Regal Oaks At Old Town Homes with Sidewalks Community Features

Regal Oaks At Old Town Homes with Sidewalks Community Features

Welcome to Regal Oaks at Old Town, a captivating subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This charming community is not just a place to live; it's a lifestyle that embraces comfort, convenience, and a sense of belonging.

Regal Oaks at Old Town boasts beautifully designed homes that cater to a variety of tastes and preferences. Each residence is thoughtfully crafted with modern amenities, spacious layouts, and inviting outdoor spaces, perfect for both relaxation and entertainment. One of the standout features of this community is its commitment to pedestrian-friendly living, with well-maintained sidewalks that encourage residents to take leisurely strolls, enjoy morning jogs, or simply connect with neighbors.

As you explore Regal Oaks, you'll find an array of community features that enhance the living experience. From lush green spaces to community parks, this subdivision fosters a sense of community and encourages an active lifestyle. The nearby Old Town entertainment district offers a delightful mix of shopping, dining, and entertainment options, ensuring that residents are never far from the action.

With its prime location in Kissimmee, Regal Oaks at Old Town provides easy access to major highways, world-renowned attractions like Walt Disney World, and the natural beauty of Central Florida's lakes and parks. Whether you’re seeking a family-friendly environment or a serene retreat, Regal Oaks at Old Town is the perfect place to call home. Discover the charm and warmth of this community, where every day feels like a vacation!

Newest Regal Oaks At Old Town Homes with Sidewalks Community Features

$270,000
2 Beds ⋅ 3 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code
Fully furnished 2-bedroom, 2.5-bath townhome in Regal Oaks Resort, conveniently located next to Old Town and minutes from Central Florida’s top attractions, shopping, dining, and entertainment. The home features a private rear setting with mature trees providing a natural privacy buffer from neighboring properties. The main level includes an open living and dining area, a well-appointed kitchen with stainless steel appliances and granite countertops, and convenient access to the outdoor living space. Upstairs, both bedrooms feature private en-suite bathrooms, making the layout ideal for both owners and guests. Regal Oaks offers resort-style amenities, including a pool complex, renovated ZAC’s Sports Bar & Grill, clubhouse, and more. Whether you’re looking for a vacation property, investment opportunity, or your own Central Florida getaway, this furnished townhome offers a convenient location within one of the area’s established resort communities.

2711 Coupe Street, Kissimmee
$364,900
3 Beds ⋅ 3 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code
Discover the Perfect Blend of Comfort, Style, and Investment Potential with this beautifully updated Corner-Unit townhome in Regal Oaks Resort, one of Central Florida's most sought-after Gated vacation rental communities. PRICED to SELL! Seller is offering up to $5,000 Incentive to Buyer's Closing Costs. Built during resort's newest phase, this rare 3 Bedroom End-unit townhome offers a more Contemporary Design and layout than many of the earlier homes in the community. Thoughtfully updated throughout, the home features Elegant Decorative Wood Accent Walls, Stylish Wallpaper, Upgraded Lighting, Modern Fixtures, Premium Faucets and Shower Systems, and beautiful Luxury Vinyl Flooring throughout the entire second floor and staircase, creating a Warm, Contemporary Atmosphere with exceptional durability and easy maintenance. Large windows throughout the home fill every living space with Abundant Natural Light, creating a Bright, Open, and Inviting atmosphere. The spacious open-concept floor plan seamlessly connects the living room, dining area, and kitchen, creating an inviting space for entertaining or relaxing after a day at the parks. The kitchen features Granite Countertops, Stainless-Steel GE Appliances and ample cabinet space. The laundry area includes a modern GE Washer and Dryer, while the home's GE appliances provide quality and consistency throughout the kitchen. Upstairs, the Spacious Owner's Suite overlooks the protected Conservation Area and offers a Private En-suite bathroom with dual vanities, a relaxing soaking garden tub, and peaceful preserve views. Two additional guest bedrooms and another full bathroom comfortably accommodate family and guests. The Screened Lanai provides a peaceful outdoor retreat overlooking the protected preserve, offering privacy with No Rear Neighbors. The home is being sold FULLY FURNISHED and tastefully DECORATED, making it completely Move-In Ready for personal enjoyment or immediate vacation rental use. Regal Oaks Resort offers an outstanding resort lifestyle with a beautiful Clubhouse, resort-style Swimming Pool with Water Slide, Fitness Center, Tennis Courts, Restaurant, Poolside Bar, Arcade, Scenic Lakes, Walking Trails, and 24-hr Guard-Gated security. Daily Valet Trash Collection, Exterior Maintenance, and Lawn Care are all included through the HOA, allowing owners to enjoy a truly low-maintenance ownership experience. Another valuable advantage is that Regal Oaks has no Community Development District (CDD) fees, helping reduce annual ownership costs compared to many competing resort communities. Ideally located in the heart of Kissimmee—Central Florida's Premier Destination for Vacation Homes—the property is approximately 9 miles from Disney Springs and offers convenient access to Walt Disney World, Universal Orlando Resort, Celebration, Sunset Walk, Margaritaville Resort Orlando, Island H2O Water Park, championship golf courses, shopping, dining, and I-4. This property is an established, income-producing vacation rental with an excellent rental history, Outstanding Guest Reviews & Future Reservations already in place. Subject to management continuity existing reservations may transfer to the new owner, allowing rental income to continue immediately after closing with $400 value photo package. Whether you're searching for a FL vacation home or a proven investment in one of Orlando's strongest vacation rental markets, this exceptional Regal Oaks property offers an outstanding opportunity.

2679 Corvette Lane, Kissimmee
$325,000
4 Beds ⋅ 4 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code
This 4-bedroom, 3.5-bath corner townhome is located in Regal Oaks Resort, a guard-gated, short-term rental-approved community in Kissimmee, FL; just 10 minutes from Disney World and Disney Springs, and a short drive to Universal Studios, SeaWorld, and other Orlando-area theme parks. Walking distance to Fun Spot and Old Town. The main floor includes a bedroom with ensuite bath, ideal for guests, in-laws, or multi-generational living. Upstairs offers a second ensuite bedroom plus two additional bedrooms — four bedrooms and 3.5 baths total. The open-concept floor plan connects the living and dining areas to a modern, fully equipped kitchen. Roof was replaced in 2023 and HVAC in 2019, giving buyers added peace of mind. Regal Oaks Resort amenities include a grand clubhouse with restaurant and bar, resort-style pool with water slide, pool bar and cabanas, fitness center, game room, tennis courts, and an on-site convenience store — resort-style living in a gated Kissimmee vacation rental community. Turnkey and fully furnished, this townhome is move-in ready as a primary residence, vacation home, or short-term/Airbnb rental investment property near Disney World. Schedule a private showing today.

2740 Coupe Street, Kissimmee
$290,000
3 Beds ⋅ 3 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code
Welcome to 2717 Bushman Drive, a turnkey, fully furnished vacation home in the highly sought-after Regal Oaks Resort at Old Town. Whether you're looking for a proven income-producing short-term rental, a vacation getaway, or a second home, this beautifully maintained 3-bedroom, 3-bath townhome is ready to go with existing future bookings already in place, allowing for a seamless transition to the next owner.Located just 13 minutes from Walt Disney World, this exceptional property is steps from the dining, shopping, and entertainment of Old Town Kissimmee and only minutes from the boutiques, restaurants, and year-round events of Downtown Celebration. This prime location continues to make Regal Oaks one of Central Florida's premier vacation destinations.Inside, you'll find an open-concept floor plan with a spacious living and dining area, a well-appointed kitchen with newer appliances, and three generously sized bedrooms. Offered fully furnished, this home is truly move-in or rental ready from day one. Step outside to your private screened lanai featuring a relaxing jacuzzi, the perfect place to unwind after a day at the parks.Owners and guests enjoy access to exceptional resort amenities including a stunning clubhouse, resort-style pool with waterslides, game room and arcade, fitness center, tennis and pickleball courts, on-site restaurant and poolside bar, market, and gated entry. With an unbeatable location, outstanding amenities, and immediate income potential, this is an exceptional opportunity to own a fully operational vacation rental in one of the Disney area's most desirable resort communities. Schedule your private showing today.

2717 Bushman Dr, Kissimmee
$295,000
4 Beds ⋅ 3 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code
Stunning 4 bedroom 3 bath townhome in the very popular gated community of Regal Oaks. Minutes from Walt Disney Resort, restaurants and shopping. Very quiet and private setting backing up to nature preserve. Open floor plan main floor with granite counter top kitchen, laundry and powder room. Freshly painted interior with accent walls. Turnkey furnished with contemporary furnishings. Fully equipped kitchen. Sliding doors to very private over sized lanai with heated hot tub. Second floor with 2 ensuite bedrooms and baths. Top of the line amenities with resort style zero entry pool, water slide, pool bar and cabanas. State of the art Clubhouse with restaurant, lounge, games room, fitness center, convenience store and tennis court. This stunning upgraded deluxe townhome is an investment opportunity in the highly sought-after gated community of Regal Oaks at Old Town. With professional property management already in place, it offers a hassle-free ownership experience and rental potential. Please note, this property is specifically tailored for investors seeking a rental asset. Located adjacent to Old Town and just a ten-minute drive to Walt Disney World Resort, this home combines a prime location with rental income prospects. The management team provides comprehensive services, including marketing, property upkeep, guest check-ins, thorough cleaning, communication, licensing, tourist taxes, insurance, and ongoing maintenance. The office is conveniently situated within the Clubhouse premises, ensuring seamless support and oversight. Additional support includes assistance with financial statements, current market analysis, and insights into the State of the Market, empowering you to make informed investment decisions. Don’t miss this opportunity to grow your real estate portfolio with a beautifully upgraded, professionally managed rental home in a prime Florida location. Contact us today to learn more!

2724 Coupe Street, Kissimmee
$276,000
2 Beds ⋅ 3 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code
Welcome to Regal Oaks Resort, one of Kissimmee's most desirable communities, ideally located next to Old Town and just minutes from Walt Disney World, shopping, dinning, and major attractions. this beautifully maintained 2 bedroom, 2.5 bath townhome is being sold fully furnished and is move in ready. One of the unique advantages of this property is its flexibility. Whether you are looking for a primary residence, a vacation home, a long term rental investment, or a short term vacation rental, this property offers endless possibilities. Unlike many resort communities, Regal Oaks allows owners to enjoy the home year round or take advantage of income producing rental opportunities. The home features an open and inviting floor plan, spacious bedrooms with private bathrooms, a convenient half bath on the main level, and tasteful furnishings throughout. Turnkey and ready for immediate occupancy or rental use, this property is an excellent opportunity to both homeowners and investors. Residents and guests enjoy resort style amenities including: guard gated 24/7, a community pool, water slides, clubhouse, restaurant, fitness center, tennis courts, and more. With its prime location in the heart of Central Florida's tourism corridor and the flexibility to fit a variety of lifestyles and investment goals, this is a rare opportunity you won't want to miss. Schedule your private showing today!

2670 Corvette Lane, Kissimmee
$267,000
2 Beds ⋅ 3 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code
Welcome to Regal Oaks Resort, where comfort, convenience, and resort-style living come together in this 2-bedroom, 2.5-bathroom townhouse. Offered fully furnished, this property is ready for immediate enjoyment as a vacation home, investment property, or personal retreat. Step inside to find a spacious and inviting open-concept layout designed for both relaxation and entertaining. The fully equipped kitchen flows seamlessly into the dining and living areas, creating the perfect gathering space for family and friends. One of the standout features of this home is the private west-facing lanai, providing sunny afternoons and stunning evening sunsets. Unwind after a day of adventure in your own private hot tub, an ideal space to relax and enjoy Florida's beautiful weather year-round. The upstairs level offers two generously sized bedrooms, each with its own ensuite bathroom, providing privacy and comfort for owners and guests alike. A convenient main-floor powder room adds additional functionality. Located just a short walk from Regal Oaks' resort amenities, residents and guests enjoy access to a community pool, clubhouse, fitness facilities, restaurant, and recreational areas. Situated minutes from world-famous attractions, shopping, dining, and entertainment, this location offers exceptional convenience while maintaining a peaceful resort atmosphere. Whether you're looking for a vacation getaway, income-producing property, or both, this fully furnished townhouse presents an outstanding opportunity in one of Central Florida's most desirable resort communities.

2606 Roadster Lane, Kissimmee
$313,000
2 Beds ⋅ 3 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code
Excellent investment opportunity in the gated resort-style community of Regal Oaks. This fully furnished 2-bedroom, 2.5-bath townhome is Airbnb-ready and has a strong history of successful short-term rental income. Ideally located near Disney, Old Town, and Fun Spot, this property consistently attracts vacationers looking for comfort, location, and resort amenities. Features include an open-concept floor plan, granite countertops, stainless steel appliances, tile flooring, private screened lanai with hot tub, and two spacious en-suite bedrooms. One of the most desirable locations in the community with peaceful courtyard and garden views. Regal Oaks offers resort-style amenities including a lakefront pool, water slides, hot tubs, tennis courts, fitness center, clubhouse, restaurant, and poolside bar. Turnkey investment with excellent income potential in one of Central Florida’s top vacation rental areas.

2665 Triumph Way, Kissimmee
$310,000
4 Beds ⋅ 4 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code
One or more photo(s) has been virtually staged. NEW PRICE and now offering $4,000 seller concessions!! SELLER MOTIVATED!! This is a spacious 4-bedroom, 3.5-bathroom townhome located in a highly sought-after resort-style community that offers the perfect blend of comfort, convenience, relaxation and opportunity to generate income. Whether you're looking for a primary residence, second home, or short-term rental investment this property checks all the boxes and is nestled within miles of Disney World, several family attractions, top-rated dining, shopping, and endless entertainment. In this guard gated community There are two Primary bedrooms each with its own en-suite bathroom. One the first level you'll find a functional layout designed for both everyday living and guest stays. The living/dining room combo is spacious and leads outside to your private screened-in patio featuring a relaxing above ground spa—perfect for unwinding for the weekend or hosting guests in your own outdoor retreat. Upstairs you'll find two additional bedrooms that are partially furnished and in closet laundry. Enjoy additional outdoor space with a private balcony located off the second Primary Bedrooms ideal for morning coffee or evening relaxation. Enjoy access to premium amenities including a resort-style pool, cabanas, fitness center, club house, on site restaurants, tennis and pickleball courts creating an unmatched vacation-style experience year-round.

2707 Camaro Drive, Kissimmee
$340,000
4 Beds ⋅ 3 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code
Turnkey, fully furnished 4-bedroom, 3-bathroom vacation townhome in the highly sought-after Regal Oaks Resort—one of the closest short-term rental communities to Walt Disney World Resort! Located in the heart of Kissimmee near Orlando’s top attractions, this income-producing property is ideal for Airbnb, VRBO, or personal use. Designed with both guests and owners in mind, this home features an open-concept layout with durable wood-look flooring, a bright kitchen with granite countertops, and a spacious living and dining area perfect for entertaining. The layout comfortably accommodates larger groups, making it highly desirable for vacation rentals in the Disney/Orlando market. A standout feature of this property is its professionally themed, Disney-inspired interior, creating a memorable guest experience that drives strong reviews and repeat bookings. The main level includes a bedroom and full bathroom, offering convenience and flexibility for multi-generational guests. Upstairs, the private primary suite provides a relaxing retreat, while additional themed bedrooms continue to elevate the home’s rental appeal in a competitive short-term rental market. Step outside to your private screened-in patio with hot tub, a premium amenity that enhances guest satisfaction and booking potential year-round. Located just minutes from Old Town Kissimmee and a short drive to Universal Orlando Resort and SeaWorld Orlando, this property offers unbeatable access to Central Florida’s most visited destinations, shopping, dining, and Orlando International Airport. Regal Oaks Resort amenities include a gated entrance, lakefront pool with water slides, fitness center, tennis courts, and on-site dining—making this one of the most desirable vacation rental communities in Kissimmee near Disney. Fully turnkey and has DOZENS OF BOOKINGS ALREADY IN PLACE THROUGHOUT 2026 AND BEYOND!—this is a rare opportunity to own a high-demand short-term rental in the Disney area with proven guest appeal.

2720 Roadster, Kissimmee
$350,000
4 Beds ⋅ 3 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code
TURNKEY SHORT-TERM RENTAL INVESTMENT OPPORTUNITY. Strategically located at 2759 Corvette Lane, this fully furnished vacation home is perfectly positioned in a highly desirable Kissimmee corridor, offering seamless access to Central Florida’s world-class theme parks, entertainment, and dining. Designed for immediate operational handover, the property is being sold fully equipped with all furnishings, appliances, and decor, making it a true turnkey asset ready to generate revenue from day one. Boasting a history of high turnover and consistent guest demand, this home represents an ideal portfolio addition for both seasoned investors and first-time vacation home buyers seeking a proven income-generating property. The layout and amenities are optimized for guest satisfaction and operational efficiency. Do not miss the opportunity to acquire a fully operational, revenue-ready asset in one of the nation's most robust short-term rental markets. All showings are strictly by appointment due to high occupancy rates.

2759 Corvette Lane, Kissimmee
$274,000
2 Beds ⋅ 3 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code
Welcome to your magical getaway in Regal Oaks Resort — a beautifully maintained 2-bedroom, 2.5-bath townhouse designed to delight theme park families while delivering solid rental performance. Property Highlights: - 2 Spacious Bedrooms | 2.5 Bathrooms - Newer Interior Paint & Carpet - Private, Oversized Lanai with Hot Tub - Serene Forested Backdrop with Abundant Wildlife - Whimsical Mouse-Themed Décor Throughout - Turnkey Investment with Established Management & Strong Booking History Step inside to discover a bright, refreshed interior with newer paint and plush carpeting upstairs. The open-concept living and dining area flows effortlessly to your private screened lanai, where guests unwind in the hot tub while enjoying peaceful conservation views — no rear neighbors, just nature and the occasional glimpse of the Florida deer. Upstairs, two generously sized bedrooms each with their own ensuite offers privacy and comfort. The playful Mouse-themed décor creates an unforgettable vacation experience for families visiting nearby theme parks, helping this property stand out in a competitive rental market and earn glowing guest reviews. Regal Oaks is one of the most sought-after vacation communities in the Kissimmee area — and here’s why: - Prime Location - Minutes from world-famous theme parks - Near shopping, dining, and entertainment - Easy access to major highways for seamless travel - Resort-Style Amenities - Gated community with 24-hour security - Resort-style pool with cabanas & water slides - On-site restaurant and bar - Fitness center & tennis courts - Strong Rental Demand - Highly desirable for short-term vacation rentals - Popular with domestic and international travelers - Family-friendly environment tailored to theme park guests - Proven Investment Performance This townhouse is fully turnkey with: ?? Established professional management in place ?? Solid booking history with repeat guests ?? Superior online booking status & reviews ?? Consistent occupancy driven by prime location and themed appeal** The thoughtful Mouse-inspired design, peaceful conservation lot, and private hot tub create a unique value proposition that maximizes nightly rates and occupancy.

2607 Corvette Lane, Kissimmee
Start Your Search