Drakeley Real Estate

What Drakeley Real Estate does

Drakeley Real Estate is a privately held, family-owned real estate brokerage founded in 1986 by Joyce S. Drakeley and headquartered at 256 Main Street S in Woodbury, Connecticut. The firm provides residential, land, and commercial sale and rental services across 16 Connecticut towns spanning Litchfield, Fairfield, and New Haven counties, with active listings ranging from approximately $59,900 land parcels to $7,250,000 estates. The brokerage is currently led by second-generation owner and lead broker Tim Drakeley alongside his wife Shelley Drakeley, supported by a roster of 12 licensed agents including Joyce Drakeley (broker since 1974), Matthew Amatruda, MaryAnn Bennett, Jeffrey Boucher, Chuck Cosgriff, Taylor Hamel, Josh Harwood, Katherine Parlato, Rhonda Stokes, and Rhya Szymansky.

The company's core technology stack is a WordPress-based website using the Estatik plugin for property listings, supplemented by free online calculator tools (Home Sale Calculator, Mortgage Calculator, Affordability Calculator) and a third-party hifello.com integration for home valuation lead capture. The product surface includes a property search platform with filters for price, bedrooms, bathrooms, type, and lot size; an agent directory; and a local area exploration guide. Distribution is primarily agent-driven across the 16-town footprint, with digital marketing through the company website, email newsletter, social media, and Google Reviews.

The firm earns revenue through real estate commissions on buy-side and sell-side transactions across residential, commercial, land, and rental categories. Commission rates are not publicly disclosed. The brokerage benefits from cross-affiliated businesses owned by the leadership — Tim Drakeley Old Barns and Drakeley Construction — which generate organic listing pipeline and provide hands-on expertise in historic properties, renovations, and new construction that differentiates the firm's advisory capability. The company operates as an independent, family-controlled entity with no external investors, parent company, or institutional funding.

Name

Drakeley Real Estate

Legal name

Drakeley Real Estate, Inc.

Website

https://drakeley.com

Company type

Private

Founded year

1986

Operating status

Operating

Headcount range

11–50 employees

Short description

Drakeley Real Estate is a privately held, family-owned real estate brokerage founded in 1986 in Woodbury, Connecticut, serving 16 towns across Litchfield, Fairfield, and New Haven counties with residential, land, and commercial sale and rental services through a team of 12 agents.

Ownership category

akta.pro rank

Product category

Residential Real Estate Brokerage

NAICS

Offices of Real Estate Agents and Brokers (531210), Offices of Real Estate Agents and Brokers (5312)

SIC

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

akta.pro primary industry

Traditional Residential Brokerage (Existing Homes) (BPAJAAAA)

akta.pro secondary industries

Residential Investment Property Brokerage (SFR/Small Multifamily) (BPAJAAAE), Investment Sales Brokerage (BPAJABAI), Recreational Land Brokerage (Hunting, Fishing, Wildlife) (BPAJADAD)

Keywords

• Residential real estate brokerage
• Property listing services
• Buyer representation
• Seller representation
• Commercial real estate

Headquarters

HQ city

Woodbury

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

Revenue model

1. Real Estate Commissions: The company earns commissions on buy-side and sell-side residential and commercial real estate transactions. Services include representing buyers, sellers, and investors across Connecticut. The brokerage handles the full transaction lifecycle from market analysis and marketing to negotiation and closing.

Go-to-market motion1 record

Distribution channels2 records

Marketing channels4 records

Core offering

Drakeley Real Estate is a family-owned real estate brokerage that represents buyers, sellers, and investors in residential, commercial, and land transactions across Connecticut. The firm delivers full-lifecycle brokerage services — including market analysis, strategic marketing, negotiation, and closing support — through 12 licensed agents operating from its Woodbury office and covering 16 Connecticut towns.

Product overview

Drakeley Real Estate is a family-owned Connecticut real estate brokerage offering a web-based property search platform as its core product, complemented by a directory of affiliated agents and several free online calculator tools (Home Sale Calculator, Mortgage Calculator, Affordability Calculator). The platform enables buyers and sellers to search residential and commercial listings across multiple Connecticut towns, with additional resources for local area exploration. The company integrates third-party home valuation and cash offer services via external providers for lead generation purposes.

Differentiator

Problem solved

Functional benefit

Products and services

• Residential Property Brokerage Services Full-lifecycle residential real estate brokerage: buyer representation, seller representation, market analysis, strategic marketing, negotiation, and closing support for single-family homes, condominiums, and multi-family properties across Litchfield County and surrounding Connecticut towns. Targeted at individual homebuyers and sellers.
• Commercial Real Estate Brokerage Services Buyer and seller representation for commercial properties, including commercial for sale, commercial for lease, and business-for-sale listings. Aimed at investors and business owners acquiring or divesting commercial assets in Connecticut.
• Land Sales Brokerage Services Buyer and seller representation for lots and land, including rural parcels and development tracts, with listing prices observed ranging from approximately $59,900 to $525,000+ across Connecticut towns such as Morris and Kent.

Segments3 records

Ideal customer profiles3 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Scale indicators2 records

Recent moves5 records

Expansion highlights3 records

Direct peers

• William Pitt Sotheby's International Realty: Largest luxury-focused brokerage in Connecticut with deep presence in Litchfield and Fairfield Counties. Directly competes for high-end buyers and sellers in the same towns Drakeley serves, with similar estate and historic property expertise.
• Klemm Real Estate: Family-owned Litchfield County brokerage with similar historic, estate, and country property focus. Direct competitor in the same Connecticut geography with comparable boutique service model.
• Elyse Harney Real Estate: Independent Connecticut brokerage specializing in Litchfield County luxury, historic, and country properties. Closely comparable boutique competitor serving the same affluent buyer pool.
• Houlihan Lawrence: Large Connecticut-area brokerage with strong presence in Litchfield and Fairfield County luxury segments. Directly comparable service model and geographic footprint for premium residential transactions.

Broad incumbents

• William Raveis Real Estate: Family-founded regional brokerage headquartered in Connecticut with broad coverage across Litchfield, Fairfield, and New Haven Counties. A scaled competitor with overlapping geography and a wider portfolio of services.
• Berkshire Hathaway HomeServices New England Properties: National brand with substantial Connecticut franchise network across Litchfield, New Haven, and Fairfield Counties. Offers overlapping residential brokerage services backed by brand and tech resources.
• Coldwell Banker Realty: National brokerage franchise with extensive Connecticut coverage. Competes for the same residential listings and buyers in Litchfield County with a larger marketing and technology footprint.
• Compass: Tech-forward national brokerage expanding aggressively into Connecticut's affluent suburbs. Represents a structural threat to traditional brokerages like Drakeley via proprietary platform, agent recruitment, and modern marketing.

Emerging players

• eXp Realty: Cloud-based brokerage model attracting independent agents with high commission splits and low overhead. Emerging competitive threat to traditional brick-and-mortar firms like Drakeley for agent recruitment and listings.
• Redfin: Tech-enabled brokerage offering lower-commission and salaried-agent models nationally, including parts of Connecticut. Represents the iBuying/flat-fee disruption pressure bearing on traditional commission-based brokerages.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat3 records

Key risks6 records

Key highlights6 records

Customer concentration

• LinkedInlinkedin.com/company/joyce-drakeley-real-estate

Revenue estimate

Valuation estimate

Number of profiles

Profiles12 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 Drakeley Real Estate