Homes for Sale in Winter Park

Lake bordered by homes and docks, with tropical plants in the foreground and storm clouds overhead.

Property Listings

Price

Living Area

Two-story white residential building with screened balconies, exterior staircases, and palm trees.

$269,000

151 N ORLANDO AVE #242, WINTER PARK, FL 32789

2 Beds 1 Bath 710 Sq.Ft.

Teal-and-white single-story house with a screened porch beneath large oak trees.

$965,000

471 HOLT AVE, WINTER PARK, FL 32789

4 Beds 3 Baths 2,528 Sq.Ft.

White split-level home with a long garage, covered porch, and broad concrete driveway, viewed from above.

$1,200,000

1220 HOWELL BRANCH RD, WINTER PARK, FL 32789

3 Beds 2 Baths 1,487 Sq.Ft.

Two-story white stucco home with terracotta tile roofs, arched entry, and tropical landscaping.

$1,795,000

1230 SUNSET DR, WINTER PARK, FL 32789

4 Beds 3.5 Baths 3,250 Sq.Ft.

Low white mid-century modern home with a covered carport, broad lawn, and mature palms.

$430,000

2015 TAYLOR AVE, WINTER PARK, FL 32792

3 Beds 2 Baths 1,439 Sq.Ft.

Modern white two-story house with dark double garage doors, tall entry windows, and a broad green lawn.

$1,598,000

2430 CHANTILLY AVE, WINTER PARK, FL 32789

4 Beds 4 Baths 2,916 Sq.Ft.

Covered wooden dock extending into a calm lake, with a grassy shoreline and mature trees.

$1,600,000

2207 KINDEL AVE, WINTER PARK, FL 32789

3 Beds 2.5 Baths 2,733 Sq.Ft.

Single-story ranch home with brick accents, a turquoise front door, and an attached garage.

$425,000

2126 ALBERT LEE PKWY, WINTER PARK, FL 32789

3 Beds 2 Baths 1,187 Sq.Ft.

White two-story home with blue-gray shutters, brick driveway, and warmly lit windows at dusk.

$2,699,000

1597 OAKHURST AVE, WINTER PARK, FL 32789

5 Beds 4.5 Baths 4,410 Sq.Ft.

Large white two-story home with dark roofs, stone accents, and formal landscaped gardens.

$3,265,000

1761 LEGION DR, WINTER PARK, FL 32789

5 Beds 5.5 Baths 4,924 Sq.Ft.

Two-story white house with pale brick, black-framed windows, a double garage, and landscaped front lawn.

$1,950,000

751 PANSY AVE, WINTER PARK, FL 32789

3 Beds 3.5 Baths 2,703 Sq.Ft.

Two-story stucco home with an arched entry, balcony, terracotta roof, and curved brick driveway.

$3,600,000

276 DETMAR DR, WINTER PARK, FL 32789

4 Beds 5 Baths 4,202 Sq.Ft.

Two-story stone-and-stucco home with twin garage doors, front lawn, and paved driveway.

$1,829,000

1550 PALM AVE, WINTER PARK, FL 32789

4 Beds 3.5 Baths 2,706 Sq.Ft.

Two-story apartment building with exterior walkways and stairs beside a parking lot.

$245,000

1250 S DENNING DR #Unit 233, WINTER PARK, FL 32789

2 Beds 2 Baths 913 Sq.Ft.

Single-story gray home behind a large mature tree, with a broad lawn and front walkway.

$795,000

325 N PHELPS AVE, WINTER PARK, FL 32789

Aerial view of a wooded vacant lot outlined in yellow among neighboring homes.

Active Under Contract

$1,800,000

1220 SHARON PL, WINTER PARK, FL 32789

Attached homes at dusk with glowing windows and landscaped front entrances.

$285,000

283 SANDLEWOOD TRL #3, WINTER PARK, FL 32789

2 Beds 2.5 Baths 960 Sq.Ft.

Gray detached two-car garage with white doors, a wide driveway, and mature shade trees.

$660,000

1016 ARAGON AVE, WINTER PARK, FL 32789

4 Beds 4 Baths 1,840 Sq.Ft.

Gray single-story home with a covered porch, attached garage, and curved paver driveway.

$1,495,000

150 E READING WAY, WINTER PARK, FL 32789

3 Beds 2.5 Baths 2,080 Sq.Ft.

Aerial view of a white-outlined residential lot, with a house, mature trees, and a lake beyond.

$1,875,000

1661 LAUREL RD, WINTER PARK, FL 32789

3 Beds 3 Baths 3,127 Sq.Ft.

White single-story house with dark shutters, covered entry, and brick-paved driveway.

$589,900

1313 S DENNING DR, WINTER PARK, FL 32789

3 Beds 2 Baths 1,700 Sq.Ft.

Dark single-story home with a modern entry, gabled roof, and paved front walkway.

$689,000

900 CARVER ST, WINTER PARK, FL 32789

3 Beds 3 Baths 1,794 Sq.Ft.

White single-story home with reddish roof trim on a broad grassy lot beneath mature trees.

$675,000

1416 BORDER DR, WINTER PARK, FL 32789

Single-story home with a broad carport and red awnings at dusk.

$340,000

1941 OGLESBY AVE, WINTER PARK, FL 32789

2 Beds 1 Bath 780 Sq.Ft.

Beige condominium building with balconies, an exterior staircase, palm trees, and manicured landscaping.

$1,050,000

311 E MORSE BLVD #4-5, WINTER PARK, FL 32789

2 Beds 2 Baths 1,763 Sq.Ft.

151 N Orlando Ave 261

$239,999

151 N ORLANDO AVE #261, WINTER PARK, FL 32789

1 Bed 1 Bath 582 Sq.Ft.

Light blue single-story house with a double garage, front lawn, and wide concrete driveway.

$899,000

1621 CHESTNUT AVE, WINTER PARK, FL 32789

3 Beds 2.5 Baths 2,022 Sq.Ft.

Aerial view of tree-lined Winter Park homes with landscaped lawns and paved driveways.

$1,350,000

720 PANSY AVE, WINTER PARK, FL 32789

3 Beds 4 Baths 2,191 Sq.Ft.

565 Huntington Ave 565

$635,000

565 HUNTINGTON AVE #565, WINTER PARK, FL 32789

3 Beds 2.5 Baths 2,015 Sq.Ft.

Single-story stucco home with green trim, a red front door, and a palm tree beside the driveway.

$689,900

943 FAIRWAY DR, WINTER PARK, FL 32792

4 Beds 3 Baths 2,067 Sq.Ft.

Two-story white and gray brick home with an arched entry and paver driveway at dusk.

Active Under Contract

$3,999,000

1417 WILLIAMS DR, WINTER PARK, FL 32789

5 Beds 5.5 Baths 4,891 Sq.Ft.

Aerial view of leafy homes with red tile roofs and round towers.

$799,000

1278 S PENNSYLVANIA AVE #13, WINTER PARK, FL 32789

3 Beds 2.5 Baths 1,957 Sq.Ft.

Brick house with a terracotta tile roof, double garage, wide driveway, and landscaped front yard.

$660,000

1256 MELISSA CT, WINTER PARK, FL 32789

3 Beds 3 Baths 1,690 Sq.Ft.

Park West condominium entrance with a sign, gated driveway, landscaped island, and palm trees.

$739,000

250 CAROLINA AVE #205, WINTER PARK, FL 32789

2 Beds 2 Baths 1,311 Sq.Ft.

Two-story white house with a columned entry, attached garage, and tree-shaded lawn.

Active Under Contract

$2,750,000

948 POINCIANA LN, WINTER PARK, FL 32789

4 Beds 4.5 Baths 3,676 Sq.Ft.

White stucco home with a tile roof, covered entry, and curving brick driveway.

$649,000

1409 SUNSET DR, WINTER PARK, FL 32789

2 Beds 1.5 Baths 1,107 Sq.Ft.

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