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Maitland Shores Winter Park Florida Homes For Sale

Below you can view all the homes for sale in the Maitland Shores subdivision located in Winter Park Florida. Listings in Maitland Shores are updated daily from data we receive from the Orlando multiple listing service.

To learn more about any of these homes or to receive custom notifications when a new property is listed for sale in Maitland Shores, give us a call at 407-278-2057.

Maitland Shores | For Sale

$1,949,000

View 2235 Via Tuscany Winter Park FL
View 2235 Via Tuscany Winter Park FL
View 2235 Via Tuscany Winter Park FL
Listed For 11 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5190

  • Year Built

    2000

  • $/SqFt

    $375

Walk to Winter Park Racquet Club. Winter Park Schools. MLS#O5770369. Fannie Hillman & Associates. MFR

Maitland Shores | For Sale

$1,625,000

View 906 Poinciana Ln Winter Park FL
View 906 Poinciana Ln Winter Park FL
View 906 Poinciana Ln Winter Park FL
Listed For 13 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3309

  • Year Built

    2009

  • $/SqFt

    $491

With its supreme sense of privacy, elegant finishes and proximity to commuter roads, it is no wonder that this brilliant masterpiece estate is the Parade of Homes Winner! MLS#O5769819. Regal R.E. Professionals Llc. MFR

Maitland Shores | For Sale

$1,895,000

View 2229 Via Tuscany Winter Park FL
View 2229 Via Tuscany Winter Park FL
View 2229 Via Tuscany Winter Park FL
Listed For 22 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4329

  • Year Built

    1999

  • $/SqFt

    $437

Don't miss seeing this one! MLS#O5765009. Tmp Premier Real Estate Llc. MFR

Maitland Shores | For Sale

$1,895,000

View 2031 Venetian Way Winter Park FL
View 2031 Venetian Way Winter Park FL
View 2031 Venetian Way Winter Park FL
Listed For 44 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3556

  • Year Built

    1969

  • $/SqFt

    $532

Boat, kayak, paddleboard or ride your jet skis through the 6 lakes connected by beautiful canals and enjoy all that the lake lifestyle has to offer. MLS#O5762356. Premier Sothebys Intl. Realty. MFR

Maitland Shores | For Sale

$1,150,000

Reduced By $45,000

Listed For 109 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3999

  • Year Built

    2003

  • $/SqFt

    $287

Great care and attention has gone into maintaining this fabulous residence in a prime location to enjoy all the conveniences of living in Olde Winter Park and the sought-after Via's neighborhood. MLS#O5749535. Premier Sothebys Intl. Realty. MFR

Maitland Shores | For Sale

$394,500

Listed For 110 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1948

  • Year Built

    1953

  • $/SqFt

    $202

Call to schedule a showing today!!! ! MLS#S5009767. The Property Pros Real Estate,. MFR

Maitland Shores | Pended

$1,999,000

Reduced By $101,000

Listed For 131 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3515

  • Year Built

    1959

  • $/SqFt

    $568

Don't miss this incredible opportunity to live on the Winter Park Chain of Lakes. MLS#O5747101. Fannie Hillman & Associates. MFR

Maitland Shores | For Sale

$1,195,000

Reduced By $50,000

Listed For 147 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3883

  • Year Built

    2005

  • $/SqFt

    $307

Immaculately cared for this home is a must see! MLS#O5742932. Kelly Price & Company Llc. MFR

Maitland Shores | For Sale

$2,250,000

Reduced By $400,000

Listed For 203 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4875

  • Year Built

    2008

  • $/SqFt

    $461

It's even better in person! MLS#O5731623. Collado Real Estate. MFR

Maitland Shores | Pended

$795,000

Reduced By $153,000

Listed For 210 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2820

  • Year Built

    1954

  • $/SqFt

    $281

Don't miss your opportunity to own this amazing "Old Florida" style home or fantastic building site! MLS#O5729038. Homevest Realty. MFR

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