Over five decades later, mid-century architecture and furniture continues to wow people. While most people associate the aesthetic with the suburbs of New York, you don’t have to be commuting to Madison Avenue to find examples of mid-century homes. There are plenty of homes in the Orlando area that will allow you to live like Don Draper.

360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
360 Glenwood Road, Deland PRICE: $900,000 An option for the purist, this Deland home might be the most committed to its mid-century roots.
2244 Howard Drive, Winter Park PRICE: $498,600 This house hits you head on with mid-century vibes from the curb and it doesn’t let up. Space age furnishings and fireplaces make this Winter Park house an absolute time warp.
2244 Howard Drive, Winter Park PRICE: $498,600 This house hits you head on with mid-century vibes from the curb and it doesn’t let up. Space age furnishings and fireplaces make this Winter Park house an absolute time warp.
2244 Howard Drive, Winter Park PRICE: $498,600 This house hits you head on with mid-century vibes from the curb and it doesn’t let up. Space age furnishings and fireplaces make this Winter Park house an absolute time warp.
2244 Howard Drive, Winter Park PRICE: $498,600 This house hits you head on with mid-century vibes from the curb and it doesn’t let up. Space age furnishings and fireplaces make this Winter Park house an absolute time warp.
2244 Howard Drive, Winter Park PRICE: $498,600 This house hits you head on with mid-century vibes from the curb and it doesn’t let up. Space age furnishings and fireplaces make this Winter Park house an absolute time warp.
2244 Howard Drive, Winter Park PRICE: $498,600 This house hits you head on with mid-century vibes from the curb and it doesn’t let up. Space age furnishings and fireplaces make this Winter Park house an absolute time warp.
2244 Howard Drive, Winter Park PRICE: $498,600 This house hits you head on with mid-century vibes from the curb and it doesn’t let up. Space age furnishings and fireplaces make this Winter Park house an absolute time warp.
2244 Howard Drive, Winter Park PRICE: $498,600 This house hits you head on with mid-century vibes from the curb and it doesn’t let up. Space age furnishings and fireplaces make this Winter Park house an absolute time warp.
2244 Howard Drive, Winter Park PRICE: $498,600 This house hits you head on with mid-century vibes from the curb and it doesn’t let up. Space age furnishings and fireplaces make this Winter Park house an absolute time warp.
609 Carvell Drive, Winter Park PRICE: $320,000 The gorgeous floors and eye-catching fireplace make this home a marvel before you even get to the curvy kitchen.
609 Carvell Drive, Winter Park PRICE: $320,000 The gorgeous floors and eye-catching fireplace make this home a marvel before you even get to the curvy kitchen.
609 Carvell Drive, Winter Park PRICE: $320,000 The gorgeous floors and eye-catching fireplace make this home a marvel before you even get to the curvy kitchen.
609 Carvell Drive, Winter Park PRICE: $320,000 The gorgeous floors and eye-catching fireplace make this home a marvel before you even get to the curvy kitchen.
609 Carvell Drive, Winter Park PRICE: $320,000 The gorgeous floors and eye-catching fireplace make this home a marvel before you even get to the curvy kitchen.
609 Carvell Drive, Winter Park PRICE: $320,000 The gorgeous floors and eye-catching fireplace make this home a marvel before you even get to the curvy kitchen.
609 Carvell Drive, Winter Park PRICE: $320,000 The gorgeous floors and eye-catching fireplace make this home a marvel before you even get to the curvy kitchen.
609 Carvell Drive, Winter Park PRICE: $320,000 The gorgeous floors and eye-catching fireplace make this home a marvel before you even get to the curvy kitchen.
609 Carvell Drive, Winter Park PRICE: $320,000 The gorgeous floors and eye-catching fireplace make this home a marvel before you even get to the curvy kitchen.
609 Carvell Drive, Winter Park PRICE: $320,000 The gorgeous floors and eye-catching fireplace make this home a marvel before you even get to the curvy kitchen.
609 Carvell Drive, Winter Park PRICE: $320,000 The gorgeous floors and eye-catching fireplace make this home a marvel before you even get to the curvy kitchen.
609 Carvell Drive, Winter Park PRICE: $320,000 The gorgeous floors and eye-catching fireplace make this home a marvel before you even get to the curvy kitchen.
1000 Noreen Blvd PRICE: 229,000 Floors, fireplaces and oh-so-much wood make this Rockledge home perfect for someone looking to build a swinging pad.
1000 Noreen Blvd PRICE: 229,000 Floors, fireplaces and oh-so-much wood make this Rockledge home perfect for someone looking to build a swinging pad.
1000 Noreen Blvd PRICE: 229,000 Floors, fireplaces and oh-so-much wood make this Rockledge home perfect for someone looking to build a swinging pad.
1000 Noreen Blvd PRICE: 229,000 Floors, fireplaces and oh-so-much wood make this Rockledge home perfect for someone looking to build a swinging pad.
1000 Noreen Blvd PRICE: 229,000 Floors, fireplaces and oh-so-much wood make this Rockledge home perfect for someone looking to build a swinging pad.
1000 Noreen Blvd PRICE: 229,000 Floors, fireplaces and oh-so-much wood make this Rockledge home perfect for someone looking to build a swinging pad.
1000 Noreen Blvd PRICE: 229,000 Floors, fireplaces and oh-so-much wood make this Rockledge home perfect for someone looking to build a swinging pad.
1000 Noreen Blvd PRICE: 229,000 Floors, fireplaces and oh-so-much wood make this Rockledge home perfect for someone looking to build a swinging pad.
1000 Noreen Blvd PRICE: 229,000 Floors, fireplaces and oh-so-much wood make this Rockledge home perfect for someone looking to build a swinging pad.
1000 Noreen Blvd PRICE: 229,000 Floors, fireplaces and oh-so-much wood make this Rockledge home perfect for someone looking to build a swinging pad.
1000 Noreen Blvd PRICE: 229,000 Floors, fireplaces and oh-so-much wood make this Rockledge home perfect for someone looking to build a swinging pad.
511 W Canton Ave, Winter Park PRICE: $3,500,000 An icon of Winter Park. One of the most visually arresting homes in the entire state, mid-century or not.
511 W Canton Ave, Winter Park PRICE: $3,500,000 An icon of Winter Park. One of the most visually arresting homes in the entire state, mid-century or not.
511 W Canton Ave, Winter Park PRICE: $3,500,000 An icon of Winter Park. One of the most visually arresting homes in the entire state, mid-century or not.
511 W Canton Ave, Winter Park PRICE: $3,500,000 An icon of Winter Park. One of the most visually arresting homes in the entire state, mid-century or not.
511 W Canton Ave, Winter Park PRICE: $3,500,000 An icon of Winter Park. One of the most visually arresting homes in the entire state, mid-century or not.
511 W Canton Ave, Winter Park PRICE: $3,500,000 An icon of Winter Park. One of the most visually arresting homes in the entire state, mid-century or not.
511 W Canton Ave, Winter Park PRICE: $3,500,000 An icon of Winter Park. One of the most visually arresting homes in the entire state, mid-century or not.
511 W Canton Ave, Winter Park PRICE: $3,500,000 An icon of Winter Park. One of the most visually arresting homes in the entire state, mid-century or not.
511 W Canton Ave, Winter Park PRICE: $3,500,000 An icon of Winter Park. One of the most visually arresting homes in the entire state, mid-century or not.
511 W Canton Ave, Winter Park PRICE: $3,500,000 An icon of Winter Park. One of the most visually arresting homes in the entire state, mid-century or not.
511 W Canton Ave, Winter Park PRICE: $3,500,000 An icon of Winter Park. One of the most visually arresting homes in the entire state, mid-century or not.
511 W Canton Ave, Winter Park PRICE: $3,500,000 An icon of Winter Park. One of the most visually arresting homes in the entire state, mid-century or not.
511 W Canton Ave, Winter Park PRICE: $3,500,000 An icon of Winter Park. One of the most visually arresting homes in the entire state, mid-century or not.
511 W Canton Ave, Winter Park PRICE: $3,500,000 An icon of Winter Park. One of the most visually arresting homes in the entire state, mid-century or not.
861 Mayfield Avenue, Winter Park PRICE: $999,900 Beyond the gorgeous mid-century sitting room with high, narrow windows and exposed wood beams, this Winter Park sprawler boasts a beautiful interior courtyard.
861 Mayfield Avenue, Winter Park PRICE: $999,900 Beyond the gorgeous mid-century sitting room with high, narrow windows and exposed wood beams, this Winter Park sprawler boasts a beautiful interior courtyard.
861 Mayfield Avenue, Winter Park PRICE: $999,900 Beyond the gorgeous mid-century sitting room with high, narrow windows and exposed wood beams, this Winter Park sprawler boasts a beautiful interior courtyard.
861 Mayfield Avenue, Winter Park PRICE: $999,900 Beyond the gorgeous mid-century sitting room with high, narrow windows and exposed wood beams, this Winter Park sprawler boasts a beautiful interior courtyard.
861 Mayfield Avenue, Winter Park PRICE: $999,900 Beyond the gorgeous mid-century sitting room with high, narrow windows and exposed wood beams, this Winter Park sprawler boasts a beautiful interior courtyard.
861 Mayfield Avenue, Winter Park PRICE: $999,900 Beyond the gorgeous mid-century sitting room with high, narrow windows and exposed wood beams, this Winter Park sprawler boasts a beautiful interior courtyard.
861 Mayfield Avenue, Winter Park PRICE: $999,900 Beyond the gorgeous mid-century sitting room with high, narrow windows and exposed wood beams, this Winter Park sprawler boasts a beautiful interior courtyard.
861 Mayfield Avenue, Winter Park PRICE: $999,900 Beyond the gorgeous mid-century sitting room with high, narrow windows and exposed wood beams, this Winter Park sprawler boasts a beautiful interior courtyard.
861 Mayfield Avenue, Winter Park PRICE: $999,900 Beyond the gorgeous mid-century sitting room with high, narrow windows and exposed wood beams, this Winter Park sprawler boasts a beautiful interior courtyard.
338 Blue Heron Drive, Winter Park PRICE: $760,000 If you love the mid-century modern architectural style but simply can’t go for all the wood and orange hues, this modernized Winter Park home is just the ticket.
338 Blue Heron Drive, Winter Park PRICE: $760,000 If you love the mid-century modern architectural style but simply can’t go for all the wood and orange hues, this modernized Winter Park home is just the ticket.
338 Blue Heron Drive, Winter Park PRICE: $760,000 If you love the mid-century modern architectural style but simply can’t go for all the wood and orange hues, this modernized Winter Park home is just the ticket.
338 Blue Heron Drive, Winter Park PRICE: $760,000 If you love the mid-century modern architectural style but simply can’t go for all the wood and orange hues, this modernized Winter Park home is just the ticket.
338 Blue Heron Drive, Winter Park PRICE: $760,000 If you love the mid-century modern architectural style but simply can’t go for all the wood and orange hues, this modernized Winter Park home is just the ticket.
338 Blue Heron Drive, Winter Park PRICE: $760,000 If you love the mid-century modern architectural style but simply can’t go for all the wood and orange hues, this modernized Winter Park home is just the ticket.
338 Blue Heron Drive, Winter Park PRICE: $760,000 If you love the mid-century modern architectural style but simply can’t go for all the wood and orange hues, this modernized Winter Park home is just the ticket.
338 Blue Heron Drive, Winter Park PRICE: $760,000 If you love the mid-century modern architectural style but simply can’t go for all the wood and orange hues, this modernized Winter Park home is just the ticket.
338 Blue Heron Drive, Winter Park PRICE: $760,000 If you love the mid-century modern architectural style but simply can’t go for all the wood and orange hues, this modernized Winter Park home is just the ticket.
338 Blue Heron Drive, Winter Park PRICE: $760,000 If you love the mid-century modern architectural style but simply can’t go for all the wood and orange hues, this modernized Winter Park home is just the ticket.
338 Blue Heron Drive, Winter Park PRICE: $760,000 If you love the mid-century modern architectural style but simply can’t go for all the wood and orange hues, this modernized Winter Park home is just the ticket.
338 Blue Heron Drive, Winter Park PRICE: $760,000 If you love the mid-century modern architectural style but simply can’t go for all the wood and orange hues, this modernized Winter Park home is just the ticket.
901 Osceola Avenue, Winter Park PRICE: $829,000 This home with a central fireplace and groovy sitting room is nestled between two lakes in Winter Park.
901 Osceola Avenue, Winter Park PRICE: $829,000 This home with a central fireplace and groovy sitting room is nestled between two lakes in Winter Park.
901 Osceola Avenue, Winter Park PRICE: $829,000 This home with a central fireplace and groovy sitting room is nestled between two lakes in Winter Park.
901 Osceola Avenue, Winter Park PRICE: $829,000 This home with a central fireplace and groovy sitting room is nestled between two lakes in Winter Park.
901 Osceola Avenue, Winter Park PRICE: $829,000 This home with a central fireplace and groovy sitting room is nestled between two lakes in Winter Park.
901 Osceola Avenue, Winter Park PRICE: $829,000 This home with a central fireplace and groovy sitting room is nestled between two lakes in Winter Park.
901 Osceola Avenue, Winter Park PRICE: $829,000 This home with a central fireplace and groovy sitting room is nestled between two lakes in Winter Park.
901 Osceola Avenue, Winter Park PRICE: $829,000 This home with a central fireplace and groovy sitting room is nestled between two lakes in Winter Park.
901 Osceola Avenue, Winter Park PRICE: $829,000 This home with a central fireplace and groovy sitting room is nestled between two lakes in Winter Park.
901 Osceola Avenue, Winter Park PRICE: $829,000 This home with a central fireplace and groovy sitting room is nestled between two lakes in Winter Park.
901 Osceola Avenue, Winter Park PRICE: $829,000 This home with a central fireplace and groovy sitting room is nestled between two lakes in Winter Park.
901 Osceola Avenue, Winter Park PRICE: $829,000 This home with a central fireplace and groovy sitting room is nestled between two lakes in Winter Park.
901 Osceola Avenue, Winter Park PRICE: $829,000 This home with a central fireplace and groovy sitting room is nestled between two lakes in Winter Park.
2126 Greenway Drive, Winter Haven PRICE: $230,000 Make an offer on this house and see if they’ll throw in the era-perfect furniture.
2126 Greenway Drive, Winter Haven PRICE: $230,000 Make an offer on this house and see if they’ll throw in the era-perfect furniture.
2126 Greenway Drive, Winter Haven PRICE: $230,000 Make an offer on this house and see if they’ll throw in the era-perfect furniture.
2126 Greenway Drive, Winter Haven PRICE: $230,000 Make an offer on this house and see if they’ll throw in the era-perfect furniture.
2126 Greenway Drive, Winter Haven PRICE: $230,000 Make an offer on this house and see if they’ll throw in the era-perfect furniture.
2126 Greenway Drive, Winter Haven PRICE: $230,000 Make an offer on this house and see if they’ll throw in the era-perfect furniture.
300 W Lake Summit Drive SE PRICE: $1,620,000 One of the pricier entries on this already expensive list but one look inside tells you why. (Being on the water doesn’t hurt, either.)
300 W Lake Summit Drive SE PRICE: $1,620,000 One of the pricier entries on this already expensive list but one look inside tells you why. (Being on the water doesn’t hurt, either.)
300 W Lake Summit Drive SE PRICE: $1,620,000 One of the pricier entries on this already expensive list but one look inside tells you why. (Being on the water doesn’t hurt, either.)
300 W Lake Summit Drive SE PRICE: $1,620,000 One of the pricier entries on this already expensive list but one look inside tells you why. (Being on the water doesn’t hurt, either.)
300 W Lake Summit Drive SE PRICE: $1,620,000 One of the pricier entries on this already expensive list but one look inside tells you why. (Being on the water doesn’t hurt, either.)
300 W Lake Summit Drive SE PRICE: $1,620,000 One of the pricier entries on this already expensive list but one look inside tells you why. (Being on the water doesn’t hurt, either.)
300 W Lake Summit Drive SE PRICE: $1,620,000 One of the pricier entries on this already expensive list but one look inside tells you why. (Being on the water doesn’t hurt, either.)
300 W Lake Summit Drive SE PRICE: $1,620,000 One of the pricier entries on this already expensive list but one look inside tells you why. (Being on the water doesn’t hurt, either.)

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