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1008 N PENNSYLVANIA Avenue
WINTER PARK FL 32789 US

$2,500,000

Active Listing ID O6457191
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4 bed
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3,530 square feet
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5.00 Bath (4 Full , 1 Half)
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Lot: 0.21 Acres
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Single Family Residence

$2,500,000

Active Listing ID O6457191
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1008 N PENNSYLVANIA Avenue Discover an exceptional opportunity to own a beautifully designed luxury home overlooking the prestigious Winter Park Nine Golf Course in one of Winter Park, Florida's most desirable neighborhoods! Built in 2020, this stunning residence offers approximately 3, 500 square feet of thoughtfully designed living space, featuring 4 bedrooms and 4.5 bathrooms. From the moment you step inside, you'll be welcomed by an abundance of natural light, an impressive open-concept floor plan, and soaring ceilings accented by elegant tray ceiling details. Every element of this home comes together to create an atmosphere of sophistication, comfort, and true luxury living. The spacious interior seamlessly blends the living, dining, and entertaining spaces, creating the perfect environment for both everyday living and hosting guests. Step outside to your own private backyard oasis, complete with an amazing pool, perfect for enjoying the beautiful Florida lifestyle. The property also features a spacious two-car garage and a highly desirable in-law suite located above the garage. Complete with its own private kitchen, this separate living space is ideal for extended family, overnight guests, multigenerational living, or a private retreat. Located in one of the most sought-after neighborhoods in Winter Park, this exceptional property offers the opportunity to enjoy golf course living while remaining close to everything that makes Winter Park so special. From its newer construction and light-filled open spaces to its impressive outdoor living area and versatile separate guest quarters, this home delivers the perfect combination of elegance, functionality, and luxury. Don't miss your opportunity to experience this remarkable Winter Park residence!

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Property Features

  • Facts
  • Lot Size: 0.21 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 4
  • 1/2 Bathrooms: 1
  • Cooling System: Central Air
  • Exterior Finish: Outdoor Kitchen, Sidewalk
  • Floor Covering: Marble, Carpet, Tile - Ceramic
  • Roof Type: Metal
  • Heating Fuels: Central, Electric (Heating)
  • Additional Features
  • Patio
  • Pool

School Information

  • School
  • Lakemont Elem(Elementary)
  • Maitland Middle(MiddleSchool)
  • Winter Park High(HighSchool)

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 2500000
  • unparsedaddress: 1008 N PENNSYLVANIA Avenue
  • postalcity: WINTER PARK
  • stateorprovince: FL
  • country: US
  • postalcode: 32789
  • bathroomsfull: 4
  • bathroomshalf: 1
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.21
  • lotsizeunits: Acres
  • lotsizearea: 0.21
  • livingarea: 3530
  • livingareaunits: Square Feet
  • latitude: 28.606352
  • longitude: -81.356681
  • listagentfullname: Joseph Sipp
  • listagentemail: joseph@sipphomegroup.com
  • listagentkey: 3yd-MFRMLSFL-261228330
  • listagentmlsid: 261228330
  • listagentpreferredphone: 4078207016
  • listagentofficephone: 4078207016
  • listofficekey: 3yd-MFRMLSFL-261012230
  • listofficemlsid: 261012230
  • disclaimer: Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: MFRMLSFL
  • yearbuilt: 2020
  • listingcontractdate: 2026-11-13
  • listagentfax: 3212032727
  • countyorparish: Orange
  • parcelnumber: 06-22-30-8580-02-072
  • elementaryschool: Lakemont Elem
  • highschool: Winter Park High
  • appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Refrigerator
  • cooling: Central Air
  • constructionmaterials: Block, Stucco
  • flooring: Marble, Carpet, Tile - Ceramic
  • heating: Central, Electric (Heating)
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 2
  • parkingtotal: 0
  • parkingfeatures: Guest, Off Street, Garage, Open
  • roof: Metal
  • view: Golf Course
  • waterfrontyn: False
  • franchiseaffiliation: Keller Williams Realty
  • interiorfeatures: Ceiling Fans(s), High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Walk-In Closet(s)
  • exteriorfeatures: Outdoor Kitchen, Sidewalk
  • architecturalstyle: Contemporary
  • rooms: Bedroom 2, Bathroom 4, Dining Room, Bedroom 1, Bathroom 1, Bathroom 2, Utility Room, Bedroom 4, Laundry Room, Bathroom 5, Bathroom 3, Family Room, Bedroom 3
  • otherstructures: Outdoor Kitchen
  • utilities: Cable Available
  • patioandporchfeatures: Porch
  • dock: False
  • poolprivateyn: True
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -81.35668, 28.606352
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Keller Williams Winter Park", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"joseph@sipphomegroup.com", "ListBrokerageCity":"Winter Park", "ListBrokerageCountry":"US", "ListBrokerageEmail":"klrw974@kw.com", "ListBrokerageLogoUrl":null, "ListBrokerageName":"Keller Williams Winter Park", "ListBrokeragePhone":"(407) 545-6430", "ListBrokeragePostalCode":"32789", "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"147 W. Lyman Ave", "ListBrokerageWebsiteUrl":null, "ListOfficeAddress1":"147 W Lyman Ave ", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"261012230", "ListOfficeCity":"Winter Park", "ListOfficeCountry":"US", "ListOfficeEmail":"denisel@kw.com", "ListOfficePostalCode":"32789", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Residential, WINTER PARK, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/1008-N-Pennsylvania-Ave_Winter-Park_FL_32789_M61280-68789?f=listhub&s=MFRMLSFL&m=O6457191&c=rexren", "MLSModificationTimestamp":"2026-11-14 11:52:25", "Neighborhoods":[{"Description":null, "Name":"TANTUM ADD"}], "PostalCode":null, "RoomCount":14, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":32016, "TaxDescription":"TANTUM ADDITION TO WINTER PARK C/32 THESOUTH 57.88 FT OF THE NORTH 118.25 FT OFLOT 7 BLK B DESC: COMM AT TH SW CORNERLOT 7 BLOCK B TH N00-00-00W 120.75 FT TOTHE POB TH CONT N00-00-00W 57.88 FT THN89-05-35E 158.7 FT TH S00-00-00W 57.88FT TH S89-05-35W 158.7 FT TO THE POB", "TaxYear":"2026"}], "UnitNumber":null, "UnparsedAddress":null}
  • GarageSpaces: 0
Listing Changed: 11/14/2026 12:05:26 PM GMT
Source Updated Date: 11/15/2026 12:49:26 AM GMT

Courtesy of: Joseph Sipp, KELLER WILLIAMS WINTER PARK, joseph@sipphomegroup.com

Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.