What Big Shoulders Realty does

Big Shoulders Realty is a privately held, two-agent residential real estate brokerage operating in Chicago, Illinois, incorporated in Illinois with its office at 825 Chicago Avenue, #C-5, Evanston, following a 2025 relocation from a prior 19-year Jefferson Park location. Founded circa 2006 by Lee Diamond (Broker) and Carrie Weston (Realtor), the firm employs 1-10 people and is run as an independent partnership with no disclosed institutional backing, parent company, or acquisitions.

The brokerage delivers traditional buy-side and sell-side residential representation across the Chicago metropolitan area, including first-time buyer advisory, mortgage-fintech integration via Lee Diamond's dual mortgage/realty expertise, and a distinctive bicycle-based property showing channel operated through Lee Diamond's adjacent Chicago Velo / Chicago Neighborhood Bike Tours venture. Its product surface consists of agent-guided search, MLS access through an IDX Broker integration, neighborhood-keyed listing pages covering all 110 Chicago community areas, and architectural-style educational resources. Underlying technology is conventional for the category: MLS data via IDX Broker, standard real estate transaction management, and a WordPress-based content site. There is no proprietary platform, no AI/ML features, and no app.

Revenue is generated entirely from residential real estate commissions on completed transactions, charged as a take rate against sale price and split between listing and buyer agents per market convention. Specific commission rates are not publicly disclosed. Customer acquisition relies primarily on word-of-mouth referrals reinforced by earned media coverage in Chicago outlets (Curbed Chicago, Chicago Tribune, Time Out Chicago, DNAinfo) and experiential marketing via bike tours. The company reports having served hundreds of families since inception across Chicago and the greater metropolitan area.

Name

Big Shoulders Realty

Legal name

Big Shoulders Realty

Website

https://bigshouldersrealty.com

Company type

Private

Founded year

2002

Operating status

Operating

Headcount range

1–10 employees

Short description

Big Shoulders Realty is a privately held, two-agent Chicago-based residential real estate brokerage serving individual homebuyers and sellers across the Chicago metropolitan area, with distinctive bicycle-tour property showings and integrated mortgage guidance.

Ownership category

akta.pro rank

Product category

Residential Real Estate Brokerage

NAICS

Offices of Real Estate Agents and Brokers (5312), Offices of Real Estate Agents and Brokers (53121)

SIC

Real Estate Agents & Managers (For Others) (6531)

akta.pro primary industry

Traditional Residential Brokerage (Existing Homes) (BPAJAAAA)

akta.pro secondary industries

Seller Representation & Listing Services (BPAJAAAK), Buyer Representation Services (BPAJAAAJ)

Keywords

• Residential real estate brokerage
• Home buyer representation
• Home seller representation
• MLS property search
• Bicycle property tours

Headquarters

HQ city

Chicago

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Technology or R&D

Revenue model

1. Real Estate Commission: Traditional real estate brokerage earning commissions on residential property transactions. Agents handle both buyer and seller representation, including dual agency when appropriate.

Pricing tiers

Go-to-market motion2 records

Distribution channels1 record

Marketing channels6 records

Core offering

Big Shoulders Realty is a Chicago-area residential real estate brokerage providing buyer representation and seller representation, supported by MLS-based property search (via IDX Broker), neighborhood-specific listing pages for all 110 Chicago neighborhoods, and signature bicycle-led property tours of neighborhoods through its affiliated Chicago Velo tour operation. The brokerage is run by two principal agents (Lee Diamond and Carrie Weston) who also offer mortgage expertise, first-time buyer guidance, and tailored services for families with special needs.

Product overview

Big Shoulders Realty is a small Chicago-based residential real estate brokerage offering a unified platform of property buying and selling services. The core offering consists of agent-guided home buying and selling services delivered by two principal agents (Lee Diamond and Carrie Weston), supported by multiple property search tools including traditional MLS search, neighborhood-based listings across Chicago's 110 communities, and unique search-by-bike tours. The company also provides educational resources on architectural styles and neighborhoods. All services are delivered through direct agent relationships rather than a self-service digital platform.

Differentiator

Problem solved

Functional benefit

Products and services

• Buy A Home Services Residential home buying services for individual consumers in the Chicago metropolitan area, including agent-guided property searches, MLS database access, and neighborhood-based listing searches across Chicago's 110 neighborhoods.
• Sell A Home Services Home selling assistance for individual residential property owners, including marketing, pricing strategy, and full transaction support for residential properties in the Chicago metropolitan area.
• Search by Bike (Bicycle Property Tours) A signature property search service in which prospective homebuyers explore Chicago neighborhoods via bicycle tours led by Broker Lee Diamond, allowing buyers to experience neighborhoods firsthand while viewing prospective properties.
• Lee Diamond Broker Services Personal broker services from Lee Diamond specializing in historic preservation, first-time buyers, mortgage financing, and assistance for families with special needs including wheelchair accessibility assessments.
• Carrie Weston Realtor Services Residential real estate agent services from Carrie Weston with extensive knowledge of Chicago neighborhoods, housing construction styles, market conditions since 2002, and a creative marketing and negotiation approach.

Quantifiable outcome

• Served hundreds of families

Named customers4 records

Segments5 records

Ideal customer profiles4 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration1 record

Feature1 record

Partnerships

One partnership is on record.

• Chicago VelominorGTM or Marketing PartnerLee Diamond operates Chicago Velo (www.chicagovelo.com), a website and series of architectural bike tours of Chicago called the Chicago Neighborhood Bike Tours. This partnership generates community engagement and marketing for the realty business through experiential neighborhood exploration.

Scale indicators4 records

Recent moves5 records

Expansion highlights3 records

Broad incumbents

• Redfin: Tech-enabled residential brokerage operating in the Chicago metro with a discount, high-volume model. Competes for the same Chicago buyer pool but with a fundamentally different cost structure and self-service digital platform.
• Coldwell Banker: Major national residential real estate franchise with strong Chicago agent network. Provides overlapping traditional brokerage services but at national scale, with brand and marketing resources well beyond Big Shoulders' capacity.
• RE/MAX: Globally recognized residential real estate franchise with deep Chicago metro penetration. Provides comparable residential brokerage services through independent contractor agents, though at a much larger scale than Big Shoulders' two-agent operation.
• Compass: National technology-driven residential brokerage with significant Chicago presence. Overlaps with Big Shoulders in serving Chicago buyers and sellers but operates at vastly greater scale with proprietary platform tools.
• Keller Williams Realty: Largest residential real estate franchise by agent count in the U.S., with established Chicago presence. Comparable in offering agent-led residential brokerage services but competes through massive agent network and training infrastructure.
• Berkshire Hathaway HomeServices: National residential brokerage franchise with Chicago metro operations. Offers traditional full-service residential representation comparable to Big Shoulders but with global brand backing and far broader geographic reach.

Emerging players

• eXp Realty: Cloud-based residential brokerage with growing Chicago presence, operating on a commission-cap model that appeals to independent agents. Competes for the same independent-agent talent pool and buyer/seller relationships, representing a structural alternative to traditional boutique models like Big Shoulders.

Direct peers

• Baird & Warner: Long-standing Chicago-area independent brokerage operating a traditional agent-driven residential model. Comparable in market focus (Chicago metro) and reliance on local expertise, though at meaningfully larger scale than Big Shoulders.
• @properties: Chicago-based residential brokerage founded in 2000 and one of the largest independent brokerages in the metro area. Directly comparable as both serve Chicago buyers and sellers through agent-driven brokerage, with @properties representing a scaled-up version of Big Shoulders' model.
• Dream Town Realty: Chicago-focused independent residential brokerage with deep neighborhood expertise and agent-led service model. Closely comparable to Big Shoulders in geography, boutique positioning, and reliance on neighborhood-specific knowledge as a differentiator.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat3 records

Key risks6 records

Key highlights7 records

Customer concentration

• Facebookfacebook.com/BigShouldersRealty

Compliance2 records

Revenue estimate

Valuation estimate

Number of profiles

Profiles2 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Big Shoulders Realty