Rentals Under $4,000/mo in Windermere, FL

Rentals Under $4,000/mo for Rent in Windermere, FL

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24 of 53 Listings

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Rentals Under $4,000/mo for Rent in Windermere, FL

24 of 53 Listings

New31

53 listings

Rentals Under $4,000/mo for Rent in Windermere, FL

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24 of 53 Listings

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Rentals Under $4,000/mo for Rent in Windermere, FL

24 of 53 Listings

New31

Active

$2,700/mo

3 bd · 3 ba · 1,680 sqft

7751 Fairgrove Ave, Windermere, FL

Katie Drewry · WATSON REALTY CORP

New27Active

$2,250/mo

3 bd · 2 ba · 1,332 sqft

11446 Jasper Kay Ter #1025, Windermere, FL

Jesus Flores · REEURBAN REAL ESTATE SERVICES

22Active

$2,755/mo

3 bd · 3 ba · 1,912 sqft

13796 Beckman Dr, Windermere, FL

Jobe Peterson · THE LISTING REAL ESTATE MANAGEMENT

19Active

$3,250/mo

3 bd · 3 ba · 2,249 sqft

6933 Northwich Dr, Windermere, FL

Nelson Soto Freire · WEST ORLANDO PROPERTY MANAGEMENT REALTY, LLC

22Active

$3,100/mo

4 bd · 3 ba · 2,871 sqft

4760 Blue Major Dr, Windermere, FL

Lisa Ingram · INGRAM REALTY SERVICES LLC

24Active

$3,500/mo

4 bd · 3 ba · 2,214 sqft

11543 Charnock Dr, Windermere, FL

Angela Mavarez Suarez · PM ELITE REALTY LLC

22Active

$2,650/mo

3 bd · 3 ba · 1,556 sqft

8855 Herencia Aly, Windermere, FL

Ramon Morales · SANCTUM REALTY PROFESSIONALS LLC

36Active

$3,100/mo

4 bd · 3 ba · 2,221 sqft

7867 Berkshire Oak Aly, Windermere, FL

Amanda Yuan · MULTI CHOICE REALTY LLC

33Active

$2,900/mo

3 bd · 3 ba · 2,091 sqft

13701 Beckman Dr, Windermere, FL

Lukasz Sokolowski · HOST MANAGEMENT GROUP LLC

27Active

$2,650/mo

3 bd · 3 ba · 1,748 sqft

7651 Fordson Ln, Windermere, FL

Elizabeth Ferreira Figueira · LA ROSA REALTY PREMIER LLC

Price Reduced31Active

$2,800/mo

3 bd · 3 ba · 1,891 sqft

8615 Via Trieste Dr, Windermere, FL

Orlando Calderon · PREMIER CHOICE REALTY & MANAGEMENT LLC

54Active

$3,300/mo

3 bd · 3 ba · 1,977 sqft

6310 Golden Dewdrop Trl, Windermere, FL

Ane Bertol Bertol · AXEN REALTY, LLC

12Active

$4,000/mo

3 bd · 3 ba · 1,984 sqft

6436 Golden Dewdrop Trl, Windermere, FL

Gittel Leibowitz · PREFERRED REAL ESTATE BROKERS

Price Reduced17Active

$2,850/mo

4 bd · 3 ba · 1,866 sqft

7668 Fairgrove Ave, Windermere, FL

Andrea Munoz · VESTI LLC

29Active

$2,400/mo

3 bd · 3 ba · 1,363 sqft

8259 Maritime Flag St #7, Windermere, FL

Alfredo Meyer · ALTIS REALTY

23Active

$2,550/mo

3 bd · 2 ba · 1,332 sqft

8256 Maritime Flag St #305, Windermere, FL

Melody Niederst · IAD REAL ESTATE

Price Reduced41Active

$2,650/mo

3 bd · 3 ba · 1,580 sqft

8428 Iron Mountain Trl, Windermere, FL

Lidya Gongage · SPRING REALTY ORLANDO

29Active

$3,750/mo

4 bd · 4 ba · 2,682 sqft

13633 Riggs Way, Windermere, FL

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

Price Reduced15Active

$2,799/mo

4 bd · 2 ba · 2,074 sqft

12986 Holdenbury Ln, Windermere, FL

Nancy Guadagnino · SPECIALIZED PROPERTY MANAGEMENT

32Active

$2,750/mo

3 bd · 3 ba · 1,588 sqft

7243 Shadeview Aly, Windermere, FL

Claudia Panella · COLDWELL BANKER REALTY

28Active

$3,150/mo

4 bd · 4 ba · 2,469 sqft

13314 Roxboro Rd, Windermere, FL

Charles Woolley · BHHS FLORIDA REALTY

37Active

$2,475/mo

3 bd · 3 ba · 1,429 sqft

Address withheld · Windermere, FL

Aziz Elbrak · LA ROSA REALTY LLC

38Active

$2,800/mo

2 bd · 1 ba · 950 sqft

7612 Ficquette Rd, Windermere, FL

Elsie Benitez, PA · BENITEZ ROYAL REALTY LLC

12Active

$2,300/mo

2 bd · 3 ba · 1,311 sqft

12543 Cruxbury Dr, Windermere, FL

Caroline Perotti · BELLA VIEW REALTY LLC

Listing data & MLS disclosures

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.

Windermere, FL community profile

Population: 3,301
Median income: $148,077
Housing units: 1,328
People per sq. mi.: 115
Area: 28.7 sq. mi.

Source: HJN community data

Explore Windermere rentals

Listing data & MLS disclosures

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.

Windermere, FL community profile

Population: 3,301
Median income: $148,077
Housing units: 1,328
People per sq. mi.: 115
Area: 28.7 sq. mi.

Source: HJN community data

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Listing data & MLS disclosures

Windermere, FL community profile

Explore Windermere rentals

Listing data & MLS disclosures

Windermere, FL community profile