| 1 | The Laughing Cow | Restaurant | | | | | | | | |
| 2 | Reese Grocery & Vegetables | Food | | | | | http://portal.charlamov.com/windlebridge/Houses%20Pictures/_t/allison2_jpg.jpg | | | |
| 3 | Barber | Hairdresser | | | | | | | | |
| 4 | Tailor | Clothing | | | | | | | | |
| 5 | Westby Wagons & Horses | Retail | | 10 | This is where you can find the wagons and horses you need, and also all kinds of equipment for your barn and farm.
| | http://portal.charlamov.com/windlebridge/Houses_Pictures/_t/wagonshorses1_jpg.jpg | Peter Westby | | Read more |
| 6 | Smith | Retail | | | | | | | | |
| 7 | Allison's Butcher Shop | Food | | | | | | | | |
| 8 | Fay Potions | Retail | | | | | | | | |
| 9 | Windle Mine | Mine | | 6 | The source of riches, not only for the Windleton family | | Windle Mine in springtime | Sir Patrick Windleton | | Read more |
| 10 | Manor Orchard | Farm | | | Where the Windleton family grow apples | | Manor Orchard | | | Manor Orchard |
| 11 | Manor Fields | Farm | | | Where the Windelton family grow vegetables. | | Manor Fields | Sir Patrick Windleton | | Manor Fields |
| 12 | Village Square | Mixed | | | A popular gathering spot for the villagers, all year round and all days. | | http://portal.charlamov.com/windlebridge/Houses_Pictures/_t/villagesquare_jpg.jpg | | | |
| 13 | Blossom Pond | Other | | | A place to cool off and take a swim on hot summer days. | | Blossom Pond | | | |
| 14 | Ice Pond | Other | | | | | | | | |
| 15 | Fishing Pond | Other | | | Come here to swim and fish. | | Fishing Pond | | | |
| 16 | Gypsy Camp | Other | | | The gathering place for the gypsies in Windlebridge, where music is always played. | | http://portal.charlamov.com/windlebridge/Houses_Pictures/_t/weddingnightcamp_jpg.jpg | | | |
| 17 | Bakery | Food | | | | | | | | |
| 18 | Windlebridge Church | Religion | | 10 | | | Windlebridge Church | Horace Bell | | |
| 19 | Carpenter | Retail | | | A new bed, a nice cupboard, a chair to sit on - come to the carpenters! | | http://portal.charlamov.com/windlebridge/Houses_Pictures/_t/carpenter_jpg.jpg | Dale Carpenter | | |
| 20 | Central Square | Mixed | | | | | http://portal.charlamov.com/windlebridge/Houses_Pictures/_t/collegesquareeast_jpg.jpg | | | |
| 21 | College Baths | Education | | | | | http://portal.charlamov.com/windlebridge/Houses_Pictures/_t/collegebaths_jpg.jpg | | | |
| 22 | The Merry Madame | Entertainment; Restaurant | | | | | http://portal.charlamov.com/windlebridge/Pictures/_t/merrymadame4_jpg.jpg | | | |
| 23 | Castle Park | Other | | | | | Castle Park | Lord Ian Lennox | | Read more |
| 24 | Castle Gardens | Other | | 2 | | | Castle Gardens | Lord Ian Lennox | | Read more |
| 25 | River Swimming Spot | Other | | | | | River Swimming Spot in Winter | | | |
| 26 | Garrison Training Fields | Other | | 1 | Sweat, blood and no tears - where men train to go to war. | | The Training Fields | Lord Ian Lennox | | |
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| 28 | The Hawk and the Pidgeon | Restaurant | | 3 | Drink a beer, have some pie, win some money and meet the girls of The Hawk and Pidgeon | | The Hawk and the Pidgeon | Almond Sudder | | |
| 29 | Fay Apothekary | Retail | | 2 | Potions and remedies - made by skilled and experienced potion makers. | | Apothekary | Merlin Fay | | Read more |
| 30 | Hotel Albertina | Restaurant | | | A nice restaurant and hotel, right next to Old Town Square | | Hotel Albertina | | | Read more |
| 31 | Westby Toy Store | Retail | | | Find the toys your sim kids crave here! | | Westby Toy Store | Matthew Westby | | Read more |
| 32 | The Dancing Pony | Restaurant | | | A very popular restaurant and bar on Shoemaker Street. | | The Dancing Pony | Vernon Sherry | | |
| 33 | Old Town Square & Town Hall | Other | | | The big square in Old Town, and the Town Hall where the City Council meets. | | Old Town Square & Town Hall | | | Read more |
| 34 | Ashton Clothing Atelier | Clothing | | 2 | Lavinia Ashtons Clothing Atelier for Ladies Wear | | Ashton Clothing Atelier | Lavinia Ashton-Paynter | | Read more |
| 35 | Catfish Island | Fishing | | | Erwin Swann uses this small island just outside the Harbour for his fishing company. | | Catfish Isand | Erwin Swann | | Read More |
| 37 | The Rose Garden | Other | | | | | The Rose Garden, springtime | Sir Patrick Windleton | | Read more |
| 38 | The Pottery | Retail | | | Making pots for all purposes | | The Pottery | Arnold Potter | | Read more |
| 39 | Bothanical Garden | Education | | | A place to study the nature | | Bothanical Garden | | | Read more |
| 40 | The Alchemy Institute | Education | | | Hot spot for science sims | | The Alchemy Institute | | | Read more |
| 41 | Library of Literature | Education | | | For the bookworms | | | | | Read more |
| 42 | Museum of Art | Education | | | Come here to see the beautiful paintings | | | | | Read more |
| 43 | Field of Sports | Education | | | Where the games are held | | Field of Sports | | | Read more |
| 44 | College Main Hall | Education | | | Central administrative building of Windle College | | College Main Hall | | | Read more |
| 45 | St Jacob Church | Religion | | | The church of Windle College | | St Jacob Church | | | Read more |
| 46 | Alchemy Institute | Education | | | Centre for Science and Research | | Alchemy Institute | | | Read more |
| 47 | Gypsy Beach | Entertainment | | | When the gypsies came to Windleport, they were showed to set up camp on the beach just outside the city wall. | | | | | Read more |
| 48 | South Castle Corner | Entertainment | | | In this part of the castle the Lennox family arrange their famous ball dances and receptions. | | Castle South Corner | Lord Ian Lennox | | |
| 49 | Clay Jewellery Shop | Retail | | | Alan Clay sells both finer and simpler jewellery. | | Clay Jewellery Store | | | Read more |
| 50 | North Grocery Store | Food | | | | | North Grocery Store | | | Read more |
| 51 | Fish Market | Food | | | Where Erwin Swann sells his fish | | Fish Market | | | Read more |
| 52 | Cloister Baths | Other | | | Come here to get clean and fit. | | Cloister Baths | | | Read more |
| 53 | Village Council | Administrative | | | The Village Council of Windlebridge | | Village Council | | | Read more |
| 54 | Windlebridge Sports Field | Other | | | Come here to play soccer and basket. | | Windlebridge Sports Field | | | |
| 55 | Falcon Crest Inn | Restaurant | | | Elegant and comfortable Inn for the guests of the Castle. | | Falcon Crest Inn | | | Read more |