186 WINDWARD DRIVE, OSPREY, Sarasota, FL, 34229, Residential, 3, 2, 05cd504e820868427fc9af6a8d6d6088, N6142087,186,WINDWARD
- $649,500
186 WINDWARD DRIVE, OSPREY, Sarasota, FL, 34229, Residential, 3, 2, 05cd504e820868427fc9af6a8d6d6088, N6142087,186,WINDWARD
- $649,500
Overview
- Single Family Residence
- 3
- 2
- 2
- 2505 Square Feet
- 1983
Description
Price was reduced over $100,000!!! Went pending immediately and then the buyers couldn’t secure financing. It is now BACK ON MARKET as of 3/19 and NO INSPECTIONS HAVE BEEN DONE! Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2-bath residence offers a split bedroom layout, unique community amenities, NEW ROOF in 2022, and plenty of room for a private pool. As you enter the home, you will be greeted by the formal living room and dining room to the left and hallway to the family room, kitchen, and dinette straight ahead. The entire interior has been professionally painted in 2025, and there is tons of natural light that flows through the many windows of this home. The kitchen is open to the family room and dinette for easy entertaining. There is also a HUGE bonus room toward the back of the home. Next to the family room is entrance to the hallway leading to the two guest bedrooms and guest bathroom. On the opposite side of the home, past the dining room is the spacious primary suite with generous walk-in closet and ensuite bath. The laundry room is located near the family room. Entrance to the attached 2 car garage is near the foyer. Roof was replaced in 2022 & AC was installed in 2016. The entire house has also been replumbed! Southbay Yacht & Racquet Club is an active lifestyle community with many social, boating, and sports activities. The clubhouse has recently been renovated and features a community pool, fitness center, ballroom, two kitchens, card room, game room, and an elevator! Additional amenities include 3 tennis courts, 4 pickle ball courts, basketball, playground, bocce, shuffleboard, and miles of walking trails and green space. The community-owned marina—with residents-only boat slips—provides direct Intracoastal Waterway access with no fixed bridges to the Gulf. The community is welcoming and lively—perfect for families and those who enjoy an active, coastal lifestyle. This community is in the perfect location with several warm gulf beaches, Downtown Venice & Downtown Sarasota close by. The famous Casey Key Fish House and Tiki Bar are just a golf cart ride away! Oscar Scherer State Park is across Tamiami Trail and Pine View (#1 school in the state) is about 5 minutes away. This home is ready for you to start living the elevated Southbay lifestyle! **The street behind this house (Blackburn Point Rd.) is a fairly quiet two lane Rd. That’s the road you can take your golf cart to Casey Key Fish House & Tiki Bar!**There is marina space available and fees range between $169-$705 per quarter.**
Address
Open on Google Maps-
Address: WINDWARD
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State/county: Sarasota
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Zip/Postal Code: 34229
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Area: SOUTHBAY YACHT & RACQUET CLUB
Details
Updated on April 23, 2026 at 10:06 am-
Property ID N6142087
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Price $649,500
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Property Size 2505 Square Feet
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Land Area 0.3 Square Feet
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Bedrooms 3
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Bathrooms 2
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Garages 2
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Year Built 1983
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Property Type Single Family Residence
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Property Status Residential
Additional details
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AssociationAmenities Basketball Court, Clubhouse, Fitness Center, Park, Pickleball Court(s), Playground, Pool, Tennis Court(s)
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AssociationFee 613
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AssociationFeeFrequency Quarterly
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AssociationFeeIncludes Common Area Taxes, Community Pool, Escrow Reserves Fund, Fidelity Bond, Manager, Pool Maintenance
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BathroomsFull 2
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BathroomsHalf 0
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BathroomsTotalDecimal 2
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BridgeModificationTimestamp April 22, 2026 at 03:58pm
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BuildingAreaTotal 3298
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CommunityFeatures Boat Slip, Dock, Intracoastal Waterway, Marina, Clubhouse, Deed Restrictions, Fitness Center, Golf Carts OK, Park, Playground, Pool, Sidewalks, Tennis Court(s)
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ConstructionMaterials Block, Stucco
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ContractStatusChangeDate 2026-01-08
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Cooling Central Air
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CoveredSpaces 2
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CumulativeDaysOnMarket 98
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DaysOnMarket 98
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DirectionFaces South
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Directions From the intersection at US 41 and Laurel Rd take US 41 north. Turn left on Southbay Dr. Turn right on Windward Dr. Property will be on your left. From the intersection at US 41 and Blackburn Point Rd take Blackburn Point Rd west. Turn left on Southbay Dr. Turn left on Windward Dr. Property will be on your left.
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ElementarySchool Laurel Nokomis Elementary
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FeedTypes IDX
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Flooring Hardwood
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FoundationDetails Slab
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Furnished Unfurnished
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Heating Central
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HighSchool Venice Senior High
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IDXParticipationYN 1
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InternetAddressDisplayYN 1
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InternetEntireListingDisplayYN 1
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LaundryFeatures Inside, Laundry Room
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LeaseConsideredYN 1
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Levels One
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ListAOR Sarasota - Manatee
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ListAgentAOR Venice
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ListAgentEmail brittanycoleman208@gmail.com
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ListAgentFullName Brittany Coleman, PLLC
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ListAgentKey ab8d9f0202d202679c37cbec33faabd4
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ListAgentMlsId 281525387
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ListAgentPreferredPhone 941-539-5023
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ListOfficeKey e2a72109a8c52d236f668643fc351cf2
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ListOfficeMlsId 281521326
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ListOfficeName KELLER WILLIAMS ON THE WATER S
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ListOfficePhone 941-803-7522
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ListingContractDate 2026-01-06
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ListingKey 05cd504e820868427fc9af6a8d6d6088
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ListingKeyNumeric 777945441
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ListingTerms Cash, Conventional, FHA, VA Loan
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LivingAreaSource Public Records
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LotFeatures Corner Lot, Landscaped
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LotSizeArea 13130
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LotSizeSquareFeet 13130
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MLSAreaMajor 34229 - Osprey
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MiddleOrJuniorSchool Sarasota Middle
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MlsStatus Active
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ModificationTimestamp April 22, 2026 at 03:54pm
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OnMarketDate 2026-01-08
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OriginalEntryTimestamp January 9, 2026 at 12:46am
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OriginalListPrice 749900
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OriginatingSystemKey stellar
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OriginatingSystemName Stellar MLS
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Ownership Fee Simple
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ParcelNumber 0157070011
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ParkingFeatures Deeded, Driveway, Garage Door Opener, Off Street
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PatioAndPorchFeatures Covered, Patio, Screened
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PetsAllowed Yes
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PhotosChangeTimestamp January 9, 2026 at 12:51am
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PhotosCount 93
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PostalCodePlus4 9751
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PriceChangeTimestamp March 6, 2026 at 09:05pm
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RoadFrontageType Street Paved
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RoadSurfaceType Paved, Asphalt
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Roof Tile
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RoomsTotal 11
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STELLAR_ActiveOpenHouseCount 0
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STELLAR_AdditionalLeaseRestrictions Please see HOA docs for more information
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STELLAR_AdditionalRooms Bonus Room, Family Room
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STELLAR_AlternateKeyFolioNum 0157070011
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STELLAR_ApprovalProcess Please see HOA docs for more information
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STELLAR_AssociationEmail judybrown@sbyrc.net
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STELLAR_AssociationFeeRequirement Required
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STELLAR_BOMDate March 19, 2026 at 04:00am
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STELLAR_CalculatedListPriceByCalculatedSqFt 259.28
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STELLAR_CensusBlock 2
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STELLAR_CensusTract 002102
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STELLAR_CurrentPrice 649500
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STELLAR_DPRURL https://www.workforce-resource.com/dpr/listing/MFRMLS/N6142087?w=Agent&skip_sso=true
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STELLAR_DPRURL2 https://www.workforce-resource.com/dpr/listing/MFRMLS/N6142087?w=Customer
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STELLAR_DPRYN 1
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STELLAR_FloodZoneCode X
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STELLAR_GarageDimensions 21x22
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STELLAR_GreenVerificationCount 0
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STELLAR_LeaseRestrictionsYN 1
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STELLAR_ListOfficeContactPreferred 941-803-7522
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STELLAR_ListOfficeHeadOfficeKeyNumeric 1044707
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STELLAR_ListSource MATRIX
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STELLAR_ListSourceOriginal MATRIX
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STELLAR_MinimumLease 3 Months
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STELLAR_MlsMajorChangeType Back On Market
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STELLAR_MonthlyHOAAmount 204.33
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STELLAR_NumOfOwnYearsPriorToLse 2
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STELLAR_NumTimesperYear 2
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STELLAR_OfficeIDXOfficeParticipationYN 1
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STELLAR_OfficeSyndicateTo Apartments.com, International MLS, Realtor.com, Zillow Rental, SkySlope Offers
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STELLAR_OpenHouseCount 3
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STELLAR_PreviousStatus Pending
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STELLAR_RATIO_CurrentPrice_By_BuildingAreaTotal 196.94
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STELLAR_RATIO_CurrentPrice_By_CalculatedSqFt 259.28
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STELLAR_SWSubdivCommunityName Southbay Yacht & Racquet Club
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STELLAR_ShowingRequirements Appointment Only, Combination Lockbox, Go Direct, See Remarks, ShowingTime
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STELLAR_ThirdPartyYN 1
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STELLAR_TotalAcreage 1/4 to less than 1/2
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STELLAR_TotalAnnualFees 2452
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STELLAR_TotalMonthlyFees 204.33
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STELLAR_WaterAccess Intracoastal Waterway, Marina
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STELLAR_WaterAccessYN 1
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STELLAR_WaterfrontFeetTotal 0
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STELLAR_YrsOfOwnerPriorToLeasingReqYN 1
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Sewer Public Sewer
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SourceSystemKey 777945441
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SpecialListingConditions None
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StateOrProvince FL
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StatusChangeTimestamp March 19, 2026 at 03:54pm
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StoriesTotal 1
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StreetName WINDWARD
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StreetNumber 186
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StreetNumberNumeric 186
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StreetSuffix DRIVE
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TaxAnnualAmount 7566.37
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TaxBookNumber 22-27
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TaxLegalDescription LOT 136 SOUTHBAY YACHT & RACQUET CLUB
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TaxLot 136
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TaxYear 2025
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Utilities BB/HS Internet Available, Cable Available, Cable Connected, Electricity Available, Electricity Connected, Sewer Available, Sewer Connected, Water Available, Water Connected
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View Garden
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WaterSource Public
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Zoning RSF2
Features
- Cathedral Ceiling(s)
- Ceiling Fan(s)
- Dishwasher
- Dryer
- Electric Water Heater
- Garage Attached
- Has a View
- Has Cooling System
- Has Garage
- Has Heating System
- High Ceilings
- Home Owners Association
- Irrigation System
- Kitchen/Family Room Combo
- Lighting
- Living Room/Dining Room Combo
- Microwave
- Open Parking
- Primary Bedroom Main Floor
- Private Mailbox
- Rain Gutters
- Range
- Refrigerator
- Sliding Doors
- Split Bedroom
- Thermostat
- Vaulted Ceiling(s)
- Walk-In Closet(s)
- Washer
Mortgage Calculator
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Down Payment
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Loan Amount
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Monthly Mortgage Payment
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Property Tax
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Monthly HOA Fees




























































































