Crestwynd Bay Homes for Sale in Kissimmee - 9 homes

Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to this beautifully updated 3-bed 3-bath townhome located in the desirable gated community of Crestwynd Bay in Kissimmee—where modern upgrades, prime location, and investment potential come together. One bedroom downstaris. Property Highlights: HOA fee includes TV Cable and internet Fully renovated interior with stylish laminate flooring throughout Newly redo the vinyl stairs New Modern kitchen featuring new cabinetry and elegant quartz countertops Fresh interior paint for a bright, clean look in natrul color Flexible floor plan with a first-floor bedroom and full bath—ideal for guests, in-laws, or multi-generational living Recent upgrades (2026): New refrigerator, dishwasher, and water heater Updated bathroom lighting and fixtures Community Features: Secure gated access Resort-style amenities including pool, playground, and scenic walking trails HOA covers exterior maintenance, cable, internet, and trash service—offering truly low-maintenance ownership Unbeatable Location: Less than 2 miles to Walt Disney World Minutes to US-192, with easy access to I-4 and 429 Close to world-class golf, shopping, dining, and entertainment Investment Opportunity: Zoned for short-term and long-term rentals—perfect as a primary residence, vacation home, or income-producing property Live, vacation, or invest in one of Central Florida’s most sought-after areas. Schedule your private showing today and start enjoying the Florida lifestyle!

Listing is courtesy of: GOLDEN SUN REALTY INC (407-479-8898)

Listing Agent: Lucia Wu (407-765-2618)

Remarks: Beautifully and updated fully furnished and equipped  3-bedroom, 3 full-bath townhome located in the gated community of Crestwynd Bay in KissimmeeFully Furnished townhome equipped with smart locks and thermostat with alarm system, corian counters with 42 inches cabinets. One bedroom with Full bathroom located on the first floor. All  bedrooms and living room  equipped with smart TV. Residents of Crestwynd Bay can enjoy resort-style amenities, including a community pool,  playground, Clubhouse. The HOA includes exterior maintenance, internet, cable, and trash service. The property is Approved for short-term and long-term rentals, making it a great option for a primary residence, vacation home, or investment property.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Nataliya Voroshylo Hylton (407-284-7247)

Remarks: Click the Virtual Tour link to view the 3D walkthrough. Welcome to this inviting townhouse featuring a functional and well-designed floor plan. The first floor offers a comfortable living area that flows seamlessly into the kitchen and dining space, creating an ideal setting for everyday living and entertaining. A convenient first-floor bedroom is located adjacent to a full bathroom, providing flexibility for guests, a home office, or multi-generational living. Upstairs, you'll find the spacious primary suite complete with a private full bathroom, along with an additional secondary bedroom. With its versatile layout and comfortable living spaces, this townhouse is ready for its next owner. Don't miss the opportunity to make it yours! Discounted rate options and no lender fee future refinancing may be available for qualified buyers of this home.

Listing is courtesy of: ORCHARD BROKERAGE, LLC (844-515-9880)

Listing Agent: Farid Premjee (407-283-7770)

Remarks: Beautiful end-unit Townhome located in a gated Community just 2.5 miles from Walt Disney World, and minutes from major highways I4 and Hwy 192 offering easy access to shopping, dining, attractions, resorts, and Walmart. This is the largest 3 bedroom 2 bath townhome in Crestwynd Bay that was offered by KB Homes. Perfect for both primary homeowners or investors. This unit is zoned for A rated Celebration School and can be used for primary, long term, or short term rental, which makes this the ideal place to call home or your home away from home. The flooring consists of tile in the wet areas and laminate first floor while the second floor carpet throughout. The kitchen offers 42 inch cabinets including hardware and crown molding. Marble kitchen countertops with matching color appliances. The open-concept living room flows seamlessly into the kitchen, creating an ideal space for entertaining. All bedrooms are located on the second floor a spacious primary suite with jacuzzi tub and shower combo. Community amenities include a pool and playground. schedule your private showing now. the seller will give credit to the buyer for the closing cost.

Listing is courtesy of: FLORIDA HOMES REALTY & MORTGAGE (904-996-9115)

Listing Agent: Jimmy Elkhatib (407-446-2573)

Remarks: Townhouse for sale in the gated community of Crestwynd Bay in Kissimmee. This property features 3 bedrooms, 2.5 bathrooms, and 1,595 square feet of heated living space, offering one of the larger floor plans within the community. Its functional layout provides comfortable living areas, making it a great option for buyers looking for a primary residence, second home, or a property with investment potential in a strategic Central Florida location. One of the key value points is the newer A/C system installed in 2025/2026, along with improvements to the ventilation ducts, representing an important benefit for the future buyer by helping reduce one of the major maintenance concerns. The property is currently tenant-occupied, with a lease in place through September 30, 2026. This offers flexibility for buyers planning future occupancy, as well as for those who may value a property with active occupancy at the time of purchase. Continued occupancy after that date may be considered based on terms agreed upon by the parties. Crestwynd Bay offers a convenient location near major roads, shopping, dining, entertainment, and Central Florida’s world-famous attractions. Seller is open to reasonable negotiations. Buyer and buyer’s agent are responsible for verifying all HOA information, community restrictions, room measurements, lease terms, association approval requirements, and any other information deemed important.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Alicia Graterol Roa (407-485-7902)

Remarks: Under contract-accepting backup offers. Short Sale. Fantastic Opportunity to Own a 3-Bedroom, 3-Bathroom Townhouse! Located in the desirable gated community of Crestwynd Bay, this stunning townhouse has an open-concept downstairs which includes the living room, kitchen, one bedroom and a full bath on the first floor. The primary bedroom on the second floor has a full ensuite bathroom. The second floor offers a third bedroom and a third full bathroom. Enjoy the peace and privacy of a gated community with a pool and playground. The HOA fee includes internet and cable. Additionally, it’s conveniently situated near a variety of shopping, dining, and entertainment options including Walt Disney World, Universal Studios, SeaWorld ensuring that guests or future tenants have everything they need. Whether you’re looking for a tranquil home, a vacation home, a long-term rental investment, or a short-term rental investment, this property has all the possibilities.

Listing is courtesy of: TURNKEY HOMES REAL ESTATE CORP (347-223-2883)

Listing Agent: Tabatha Ramos (347-223-2883)

Remarks: JUST REDUCED!!! Centrally located 3BD/3BTH townhome in a gated Kissimmee community just minutes from Disney and Orlando’s top attractions. Smart, flexible layout featuring a first floor bedroom and full bath, plus 2 upstairs bedrooms including a private primary suite. Enjoy a private patio with **no rear neighbors** for added privacy and outdoor relaxation. HOA covers lawn care, exterior maintenance, and roof for added convenience. Community amenities include pool, clubhouse, and playground. Ideal for investors seeking strong rental potential in a high demand location.

Listing is courtesy of: REAL ESTATE EMPIRE GROUP, INC. (305-592-1588)

Listing Agent: Carrie Castro, Pa (786-338-1050)

Remarks: Under contract-accepting backup offers. Welcome to this well-kept 3-bedroom, 3 full-bath townhome located in the gated community of Crestwynd Bay in Kissimmee. This property offers a functional and comfortable layout, featuring vinyl flooring in the main living areas and carpet in the bedrooms, creating a practical and inviting living space. The kitchen is equipped with ample cabinetry, solid surface countertops, and a breakfast bar that opens to the living and dining areas—perfect for everyday living or hosting guests. Natural light flows throughout the home, enhancing the clean and well-maintained condition. A first-floor bedroom and full bath provide flexibility for guests, extended family, or multi-generational living. Upstairs, you’ll find additional spacious bedrooms with plenty of storage. Step outside to a private patio area, ideal for relaxing after a long day or enjoying Florida’s weather. Residents of Crestwynd Bay enjoy resort-style amenities, including a community pool, clubhouse, playground, and green spaces. The HOA includes exterior maintenance, internet, cable, and trash service—offering convenience and low-maintenance ownership. Ideally located just minutes from Walt Disney World, with quick access to US-192, shopping, dining, golf, and major attractions. The property is zoned for short-term and long-term rentals, making it a great option for a primary residence, vacation home, or investment property. Schedule your showing today and explore the potential this property has

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Vanessa Medina Conde (787-645-0626)

Remarks: Under contract-accepting backup offers. Welcome to this fully furnished 3-bedroom, 3-bathroom townhome nestled in the gated community of Crestwynd Bay. This move-in-ready home offers a durable tile roof, a private concrete patio, and the rare bonus of no rear neighbors—just peaceful green conservation views for added privacy and tranquility. Inside, you'll find a spacious layout perfect for personal use or short-term rental. The HOA includes exterior maintenance, basic cable, internet, trash service, and access to community amenities like a pool and playground. Ideally located just minutes from Walmart, Disney World, and major resorts, with quick access to I-4, Osceola Parkway, Highway 192, and the 429 toll road, this home offers both comfort and convenience. Whether you're seeking a primary residence, vacation retreat, or investment property, this townhome delivers value and location in one.

Listing is courtesy of: THE FIRM RE (407-227-3345)

Listing Agent: Naf Zaman (407-580-5483)