Doctor Phillips, Florida

Real Estate Guide and Market Analysis

Quick Facts

12,328
Population
$570K
Median Home Price
$101,540
Median Household Income
44 years
Median Age

About Doctor Phillips

Doctor Phillips is an unincorporated community in Orange County, Florida, located in southwest Orlando near the prestigious Butler Chain of Lakes. This affluent suburb sits just 10 minutes from Walt Disney World and 15 minutes from downtown Orlando, making it an ideal location for those seeking upscale lakeside living with convenient access to major attractions and employment centers. The community takes its name from Dr. P. Phillips, a prominent citrus baron who shaped the region's early development.

Today, Doctor Phillips represents one of Orlando's most sought-after residential destinations. The area is characterized by luxury homes, spectacular lakeside properties, and the renowned Restaurant Row. With a population of approximately 12,328 residents, the community maintains a balance between exclusivity and accessibility. The neighborhoods feature well-maintained properties built over several decades, from vintage character homes in Sand Lake Hills to contemporary estate homes in Bay Hill and Cypress Point. The area's lakes, nature preserves, and proximity to world-class amenities make it appealing to families, professionals, and retirees.

Doctor Phillips ranks among Orange County's most desirable communities, with a median household income of $101,540 and a median home price of $570,000. The area attracts residents seeking sophisticated living, excellent schools, diverse dining options, and proximity to Orlando's business corridors. Whether you're relocating to the area or investing in Florida real estate, Doctor Phillips offers the combination of established value, quality infrastructure, and growth potential that discerning homebuyers seek.

Housing Market Overview

The Doctor Phillips real estate market reflects strong demand and steady appreciation. Recent data shows median home prices at $570,000 (June 2025), up 10.7% year-over-year. Homes sell for approximately $290 per square foot, with prices ranging from $400,000 for townhouses to multi-million dollar estate properties. The market has become more measured, with homes averaging 27 days on market compared to 9 days previously, indicating a shift toward a more balanced buyer-seller dynamic.

Price Range

$400K–$3M+

Townhouses to luxury estates

Median Price

$570,000

Up 10.7% YoY

Price per Sq Ft

$290

High-quality finishes

Days on Market

27 days

Buyer-friendly pace

πŸ“ˆ Market Trends

The Doctor Phillips market is experiencing a healthy correction after rapid appreciation. The extended selling timeline gives buyers time to make informed decisions while rewarding well-priced properties with strong showings. Investment properties continue to attract attention, particularly lakefront homes and properties near Restaurant Row. First-time move-up buyers frequently target this market as an upgrade from entry-level Orlando neighborhoods.

Neighborhoods & Communities

Doctor Phillips encompasses several distinct neighborhoods, each with unique character and appeal. The community is divided into smaller areas that range from quiet residential enclaves to upscale lakefront destinations.

Bay Hill

One of Doctor Phillips' most prestigious neighborhoods, Bay Hill features grand estates, championship golf facilities at Bay Hill Club and Lodge, and exclusive waterfront properties. Homes here command premium prices and offer access to golf schools, luxury spas, and manicured grounds.

Cypress Point

Cypress Point offers upscale lakeside living with modern architectural designs and high-end finishes. This gated community appeals to buyers seeking contemporary luxury and privacy within the Doctor Phillips area.

Sand Lake Hills

A tight-knit, well-maintained community with an active HOA, Sand Lake Hills features homes built primarily in the 1970s and 1980s that have been thoughtfully updated. Properties here offer good value relative to other Doctor Phillips neighborhoods and attract families and active adults.

Isle of Osprey

Isle of Osprey combines lakefront living with gated security and resort-style amenities. This exclusive neighborhood features premium properties with water views and access to private facilities.

Bay Ridge & Bay View

Bay Ridge and Bay View offer residential stability with established tree-lined streets and community infrastructure. These neighborhoods provide family-friendly environments with convenient access to schools, parks, and shopping.

Turtle Creek

Turtle Creek is a sought-after neighborhood known for quality construction, spacious lots, and strong community identity. The area appeals to buyers seeking privacy and long-term property appreciation potential.

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Property Types

Doctor Phillips offers diverse property options to suit various buyer preferences and budgets.

Single-Family Homes

Luxury estates, contemporary designs, and classic properties ranging from 2,000 to 8,000+ square feet on lakefront and golf course-adjacent lots.

Townhomes & Villas

Low-maintenance luxury townhouses and villa properties, ideal for move-up buyers and those seeking sophisticated urban lifestyle without single-family maintenance.

Lakefront Properties

Premium waterfront homes on the Butler Chain of Lakes, featuring docks, boat lifts, and water views. These properties command premium pricing and appreciation.

Golf Course Homes

Exclusive properties at Bay Hill Club and adjacent communities, offering golf access, resort amenities, and championship course views.

Schools & Education

Doctor Phillips is served by Orange County Public Schools, an A-rated district offering strong academic programs and magnet opportunities. The area benefits from three elementary schools serving different sections of the community, consolidated middle school services, and one of Orange County's top-rated high schools.

πŸŽ’ Elementary Schools

  • Dr. Phillips Elementary School (6909 Dr Phillips Blvd) – Offers Gifted & Talented program, performing above average for the state
  • Bay Meadows Elementary School – Serves portions of Doctor Phillips with comprehensive K-5 programming
  • Sand Lake Elementary School – Community-focused school with strong parent involvement

πŸ“š Middle School

  • Southwest Middle School – Designated middle school for Doctor Phillips students, grades 6-8

πŸ“š High School

  • Dr. Phillips High School (6500 Turkey Lake Rd) – Ranked 220th in Florida. Features AP courses (61% participation), Project Lead The Way curriculum, 31 sports, magnet programs in International Studies and Visual & Performing Arts

Lifestyle & Amenities

Doctor Phillips delivers a sophisticated lifestyle with upscale dining, recreation, shopping, and cultural attractions within minutes. The community's location near major Orlando attractions combined with its own established infrastructure makes it ideal for active residents seeking both relaxation and entertainment.

🎣 Recreation & Entertainment

  • Bay Hill Club and Lodge – Championship golf course, golf school, luxury fitness center, spa, and manicured grounds
  • Butler Chain of Lakes – Water sports, boating, fishing, and lakeside parks
  • Downtown Orlando – 15 minutes away, featuring Dr. Phillips Center for the Performing Arts with Broadway shows, ballet, comedy, and educational programs
  • Walt Disney World – 10 minutes away for family entertainment and special events
  • International Drive – Theme parks, attractions, shopping, and entertainment

Dining & Restaurants

Doctor Phillips is renowned throughout Orlando for Restaurant Row and upscale dining options. The area's concentration of high-quality restaurants attracts food enthusiasts and business professionals throughout the region.

🍽️ Notable Restaurants

  • Big Fin Seafood – Boat-to-table concept featuring Florida catches, creative cocktails, upscale atmosphere
  • Dragonfly Robata Grill & Sushi – Modern Japanese gastropub with sushi, steak, seafood, noodles
  • BoiBrazil – Authentic Brazilian steakhouse with rotisserie meats and gourmet salad selection
  • The Whiskey – Upscale casual dining and craft cocktails
  • Sixty Vines – Wine-focused restaurant with Southern-inspired cuisine
  • Wonderful Hand Pulled Noodle – Authentic Asian dining
  • Voodoo Bayou – Cajun and Louisiana cuisine
  • bartaco – Upscale street food and cocktails (7600 Dr Phillips Blvd)

Restaurant Row on Sand Lake Road is recognized throughout Orlando as a premier dining destination with diverse cuisines, trendy bars, and chef-driven menus.

Commute & Transportation

Doctor Phillips offers exceptional commute convenience for workers throughout the Orlando metro area. The community's central location on the west side of Orange County provides quick access to major employment corridors.

πŸš— Commute Times

  • Downtown Orlando: 15 minutes
  • Average commute: 26 minutes
  • International Drive: 10 minutes
  • Walt Disney World: 10 minutes
  • Orlando International Airport: 25-30 minutes

πŸš— Major Employers Nearby

Doctor Phillips benefits from proximity to major Orange County employers. The area's unemployment rate is 0.5% below the US average, with a 3.9% job market increase since 2022. Primary industries include arts, entertainment, recreation, healthcare, accommodation, and food services.

Cost of Living

Doctor Phillips ranks among Orlando's higher cost-of-living communities, reflecting its upscale positioning and desirable location. Strong median household income ($101,540, up 80.2% above national average) helps offset expenses.

Category Cost Index vs. National Average
Overall Cost of Living 115 15% higher
Housing 108.6% Much higher
Utilities 90.1% 9.9% lower
Groceries 105% 5% higher
Transportation 102% 2% higher

πŸ›’ Rental Market

  • Studio: $1,520/month
  • 1-Bedroom: $1,791/month
  • 2-Bedroom: $2,409/month
  • 3-Bedroom: $2,949/month

Property Taxes

Doctor Phillips is unincorporated Orange County, subject to unincorporated Orange County millage rates plus school district and special district levies.

πŸ’΅ Tax Calculation

  • Unincorporated Orange County base rate: 4.4347 millage
  • Additional levies: School district, special districts vary by property location
  • Average annual tax on median $570,000 home: approximately $2,200-2,500 (estimated)
  • Tax is calculated on property's assessed value (typically 85% of fair market value)

πŸ’΅ Tax Planning

Homestead exemption may reduce taxable value by $50,000 for primary residences. We recommend consulting with a tax professional to understand your specific property's tax implications.

Flood Zones & Risk Management

Florida properties require flood risk assessment due to the state's hurricane exposure and high water table. Doctor Phillips' elevation and distance from immediate coastal areas provide better flood position than low-lying areas, but flood insurance remains important.

🌊 Understanding Flood Risk

  • FEMA flood maps determine insurance requirements and building codes
  • High-risk zones require flood insurance for federally-backed mortgages
  • Moderate to low-risk zones still experience localized flooding from tropical weather
  • Properties near the Butler Chain of Lakes warrant careful elevation and drainage review

πŸ“‹ Flood Insurance & Protection

Homeowners in all zones should carry flood insurance. National Flood Insurance Program policies start at $500+ annually; private policies may offer better rates in lower-risk zones. Check your property's flood zone at msc.fema.gov.

Investment Potential

Doctor Phillips presents strong real estate investment fundamentals. The area combines established value, strategic Orlando location, diverse buyer demographics, and consistent appreciation.

πŸ’° Investment Strengths

  • Market Position: Top-tier Orange County community with sustained demand
  • Appreciation: 10.7% YoY growth with long-term track record of steady increases
  • Rental Demand: Strong investor interest and tenant quality at premium rents
  • Employment: Unemployment 0.5% below national average; 3.9% job growth since 2022
  • Demographics: Affluent residents, high income levels, low turnover rates
  • Infrastructure: A-rated schools, healthcare facilities, established amenities
  • Tourism: Proximity to Disney World supports short-term rental demand

πŸ’° Explore Mortgage Options

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First-Time Homebuyers in Doctor Phillips

Doctor Phillips welcomes first-time homebuyers with townhomes, smaller single-family homes, and entry-priced properties. The strong rental market provides flexibility for buyers testing the area.

🏘️ Financing Programs Available

  • Florida Housing Program: Up to 5% down payment assistance ($10,000-$35,000) for FHA, VA, USDA, and conventional loans
  • Florida Assist (FL Assist): Up to $10,000 as a 0% deferred second mortgage
  • Hometown Heroes Program: Up to 5% down for law enforcement, firefighters, educators, military, and veterans
  • FHA Loans: 3.5% down payment, lower credit requirements
  • VA Loans: 0% down for eligible veterans and active military, no PMI
  • Conventional Loans: 3-5% down with competitive rates

🏘️ Getting Started

First-time homebuyers must demonstrate credit score of 640+, stable income, and reasonable debt-to-income ratios. Our team connects you with loan officers experienced in first-time buyer programs.

Relocating to Doctor Phillips

Doctor Phillips attracts corporate relocations and lifestyle moves. The community's professional environment, school quality, and amenities support smooth transitions.

🏘️ Relocation Services & Support

  • Temporary Housing: Furnished rentals and extended-stay options available
  • School Enrollment: Orange County Public Schools provides smooth enrollment
  • Community Integration: Active neighborhood associations and social groups
  • Area Orientation: Our team provides comprehensive guides and neighborhood tours

Active Adult & 55+ Living

While Doctor Phillips lacks age-restricted communities, it appeals strongly to active adults and retirees seeking sophisticated living, golf, health services, and cultural activities.

⛰️ Why 55+ Choose Doctor Phillips

  • Healthcare: Orlando Health Dr. P. Phillips Hospital with full specialty services
  • Golf & Recreation: Bay Hill Club and Lodge with championship golf and resort amenities
  • Cultural Activities: Dr. Phillips Center for the Performing Arts with Broadway and ballet
  • Dining & Social: Restaurant Row provides upscale dining and social opportunities
  • Lakes & Parks: Butler Chain of Lakes offers boating, fishing, and outdoor activities

Employment & Economic Outlook

Doctor Phillips benefits from strong Orange County economic growth. The area's unemployment rate is 0.5% below national average with diverse employment opportunities.

πŸ’Ό Major Employers

  • Orlando Health Dr. P. Phillips Hospital – 285-bed facility, major regional employer
  • Disney World & Tourism: Jobs within 10 minutes
  • International Drive Corridor: Attractions, hotels, entertainment venues
  • Downtown Orlando: Professional services, finance, technology
  • Medical & Healthcare: Expanding sector with growth opportunities

πŸ’Ό Economic Growth

Orange County has seen 3.9% job market increase since 2022. Primary industries include arts, entertainment, recreation, healthcare, accommodation, and food services. Median household income of $101,540 demonstrates economic strength.

Utilities & Infrastructure

Doctor Phillips enjoys reliable utility service with below-average costs compared to national averages.

🏘️ Utility Providers & Costs

  • Electric: Duke Energy (Florida), utilities 9.9% lower than national average
  • Water/Sewer: Orange County Utilities Department
  • Internet/Telecom: Multiple providers available
  • Infrastructure: Established paved roads, drainage systems, reliable emergency services

Climate & Weather

Doctor Phillips enjoys a subtropical Florida climate with warm temperatures year-round and abundant sunshine.

🏘️ Temperature & Seasons

  • Average Year-Round Temperature: 73Β°F
  • Temperature Range: 52Β°F to 90Β°F
  • Summer: Hot and humid, June-September, 85-92Β°F with afternoon thunderstorms
  • Winter: Mild and pleasant, December-February, 60-75Β°F
  • Annual Rainfall: 51 inches, concentrated in summer months

🏘️ Hurricane Season

Hurricane season runs June through November. Central Florida's inland location provides protection compared to coastal areas. Storm preparedness, home insurance, and drainage management are essential.

Healthcare & Medical Services

Doctor Phillips benefits from excellent healthcare infrastructure with world-class facilities and specialists.

πŸ₯ Primary Hospital

Orlando Health Dr. P. Phillips Hospital (9401 Turkey Lake Rd)
A 285-bed award-winning facility since 1985 serving southwest Orange County. Services include 24-hour emergency care, advanced imaging, orthopedic surgery, cancer treatment, wound care, and rehabilitation services.

πŸ₯ Additional Medical Facilities

  • AdventHealth Palm Parkway (7823 Palm Pkwy) – Full-service hospital
  • AdventHealth Centra Care Dr. Phillips (8014 Conroy Windermere Rd) – Urgent care
  • Orlando Health Orlando Regional Medical Center (52 W Underwood St) – Major downtown facility

Shopping & Retail

Doctor Phillips provides convenient shopping with upscale retail centers and specialty boutiques.

πŸ›οΈ Local Shopping Centers

  • The Marketplace at Dr. Phillips (7720 Dr Phillips Blvd) – 65+ shops, restaurants, salons. Anchored by Stein Mart, HomeGoods, Office Depot.
  • Dellagio Town Center (7924-8075 Via Dellagio Way) – Upscale shopping and dining
  • Phillips Crossing (8015 Turkey Lake Rd) – Retail and service centers

πŸ›οΈ Regional Shopping Destinations

  • The Mall at Millenia (4200 Conroy Rd) – Upscale mall with international brands and fine dining
  • The Florida Mall (8001 S Orange Blossom Trl) – Major regional mall
  • Disney Springs – 10 minutes away, upscale shopping and dining

Arts, Culture & Entertainment

Doctor Phillips area offers access to world-class cultural institutions and entertainment.

⛰️ Dr. Phillips Center for the Performing Arts

Located in Downtown Orlando (15 minutes away), featuring Walt Disney Theater, Steinmetz Hall, Broadway shows, ballet, comedy, classical music, and educational programs.

🎣 Entertainment & Recreation

  • Local Events: Neighborhood festivals and seasonal celebrations
  • Theme Parks: Walt Disney World (10 min), Universal Orlando, SeaWorld (25 min)
  • Cultural Access: Close proximity to downtown performing arts institutions

New Developments & Future Growth

Doctor Phillips maintains stable character while adapting to market demands. Development focuses on selective infill, renovation, and property upgrades rather than large-scale new construction.

🏘️ Growth Patterns

  • Sand Lake Road Restaurant Row continues upscale evolution
  • Selective townhouse and villa development in established neighborhoods
  • Property renovation and modernization of existing homes
  • Infrastructure improvements and drainage enhancements

🏘️ Long-Term Outlook

Doctor Phillips is expected to maintain its position as Orange County's premier residential community. The combination of established desirability, school quality, employment proximity, and amenities supports continued appreciation.

Pros & Cons of Living in Doctor Phillips

Advantages

  • Top-tier community with strong appreciation history
  • Excellent Orange County schools (A-rated district)
  • Multiple upscale neighborhoods with distinct character
  • Sophisticated dining and entertainment (Restaurant Row)
  • Lakefront living and golf amenities (Bay Hill Club)
  • Close to Disney World (10 min) and downtown (15 min)
  • Strong job market with below-average unemployment
  • High median income and affluent demographics
  • Established infrastructure and reliable services
  • Healthcare excellence (Dr. P. Phillips Hospital)
  • Diverse property types and price points

Challenges

  • Higher cost of living than Orlando average (15%+)
  • Housing significantly above regional average
  • Hot, humid summers with afternoon thunderstorms
  • Hurricane season requires preparedness (June-Nov)
  • Flood insurance necessary for most properties
  • High traffic on Sand Lake Road and nearby corridors
  • Close proximity to theme parks means tourist congestion
  • Limited large-scale new development
  • Competitive market with 27-day average sales time
  • Premium pricing limits buyer pool
  • Older home stock requires renovation
  • Limited public transit (car dependent)

Frequently Asked Questions

What is the median home price in Doctor Phillips?
As of June 2025, the median home price is $570,000, up 10.7% year-over-year. Prices range from $400,000 for townhouses to $3 million+ for luxury estates. Homes average 27 days on market.
What are the best neighborhoods in Doctor Phillips?
Doctor Phillips offers several distinct neighborhoods. Bay Hill features exclusive estates and golf amenities. Cypress Point offers upscale lakeside homes. Sand Lake Hills provides value with well-maintained properties. Isle of Osprey combines luxury with gated security. Bay Ridge and Bay View offer family-friendly established living. Turtle Creek appeals to buyers seeking privacy and appreciation potential.
Are Doctor Phillips schools good?
Yes. Orange County Public Schools is an A-rated district. Dr. Phillips Elementary and Bay Meadows serve the area with strong programs. Dr. Phillips High School ranks 220th in Florida with 61% AP participation, Project Lead The Way curriculum, and 31 sports.
How far is Doctor Phillips from Disney World?
Doctor Phillips is approximately 10 minutes from Walt Disney World, making it ideal for families seeking proximity to theme parks. Downtown Orlando is 15 minutes away. This location balance is a key advantage.
What is the average property tax rate?
Doctor Phillips is unincorporated Orange County with a base millage rate of 4.4347 plus additional school district and special district levies. Estimated annual tax on a $570,000 home is approximately $2,200-2,500. Homestead exemption may reduce taxable value by $50,000.
Is flood insurance required in Doctor Phillips?
Flood insurance is not required in all areas but is strongly recommended. Central Florida's inland location provides better position than coastal areas, but tropical storms bring heavy rainfall. Check your property's FEMA flood zone at msc.fema.gov. Rates vary by zone and elevation.
What financing options are available for first-time homebuyers?
Multiple programs support first-time buyers including Florida Housing Program (up to $35,000 down assistance), Florida Assist (0% second mortgage up to $10,000), Hometown Heroes Program (law enforcement, firefighters, educators, military), FHA loans (3.5% down), VA loans (0% down), and conventional loans (3-5% down). Credit score 640+ required.

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Mortgage & Financing Services

Novus Home Mortgage, federally licensed for all 50 states, offers comprehensive financing solutions for Doctor Phillips homebuyers.

🏦 Loan Programs

  • Conventional Loans: 3-5% down, competitive rates, flexible terms
  • FHA Loans: 3.5% down, accessible credit requirements
  • VA Loans: 0% down for eligible veterans and active military, no PMI
  • USDA Loans: 0% down in eligible rural areas
  • Portfolio Loans: Non-traditional credit, self-employed, investment properties
  • Jumbo Loans: Loans exceeding conventional limits for luxury properties

🏦 Loan Officer Information

  • Ryan Winslow – NMLS 2426605
  • Megan Winslow – NMLS 2692933

🏦 Contact Information

  • Phone: 386-690-5858
  • Application URL: www.winslowloan.com
  • Hours: Monday-Friday 9am-5pm ET, Saturday by appointment

Real Estate Services & Contact

Winslow Homes LLC provides comprehensive real estate services in Doctor Phillips and throughout Orange County.

🏘️ Services Offered

  • Buyer representation and buyer's agent support
  • Seller marketing and strategic pricing
  • Property investment analysis and consulting
  • Relocation assistance for corporate and military moves
  • Rental property management and tenant placement
  • Short-sale and distressed property negotiation
  • Market analysis and property appraisal support
  • New construction and builder representation

🏘️ Brokerage Contact Information

  • Company: Winslow Homes LLC
  • Email: [email protected]
  • Website: www.WinslowHomesLLC.com
  • Service Areas: Orange, Brevard, Osceola, Volusia, Polk Counties
  • Brokerage Licenses: Florida, Massachusetts, Connecticut, Rhode Island

MLS & Disclaimer Information

Multiple Listing Service (MLS) Data: All property listings, sold prices, market statistics, and comparable sales are compiled from the Multiple Listing Service serving Orange County. MLS data is considered reliable but is not guaranteed. Market conditions fluctuate based on seasonal factors, property condition, and demand. Individual property history and transaction terms vary and should be verified with listing agents.

Real Estate Market Information: All demographic data, population statistics, income information, school ratings, employment data, and property valuations are compiled from publicly available sources including US Census Bureau, Orange County Property Appraiser, Orange County Public Schools, Bureau of Labor Statistics, FEMA, and real estate databases. Information is current as of publication but market conditions change continuously.

Professional Advice Disclaimer: This guide provides general real estate information for educational purposes and should not be considered investment advice, legal advice, or tax advice. We recommend consulting with qualified professionals before making purchase or investment decisions.

Data Accuracy & Updates: While all information is compiled from reliable sources, we do not guarantee accuracy of all data. School ratings, property tax information, flood zones, and other specifics should be independently verified through official sources. Homebuyer assistance programs and financing options change regularly.

Flood Zone & Insurance: FEMA flood zone designations determine flood insurance requirements. Check your property's flood zone at msc.fema.gov. Flood insurance costs and availability vary by zone. Standard homeowner's insurance does not cover flooding.

Property Tax Information: Property tax rates change annually. Tax amounts are estimates based on median property values. Your actual tax depends on assessed value, exemptions, and special district levies. Consult Orange County Property Appraiser for specific amounts.

Hurricane & Weather: Central Florida experiences hurricane season June through November. Homeowner's insurance may exclude wind and flood damage. We recommend reviewing policy coverage and following emergency preparedness guidance.

Contact & Services: All contact information is current as of publication. Financing programs and loan products are subject to lender approval and availability.

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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 β€œBest 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. 

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Contact: (386) 690-5858

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