1744 N. Western Ave

1744 N Western Ave, Chicago, IL 60647

Luxury living with direct access to the 606. Trailhead is the one and only building with a direct connection to the 606. Every day your possibilities are open with a game-changing connection between your home and your trail. Get out there and own it. A neighborhood close to everything. Your home should be your escape from the everyday and your launchpad to whatever the day has to offer. As an entirely walkable, accessible, and connectable place, Trailhead on the 606 is built for every type of vibrant lifestyle. Energize your routine. Step up your game on the trail or in the fitness room. Reward yourself with some time basking on the rooftop or enjoying a fire on the amenity terrace. No matter what your day looks like, premium finishes throughout the building ensure it will be extraordinary. Unbeatable Foot Traffic. With a direct connection to the 606 Trail, and steps from public transportation, the retail spaces at Trailhead are unmatched. Choose from 7,265 SF divisible on Western Ave., 2,568 SF on The 606 Trail, including outdoor patio seating and signage directly on The Trail, or combine to offer a presence on both. View more Request your own private tour

Key Features

Eco Friendly / Green Living Features:


Recycling

This property has an EcoScoreTM of 1 based on it's sustainable and green living features below.

Building Type: Apartment

Total Units: 109

Last Updated: July 15, 2025, 10:52 a.m.

Property Manager: Cagan Management Group

Telephone: (847) 324-8964

Property Website

All Amenities

  • Unit
  • Premium Wood-Look Flooring
  • In-Unit Washer/Dryer
  • Private Balconies*
  • Kitchen
  • Stainless Steel Appliances
  • Green
  • Recycling
  • Pets
  • Pet Friendly
  • Outdoor Amenities
  • Rooftop deck with fire pit & grilling stations
  • Parking
  • On-Site Parking

Other Amenities

  • Contemporary Premium Cabinetry |
  • Tiled Bathroom Floors |
  • Tiled Kitchen Backsplashes |
  • Spacious Walk-In Closets* |
  • Availability 24 Hours |
  • Rooftop Lounge & Kitchen |

Available Units


Floorplan Beds/Baths Rent Track
1 Bedroom - 203 (ARO) 1 Bed/1.0 Bath
709 sf
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Available Now
1 Bedroom - 205 1 Bed/1.0 Bath
801 sf
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1 Bedroom - 225 1 Bed/1.0 Bath
852 sf
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Available Now
1 Bedroom - 303, 307, 309, 407, 409, 509 1 Bed/1.0 Bath
709 sf
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1 Bedroom - 305, 405 1 Bed/1.0 Bath
819 sf
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1 Bedroom - 306, 406, 408, 506, 508 1 Bed/1.0 Bath
708 sf
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Available Now
1 Bedroom - 308 1 Bed/1.0 Bath
678 sf
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1 Bedroom - 312 1 Bed/1.0 Bath
821 sf
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1 Bedroom - 313 1 Bed/1.0 Bath
924 sf
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Available Now
1 Bedroom - 314 1 Bed/1.0 Bath
883 sf
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Available Now
1 Bedroom - 315 1 Bed/1.0 Bath
925 sf
$3,022
Available Now
1 Bedroom - 317 1 Bed/1.0 Bath
841 sf
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Available Now
1 Bedroom - 320 1 Bed/1.0 Bath
640 sf
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Available Now
1 Bedroom - 322 1 Bed/1.0 Bath
883 sf
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1 Bedroom - 325 1 Bed/1.0 Bath
852 sf
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1 Bedroom - B23 1 Bed/1.0 Bath
846 sf
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1 Bedroom - B24 1 Bed/1.0 Bath
800 sf
$3,025
Available Now
1 Bedroom - B25 1 Bed/1.0 Bath
887 sf
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Available Now
1 Bedroom - B26 1 Bed/1.0 Bath
925 sf
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Available Now
1 Bedroom - B27 1 Bed/1.0 Bath
0 sf
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Available Now
1 Bedroom - B28 1 Bed/1.0 Bath
883 sf
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Available Now
1 Bedroom - B29 1 Bed/1.0 Bath
736 sf
$2,665
Available Now
1 Bedroom - B3 1 Bed/1.0 Bath
692 sf
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Available Now
1 Bedroom - B30 1 Bed/1.0 Bath
677 sf
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Available Now
1 Bedroom - B31 1 Bed/1.0 Bath
821 sf
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1 Bedroom - B32 1 Bed/1.0 Bath
841 sf
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1 Bedroom - B33 1 Bed/1.0 Bath
602 sf
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1 Bedroom - B34 1 Bed/1.0 Bath
586 sf
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1 Bedroom - B35 1 Bed/1.0 Bath
584 sf
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1 Bedroom - B36 1 Bed/1.0 Bath
887 sf
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1 Bedroom - B37 1 Bed/1.0 Bath
689 sf
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1 Bedroom - B38 1 Bed/1.0 Bath
841 sf
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1 Bedroom - B39 1 Bed/1.0 Bath
863 sf
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1 Bedroom - B4 1 Bed/1.0 Bath
930 sf
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1 Bedroom - B40 1 Bed/1.0 Bath
933 sf
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1 Bedroom - B41 1 Bed/1.0 Bath
620 sf
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1 Bedroom - B5 1 Bed/1.0 Bath
796 sf
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1 Bedroom - B6 1 Bed/1.0 Bath
925 sf
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1 Bedroom - B7 1 Bed/1.0 Bath
841 sf
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1 Bedroom - B8 1 Bed/1.0 Bath
622 sf
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1 Bedroom - B9 1 Bed/1.0 Bath
800 sf
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1 Bedroom, B27 1 Bed/1.0 Bath
624 sf
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1.5 Bedrooms - 211 1 Bed/1.0 Bath
869 sf
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1.5 Bedrooms - 311 (ARO) 1 Bed/1.0 Bath
866 sf
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1.5 Bedrooms - 411, 511, 611 1 Bed/1.0 Bath
866 sf
$3,195
Available Now
2 Bedrooms - 504 2 Bed/2.0 Bath
1,107 sf
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2 Bedrooms - 510 2 Bed/2.0 Bath
1,265 sf
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2 Bedrooms - 610 2 Bed/2.0 Bath
1,110 sf
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2 Bedrooms - D1 2 Bed/2.0 Bath
1,180 sf
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2 Bedrooms - D2 2 Bed/2.0 Bath
1,180 sf
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2 Bedrooms - D3 2 Bed/2.0 Bath
1,283 sf
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2 Bedrooms - D4 2 Bed/2.0 Bath
1,270 sf
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2.5 Bedrooms - 216 2 Bed/2.0 Bath
1,168 sf
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2.5 Bedrooms - 221 2 Bed/2.0 Bath
1,222 sf
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2.5 Bedrooms - 316 2 Bed/2.0 Bath
1,191 sf
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2.5 Bedrooms - 321 2 Bed/2.0 Bath
1,222 sf
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2.5 Bedrooms - 416 2 Bed/2.0 Bath
1,189 sf
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2.5 Bedrooms - 516 2 Bed/2.0 Bath
1,191 sf
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2.5 Bedrooms - 521 2 Bed/2.0 Bath
1,222 sf
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3 Bedrooms - 224 3 Bed/2.5 Bath
1,196 sf
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3 Bedrooms - 324 (ARO) 3 Bed/2.5 Bath
1,196 sf
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3 Bedrooms - 424 3 Bed/2.5 Bath
1,196 sf
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3 Bedrooms - 523, 623 3 Bed/2.0 Bath
1,420 sf
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3 Bedrooms - 524 3 Bed/2.0 Bath
1,265 sf
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3 Bedrooms - 625 3 Bed/2.0 Bath
1,265 sf
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Efficiency - 204 0 Bed/1.0 Bath
441 sf
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Available Now
Efficiency - A10 0 Bed/1.0 Bath
539 sf
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Efficiency - A11 0 Bed/1.0 Bath
501 sf
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Efficiency - A12 0 Bed/1.0 Bath
575 sf
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Efficiency - A2 0 Bed/1.0 Bath
511 sf
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Efficiency - A3 0 Bed/1.0 Bath
573 sf
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Available Now
Efficiency - A4 0 Bed/1.0 Bath
590 sf
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Available Now
Efficiency - A5 0 Bed/1.0 Bath
441 sf
$1,898
Available Now
Efficiency - A6 0 Bed/1.0 Bath
575 sf
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Available Now
Efficiency - A7 0 Bed/1.0 Bath
573 sf
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Available Now
Efficiency - A8 0 Bed/1.0 Bath
590 sf
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Available Now
Efficiency - A9 0 Bed/1.0 Bath
573 sf
$2,315
Available Now
Townhouse - 101 2 Bed/1.5 Bath
1,547 sf
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Available Now
Townhouse - 102 2 Bed/1.5 Bath
1,666 sf
$4,440
Available Now
[{'date': '2024-05-25 20:05:25.173000', 'lowrent': '$2,925'}, {'date': '2024-08-16 04:15:26.148000', 'lowrent': 'Ask for Pricing'}]
1 Bedroom - 225

1 Bed/1.0 Bath
852 sf SqFt

[{'date': '2024-05-25 20:05:25.243000', 'lowrent': '$2,645'}, {'date': '2024-08-16 04:15:26.273000', 'lowrent': 'Ask for Pricing'}]
1 Bedroom - 306, 406, 408, 506, 508

1 Bed/1.0 Bath
708 sf SqFt

[{'date': '2024-05-25 20:05:26.880000', 'lowrent': 'Ask for Pricing'}, {'date': '2024-10-08 13:13:59.349000', 'lowrent': '$2,375'}, {'date': '2024-10-19 21:44:48.653000', 'lowrent': '$2,495'}, {'date': '2025-03-16 22:13:10.862000', 'lowrent': 'Ask for Pricing'}]
1 Bedroom - 308

1 Bed/1.0 Bath
678 sf SqFt

[{'date': '2024-05-25 20:05:25.312000', 'lowrent': '$2,955'}, {'date': '2024-08-16 04:15:26.399000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-01-03 12:39:53.083000', 'lowrent': '$2,840'}, {'date': '2025-03-16 22:13:08.244000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-05-13 00:45:42.339000', 'lowrent': '$3,055'}, {'date': '2025-06-19 01:39:05.165000', 'lowrent': 'Ask for Pricing'}]
1 Bedroom - 313

1 Bed/1.0 Bath
924 sf SqFt

[{'date': '2024-05-25 20:05:27.010000', 'lowrent': 'Ask for Pricing'}, {'date': '2024-05-31 12:25:15.477000', 'lowrent': '$2,497'}, {'date': '2024-08-16 04:15:25.209000', 'lowrent': '$2,865'}, {'date': '2024-10-08 13:14:00.782000', 'lowrent': 'Ask for Pricing'}]
1 Bedroom - 314

1 Bed/1.0 Bath
883 sf SqFt

[{'date': '2024-05-25 20:05:27.080000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-06-19 01:39:02.661000', 'lowrent': '$3,022'}]
1 Bedroom - 315

1 Bed/1.0 Bath
925 sf SqFt

[{'date': '2024-05-25 20:05:25.377000', 'lowrent': '$2,875'}, {'date': '2024-08-16 04:15:26.882000', 'lowrent': 'Ask for Pricing'}]
1 Bedroom - 325

1 Bed/1.0 Bath
852 sf SqFt

[{'date': '2024-05-25 20:05:27.402000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-05-03 08:06:46.873000', 'lowrent': '$2,950'}, {'date': '2025-05-13 00:45:44.318000', 'lowrent': 'Ask for Pricing'}]
1 Bedroom - B23

1 Bed/1.0 Bath
846 sf SqFt

[{'date': '2024-05-25 20:05:27.468000', 'lowrent': 'Ask for Pricing'}, {'date': '2024-10-08 13:13:59.063000', 'lowrent': '$2,679'}, {'date': '2024-10-19 21:44:50.185000', 'lowrent': 'Ask for Pricing'}, {'date': '2024-11-12 11:44:52.492000', 'lowrent': '$2,679'}, {'date': '2024-11-16 00:10:54.632000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-05-29 01:11:36.348000', 'lowrent': '$3,005'}, {'date': '2025-06-13 01:51:12.398000', 'lowrent': '$3,025'}]
1 Bedroom - B24

1 Bed/1.0 Bath
800 sf SqFt

[{'date': '2024-05-25 20:05:25.441000', 'lowrent': '$2,999 - $3,025'}, {'date': '2024-05-31 12:25:15.656000', 'lowrent': '$2,999'}, {'date': '2024-08-16 04:15:27.274000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-03-16 22:13:08.351000', 'lowrent': '$3,095'}, {'date': '2025-03-28 02:24:53.683000', 'lowrent': 'Ask for Pricing'}]
1 Bedroom - B26

1 Bed/1.0 Bath
925 sf SqFt

[{'date': '2024-05-25 20:05:27.681000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-03-16 22:13:08.679000', 'lowrent': '$3,045'}, {'date': '2025-04-01 14:42:03.634000', 'lowrent': 'Ask for Pricing'}]
1 Bedroom - B28

1 Bed/1.0 Bath
883 sf SqFt

[{'date': '2024-05-25 20:05:27.741000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-06-13 01:51:12.486000', 'lowrent': '$2,665'}, {'date': '2025-06-22 05:09:34.816000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-07-15 10:52:14.071000', 'lowrent': '$2,665'}]
1 Bedroom - B29

1 Bed/1.0 Bath
736 sf SqFt

[{'date': '2024-05-25 20:05:27.977000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-05-29 01:11:36.452000', 'lowrent': '$2,975'}, {'date': '2025-06-13 01:51:15.729000', 'lowrent': 'Ask for Pricing'}]
1 Bedroom - B31

1 Bed/1.0 Bath
821 sf SqFt

[{'date': '2024-05-25 20:05:28.186000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-01-03 12:39:53.123000', 'lowrent': '$2,535'}, {'date': '2025-03-16 22:13:12.974000', 'lowrent': 'Ask for Pricing'}]
1 Bedroom - B34

1 Bed/1.0 Bath
586 sf SqFt

[{'date': '2024-05-25 20:05:28.254000', 'lowrent': 'Ask for Pricing'}, {'date': '2024-08-23 06:51:08.359000', 'lowrent': '$2,560'}, {'date': '2024-10-19 21:44:48.694000', 'lowrent': '$2,650'}, {'date': '2025-03-16 22:13:13.081000', 'lowrent': 'Ask for Pricing'}]
1 Bedroom - B35

1 Bed/1.0 Bath
584 sf SqFt

[{'date': '2024-05-25 20:05:28.589000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-04-14 23:49:30.769000', 'lowrent': '$3,350'}, {'date': '2025-05-29 01:11:41.270000', 'lowrent': 'Ask for Pricing'}]
1 Bedroom - B4

1 Bed/1.0 Bath
930 sf SqFt

[{'date': '2024-05-25 20:05:28.853000', 'lowrent': 'Ask for Pricing'}, {'date': '2024-05-31 12:25:15.776000', 'lowrent': '$3,125'}, {'date': '2024-08-16 04:15:28.564000', 'lowrent': 'Ask for Pricing'}]
1 Bedroom - B6

1 Bed/1.0 Bath
925 sf SqFt

[{'date': '2024-05-25 20:05:28.921000', 'lowrent': 'Ask for Pricing'}, {'date': '2024-08-16 04:15:25.421000', 'lowrent': '$2,960'}, {'date': '2024-10-19 21:44:48.427000', 'lowrent': '$2,995'}, {'date': '2025-03-16 22:13:08.460000', 'lowrent': 'Ask for Pricing'}]
1 Bedroom - B7

1 Bed/1.0 Bath
841 sf SqFt

[{'date': '2024-05-25 20:05:25.520000', 'lowrent': '$2,495'}, {'date': '2024-08-16 04:15:28.604000', 'lowrent': 'Ask for Pricing'}]
1 Bedroom - B8

1 Bed/1.0 Bath
622 sf SqFt

[{'date': '2024-05-25 20:05:25.103000', 'lowrent': '$3,108'}, {'date': '2024-08-16 04:15:26.068000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-07-05 16:37:13.483000', 'lowrent': '$3,195'}]
1.5 Bedrooms - 411, 511, 611

1 Bed/1.0 Bath
866 sf SqFt

[{'date': '2024-05-25 20:05:25.596000', 'lowrent': '$3,815'}, {'date': '2024-10-08 13:14:02.580000', 'lowrent': 'Ask for Pricing'}]
2 Bedrooms - D3

2 Bed/2.0 Bath
1,283 sf SqFt

[{'date': '2024-05-25 20:05:25.670000', 'lowrent': '$3,865'}, {'date': '2024-08-16 04:15:29.025000', 'lowrent': 'Ask for Pricing'}]
2 Bedrooms - D4

2 Bed/2.0 Bath
1,270 sf SqFt

[{'date': '2024-05-25 20:05:24.723000', 'lowrent': '$3,950'}, {'date': '2024-08-16 04:15:25.252000', 'lowrent': '$3,895'}, {'date': '2024-09-02 05:51:58.690000', 'lowrent': 'Ask for Pricing'}, {'date': '2024-10-08 13:13:59.105000', 'lowrent': '$3,895'}, {'date': '2024-11-12 11:44:55.118000', 'lowrent': 'Ask for Pricing'}]
2.5 Bedrooms - 221

2 Bed/2.0 Bath
1,222 sf SqFt

[{'date': '2024-05-25 20:05:24.794000', 'lowrent': '$3,795'}, {'date': '2024-05-28 11:19:09.839000', 'lowrent': 'Ask for Pricing'}]
2.5 Bedrooms - 416

2 Bed/2.0 Bath
1,189 sf SqFt

[{'date': '2024-05-25 20:05:29.278000', 'lowrent': 'Ask for Pricing'}, {'date': '2024-08-23 06:51:08.175000', 'lowrent': '$3,598'}, {'date': '2024-10-08 13:14:02.321000', 'lowrent': 'Ask for Pricing'}]
2.5 Bedrooms - 516

2 Bed/2.0 Bath
1,191 sf SqFt

[{'date': '2024-05-25 20:05:25.739000', 'lowrent': '$4,295'}, {'date': '2024-08-16 04:15:25.336000', 'lowrent': '$4,295 - $4,350'}, {'date': '2025-01-03 12:39:53.043000', 'lowrent': '$4,295'}, {'date': '2025-03-16 22:13:16.246000', 'lowrent': 'Ask for Pricing'}]
3 Bedrooms - 523, 623

3 Bed/2.0 Bath
1,420 sf SqFt

[{'date': '2024-05-25 20:05:25.805000', 'lowrent': '$3,895'}, {'date': '2025-01-03 12:39:56.325000', 'lowrent': 'Ask for Pricing'}]
3 Bedrooms - 524

3 Bed/2.0 Bath
1,265 sf SqFt

[{'date': '2024-05-25 20:05:24.862000', 'lowrent': '$4,050'}, {'date': '2024-05-31 12:25:15.033000', 'lowrent': '$3,825'}, {'date': '2024-08-16 04:15:29.409000', 'lowrent': 'Ask for Pricing'}]
3 Bedrooms - 625

3 Bed/2.0 Bath
1,265 sf SqFt

[{'date': '2024-05-25 20:05:24.934000', 'lowrent': '$2,395'}, {'date': '2024-08-16 04:15:25.593000', 'lowrent': 'Ask for Pricing'}]
Efficiency - A4

0 Bed/1.0 Bath
590 sf SqFt

[{'date': '2024-05-25 20:05:26.063000', 'lowrent': 'Ask for Pricing'}, {'date': '2024-05-31 12:25:15.121000', 'lowrent': '$1,850'}, {'date': '2024-08-16 04:15:25.637000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-07-10 04:01:29.974000', 'lowrent': '$1,898'}]
Efficiency - A5

0 Bed/1.0 Bath
441 sf SqFt

[{'date': '2024-05-25 20:05:25.003000', 'lowrent': '$2,095'}, {'date': '2024-08-16 04:15:25.680000', 'lowrent': 'Ask for Pricing'}, {'date': '2024-10-08 13:13:59.237000', 'lowrent': '$2,055'}, {'date': '2024-11-12 11:44:52.760000', 'lowrent': 'Ask for Pricing'}, {'date': '2024-11-16 00:10:53.170000', 'lowrent': '$2,055'}, {'date': '2024-12-06 14:17:04.176000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-05-20 16:13:20.671000', 'lowrent': '$2,150'}, {'date': '2025-05-29 01:11:36.032000', 'lowrent': '$2,195'}]
Efficiency - A6

0 Bed/1.0 Bath
575 sf SqFt

[{'date': '2024-05-25 20:05:26.195000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-05-03 08:06:46.834000', 'lowrent': '$2,250'}, {'date': '2025-06-01 05:04:05.672000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-06-13 01:51:12.121000', 'lowrent': '$2,250'}]
Efficiency - A8

0 Bed/1.0 Bath
590 sf SqFt

[{'date': '2024-05-25 20:05:26.261000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-05-20 16:13:20.753000', 'lowrent': '$2,305'}, {'date': '2025-05-29 01:11:36.141000', 'lowrent': '$2,315'}, {'date': '2025-07-10 04:01:30.076000', 'lowrent': '$2,315'}]
Efficiency - A9

0 Bed/1.0 Bath
573 sf SqFt

[{'date': '2024-05-25 20:05:29.791000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-03-16 22:13:08.792000', 'lowrent': '$4,695'}, {'date': '2025-03-20 20:20:14.296000', 'lowrent': 'Ask for Pricing'}]
Townhouse - 101

2 Bed/1.5 Bath
1,547 sf SqFt

[{'date': '2024-05-25 20:05:29.859000', 'lowrent': 'Ask for Pricing'}, {'date': '2025-06-13 01:51:12.577000', 'lowrent': '$4,440'}]
Townhouse - 102

2 Bed/1.5 Bath
1,666 sf SqFt