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$4,500
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4 Bedroom Apartments Available NowBrightly Renovated 4-Bed / 2-Bath • 1,800 sq
86 Orchard StMedford, MA 02155
4 Bedroom Apartments for Rent in Winchester, MA (49 Rentals)
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$4,000
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4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$4,000
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$4,000
300 Boston Ave, Unit 2F
300 Boston AveMedford, MA 02155
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$4,000
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4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$4,000
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$4,000
300 Boston Ave, Unit 2
300 Boston AveMedford, MA 02155
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$4,000
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4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$4,000
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$4,000
300 Boston Ave, Unit 2
300 Boston AveMedford, MA 02155
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$4,000
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4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$4,000
Total Monthly Price
$4,000
14 Fairmount St, Unit #1
14 Fairmount StMedford, MA 02155
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$4,800
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4 Bedroom Apartment Available Jan 1, 2026Total Monthly Price
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$4,800
Total Monthly Price
$4,800
112 College Ave, Unit 2T
112 College AveMedford, MA 02155
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$4,000
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4 Bedroom Apartment Available Jan 1, 2026Total Monthly Price
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$4,000
Total Monthly Price
$4,000
10 Pinkham Rd, Unit 2T
10 Pinkham RdMedford, MA 02155
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$4,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$4,400
Total Monthly Price
$4,400
100 W Adams St, Unit 100
100 W Adams StSomerville, MA 02144
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$4,200
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,200
Total Monthly Price
$4,200
62 Woods Ave, Unit 2T
62 Woods AveSomerville, MA 02144
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$4,600
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$4,600
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$4,600
288 Boston Ave, Unit 3
288 Boston AveMedford, MA 02155
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$4,600
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4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$4,600
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$4,600
288 Boston Ave, Unit 3
288 Boston AveMedford, MA 02155
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$4,800
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4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$4,800
Total Monthly Price
$4,800
288 Boston Ave, Unit 3
288 Boston AveMedford, MA 02155
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$4,200
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4 Bedroom Apartment Available Jan 1, 2026Total Monthly Price
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$4,200
Total Monthly Price
$4,200
62 Woods Ave, Unit 2
62 Woods AveSomerville, MA 02144
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$4,200
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,200
Total Monthly Price
$4,200
62 Woods Ave, Unit 2A
62 Woods AveSomerville, MA 02144
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$4,500
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,500
Total Monthly Price
$4,500
14 Quincy St
14 Quincy StMedford, MA 02155
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$8,000
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4 Bedroom Apartment Available NowTotal Monthly Price
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$8,000
Total Monthly Price
$8,000
19 Shirley Rd, Unit 19
19 Shirley RdMedford, MA 02155
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$4,200
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4 Bedroom Apartment Available Jan 1, 2026Total Monthly Price
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$4,200
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$4,200
62 Woods Ave, Unit 2
62 Woods AveSomerville, MA 02144
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$4,650
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$4,650
Total Monthly Price
$4,650
30 Adams St, Unit 1
30 Adams StMedford, MA 02155
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$5,650
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$5,650
Total Monthly Price
$5,650
86 Quincy St, Unit 2
86 Quincy StMedford, MA 02155
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$4,800
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,800
Total Monthly Price
$4,800
67 Greenleaf Ave, Unit 1
67 Greenleaf AveMedford, MA 02155
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$4,600
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,600
Total Monthly Price
$4,600
82 Quincy St, Unit #2
82 Quincy StMedford, MA 02155
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$4,600
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,600
Total Monthly Price
$4,600
50 Curtis Ave, Unit 1
50 Curtis AveSomerville, MA 02144
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$4,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$4,400
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$4,400
100 W Adams St, Unit 2
100 W Adams StSomerville, MA 02144
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$4,500
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$4,500
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$4,500
1 Victoria St, Unit 2
1 Victoria StSomerville, MA 02144
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$4,000
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$4,000
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$4,000
10 Pinkham Rd, Unit 2
10 Pinkham RdMedford, MA 02155
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$4,000
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$4,000
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$4,000
10 Pinkham Rd, Unit 2
10 Pinkham RdMedford, MA 02155
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$4,000
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$4,000
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$4,000
10 Pinkham Rd, Unit 2
10 Pinkham RdMedford, MA 02155
Explore Like a Local: The Insider's Guide to Boston
Explore Boston like a local with our guide to neighborhoods, history, and hidden gems. Discover the city's best apartments, from historic brownstones to modern high-rises, and find your perfect Boston home.
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$4,650
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,650
Total Monthly Price
$4,650
299 Alewife Brook Pky, Unit 2
299 Alewife Brook PkySomerville, MA 02144
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$4,600
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,600
Total Monthly Price
$4,600
14 Barton St, Unit 2
14 Barton StSomerville, MA 02144
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$4,650
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,650
Total Monthly Price
$4,650
299 Alewife Brook Pky, Unit 2
299 Alewife Brook PkySomerville, MA 02144
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$4,400
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4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$4,400
Total Monthly Price
$4,400
30 Adams St, Unit 1
30 Adams StMedford, MA 02155
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$4,900
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4 Bedroom Apartment Available NowTotal Monthly Price
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$4,900
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$4,900
1 Victoria St, Unit 2
1 Victoria StSomerville, MA 02144
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$5,000
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4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$5,000
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$5,000
104 W Adams St, Unit 2
104 W Adams StSomerville, MA 02144
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$4,800
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4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
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$4,800
Total Monthly Price
$4,800
12 Pinkham Rd, Unit 1
12 Pinkham RdMedford, MA 02155
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$3,900
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$3,900
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$3,900
56 Gordon St, Unit 1
56 Gordon StSomerville, MA 02144
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$3,300
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4 Bedroom Apartment Available NowTotal Monthly Price
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$3,300
Total Monthly Price
$3,300
167 Sharon St
167 Sharon StMedford, MA 02155
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
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$3,800
Plus Fees
4 Bedroom Apartments Available Now26-28-28 Howard St
26-28-28 Howard StArlington, MA 02476
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$4,000
Plus Fees
4 Bedroom Apartments Available Jun 1, 202614.5 Fairmount St
14.5 Fairmount StMedford, MA 02155
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$4,600
Plus Fees
4 Bedroom Apartments Available Jun 1, 2026288 Boston Ave
288 Boston AveMedford, MA 02155
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$4,400
Plus Fees
4 Bedroom Apartments Available Jun 1, 202656 Gordon St
56 Gordon StSomerville, MA 02144
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$5,600
Plus Fees
4 Bedroom Apartments Available Jun 1, 202650 Upland Rd
50 Upland RdSomerville, MA 02144
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$3,700
Plus Fees
4 Bedroom Apartments Available Jun 1, 2026248 Powder House Blvd
248 Powder House BlvdSomerville, MA 02144
28 Howard St
ArlingtonMA02476
28 Sunset Rd
SomervilleMA02144
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Showing Results 1-49, Page 1 of 1
Winchester, MA Local Guide
Downtown Winchester, Massachusetts by Moonshine4711 is licensed under CC BY-SA 3.0
How much does it cost to rent an apartment in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Studio Apartments | $2,108 | $1,500 | $2,890 |
| Winchester 1 Bedroom Apartments | $2,643 | $1,750 | $4,195 |
| Winchester 2 Bedroom Apartments | $3,205 | $1,350 | $5,500 |
| Winchester 3 Bedroom Apartments | $3,663 | $2,300 | $6,900 |
| Winchester 4 Bedroom Apartments | $4,497 | $3,300 | $8,000 |
| Winchester 5 Bedroom Apartments | $6,263 | $4,500 | $9,300 |
| Winchester 6 Bedroom Apartments | $7,254 | $5,945 | $8,437 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Apartments in Winchester
See all Apartments in WinchesterExplore Winchester
Winchester, MA Local Guide
- Winchester Neighborhoods
- Nearby Cities
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Largest Available Winchester and Nearby 4 Bedroom Apartments
| Apartment Listing | Model Name | Square Footage | Priced From |
|---|---|---|---|
| Brightly Renovated 4-Bed / 2-Bath • 1,800 sq | 86 Orchard | 1,800 Sq Ft | $4,500 |
Cheapest Available Winchester and Nearby 4 Bedroom Apartments
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| Brightly Renovated 4-Bed / 2-Bath • 1,800 sq | 86 Orchard | $4,500 |
Boston Neighborhood Guide: Living Near UMass, MGH, and State Street
Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.
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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 ArticleTop Neighborhoods Near Boston Colleges and Universities
Learn About the Best Neighborhoods to Rent Near College Campuses in Boston, MA | Find Boston Off-Campus Student Housing at ApartmentHomeLiving.com
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Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Winchester, MA Rentals by Map
See the most popular apartments and homes in Winchester, MA
Getting Around Winchester, MA
Walk Score®
71 / 100
Very Walkable
Most errands can be accomplished on foot
Bike Score®
67 / 100
Bikeable
Some bike infrastructure
Transit Score®
1 / 100
Minimal Transit
It may be possible to get on a bus
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
Frequently Asked Questions about Winchester
How much are Studio apartments in Winchester?
There are currently 106 Studio Apartments in Winchester with rent ranges from $1,500 to $2,890 with an average price of $2,108.
What is the current price range for One Bedroom Winchester Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Winchester ranges from $1,750 to $4,195 with an average monthly rent of $2,643.
What does renting a Two Bedroom Apartment in Winchester cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $1,350 to $5,500. Today's average rental price for Two Bedrooms here is $3,205.
How expensive are Winchester Three Bedroom Apartments?
There are currently 130 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,300 to $6,900 - averaging $3,663 for the location.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.
The 10 Best Affordable Neighborhoods in Boston, MA
Written by: Amelia Ramstead
Boston is known for its exciting combination of early American history and modern high-tech universities and employers.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.