5,827

Pleasant Hill Homes

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  • /40

    $229,900

    • Land
    • 0.52 Acre
    • $442,115 per Acre

    0 Hidden Harbor Ln, Kissimmee, FL 34746

    LAKEFRONT LOT in GATED NEIGHBORHOOD of HIDDEN HARBOR * 0.52 ACRES * PICK YOUR OWN BUILDER * BUILD ON YOUR TIMELINE * TENNIS COURTS, GAZEBO, BASEBALL DIAMOND and a FISHING PIER OVERLOOKING the NEIGHBORHOOD POND. Last available buildable LAKEFRONT lot in the EXCLUSIVE, GATED Hidden Harbor community, nestled on the stunning shores of Lake Toho, part of the renowned Chain of Lakes. This 0.52-acre

    Racquel Schroeder EAST PARK REALTY LLC

    0 Hidden Harbor Ln, Kissimmee, FL 34746
  • /2

    $489,000 Sold Feb 28, 2025

    • 2,896 Sq Ft
    • $169/SF
    • 13 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 2024

    4250 Nightcaps Way, Kissimmee, FL 34746

    Under Construction. Start out the New Year right with the classic yet modern Durham! This showstopper has five bedrooms and two and a half bathrooms. The designer kitchen features an abundance of counter and cabinet space that is sure to appeal to your inner chef. The family room overlooks the dining room and kitchen, with completely open sight lines. The Durham provides roomy bedrooms with an

    Ben Goldstein LENNAR REALTY

    4250 Nightcaps Way, Kissimmee, FL 34746
    • /18

      Est $394,348 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,853 Sq Ft

      2215 Pocky Way, Kissimmee, FL 34746

      2215 Pocky Way, Kissimmee, FL 34746
  • /79

    $574,999

    • 5 Beds
    • 3 Baths
    • 3,387 Sq Ft

    2629 Maggiore Cir, Kissimmee, FL 34746

    POOL...POOL...POOL...NO BACKYARD NEIGHBORS! This stunning 5-bedroom, 3-bathroom, two-story home is perfectly situated on a quiet cul-de-sac in the highly sought-after gated community of Brighton Estates in Kissimmee. Offering a resort-style lifestyle with a custom-built pool, super low HOA, and an extra-large fenced lot, this home is move-in ready and waiting for its new owner!Step inside

    Dennesha Leachman GLOBAL SAPPHIRE REALTY LLC

    2629 Maggiore Cir, Kissimmee, FL 34746
  • /2

    $384,900 Sold Feb 26, 2025

    • 2,388 Sq Ft
    • $161/SF
    • 97 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2001

    2434 Huron Cir, Kissimmee, FL 34746

    This charming two-story home features four spacious bedrooms and two well-appointed bathrooms, all located upstairs for added privacy. Freshly painted inside and out, it boasts new carpeting in the bedrooms and luxurious vinyl plank flooring throughout the living areas. The kitchen seamlessly opens to the cozy family living space, complete with a welcoming fireplace, making it perfect for

    Robert Jones OFFERPAD BROKERAGE FL, LLC

    2434 Huron Cir, Kissimmee, FL 34746
    • /17

      Est $348,443 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,444 Sq Ft

      4242 Pebbles Throw Dr, Kissimmee, FL 34746

      4242 Pebbles Throw Dr, Kissimmee, FL 34746
  • /73

    $1,050,000

    • 5 Beds
    • 3 Baths
    • 4,557 Sq Ft

    3161 Appaloosa Ct, Kissimmee, FL 34746

    You MUST come see this home for yourself! This home is the textbook definition of a dream home! This is the one-of-a-kind perfect combination of a country home in a city location! With a total of five acres of land, located in a private community with little to no neighbors, enjoy true bliss and serenity of having so much room all to yourself. Entering the gated fence surrounded by a wood fence

    Blanca Armada REMAX PREMIER PROPERTIES

    3161 Appaloosa Ct, Kissimmee, FL 34746
  • /2

    $690,000 Sold Feb 21, 2025

    • 2,834 Sq Ft
    • $243/SF
    • 67 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1986

    2701 Granada Blvd, Kissimmee, FL 34746

    From the moment you begin driving down the long, private driveway, serenity and space are what you will find in this beautiful, expansive, pool home in the highly sought out community of Tohop Estates, with no HOA! As you step inside, you will find updated luxury vinyl flooring, freshly painted rooms, and many rooms with new fans and fixtures. You will recognize quickly, there is plenty of

    Wendy Moore ERA GRIZZARD REAL ESTATE

    2701 Granada Blvd, Kissimmee, FL 34746
    • /17

      Est $337,057 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,267 Sq Ft

      4236 Pebbles Throw Dr, Kissimmee, FL 34746

      4236 Pebbles Throw Dr, Kissimmee, FL 34746
  • /26

    $445,000

    • 5 Beds
    • 2.5 Baths
    • 2,388 Sq Ft

    1902 Presley Place, Kissimmee, FL 34746

    Beautiful home built 2024, This two-story home has five bedrooms, two and a half baths, and a two-car garage. Open concept living space combining the living, dining and kitchen make it the perfect space to entertain and relax. Tile throughout the main living space and wet areas. Kitchen has quartz counter tops and stainless steel appliances with a Modern Insta view refrigerator. Large pantry and

    Alexis McKenzie REAL BROKER, LLC

    1902 Presley Place, Kissimmee, FL 34746
  • /2

    $480,019 Sold Feb 18, 2025

    • 2,109 Sq Ft
    • $228/SF
    • 4 Beds
    • 3 Baths
    • Built 2025

    2365 Pocky Way, Kissimmee, FL 34746

    SOLD DATA ONLY

    Stellar Non-Member Agent Stellar Non-Member Office

    2365 Pocky Way, Kissimmee, FL 34746
    • /16

      Est $338,843 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,267 Sq Ft

      4272 Pebbles Throw Dr, Kissimmee, FL 34746

      4272 Pebbles Throw Dr, Kissimmee, FL 34746
  • /35

    $545,000

    • 5 Beds
    • 4 Baths
    • 3,193 Sq Ft

    2006 Myrtle Pine St, Kissimmee, FL 34746

    This beauty offers TWO homes under one roof. Feature 5 full bedroom, 4 full bath open floor plan. This home is nearly new and comes with a builder transferable home warranty. It is the BAXTER MULTI-GEN SMART floor plan - Features NO Yard Mowing, the lawn care service is covered by the HOA fees. This home also offers a long covered entrance porch, with SEPARATE MULTI-GEN IN-LAW SUITE that offers 1

    Caroline Abreu REIS E SILVA REALTY GROUP LLC

    2006 Myrtle Pine St, Kissimmee, FL 34746
  • /2

    $399,999 Sold Feb 18, 2025

    • 2,370 Sq Ft
    • $169/SF
    • 5 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 2024

    4373 Twisted Twig Bend, Kissimmee, FL 34746

    Under Construction. Look no further we have found your dream home. The Columbia Plan is a two-story home with five bedrooms, two and a half baths, and a two-car garage. This impressive home provides an open floor plan with living room, dining area, and kitchen with island & pantry. The Owner Suite features a large walk-in shower, and spacious walk-in closet. The second floor includes four

    Ben Goldstein LENNAR REALTY

    4373 Twisted Twig Bend, Kissimmee, FL 34746
    • /13

      Est $406,805 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,077 Sq Ft

      4405 Seven Canyons Dr, Kissimmee, FL 34746

      4405 Seven Canyons Dr, Kissimmee, FL 34746
  • /26

    $338,000

    • 4 Beds
    • 2 Baths
    • 1,540 Sq Ft

    4406 Hidden Meadow Dr, Kissimmee, FL 34746

    This cozy single-family home offers a spacious layout with 4 bedrooms and 2 bathrooms. The property boasts a 2-car garage, providing ample vehicle storage or parking space. Inside, you’ll find a dedicated laundry room for convenience and efficiency. The fenced backyard offers both privacy and a safe area. Nestled in a peaceful and quiet community, the property is ideal for those seeking a calm

    Amir Khan AAMIR KHAN

    4406 Hidden Meadow Dr, Kissimmee, FL 34746
  • /2

    $395,000 Sold Feb 18, 2025

    • 1,853 Sq Ft
    • $213/SF
    • 69 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 2024

    2253 Amorie Dr, Kissimmee, FL 34746

    Under Construction. Welcome to the warm and inviting Allentown. This amazing home is complete with 4 bedrooms and 2 bathrooms. The heart of the home has a center island and overlooks the dining and family room, which is great for entertaining. The owner suite features a large private bathroom and a roomy walk-in closet. These single-family homes come with Lennar’s Everything’s Included promise.

    Ben Goldstein LENNAR REALTY

    2253 Amorie Dr, Kissimmee, FL 34746
    • /24

      Est $407,733 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,077 Sq Ft

      4456 Seven Canyons Dr, Kissimmee, FL 34746

      4456 Seven Canyons Dr, Kissimmee, FL 34746
  • /39

    $600,000

    • 6 Beds
    • 4 Baths
    • 2,905 Sq Ft

    2200 Pine Needle Trail Unit 3, Kissimmee, FL 34746

    Multi-Generational Pool Home with Income-Producing Apartment on Over Half an Acre!Discover the perfect blend of space, flexibility, and investment potential with this rare multi-generational home with a separate apartment in a sought-after neighborhood. Nestled on over half an acre, this well-maintained 6-bedroom, 4-bathroom pool home offers versatile living options ideal for extended

    Oliver Thorpe NEXTHOME SOLUTIONS REALTY

    2200 Pine Needle Trail Unit 3, Kissimmee, FL 34746
  • /2

    $260,000 Sold Feb 14, 2025

    • 1,536 Sq Ft
    • $169/SF
    • 50 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2006

    2844 Grasmere View Pkwy, Kissimmee, FL 34746

    Welcome home! This updated townhouse is ready and waiting for your personal touches. The cozy front porch offers a nice pond view and a warm entrance into a well-appointed interior. As you enter, you'll be captivated by the well-designed floor plan that seamlessly blends elegance and functionality boasting luxurious ceramic tile throughout the first floor. The spacious living space and formal

    Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

    2844 Grasmere View Pkwy, Kissimmee, FL 34746
    • /19

      Est $397,084 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,853 Sq Ft

      2221 Pocky Way, Kissimmee, FL 34746

      2221 Pocky Way, Kissimmee, FL 34746
  • /35

    $484,990

    • 4 Beds
    • 3 Baths
    • 2,109 Sq Ft

    4086 Gooseberry Trail, Kissimmee, FL 34746

    One or more photo(s) has been virtually staged. Discover this stunning 4-bedroom, 3-bathroom Next Gen home in the desirable community of Storey Creek, featuring a private Mother-In-Law Suite with a separate entrance, bedroom, bathroom, kitchenette, and living area—ideal for multigenerational living or rental income. Built in 2024, this home boasts a modern, open-concept design, abundant natural

    Yadibelt Lopez Larroque NORTHGROUP REAL ESTATE, INC

    4086 Gooseberry Trail, Kissimmee, FL 34746
  • /2

    $367,000 Sold Feb 14, 2025

    • 1,921 Sq Ft
    • $191/SF
    • 101 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2001

    4308 Biel Ct, Kissimmee, FL 34746

    Welcome home to this beautifully kept and spacious 3 bedroom 2 bath home located in the much sought after Brighton Lakes gated community. Situated on a nice sized fenced lot with no rear neighbors, this home offers a layout that was designed with family and friends to gather in mind, as it features a formal living room, formal dining room, separate family room and a breakfast nook! The kitchen

    Judy Julien KELLER WILLIAMS WINTER PARK

    4308 Biel Ct, Kissimmee, FL 34746
    • /19

      Est $389,742 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,853 Sq Ft

      4217 Little Owl Ln, Kissimmee, FL 34746

      4217 Little Owl Ln, Kissimmee, FL 34746
  • /31

    $999,000

    • 5 Beds
    • 3.5 Baths
    • 3,796 Sq Ft

    3150 Appaloosa Ct, Kissimmee, FL 34746

    Welcome to this stunning home located on a peaceful cul-de-sac in Kissimmee. This beautiful property features a spacious open floor plan with oversized pool, appropriate for entertaining. Private gated entry, sits on over 5 acres of wooded little piece of heaven. Grounds are professionally maintained. Privacy Galore. The modern kitchen boasts stainless steel appliances and ample counter space.

    Steven Koleno BEYCOME OF FLORIDA LLC

    3150 Appaloosa Ct, Kissimmee, FL 34746
  • /2

    $406,990 Sold Feb 13, 2025

    • 1,853 Sq Ft
    • $220/SF
    • 68 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 2024

    4396 Pebbles Throw Dr, Kissimmee, FL 34746

    One or more photo(s) has been virtually staged. Under Construction. Welcome to the warm and inviting Allentown. This amazing home is complete with 4 bedrooms and 2 bathrooms. The heart of the home has a center island and overlooks the dining and family room, which is great for entertaining. The owner suite features a large private bathroom and a roomy walk-in closet. These single-family homes

    Ben Goldstein LENNAR REALTY

    4396 Pebbles Throw Dr, Kissimmee, FL 34746
    • /19

      Est $392,261 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,853 Sq Ft

      2233 Pocky Way, Kissimmee, FL 34746

      2233 Pocky Way, Kissimmee, FL 34746
  • /26

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,542 Sq Ft

    3100 Rocky River Rd, Kissimmee, FL 34746

    Discover the perfect blend of style and comfort in this 3-bedroom, 2-bathroom home in Concorde Estates, Kissimmee! Step inside to a bright and open layout, with a beautifully remodeled kitchen featuring a stylish island and modern backsplash. The spacious primary suite offers a peaceful space, while the private patio is perfect for relaxing or hosting gatherings. Enjoy upscale touches like tray

    Edanny Nava Colina ROMAN'S PRO REALTY LLC

    3100 Rocky River Rd, Kissimmee, FL 34746
  • /2

    $417,153 Sold Feb 07, 2025

    • 2,370 Sq Ft
    • $176/SF
    • 46 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 2024

    4421 Twisted Twig Bend, Kissimmee, FL 34746

    Under Construction. Look no further we have found your dream home. The Columbia Plan is a two-story home with five bedrooms, two and a half baths, and a two-car garage. This impressive home provides an open floor plan with living room, dining area, and kitchen with island & pantry. The Owner Suite features a large walk-in shower, and spacious walk-in closet. The second floor includes four

    Ben Goldstein LENNAR REALTY

    4421 Twisted Twig Bend, Kissimmee, FL 34746
    • /19

      Est $481,185 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 2,896 Sq Ft

      4206 Pebbles Throw Dr, Kissimmee, FL 34746

      4206 Pebbles Throw Dr, Kissimmee, FL 34746
  • /8

    $150,000

    • Land
    • 1.05 Acres
    • $142,857 per Acre

    0 Earle Ct Unit MFRS5122190, Kissimmee, FL 34746

    Discover the perfect opportunity to build your dream home on this stunning property with over 1 acre in an exclusive gated community. Nestled in a peaceful setting, this property offers breathtaking pond views, creating a tranquil backdrop for your future home.Enjoy the privacy and security of a gated entrance while being surrounded by pristine natural beauty and upscale residences.

    Kevin Salvatella ONE TEAM REALTY

    0 Earle Ct Unit MFRS5122190, Kissimmee, FL 34746
  • /2

    $404,000 Sold Feb 07, 2025

    • 2,370 Sq Ft
    • $170/SF
    • 5 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 2024

    4409 Twisted Twig Bend, Kissimmee, FL 34746

    Under Construction. Look no further we have found your dream home. The Columbia Plan is a two-story home with five bedrooms, two and a half baths, and a two-car garage. This impressive home provides an open floor plan with living room, dining area, and kitchen with island & pantry. The Owner Suite features a large walk-in shower, and spacious walk-in closet. The second floor includes four

    Ben Goldstein LENNAR REALTY

    4409 Twisted Twig Bend, Kissimmee, FL 34746
    • /17

      Est $363,048 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,555 Sq Ft

      4207 Pebbles Throw Dr, Kissimmee, FL 34746

      4207 Pebbles Throw Dr, Kissimmee, FL 34746
  • /50

    $359,900

    • 3 Beds
    • 2 Baths
    • 1,558 Sq Ft

    4475 Casablanca Ave, Kissimmee, FL 34746

    Welcome to this exceptional single-family home in the Casa Bella subdivision. This home was built in 2021 and features a spacious living area with plenty of upgrades. The kitchen showcases 36-inch upper cabinets, and you will love the granite countertops and the kitchen island that is perfect for gathering with family. The front of the house includes two secondary bedrooms, a secondary bathroom,

    Chris Creegan CREEGAN GROUP

    4475 Casablanca Ave, Kissimmee, FL 34746
  • /35

    $478,000 Sold Feb 07, 2025

    • 3,273 Sq Ft
    • $146/SF
    • 149 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 2020

    4362 Seven Canyons Dr, Kissimmee, FL 34746

    BACK ON THE MARKET, BUYERS FINANCING FELL THROUGH ***3 CAR GARAGE***POND VIEW***5TH BEDROOM LOCATED ON THE FIRST FLOOR*** NO CDD. Why wait for a new construction. Look at this stunning 5-bedroom, 3-bathroom home with pond view offers plenty of space for your family and friends. 5th bedroom conveniently located on the first floor with a 3rd bathroom right next to it, perfect for the in-laws. The

    Elyse Bisbal EXP REALTY LLC

    4362 Seven Canyons Dr, Kissimmee, FL 34746
    • /16

      Est $350,045 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,555 Sq Ft

      1900 Turtle Dove Ln, Kissimmee, FL 34746

      1900 Turtle Dove Ln, Kissimmee, FL 34746
  • /17

    $1,100,000

    • 3 Beds
    • 2.5 Baths
    • 3,129 Sq Ft

    4261 Twilight Trail, Kissimmee, FL 34746

    Very Unique, Gorgeous Custom-Built Home, situated on 5 acres of land, fenced with NO HOA. NO CDD fees. This amazing property features 3 bedrooms, Den/office/ and 2 1/2 bathrooms, large Master suite, The Master bathroom has a large walk-in shower and Jacuzzi. Huge family room with a brick Fireplace and high ceilings. Charming property has a huge kitchen with stainless steel appliances, granite

    Ralph Carrion LA ROSA REALTY KISSIMMEE

    4261 Twilight Trail, Kissimmee, FL 34746
  • /2

    $472,000 Sold Jan 31, 2025

    • 2,109 Sq Ft
    • $224/SF
    • 13 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2024

    4209 Nightcaps Way, Kissimmee, FL 34746

    Under Construction. Beautiful corner lot!! Caring for aging parents or have a young adult child still at home? This one story, Next Gen home has 4 bedrooms / 3 baths and a two car garage. There is a separate entrance for a Next Gen Bedroom, living room and kitchenette, giving the sense of privacy and independence within proximity. These single-family homes come with Lennar’s Everything’s

    Ben Goldstein LENNAR REALTY

    4209 Nightcaps Way, Kissimmee, FL 34746
    • /35

      Est $468,665 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,714 Sq Ft

      1852 Ancestry Trail, Kissimmee, FL 34746

      1852 Ancestry Trail, Kissimmee, FL 34746
  • /9

    $2,500,000

    • Land
    • 8 Acres
    • $312,110 per Acre

    4445 Austin Rd, Kissimmee, FL 34746

    This exceptional 8+ acre property presents a rare opportunity for investors, builders, or those seeking a private sanctuary. Whether you envision developing a boutique subdivision—ideal for single-family homes, townhomes, or duplexes—or creating your own secluded paradise, this property offers unmatched versatility. Nestled away from traffic yet conveniently surrounded by established and emerging

    Tim Weisheyer DREAM BUILDERS REALTY

    4445 Austin Rd, Kissimmee, FL 34746

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