The Cheshire Group

What The Cheshire Group does

The Cheshire Group is a privately held New York-based real estate investment and consulting firm founded in 1993 by Susan Hewitt. The firm operates a dual business model combining direct property investment — owning, repositioning, and disposing of underperforming residential assets across New York City's five boroughs, Westchester, Long Island, and more recently New Hampshire — with advisory and owner's-representation services to non-profits, family-owned businesses, and professionals outside of real estate. Its investment portfolio spans luxury condominium conversions (Philip House at 141 East 88th Street, Devonshire House at 28 East 10th Street), multi-family residential holdings (Kennedy House in Forest Hills, The Seville and The Versailles in Bayside), and a partnership program with 67 & Sound in Greenport on the North Fork of Long Island focused on single-family value-add acquisitions.

The firm generates revenue from two streams: property-level returns through appreciation, rental income, and disposition of owned assets, and professional services fees for advisory engagements covering transaction management, market analysis, marketing strategy, project oversight, buyouts, workouts, entitlements, and repositioning. Pricing is not publicly disclosed and is structured around bespoke engagements. Distribution is primarily direct, supplemented by the Greenport JV and referrals; the firm holds WBE (women-owned business) certification and has deep institutional ties to the New York real estate establishment, including leadership roles at the Real Estate Board of New York and the Association of Real Estate Women.

The firm is led by founder Susan Hewitt (Harvard MBA, 35+ years NYC residential market experience covering coop/condo conversions, commercial-to-residential conversions, and debt restructuring) and principal Jenifer Steig (joined 1995; Chicago Booth MBA, Cornell design background), both licensed NY real estate brokers. Headcount is 1-10 and there are no external funding rounds, institutional investors, or parent entities disclosed.

Name

The Cheshire Group

Legal name

The Cheshire Group LLC

Website

https://cheshirellc.com

Company type

Private

Founded year

1993

Operating status

Operating

Headcount range

1–10 employees

Short description

The Cheshire Group is a New York-based privately held real estate investment and consulting firm founded in 1993, specializing in revitalizing underperforming residential properties while providing owner's-representation advisory services to non-profits, family-owned businesses, and professionals outside real estate.

Ownership category

akta.pro rank

Product category

Real Estate Investment & Advisory Services

NAICS

Residential Property Managers (531311), Portfolio Management and Investment Advice (52394), Lessors of Other Real Estate Property (53119), Real Estate Property Managers (53131)

SIC

Real Estate Dealers (For Their Own Account) (6532), Real Estate Agents & Managers (For Others) (6531), Investment Advice (6282)

akta.pro primary industry

Real Estate Strategy & Portfolio Consulting (Corporate/Institutional) (BPAJANAB)

akta.pro secondary industries

Residential Real Estate Asset Management (BPAJAMAA), Real Estate Development & Feasibility Advisory (Highest-and-Best-Use, Entitlements Support) (BPAJANAC), Real Estate Advisory & Consulting (Strategy, Portfolio & Location) (FSAEAJAH)

Keywords

• Real estate investment
• Property consulting
• Value-add development
• Real estate advisory
• Residential real estate

Headquarters

HQ city

New York

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2B

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Supply Chain

Revenue model

1. Real Estate Investment: The firm invests in underperforming properties, revitalizes them, and either holds for rental income or sells for profit. Revenue is generated through property appreciation, rental income, and property sales.
2. Consulting and Advisory Services: Provides real estate strategies and solutions for non-profits and family-owned businesses, including transaction management, market analysis, marketing strategy, and project oversight.

Go-to-market motion2 records

Distribution channels2 records

Marketing channels3 records

Core offering

The Cheshire Group is a real estate investment and consulting firm that acquires and revitalizes underperforming properties across the New York metropolitan area, developing value-add opportunities in residential and multi-family real estate. The firm also provides advisory and owner's representation services to non-profits, family-owned businesses, and professionals outside of real estate, covering transaction management, market analysis, marketing strategy, and project oversight.

Product overview

The Cheshire Group operates as a unified real estate investment and consulting firm offering three integrated service pillars: (1) Direct real estate investment through property ownership and development, with a portfolio spanning luxury condominium conversions (Philip House, Devonshire House), multi-family residential investments (Kennedy House, The Seville, The Versailles), and the Greenport joint venture with 67 & Sound for Long Island home renovations; (2) Advisory services providing owner's representation, market analysis, marketing strategy, and project oversight for non-profits and family-owned businesses; and (3) Consulting on strategy, analysis, and critical real estate decisions for companies and professionals outside of real estate. The firm specializes in revitalizing underperforming properties and developing value-add opportunities throughout the New York metropolitan area.

Differentiator

Problem solved

Functional benefit

Products and services

• Advisory Services Real estate strategy and consulting services covering transaction management, market analysis, marketing strategy, and project oversight, tailored to non-profits, family-owned businesses, and professionals outside of real estate making critical real estate decisions.
• Real Estate Investment Services Investment services focused on acquiring and revitalizing underperforming residential and multi-family properties across the New York metropolitan area, including mortgage restructuring, cooperative and condominium conversions, and complex project entitlements.
• Owner's Representation Comprehensive owner's representation services covering transaction management, market analysis, marketing strategy, and project oversight for organizations making strategic real estate decisions regarding single assets or large portfolios.
• Greenport Investment Program Joint venture partnership with 67 & Sound to purchase, renovate, and hold for rent or sell well-located homes on the North Fork of Long Island, with value-add improvements to layouts, interiors, mechanicals, and landscaping.

Quantifiable outcome

• Thousands of unsold shares (cooperatives) and unsold condominiums owned and operated
• +1 more outcomes

Named customers3 records

Segments3 records

Ideal customer profiles3 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Partnerships

One partnership is on record.

• 67 & SoundcoreStrategic or Co-development PartnerThe Cheshire Group and 67 & Sound formed a partnership to purchase homes on the North Fork of Long Island. The focus is on well-located houses where they can add value through improved layouts, renovated interiors, mechanicals, and landscaping. Properties will be held for rent or sold depending on market demand.

Scale indicators3 records

Recent moves2 records

Expansion highlights4 records

Direct peers

• Taconic Investment Partners: NYC real estate investment and development firm executing value-add and opportunistic strategies. Comparable to Cheshire in its focus on revitalizing underperforming NYC assets and complex repositioning.
• Time Equities: Privately held NYC-based real estate investment, development, and management firm operating across residential, office, and mixed-use. Comparable to Cheshire as a boutique-to-mid-sized NYC principal investor and owner/operator with multi-cycle tenure.
• GFP Real Estate: Multi-generational NYC real estate investment, management, and leasing firm with a residential and commercial portfolio. Comparable to Cheshire as a family-controlled NYC operator with deep borough-level market expertise.
• Rose Associates: NYC-focused residential property management, leasing, and development firm with a long-tenured principal-led operating model. Comparable to Cheshire on NYC residential ownership, repositioning, and management.
• The Brodsky Organization: Long-tenured NYC real estate investment and management firm focused on residential and mixed-use assets. Comparable to Cheshire in its NYC-centric principal ownership model and multi-generational operating history.

Broad incumbents

• Vornado Realty Trust: Public REIT with dominant NYC office and retail portfolio. Provides a benchmark for the institutional scale Cheshire competes against for capital, tenants, and large-portfolio advisory mandates.
• Newmark Group: Global commercial real estate services firm offering investment sales, leasing, and advisory. Competes with Cheshire for owner-representation and capital markets advisory mandates from institutional NYC clients.
• JLL: Global real estate investment and advisory firm with significant NYC residential, multifamily, and capital markets presence. Direct competitor for institutional owner-representation mandates.
• Cushman & Wakefield: Global real estate services firm with deep NYC capital markets and owner-representation practice. Represents the institutional-scale competition for advisory mandates Cheshire serves.
• Related Companies: Large-scale NYC real estate developer and investment firm spanning affordable housing, luxury residential, and commercial. Overlaps with Cheshire on NYC residential development and affordable/conversion mandates.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat4 records

Key risks6 records

Key highlights6 records

Customer concentration

• LinkedInlinkedin.com/company/the-cheshire-group-llc

Compliance1 record

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 The Cheshire Group