
Cheap Homes for Rent in the Upper Madison Neighborhood of Bridgeport, CT from $1,100 (28 Rentals)
Search the lowest-cost Homes available for rent right now in the Upper Madison area of Bridgeport.


1428 North Ave

1511 Pembroke St, Unit 6

46 Anton Dr, Unit Basement

1333 E Main St

186 Louisiana Ave

45 Stevens St, Unit 1-3
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.

2600 Park Ave

2625 Park Ave

45-45 Jackson Ave

333 Vincelette St

183 Livingston Pl

128 Robert St

70 Lindley St, Unit 3rd Floor
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

70 Lindley St, Unit 2nd Floor

98 Sanford Ave, Unit 2nd floor

3000 Madison Ave

3250 Main St

99 William St

18 Amsterdam Ave

120 Huntington Turnpike
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

136 McKinley Ave

116 Ogden St

980 Lindley St

85 Madison Ave

127 Kennedy Dr

715 Frenchtown Rd

240 Madison Ave, Unit 1
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
Upper Madison, Bridgeport, CT Local Guide

How much does it cost to rent a home in Upper Madison?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Upper Madison 2 Bedroom Homes for Rent | $2,457 | $1,650 | $3,700 |
| Upper Madison 3 Bedroom Homes for Rent | $3,714 | $1,950 | $6,500 |
| Upper Madison 4 Bedroom Homes for Rent | $3,776 | $2,200 | $5,600 |
| Upper Madison 5 Bedroom Homes for Rent | $4,670 | $3,700 | $7,500 |
| Upper Madison 7 Bedroom Homes for Rent | $6,500 | $6,500 | $6,500 |
Browse Homes for Rent in this Neighborhood
There are currently 28 rentals with your search options within a 2 mile radius of the Upper Madison Neighborhood of Bridgeport, CT.
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Upper Madison, Bridgeport, CT Local Guide
- Nearby Bridgeport neighborhoods
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Cheapest Available Upper Madison Apartments for Rent
 The cheapest available apartment rental in the Upper Madison area of Bridgeport, CT is a Studio unit found at G Wells LLC priced from $1,100. Pembroke Commons has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,396. Here are the most affordable Upper Madison apartments for rent in Bridgeport, CT:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| G Wells LLC | Studio | Studio,1BA | $1,100 |
| Pembroke Commons | 1 bedroom | 1BR,1BA | $1,396 |
| Brookside Gardens | Renovated Studio | Studio,1BA | $1,610 |
| Lynn Apartments | Renovated Studio | Goldenrod | Studio,1BA | $1,890 |
| The Royce at Trumbull | The Dover | 1BR,1BA | $1,929 |
| The Residences at Main | $3.09/sq.ft. - A-02 | 1BR,1BA | $2,245 |
| Woodside Trumbull | A1 | 1BR,1BA | $2,379 |
Best Value Apartments for Rent in Upper Madison, CT
As of July 12, 2026 the best value apartment in the Upper Madison area is the $1.36 price per square foot 1520 Pembroke St Model at 1520 Pembroke St, Unit 1L in the in the Lower Long Hill neighborhood starting from $2,450. The second greatest value Upper Madison apartment is the 245 jane st Model at 245 jane st starting at $2,400 with a $2.00 price per square foot in the North End neighborhood. Here is today’s list of the best values for Upper Madison apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 1520 Pembroke St, Unit 1L | 1520 Pembroke St | 5BR,1BA | $1.36 |
| 245 jane st | 245 jane st | 3BR,1BA | $2.00 |
| 13 Armstrong Pl, Unit Apt 2 | 13 Armstrong Pl | 3BR,1BA | $1.62 |
| 26 Arlington St, Unit 2 | 26 Arlington St | 2BR,1BA | $1.79 |
| 1511 Pembroke St, Unit 1 | 1511 Pembroke St | 1BR,1BA | $1.44 |
| Ten Trumbull | Fillmore | 1BR,1BA | $3.10 |
| The Residences at Main | $3.24/sq.ft. - A-01 | 1BR,1BA | $3.06 |
| Woodside Trumbull | A1 | 1BR,1BA | $3.08 |
| The Royce at Trumbull | The Dover | 1BR,1BA | $2.71 |
| Pembroke Commons | 1 bedroom | 1BR,1BA | $1.99 |
Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
Read ArticleReal Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
Read ArticleQuick Rent Budget Calculator
How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
Pet Friendly LifestyleUpper Madison, Bridgeport, CT
Ranked #6
Among cities in Connecticut for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
4.0Pet Friendly
Frequently Asked Questions about Upper Madison
What type of rentals are currently available in Upper Madison?
There are currently 261 Apartments for Rent in Upper Madison, CT with pricing that ranges from $1,300 to $4,482. There are also 83 Single Family Homes for rent, Condos, and Townhome rentals currently available in Upper Madison ranging from $1,150 to $7,500.
What is the current price range for Rental Homes in Upper Madison?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Upper Madison ranges from $1,150 to $7,500 with an average monthly rent of $3,438.
How much are larger Three and Four Bedroom Rentals in Upper Madison?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Upper Madison range from $1,700 to $4,482, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,950 to $6,500. Four Bedroom Single-Family rentals are also available starting from $2,200 and Four Bedroom Apartments start at $2,375.
Expert Rental Resources
The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.
Articles, How-To's, and Tips

Local Expert's Guide to the Top Affordable Neighborhoods for Renting in Bridgeport, CT
Written by: M. April Tome
I'm April, your ApartmentHomeLiving.com Local Expert for Bridgeport, CT. I have lived in Fairfield County for over thirty years. I decided to downsize and move to a city with more amenities and affordable rental options.

Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.