Gehl — Making Cities for People Hillsdale Redevelopment November 3, 2025
City of San Mateo
City Council Study Session
Gehl — Making Cities for People Hillsdale Redevelopment 2 Better
than before
● Enhanced regional
shopping destination
● New open spaces for
community
● Multi-modal access
● Activating mix of uses
● Added housing to
address critical need
● Contribution to San
Mateo's economic
vibrancy
Hillsdale Reimagined
Gehl — Making Cities for People
Gehl — Making Cities for People
Responding to the community’s
needs over time
3 Blaine Merker
Gehl
Director of Engagement
The rise of the
shopping center
The Heyday of
the Mall
Opportunity: Vibrant,
Mixed-Use Destination
Hillsdale Reimagined
Experiential
shopping
Gehl — Making Cities for People
4 3 Site Walks
4+ Neighborhood and
Community Meetings
12 Community
Pop-Ups
Hillsdale Reimagined
8,500+
PEOPLE ENGAGED
Gehl — Making Cities for People
5 Hillsdale Reimagined
Hillsdale
Reimagined
Gehl — Making Cities for People
Gehl — Making Cities for People
6 Vibrant regional
retail
North
Block
150K sq ft of tenanted retail (approx.)
40 retailers (approx.)
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
Hillsdale Reimagined
Gehl — Making Cities for People
Hillsdale Reimagined
7 North
Block
A neighborhood grocer
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
Hillsdale Reimagined
Gehl — Making Cities for People
Hillsdale Reimagined
8 Hillsdale
Square
Hillsdale
Center
North
Block
Expanded public realm to
Hillsdale Center and
Hillsdale Square
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
Hillsdale Reimagined
Gehl — Making Cities for People
Hillsdale Reimagined
9 Hillsdale
Caltrain
Station
Hillsdale
Square
Hillsdale
Center
North
Block
Improved ECR-31st
connections
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
Hillsdale Reimagined
Gehl — Making Cities for People
Hillsdale Reimagined
10 Network of neighborhood
open spaces
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
Hillsdale
Caltrain
Station
Hillsdale
Square
Hillsdale
Center
North
Block
Neighborhood
Passage
Creekside
Walk
Townhome Way
Edison Greenway
4.5 acres of new open spaces (approx.)
Hillsdale Reimagined
Gehl — Making Cities for People
Hillsdale Reimagined
11 Better routes for
walking and biking
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
Hillsdale
Caltrain
Station
Hillsdale
Square
Hillsdale
Center
North
Block
Neighborhood
Passage
Creekside
Walk
Townhome Way
Edison Greenway
Hillsdale Reimagined
Gehl — Making Cities for People
Hillsdale Reimagined
12 A range of housing types
meeting San Mateo’s
housing needs
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
Hillsdale
Caltrain
Station
Hillsdale
Square
Hillsdale
Center
North
Block
Neighborhood
Passage
Creekside
Walk
Townhome Way
Edison Greenway
Hillsdale Reimagined
Gehl — Making Cities for People
Hillsdale Reimagined
13 A scale that meets the
neighborhood
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
Hillsdale
Caltrain
Station
Hillsdale
Square
Hillsdale
Center
North
Block
Neighborhood
Passage
Creekside
Walk
Townhome Way
Edison Greenway
Hillsdale Reimagined
Gehl — Making Cities for People
Hillsdale Reimagined
14 Height and
workplaces towards
El Camino Real
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
Hillsdale
Caltrain
Station
Hillsdale
Square
Hillsdale
Center
North
Block
Neighborhood
Passage
Creekside
Walk
Townhome Way
Edison Greenway
Hillsdale Reimagined
Gehl — Making Cities for People
Hillsdale Reimagined
15 A mixed-use, regional
destination
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
Hillsdale
Caltrain
Station
Hillsdale
Square
Hillsdale
Center
North
Block
Neighborhood
Passage
Creekside
Walk
Townhome Way
Edison Greenway
Hillsdale Reimagined
Gehl — Making Cities for People
Gehl — Making Cities for People
El Camino Real
16 New Gateway to Hillsdale
Hillsdale Reimagined
16Gehl — Making Cities for People
El Camino Real
Gehl — Making Cities for People
New Gateway to Hillsdale
Hillsdale Reimagined
17Gehl — Making Cities for People
El Camino Real
Gehl — Making Cities for People
Hillsdale Center
Shopping and Dining Heart
Hillsdale Reimagined
18Gehl — Making Cities for People
Gehl — Making Cities for People
Hillsdale Center
Shopping and Dining Heart
Hillsdale Reimagined
19Gehl — Making Cities for People
Gehl — Making Cities for People
East Sailer Dr.
Complete streets lined
with ground floor retail
Hillsdale Reimagined
20Gehl — Making Cities for People
Gehl — Making Cities for People
Hillsdale Square
Actively programmed
community green space
Hillsdale Reimagined
21Gehl — Making Cities for People
Gehl — Making Cities for People
Edison Greenway
22 A comfortable, scaled transition
Hillsdale Reimagined
Gehl — Making Cities for People
Gehl — Making Cities for People
A Day in
the Life
at Hillsdale
Let’s take a stroll
through Hillsdale
Reimagined
YOUNG FAMILY
OFFICE WORKER
LOCAL NEIGHBORS
Hillsdale Reimagined
23 Gehl — Making Cities for People
24 YOUNG FAMILY
Gehl — Making Cities for People
Hillsdale Reimagined
24 EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
Gehl — Making Cities for People
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
25 7:45 AM
Walk the dog
through
Greenways and
Passages
YOUNG FAMILY
Gehl — Making Cities for People
Hillsdale Reimagined
25 Gehl — Making Cities for People
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
26 7:45 AM
Walk the dog
through
Greenways and
Passages
YOUNG FAMILY
Gehl — Making Cities for People
Hillsdale Reimagined
26 8:15 AM
Walk to Laurel
Elementary for
kid drop off
YOUNG FAMILY
Gehl — Making Cities for People
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
27 7:45 AM
Walk the dog
through
Greenways and
Passages
YOUNG FAMILY
Gehl — Making Cities for People
Hillsdale Reimagined
27 8:15 AM
Walk to Laurel
Elementary for
kid drop off
YOUNG FAMILY
8:45 AM and 5:15 PM
Drive to and from
work
YOUNG FAMILY
Gehl — Making Cities for People
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
28 7:45 AM
Walk the dog
through
Greenways and
Passages
YOUNG FAMILY
Gehl — Making Cities for People
Hillsdale Reimagined
28 8:15 AM
Walk to Laurel
Elementary for
kid drop off
YOUNG FAMILY
8:45 AM and 5:15 PM
Drive to and from
work
YOUNG FAMILY
5:30 PM
Youth class in
Hillsdale
Square after
arriving home
Gehl — Making Cities for People
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
29 7:45 AM
Walk the dog
through
Greenways and
Passages
YOUNG FAMILY
Gehl — Making Cities for People
Hillsdale Reimagined
29 8:15 AM
Walk to Laurel
Elementary for
kid drop off
YOUNG FAMILY
8:45 AM and 5:15 PM
Drive to and from
work
5:30 PM
Youth class in
Hillsdale
Square after
arriving home
YOUNG FAMILY
6:30 PM
Grocery stop to pick
up ingredients for
family dinner on the
way home
Gehl — Making Cities for People
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
8:30 AM and
6:30 PM
Walk to and
from work
from Caltrain
Station
OFFICE WORKER
30 Gehl — Making Cities for People 30
9:15 AM
Coffee
meeting in
Hillsdale
Square
Gehl — Making Cities for People
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
8:30 AM and
6:30 PM
Walk to and
from work
from Caltrain
Station
31 Gehl — Making Cities for People 31
9:15 AM
Coffee
meeting in
Hillsdale
Square
9:15 AM
Coffee
meeting in
Hillsdale
Square
OFFICE WORKER
Gehl — Making Cities for People
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
8:30 AM and
6:30 PM
Walk to and
from work
from Caltrain
Station
32 Gehl — Making Cities for People 32
9:15 AM
Coffee
meeting in
Hillsdale
Square
9:15 AM
Coffee
meeting in
Hillsdale
Square
OFFICE WORKER
11:15 AM
Nearby
business
meeting
Gehl — Making Cities for People
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
8:30 AM and
6:30 PM
Walk to and
from work
from Caltrain
Station
33 Gehl — Making Cities for People 33
9:15 AM
Coffee
meeting in
Hillsdale
Square
9:15 AM
Coffee
meeting in
Hillsdale
Square
11:15 AM
Nearby
business
meeting
OFFICE WORKER
12:00 PM
Lunch in
Hillsdale
Square
Gehl — Making Cities for People
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
8:30 AM and
6:30 PM
Walk to and
from work
from Caltrain
Station
34 Gehl — Making Cities for People 34
9:15 AM
Coffee
meeting in
Hillsdale
Square
9:15 AM
Coffee
meeting in
Hillsdale
Square
11:15 AM
Nearby
business
meeting
12:00 PM
Lunch in
Hillsdale
Square
OFFICE WORKER
4:45 PM
Quick stop at
store for
friend's
birthday gift
Gehl — Making Cities for People
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
8:30 AM and
6:30 PM
Walk to and
from work
from Caltrain
Station
35 Gehl — Making Cities for People 35
9:15 AM
Coffee
meeting in
Hillsdale
Square
9:15 AM
Coffee
meeting in
Hillsdale
Square
11:15 AM
Nearby
business
meeting
12:00 PM
Lunch in
Hillsdale
Square
4:45 PM
Quick stop at
store for
friend's
birthday gift
OFFICE WORKER
5:15 PM
Coworker
happy hour at
Flores
Gehl — Making Cities for People
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
8:30 AM and
6:30 PM
Walk to and
from work
from Caltrain
Station
36 Gehl — Making Cities for People 36
9:15 AM
Coffee
meeting in
Hillsdale
Square
9:15 AM
Coffee
meeting in
Hillsdale
Square
11:15 AM
Nearby
business
meeting
12:00 PM
Lunch in
Hillsdale
Square
4:45 PM
Quick stop at
store for
friend's
birthday gift
5:15 PM
Coworker
happy hour at
Flores
OFFICE WORKER
8:30 AM and
6:30 PM
Walk to and
from work
from Caltrain
Station
Gehl — Making Cities for People
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
37 LOCAL NEIGHBORS
10:00 AM
Farmers
market and
athletic store
stop
Hillsdale Reimagined
Gehl — Making Cities for People 37
Gehl — Making Cities for People
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE
10:00 AM
Farmers
market and
athletic store
stop
38 LOCAL NEIGHBORS
11:00 AM
Bike Group
meet-up and
Sunday ride
Hillsdale Reimagined
Gehl — Making Cities for People 38
Gehl — Making Cities for People
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE 11:00 AM
Bike Group
meet-up and
Sunday ride
10:00 AM
Farmers
market and
athletic store
stop
39 LOCAL NEIGHBORS
2:00 PM
Lunch with
Bike Group
Hillsdale Reimagined
Gehl — Making Cities for People 39
Gehl — Making Cities for People
EL CAMINO REAL (CA -82)
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
HILLSDALE BLVD
31ST AVENUE 11:00 AM
Bike Group
meet-up and
Sunday ride
10:00 AM
Farmers
market and
athletic store
stop
2:00 PM
Lunch with
Bike Group
40 LOCAL NEIGHBORS
4:00 PM
Live music
and drinks
with
neighbors
Hillsdale Reimagined
Gehl — Making Cities for People 40
Gehl — Making Cities for People
● Reaffirming Hillsdale as a regional retail destination ● ~4.5 acres of new open space
● Hillsdale Square: farmers markets, movie nights, and community events ● New off-street bike paths next to Edison St and Hillsdale Blvd ● Coordination on an improved El Camino Real - 31st Ave intersection ● Up to 250 affordable homes
● Sustainability: all-electric operations and CalGreen -compliant buildings ● ~$114M Development Impact Fees
● Current annual tax revenue ($5.0M) doubles to $10.7M
● Accounting for services to accommodate new development, net contribution to city General Fund changes from $4.37M to $5.65M 41 Hillsdale Reimagined
Benefits
Gehl — Making Cities for People
● Technical studies
● Thematic community
engagement
Our Next Steps What We Heard
Timeline
El Camino
Crossing
Traffic
Regional
Retail
Fiscal Impact
● Timeline
Complete by 2040
● Fiscal Impact
Net addition of $1.27M - $2.2M to SM GF
● Regional Retail
40 new retailers
● El Camino Crossing
Initial concept plans
● Traffic
25% trip reduction
Hillsdale Reimagined
42Gehl — Making Cities for People
Gehl — Making Cities for People 43
Appendix
Gehl — Making Cities for People 44
Landscape Plan
Hillsdale Reimagined
Gehl — Making Cities for People 45
VTM
Hillsdale Reimagined
Gehl — Making Cities for People
46 Site Plan: Ground Floor
Hillsdale Reimagined
Gehl — Making Cities for People
47 Site Plan: Basement Level 1
Hillsdale Reimagined
Gehl — Making Cities for People
48 Site Plan: Basement Level 2
Hillsdale Reimagined
Gehl — Making Cities for People
4.5 Acres
Open Space
Up to
1,670 Homes
(1,387 in Re-submittal Application)
49 Hillsdale Reimagined
Up to 250 Below Market Rate
(208 in Re-submittal Application)
Hillsdale
Reimagined
will have a
vibrant mix of
new uses and
amenities,
including
homes, retail,
dining, and
office.
2.1M SF
Office and Retail
150K Retail
+2,000
New Parking Spaces
Gehl — Making Cities for People 50
Program
Summary
Hillsdale Reimagined
*Includes above ground covered
parking
**Includes above ground covered
parking and below grade level(s)
Gehl — Making Cities for People
Hillsdale Today
Hillsdale Mall
(Center Block)
Hillsdale
North Block
Macy’s
Nordstrom
P
Existing department
anchors (365K)
222K
Mall’s Occupied Retail
(72 Tenants)
135K
South Block
P
P
P
P
P
Hillsdale
South Block
Trader
Joe's
200K
North Block
51 EL CAMINO REAL (CA -82)
31st Avenue
EL CAMINO REAL (CA -82)
Gehl — Making Cities for People
W Hillsdale Blvd
Townh ome Way
Inn er Alley
Edison Street
West Sailer Drive
East Sailer Drive
33 rd Avenu e
32 nd Avenue
35 th Lane
52 Hillsdale will remain a regional retail destination with a vibrant ground floor program.
200K
North Block
P
Grocery
Store
Hillsdale
North Block
Hillsdale Reimagined
150K
Retail
(40 Tenants)
EL CAMINO REAL (CA -82)
31st Avenue
EL CAMINO REAL (CA -82)
Gehl — Making Cities for People 53
Retail Demising
Hillsdale Reimagined
Gehl — Making Cities for People 54
Hillsdale Reimagined
Hillsdale Reimagined
Concept Study: Pedestrian Improvements at
El Camino Real and 31st Ave Intersection
Gehl — Making Cities for People
We like being near the
Hillsdale Caltrain station
Bay Meadows office employees
don’t drive a car to work
Hillsdale Reimagined
55 The Hillsdale Station is the seventh
busiest station out of all 29
40-50%
#7
Gehl — Making Cities for People
San Mateo County Downtown San Mateo Bay Meadows
(Hillsdale Caltrain)
San Mateo County
$5.78
$8.09
Downtown San Mateo
New, transit-adjacent office is more in demand
in today’s real estate market
Office Occupancy Rates
Average office
asking rents
per square foot
Hillsdale Reimagined
56 78% 83% 93%
56 Gehl — Making Cities for People 57
$1.27M to $2.2M
annual net benefit
Hillsdale Reimagined
Hillsdale Reimagined
will generate an additional
This projection
represents a
minimum of a
29% increase
annual net benefit
to the city. to the City of San Mateo’s
General Fund.
Gehl — Making Cities for People
5858
Phasing
Hillsdale Reimagined
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Phasing
Hillsdale Reimagined
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Phasing
Hillsdale Reimagined
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Phasing
Hillsdale Reimagined
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Phasing
Hillsdale Reimagined
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Phasing
Hillsdale Reimagined
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Phasing
Hillsdale Reimagined
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Phasing
Hillsdale Reimagined
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Phasing
Hillsdale Reimagined
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Phasing
Hillsdale Reimagined
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Phasing
Hillsdale Reimagined
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Phasing
Hillsdale Reimagined
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Phasing
Hillsdale Reimagined
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Phasing
Hillsdale Reimagined
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Heights: East to West
Hillsdale Reimagined
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73 Land Use Framework
Hillsdale Reimagined
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74 Parcel Map
Hillsdale Reimagined
Gehl — Making Cities for People
Gehl — Making Cities for People
Building Heights
Hillsdale Reimagined
75Gehl — Making Cities for People
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Hillsdale Reimagined
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77 Hillsdale Reimagined
Grocery Store: Plan
Gehl — Making Cities for People