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Careers at Winslow Homes

A Family-Run Brokerage Where Your Broker Picks Up the Phone

Built by Megan and Ryan Winslow for agents in Florida and Massachusetts. Tools made in house for agents, real training, and brokers who know you by name.

Megan Winslow, Broker Owner of Winslow Homes
Meet Your Broker

Megan Winslow

Megan Winslow is a broker and owner of Winslow Homes, and she runs the company day to day: the agents, training, transactions, compliance, listings and the mortgage side.

She specializes in luxury and high-end properties and works with an elite clientele who expect discretion, polish and results. She also leads the Winslow Homes management team.

Agents describe her the same way clients do: soft spoken, professional, warm and charming, with a sharp eye for detail and a calm hand on every deal.

Ryan and Megan Winslow
Experience You Work Beside

Led by Megan and Ryan

Winslow Homes is owned and run by Megan and Ryan Winslow themselves. There is no corporate layer between you and your broker. You call, we answer.

Megan and Ryan Winslow have been in business together for 17+ years and have sold over 3,000 homes as a team. They built Winslow Homes to give agents what most brokerages leave out: real tools, real training and a broker who picks up the phone. Ryan is U.S. Army Retired.

That experience goes into every file we review, every price we help set and every negotiation we help you win.

Tools on Day One

Your own CRM, website, portal lead connectors, listing videos, social posts and instant pricing reviews.

Training and Support

Required courses, a 90-day plan, weekly classes, one-on-one coaching and a broker who answers.

Splits and Leads

A split that moves up as you sell and never restarts with a bad year, plus leads from the website, Zillow and other portals, open houses and your sphere.

Built in House

Every Tool Is Made for the Agent

Not one of our core tools is rented vendor software that every other brokerage uses. We built them ourselves, around how agents work, with lending under the same roof.

Winslow CRM

Your contacts, leads and past clients in one place, with automatic text and email campaigns that keep every relationship warm.

An Assistant That Answers Leads

New leads get a reply in minutes, day and night. It follows up until the lead is ready, then hands them to you.

E-Sign Back Office

Open a file, fill your documents, send them for signature and track every deadline for all of your real estate documents, from your phone.

Client Reports With Your Name

Monthly home value and market reports go to your past clients, so they think of you first.

Your Own Agent Website

A Winslow Homes website with your name, your photo and your listings, tied straight into your CRM.

In-House Lending

Ryan and Megan are Mortgage Bankers with The Federal Savings Bank. Your buyers get pre-approved in house, by people you know, with one team from offer to closing.

Winslow AI on Every Page

Ask a policy, training or process question inside the CRM and back office and get an answer on the spot.

Training

140+ Courses and 570+ Lessons, Built In

Training lives inside our back office. It starts with doing things right, then teaches you to do more of them.

Compliance and Ethics

Company policies and procedures, the REALTOR Code of Ethics, fair housing in every state we serve, and escrow, deposits and wire fraud.

License Law and Contracts

Florida and Massachusetts license law, agency and disclosures, and contracts line by line from offer to closing. Connecticut and Rhode Island too.

Our Products, Step by Step

How to run the Winslow CRM every day, use the assistant, open files, fill and sign forms, track timelines and get paid in the back office.

Listings and Pricing

Comparative market analysis, winning the listing appointment, listing marketing and social media, and negotiation.

Buyers and Contract to Close

Buyer representation after the NAR settlement, writing clean offers, and managing every file from contract to closing.

Prospecting That Produces

Sphere and past clients, expired listings, for sale by owner sellers, open houses, online leads and speed to lead, farming and builder relationships.

New to the business? You start with a step by step plan for your first 90 days and one on one mentorship with your broker.

Compensation

Commission Plans That Grow With You

Pick the plan that fits your business. On the volume plan your split moves up as you sell, and the tier you earn carries into the next year instead of resetting every January.

PlanAgent / Brokerage SplitAnnual Sales Volume
Mentorship50 / 50If you closed fewer than 5 deals in the last 12 months, your first 5 deals are 50/50 while you get set up. After that you move to your tier. You work side by side with Megan and Ryan.
Tier 170 / 30Under $5,000,000
Tier 280 / 20$5,000,000 to $9,999,999
Tier 390 / 10$10,000,000 to $19,999,999
Tier 495 / 5$20,000,000 and up

Your plan, split and fees are written in your independent contractor agreement.

Tiers Do Not Restart With a Bad Year

Tiers do not restart with a bad year: your split is set by the higher of your closed volume this year or last year. Close $11,000,000 this year and you keep 90% through all of next year, even if next year runs slow. Many brokerages put every agent back on the bottom tier each January, so you pay the bigger company share again until you climb back. Here, the year you already had keeps working for you.

Move Up Right Away

Pass a tier during the year and the higher split starts on your next closing, then carries through all of next year.

Start at Your Proven Level

Coming from another brokerage? Show us your yearly volume and you start at the tier that matches it, not at the bottom.

Life Happens Protection

Family event or medical situation? Ask for a tier hold, so a hard stretch never costs you the split you earned.

Every Plan Comes With

The Winslow CRM, your own agent website, an assistant that answers your leads day and night, the e-sign back office, 140+ courses with one-on-one coaching, leads from our website and the portals, and in-house lending with Megan, so your buyers get pre-approved by people you know. You keep your name, your clients and your brand.

Getting Paid

How and When You Get Paid

Every commission is paid to you by Winslow Homes LLC, never by the title company or closing attorney.

Paid Through Winslow Homes LLC

The closing pays the brokerage, and once that wire or check clears, Winslow Homes LLC pays you. You get a notice when funds arrive and again when you are paid.

Simple Check Requests

Submit a check request in the Winslow back office after closing. Your commission is figured from your plan automatically, and payment goes out within 5 to 7 business days of closing and approval.

eChecks Deluxe Banking

Commissions arrive by electronic check at your payout email, 2 to 3 days faster than paper. No bank account numbers needed, and you deposit to any bank you like.

Clear Fees, Your Numbers

No fee per closing on the volume plan or mentorship. Team leaders pay a small overhead with no double split. Track every deal and your year to date volume in the back office.

Income calculator

What would you keep at Winslow Homes?

Enter last year's numbers, this year's projection and your current split and fees. We show which Winslow Homes plan applies, your starting tier, the math deal by deal, and what you keep compared with your current brokerage.

Deals this yearYour split at Winslow HomesYou keep
BrokerageYou keepYearly difference

Estimates for illustration only, before taxes and your own business costs. Your plan, split and fees are set in your independent contractor agreement. Apply to join or call 386-690-5858.

Winslow Homes Publishing

Books for real estate agents by Ryan and Megan

Practical guides on listings, buyers, leads and building your business. 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 Generation Guide, The Property Playbook Series book cover

Listing Generation Guide, The Property Playbook Series

New Real Estate Agent Setup Guide 2026, The Property Playbook Series book cover

New Real Estate Agent Setup Guide 2026, The Property Playbook Series

Real Estate Goal Setting Planner book cover

Real Estate Goal Setting Planner

The Feel of the Place

A Team That Feels Like Family

You Know Your Broker by Name

Ryan and Megan answer your calls and texts. Questions get a straight answer the same day.

Every File Gets a Second Set of Eyes

We review your file before closing and help with pricing, offers and tough negotiations, so you close with confidence.

Your Name, Your Clients, Your Brand

Your business stays yours. We give you the tools and support to grow it.

Your Schedule

Build your business around your life. We help you set goals and hit them.

Room to Grow

Build a Team, Bring Your People

Winslow Homes is built for agents who want more than a desk.

Teams Without the Double Split

Team leaders pay the brokerage a small overhead and run their team the way they choose. No double split between the brokerage, the leader and the agent, so the team keeps more of what it earns.

Rewards for Bringing Agents

Know a great agent? Agents who bring agents to Winslow Homes earn recruiting incentives.

A 10 Year Plan to Go Nationwide

Our goal is to take Winslow Homes nationwide over the next 10 years. Join now and grow with us into leadership as we open new markets.

Where We Work

Florida and Massachusetts

We are a family brokerage run by Megan and Ryan, serving Florida and Massachusetts and building teams as we grow into new markets. We are licensed in Connecticut and Rhode Island too.

Next Step

Start With a 15 Minute Call

Apply in two minutes. We reach out within one business day to set up a private call with Megan and Ryan. Everything stays confidential.

[email protected] | 3539 Tuscany Reserve Blvd, New Smyrna Beach, FL 32168

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