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Kissimmee, FL Homes for Sale in 55+ Community

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  • /58

    $69,900

    • 2 Beds
    • 2 Baths
    • 1,420 Sq Ft

    1744 Sugar Pine Ave Unit 239, Kissimmee, FL 34758

    SELLER MOTIVATED--LIMITED TIME OFFER: Enjoy 1 MONTH FREE Lot Rent---This fully renovated 2 bed/ 2 bath home is situated in the sought-after 55 Plus--Whispering Pines community of Kissimmee. The interior features modern vinyl plank flooring, updated bathrooms including high rise toilets and new shower, a stylish kitchen equipped with stainless steel appliances and granite countertops. The

    Lisa Dobbs LISA DOBBS LLC

    1744 Sugar Pine Ave Unit 239, Kissimmee, FL 34758
  • /44

    $15,000

    • 2 Beds
    • 2 Baths

    1730 Balsam Ave, Kissimmee, FL 34758

    This home offers a wonderful opportunity to join a vibrant 55-plus community where a second resident can be 45 years or older. Priced at only $15,000, this residence features a front porch, a lanai, a convenient shed, and includes a washer and dryer, providing a great foundation for you to make it your own with a little TLC. The monthly lot rent of $1,226.14 covers water, sewer, trash, and access

    Lisa Dobbs LISA DOBBS LLC

    1730 Balsam Ave, Kissimmee, FL 34758
  • /23

    $50,000

    • 2 Beds
    • 2 Baths
    • 936 Sq Ft

    1717 Conifer Ave, Kissimmee, FL 34758

    Welcome to 1717 Conifer Ave, a move-in-ready home offering comfort, style, and peace of mind with many recent upgrades. This spacious 2-bedroom, 2-bath residence is located in a friendly 55 plus community, perfect for enjoying Floridas sunshine and relaxed lifestyle. The home features new PVC plumbing, new appliances, and a dual-fuel generator (gasoline and propane) for added convenience. The

    Maria Orozco Four Star Homes, Inc.

    1717 Conifer Ave, Kissimmee, FL 34758
  • /69

    $79,000

    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft

    1640 Calvin Cir, Kissimmee, FL 34746

    Welcome to this 55-plus community and this 2-bedroom, 2-bathroom home located on a large corner lot. The exterior features well-maintained landscaping with New mulch and plants. This home has been extensively updated with a New Roof, New Air Conditioning, New Piping throughout, New Vinyl Plank Flooring, and Freshly Painted Walls. It comes completely furnished and includes a large living room, a

    Lisa Dobbs LISA DOBBS LLC

    1640 Calvin Cir, Kissimmee, FL 34746
  • /77

    $58,000

    • 2 Beds
    • 2 Baths
    • 1,248 Sq Ft

    1756 Western Redwood Ave Unit 169, Kissimmee, FL 34758

    REDUCED--Experience the perfect Florida lifestyle in this premier 55-plus community in Kissimmee, where the second resident can be as young as 45. This gorgeous two-bedroom, two-bathroom home offers the ultimate peace of mind with a brand-new 2025 roof, a high-efficiency 2024 AC, and energy-saving double-pane Low-E windows and doors. The exterior provides instant curb appeal with professional

    Lisa Dobbs LISA DOBBS LLC

    1756 Western Redwood Ave Unit 169, Kissimmee, FL 34758
  • /94

    $584,900

    • 3 Beds
    • 3.5 Baths
    • 2,616 Sq Ft

    772 San Raphael St, Kissimmee, FL 34759

    PRICE ADJUSTMENT on this impressive VENETIAN model home with Glass Double Door entry and a stunning WATERFRONT view. 3 Bedrooms, each with their own full bath, plus a Powder Bath, Gourmet Kitchen, Dining Room, Breakfast Room and a Den. Open plan with 8' Doors and Windows plus 12' Ceilings. The Kitchen is open to the Great Room and Breakfast Room. Upgrades in the Kitchen include a Center Island,

    Debra DiCintio BELLA VERDE REALTY LLC

    772 San Raphael St, Kissimmee, FL 34759
  • /44

    $299,999

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft

    188 Olympus Way, Kissimmee, FL 34759

    Welcome to this stunning home in a vibrant 55-plus resort-style community! On a prime corner lot, this beautifully built 2022 home boasts modern and clean finishes throughout. Natural light pours in through large windows, creating a bright and airy atmosphere. The spacious kitchen features an oversized island and stainless-steel appliances, ideal for preparing meals and entertaining. With a

    Kasey Borders PREMIER SOTHEBYS INT'L REALTY

    188 Olympus Way, Kissimmee, FL 34759
  • /28

    $43,000

    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft

    1738 Sugar Pine Ave, Kissimmee, FL 34758

    Step into sunny serenity with this charming 2 bedroom, 2 bath home nestled in the vibrant 55 plus community of Whispering Pines in Kissimmee. Just 15 minutes from Disney, and moments from shopping, This partially furnished 1999 gem offers spacious bedrooms, an open layout, and tons of natural light streaming through every room. Enjoy coffee on your screened in porch, take a stroll through lush,

    Mylvia Nova Four Star Homes, Inc.

    1738 Sugar Pine Ave, Kissimmee, FL 34758
  • /83

    $89,000

    • 3 Beds
    • 2 Baths

    1748 Sugar Pine Ave, Kissimmee, FL 34758

    This home is located in a 55 plus community where the second occupant can be 45 years of age. This 3-bedroom, 2-bathroom residence is centered in central Kissimmee, offering a quiet resort setting while remaining close to restaurants, theme parks, and entertainment. As you enter the home, you will find 1,460 square feet of living area and a unique floor plan featuring a master bathroom with

    Lisa Dobbs LISA DOBBS LLC

    1748 Sugar Pine Ave, Kissimmee, FL 34758
  • /43

    $525,000

    • 3 Beds
    • 2.5 Baths
    • 2,470 Sq Ft

    7916 Hanson Bay Place, Kissimmee, FL 34747

    Welcome to this beautifully upgraded Dominica model home located in the highly sought after 55 plus community Four Seasons at Orlando. Offering 3 bedrooms, 2.5 bathrooms, a spacious bonus room, a dedicated storage room, and a 2 car garage, this thoughtfully designed residence blends comfort, functionality, and refined style.Over $60,000 in builder upgrades enhance nearly every space. The

    Andre Kressler KRESSLER REAL ESTATE

    7916 Hanson Bay Place, Kissimmee, FL 34747
  • /36

    $609,000

    • 3 Beds
    • 2.5 Baths
    • 2,360 Sq Ft

    7789 Four Seasons Blvd, Kissimmee, FL 34747

    Welcome to refined Florida living in the sought after Four Seasons Orlando 55 plus community. This beautifully upgraded single family home offers 2,360 square feet of thoughtfully designed space, combining comfort, function, and lifestyle in one of Central Florida’s most desirable active adult neighborhoods. The sought-after Dominica model showcases a thoughtfully designed floor plan features 2

    Andre Kressler KRESSLER REAL ESTATE

    7789 Four Seasons Blvd, Kissimmee, FL 34747
  • /63

    $43,000

    • 2 Beds
    • 2 Baths

    1735 Balsam Ave, Kissimmee, FL 34758

    This home in Kissimmee offers a wonderful opportunity to join a vibrant 55-plus community where a second resident can be 45 years or older. This residence features both a side lanai and a back lanai, a convenient shed. The property is well-maintained with a roof from 2018 and an AC system from 2013. Inside, the dining and living room feature matching chandeliers that create a very elegant look,

    Lisa Dobbs LISA DOBBS LLC

    1735 Balsam Ave, Kissimmee, FL 34758
  • /24

    $124,900

    • 3 Beds
    • 2 Baths
    • 1,580 Sq Ft

    1605 Straight St, Kissimmee, FL 34746

    One of the Finest homes in the NON-PROFIT GOOD SAMARITAN SOCIETY 55 PLUS COMMUNITY. LOW LOT RENT is KEY to ownership in this park with so many amenities to list from Golf and indoor swimming pool to all your health needs! This 3 bedroom and 2 bath home is high up on a wooded lot with flowers abound. The quality of this newer home shows pride in ownership. All upgrades from Walnut cabinets to

    Joanne Gauthier Four Star Homes, Inc.

    1605 Straight St, Kissimmee, FL 34746
  • /14

    $45,000

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft

    4681 Blue Spruce Ave Unit 104, Kissimmee, FL 34758

    This newer home in Whispering Pines 55 plus community is a must see. This home has 2 large bedrooms and 2 baths. This home has a great front porch as well as a side screened in porch to enjoy cool breeze in the evenings. Vinyl plank flooring throughout living area. This community has all the amenities, and a large dog park with a washing station. Come sit under a tiki hut and enjoy the beautiful

    Joanne Gauthier Four Star Homes, Inc.

    4681 Blue Spruce Ave Unit 104, Kissimmee, FL 34758
  • /60

    $39,900

    • 2 Beds
    • 2 Baths

    1739 Red Pine Ave, Kissimmee, FL 34758

    This home in Kissimmee provides an excellent opportunity to reside in an active 55-plus community where a second resident may be 45 years or older. The exterior includes a front lanai and a helpful storage shed, with a ramp installed in 2009 for convenient access. Inside, you will find washer and dryer hookups along with an open floor plan featuring brand-new carpet and vinyl plank flooring. The

    Lisa Dobbs LISA DOBBS LLC

    1739 Red Pine Ave, Kissimmee, FL 34758
  • /37

    $64,000

    • 2 Beds
    • 2 Baths
    • 12,662 Sq Ft

    1727 Red Pine Ave, Kissimmee, FL 34758

    Beautifully maintained 2016 mobile home offering 2 bedrooms, 2 bathrooms, and approximately 1,248 square feet of comfortable, open living space. Located in the desirable 55 PLUS community of Whispering Pines in Kissimmee on leased land, this home provides relaxed Florida living in a well-established setting. The open-concept layout creates a bright and welcoming atmosphere, ideal for both

    Mylvia Nova Four Star Homes, Inc.

    1727 Red Pine Ave, Kissimmee, FL 34758
  • /76

    $59,900

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft

    1755 Conifer Ave Unit 29, Kissimmee, FL 34758

    Imagine a life where your hardest decision is whether to spend the afternoon under a Tiki Hut or on the pickleball court. This isn't just a home; it is an invitation to a permanent vacation in a premier 55-plus community that welcomes a second resident as young as 45. While many homes require a long list of "to-do" projects, this residence is completely furnished and offers total peace

    Lisa Dobbs LISA DOBBS LLC

    1755 Conifer Ave Unit 29, Kissimmee, FL 34758

Home Trends in Kissimmee, FL

Housing Trends

Median Sale Price
$374,999
Median Single Family Sale Price
$394,990
Median Townhouse Sale Price
$360,000
Median 2 Bedroom Sale Price
$210,000
Median 1 Bedroom Sale Price
$145,000
Average Price Per Sq Ft
$213
Number of Homes for Sale
2,971
Last 12 months Home Sales
5,486
Months of Supply
6.50
Median List Price
$395,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
1%
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