Cromwell, Connecticut

Real Estate Guide, Market Trends & Community Living

Market Quick Stats

Population
14,416
Median Home Price (May 2025)
$340,000
Median Household Income
$110,596
Property Tax Rate
2.94%
Median Age
43.5 years
Home Ownership Rate
80.3%

About Cromwell, Connecticut

Cromwell is a thriving community in Middlesex County, Connecticut, home to 14,416 residents. The town sits along the west bank of the Connecticut River and combines suburban convenience with small-town charm. With a strong sense of community, excellent schools, and convenient access to Hartford and New Haven, Cromwell attracts families, professionals, and retirees seeking a balanced lifestyle.

The median household income of $110,596 reflects a stable, affluent community with well-educated residents. The town maintains an 80.3% home ownership rate, indicating strong residential investment and neighborhood stability. Cromwell's diverse economy includes insurance, healthcare, manufacturing, and retail sectors, providing varied employment opportunities for local residents.

Known for its cultural amenities, recreational opportunities, and historic charm, Cromwell offers everything from fine dining at upscale restaurants to outdoor activities on the Connecticut River. The town's central location within the state makes it ideal for commuters working in Hartford, New Haven, or elsewhere across Connecticut.

Housing Market Overview

The Cromwell real estate market shows strength with median home prices at $340,000 as of May 2025, up 16.4% from the prior year. The median price per square foot stands at $217, and homes sell quickly in this seller's market. Recent data indicates 65.2% of homes sold above asking price, reflecting strong buyer demand and limited inventory.

Neighborhoods & Areas

🏘️ Riverport (Downtown)

Cromwell's traditional downtown district features Main Street (Route 99) with independently owned businesses, restaurants, pubs, and personal services. The historic Riverport showcases a tea room, antique shops, and art studios alongside two beautiful riverfront parks perfect for recreation and relaxation.

🏘️ Northern Gateway

The northern section of Main Street serves as Cromwell's gateway, highlighted by the PGA's Travelers Championship and Tournament Players Country Club (TPC). This area blends residential character with world-class golf and tournament facilities.

🏘️ Route 372 Corridor

The Route 372 corridor offers commercial vitality with multiple shopping centers, restaurants, office complexes, and four hotels including the Crowne Plaza Hotel and Conference Center, Courtyard by Marriott, Super 8, and Comfort Inn. National retailers and dining chains provide convenient shopping and hospitality services.

🏘️ Evergreen 55+ Community

An active adult community designed for residents 55 and older, featuring comprehensive amenities and services tailored to active retirees seeking a vibrant lifestyle.

🏘️ Town Center & North Cromwell

A rural neighborhood offering quiet residential character with tree-lined streets and spacious properties for families seeking a suburban feel close to town services.

Property Types Available

🏡 Single-Family Homes

Single-family detached homes dominate Cromwell's residential landscape at 57.8% of the housing stock. These range from charming colonial estates in downtown areas to contemporary homes on spacious suburban lots. Prices typically start around $340,000 and extend well beyond $450,000 for premium properties.

🏢 Condominiums

Condominium communities offer lower maintenance and an entry point for first-time homebuyers. Options range from urban condos near downtown to suburban condo communities with shared amenities and landscaping services.

🏘️ Rental Properties & Investments

Multi-unit properties and rental homes present strong investment opportunities in this appreciating market. The 16.4% year-over-year appreciation demonstrates solid equity growth potential for investors.

🏘️ Land & Development

Vacant lots and development parcels are available for builders and developers seeking growth opportunities in this expanding market.

Schools & Education

The Cromwell School District serves 1,904 students with an above-average public school system. The district maintains a student-teacher ratio of 12 to 1, and averages rank 6 out of 10 in Connecticut with math proficiency at 48% and reading proficiency at 56%.

🎓 Cromwell High School

Cromwell High School ranks 41st out of 145 Connecticut high schools with a 4-star rating. The school boasts an 88.4% four-year graduation rate and outperforms state averages in SAT/ELA and SAT/Math proficiency, indicating strong academic rigor and student success.

🎓 Cromwell Middle School

Cromwell Middle School ranks 74th out of 252 Connecticut middle schools with a 4-star rating. The school demonstrates high proficiency rates in SBAC/ELA, SBAC/Math, and NGSS/Science, exceeding state averages in core academic areas.

🎒 Elementary Schools

Edna C. Stevens School and Woodside Intermediate School serve younger students. Both schools contribute to the district's solid academic foundation and comprehensive K-12 educational experience.

🎓 Note on Attendance

The district addresses a chronic absenteeism rate of 17.7%, which exceeds the state target of 10%. Families should work with school administration to ensure consistent attendance for academic success.

Lifestyle & Community

Life in Cromwell balances suburban convenience with vibrant community engagement. The town offers year-round recreational activities, cultural events, and outdoor experiences that appeal to families, professionals, and retirees.

🎣 Recreation & Parks

The Cromwell Recreation Department operates extensive programs including sports leagues, instructional athletics, fitness classes, music lessons, arts and crafts, and summer concerts. Outdoor recreation includes kayaking on the Mattabassett River, with round-trip routes to the Connecticut River mouth spanning approximately 8 miles. River Highlands State Park provides hiking, scenic overlooks, and natural habitat preservation.

🌴 Community Events

The Cromwell Riverport Festival celebrates town spirit and local culture annually. The Town of Cromwell Farmers Market operates Friday evenings from 4 to 7 p.m. at Riverport Park during summer months, featuring farm-fresh vegetables, locally sourced products, artisans, food trucks, and live music.

🎨 Arts & Culture

Cromwell Arts Alliance supports creative culture with opportunities in dance, theater, painting, writing, music, and multimedia. The organization develops and facilitates arts participation for citizens of all ages, strengthening community cultural appreciation.

Dining & Restaurants

Cromwell offers diverse dining options from casual neighborhood spots to upscale establishments showcasing local and international cuisine.

🍽️ Featured Restaurants

Downtown Main Street features additional dining establishments, pubs, and cafes offering casual and fine dining experiences.

Commute & Transportation

Cromwell's central location within Connecticut provides convenient commuting options to major employment centers throughout the state.

🚗 Hartford

Located approximately 14 miles north, Hartford is accessible via car in approximately 21 minutes. Public transportation via line 55 bus takes 39 minutes and costs $1 to $4. Hartford's central business district hosts corporate headquarters, insurance companies, and government offices.

🚗 New Haven

New Haven sits approximately 28 miles south, with a driving time of 37 minutes. This coastal city houses Yale University, medical institutions, and corporate offices. Bus service requires transfers and takes approximately 2 hours 44 minutes.

🚗 Local Transportation

Cromwell maintains CTtransit express services providing regional bus connectivity. Route 99 (Main Street) and Route 372 provide primary vehicle access through town.

Cost of Living

Cromwell's 2026 cost of living reflects a suburban Connecticut community. For a single person, monthly costs run $2,979, while a family of four averages $6,560 monthly. Overall living costs are approximately 20% higher than the U.S. national average and 70% higher than Connecticut's state average.

🛒 Housing Costs

Housing expenses are 2.9% higher at approximately $1,234 per month for a single person and $2,263 for a family of four. Housing in Cromwell ranks more expensive than the national average but reflects the community's quality and desirability.

🛒 Utilities & Living Expenses

Energy, transportation, and healthcare costs average 2.3% higher at approximately $895 monthly for individuals and $1,994 for families. Throughout the year, Cromwell receives 162.2 rainfall days and 34.13 inches of precipitation, with annual snowfall of 14.76 inches across 29.4 days.

Property Tax Information

Property taxes in Cromwell are set annually by the Board of Finance and the Fire District Commission. Understanding tax obligations is crucial for budgeting and financial planning when purchasing Connecticut real estate.

💵 2024 Mill Rates

The current mill rates for the 2024 Grand List are 27.33 for the Town and 3.46 for the Fire District, totaling 30.79 mills. This equates to approximately $29.41 in taxes per $1,000 of net assessed value.

💵 Effective Tax Rate

Cromwell's median effective property tax rate is 2.94%, significantly higher than the national median of 1.02%, though lower than Connecticut's state median of 3.14%. The median annual tax bill is $5,599 for Cromwell homeowners.

💵 Tax Payment Schedule

Real estate, personal property, and motor vehicle tax bills are due July 1 annually and become delinquent after August 1. The Town of Cromwell Tax Collector's office manages all tax billing and payment processing.

Flood Zones & Natural Hazards

Cromwell participates in the National Flood Insurance Program (NFIP) and maintains detailed flood zone mapping through FEMA Flood Insurance Rate Maps (FIRMs). Understanding flood risk is essential for property buyers and insurance planning.

🌊 FEMA Flood Zones

Flood zones identify land areas subject to flooding and are classified as Special Flood Hazard Areas (SFHA). These high-risk areas would be inundated by the 100-year flood, also called the base flood. The Town of Cromwell provides individual Flood Zone Maps accessible through the town GIS site, with FEMA flood firmwares and zones available through the Themes menu.

📋 Flood Insurance

Properties located in designated flood zones require flood insurance through the National Flood Insurance Program. Lenders mandate this coverage for mortgaged properties in high-risk areas. Connecticut residents can access official flood maps through the FEMA Flood Map Service Center.

🌊 River Proximity

Located on the west bank of the Connecticut River, some Cromwell properties face elevated flood risk during high water events. Buyers should verify flood zone status before purchasing and factor insurance costs into overall housing expenses.

Real Estate Investment Analysis

Cromwell presents compelling investment opportunities with demonstrated market strength. The 16.4% year-over-year appreciation and 65.2% of homes selling above asking price indicate strong buyer demand, limited supply, and positive price momentum.

💰 Rental Market

With 19.7% of housing units rented, Cromwell offers rental income opportunities. The proximity to employment centers in Hartford and New Haven attracts renters seeking suburban living with urban access. Multi-unit properties command strong rental rates and steady tenant demand.

💰 Long-Term Value

Cromwell's combination of quality schools, cultural amenities, employment diversity, and Connecticut River proximity positions the town for sustained appreciation. The community's stability and amenities attract multiple demographic groups, supporting steady demand across economic cycles.

First-Time Homebuyers Guide

Cromwell welcomes first-time homebuyers with various assistance programs and financing options. Connecticut Housing Finance Authority and community resources provide education and financial support for qualified buyers.

🏘️ Down Payment Assistance Programs

Connecticut Housing offers two primary down payment assistance programs. The Time To Own program provides 0% interest forgivable loans to first-time homebuyers, offering up to $50,000 in high-opportunity areas or $25,000 in other locations. Participation requires completing a homebuyer education course and using a CHFA-approved lender.

🏘️ Mortgage Programs

Connecticut Housing Finance Authority's HFA Advantage and HFA Preferred programs offer lower mortgage insurance premiums. The Homebuyer Mortgage Program provides below-market interest rates and access to down payment assistance for qualified borrowers.

🏘️ Housing Counseling Services

Community Renewal Team (CRT) provides housing counseling throughout Cromwell's service area. Counselors work with lenders, help lower monthly payments, explain options, assist with applications, and monitor the mortgage process. Call CRT at 860-761-2381 for more information.

🏘️ Novus Home Mortgage Support

Novus Home Mortgage is a federally licensed lender offering loan products nationwide via NMLS. Ryan (NMLS 2426605) and Megan (NMLS 2692933) are available to discuss first-time buyer options, down payment assistance, and competitive mortgage rates.

Relocating to Cromwell

Cromwell attracts residents relocating from across the nation seeking Connecticut's cultural, educational, and economic advantages. The town offers excellent schools, diverse employment, and quality of life for professionals, families, and retirees.

🏘️ Moving Considerations

When relocating to Cromwell, research school districts if you have children, identify employment opportunities, and explore neighborhoods matching your lifestyle preferences. The Riverport downtown offers walkable shopping and dining, while suburban areas provide spacious properties and quiet living.

55+ Active Adult Living

Cromwell welcomes active adults 55 and older with purpose-built communities offering comprehensive amenities, social activities, and maintenance-free living.

🏘️ Evergreen Community

Evergreen is a premier 55+ active adult community in Cromwell offering residences designed for active lifestyles. Amenities include clubhouses, fitness facilities, organized social activities, and maintenance services freeing residents to pursue hobbies and travel.

🏥 Healthcare Access

Cromwell residents enjoy proximity to quality healthcare. Middlesex Hospital Primary Care at 80 Shunpike Road offers family medicine services Monday through Friday. Hartford HealthCare-GoHealth Urgent Care at 28 Shunpike Road provides evening, weekend, and holiday hours. Autumn Lake at Cromwell offers advanced care programs for complex medical conditions with in-house board-certified specialists.

Employment & Job Market

Cromwell's diverse economy provides varied employment opportunities across multiple sectors. The town is home to approximately 2,759 active job openings across 15 industries.

📈 Job Market Overview

Cromwell's vibrant small business scene offers diverse career options in insurance, finance, healthcare, manufacturing, and service sectors. The proximity to Hartford's corporate headquarters and New Haven's professional services creates expanded employment opportunities for commuters.

Utilities & Services

Cromwell residents enjoy reliable municipal and private utilities supporting residential and commercial needs.

🏘️ Electricity & Gas

Eversource Energy provides natural gas and electric service throughout Connecticut. Residents should contact Eversource for service inquiries, billing, and energy efficiency programs.

🚤 Water & Sewer

The Town of Cromwell provides public water and sewer services to residential and commercial properties. The Public Works Department manages infrastructure maintenance and customer service. Some outlying areas rely on private wells and septic systems.

🏘️ Internet & Communications

Multiple internet service providers operate in Cromwell, including cable, fiber, and satellite options. Residents should verify service availability at specific addresses when considering properties.

🏘️ ⚡ Utility Costs

Monthly utility costs average $895 for individuals and $1,994 for families, approximately 2.3% higher than national averages. Heating costs increase during winter months when temperatures reach average lows of 22 degrees Fahrenheit.

Weather & Climate

Cromwell experiences four distinct seasons with warm summers, very cold snowy winters, and pleasant spring and autumn transitions. Over the year, temperatures vary from 21 degrees Fahrenheit to 83 degrees Fahrenheit and rarely fall below 6 degrees Fahrenheit or exceed 91 degrees Fahrenheit.

🏘️ Winter

January is the coldest month with average highs of 34 degrees Fahrenheit and lows of 22 degrees Fahrenheit. Snow falls approximately 29.4 days annually, accumulating to 14.76 inches total. Winter preparation includes snow removal services, winter vehicle maintenance, and heating system reliability.

🏘️ Spring

April brings mild temperatures averaging 56 degrees Fahrenheit high and 40 degrees Fahrenheit low. May warms considerably with average highs of 68 degrees Fahrenheit and lows of 50 degrees Fahrenheit, making it an ideal season for outdoor recreation and home maintenance.

🏘️ Summer

July reaches peak warmth with average highs of 82.9 degrees Fahrenheit and lows of 64 degrees Fahrenheit. Summers are warm and humid with 162.2 rainfall days annually. This season attracts outdoor activities including river kayaking and park recreation.

🏘️ Autumn

September averages between 56 degrees Fahrenheit and 74 degrees Fahrenheit with spectacular foliage displays. Fall brings ideal temperatures for outdoor festivals and recreational activities before winter arrives.

Healthcare & Medical Services

Cromwell residents access comprehensive healthcare through local providers and nearby hospital systems. Quality medical care supports healthy living across all demographics.

🏥 Nearby Hospitals

Middlesex Hospital in adjacent Middletown, CT has received America's 100 Best Hospitals Award and America's 250 Best Hospitals Award recognition. Additional hospitals in Meriden, New Britain, and surrounding communities provide additional medical options.

🏘️ Specialty Services

The Orthopaedic Associates Surgery Center LLC and The Center for Children with Special Needs provide specialized medical services. These facilities complement primary care and urgent care options throughout the community.

Shopping & Retail

Cromwell offers diverse shopping options from locally owned boutiques to national retailers serving all consumer needs.

🚤 Downtown Riverport

The historic Riverport features independent businesses including antique shops, boutiques, and personal services. Tea rooms and cafes provide casual dining and social gathering spaces within walking distance of riverfront parks.

🏘️ Main Street (Route 99)

Main Street showcases restaurants, pubs, personal services including dry cleaning and hair salons, and independent retailers serving daily community needs.

🏘️ Route 372 Corridor

The Route 372 shopping corridor hosts national retail chains and restaurant franchises including shopping centers with diverse retailers. This commercial area provides one-stop convenience for groceries, clothing, home goods, and family entertainment.

🌾 Farmers Market

The Town of Cromwell Farmers Market operates Friday evenings from 4 to 7 p.m. at Riverport Park during summer months. Local vendors offer farm-fresh vegetables, artisan goods, prepared foods, and live entertainment supporting local agriculture and artisans.

Arts, Culture & Entertainment

Cromwell celebrates creative culture through robust arts organizations, community events, and cultural institutions supporting diverse artistic expression.

🏘️ Cromwell Arts Alliance

The Cromwell Arts Alliance serves as a community resource supporting dance, theater, painting, writing, music, and multimedia arts. The organization develops opportunities for citizens of all ages to participate in and appreciate literary, visual, technical, and performing arts.

🏘️ Community Events

The Cromwell Riverport Festival returns annually celebrating town spirit and strengthening community connections. Town partnerships with local businesses and residents support cultural programming throughout the year.

🏛️ Historic Preservation

Cromwell's downtown district showcases how an 18th-century village center evolved into a 20th-century town. The 130-acre downtown encompasses two greens featuring architectural styles spanning 1750 to 1935, demonstrating community historical significance.

🎣 Recreational Arts Programs

Cromwell Recreation Department offers Broadway Jazz classes, tap dancing, music instruction, and arts and crafts programs. These youth and adult programs build community engagement and artistic skill development.

Development & Future Growth

Cromwell continues attracting residential and commercial development supporting community growth while maintaining neighborhood character. Town planning efforts balance new development with preservation of historic and natural assets.

🏘️ Growth Trends

Population growth of 1.42% since the 2020 census reflects steady residential expansion. The 16.4% year-over-year home price appreciation indicates strong market demand and developer confidence in the community's future.

🏘️ Commercial Development

The Route 372 corridor continues attracting commercial investment with retail, hospitality, and office development. This commercial activity generates employment, property taxes, and community amenities.

🏘️ Infrastructure Investment

Town planning includes infrastructure improvements supporting residential and commercial growth while maintaining water quality, flood control, and environmental protection along the Connecticut River.

Frequently Asked Questions

As of May 2025, the median home price in Cromwell is $340,000, up 16.4% from the previous year. The median price per square foot is $217. Prices vary based on neighborhood, home age, condition, and amenities.

Yes, Cromwell schools rank above average in Connecticut. Cromwell High School ranks 41st of 145 Connecticut high schools with an 88.4% graduation rate. Cromwell Middle School ranks 74th of 252 Connecticut middle schools. The district maintains a 12-to-1 student-teacher ratio. Some families should address the 17.7% chronic absenteeism rate.

The 2024 mill rates total 30.79 mills (27.33 town plus 3.46 fire district), equating to $29.41 per $1,000 of assessed value. The median effective property tax rate is 2.94%, with median annual tax bills around $5,599. Property taxes are due July 1 annually.

The driving distance from Cromwell to Hartford is approximately 14 miles, taking about 21 minutes by car. Public transit via line 55 bus takes 39 minutes and costs $1-$4. Hartford is home to major insurance and financial services companies providing employment opportunities.

Cromwell participates in the National Flood Insurance Program with designated flood zones along the Connecticut River. Properties in high-risk flood zones require flood insurance. Buyers should verify flood zone status through FEMA's Flood Map Service Center and the town GIS system before purchasing.

Connecticut Housing Finance Authority offers down payment assistance programs including Time To Own (0% forgivable loans up to $50,000) and HFA mortgage programs with below-market rates. Community Renewal Team provides free housing counseling at 860-761-2381. Novus Home Mortgage offers competitive rates through NMLS-approved loan officers Ryan and Megan.

Mortgage Services & Financing

Novus Home Mortgage provides comprehensive lending solutions for Cromwell homebuyers, investors, and refinancers. As a federally licensed mortgage lender serving all 50 states via NMLS, Novus offers competitive rates, flexible programs, and expert guidance through every mortgage stage.

🏦 Novus Home Mortgage

Phone:386-690-5858

Website:www.winslowloan.com

Loan Officers:

Service Area:All 50 states

Federal License:NMLS registered

🏦 Loan Programs & Products

Novus Home Mortgage offers conventional loans, FHA loans, VA loans, USDA loans, and portfolio programs. Down payment options range from zero down for qualified borrowers to traditional 20% down. Loan officers work with first-time buyers, experienced investors, and self-employed professionals.

🏦 Pre-Approval & Application

Get pre-approved online at www.winslowloan.com or call 386-690-5858 to speak with a loan officer. Pre-approval demonstrates serious intent to sellers and helps clarify your home purchase budget.

Winslow Homes LLC - Real Estate Services

Winslow Homes LLC serves Connecticut's real estate market with professional, ethical real estate services for buyers, sellers, and investors. Co-owners Ryan and Megan Winslow bring passion, expertise, and local market knowledge to every transaction.

🏘️ Winslow Homes LLC

Email:[email protected]

Website:www.winslow-homes.com

Brokers:

Licensed States:FL, MA, CT, RI

📊 Market Expertise

With extensive Connecticut market knowledge and multi-state licensing, Winslow Homes LLC understands neighborhoods, market trends, property values, and investment strategies throughout New England. The brokerage combines technology, market data, and personal service to achieve client objectives.

About Winslow Homes LLC

Winslow Homes LLC is a full-service real estate brokerage licensed in Florida, Massachusetts, Connecticut, and Rhode Island. Ryan and Megan Winslow combine experience with commitment to client success and market expertise.

🏘️ Brokerage Services

Buyer representation guides clients through property selection, negotiation, and closing. Seller marketing strategies position properties competitively. Investment advisory services assist buyers seeking income-producing properties. Relocation assistance helps families moving to new communities.

📊 Market Expertise

The Winslow Homes team brings specialized knowledge of Cromwell neighborhoods, property values, market trends, and investment opportunities. Regular market analysis keeps agents informed on current conditions.

📞 Contact Information

Winslow Homes LLC
Email: [email protected]
Phone: 386-690-5858

MLS Disclaimer & Legal Information

All real estate information provided by Winslow Homes LLC is derived from the Multiple Listing Service (MLS) and public sources. Information is deemed accurate but not guaranteed. Buyers should verify all information independently before making purchase decisions.

This website and all information provided does not constitute legal, financial, or tax advice. Buyers should consult qualified professionals including real estate attorneys, tax advisors, and financial planners before making property decisions.

Equal Housing Opportunity: Winslow Homes LLC operates under fair housing principles. Discrimination based on race, color, religion, sex, handicap, familial status, national origin, sexual orientation, or gender identity is prohibited.

Nearby Communities

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Cromwell Homes by Price Range

Entry Level

Starter homes, condos, and smaller single-family properties. Good for first-time buyers and investors.

Mid Range

Three to four bedroom single-family homes in established neighborhoods. Updated kitchens and baths common.

Upper Tier

Larger lots, premium finishes, and preferred locations. Often near top-rated schools or amenities.

Luxury

Estates, waterfront, and custom builds. Private showings and off-market access through Winslow Homes.

Call 386-690-5858 to filter Cromwell listings by exact budget and features.

Cromwell Market Snapshot

Cromwell real estate reflects regional Connecticut trends. Inventory, days on market, and pricing shift each month. Our team tracks these numbers weekly.

Current indicators

  • Active listing count
  • Median list and sold price
  • Average days on market
  • Sale-to-list price ratio
  • Price per square foot

Want the current Cromwell numbers? Call 386-690-5858 for a live market report.

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About Your Team at Winslow Homes

Winslow Homes stands apart through its commitment to excellence, cutting-edge marketing strategies, and deep local market knowledge across the states we serve. Our brokerage specializes in a range of real estate services, including: Residential Sales – Helping buyers find their dream homes and sellers achieve top dollar for their properties. Luxury & Coastal Properties – Expertise in high-end, waterfront, and vacation homes in desirable locations.Investment & Income Properties – Assisting investors in identifying profitable opportunities. New Construction & Development – Partnering with builders and developers to bring new projects to market. Relocation Services – Providing a seamless experience for clients moving to or from the areas we serve.

Winslow Homes

Winslow Homes is an independent real estate brokerage licensed in Massachusetts, Florida, Connecticut, and Rhode Island, dedicated to providing expert guidance, innovative marketing, and seamless transactions for buyers, sellers, and investors. With a reputation built on honesty, integrity, trust, and service (H.I.T.S.), Winslow Homes offers personalized, client-centered solutions that make real estate transactions smooth and successful.

At Winslow Homes, we believe in building lasting relationships with our clients, ensuring every transaction is guided by transparency, communication, and expert negotiation.

Winslow Homes was founded by Megan and Ryan Winslow, a husband-and-wife team who transformed their passion for real estate into a thriving brokerage. Their journey began in 2009, when they applied their entrepreneurial mindset, housing market expertise, and dedication to client success to real estate transactions in Central Massachusetts, and eventually Central and Coastal Florida. As a Massachusetts native and son of a real estate broker, Ryan Winslow pursued real estate at the conclusion of his military career, following an Honorable Discharge from the U.S. Army. Together, Megan and Ryan became a dynamic duo in the industry, providing expert representation and growing a loyal client base.

By 2016, they had expanded their reach across Massachusetts, Florida, Rhode Island, and Connecticut, earning recognition as one of the “Best of Central MA” and solidifying their reputation as trusted real estate professionals. Their success led to the creation of Winslow Homes LLC, a brokerage built on client-first service, market expertise, and a commitment to achieving real estate goals at the highest level.

Today, Winslow Homes continues to thrive as a full-service brokerage, offering a modern, results-driven approach while maintaining a personal touch in every transaction. Megan and Ryan reside in New Smyrna Beach, FL, with their three children-Jaikob, Jaelynn, and Julianna-leading a brokerage that reflects their values, experience, and dedication to helping clients succeed in real estate.

Whether you’re buying, selling, or investing, Winslow Homes is your trusted partner in real estate

Our Offices

Winslow Homes is a fully licensed real estate brokerage serving Massachusetts, Florida, Connecticut, and Rhode Island. With extensive market knowledge and a commitment to exceptional service, our team is equipped to help buyers, sellers, and investors navigate real estate transactions across these states. 

FLORIDA

New Smyrna Beach, FL 32168

Contact: (386) 690-5858

MASSACHUSETTS

Worcester, MA 01606

Contact: (386) 690-5858

CT & RI

Contact: (386) 690-5858

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