U.S. Army Retired · Broker / REALTOR® · NMLS 2426605

Real estate executive with command of the entire development cycle.

For 17 years I have founded, scaled and led real estate organizations across Florida, Massachusetts, Rhode Island and Connecticut, with more than 3,000 homes sold and over $1 billion in career sales volume.

I am a licensed Real Estate Broker in four states, a Florida Certified General Contractor, a Massachusetts Construction Supervisor and an NMLS Mortgage Loan Originator. That combination gives me direct, working knowledge of land acquisition, entitlement, construction, sales, financing and closing. I have led teams of approximately 100 agents across multiple states and built Winslow Homes into an independent multi-state brokerage.

I am seeking an executive leadership role where I can apply that experience to accelerate sales, strengthen operations and scale a growing homebuilding and development organization.

Ryan C. Winslow headshot
RYAN C. WINSLOW
3,000+Homes sold
$1B+Career sales volume
$200MPeak annual sales
100+Agents led
Career timeline · select any milestone

From military service to real estate leadership

My full career history, matching my LinkedIn profile. Select any role for details.

Foundation

Raised in a real estate family

Worcester, Massachusetts

My father was a homebuilder, my mother was a real estate broker and my uncle was a mortgage lender. I learned early how construction, sales and financing depend on each other, and that understanding still shapes how I lead.

Apr 2004 to Aug 2005

Firefighter

United States Air Force · Chicopee, Massachusetts

Firefighter and emergency services specialist with the 439th Civil Engineer Squadron at Westover Air Reserve Base. I responded to aircraft, structural and medical emergencies, operated firefighting and rescue equipment, and trained in aircraft fire suppression, structural firefighting, hazardous materials and emergency rescue.

  • Responded to aircraft and structural fire emergencies, protecting personnel and critical assets.
  • Led training drills and cross-training that improved unit readiness.
  • Earned DoD Firefighter I and II, Airport Firefighter and HazMat Awareness and Operations certifications.
Aug 2005 to Aug 2009

21E Heavy Equipment Engineer Operator

United States Army · Fort Eustis, Virginia

Moved from the Air Force to the Army through the Blue to Green program. I operated and maintained bulldozers, graders, excavators and loaders to build roads, airfield runways, ammunition storage areas and defensive positions, and trained junior soldiers in safe operation and maintenance. Retired honorably in August 2009.

  • Built and maintained roads, tank trails, airstrips and protective berms supporting mission success.
  • Achieved 100% equipment readiness through preventive maintenance and timely repairs.
  • Led small teams operating heavy equipment in austere conditions.
Aug 2009 to Jun 2017

Team Leader

Winslow Homes · Worcester, Massachusetts

Built and led the Winslow Homes sales team. I mentored agents, developed sales strategies and ran daily operations while guiding buyers and sellers through every step of the transaction.

  • Built one of the leading foreclosure and distressed property listing operations in New England.
  • Represented luxury properties valued above $10 million.
  • Voted Best of Central MA for many consecutive years.
Sep 2009 to Present

Founder, Managing Partner and President of Sales and Operations

Winslow Homes · Florida, Massachusetts, Rhode Island and Connecticut

I founded Winslow Homes and built it into a multi-state brokerage and homebuilding firm. I set the strategic vision, oversee real estate sales, new home construction, land development, site work and mortgage lending, and serve as managing broker. I manage profit and loss, budgets and schedules, negotiate land acquisitions, secure permits and build partnerships with lenders, architects, engineers and subcontractors.

  • Grew annual sales volume to more than $200 million and expanded into four states.
  • Personally sold more than 3,000 homes and over $1 billion in career volume.
  • Led approximately 100 agents across multiple states and increased sales 150%.
  • Implemented CRM and AI-powered marketing to target buyers, optimize pricing and generate leads.
2014 to 2018

Bachelor of Business Administration

Southern New Hampshire University

Earned my degree with military honors while running the business full time. I am now pursuing my Master of Business Administration.

Jul 2017 to Present

Managing Broker

Winslow Homes · Massachusetts

Lead Massachusetts sales operations, contract negotiations and regulatory compliance. I provide market analysis and negotiation expertise and mentor agents. Licensed in Massachusetts since 2009.

  • Expanded brokerage and new home sales across Massachusetts and New England.
  • Built training and compliance programs aligned with Massachusetts real estate law.
  • Used AI-enabled CRM tools to improve pricing, marketing and lead conversion.
Feb 2021 to Present

Licensed Hoisting Engineer (1A, 2C)

Winslow Homes · Massachusetts

Operate and manage cranes, excavators, bulldozers and heavy equipment for residential construction and land development, including excavation, grading, site preparation and winter snow removal.

  • Completed complex excavations and foundations for custom homes and multi-lot developments with zero safety incidents.
  • Cut equipment downtime 25% through preventive maintenance and safety training.
  • Improved grading accuracy with GPS-enabled equipment and digital site plans.
Aug 2021 to Present

Licensed Construction Supervisor

Winslow Homes · Massachusetts

Manage residential and land development projects from site preparation through final occupancy, including design, permitting, inspections, budgets, schedules and subcontractors.

  • Delivered new homes and community projects with zero safety incidents and on-time completion.
  • Reduced permitting and inspection approval timelines by 20%.
  • Built vendor and trade partnerships that supported expansion across Massachusetts.
Mar 2022 to Present

Certified General Contractor

Winslow Homes · Florida

Oversee new home construction, remodels and land development in Florida from pre-construction planning to final walkthrough, including design, engineering, permitting, procurement, subcontractors, budgets, schedules and safety.

  • Built vendor and subcontractor networks across Florida that support rapid scaling.
  • Aligned construction schedules and financing programs with sales and mortgage teams.
Mar 2022 to Present

Managing Broker

Winslow Homes · New Smyrna Beach, Florida

Lead Florida sales operations, client transactions and regulatory compliance, and mentor agents across a multi-state portfolio.

  • Drove significant growth in home sales in Florida and the Southeast.
  • Streamlined contract management, permitting and inspections to shorten timelines.
  • Expanded market share with data-driven and AI-powered marketing.
Dec 2022 to Present

Managing Broker, Connecticut and Rhode Island

Winslow Homes · Connecticut and Rhode Island

Oversee licensed agents, sales operations, contract negotiations and compliance in both states while coordinating with construction and lending teams.

  • Closed residential and new home transactions with 100% client satisfaction.
  • Implemented compliance processes and digital transaction systems that reduced risk and timelines.
  • Delivered turnkey solutions with builders, architects and lenders.
Sep 2023 to Present

Author and Real Estate Training Coach

Winslow Homes Publishing · New Smyrna Beach, Florida

Founded Winslow Homes Publishing to turn 17 years of experience into practical education for agents, brokers, loan officers, contractors, investors and consumers. The catalog includes Only Sharks: How to Thrive in Real Estate and 190+ live titles.

  • Licensing and broker exam prep for all 50 states and Washington, DC.
  • Mortgage, investing, construction and consumer education guides.
  • Coaching on prospecting, listings, negotiation, lead generation and brokerage growth.
Aug 2024 to Jul 2026

Mortgage Loan Officer

Novus Home Mortgage · Remote

Guided clients from prequalification through closing and designed financing for new construction and purchase transactions.

  • Helped hundreds of families secure competitive rates and financing.
  • Implemented a digital application workflow that improved approval turnaround.
  • Created integrated financing packages with Winslow Homes that raised conversion rates.
Resilience

Rebuilding after a hurricane

Florida

A hurricane destroyed our Florida home. Megan and I kept our family steady, continued serving our clients and kept building our business. In construction, a setback means you clear the site and build again.

Jul 2026 to Present

Mortgage Banker

The Federal Savings Bank · Miami-Fort Lauderdale area

Help homebuyers, homeowners, investors and referral partners secure financing from pre-approval through closing, working alongside Megan.

  • Conventional, FHA, VA, USDA, jumbo, portfolio and Non-QM lending.
  • Financing for self-employed borrowers, investors and veterans.
  • Construction and renovation loans with multi-state support.
Today

Leading Winslow Homes across four states

Founder · Managing Broker · General Contractor · Mortgage Banker · Author

I lead Winslow Homes across Florida, Massachusetts, Rhode Island and Connecticut, directing brokerage, new home construction, remodels, excavation, site work and land development as a Florida Certified General Contractor, Massachusetts Construction Supervisor and Hoisting Engineer. I originate mortgages with The Federal Savings Bank, run Winslow Homes Publishing, coach agents and pursue my MBA while raising our three children, Jaikob, Jaelynn and Julianna. I am ready to bring this full operating experience to an executive team.

Ryan and Megan Winslow
RYAN + MEGAN
April 2004 to August 2009 · Honorable service

Leadership shaped by service

I served in both the United States Air Force and the United States Army from April 2004 until my honorable retirement in August 2009.

Military service taught me loyalty, duty, respect, selfless service, honor, integrity and personal courage. Those values are the foundation of how I lead teams, serve clients and run a business today.

U.S. Army · August 2005 to August 2009

21E Heavy Construction Equipment Operator

Operated bulldozers, graders, scrapers, loaders and excavators for grading, excavation and site preparation. Active duty with the 331st Transportation Company (Causeway), Fort Eustis, Virginia. Retired honorably.

U.S. Air Force · April 2004 to August 2005

Airman First Class, Firefighter

439th Civil Engineer Squadron, 439th Airlift Wing, Air Mobility Command, Westover Air Reserve Base, Massachusetts.

U.S. Army

Army awards

National Defense Service Medal, Global War on Terrorism Service Medal and Army Service Ribbon.

U.S. Air Force

Air Force awards

National Defense Service Medal, Global War on Terrorism Service Medal and Air Force Training Ribbon.

Honors

Presidential and Army recognition

Presidential Certificate of Appreciation, signed by the Commander in Chief. Certificate of Retirement, signed by the Chief of Staff of the United States Army.

Army training

Heavy equipment qualification

21E qualification in earthmoving, grading, excavation, backfill, slope finishing, soil stabilization and construction site safety.

Air Force training

Formal courses

Basic Military Training (6 weeks), Fire Protection Apprentice Course (13 weeks) and HAZMAT Course (6 weeks).

DoD Firefighter Certification System · IFSAC

Fire and emergency certifications

Firefighter I and II, Airport Firefighter, and HazMat Awareness and Operations under National Fire Protection Association standards, January 2006.

Texas Commission on Fire Protection

Firefighter Basic and ARFF Basic

State certifications in structural firefighting and aircraft rescue and firefighting, September 2006.

Volunteer

Wounded Warrior Project

Support fellow veterans through fundraising and community events.

Volunteer

Habitat for Humanity

Contribute construction experience and outreach to expand affordable housing.

Leicester, MA · 2019 to 2022

Chairman, Disability Commission

Led initiatives to improve accessibility and advocate for residents with disabilities.

Leicester, MA · 2019 to 2022

Elected Member, Conservation Commission

Reviewed environmental policy and land use regulations affecting local development.

2009 to present · Florida · Massachusetts · Rhode Island · Connecticut

Winslow Homes

Founder, Managing Partner, Managing Broker and President of Sales and Operations.

I built Winslow Homes into a multi-state real estate brokerage and homebuilding firm that manages sales, construction, land development and financing under one organization. I oversee profit and loss, budgets, land acquisition, permitting, vendor relationships and strategic partnerships. Megan and I built the company together, and it remains the foundation of our work today.

What began in 2009 as a Worcester, Massachusetts brokerage is now a vertically integrated company licensed in four states, with operations based in Worcester, Massachusetts and New Smyrna Beach, Florida. Every client, from a first-time buyer to a builder purchasing finished lots, works with one team that controls the entire process.

Five divisions under one roof
Real estate brokerage
Residential, luxury, new construction, investment and distressed property sales across Florida, Massachusetts, Rhode Island and Connecticut.
Homebuilding and remodels
New homes and renovations delivered under my Florida Certified General Contractor and Massachusetts Construction Supervisor licenses.
Excavation and site work
Excavation, grading, foundations, site preparation and snow removal with licensed hoisting equipment.
Land development
Land acquisition, feasibility, entitlement and finished lot sales to builders and investors.
Mortgage lending
Financing through The Federal Savings Bank that ties the loan to the sale and speeds every closing.

The company runs on four principles Megan and I set on day one: Honesty, Integrity, Trust and Service.

Ryan Winslow, founder of Winslow Homes
FOUNDER · 2009
Growth

150% sales increase

Increased sales 150% through sales training, customer engagement and expansion into new markets.

Sales performance

3,000+ homes and $1B+ in volume

Personally sold more than 3,000 homes and grew the company to $200 million in annual sales while maintaining 100% client satisfaction.

Organization scale

100 agents across multiple states

Recruited, trained and led approximately 100 agents across multiple states under Winslow Homes.

Distressed assets

Foreclosure market leader

Built one of the leading foreclosure and distressed property listing operations in New England.

Luxury

Properties above $10 million

Represented high-end and luxury properties with the discretion and marketing those clients require.

Land development

Acquire, entitle and sell lots

Identify land, manage feasibility and entitlement, and sell finished lots to builders one at a time to reduce capital tied up in inventory.

Site work

Excavation and custom homes

Built excavation, site work and custom home construction divisions, managing projects from ground preparation to final build.

Construction · CGC1532337

Zero safety incidents

As a Florida Certified General Contractor and Massachusetts Construction Supervisor, delivered quality homes on schedule with a clean safety record.

Technology

AI-driven sales and marketing

Implemented AI pricing, buyer targeting, lead generation and CRM systems that raised closing ratios and shortened sales cycles.

Recognition

Best of Central MA

Voted Best of Central MA for many consecutive years, with numerous positive client reviews on Zillow.

Professional standards

REALTOR® Code of Ethics

Completed REALTOR® Code of Ethics training and VA loan certification to serve buyers and veterans at the highest standard.

Compliance

Four-state regulatory oversight

As managing broker in Florida, Massachusetts, Rhode Island and Connecticut, I built compliance processes and digital transaction systems that reduced risk and shortened timelines.

NMLS 2426605 · Mortgage Banker · The Federal Savings Bank

Financing as a sales strategy

I treat the mortgage as part of the sale, not a step that happens after it.

Rate buydowns, closing cost structures and portfolio loan products directly affect affordability, buyer conversion and community absorption. My background as a broker and builder lets me design financing programs that move inventory while protecting margin.

As a Mortgage Banker with The Federal Savings Bank, I guide homebuyers, homeowners, investors and referral partners from pre-approval through closing. I work alongside Megan, who is also a licensed mortgage loan originator, so every client gets two experienced lenders and one clear point of contact.

Loan programs
ConventionalFHAVAUSDAJumboPortfolioNon-QMBank statementSecond homeInvestment propertyConstructionRenovationRefinance
Problems I solve
Self-employed and complex income
Structure documentation for business owners, commission earners and borrowers outside standard agency guidelines.
Veterans and active-duty military
As a retired veteran, I help service members use their VA benefit with competitive financing and clear guidance.
Investors and multiple properties
Financing strategies for rentals, second homes and clients who own several properties.
Competitive offers
Fast pre-approvals and responsive communication so buyers can write strong offers with confidence.
Jul 2026 to Present

Mortgage Banker, The Federal Savings Bank

Deliver conventional, government, portfolio and Non-QM lending with multi-state support and strong partnerships with agents, builders, attorneys and financial professionals.
Aug 2024 to Jul 2026

Mortgage Loan Officer, Novus Home Mortgage

Helped hundreds of families secure competitive financing, launched a digital application workflow that sped approvals and built integrated financing packages with Winslow Homes that raised conversion rates.
Ryan Winslow, Mortgage Banker
NMLS 2426605
For builders and developers

Incentives that sell homes

Rate buydowns and closing credit packages that raise absorption without cutting list price, timed to construction and closing schedules.

For buyers

A clear path to closing

Fast pre-approvals, side-by-side loan comparisons and plain-language guidance from application to keys.

For real estate agents

A lender who knows the deal

As a broker, I communicate the way agents need: on-time updates, strong pre-approval letters and closings that stay on schedule.

For investors

Financing that scales

Portfolio, Non-QM and investment property loans structured around cash flow and long-term portfolio growth.

Executive scope

One leader across the full development cycle

Most homebuilders rely on separate leaders for land, construction, sales, lending and marketing. I have led every one of those functions as an owner, with my own licenses and capital at stake.

That perspective lets me connect decisions across departments. I know how a permitting delay affects a closing date, how a rate buydown affects absorption and how a pricing change affects margin, because I have been accountable for all of them at the same time.

The development cycle I run · select a stage
01 · Land

Acquisition and entitlement

Source parcels, run feasibility, negotiate purchases, secure approvals and sell finished lots to builders one at a time to recycle capital faster.

Land development · Feasibility · Entitlement
02 · Site

Excavation and site work

Excavation, grading, foundations and site preparation run in-house with licensed heavy equipment, GPS-guided grading and a clean safety record.

MA Hoisting Engineer 1A, 2C · HE-198423
03 · Build

Construction management

Design, engineering, permitting, procurement, subcontractors, budgets, schedules and inspections from pre-construction to final walkthrough.

FL CGC1532337 · MA CS-116069
04 · Sell

Sales and brokerage

Recruit, train and lead sales teams, set pricing and incentive strategy and build the Realtor relationships that drive traffic and absorption.

Managing Broker · FL, MA, RI, CT
05 · Finance

Mortgage strategy

Buydowns, closing credits and portfolio loan programs designed to raise affordability and convert more buyers.

NMLS 2426605 · The Federal Savings Bank
06 · Close

Client experience

One team from contract to keys, with compliance systems that shorten timelines and keep every client informed.

100% client satisfaction
150%Sales increase
$200MPeak annual sales
20%Faster permitting
25%Less equipment downtime
How I lead
Mission first

Military discipline

Clear expectations, accountability and calm execution under pressure, learned in the Air Force and the Army.

Own the numbers

Profit and loss ownership

Budgets, margins and schedules managed as an owner for 17 years, with every decision tied to results.

Build people

Train and develop teams

Recruited and coached approximately 100 agents, with training programs that raised closing ratios and shortened cycle times.

Systems that scale

Technology and process

CRM, AI-driven marketing, digital transaction management and compliance systems that let a team grow without losing quality.

Husband and wife · Business partners

Ryan and Megan Winslow

Megan and I have built our careers side by side for 17 years.

We started in Massachusetts, expanded across New England and brought our business to Florida. Today we co-list our properties and originate mortgages together with The Federal Savings Bank, giving clients experienced brokers and lenders on one team.

Megan has built a distinguished career of her own as a licensed broker in two states and a mortgage loan originator. Her partnership has been essential to everything we have built, in business and at home with our three children.

Florida Real Estate Broker
BK3539180
Megan
Massachusetts Real Estate Broker
9581312
Megan
NMLS Mortgage Loan Originator
2692933
Megan
Partnership

Complete client service

Megan and I run our business as one team with two licensed brokers and two mortgage bankers under one roof. We co-list our properties, manage marketing and negotiations together, and originate financing through The Federal Savings Bank. Buyers, sellers, investors and builders work with one team from the first conversation through listing, construction, financing and closing. That structure removes handoffs between separate companies, shortens timelines and keeps every client informed, which is why so much of our business comes from repeat clients and referrals.

Family first

Jaikob, Jaelynn and Julianna

Our three children are the reason we work as hard as we do. When our daughters committed to competitive cheer, Megan and I moved our family and our business from Massachusetts to Florida so they could train and compete at the highest level. For the past four years we have made the long drive to South Florida week after week for practices and competitions, running a multi-state company from the road so we never missed a routine. Our son Jaikob grew up around our business and has watched it grow from the ground up. Everything we build, we build for them.

Ryan and Megan Winslow walking from a Tesla Cybertruck at a luxury listing
Winslow Homes brand film · New Smyrna Beach, Florida
Founder · Winslow Homes Publishing

192 published titles across real estate, mortgage and licensing

I founded Winslow Homes Publishing to turn 17 years of field experience into practical education for buyers, investors, agents, brokers and loan officers.

The catalog includes licensing exam prep for all 50 states and Washington, DC at both the salesperson and broker level, the SAFE Mortgage Loan Originator exam, a full library of mortgage program guides, investor strategy books and professional planners. Every title is live on Amazon in Kindle, paperback and hardcover.

Only Sharks: How To Thrive In Real EstateFlagship title · 2023Only Sharks: How To Thrive In Real EstateMy playbook for agents who want to build a lasting, high-producing business.
192Live titles
52Broker exam guides
22Mortgage guides
32Investor guides
Real estate coaching

Coaching from every side of the transaction

I have worked as a broker, brokerage owner, mortgage loan originator, general contractor and agent. My coaching draws on that experience to help agents and industry professionals build durable businesses. I show them how real estate, mortgage and construction work together, and how to turn that knowledge into additional revenue.

ProspectingListing acquisitionSales and negotiationLead generationBrokerage growthBusiness developmentTeam buildingAdditional revenue streamsReal estate, mortgage and construction integration
Licenses, certifications and education

Credentials

NMLS Mortgage Loan Originator
2426605
2024
Florida Real Estate Broker
BK3538100
2022
Massachusetts Real Estate Broker (licensed since 2009)
9581121
2017
Connecticut Real Estate Broker
REB.0794559
2022
Rhode Island Real Estate Broker
REB.0019482
2022
Florida Certified General Contractor
CGC1532337
2022
Massachusetts Construction Supervisor
CS-116069
2021
Massachusetts Hoisting Engineer (1A, 2C)
HE-198423
2021
Massachusetts Home Improvement Contractor
202862
2017
REALTOR®
Member
Active
Notary Public
Active
2009
Master of Business Administration, Southern New Hampshire University
In progress
Current
Bachelor of Business Administration, Southern New Hampshire University
Military honors
2018
Prepared for Janser Robaina · R. Homes

How my experience supports R. Homes

Since 2014, R. Homes has built a vertically integrated development platform in South Florida and set a goal of reaching $1 billion. The initiatives below are where my experience in sales, lending, construction and land development can contribute from the first day.

R. Homes Lux · 113 units

Condominium sales and absorption

Presale strategy, a Realtor co-op program and financing incentives designed to sell units before completion.

R. Homes Capital

Investor-ready execution

Owner-level profit and loss experience and lending knowledge to support capital raising and project underwriting.

Lease to Own

A clear path to mortgage approval

Credit and qualification plans that convert residents into buyers through The Federal Savings Bank.

Chloe's and Ava's Estates

Workforce housing sales

Down payment programs and rate buydowns that expand access for first-time buyers.

Land pipeline

Acquire, entitle and sell lots

Recycle capital faster by selling finished lots rather than holding land for years.

Construction

General contractor oversight

Florida CGC1532337. Schedules, budgets, inspections and quality across every community.

First 90 days

Days 1 to 30 · Assess

Learn the organization

Meet each department leader. Review the development pipeline, pricing, incentives and sales performance by community.
Days 31 to 60 · Build

Install the systems

Launch a Realtor co-op program, a lender incentive package and a CRM with weekly sales and traffic reporting.
Days 61 to 90 · Scale

Set targets and grow the team

Set absorption targets for R. Homes Lux and Ava's Estates, recruit and train sales staff, and present a 12-month growth plan.
Executive leadership · Sales leadership · Strategic partnerships

Let's discuss how I can contribute to your team

I welcome conversations about executive roles in homebuilding, development, brokerage and mortgage lending. Please reach me directly.

(774) 823-0683
Ryan C. Winslow
RYAN C. WINSLOW