Aerial view of homes in the Windsor Hills neighborhood, Tallahassee, FL

Windsor Hills · Northeast Tallahassee

Windsor Hills Homes for Sale

Last updated: November 8, 2026

Windsor Hills is a neighborhood of 64 single-family homes in Northeast Tallahassee. Homes here were built from 1960 through 2020.

Windsor Hills market intelligence

Windsor Hills Homes for Sale

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At a glance

Windsor Hills Key Facts

  • Location: Northeast Tallahassee
  • ZIP Code: 32308
  • Homes: 64 single-family homes
  • Construction Era: From 1960 through 2020; median year built 1960
  • Median home size: 1,217 square feet
  • Most common layout: 3 bedrooms, 1 bathroom
  • HOA: No HOA
  • Owner-Occupied: 44% owner occupied
  • Elementary school: Sullivan Elementary, 0.9 miles, Florida DOE school grade B (2026), (850) 487-1216
  • Middle school: Cobb Middle, 1.1 miles, Florida DOE school grade A (2026), (850) 488-3364
  • High school: Leon High, 1.5 miles, Florida DOE school grade B (2026), (850) 617-5700
  • Median lot size: 0.23 acres

Property and Neighborhood Explorer

Windsor Hills Boundary and Lots

The map below outlines the Windsor Hills boundary and every lot inside it. A click on any lot shows its last sale, and the search box finds a home by address.

Zoom in and click any lot for its details.

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Neighborhoods Near Windsor Hills

Every Tallahassee neighborhood we cover is in the neighborhood directory, so you can line Windsor Hills up against any of them.

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Windsor Hills Homes for Sale

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Windsor Hills Homes: 64 Single-Family Homes

All 64 homes in Windsor Hills are single-family homes, built from 1960 through 2020.

The median home size in Windsor Hills is 1,217 square feet of heated and cooled space. The most common layout here is three bedrooms and one bathroom.

In Windsor Hills, 48% of owners have held their home for ten years or more.

Only 44% of the homes in Windsor Hills are owner occupied, meaning the majority are rented or held as a second home.

Windsor Hills is in ZIP code 32308. The homes here line Buckingham Drive, Marys Drive, Belvedere Street, Canterbury Street, and Sandringham Drive.

Drive Times From Windsor Hills

Downtown & campus
Florida Capitol
about 8 minutes
2.5 miles
Florida State University
about 9 minutes
2.8 miles
Florida A&M University
about 11 minutes
3.5 miles
I-10, Exit 199
about 11 minutes
4.1 miles
Bobby Bowden-Tallahassee International Airport
about 22 minutes
9 miles
Hospitals
The coast
Hospitals
Tallahassee Memorial Hospital
about 2 minutes
0.6 miles
HCA Florida Capital Hospital
about 7 minutes
2.4 miles
The coast
Shields Marina, St. Marks
about 37 minutes
22.6 miles
Carrabelle Marina
about 1 hour 15 minutes
56.6 miles
St. George Island
about 1 hour 45 minutes
78 miles

Where Is the Tallahassee Market Headed?

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Windsor Hills, Northeast Tallahassee

No HOA

Windsor Hills has no homeowners association, and there are no association dues.

Windsor Hills market

Windsor Hills Home Prices and Sales

1Sales closed, past 12 months
64Windsor Hills homes

Sales records for Windsor Hills begin in 1991 and run through November 8, 2026. The figures below leave out family transfers, bank sales, and short sales.

How Much Do Windsor Hills Homes Sell For?

Median price of the homes sold each year in Windsor Hills, existing homes and new construction, with 2026 covering January to November

Medians describe the homes that sold each year, not the value of any one home.

A dot on its own marks a year with sales but no sales the year before or after.

Sources: Tallahassee Board of Realtors Multiple Listing Service and the Leon County Property Appraiser. Sales updated November 8, 2026.

New construction and existing homes are always charted separately, so a year's new-construction figure can come from just one or two sales.

Annual figures
Median sale price, by closing year
YearWindsor Hills existing homesWindsor Hills new constructionLeon County existing homesLeon County new constructionWindsor Hills sales (existing / new)
2026$265,000$305,000$436,9001 / 0
2025$190,000$289,600$419,9001 / 0
2024$212,500$288,500$416,1504 / 0
2023$365,500$270,000$410,7003 / 0
2022$249,900$245,000$415,7501 / 0
2021$211,000$225,000$325,0004 / 0
2020$157,500$215,000$302,1501 / 0
2019$178,850$195,000$279,9004 / 0
2018$141,500$188,000$310,5002 / 0
2017$197,450$185,000$285,4004 / 0
2016$178,400$289,0000 / 0
2015$198,600$178,000$269,8502 / 0
2014$119,350$209,000$176,000$276,1004 / 1
2013$195,000$175,000$282,9001 / 0
2012$93,500$169,000$270,9001 / 0
2011$79,500$167,800$244,6501 / 0
2010$173,500$170,000$192,0001 / 0
2009$168,000$184,5000 / 0
2008$157,250$177,500$202,2502 / 0
2007$172,500$179,600$193,5004 / 0
2006$158,000$176,500$183,5001 / 0
2005$147,750$166,0504 / 0
2004$132,000$149,0003 / 0
2003$93,200$134,9004 / 0
2002$109,900$122,0001 / 0
2001$79,000$115,0003 / 0
2000$80,500$105,0005 / 0
1999$78,000$102,0005 / 0
1998$84,500$99,0001 / 0
1997$109,400$90,0002 / 0
1996$75,000$90,0004 / 0
1995$72,400$85,0002 / 0
1994$88,000$79,0001 / 0
1993$74,000$77,5007 / 0
1992$60,250$73,3006 / 0
1991$58,000$68,5003 / 0
1990$60,000$68,0004 / 0
1989$60,000$63,0003 / 0
1988$52,500$61,8504 / 0
1987$55,000$61,4005 / 0
1986$50,950$59,5004 / 0
1985$50,000$58,9003 / 0
1984$46,700$55,0007 / 0
1983$45,800$54,0004 / 0
1982$50,100$54,5004 / 0
1981$44,250$51,3004 / 0
1980$40,000$47,5005 / 0
1979$33,500$44,5005 / 0
1978$33,100$40,0004 / 0
1977$29,000$37,0006 / 0
1976$29,900$35,5001 / 0
1975$23,500$36,5003 / 0
1974$32,3000 / 0
1973$19,100$28,5002 / 0
1972$20,000$24,3006 / 0

How Much Are Windsor Hills Homes Worth?

Median home value, in price per square foot, each year in Windsor Hills, existing homes and new construction, with 2026 covering January to November

Medians describe the homes that sold each year, not the value of any one Windsor Hills home.

A dot on its own marks a year with sales but no sales the year before or after.

Sources: Tallahassee Board of Realtors Multiple Listing Service and the Leon County Property Appraiser. Sales updated November 8, 2026.

New construction and existing homes are always charted separately, so a year's new-construction figure can come from just one or two sales.

Annual figures
Median price per square foot, by closing year
YearWindsor Hills existing homesWindsor Hills new constructionLeon County existing homesLeon County new constructionWindsor Hills sales (existing / new)
2026$200$199$2361 / 0
2025$145$194$2441 / 0
2024$134$193$2394 / 0
2023$231$186$2313 / 0
2022$205$170$2081 / 0
2021$184$152$1834 / 0
2020$108$137$1731 / 0
2019$137$126$1724 / 0
2018$116$123$1712 / 0
2017$123$117$1644 / 0
2016$113$1550 / 0
2015$94$110$1522 / 0
2014$107$133$107$1474 / 1
2013$121$105$1441 / 0
2012$77$100$1371 / 0
2011$40$102$1301 / 0
2010$108$109$1221 / 0
2009$113$1270 / 0
2008$127$122$1312 / 0
2007$121$129$1384 / 0
2006$130$1361 / 0
20054 / 0
20043 / 0
20034 / 0
20021 / 0
20013 / 0
20005 / 0
19995 / 0
19981 / 0
19972 / 0
19964 / 0
19952 / 0
19941 / 0
19937 / 0
19926 / 0
19913 / 0
19904 / 0
19893 / 0
19884 / 0
19875 / 0
19864 / 0
19853 / 0
19847 / 0
19834 / 0
19824 / 0
19814 / 0
19805 / 0
19795 / 0
19784 / 0
19776 / 0
19761 / 0
19753 / 0
19740 / 0
19732 / 0
19726 / 0

How Big Are the Homes That Sell in Windsor Hills?

Median home size, in square feet, each year in Windsor Hills, existing homes and new construction, with 2026 covering January to November

Medians describe the homes that sold each year, not the value of any one home.

A dot on its own marks a year with sales but no sales the year before or after.

Sources: Tallahassee Board of Realtors Multiple Listing Service and the Leon County Property Appraiser. Sales updated November 8, 2026.

New construction and existing homes are always charted separately, so a year's new-construction figure can come from just one or two sales.

Annual figures
Median size (sq ft), by closing year
YearWindsor Hills existing homesWindsor Hills new constructionLeon County existing homesLeon County new constructionWindsor Hills sales (existing / new)
20261,3271,5661,8731 / 0
20251,3121,5441,7471 / 0
20241,3271,5221,7864 / 0
20231,4091,4881,7913 / 0
20221,2211,4761,9351 / 0
20211,2331,5021,8074 / 0
20201,4651,5811,7571 / 0
20191,2021,5691,6704 / 0
20181,2231,5501,7912 / 0
20171,5491,5941,7444 / 0
20161,6261,8030 / 0
20152,1091,6821,7642 / 0
20141,1521,5711,6961,8764 / 1
20131,6061,7002,0101 / 0
20121,2121,7291,9871 / 0
20111,9921,7031,7831 / 0
20101,6051,6441,5731 / 0
20091,5371,4870 / 0
20081,3011,5041,5702 / 0
20071,3211,4651,5354 / 0
20061,4691,4701 / 0
20054 / 0
20043 / 0
20034 / 0
20021 / 0
20013 / 0
20005 / 0
19995 / 0
19981 / 0
19972 / 0
19964 / 0
19952 / 0
19941 / 0
19937 / 0
19926 / 0
19913 / 0
19904 / 0
19893 / 0
19884 / 0
19875 / 0
19864 / 0
19853 / 0
19847 / 0
19834 / 0
19824 / 0
19814 / 0
19805 / 0
19795 / 0
19784 / 0
19776 / 0
19761 / 0
19753 / 0
19740 / 0
19732 / 0
19726 / 0

Windsor Hills Recent Sales

Recent Windsor Hills home sales
AddressPricePrice / sq ftClosing dateYear builtSq ftSale type
$265,000$2002026-03-0619601,327Existing
$190,000$1452025-05-1619601,312Existing
$177,500$1342024-11-0419601,327Existing
$265,000$2192024-08-0919601,212Existing
$205,0002024-06-251960Existing
$220,000$1212024-01-3019601,819Existing
$365,500$2592023-08-2419601,409Existing
$280,000$2312023-06-1619601,212Existing
$382,000$1802023-05-0319882,120Existing
$249,900$2052022-05-0619601,221Existing
$230,000$1702021-12-0919601,355Existing
$227,000$1842021-07-0919601,233Existing
$195,0002021-04-301960Existing
$165,000$1892021-02-261960874Existing
$157,500$1082020-07-1019601,465Existing
$125,000$1322019-12-161960948Existing
$200,000$1422019-07-2919601,408Existing
$255,000$1202019-07-0119882,120Existing
$157,700$1582019-04-301960996Existing
$140,000$1162018-10-2419601,212Existing
$143,000$1162018-07-0919601,233Existing
$179,500$1272017-10-1619601,408Existing
$194,900$1442017-06-0519601,355Existing
$210,000$1002017-04-2419602,097Existing
$200,000$1182017-03-3119601,689Existing
Showing 25 of 100 sales

Sources: the Leon County Property Appraiser and the MLS.

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Schools

Schools Serving Windsor Hills

2026–27 attendance zones

Assigned Public Schools

All homes in Windsor Hills are zoned for Sullivan Elementary School, Cobb Middle School, and Leon High School.

Sullivan Elementary School is 0.9 miles from Windsor Hills and has a Florida DOE school grade of B (2026). Its phone number is (850) 487-1216.

Cobb Middle School is 1.1 miles away and has a Florida DOE school grade of A (2026). Its phone number is (850) 488-3364.

Leon High School is 1.5 miles away and has a Florida DOE school grade of B (2026). Its phone number is (850) 617-5700.

Sullivan Elementary SchoolFlorida DOE school grade: B (2026)All 64 homes in Windsor Hills
Cobb Middle SchoolFlorida DOE school grade: A (2026)All 64 homes in Windsor Hills
Leon High SchoolFlorida DOE school grade: B (2026)All 64 homes in Windsor Hills

School zones can change from time to time, so check the current assignment for the exact address before you buy.

The Leon County Schools zone lookup shows the assigned schools for any address.

Other Schools Nearby

Charter Schools

These are tuition-free public schools open to students from any Leon County address.

Buying in Windsor Hills

Buying a Home in Windsor Hills

On average, two homes in Windsor Hills come up for sale each year, 3% of the neighborhood, so a buyer who wants to live here has to be ready when one does. Ready means you choose your agent first, build the plan together, and then find the house. Our plan is to negotiate from what the home is worth, not from an inflated asking price. Ask us for the plan before you start looking.

Plan Your Windsor Hills Search

To see every home for sale that fits your search, in Windsor Hills or nearby, use the Home Finder.

If you plan to buy here, the Tallahassee home buying guide lays out the steps in order.

To turn a Windsor Hills price into a monthly payment, use the mortgage calculator.

Selling in Windsor Hills

Selling a Home in Windsor Hills

Most sellers negotiate with one buyer at a time. Our selling plan is built to bring several buyers together so they compete for your home. Ask us how that plan would work when you sell in Windsor Hills.

If you own a home here and plan to sell, the Tallahassee home selling guide covers what to decide before the home goes on the market.

To learn what your Windsor Hills home is worth today, request a home evaluation.

The home marketing plan shows how our selling plan is built to bring several buyers to the same home.

What Is Your Windsor Hills Home Worth Right Now?

Windsor Hills questions

Windsor Hills Frequently Asked Questions

Are new homes still being built in Windsor Hills?

No. The newest home in Windsor Hills was built in 2020, and no vacant lots remain.

What homes have recently sold in Windsor Hills?

The most recent sale in Windsor Hills was 1709 Canterbury St, which sold for $265,000 on March 6, 2026. Before that, 1716 Canterbury St sold for $190,000 on May 16, 2025, and 1709 Canterbury St sold for $177,500 on November 4, 2024. See all 100 recent sales in the table above.

What types of homes are in Windsor Hills?

All 64 homes in Windsor Hills are single-family homes. The median home size is 1,217 square feet of heated and cooled space, and the most common layout is three bedrooms and one bathroom.

What are the HOA dues in Windsor Hills?

Windsor Hills has no homeowners association, and there are no association dues.

Which public schools serve the Windsor Hills neighborhood?

Sullivan Elementary School, Cobb Middle School, and Leon High School. School zones can change from time to time, so confirm the current assignment for the home you choose with your Joe Manausa Team member.

Are homes in Windsor Hills in a flood zone?

No. None of the 64 lots in Windsor Hills are in a FEMA 1%-chance flood zone.

How old are the homes in Windsor Hills?

Homes in Windsor Hills were built from 1960 through 2020. The median year built is 1960, so half the homes are older than 66 years and half are newer.

How should a home in Windsor Hills be valued?

A home in Windsor Hills is best valued against recent sales of similar homes here, adjusted for differences in size, condition, updates and lot. Online estimates can't see inside a home, so for a figure on one home, request a home evaluation from a Joe Manausa Team member.

Questions about one Windsor Hills address

Ready to Talk About a Windsor Hills Property?

This page describes Windsor Hills as a whole, not the one home you have in mind. Bring your questions about that home to a Joe Manausa Team member before you decide.

For local services you may need before or after a move, see our preferred vendor list.

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