Helen Bailey Real Estate Agent - Pioneer Realty Group LLC

3440 N Lake Shore Dr Unit 12B, Chicago, IL For Sale $240,000 - listed by Helen Bailey — For Sale $240,000

Helen Bailey listing agent for 1946 W Patterson Ave Unit 3, Chicago, IL - sold for $376,000 — Sold $376,000

1949 W Cuyler Ave Unit 1, Chicago, IL For Rent $2,895/month - co-listed by Helen Bailey — For Rent $2,895/month • Co-Listing Agent

3057 N Leavitt St, Chicago, IL Pending $699,000 - listed by Helen Bailey — Pending $699,000

Helen Bailey buyer's agent for 10111 Old Orchard Ct Unit 201, Skokie, IL - sold for $142,000 — Sold $142,000

Helen Bailey

Chicago IL

Pioneer Realty Group LLC

56 Closed Sales

$23.3M Total Value

$142K - $1.4M Price Range

$416.5K Average Price

Prior 5 years

About Helen

Home Types: Condo, MultiFamily, House, Townhouse

Years of Experience: 14

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	8
Total Value	$5,445,500
Average Sale Price	$680,688
Price Range	$288K - $1.3M

Buyer Deals
Total Deals	11
Total Value	$4,096,100
Average Sale Price	$372,373
Price Range	$115K - $633K

1 Year View by Quarter

Seller Deals
Total Deals	12
Total Value	$6,507,500
Average Sale Price	$542,292
Price Range	$120K - $1.3M

Buyer Deals
Total Deals	16
Total Value	$7,105,400
Average Sale Price	$444,088
Price Range	$115K - $1.4M

2 Year View by Quarter

Seller Deals
Total Deals	20
Total Value	$8,806,500
Average Sale Price	$440,325
Price Range	$99K - $1.3M

Buyer Deals
Total Deals	36
Total Value	$14,517,800
Average Sale Price	$403,272
Price Range	$115K - $1.4M

5 Year View

Neighborhoods Helen is Experienced In

Helen's Recent Active Listings

$240,000
- 1 Bed
- 1 Bath
- 800 Sq Ft
3440 N Lake Shore Dr

Unit 12B

Chicago, IL
Lake Views from Living Room, Dining, and Bedroom! Spacious and nicely updated 1BR condo on Lake Shore Drive with unobstructed 12th-floor views of Lake Michigan and Belmont Harbor from both the living room and bedroom. This bright, well-maintained home offers generous closet space throughout and an ideal Lakeview location just steps from the lakefront, parks, restaurants, shopping, transit and

Helen Bailey Pioneer Realty Group LLC

$1,950,000
- 5,148 Sq Ft
3544 N Halsted St

Chicago, IL
Stellar location for this 6 unit multifamily in Wrigleyville! This property is comprised of three 2bed/1bath units, two 3bed/1bath units, and one 3bed/1.5 bath unit. There are three tandem parking spaces in the rear. First floor front unit has flexibility to be commercial or residential. Fully leased apartments with summer lease end dates. All units have been updated with newer kitchens and

Helen Bailey Pioneer Realty Group LLC

$2,850,000
- 6,528 Sq Ft
2120 W Belmont Ave

Chicago, IL
Fully renovated 6-unit mixed-use building located in the highly desirable Roscoe Village neighborhood. The property underwent a complete gut renovation and reconfiguration in 2020, creating modern layouts with king-sized bedrooms, added closet space, and sleek contemporary finishes throughout. Designed for low maintenance and strong tenant appeal, the building offers a stable monthly rent roll

Helen Bailey Pioneer Realty Group LLC

$699,000
- Land
- 0 Sq Ft Lot
- -- per Acre
3057 N Leavitt St

Chicago, IL
Attn Developers: Clear land ready for development. Lot available in Roscoe Village in the Jahn elementary school boundaries.

Helen Bailey Pioneer Realty Group LLC

Co-Listing Agent

$2,895 per month
- 2 Beds
- 1 Bath
- 1,193 Sq Ft
1949 W Cuyler Ave

Unit 1

Chicago, IL
Massive (1190 square foot!), first floor, two bedroom plus den apartment in prime North Center location. This building is just off Damen/Lincoln/Irving on a small, tree lined side street (Cuyler). This unit does not lack in extra space! There is a den/sun-room off of the living room, a separate living/dining room, and great bedroom sizes. The kitchen has great counter space, storage, and

Helen Bailey Pioneer Realty Group LLC

Co-Listing Agent

$2,395 per month
- 1 Bed
- 1 Bath
- 730 Sq Ft
2814 N Troy St

Unit 3R

Chicago, IL
Large, top floor, (730 square feet!) renovated 1 Bedroom apartment in Logan Square with a stainless steel kitchen + dishwasher + In Unit Laundry! Central AC/Heat and a separate living and dining room. Living space gets flooded with sunlight. There is also an enclosed back porch/sun-room for tenant's use/storage. Very easy walk to the Logan Square Blue Line, tons of restaurants, grocery stores and

Helen Bailey Pioneer Realty Group LLC

Co-Listing Agent

$1,395 per month
- 1 Bath
- 366 Sq Ft
3335 W Diversey

Unit 136

Chicago, IL
Plus sized studio (366 square feet!) with great light and lots of storage. This unit offers a ton of functional space and storage for your furniture, as well as a massive closet just off the living room. The lobby has been upgraded with an Amazon package hub recently! Cats only! Elevator building and bright/clean laundry facilities (2/load - smartphone app/card)Easy walk to the Blue Line,

Helen Bailey Pioneer Realty Group LLC

Co-Listing Agent

$2,895 per month
- 2 Beds
- 1 Bath
- 975 Sq Ft
2814 N Troy St

Unit 3F

Chicago, IL
Large, (975 square feet!) top floor, street/front facing unit. Renovated 2 Bedroom apartment in Logan Square with a stainless steel kitchen + dishwasher + In Unit Laundry! Central AC/Heat and a separate living and dining room. Living space gets flooded with sunlight - eastern and southern exposure. Very easy walk to the Logan Square Blue Line, tons of restaurants, grocery stores and neighborhood

Helen Bailey Pioneer Realty Group LLC

Co-Listing Agent

$1,450 per month
- 1 Bath
- 399 Sq Ft
3335 W Diversey

Unit 212

Chicago, IL
Huge studio (399 square feet!) with great light and lots of storage. This unit offers a ton of functional space for your furniture, as well as a massive closet that many people throw their bed in to have a true living room/bedroom separation. The lobby has been upgraded with an Amazon package hub recently! Cats only! Elevator building and bright/clean laundry facilities (2/load - smartphone

Helen Bailey Pioneer Realty Group LLC

Recently Sold

$376,000

Sold Jul 13, 2026
- 2 Beds
- 1 Bath
- 1,100 Sq Ft
1946 W Patterson Ave

Unit 3

Chicago, IL
- 16% Above List
- $342/SF
- 4 Days On Market
- Current Est. Value $412K
Helen Bailey Pioneer Realty Group LLC

$307,000

Sold Jul 2, 2026
- 2 Beds
- 1.5 Baths
- 1,175 Sq Ft
974 W 35th Place

Unit 202

Chicago, IL
- 4% Below List
- $261/SF
- 25 Days On Market
- Current Est. Value $317K
Helen Bailey Pioneer Realty Group LLC

$287,500

Sold Apr 29, 2026
- 2 Beds
- 1.5 Baths
- 1,175 Sq Ft
974 W 35th Place

Unit 302

Chicago, IL
- 3% Below List
- $245/SF
- 87 Days On Market
- Current Est. Value $290K
Helen Bailey Pioneer Realty Group LLC

$965,000

Sold Mar 20, 2026
- 2 Beds
- 2.5 Baths
- 1,786 Sq Ft
21 E Huron St

Unit 1806

Chicago, IL
- 3% Below List
- $540/SF
- 22 Days On Market
- Current Est. Value $966K
Helen Bailey Pioneer Realty Group LLC

$410,000

Sold Mar 2, 2026
- 3 Beds
- 2 Baths
- 1,500 Sq Ft
835 Judson Ave

Unit 305

Evanston, IL
- 2% Below List
- $273/SF
- 39 Days On Market
- Current Est. Value $408K
Helen Bailey Pioneer Realty Group LLC

$1,300,000

Sold Dec 9, 2025
- 8 Beds
- 4 Baths
2257 W Hirsch St

Chicago, IL
- 1% Above List
- 10 Days On Market
Helen Bailey Pioneer Realty Group LLC

$1,050,000

Sold Oct 24, 2025
- 6 Beds
- 3 Baths
- 1,159 Sq Ft
1732 W Fletcher St

Chicago, IL
- 7% Above List
- $906/SF
- Current Est. Value $1M
Helen Bailey Pioneer Realty Group LLC

$750,000

Sold Sep 30, 2025
- 5,000 Sq Ft
2423 N Long Ave

Chicago, IL
- 6% Below List
- $150/SF
- 30 Days On Market
Helen Bailey Pioneer Realty Group LLC

$230,000

Sold Jun 10, 2025
- 2 Beds
- 1 Bath
- 1,550 Sq Ft
5110 S Woodlawn Ave

Unit 2H

Chicago, IL
- 12% Below List
- $148/SF
- 35 Days On Market
- Current Est. Value $241K
Helen Bailey Pioneer Realty Group LLC

Other Experience

First Time Homebuyers, Investments, Military Families, Veteran's Programs, Luxury Homes, New Construction, Property Management, Distressed Properties, Foreclosures

Agent License: Illinois 471019249

Helen Bailey

(855) 965-4270

Pioneer Realty Group LLC

(855) 965-4270

Homes for Sale by City

Helen Bailey

About Helen

Transaction History

Seller Deals

Buyer Deals

Production Over Time

1 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

2 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Helen is Experienced In

Helen's Listings and Deals

Helen's Recent Active Listings

Recently Sold

Other Experience