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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
  • /75

    $79,999

    • 3 Beds
    • 2 Baths

    1746 Sugar Pine Ave Unit 240, Kissimmee, FL 34758

    This 1,536-square-foot partially furnished 3 bed/ 2 bath home is located in a Kissimmee 55-plus community where the second resident can be as young as 45. The kitchen and dining area feature a spacious open-concept layout with tile and laminate flooring offering a modern and easy-to-maintain living space. The home has been meticulously kept with a roof replaced in November 2017, a one-year-old

    Lisa Dobbs LISA DOBBS LLC

    1746 Sugar Pine Ave Unit 240, Kissimmee, FL 34758
  • /23

    $24,995

    • 3 Beds
    • 2 Baths
    • 672 Sq Ft

    3602 Wonderland Park Ln, Kissimmee, FL 34746

    Welcome to this well-maintained 3-bedroom, 2-bathroom manufactured home located in the desirable Good Samaritan 55 plus community, offering low lot rent and a comfortable lifestyle in the heart of Central Florida. As you enter the home, you are greeted by a spacious utility room featuring a washer and dryer, along with an additional sink perfect for laundry needs or extra cleaning convenience.

    Maria Orozco Four Star Homes, Inc.

    3602 Wonderland Park Ln, Kissimmee, FL 34746
  • /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
  • /67

    $75,000

    • 3 Beds
    • 2 Baths

    1511 Jerstad Way, Kissimmee, FL 34746

    This 3-bedroom, 2-bathroom home in a premier Kissimmee 55-plus community offers both modern comfort and thoughtful accessibility. As you arrive, you will notice the convenience of a covered carport and a dedicated ramp providing easy access to the home. The exterior also features a practical shed, perfect for additional storage or a workshop area. Upon entering, you are greeted by an inviting

    Lisa Dobbs LISA DOBBS LLC

    1511 Jerstad Way, Kissimmee, FL 34746
  • /69

    $69,000

    • 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
  • /94

    $564,900

    • 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 FRONT ENTRY and a stunning WATER view. MOTIVATED SELLER!! 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

    Debra DiCintio BELLA VERDE REALTY LLC

    772 San Raphael St, Kissimmee, FL 34759
  • /28

    $35,000

    • 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
  • /100

    $540,000

    • 3 Beds
    • 3 Baths
    • 3,078 Sq Ft

    352 Hamrick Dr, Kissimmee, FL 34759

    GOLFER’S DREAM HOME! This beautifully designed BOLERO on GOLF COURSE floor plan includes a convenient CASITA, perfect for visiting family, a private office, or a hobby retreat. Offering 3,078 sq. ft. of interior living space and a total of 3,752 square feet this EXCEPTIONAL home is truly ONE OF A KIND! Located CLOSE to the vibrant VILLAGE CENTER offering easy access to all major events, the

    Debra DiCintio BELLA VERDE REALTY LLC

    352 Hamrick Dr, Kissimmee, FL 34759
  • /77

    $59,000

    • 2 Beds
    • 2 Baths

    1743 Conifer Ave Unit 23, Kissimmee, FL 34758

    Enter this 2-bedroom, 2-bathroom home located in a premier Kissimmee 55-plus community, which allows a second resident to be age 45 or older. A large carport provides ample space for two vehicles, leading you into an open dining and kitchen area designed for entertaining with crisp white cabinets and newer appliances. The interior features durable vinyl plank flooring, spacious closets for all

    Lisa Dobbs LISA DOBBS LLC

    1743 Conifer Ave Unit 23, Kissimmee, FL 34758
  • /43

    $499,000

    • 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
  • /66

    $75,000

    • 2 Beds
    • 2 Baths

    1650 Calvin Cir, Kissimmee, FL 34746

    This two-bedroom home in Kissimmee's premier 55-plus community delivers a functional design focused on ease and accessibility. The interior features a spacious pass-through kitchen that opens directly to the dining room overlooking the living room, creating a cohesive flow complemented by durable vinyl plank flooring throughout. The master suite serves as a private retreat with its own walk-in

    Lisa Dobbs LISA DOBBS LLC

    1650 Calvin Cir, Kissimmee, FL 34746
  • /77

    $49,500

    • 2 Beds
    • 2 Baths

    1756 Western Redwood Ave Unit 169, Kissimmee, FL 34758

    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 Daiken AC with transferrable warranty on parts and labor till Dec 2035. Energy-saving double-pane Low-E windows and doors. The

    Lisa Dobbs LISA DOBBS LLC

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

    $38,000

    • 2 Beds
    • 2 Baths

    1735 Balsam Ave, Kissimmee, FL 34758

    Seller Motivated. Reduced ---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

    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

    $29,900

    • 2 Beds
    • 2 Baths

    1739 Red Pine Ave, Kissimmee, FL 34758

    SELLER MOTIVATED---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

    Lisa Dobbs LISA DOBBS LLC

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

    $55,000

    • 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

    $49,900

    • 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 or Unfurnished and

    Lisa Dobbs LISA DOBBS LLC

    1755 Conifer Ave Unit 29, Kissimmee, FL 34758

Home Trends in Kissimmee, FL

Housing Trends

Median Sale Price
$374,715
Median Single Family Sale Price
$394,990
Median Townhouse Sale Price
$359,000
Median 2 Bedroom Sale Price
$209,800
Median 1 Bedroom Sale Price
$145,000
Average Price Per Sq Ft
$212
Number of Homes for Sale
2,999
Last 12 months Home Sales
5,505
Months of Supply
6.50
Median List Price
$394,900
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
1%
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