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The buying timeline

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Closing costs, itemized
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Residential
Commercial

91 listings

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91 listings

Apartments and Houses for Rent in Winter Park, FL

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24 of 91 Listings

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24 of 91 Listings

New28

Active

$4,100/mo

3 bd · 3 ba · 2,196 sqft

2227 Howard Dr, Winter Park, FL

Simone Pinto de Almeida Santos · NOVA REAL ESTATE SERVICES INC

New14Active

$4,000/mo

4 bd · 4 ba · 2,664 sqft

432 W Swoope Ave, Winter Park, FL

Edward Bonner · COLDWELL BANKER REALTY

37Active

$2,450/mo

3 bd · 3 ba · 1,872 sqft

7498 Aloma Pines Ct, Winter Park, FL

Marian Coaxum · KELLER WILLIAMS REALTY AT THE PARKS

29Active

$2,840/mo

3 bd · 2 ba · 1,295 sqft

408 London Rd, Winter Park, FL

Angela Fettig · KELLER WILLIAMS REALTY AT THE PARKS

20Active

$2,250/mo

3 bd · 2 ba · 1,080 sqft

3005 Casselwood St, Winter Park, FL

Chanmarlie Lim · HOME WISE REALTY GROUP, INC.

25Active

$1,795/mo

2 bd · 3 ba · 1,090 sqft

3027 Aaron Burr Ave #L1, Winter Park, FL

Jocelyne Yanez · HOMESMART

11Active

$2,900/mo

3 bd · 2 ba · 1,364 sqft

1051 Turner Rd, Winter Park, FL

Ranah Nam · SOGO REAL ESTATE SERVICES LLC

68Active

$5,700/mo

3 bd · 4 ba · 2,860 sqft

98 S Virginia Ave #111, Winter Park, FL

Anthony Consalvo · FLORIDA ONE REAL ESTATE LLC

54Active

$3,900/mo

4 bd · 2 ba · 2,548 sqft

7797 Broken Arrow Trl, Winter Park, FL

Claudia D'Aquino · CENTURY 21 CARIOTI

31Active

$2,500/mo

3 bd · 2 ba · 3,950 sqft

1521 Heron Wood Pl, Winter Park, FL

Ronald Trotter · RE/MAX INNOVATION

24Active

$2,500/mo

3 bd · 3 ba · 1,397 sqft

3328 Hamlet Loop, Winter Park, FL

Marileen Nieves · LPT REALTY, LLC

7Active

$6,000/mo

3 bd · 3 ba · 1,411 sqft

860 N Denning Dr, Winter Park, FL

LaDarrius Sanders · OUTLET REALTY

8Active

$1,600/mo

2 bd · 1 ba · 881 sqft

1695 Lee Rd #E213, Winter Park, FL

Mirna Perez · LOKATION

37Active

$2,650/mo

4 bd · 2 ba · 1,598 sqft

5600 Revelwood Loop, Winter Park, FL

Max Leo Donzi · IRM INVEST., REAL EST.& MGMT.

Price Reduced20Active

$1,495/mo

2 bd · 2 ba · 1,084 sqft

1111 Washington Ave #3, Winter Park, FL

Amy Spano · WILSON MANAGEMENT GROUP

24Active

$4,500/mo

3 bd · 2 ba · 1,948 sqft

2712 Goldenrod Dr, Winter Park, FL

Ryan Langley · FLORIDA REALTY INVESTMENTS

16Active

$2,240/mo

3 bd · 2 ba · 1,600 sqft

1666 Tremont Ln, Winter Park, FL

David Drawdy, Jr. · KELLER WILLIAMS REALTY AT THE PARKS

10Active

$2,500/mo

5 bd · 3 ba · 2,472 sqft

2612 Roxbury Rd, Winter Park, FL

Susan Lattimore · HOMEPRIDE PROPERTY MANAGEMENT GROUP LLC

16Active

$2,000/mo

2 bd · 1 ba · 1,100 sqft

1824 Howell Branch Rd, Winter Park, FL

Asher Chen · AAA GLOBAL VENTURES PA

15Active

$1,600/mo

2 bd · 1 ba · 881 sqft

1695 Lee Rd #E103, Winter Park, FL

Jason Price · RE/MAX SELECT GROUP

34Active

$3,600/mo

3 bd · 3 ba · 1,753 sqft

1415 Harmon Ave, Winter Park, FL

Lukasz Sokolowski · HOST MANAGEMENT GROUP LLC

12Active

$1,099/mo

1 bd · 1 ba · 645 sqft

2500 Lee Rd #145, Winter Park, FL

Jason Hamilton · THE REALTY MEDICS

8Active

$1,750/mo

2 bd · 1 ba · 1,100 sqft

300 N Knowles Ave 214, Winter Park, FL

Robert Bush · Property Professionals, Inc.

8Active

$1,585/mo

2 bd · 3 ba · 1,031 sqft

7444 Woodburn Ct #29, Winter Park, FL

Abranette Lopez · LPT REALTY, LLC

1 2…4

Listing data & MLS disclosures

MIAMI REALTORS MLS: The multiple listing information is provided by MIAMI Association of Realtors® from a copyrighted compilation of listings. The compilation of listings and each individual listingare ©2026 MIAMI Association of Realtors®. All Rights Reserved.
The information provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Last Updated: 2026-10-06 04:01:36 UTC
Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Winter Park, FL community profile

Population: 31,855
Median income: $98,252
Housing units: 15,404
People per sq. mi.: 1,409.5
Area: 22.6 sq. mi.

Source: HJN community data

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Listing data & MLS disclosures

MIAMI REALTORS MLS: The multiple listing information is provided by MIAMI Association of Realtors® from a copyrighted compilation of listings. The compilation of listings and each individual listingare ©2026 MIAMI Association of Realtors®. All Rights Reserved.
The information provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Last Updated: 2026-10-06 04:01:36 UTC
Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Winter Park, FL community profile

Population: 31,855
Median income: $98,252
Housing units: 15,404
People per sq. mi.: 1,409.5
Area: 22.6 sq. mi.

Source: HJN community data

Apartments and Houses for Rent in Winter Park, FL | Realty.com