Winter Park, FL Residential Income Properties for Sale

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Updated: Aug 23

Duplex with Private Entrances

1016 ARAGON Avenue, Winter Park, FL 32789

$660,000

1,840 sqft 0.16 AC lot

Two‑unit property with 4 bedrooms, 2 full baths, and 2 half baths
1,840 square feet on a 0.16‑acre lot
R‑2 zoning in Winter Park, FL
Each unit includes two bedrooms, a Jack‑and‑Jill bath, and a half bath
Private entrances, fenced courtyard, patio, and private pool

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Updated: Aug 23

Fenced Duplex with Private Pool

1016 ARAGON Avenue, Winter Park, FL 32789

$660,000

1,840 sqft 0.16 AC lot

1,840‑square‑foot duplex on a 0.16‑acre lot
Four bedrooms, two full bathrooms, and two half bathrooms total
Each unit includes two bedrooms, a Jack‑and‑Jill bathroom, and a half bathroom
Private pool with fenced grounds and separate entrances
Built in 1983 with block construction, tile flooring, and a metal roof

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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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See what stands out in Orange County

We check every for-sale listing in the county against comparable properties across the country. Most price about where you would expect. A few are worth a second look.

We check every listing here. A few are worth a second look.

Cap Rate available after sign in

NOI available after sign in

Local Demand available after sign in

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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Duplex Property with Corner Lot

3302 ROYAL Street, Winter Park, FL 32792

$279,900

1,197 sqft 0.14 AC lot

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

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Two-Unit Duplex with Patios

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

$1,185,999

2,282 sqft 0.09 AC lot

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

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Two-Bedroom Duplex Unit

2712 TORTOISE CV, Winter Park, FL 32792

$235,000

924 sqft 0.13 AC lot

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

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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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Refreshed Two-Bedroom Duplex

5444 PEACO Place, Winter Park, FL 32792

$250,000

924 sqft 0.12 AC lot

R2-zoned property with an open layout, fenced backyard, and public water and sewer in Winter Park.

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Single-Story Duplex Property

5781 SHALE Court, Winter Park, FL 32792

$300,000

1,086 sqft 0.20 AC lot

Two-bedroom, two-bath layout with screened outdoor space and public utilities.

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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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Waterfront Residential Development Site

1009 LAKE BELL Drive, Winter Park, FL 32789

$650,000

0.47 AC lot

Residentially zoned waterfront homesite with canal frontage on Lake Bell and direct lake access.

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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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Leased Two-Unit Duplex

2183 CRANDON AVENUE, Winter Park, FL 32789

$499,000

1,200 sqft

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

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Duplex Property with Screened Patio

Winter Park, FL 32792

$300,000

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

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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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Short-Term Rental Property

2412 Chantilly Ave, Winter Park, FL 32789

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Winter Park asset completed in 2026 with both short-term and long-term rental positioning.

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Land, Multifamily

1057 Minnesota Ave., Winter Park, FL 32789

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Multifamily properties

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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

$3,600,000

Estimated value

131,680 sqft 0.16 AC lot

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BOARDING/ROOMING HOUSE

500 Knowles Ave, Winter Park, FL 32789-3231

$600,000

Estimated value

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 19,595 square feet of properties for sale, with an estimated market value of $8,939,799.

Sale prices for residential income properties in Winter Park, FL start at $235,000, averaging $558,737, and reaching up to $1,185,999 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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Top Commercial Asset Segments

Commercial property segments ranked by active listings on the market

Demographics Overview

Population 80K

Population Growth (5Y) +2.4%

Median Household Income $77,660

College Educated 37.4%

High-Yield Neighborhoods for Investment

Identify Winter Park submarkets with the highest inventory density on the market and evaluate the average listing prices of real estate assets

Neighborhood	Average Price
32792	$335K
32789	$701.9K

Taxes & Financing

Tax Rate (average for all types) 1.38%

Property Tax per SF $12.70 per SF

Tax Rate vs County Average 0.18 pp below county avg

Average Loan-to-Value 65.0%

Listings Trend

New vs delisted commercial listings in Orange County

New Delisted

Total CRE Inventory on Market (SF)

Property Size Breakdown

The majority of commercial real estate listings in Winter Park fall within the 100,000+ square foot range.

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