
Cheap Homes for Rent in Upper Madison Neighborhood of Bridgeport, CT from $1,100 (59 Rentals)
Search the lowest-cost Homes available for rent right now in the Upper Madison area of Bridgeport.


240 Oak St

240 Oak St

240 Oak St

240 Oak St

105 A Williams St

240 Oak St

190 Birdseye St

1350 Brooklawn Ave

155 Birdseye St
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.

155 Birdseye St

3245 Main St

285 Waterview Ave

748 Arctic St

1057 E Main St

625 Cleveland Ave

191 Oak St

2068 Main St

74 Garfield Ave

2014 Main St
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.

335 Wells St

1795 North Ave

240 William St

595 William St

191 Oak St

159 Charles St

165 McKinley Ave

957 William St

64 McKinley Ave, Unit a9

65 James St, Unit 3rd floor
Local Expert's Guide to the Top Affordable Neighborhoods for Renting in Bridgeport, CT
Learn about Bridgeport and the best neighorhoods to rent with original content written by our Local Expert Staff Writer

1057 E Main St

666 Ogden St

666 Ogden St

708 Hallett St

508 Pequonnock St

1368 E Main St

657 Maple St

2600 Park Ave

3200 Madison Ave

2336 Main St
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

595 William St

2066 Main St

38 Enid St

1220 Pembroke St

87 Caroline St

87 Caroline St

183 Livingston Pl

128 Robert St

335 Wells St

4666 Main St
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.
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 | $2,164 | $1,700 | $3,750 |
| Upper Madison 3 Bedroom Homes for Rent | $2,837 | $1,950 | $4,700 |
| Upper Madison 4 Bedroom Homes for Rent | $3,871 | $1,850 | $6,500 |
| Upper Madison 5 Bedroom Homes for Rent | $9,187 | $4,250 | $10,000+ |
| Upper Madison 7 Bedroom Homes for Rent | $6,500 | $6,500 | $6,500 |
Browse Homes for Rent in this Neighborhood
There are currently 59 rentals with your search options within a 2 mile radius of the Upper Madison Neighborhood of Bridgeport, CT.
Explore Bridgeport
Upper Madison, Bridgeport, CT Local Guide
- Nearby Bridgeport neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Cheapest Available Upper Madison Apartments for Rent
 The cheapest available apartment rental in the Upper Madison area of Bridgeport, CT is a 1 Bed unit found at Pembroke Commons priced from $1,396. Lynn Apartments has the second lowest priced unit, which is a Studio apartment currently listed from $1,510. Here are the most affordable Upper Madison apartments for rent in Bridgeport, CT:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Pembroke Commons | 1 bedroom | 1BR,1BA | $1,396 |
| Lynn Apartments | Unrenovated Studio - Goldenrod | Studio,1BA | $1,510 |
| Brookside Gardens | Studio | Studio,1BA | $1,610 |
Best Value Apartments for Rent in Upper Madison, CT
As of February 26, 2026 the best value apartment in the Upper Madison area is the $1.33 price per square foot 2436 E Main St Model at 2436 E Main St, Unit 2436 E Main Street in the in the Lower Long Hill neighborhood starting from $2,000. The second greatest value Upper Madison apartment is the 55 Eaton St Model at 55 Eaton St, Unit 55 Eaton Street 2nd floor starting at $1,900 with a $1.42 price per square foot in the Enterprise Zone 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. |
|---|---|---|---|
| 2436 E Main St, Unit 2436 E Main Street | 2436 E Main St | 2BR,1BA | $1.33 |
| 55 Eaton St, Unit 55 Eaton Street 2nd floor | 55 Eaton St | 2BR,1BA | $1.42 |
| 245 jane st | 245 jane st | 3BR,1BA | $2.00 |
| 123 Platt St | 123 Platt St | 3BR,1BA | $2.05 |
| 1518 Pembroke St, Unit 2L | 1518 Pembroke St | 3BR,1BA | $2.00 |
| The Residences at Main | $2.83/sq.ft. - A-03 | 1BR,1BA | $2.83 |
| The Royce at Trumbull | The Ash | 1BR,1BA | $2.73 |
| 862 Wood Ave, Unit Unit 8 | 862 Wood Ave | 1BR,1BA | $2.09 |
| Pembroke Commons | 1 bedroom | 1BR,1BA | $1.99 |
| 255 Fairfield Woods Rd, Unit 2 | 255 Fairfield Woods Rd | 1BR,1BA | $2.88 |
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 ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleCash 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.
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 #21
Among cities in Connecticut for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.5Pet Friendly
Frequently Asked Questions about Upper Madison
What type of rentals are currently available in Upper Madison?
There are currently 294 Apartments for Rent in Upper Madison, CT with pricing that ranges from $975 to $24,927. There are also 134 Single Family Homes for rent, Condos, and Townhome rentals currently available in Upper Madison ranging from $1,100 to $23,000.
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 $1,100 to $23,000 with an average monthly rent of $3,902.
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 $1,995 to $4,965, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,950 to $4,700. Four Bedroom Single-Family rentals are also available starting from $1,850 and Four Bedroom Apartments start at $1,850.
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 Experts 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.

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.