21 Pleasant Street, Nantucket, MA 02554

21 Pleasant Street Nantucket MA 02554
Click to view the Official Assessors Field Card Print Report
Owner Information
Owner 1
Jennifer S Gressman
Owner 2
Jennifer S Grossman Living Trust Dated September 26 200
Owner's Address
Pending Verification ,
Market Sale Information
Most recent sale date
3/20/2025
Previous sale date
11/24/2021
Transfer document #
2007-228
Previous transfer document
1865-252
Grantor
21a Pleasant Street LLC
Previous grantor
Geoffrey Thayer
Most recent sale price
$7,375,000.00
Previous sale price
$1,950,000.00
Site Information
Property ID
5541-1
Lot Size
0.11
Use Code
101 - Residential, single family
Zoning
ROH
Building Style
Conventional
Number of Rooms
Stories
2
Number of Beds
3
Year Built
1923
Number of full baths
1
Condition
Number of half baths
2
Finished Area
1936
Number of Kitchen
1
Gross Living Area
3266
Number of Fireplaces
Bsmnt floot
Number of parking
Interior walls
Plastered
Floor type
Hardwood, Carpet
Solar Hot Water
No
Roof Structure
Gable/Hip
Heating type
Oil
Roof Cover
Asph/F Gls/Cmp
Heating fuel
Hot Water
Frame type
Air Condition (%)
Sidings
Wood Shingle
Assessment Information
Fiscal Year
2025
Land Value
$1,466,700.00
Total value
$4,157,200.00
Building value
$2,690,500.00
Estimated tax
$13,635.00
Yard improvement value
$0.00
Flood Map MassMapper Google Street View
Certified Mass Appraisal
20082009201020112012201320142015201620172018201920202021202220232024$0$500,000$1,000,000$1,500,000$2,000,000$2,500,000$3,000,000$3,500,000$4,000,000$4,500,000Total Assessment ($)ImprovementsLandBuildingTotal Assessment
Comparable Properties
Mailing Labels $Valuation Report
7 Skiff Lane24 Meadow View Drive2 Wamasquid Place4 Sunset Hill Lane16 Federal Street21 Pleasant Street$0$500,000$1,000,000$1,500,000$2,000,000$2,500,000$3,000,000$3,500,000$4,000,000$4,500,000Subject PropertyTotal Assessment ($)Total Assessment
Address 21 Pleasant Street A) 16 Federal StreetB) 4 Sunset Hill LaneC) 7 Skiff LaneD) 2 Wamasquid PlaceE) 24 Meadow View Drive
Photo
Plan
Map
Proximity 0.40.70.70.90.9
Last Sold 2/4/20254/15/20253/27/20252/13/202512/4/2024
Price $5,100,000$3,200,000$1,700,000$2,500,000$2,250,000
Net Living Area 1,5471,8821,5511,9662,212
Stories 1.51.51.7522
Sale Price/sft $3,809.40$3296.70$1700.32$1096.07$1271.62$1017.18
Style ConventionalConventionalConventionalCape CodColonialColonial
Age 192319001926200819851977
Rooms
Bedrooms 333333
Full baths 122322
Half baths 2111
Gross Living Area 326617543993213743724484
Heating Fuel Hot WaterForced Air-DucForced Air-DucHot WaterElectr BasebrdHot Water
Detached Garage
Lot Size 0.110.060.070.111.70.46
Roof Cover Asph/F Gls/CmpAsph/F Gls/CmpAsph/F Gls/CmpWood ShingleWood ShingleAsph/F Gls/Cmp
AEM Value - Building $2,690,500.00$1,165,200$1,037,600$776,600$950,900$1,017,400
AEM Value - Land $1,466,700.00$1,655,700$1,208,200$478,800$1,291,100$1,173,400
AEM Value - Other $0.00$0$0$0$0$0
AEM Value - Total $4,157,200.00$2,820,900$2,245,800$1,255,400$2,242,000$2,190,800
# Address Last Sold Sale Price Dist(m) Style LA (sq ft) Lot(ac) BR F-HB
@ 21 Pleasant Street 3/20/2025 $7,375,000 0 Conventional 1,936 0.11 3 1-2 -
  Criteria
A 16 Federal Street 2/4/2025 $5,100,000 0.4 Conventional 1,547 0.06 3 2-1
B 4 Sunset Hill Lane 4/15/2025 $3,200,000 0.7 Conventional 1,882 0.07 3 2-
C 7 Skiff Lane 3/27/2025 $1,700,000 0.7 Cape Cod 1,551 0.11 3 3-1
D 2 Wamasquid Place 2/13/2025 $2,500,000 0.9 Colonial 1,966 1.7 3 2-
E 24 Meadow View Drive 12/4/2024 $2,250,000 0.9 Colonial 2,212 0.46 3 2-1
Averages 95 days $2,950,000 0.70 --- 1,832 0.48 --- ---  

Estimation of Market Value - $4,409,807

As of today, 05/23/2025, the estimated market value of 21 Pleasant Street, Nantucket considering the above 5 comparable properties is $4,409,807.

 

In estimating the current market value, RealtyInSite follows the sales comparison (market) approach which is an approach based on the principles of supply and demand (principle of change) and the principle of substitution. The principle of substitution assumes that a prudent person will pay no more for a property than it would cost to purchase a comparable substitute property.

 

Comparable sales data are applied to arrive at an estimate of value. By default, comparable properties are those properties located within 1 mile of the subject property that have sold within the last 6 months and have a similar size of living area. The table shown above lists the comparable properties that were considered. Note that which properties are considered comparables can be adjusted by varying the selection criteria or deleting non-representative properties.

Neighboring Properties
Mailing Labels
Subject Property8 Farmer Street6 Farmer Street4 Farmer Street5 Farmer Street3 Farmer Street10 Charter Street1 Farmer Street47 Fair Street14 Darling Street25-A Pine Street23 Pine Street5 Hillers Lane3 Hillers Lane7 Farmer Street12 Darling Street43 Fair Street45 Fair Street26 Pine Street7 Darling Street21 Pleasant Street10 Darling Street24 Pine Street2 Farmer Street3 Darling Street9 Darling Street6 Darling Street8-A Darling Street$0$1,000,000$2,000,000$3,000,000$4,000,000$5,000,000$6,000,000$7,000,000Total Assessment ($)Total Assessment
# Address Last Sold Sale Price Dist(m) Style LA (sq ft) Lot(ac) BR F-HB
@ 21 Pleasant Street 3/20/2025 $7,375,000 0 Conventional 1,936 0.11 3 1-2 -
  Criteria
A 3 Angola Street 11/23/2011 $0 0.0 Colonial 2,713 0.19 4 4-
B 23 Pleasant Street 3/5/2021 $0 0.0 Cape Cod 2,448 0.36 4 2-1
C 4 Candle House Lane 1/27/2020 $0 0.0 Outbuildings 0.19 -
D 24 Pleasant Street 8/15/2022 $4,295,000 0.0 Colonial 3,018 0.09 4 4-1
E 26 Pleasant Street 9/19/2013 $2,000,000 0.0 Antique 3,231 0.16 4 5-2
F 6 Candle House Lane 11/8/2012 $1,350,000 0.0 Colonial 2,368 0.12 4 3-1
G 9 Candle House Lane 1/4/2010 $0 0.0 Conventional 1,352 0.6 1 1-
H 22 Pleasant Street 6/17/2021 $2,575,000 0.0 Conventional 2,117 0.14 3 2-1
I 5 Angola Street 2/7/2020 $0 0.0 Colonial 3,308 0.12 3 3-
J 1 South Mill Street 6/24/2024 $900,000 0.0 Outbuildings 0.03 -
K 6 Angola Street 10/24/2012 $0 0.0 Colonial 2,518 0.12 4 3-
L 25-C Pine Street 3/18/2021 $0 0.0 Antique 3,070 0.12 3 4-
M 25-B Pine Street 3/21/1988 $0 0.0 Cape Cod 2,296 0.12 5 3-
N 28 Pleasant Street 4/29/2022 $0 0.0 Colonial 2,075 0.07 3 4-
O 27 Pine Street 1/26/2016 $2,140,000 0.0 Antique 2,663 0.12 4 3-1
P 25-A Pine Street 1/31/2019 $1,400,000 0.0 Colonial 2,528 0.09 4 4-2
Q 19 Pleasant Street 1/4/2010 $0 0.0 Mansion 5,272 0.21 5 5-4
R 8 Angola Street 9/15/1999 $370,000 0.0 Vacant Land 0.12 -
S 25 Pleasant Street 6/15/2018 $1,675,000 0.0 Antique 1,721 0.12 4 3-
T 2 South Mill Street 10/28/2009 $1,154,621 0.0 Conventional 1,400 0.08 3 2-
U 23 Pine Street 11/12/2019 $1,450,000 0.0 Colonial 2,500 0.09 3 4-
V 30 Pleasant Street 1/14/2016 $1,448,000 0.0 Cape Cod 1,393 0.06 4 2-
W 20 Pleasant Street 9/8/2004 $2,520,000 0.0 Antique 3,351 0.15 4 3-2
X 10 Candle House Lane 10/27/2020 $3,550,000 0.0 Custom Built 5,366 0.15 5 5-2
Y 31 Pine Street 10/14/2016 $2,950,000 0.0 Antique 3,566 0.13 3 2-1
Z 3 South Mill Street 2/13/2017 $2,725,000 0.1 Conventional 2,743 0.5 4 2-1
- 4 South Mill Street 2/17/2021 $0 0.1 Service Shop 2,304 0.17 0 1-
- 2 Mill Street $0 0.1 Colonial 1,917 0.13 3 4-
- 21 Pine Street 3/13/2024 $3,725,000 0.1 Antique 1,449 0.1 3 3-
- 26 Pine Street 12/29/2020 $3,025,000 0.1 Antique 2,808 0.07 3 4-1
- 33 Pine Street 10/3/2013 $0 0.1 Antique 3,020 0.09 5 2-1
- 24 Pine Street 1/15/2002 $1,100,000 0.1 Colonial 3,261 0.13 5 4-
- 32 Pleasant Street 2/23/2018 $1,525,000 0.1 Antique 1,525 0.08 3 3-
- 14 Darling Street 7/17/2020 $2,300,000 0.1 Antique 1,750 0.05 3 2-1
- 11 Candle House Lane $0 0.1 Vacant Land 0.12 -
- 29 Pleasant Street 9/16/2008 $0 0.1 Family Conver. 1,895 0.21 3 2-
- 17 Pleasant Street 7/5/2024 $3,715,000 0.1 Antique 2,100 0.09 2 3-
- 35 Pine Street 5/17/2019 $2,260,000 0.1 Antique 2,259 0.08 5 3-1
- 28 Pine Street 9/17/2014 $2,305,000 0.1 Antique 1,828 0.13 3 3-1
- 10-B Angola Street 12/7/2021 $2,000,000 0.1 Colonial 2,814 0.2 3 3-
- 16 Pleasant Street 11/16/2020 $1,645,000 0.1 Antique 1,706 0.06 2 2-1
- 12 Darling Street 11/4/2021 $3,195,500 0.1 Antique 2,973 0.05 3 3-1
- 8 South Mill Street 7/11/2016 $0 0.1 Colonial 3,096 0.13 4 4-1
- 12 Candle House Lane 8/31/2011 $2,420,000 0.1 Antique 4,023 0.14 4 5-2
- 19 Pine Street 12/21/2020 $1,957,515 0.1 Antique 2,124 0.1 3 2-1
- 4 Mill Street $0 0.1 Antique 2,737 0.2 4 2-
- 14 Lyon Street 9/29/2000 $850,000 0.1 Conventional 1,277 0.05 3 2-1
- 10 Darling Street 12/31/2012 $0 0.1 Antique 2,928 0.15 5 3-
- 30 Pine Street 9/16/2009 $1,150,000 0.1 Antique 1,611 0.07 2 3-1
- 7 Farmer Street 9/16/2022 $3,400,000 0.1 Antique 3,516 0.09 4 4-
- 3 Mill Street $0 0.1 Colonial 2,425 0.22 4 4-
- 14 Pleasant Street 12/10/2021 $2,500,000 0.1 Antique 1,924 0.09 3 3-
- 32 Pine Street 9/4/2020 $1,550,000 0.1 Antique 2,028 0.06 2 2-1
- 10 South Mill Street 5/22/2014 $1,465,000 0.1 Colonial 2,952 0.17 4 4-1
- 15 Pleasant Street 9/15/2020 $6,550,000 0.1 Antique 4,687 0.24 6 4-1
- 34 Pleasant Street 6/22/2022 $0 0.1 Antique 1,960 0.19 3 2-
- 8-A Darling Street 9/9/1991 $750,000 0.1 Condominium 5,432 0 5 4-1
- 11 Darling Street 4/19/1994 $0 0.1 Antique 2,604 0.12 4 3-
- 34 Pine Street 6/10/2016 $1,340,000 0.1 Antique 1,565 0.04 4 4-
- 9 South Mill Street 3/14/2003 $0 0.1 Vacant Land 0.33 -
- 14 Candle House Lane 11/2/2017 $0 0.1 Vacant Land 0.13 -
- 1 High Street 10/16/2020 $2,450,000 0.1 Antique 1,568 0.05 4 3-
- 37 Pine Street 12/23/2019 $3,775,000 0.1 Antique 2,030 0.08 5 5-1
- 2 North Mill Street 9/8/2004 $0 0.1 Antique 1,672 0.12 4 3-
- 36 Pine Street 10/28/2009 $1,300,000 0.1 Antique 1,904 0.08 3 3-
- 5 Farmer Street 10/18/2017 $0 0.1 Antique 2,329 0.06 3 4-
- 10 Hillers Lane $0 0.1 Colonial 1,412 0.12 3 2-
- 8 Farmer Street 3/11/2010 $0 0.1 Antique 1,121 0.04 3 2-
- 33 Pleasant Street 6/13/2019 $1,871,000 0.1 Colonial 2,284 0.23 4 5-
- 14 South Mill Street 7/14/2004 $0 0.1 Custom Built 2,899 0.27 3 3-1
- 13 Pleasant Street 3/30/2011 $0 0.1 Antique 2,741 0.14 4 3-1
- 8 Mill Street $737,400 0.1 Antique 3,104 0.11 4 3-
- 6 Darling Street 12/29/2020 $0 0.1 Antique 4,539 0.24 6 4-1
- 7 Twin Street 7/22/2013 $0 0.1 Antique 2,800 0.1 4 4-1
- 9 Darling Street 4/2/2004 $3,500,000 0.1 Antique 4,262 0.19 4 4-1
- 16 Candle House Lane 11/2/2017 $1,500,000 0.1 Vacant Land 0.12 -
- 12 Pleasant Street 12/19/2012 $0 0.1 Antique 3,336 0.16 4 4-1
- 5 Mill Street 10/20/2015 $2,215,000 0.1 Antique 4,215 0.17 6 6-1
- 17 Pine Street 9/25/2020 $2,720,000 0.1 Antique 2,192 0.08 4 4-1
- 3 Farmer Street 8/26/2005 $1,575,000 0.1 Antique 1,835 0.04 4 3-
- 41 Pine Street 7/20/2009 $0 0.1 Conventional 1,645 0.12 2 2-1
- 3 Tattle Court 9/16/2003 $0 0.1 Antique 2,524 0.13 4 4-1
- 38 Pine Street 1/31/2024 $2,225,000 0.1 Antique 1,707 0.07 3 1-1
- 6 Farmer Street 1/14/2005 $0 0.1 Antique 1,474 0.06 3 2-
- 36 Pleasant Street 10/21/2004 $1,100,000 0.1 Custom Built 3,903 0.13 4 4-1
- 4 Starbuck Court 12/12/2022 $2,950,000 0.1 Antique 1,709 0.13 2 1-1
- 35 Pleasant Street 9/17/2024 $3,735,000 0.1 Bungalow 1,680 0.23 2 1-
- 7 Darling Street 6/22/2016 $0 0.1 Colonial 3,156 0.12 5 2-1
- 18 Pine Street 5/16/2014 $3,262,000 0.1 Antique 2,819 0.11 4 4-
- 7 Lyon Street 5/8/2006 $0 0.1 Conventional 1,502 0.1 4 2-
- 4 Farmer Street 6/20/2007 $0 0.1 Antique 2,118 0.07 3 4-
- 11 Pleasant Street 1/22/2020 $2,100,000 0.1 Antique 3,732 0.16 4 5-1
- 7 South Mill Street 3/14/2003 $0 0.1 Conventional 2,218 0.59 3 2-1
- 1 Farmer Street 5/10/2024 $3,600,000 0.1 Antique 2,430 0.06 3 3-1
- 14 Jefferson Lane 2/28/1989 $430,000 0.1 Colonial 2,816 0.13 4 2-1
- 40 Pine Street 11/16/2022 $2,530,000 0.1 Antique 1,410 0.08 2 4-1
- 5 Hillers Lane 12/2/2021 $3,000,000 0.1 Colonial 2,240 0.08 3 3-1
- 1 Starbuck Court 4/4/1997 $0 0.1 Conventional 2,821 0.21 4 4-
- 4 Darling Street 11/15/2000 $1,950,000 0.1 Antique 3,763 0.1 4 3-
- 15 Pine Street 7/9/2007 $0 0.1 Antique 3,884 0.08 4 5-1
- 10 Pleasant Street 1/10/1985 $720,000 0.1 Antique 4,027 0.18 5 4-1
- 37 Pleasant Street 8/30/2022 $0 0.1 Cape Cod 2,738 0.19 4 3-1
- 3 Darling Street 10/5/1995 $0 0.1 Antique 3,088 0.23 5 4-
- 10 Lyon Street 11/13/2023 $4,250,000 0.1 Antique 3,095 0.08 8 8-
- 2 Farmer Street 5/11/2022 $4,895,000 0.1 Antique 4,351 0.09 4 3-1
- 16 Pine Street 2/23/2015 $0 0.1 Antique 2,654 0.09 4 4-
- 9 Mill Street 1/15/1997 $0 0.1 Antique 2,676 0.12 4 4-
- 1 Twin Street 3/30/2022 $9,850,000 0.1 Antique 4,809 0.22 6 4-1
- 5 Lyon Street 1/12/2021 $1,175,000 0.1 Antique 1,452 0.04 3 3-
- 43 Pine Street 11/8/2011 $1,320,000 0.1 Antique 1,788 0.12 4 2-1
- 3 Hillers Lane 11/25/1996 $574,500 0.1 Colonial 2,118 0.08 3 3-1
- 10 Mill Street 5/1/1997 $0 0.1 Vacant Land 0.33 -
- 39 Fair Street 7/30/2020 $1,950,000 0.1 Antique 1,524 0.08 3 2-1
- 3 North Mill Street 9/30/2022 $0 0.1 Antique 2,563 0.26 5 3-
- 10 Charter Street 11/17/1994 $430,000 0.1 Antique 1,875 0.08 3 3-
- 37 Fair Street 8/27/2018 $3,225,000 0.1 Antique 2,576 0.14 5 3-
- 9 Pleasant Street 1/7/2014 $5,100,000 0.1 Antique 5,301 0.28 6 5-1
- 8-B Lyon Street 1/27/2023 $1,400,000 0.1 Bungalow 850 0.04 1 1-
- 5-A Jefferson Lane 10/9/2013 $360,000 0.1 Condominium 384 0 1 1-
- 38 Pleasant Street 10/2/2024 $4,970,000 0.1 Conventional 3,147 0.17 5 4-1
- 8 Pleasant Street 3/27/2018 $0 0.1 Antique 3,059 0.17 3 3-1
- 43 Fair Street 1/4/2011 $0 0.1 Antique 2,984 0.11 4 4-
- 39 York Street $0 0.1 Outbuildings 1.36 -
- 33 Fair Street 4/15/2021 $3,168,750 0.1 Antique 2,804 0.07 4 3-1
- 39 Pleasant Street 8/11/2021 $400,000 0.1 Conventional 2,394 0.24 4 1-1
- 41 Fair Street 8/2/2023 $2,925,000 0.1 Antique 1,686 0.04 4 3-1
- 11 Pine Street 10/3/2024 $3,500,000 0.1 Colonial 2,192 0.13 3 3-
- 8 Charter Street 10/11/2013 $1,275,000 0.1 Antique 1,175 0.05 3 2-1
- 45 Pine Street 2/25/2014 $0 0.1 Ranch 1,784 0.11 3 2-1
- 3 Lyon Street 12/15/2022 $2,800,000 0.1 Antique 1,958 0.09 4 3-1
- 42 Pine Street 9/25/2013 $1,500,000 0.1 Antique 1,983 0.07 4 2-1
- 29 Fair Street 4/15/2021 $2,819,444 0.1 B+B/Inn 3,964 0.11 5 4-1
- 44 Prospect Street 3/8/1988 $450,000 0.1 Antique 2,069 0.57 4 3-
- 8 Lyon Street 4/3/2019 $0 0.1 Antique 1,704 0.1 3 1-1
- 6 Charter Street 6/5/2012 $0 0.1 Antique 1,250 0.04 3 1-1
- 45 Fair Street 5/8/2024 $4,800,000 0.1 Custom Built 2,854 0.07 4 4-1
- 14 Pine Street 3/31/2023 $4,195,000 0.1 Antique 3,585 0.12 5 4-
- 48 Prospect Street 9/1/1989 $0 0.1 Colonial 2,144 0.34 4 3-
- 9 Eagle Lane 1/3/2017 $0 0.1 Antique 1,661 0.06 3 2-
- 38 North Mill Street 7/15/2022 $5,250,000 0.1 Colonial 3,959 0.2 7 7-1
- 6 Pleasant Street 11/21/2022 $1,550,000 0.1 Antique 3,033 0.1 5 3-
- 11 Mill Street-Lot 32 10/25/2019 $0 0.1 Antique 4,387 0.29 5 3-1
- 47 Fair Street 3/15/2007 $2,650,000 0.1 Antique 2,447 0.08 5 4-
- 49 Pine Street 11/4/2021 $4,025,000 0.1 Colonial 3,533 0.11 6 5-1
- 50 Prospect Street $0 0.1 Outbuildings 0.44 -
- 41 Pleasant Street 1/7/2022 $0 0.1 Colonial 3,793 0.23 5 4-1
- 7 Pleasant Street 2/25/2025 $12,300,000 0.1 Antique 5,722 0.3 5 7-
- 2 Charter Street 8/7/2014 $500,000 0.1 Bungalow 999 0.05 1 1-
- 6 Lyon Street 10/30/2007 $0 0.1 Antique 1,560 0.1 3 1-1
- 8 Jefferson Lane 10/29/2021 $0 0.1 Cape Cod 2,091 0.05 3 3-1
- 1 Lyon Street 1/27/2020 $3,800,000 0.1 Antique 2,035 0.05 4 5-1
- 12 Pine Street 8/15/2017 $4,450,000 0.1 Antique 4,151 0.16 8 4-1
Averages 4030 days $1,541,669 0.08 --- 2,430 0.15 --- ---  
DISCLAIMER: The information in this report was collected from the concerned Assessors Office and Registry of Deeds.  Compu-Links disclaims any and all representations or warranties as to the accuracy of this information
5541 1 21 Pleasant Street