Milton Coste

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NYC Neighborhood Comparison

Midtown South vs Windsor Terrace

Side-by-side market data, transit, and neighborhood profiles to help you decide.

Manhattan|Brooklyn

Midtown South

Manhattan

Windsor Terrace

Brooklyn

How They Compare

For buyers focused on affordability, Windsor Terrace has the lower median sale price at $825K vs $850K in Midtown South.

Investors analyzing rental yield will find Midtown South offers a stronger rent-to-price ratio based on current market data.

Commuters have more transit options in Midtown South, which is served by 16 subway lines compared to 0 in Windsor Terrace.

Median Sale Price
$850K
$825K
Median Rent
$5K
$4K
Active Listings
69
41
Avg Days on Market
48 days
31.5 days
YoY Price Change
+0.2%
-54.8%
Monthly Sales Volume
4
11

Detailed Comparison

MetricMidtown SouthWindsor Terrace
Median Sale Price$850,000$825,000
Median Condo Price$2,760,000N/A
Median Co-op Price$610,000$837,250
Median Rent$5,100$3,897.5
Active Listings6941
Rental Inventory20866
Days on Market4831.5
Price Cut Share8.7%4.9%
Monthly Sales Volume411
YoY Price Change+0.2%-54.8%
YoY Rent Change+5.2%+2.6%
YoY Inventory Change+4.5%-18.0%
Subway Lines1 2 3 7 A B C D E F M N Q R S WN/A

Year-Over-Year Price Movement

Prices in Midtown South moved +0.2% over the past year, compared to -54.8% in Windsor Terrace. Midtown South is seeing price appreciation while Windsor Terrace has softened, pointing to different supply-demand dynamics in each market.

Neighborhood Profiles

Midtown South

Midtown South encompasses the blocks around the Flatiron Building and Madison Square Park, featuring converted loft-style condos, Beaux-Arts co-ops, and Art Deco apartment buildings alongside new residential towers. The R and W trains at 23rd Street, the 6 train on Park Avenue South, and the F and M trains on Sixth Avenue provide extensive subway coverage.

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Windsor Terrace

Windsor Terrace borders Prospect Park on three sides and Green-Wood Cemetery to the west, creating a compact residential neighborhood of brick and limestone rowhouses, Victorian-era wood-frame homes, and prewar apartment buildings along Prospect Avenue, Seeley Street, and Vanderbilt Street. The F and G trains stop at 15th Street-Prospect Park and Fort Hamilton Parkway, providing connections to Downtown Brooklyn and Manhattan. Prospect Park's Parade Ground, the city's oldest recreational facility, sits at the neighborhood's southeastern edge.

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Transit Access

Midtown South

1237ABCDEFMNQRSW

34 St-Penn Station (1 2 3 A C E) — 0.3 mi

34 St-Herald Sq (B D F M N Q R W) — 0.5 mi

42 St-Port Authority (A C E) — 0.7 mi

Times Sq-42 St (1 2 3 7 N Q R S W) — 0.7 mi

Windsor Terrace

No subway data available

Active Listings

Midtown South for sale

View all Midtown South listings

Windsor Terrace for sale

View all Windsor Terrace listings

Listing data is derived in whole or in part from the RLS at REBNY (Real Estate Board of New York) Internet Data Exchange (IDX) database. Real estate listings held by brokerage firms other than Milton Coste | Keller Williams NYC are marked with the RLS logo. The information provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is refreshed every 15 minutes per REBNY IDX requirements.

Midtown South vs Windsor Terrace: Home Price Resilience 2008-2020

From the 2008 financial crisis through the 2020 pandemic, the NYC metro Case-Shiller composite fell about 25% peak-to-trough between 2007 and 2012, then fully recovered by 2017 and gained another 15% through Q1 2020. Midtown South and Windsor Terrace both tracked this broader NYC arc, with annual closing volume contracting sharply in 2009 and again in Q2 2020 before normalizing.

Midtown South tracked the more resilient Manhattan price path with a 10% to 15% peak-to-trough decline, while Windsor Terrace moved closer to the broader NYC metro pattern of a 20% to 25% retracement before recovering through 2017.

Source: Per Case-Shiller Home Price Index, NYC metro subset, 2008-2020, cross-referenced with StreetEasy historical price data series.

Metric (2026)Midtown SouthWindsor Terrace
Median Sale Price$850,000$825,000
Median Rent$5,100/mo$3,897.5/mo
Year-over-Year Price Change+0.2%-54.8%
Average Days on Market48 days31.5 days
Distance to Nearest Subway0.33 miN/A

Table values reflect current 2026 market conditions. Historical 2008-2020 commentary is sourced from Case-Shiller NYC metro composite and StreetEasy historical series.

Frequently Asked Questions

Is Midtown South cheaper than Windsor Terrace?
Windsor Terrace is more affordable, with a median sale price of $825,000 vs $850,000 in Midtown South. Pricing can vary widely by building, floor, and unit condition, so review current listings for accurate comparisons.
Which has better transit, Midtown South or Windsor Terrace?
Midtown South has access to 16 subway lines and Windsor Terrace has 0, making Midtown South the stronger option for transit access. Windsor Terrace has 0 lines, which may still cover your commute depending on your destination.
Which is better for families, Midtown South or Windsor Terrace?
This depends on what type of home fits your household. Midtown South and Windsor Terrace both offer a mix of apartment and multi-room units in co-ops, condos, and townhouses. Larger 3- and 4-bedroom units, including townhouses and multi-family properties, tend to be more available in lower-density areas. Reviewing active listings filtered by bedroom count is the most reliable way to see what each neighborhood currently offers for larger households. A licensed broker can pull current inventory by bedroom count across both areas for a direct comparison.
Should I buy in Midtown South or Windsor Terrace?
The right neighborhood depends on your price range, commute needs, and preferred property type. A comparative market analysis (CMA) of recent sales in both Midtown South and Windsor Terrace gives you the clearest picture of what your budget gets in each location. Request a free CMA from Milton Coste to get a side-by-side breakdown of current opportunities.

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Need Help Choosing?

With 25+ years of experience across all five boroughs, I can help you find the right neighborhood for your lifestyle and budget.

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