O'Connor and Highland
O'Connor and Highland is a Greater Boston residential real estate brokerage providing buyer, seller, and rental representation under the Keller Williams franchise. Founded in 2017, the firm operates a relationship-driven model across multiple Boston neighborhoods with a team of approximately seven to eight agents.
- Company typePrivate
- Founded2017
- HeadquartersBoston, United States
- Headcount1–10
- GTM typeB2C
- OfferingServices
What O'Connor and Highland does
O'Connor and Highland is a residential real estate brokerage serving the Greater Boston market. Founded in 2017 and headquartered at 20 Park Plaza, Boston, the firm operates as an independent agent team within the Keller Williams franchise network (KW Boston Metro). It provides traditional buyer representation, seller representation, and rental services across multiple Boston-area neighborhoods including the South End, Watertown, East Boston, Somerville, Belmont, Dorchester, Jamaica Plain, Brighton, Medford, Salem, and the North Shore. The firm is co-founded and co-led by Jay Highland and John O'Connor, supported by a team of approximately seven to eight agents covering diverse specializations such as buyer-side search, estate sales, and first-time buyer support.
The service offering is a high-touch, relationship-driven brokerage model supported by a layer of digital educational resources. Core products include buying and selling representation, an All-in Monthly Cost Calculator for mortgage affordability analysis, scenario planning and decision tools, a multi-neighborhood guide library, and documented case studies. The underlying technology is a standard brokerage website with property listings, search functionality, and contact forms; no proprietary technology platform, mobile app, API, or AI/ML capabilities are identified. Marketing relies on organic social channels (Facebook, Instagram, LinkedIn, YouTube), content/SEO assets, community events, and financial education seminars. Distribution is direct agent-to-client, supplemented by self-serve website browsing and open houses, with franchise-level support from Keller Williams.
O'Connor and Highland generates revenue through traditional residential real estate commissions on buyer and seller transactions, plus rental listing fees; specific commission rates are not publicly disclosed, consistent with the industry norm of approximately 5-6% total commission split between sides. The customer base is a horizontal mix of individual residential clients — first-time buyers, move-up buyers, sellers, renters, estate representatives, and small-scale investors — with no enterprise or institutional accounts. No external private equity, venture capital, or institutional investment is evidenced, no M&A activity has been disclosed, and no patents, certifications, or formal awards are recorded in the source data.
O'Connor and Highland firmographics
Firmographics- Name
- O'Connor and Highland
- Legal name
- O'Connor and Highland
- Website
- https://oconnorandhighland.com
- Company type
- Private
- Founded year
- 2017
- Operating status
- Operating
- Headcount range
- 1–10 employees
- Short description
- O'Connor and Highland is a Greater Boston residential real estate brokerage providing buyer, seller, and rental representation under the Keller Williams franchise. Founded in 2017, the firm operates a relationship-driven model across multiple Boston neighborhoods with a team of approximately seven to eight agents.
- Ownership category
- akta.pro rank
O'Connor and Highland industry classification
Industry- Product category
- Residential Real Estate Brokerage
- NAICS
- Offices of Real Estate Agents and Brokers (531210)
- SIC
- Real Estate Agents & Managers (For Others) (6531)
- akta.pro primary industry
- Traditional Residential Brokerage (Existing Homes) (BPAJAAAA)
- akta.pro secondary industries
- Buyer Representation Services (BPAJAAAJ), Residential Investment Property Brokerage (SFR/Small Multifamily) (BPAJAAAE)
Keywords
Where O'Connor and Highland is headquartered
LocationHeadquarters
- HQ city
- Boston
- HQ country
- United States
- HQ region
- North America
Offices1 record
Markets served
O'Connor and Highland business model
Business model- GTM type
- B2C
- Offering type
- Services
- Cost components
- Personnel, Marketing or Sales, Operations, Technology or R&D
Revenue model
- Buyer and Seller Commission: Traditional real estate commission model for residential buying and selling transactions in Greater Boston. Agents represent buyers and sellers in transactions with commission splits typical of the industry.
- Rental Listings and Management: Property rental listings for residential properties across Greater Boston neighborhoods.
Pricing tiers
| Model | Billing | Price |
|---|---|---|
| Transaction based/ take rate | Multi-year contract | Buyer Representation |
Go-to-market motion1 record
Distribution channels4 records
Marketing channels8 records
O'Connor and Highland product offering
Product offeringCore offering
O'Connor and Highland is a Greater Boston residential real estate brokerage that represents clients in buying, selling, and renting homes across Boston-area neighborhoods. The firm provides end-to-end agent representation including market analysis, pricing strategy, offer negotiation, and closing support, supplemented by digital tools such as a monthly cost calculator and neighborhood guides. The brokerage operates as part of the Keller Williams (KW Boston Metro) franchise network.
Product overview
O'Connor and Highland is a Greater Boston real estate brokerage offering a unified service model centered on buying and selling representation. The core offering combines personalized agent guidance with digital tools including an All-in Monthly Cost Calculator for mortgage affordability analysis, Scenario Planning tools for comparing buying and selling options, and comprehensive Neighborhood Guides for area research. The company serves residential buyers, sellers, and investors across Boston neighborhoods including East Boston, Watertown, South End, Somerville, Salem, Belmont, and Dorchester.
Differentiator
Problem solved
Functional benefit
Products and services
- Real Estate Buying Services Comprehensive home buying representation for Greater Boston residential buyers, including buyer consultations, property search, offer strategy, and closing support. Targets individual consumers and households purchasing primary residences, move-up homes, or investment properties.
- Real Estate Selling Services Home selling services for Greater Boston residential sellers, including market analysis, strategic pricing, marketing, staging consultation, and negotiation representation. Serves individual homeowners, estate representatives, and trust liquidators.
- Residential Rental Listings Property rental listings for residential properties across Greater Boston neighborhoods, available through the firm's self-serve listings portal with filtering by price, bedrooms, location, and property type. Targets renters seeking housing in Greater Boston.
Quantifiable outcome
- Property sold with 10 offers in 2 days, under agreement in 3 days, $50,000 over asking price
- +2 more outcomes
Companies that use O'Connor and Highland
Customer profileNamed customers6 records
Segments4 records
Ideal customer profiles4 records
O'Connor and Highland technology and API
TechnologyTechnology focussed No
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
O'Connor and Highland partnerships and signals
Strategic signalPartnerships
Four partnerships are on record, tiered minor and core.
- Michael Broderick (Estate Attorney)minorEstate attorney who referred Jessica and her brothers to O'Connor and Highland for estate sale services. Represents legal/professional referral network for estate-related real estate transactions.
- Lifecycle Pro (Jason Suderman)minorEstate clean-out coordination partner who worked with O&H team on Jessica's estate sale case study. Coordinated removal and categorization of personal property.
- The Gill GroupminorCo-hosted holiday party event (Strike Up The Holiday Cheer bowling event). Joint community events and marketing activities.
- KW Boston MetrocoreFranchise affiliation providing brand, technology, training, and operational support for the O'Connor and Highland brokerage.
Scale indicators1 record
Recent moves5 records
Expansion highlights5 records
O'Connor and Highland competitors and assessment
Company assessmentBroad incumbents
- RE/MAX: Global real estate franchise with dense agent network across Greater Boston. Competes on transaction volume in the same mid-market residential segment where O&H operates.
- Compass: Tech-forward national real estate brokerage with a major Boston presence. Competes directly for Greater Boston listings and buyer representation but offers a proprietary technology platform and broader geographic reach.
- Berkshire Hathaway HomeServices: National residential brokerage franchise with multiple Greater Boston offices. Competes for the same residential buyers and sellers with broader brand reach.
- Coldwell Banker Real Estate: National brokerage franchise with substantial Greater Boston agent count. Offers residential representation across the same neighborhoods with broader brand recognition but a less relationship-led positioning.
- Sotheby's International Realty: Luxury-anchored international brokerage with Boston-area affiliates including Gibson Sotheby's. Targets higher-end residential transactions in the same neighborhoods O&H serves.
Direct peers
- Redfin: Tech-enabled residential brokerage with active Boston operations offering consumer-facing search, salaried-agent model, and rebate pricing. Represents the structural competitor to traditional boutique teams like O&H.
- Gibson Sotheby's International Realty: Greater Boston-focused luxury and residential brokerage with strong brand presence in the same neighborhoods O&H serves. Closest direct comparison in market footprint, agent-team structure, and client demographic.
- The Proper Homes Group (Compass): Boston-area boutique real estate team operating under Compass, comparable in size and relationship-led positioning. Represents the most directly analogous competitor team structure to O'Connor and Highland in the same market.
Emerging players
- eXp Realty: Cloud-based brokerage model with growing Massachusetts agent presence. Operates with significantly lower overhead and could attract agents from boutique teams like O&H while competing for similar residential clients.
Regional players
- William Raveis Real Estate: Northeast US-focused independent brokerage with significant Massachusetts presence. Competes for residential listings and buyers in suburban Greater Boston and the North Shore where O&H also operates.
Market position
Strengths5 records
Weaknesses5 records
Competitive moat3 records
Key risks5 records
Key highlights6 records
Customer concentration
O'Connor and Highland social profiles
Digital presenceO'Connor and Highland financial estimates
Financial estimateRevenue estimate
Valuation estimate
O'Connor and Highland leadership team
Management profileNumber of profiles
Profiles9 records
O'Connor and Highland funding detail
Funding detailFunding overview
Funding rounds
Investors
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
O'Connor and Highland M&A and investment
M&A and investmentM&A
Investments
M&A and investment is available on the Subscription and Enterprise plan.Contact sales →
Frequently asked questions about O'Connor and Highland
What does O'Connor and Highland do?
O'Connor and Highland is a Greater Boston residential real estate brokerage that represents clients in buying, selling, and renting homes across Boston-area neighborhoods. The firm provides end-to-end agent representation including market analysis, pricing strategy, offer negotiation, and closing support, supplemented by digital tools such as a monthly cost calculator and neighborhood guides. The brokerage operates as part of the Keller Williams (KW Boston Metro) franchise network.
Is O'Connor and Highland a public or private company?
O'Connor and Highland is a private company. It is classified as founder individual operated bootstrapped and is currently operating.
When was O'Connor and Highland founded?
O'Connor and Highland was founded in 2017. It employs 1 to 10 people.
Where is O'Connor and Highland based?
O'Connor and Highland is headquartered in Boston, United States, in the North America region.
How does O'Connor and Highland make money?
Two revenue lines are on record. Buyer and Seller Commission is the primary driver. The others are rental Listings and Management.
Who are O'Connor and Highland's main competitors?
Broad incumbents on record are RE/MAX, Compass, Berkshire Hathaway HomeServices, Coldwell Banker Real Estate and Sotheby's International Realty. Direct peers are Redfin, Gibson Sotheby's International Realty and The Proper Homes Group (Compass). eXp Realty is listed as an emerging player. William Raveis Real Estate is listed as a regional player.
Does O'Connor and Highland have an API?
No public API is recorded for O'Connor and Highland.
What industry is O'Connor and Highland in?
O'Connor and Highland's product category is Residential Real Estate Brokerage. Its primary akta.pro industry code is BPAJAAAA, Traditional Residential Brokerage (Existing Homes), with a secondary code of BPAJAAAJ, Buyer Representation Services. Its NAICS code is 531210 and its SIC code is 6531.