Winter Park, FL Residential income properties for sale

Updated: Oct 16

12-Unit Mixed-Use Property

271 S ORLANDO Avenue, Winter Park, FL 32789

$1,550,000

3,430 sqft 0.18 AC lot

12 short‑term rental units: 8 studios and 4 one‑bedroom/one‑bath units
Street‑facing office suite on S. Orlando Avenue
3,430 square feet on 0.18 acres
C‑3 zoning
Built in 1949; block and stucco construction

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Updated: Aug 23

Two-Unit Duplex with Pool

1016 ARAGON Avenue, Winter Park, FL 32789

$625,000

1,840 sqft 0.16 AC lot

Two residential units, each with two bedrooms, a Jack‑and‑Jill bath, and a half bath
1,840 square feet on a 0.16‑acre lot
Private in‑ground pool and fenced exterior
Built in 1983; block construction with a metal roof
R‑2 zoning; public water and public sewer

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Two-Unit Duplex with Pool

1016 ARAGON Avenue, Winter Park, FL 32789

$625,000

1,840 sqft 0.16 AC lot

Each residence offers two bedrooms, a Jack-and-Jill bathroom, and a half bath.

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Income Duplex with Fenced Yards

5427 PEACO PLACE, Winter Park, FL 32792

$550,000

1,974 sqft

Two rental units include granite counters and fenced yards, with a 3-bed 2-bath and a 2-bed 1-bath configuration.

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Corner-Lot Duplex

901 HARMON Avenue, Winter Park, FL 32789

$650,000

1,277 sqft 0.13 AC lot

R-2-zoned duplex with private entrances, covered driveway parking, and separate living and dining areas.

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Two-Unit Duplex with Patios

726/720 N PENNSYLVANIA Avenue, Winter Park, FL 32789

$999,000

2,282 sqft 0.09 AC lot

Two residential units offer private fenced patios, in-unit laundry, and parking.

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Duplex Property with Corner Lot

3302 ROYAL Street, Winter Park, FL 32792

$269,900

1,197 sqft 0.14 AC lot

Three-bedroom residence with ceramic tile flooring, granite kitchen counters, and no HOA.

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Corner Lot Duplex With Updates

901 HARMON AVENUE, Winter Park, FL 32789

$650,000

1,277 sqft

Duplex on a corner lot with recent roof, window, exterior paint, and updated ACs.

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Two-Bedroom Duplex Unit

2712 TORTOISE CV, Winter Park, FL 32792

$230,000

924 sqft 0.13 AC lot

Open-plan residence with ceramic tile flooring, central air, and no HOA.

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Five-Bedroom Duplex with Private Yard

1421 MICHIGAN Avenue, Winter Park, FL 32789

$586,567

2,031 sqft 0.16 AC lot

Two separate residences combine practical layouts, updated flooring, ceiling fans, and off-street parking in Winter Park.

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Leased Two-Unit Duplex

2183 CRANDON AVENUE, Winter Park, FL 32789

$469,000

1,200 sqft

Two-bedroom units include private entrances, central AC, and screened patio areas.

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Land, WINTER PARK, FL

7839 UNIVERSITY GARDEN Drive, Winter Park, FL 32792

$1,000,000

4.93 AC lot

Residential land & home lots · 4.93 Acres

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Duplex with Separate Residences

1016 ARAGON AVENUE, Winter Park, FL 32789

$660,000

1,840 sqft

Each side offers two bedrooms, a Jack-and-Jill bath, and a half bath.

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Duplex Property with Screened Patio

Winter Park, FL 32792

$307,500

One-story residential property with two bedrooms, two full bathrooms, and a covered, screened outdoor area.

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Five-Bedroom Duplex

1421 MICHIGAN AVE, Winter Park, FL 32789

$586,567

Two residences offer distinct layouts, existing appliances, and a mix of luxury vinyl and tile flooring.

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Multifamily Property

617 North Interlachen Avenue, Winter Park, FL 32789

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Multifamily property located on North Interlachen Avenue in Winter Park.

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12-Unit Mixed-Use Property

271 South Orlando Avenue, Winter Park, FL 32789

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A separate office suite fronts South Orlando Avenue alongside the furnished-rental component.

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Duplex with Recently Replaced Roof

3128 PATEL DRIVE, Winter Park, FL 32792

$409,900

1,934 sqft

Separate two-bedroom, two-bath units feature tiled or laminate floors, appliances, laundry hookups, and partially fenced backyards.

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Based on your search, we've compiled Potential Opportunities for your consideration. Besides 18 Active Listings in Winter Park, FL, we suggest to view alternatives - similar 2 Off-Market properties to explore as potential leads.

Off-Market Properties in Winter Park, FL

Consider similar Off-Market properties in Winter Park, FL. You may contact the owners directly to inquire about their potential intentions to sell. To help you make a strong first impression, we can assist by reaching out to these owners with compelling proposals created using our AI tool.

HIGH-RISE APARTMENTS

1099 Clay St, Winter Park, FL 32789-5474

Estimated value:

$3,600,000

131,680 sqft 0.16 AC lot

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BOARDING/ROOMING HOUSE

500 Knowles Ave, Winter Park, FL 32789-3231

Estimated value:

$600,000

4,518 sqft 0.27 AC lot

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Winter Park, FL Residential Income Properties Market Trends and Statistics

Explore 20 residential income properties for sale in Winter Park, FL, showcased through 18 active listings on our real estate platform. These investment opportunities span a total of 23,046 square feet of properties for sale, with an estimated market value of $10,168,434.

Sale prices for residential investment properties in Winter Park, FL start at $230,000, averaging $635,527, and reaching up to $1,550,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

Neighborhood	Average Price
32792	$462.1K
32789	$680.9K

Neighborhood

Average Price

32792

$462.1K

32789

$680.9K