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    1. Subdivision Like Rolling Oaks
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    8153 Surf Street
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    Details for 8153 Surf Street, KISSIMMEE, FL 34747
    Single Family
    1. Price: $1,499,000.00
    2. Price sqft: $273.04 / sqft
    3. Previous Price: $1,750,000
    4. Last Price Change: 11/18/25
    5. Days On Market: 467
    6. Bedrooms: 8
    7. Baths: 9
    8. Bldg sqft: 5490
    9. Acreage: 0.08 acres
    10. Pool: Yes
    11. Spa/HotTub: Yes
    12. Waterfront: No
    13. Year Built: 2020
    MLS#: O6273572
    1. County: OSCEOLA
    2. City: KISSIMMEE
    3. Zipcode: 34747
    4. Subdivision: Rolling Oaks Ph 6a
    5. Provided by: LOKATION
    6. mfrmls
    7. DMCA Notice
    WOW! Fun In Paradise Awaits You in this Spectacular Spacious Cottage w/Private Pool & Spa at Margaritaville Resort Orlando! This model features 8 bedrooms all with their own private ensuite bath. The
    Listing Details and 78 Additional Pictures
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    3056 Parrot Head Place
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    Details for 3056 Parrot Head Place, KISSIMMEE, FL 34747
    Single Family
    1. Price: $1,450,000.00
    2. Price sqft: $300.15 / sqft
    3. Previous Price: $1,525,000
    4. Last Price Change: 02/08/26
    5. Days On Market: 505
    6. Bedrooms: 8
    7. Baths: 9
    8. Bldg sqft: 4831
    9. Acreage: 0.08 acres
    10. Pool: Yes
    11. Spa/HotTub: Yes
    12. Waterfront: Yes
    13. Wateraccess: Yes
    14. Waterfront Type: Pond
    15. Year Built: 2018
    MLS#: O6265271
    1. County: OSCEOLA
    2. City: KISSIMMEE
    3. Zipcode: 34747
    4. Subdivision: Rolling Oaks Ph 5
    5. Provided by: EXP REALTY LLC
    6. mfrmls
    7. DMCA Notice
    'easy breezy' cottage on margaritaville resort orlando's 'trophy row'! Extremely rare opportunity to own one of the largest waterfront cottages with pool and spa plus your very own elevator ($40k upgr
    Listing Details and 98 Additional Pictures
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    3052 Parrot Head Place
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    Details for 3052 Parrot Head Place, KISSIMMEE, FL 34747
    Single Family
    1. Price: $1,399,000.00
    2. Price sqft: $289.59 / sqft
    3. Previous Price: $1,425,000
    4. Last Price Change: 03/18/26
    5. Days On Market: 86
    6. Bedrooms: 8
    7. Baths: 9
    8. Bldg sqft: 4831
    9. Acreage: 0.08 acres
    10. Pool: Yes
    11. Waterfront: No
    12. Year Built: 2019
    MLS#: S5143539
    1. County: OSCEOLA
    2. City: KISSIMMEE
    3. Zipcode: 34747
    4. Subdivision: Rolling Oaks Ph 5
    5. Provided by: FLORIDA IN MOTION REALTY INC
    6. mfrmls
    7. DMCA Notice
    Kick back and embrace the laid back island rhythm at this breezy lakefront retreat in Margaritaville Resort Orlando, perfectly positioned on Parrot Head Place. Wrapped in carefree Key West charm, this
    Listing Details and 52 Additional Pictures
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    8145 Surf Street
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    Details for 8145 Surf Street, KISSIMMEE, FL 34747
    Single Family
    1. Price: $1,399,000.00
    2. Price sqft: $332.07 / sqft
    3. Days On Market: 172
    4. Bedrooms: 6
    5. Baths: 6
    6. Bldg sqft: 4213
    7. Acreage: 0.08 acres
    8. Pool: Yes
    9. Spa/HotTub: Yes
    10. Waterfront: No
    11. Year Built: 2020
    MLS#: O6361261
    1. County: OSCEOLA
    2. City: KISSIMMEE
    3. Zipcode: 34747
    4. Subdivision: Rolling Oaks Ph 6a
    5. Provided by: COLDWELL BANKER REALTY
    6. mfrmls
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    Incredible 6 Bedroom WATER FRONT cottage with private pool and spa located in the heart of Margaritaville Resort just 5 minutes from Disney! This immaculately kept, highly sought after floorplan, sits
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    8017 Surf Street
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    Details for 8017 Surf Street, KISSIMMEE, FL 34747
    Single Family
    1. Price: $1,325,000.00
    2. Price sqft: $274.38 / sqft
    3. Previous Price: $1,350,000
    4. Last Price Change: 04/23/26
    5. Days On Market: 68
    6. Bedrooms: 7
    7. Baths: 9
    8. Bldg sqft: 4829
    9. Acreage: 0.08 acres
    10. Pool: Yes
    11. Spa/HotTub: Yes
    12. Waterfront: No
    13. Year Built: 2019
    MLS#: O6386683
    1. County: OSCEOLA
    2. City: KISSIMMEE
    3. Zipcode: 34747
    4. Subdivision: Rolling Oaks Ph 5
    5. Provided by: LUXE PROPERTIES LLC
    6. mfrmls
    7. DMCA Notice
    **7 Bedrooms | 8.5 Bathrooms | Waterfront Living at Its Finest** ENJOY DISNEY MAGIC KINGDOM AND EPCOT FIREWORKS FROM THE TOP DECK. Welcome to your dream home on the lake! This stunning 7 bedroom,
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    21679 106th Lane Road
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    Details for 21679 106th Lane Road, DUNNELLON, FL 34431
    Single Family
    1. Price: $1,247,000.00
    2. Price sqft: $466.34 / sqft
    3. Previous Price: $1,280,000
    4. Last Price Change: 01/07/26
    5. Days On Market: 267
    6. Bedrooms: 3
    7. Baths: 3
    8. Garage / Parking Spaces: 3
    9. Bldg sqft: 2674
    10. Acreage: 10.00 acres
    11. Pool: No
    12. Waterfront: No
    13. Year Built: 2023
    MLS#: OM707484
    1. County: MARION
    2. City: DUNNELLON
    3. Zipcode: 34431
    4. Subdivision: Rolling Oaks Estate
    5. Elementary School: Dunnellon
    6. Middle School: Dunnellon
    7. High School: Dunnellon
    8. Provided by: ENGEL & VOLKERS OCALA
    9. mfrmls
    10. DMCA Notice
    Wind down the gated entrance lined with stately columns and arrive at a property where comfort, charm, and thoughtful details await in this gorgeous 3 bedroom 2 1/2 baths. Surrounded by the natural vi
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    8098 Knee Deep Road
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    Details for 8098 Knee Deep Road, KISSIMMEE, FL 34747
    Single Family
    1. Price: $799,000.00
    2. Price sqft: $432.36 / sqft
    3. Days On Market: 175
    4. Bedrooms: 5
    5. Baths: 6
    6. Bldg sqft: 1848
    7. Acreage: 0.03 acres
    8. Pool: Yes
    9. Spa/HotTub: Yes
    10. Waterfront: No
    11. Year Built: 2020
    MLS#: O6360849
    1. County: OSCEOLA
    2. City: KISSIMMEE
    3. Zipcode: 34747
    4. Subdivision: Rolling Oaks Ph 6b
    5. Elementary School: Westside Elem
    6. Middle School: Kissimmee
    7. High School: Celebration
    8. Provided by: LIFESTYLE INTERNATIONAL REALTY
    9. mfrmls
    10. DMCA Notice
    Experience resort style living in this stunning 5 bedroom, 5.5 bath cottage located in the highly sought after Margaritaville Resort Orlando. Perfectly positioned on an oversized corner lot, this home
    Listing Details and 39 Additional Pictures
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    8031 Knee Deep Road
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    Details for 8031 Knee Deep Road, KISSIMMEE, FL 34747
    Single Family
    1. Price: $795,000.00
    2. Price sqft: $334.88 / sqft
    3. Days On Market: 46
    4. Bedrooms: 4
    5. Baths: 5
    6. Bldg sqft: 2374
    7. Acreage: 0.07 acres
    8. Pool: Yes
    9. Spa/HotTub: Yes
    10. Waterfront: No
    11. Year Built: 2021
    MLS#: O6392792
    1. County: OSCEOLA
    2. City: KISSIMMEE
    3. Zipcode: 34747
    4. Subdivision: Rolling Oaks Ph 6b
    5. Provided by: EXP REALTY LLC
    6. mfrmls
    7. DMCA Notice
    Stunning fully furnished 4 bedroom, 4. 5 bath cottage with private heated pool & spa at margaritaville resort orlando! This exceptional home offers front balconies on both the second and third floors.
    Listing Details and 61 Additional Pictures
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    8014 Knee Deep Road
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    Details for 8014 Knee Deep Road, KISSIMMEE, FL 34747
    Single Family
    1. Price: $774,900.00
    2. Price sqft: $374.35 / sqft
    3. Days On Market: 42
    4. Bedrooms: 4
    5. Baths: 4
    6. Bldg sqft: 2070
    7. Acreage: 0.07 acres
    8. Pool: Yes
    9. Spa/HotTub: Yes
    10. Waterfront: No
    11. Year Built: 2020
    MLS#: O6393521
    1. County: OSCEOLA
    2. City: KISSIMMEE
    3. Zipcode: 34747
    4. Subdivision: Rolling Oaks Ph 6b
    5. Provided by: EXP REALTY LLC
    6. mfrmls
    7. DMCA Notice
    Stunning fully furnished cottage for sale at margaritaville resort orlando with private heated pool and spa!. This cottage has 4 bedrooms, 4 full baths, upgraded "wood" tile flooring, stainless steel
    Listing Details and 78 Additional Pictures
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    8082 Knee Deep Road
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    Details for 8082 Knee Deep Road, KISSIMMEE, FL 34747
    Single Family
    1. Price: $724,900.00
    2. Price sqft: $350.53 / sqft
    3. Previous Price: $759,000
    4. Last Price Change: 01/28/26
    5. Days On Market: 185
    6. Bedrooms: 5
    7. Baths: 6
    8. Bldg sqft: 2068
    9. Acreage: 0.05 acres
    10. Pool: Yes
    11. Waterfront: No
    12. Year Built: 2020
    MLS#: O6357744
    1. County: OSCEOLA
    2. City: KISSIMMEE
    3. Zipcode: 34747
    4. Subdivision: Rolling Oaks Ph 6b
    5. Provided by: COLDWELL BANKER REALTY
    6. mfrmls
    7. DMCA Notice
    Beautiful 5 bedrooms, 5 and a half bathroom POOL COTTAGE ON AN OVERSIZED CORNER LOT located in Margaritaville Resort! Just moments from Disney World, this turn key cottage comes fully furnished with M
    Listing Details and 29 Additional Pictures
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    Equal Housing Opportunity
    Listings provided courtesy of The Hernando County Association of Realtors MLS.
    Listing Data ©2026 REALTOR® Association of Citrus County
    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
    Display of MLS data is usually deemed reliable but is NOT guaranteed accurate.
    Datafeed Last updated on May 9, 2026 @ 12:00 am
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