day trips or regular theme park commuting.

For comprehensive entertainment information: View our Kissimmee Entertainment Guide →

🎓 Schools

Country Crossing is served by Osceola County School District. Zoned schools include:

  • Elementary: Ventura Elementary School
  • Middle: Parkway Middle School
  • High: Gateway High School or Tohopekaliga High School — verify current assignment with Osceola County School District, as high school boundaries in the north Kissimmee / BVL corridor have been subject to change

Note: School assignments are subject to change. Always verify current zoning directly with the Osceola County School District before purchasing.

For comprehensive school information: View our Kissimmee Schools & Education Guide →

↑ Back to Top | View Available Homes →

How Country Crossing Compares

Country Crossing occupies a specific niche in the north Kissimmee / BVL market: small, established homes on generous quarter-acre lots in a location with exceptional highway access and no HOA-level overhead — all at entry-level price points that are increasingly rare in this part of Osceola County. For first-time buyers and investors seeking stable, affordable Kissimmee properties with strong commute access, Country Crossing checks meaningful boxes.

Feature Country Crossing Parsons Pond BVL Area (typical)
Typical Home Size ~991–1,304 sq ft ~1,200–1,700 sq ft ~1,100–1,600 sq ft
Typical Lot Size ~0.25 acres ~0.15–0.20 acres ~0.12–0.18 acres
Year Built 1992–1993 1990s–2000s 1980s–1990s
CDD Fee No No No
MCO Airport Access ~15–20 min ~15–20 min ~20–25 min
US 192 / BVL Access Excellent (border location) Good Excellent

💡 Value Proposition: Country Crossing offers some of the best Turnpike and airport access of any small established neighborhood in the 34744 ZIP code, at entry-level price points with quarter-acre lots and no CDD fee — a practical combination that's difficult to replicate in today's new construction market.

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Country Crossing HOA & CDD Information

Country Crossing is a small established neighborhood, and HOA status should be verified for specific properties. The neighborhood was developed in the early 1990s in a period when small Kissimmee subdivisions were commonly platted with minimal or no association structure. There is no Community Development District (CDD) fee in Country Crossing. For a background on CDDs and how they affect homeowners, see our guide: What's a CDD?

For buyers who want to understand the HOA structure — if any — for a specific Country Crossing home, our team can research the recorded documents and provide current information. Please contact us and we will be happy to help clarify what, if any, association obligations apply to a specific property.

💰 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 (if applicable), 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. For more information on how HOAs work generally, see: What's an HOA?

📋 CDD Status
  • Country Crossing does not have a Community Development District (CDD)
  • No CDD assessments are added to property tax bills
  • This distinguishes Country Crossing from newer Kissimmee master-planned communities where CDD fees can add $1,500–$3,000+ annually to ownership costs

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Frequently Asked Questions

What is the HOA fee for Country Crossing?
Please contact us for current HOA fee information, payment schedule, and HOA management company contact details if applicable. Country Crossing is a small early-1990s subdivision and HOA structure should be verified for individual properties. We can research recorded documents and provide accurate, current information before you make any purchasing decisions.
Is there a CDD fee in Country Crossing?
No, Country Crossing does not have a Community Development District (CDD) fee. This is a meaningful advantage over many newer Kissimmee master-planned communities where CDD assessments can add $1,500 to $3,000 or more annually to property tax bills. For background on what CDDs are and how they work, see our guide: What's a CDD?
What schools serve Country Crossing?
Country Crossing is served by Osceola County School District. Typical zoned schools for this area are Ventura Elementary, Parkway Middle School, and either Gateway High School or Tohopekaliga High School. High school boundary assignments in the north Kissimmee / BVL corridor have been subject to change, so always verify the current assignment directly with Osceola County School District before purchasing. Visit our Kissimmee schools guide for more detail.
How close is Country Crossing to Orlando International Airport?
Country Crossing is approximately 15–20 minutes from Orlando International Airport (MCO), roughly 14 miles via the Florida Turnpike north. This is among the shortest airport commutes of any established Kissimmee neighborhood, making Country Crossing a practical choice for airport employees, frequent business travelers, and anyone who values fast MCO access.
Where exactly is Country Crossing located in Kissimmee?
Country Crossing is located in north Kissimmee's 34744 ZIP code, accessed from Country Crossing Court off Simpson Road, just west of Fortune Road. The neighborhood sits at the border of Kissimmee proper and the Buenaventura Lakes (BVL) community, with US 192 to the south and the Florida Turnpike accessible to the east. It is a quiet cul-de-sac community tucked between these major corridors.
When were homes in Country Crossing built?
Homes in Country Crossing were built primarily in 1992 and 1993, making this an early-1990s established neighborhood. The homes are single-story concrete block construction on approximately quarter-acre lots, and many have been maintained and updated by long-term owners over the past 30+ years.
How big are the homes in Country Crossing?
Homes in Country Crossing typically offer 991 to 1,304 square feet of living area, with 3 bedrooms and 2 bathrooms as the standard configuration. While modest in square footage by current standards, the homes sit on approximately 0.25-acre lots, providing generous outdoor space that significantly enhances the overall livability and privacy of each property.
Is Country Crossing close to Walt Disney World?
Yes — Walt Disney World is approximately 20–25 minutes from Country Crossing via US 192 west or the Florida Turnpike. This makes Country Crossing a realistic commuter base for the tens of thousands of Osceola County residents employed at the Walt Disney World complex, while offering significantly more affordable home prices than west Kissimmee resort corridor neighborhoods.
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