Winter Park, FL Multifamily properties for sale

Income-Producing Duplex in Central Orlando

$415,000

1,197 SF

Income-Producing Duplex in Central Orlando

1518 Pinewood Dr, Winter Park, FL 32789

Duplex with detached in-law apartment, ideal for rental.

Income‑producing property with detached in‑law apartment, ideal for house hacking or rental income.
Prime central Orlando location near Winter Park, College Park, Downtown Orlando, and major amenities.
Detached in‑law apartment currently rented for $1,350/month, providing immediate income.
Main house previously rented for $1,850/month, demonstrating strong rental history.
Separate entrances and mailboxes for both units ensure privacy and flexibility.

Updated: Mar 3

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Winter Park Triplex Investment Opportunity

$7,150,000

12,500 SF

Winter Park Triplex Investment Opportunity

2412 Chantilly Ave, Winter Park, FL 32789

Luxury triplex in a fast-growing market with income potential.

High short‑term rental returns reaching up to 13%.
Significant first‑year cost‑segregation deductions (approximately $679,000 for long‑term rentals and $850,000 for short‑term rentals).
Located in booming Central Florida where property values surged 164% over the past decade.
Dual‑lane income potential with both long‑term and short‑term rentals.
New construction built in 2026.

Updated: Feb 19

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Based on your search, we've compiled 8 Potential Opportunities for your consideration. Besides 2 Active listings in Winter Park, FL, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 2 Off-Market properties to explore as potential leads

Explore Opportunities in Nearby Cities

Here are 4 Similar properties we found in Nearby Locations for your consideration.

$419,900

1,680 SF

Updated Duplex in Eatonville

Updated duplex with new roof, HVAC, and updated interiors.

385 Lime St, Maitland, FL 32751

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College Park Multifamily Investment Opportunity

Pending

$1,250,000

3,201 SF

College Park Multifamily Investment Opportunity

Six-unit property in Orlando's College Park neighborhood.

35 E Winter Park St, Orlando, FL 32804

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7,000 SF

Mixed-Use Property in Ivanhoe Village

Rare 7,000 SF mixed-use property in Orlando's Ivanhoe Village.

2020 N Orange Ave, Orlando, FL 32804

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$419,900

Eatonville Duplex: Investment Opportunity

Duplex in historic Eatonville with recent upgrades and strong rental income.

385 Lime St, Maitland, FL 32751

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Explore 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.

500 Knowles Ave

BOARDING/ROOMING HOUSE • 4,518 SF

Value Estimation

$600,000

500 Knowles Ave, Winter Park, FL 32789-3231

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1099 Clay St

HIGH-RISE APARTMENTS • 131,680 SF

Value Estimation

$3,600,000

1099 Clay St, Winter Park, FL 32789-5474

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Winter Park, FL Multifamily Properties Investment Opportunities Market Analysis

Explore 4 multifamily properties for sale in Winter Park, FL on our real estate platform. These investment opportunities span a total of 20,038 square feet of properties for sale, with an estimated market value of $7,575,000.

Sale prices for multifamily properties in Winter Park, FL start at $425,000, averaging $3,787,500, and reaching up to $7,150,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

Winter Park, FL Multifamily Properties for Sale

Income-Producing Duplex in Central Orlando

Duplex with detached in-law apartment, ideal for rental.

Winter Park Triplex Investment Opportunity

Luxury triplex in a fast-growing market with income potential.