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Agent Resources

Build Your Career With Winslow Homes

Now hiring licensed real estate agents and mortgage loan officers across Florida, Massachusetts, Connecticut and Rhode Island.

Reviewed and updated October 3, 2026 by Ryan and Megan Winslow, Winslow Homes

Presentation

Join Winslow Homes

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OverviewGetting StartedTools and TechnologyLead SourcesMarketingCommissionLegalMortgage PartnershipTrainingJoin Our Team
Two Paths. One Team.

Sell Homes or Finance Them

Whether you sell homes or finance them, Winslow Homes gives you the tools, support and freedom to build your business your way.

Real Estate Agent

Licensed in FL, MA, CT or RI, or license in progress. Help buyers and sellers across our four-state coverage area. Sell across four states under one brokerage and keep more of your commission. Your technology and marketing tools are included at no extra cost.

  • Rolling tier commission splits from 50/50 up to 95/5
  • Winslow CRM with automatic text and email campaigns, lead routing and an AI assistant included
  • No desk fees, franchise fees or tech fees
  • Multi-state coverage under one brokerage
  • In-house lending partnership with Ryan and Megan at The Federal Savings Bank
  • Lead generation and marketing support
  • Mentorship from experienced brokers

Mortgage Loan Officer

NMLS license, or license in progress. Guide homebuyers through the mortgage process with our in-house lending team. Originate loans through Ryan and Megan Winslow, mortgage bankers with The Federal Savings Bank, lending in all 50 states, alongside a real estate brokerage with built-in referral flow.

  • Lend in all 50 states
  • Built-in referral pipeline from brokerage agents
  • Full product suite: conventional, FHA, VA, USDA and DPA
  • Competitive compensation structure
  • Technology-driven workflow with marketing and technology support
  • Compliance and operational support
  • Dual-licensed broker leadership in real estate and mortgage
What You Get

Benefits From Day One

Every agent and loan officer receives these benefits from the start.

Full Tech Stack

Winslow CRM, lead tools and marketing platform. All included. No monthly fees.

Multi-State Reach

Operate in Florida, Massachusetts, Connecticut and Rhode Island. One brokerage. Four markets. Serve clients wherever they need you.

Transparent Splits

Floating commission structure. No hidden fees. No desk charges. Performance rewarded.

In-House Lending

Ryan and Megan Winslow on the same team. Faster closings. Better client experience. More revenue.

Training and Support

Scripts, objection handling, lead generation strategies and broker-level mentorship from day one. Ongoing education and professional development designed to accelerate your career.

Agent-First Culture

No politics. No territory fights. Your deals are your deals. We exist to help you close more of them. Flexible schedule, so you build your business your way.

Ryan and Megan Winslow
About Winslow Homes

Led by Ryan and Megan

Winslow Homes LLC is a multi-state real estate brokerage and mortgage team founded and led by Ryan and Megan Winslow. Licensed in Florida, Massachusetts, Connecticut and Rhode Island, we serve buyers, sellers and investors across the East Coast.

Our mortgage division operates through Ryan and Megan Winslow, mortgage bankers with The Federal Savings Bank, licensed to originate loans in all 50 states. Ryan NMLS 2426605. Megan NMLS 2692933.

We built this brokerage for agents who want freedom, transparency and real support. No gimmicks. No inflated promises. A straightforward place to grow your business.

Where We Operate

Licensed in Four States

Winslow Homes is licensed and actively serving clients in these markets.

Florida

Statewide coverage, with our office in New Smyrna Beach.

Massachusetts

Statewide coverage, including Central Massachusetts and Boston.

Connecticut

Statewide coverage.

Rhode Island

Statewide coverage.

How to Apply

Three Steps to Get Started

1. Fill Out the Application

Tell us about yourself on the career application page. We reply within one business day.

2. Have These Details Ready

  • Position: Real Estate Agent or Mortgage Loan Officer
  • Full name, email, phone, current city and state
  • Years of experience and license status (active, inactive, in school or pending)
  • License number and preferred state (FL, MA, CT, RI or multiple)
  • Resume link (Google Drive, Dropbox or LinkedIn)
  • How you heard about us and why you want to join

3. Talk With Ryan and Megan

We review your application and reach out to talk through your goals, your production and your starting tier. New licensees are welcome. We train.

Agents in a training session
New Licensees Welcome

New or Seasoned, We Train

We bring on licensed real estate agents and mortgage loan officers who want strong support, quality leads and real training. Whether you are new or a seasoned producer, we give you the tools and systems to close more deals.

If you hold a current license, or your license is in progress, and you want a real path to production, apply today.

Next Step

Ready to Make a Move?

Apply now or reach out with questions. We respond fast.

[email protected] | 386-690-5858 | 3539 Tuscany Reserve Blvd, New Smyrna Beach, FL 32168

Winslow Homes Publishing

Books for real estate agents by Ryan and Megan

Practical guides from 17 years and over 3,000 closings. Available on Amazon in Kindle, paperback and hardcover.

Real Estate Social Media Marketing book cover

Real Estate Social Media Marketing

Real Estate Agent Lead Generation book cover

Real Estate Agent Lead Generation

Listing Presentation Mastery book cover

Listing Presentation Mastery

Expired Listings Conversion Guide, The Property Playbook Series book cover

Expired Listings Conversion Guide, The Property Playbook Series

FSBO Conversion Playbook book cover

FSBO Conversion Playbook

Illinois Real Estate Exam Prep book cover

Illinois Real Estate Exam Prep

Apply for a mortgage

What would you keep at Winslow Homes?

Enter last year's numbers. The calculator uses the Winslow Homes rolling tier table and adds no desk, franchise or tech fees.

An estimate from your inputs. Your starting tier is set from your documented production at your previous brokerage.

Talk to Ryan, confidentially

15 minutes. Your current brokerage never hears about it.