18

Kissimmee, FL Homes for Sale in 55+ Community

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  • /58

    $49,900

    $59K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,420 Sq Ft

    1744 Sugar Pine Ave Unit 239, Kissimmee, FL 34758

    SELLER MOTIVATED--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 breakfast bar is made of pure oak with a glossy finish.

    Lisa Dobbs LISA DOBBS LLC

    1744 Sugar Pine Ave Unit 239, Kissimmee, FL 34758
  • /12

    $25,000

    • 3 Beds
    • 2 Baths
    • 1,458 Sq Ft

    1742 Conifer Ave, Kissimmee, FL 34758

    Located in a beautiful 55 plus community, this incredible home features 1458 sq ft with a 12' x 14' enclosed lanai and 8' x 12' shed. Three bedrooms provides a master suite, guest room and an office or craft room! It's spacious living area, separate dining area and open kitchen are welcoming and offer more than enough room to relax in comfort. The promotional monthly fee package of $1055 is a

    Todd Newby NEWBY REALTY INC

    1742 Conifer Ave, 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

    $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

    Corali Fuentes Four Star Homes, Inc.

    1717 Conifer Ave, Kissimmee, FL 34758
  • /63

    $55,000

    • 2 Beds
    • 2 Baths
    • 672 Sq Ft

    1543 Parkgate Dr, Kissimmee, FL 34746

    Welcome to a beautifully maintained 2 bed 2 bath move-in-ready oasis located within the highly desirable Oakwood Meadows 55-plus community. From the moment you enter, this unique home challenges every single-wide stereotype, offering an incredibly bright, airy, and spacious footprint designed for comfortable living. You are greeted by a welcoming kitchen and dining area featuring durable,

    Lisa Dobbs LISA DOBBS LLC

    1543 Parkgate Dr, Kissimmee, FL 34746
  • /76

    $60,000

    • 3 Beds
    • 2 Baths

    4691 Blue Spruce Ave Unit 109, Kissimmee, FL 34758

    The moment you enter this beautiful, fully furnished 3-bedroom, 2-bathroom home, you will feel the stress just melt away. Located in a highly desirable, active 55-plus community-where the second resident can be as young as 45 years old-this property is designed with an effortless, open-concept flow. The spacious living area leads directly into a bright kitchen and dinette area that is perfect for

    Lisa Dobbs LISA DOBBS LLC

    4691 Blue Spruce Ave Unit 109, Kissimmee, FL 34758
  • /97

    $559,900

    $30K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,616 Sq Ft

    772 San Raphael St, Kissimmee, FL 34759

    Virtually Staged. NOW IS YOUR OPPORTUNITY TO BECOME THE PROUDLY OWNER OF 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

    Miguel Elvira BELLA VERDE REALTY LLC

    772 San Raphael St, Kissimmee, FL 34759
  • /65

    $485,000

    • 2 Beds
    • 2.5 Baths
    • 1,850 Sq Ft

    394 Monterey St, Kissimmee, FL 34759

    RARE LAKESIDE PARADISE! Experience exceptional active 55 plus community in this move-in-ready lakeside home, where striking curb appeal meets a thoughtfully designed layout. From the moment you enter, the property welcomes you with an immediate sense of warmth and an impressive view of the water. To the left of the foyer, a privately situated second bedroom and full bathroom an ideal layout for

    Lisa Dobbs REAL BROKER, LLC

    394 Monterey St, Kissimmee, FL 34759
  • /28

    $35,000

    $13K PRICE DROP
    • 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
  • /77

    $45,000

    $14K PRICE DROP
    • 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
  • /58

    $30,000

    $13K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,134 Sq Ft

    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, and the peace of mind of a brand-new AC unit installed in July 2026 alongside a roof from 2018. Inside, the dining and living room feature matching chandeliers that create a very

    Lisa Dobbs LISA DOBBS LLC

    1735 Balsam Ave, Kissimmee, FL 34758
  • /24

    $124,900

    $4K PRICE DROP
    • 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
  • /12

    $30,000

    • 2 Beds
    • 2 Baths
    • 1,075 Sq Ft

    1738 Western Redwood Ave, Kissimmee, FL 34758

    This lovely 2br/2ba home, located in a 55 plus community, is spacious and welcoming and just waiting for you to come home! Plank flooring and an open floorplan provides warmth and charm. Bedrooms are large with great closet space and front lanai off your large living room allows a fantastic spot to enjoy your morning coffee. Whispering Pines is an active 55 community nestled in a country setting,

    Todd Newby NEWBY REALTY INC

    1738 Western Redwood Ave, Kissimmee, FL 34758
  • /14

    $39,900

    $15K PRICE DROP
    • 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

    $25,000

    $15K PRICE DROP
    • 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

    $9K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 12,662 Sq Ft

    1727 Red Pine Ave, Kissimmee, FL 34758

    Qualified financed buyers may receive a closing credit equal to their first three mortgage payments, subject to lender approval. Cash buyers may receive an equivalent credit or price incentive with an acceptable offer. MOVE-IN-READY 2016 HOME IN WHISPERING PINES Beautifully maintained 2016 mobile home featuring 2 bedrooms, 2 bathrooms, and approximately 1,248 square feet of bright, open living

    Mylvia Nova Four Star Homes, Inc.

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

    $40,000

    $24K PRICE DROP
    • 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 Price Trends

Median Sale Price
$368,000
Median Single Family Sale Price
$385,823
Median Townhouse Sale Price
$349,000
Median 2 Bedroom Sale Price
$258,790
Median 1 Bedroom Sale Price
$135,000
Average Price Per Sq Ft
$209
Number of Homes for Sale
3,032
Last 12 months Home Sales
5,669
Months of Supply
6.40
Median List Price
$388,500
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-1%
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