WINCHESTER MA Real Estate

Discover a wide selection of Winchester real estate for sale with the guidance of Kim Covino, a trusted expert in Massachusetts.

Search Townhomes in Lexington CALL ME

 

LET KIM GUIDE YOU THROUGH YOUR NEW HOME REAL ESTATE SEARCH WITH OUR INTERACTIVE MAPS, BEAUTIFUL ELEVATION IMAGES AND HOME VIDEO TOURS!

HERE'S SOME OF WHAT YOU WILL FIND IN OUR WINCHESTER Real Estate SEARCH RESULTS.

ABOUT WINCHESTER

Winchester, a typical New England town 8 miles north of Boston, offers world-class outdoor activities, shopping, cuisine, and culture.

This small town north of Boston emanates New England charm. Winchester's proximity to Boston, attractive downtown, rich cultural events, and plenty of open spaces make it a great vacation spot. Winchester's historic preservation reflects its industrial past. The Middlesex Fells Reserve, exciting boutiques, and great restaurants make Winchester a great vacation area.

Winchester offers a comprehensive range of attractions for permanent residents and vacationers. Winchester, 8 miles north of Boston, has two commuter train terminals that go into downtown Boston, making it handy for commuters and city-goers. Winchester has enough to do! The many shopping, dining, and cultural options guarantee new experiences. In addition, Winchester's parks, ponds, and trails offer year-round outdoor fun.

MARKET INSIGHTS

WINCHESTER HOUSING MARKET TRENDS

What is the housing market like in Winchester today?

In February 2023, Winchester home prices were down 28.3% compared to last year, selling for a median price of $1.0M. On average, homes in Winchester sell after 91 days on the market compared to 33 days last year. There were 4 homes sold in February this year, down from 10 last year.
 

How hot is the Winchester housing market? Winchester is very competitive. Homes sell in 31 days.

WINCHESTER LISTINGS & SALES

Sold

Winchester Real Estate

Property Types
Neighborhoods
Cities

WINCHESTER, MASSACHUSETTS

PREMIER NEW ENGLAND ESTATES

An iconic Boston suburb renowned for its exceptional schools, historic charm, and sophisticated New England elegance. Winchester represents the pinnacle of metropolitan living with suburban tranquility just 8 miles from downtown Boston.

WINCHESTER REAL ESTATE INTELLIGENCE

Q4 2024 COMPREHENSIVE ANALYSIS
$1.85M
MEDIAN SINGLE FAMILY HOME
▲ 6.8% from previous year
+42%
PRICE PREMIUM vs. MA AVERAGE
Top 5% in Massachusetts
18
DAYS ON MARKET
▼ 45% faster than 2023
0.8
MONTHS INVENTORY
Extreme seller's market

WINCHESTER MARKET DYNAMICS

PRICE SEGMENTS & PERFORMANCE

The Winchester market demonstrates exceptional strength across all price points, with luxury properties ($3M+) showing remarkable resilience and continued demand from Boston executives and international buyers.

Entry-Level ($1.2M - $1.8M) +8.2% YoY
Mid-Market ($1.8M - $3M) +6.5% YoY
Luxury ($3M+) +5.8% YoY

BUYER PROFILE & MOTIVATION

Winchester attracts highly educated professionals, academic leaders, and biotech executives seeking top-tier schools and convenient Boston access. The town's reputation for excellence drives sustained demand.

Families with School-Age Children 68%
Boston Commuters 25%
Empty Nesters/Downsizers 7%

DISTINCT NEIGHBORHOODS & ENCLAVES

THE MYSTIC LAKES AREA

Premier waterfront properties along Upper and Lower Mystic Lakes, offering private docks, beach rights, and stunning water views minutes from Boston.
PRICE RANGE $2.5M - $8M+
WATER ACCESS PRIVATE DOCKS
LAKE FRONTAGE DIRECT ACCESS

WEDGEMERE & MONTROSE

Historic districts featuring classic New England architecture, walking distance to Wedgemere Commuter Rail and Winchester Center's shops and restaurants.
PRICE RANGE $1.6M - $3.2M
ARCHITECTURE VICTORIAN/CRAFTSMAN
WALK SCORE 85+

WEST SIDE ESTATES

Spacious contemporary estates on larger lots near the Lexington border, offering privacy, modern amenities, and proximity to major highways.
PRICE RANGE $2.8M - $6M+
LOT SIZES 0.5 - 2+ Acres
NEW CONSTRUCTION PREMIUM

EDUCATION EXCELLENCE & LIFESTYLE

🎓

TOP-RATED SCHOOLS

Winchester Public Schools consistently rank #1 in Massachusetts, with 98% graduation rate and 25% attending Ivy League universities.

🚂

BOSTON COMMUTE

22-minute express train to North Station, easy access to I-93 and I-95. Perfect balance of suburban living with urban accessibility.

🏘️

TOWN AMENITIES

Vibrant town center with boutique shopping, fine dining, library, recreational facilities, and community events throughout the year.

INVESTMENT & MARKET INSIGHTS

MARKET TRENDS

TRENDING
Properties receiving 5-12 offers on average, with 35% selling above asking price in competitive bidding
NOTE
Limited land for new development driving teardown and renovation activity, with premium for move-in ready homes

LONG-TERM VALUE

INSIGHT
Winchester has shown 98% price retention through market cycles, demonstrating exceptional stability
DATA
Average property tenure of 12.3 years indicates high resident satisfaction and community stability

DISCOVER WINCHESTER LIVING

Schedule your private tour and receive our exclusive Winchester market analysis with pre-market opportunities.

REQUEST PRIVATE SHOWING

FIND YOUR DREAM WINCHESTER TOWNHOME FOR SALE

SCHEDULE A SHOWING

 

OUR RECENT CLIENT TESTIMONIALS

Search for Homes Around Winchester

Search by Cities Search by Zip Codes

TOP 5 FAQS ABOUT TOWNHOMES IN WINCHESTER MA

Living in a Winchester townhome offers several advantages. First, townhomes typically provide a balance between homeownership and shared community amenities, making them suitable for individuals or families looking for low-maintenance living. You'll often find well-maintained common areas, landscaping, and, in some cases, amenities like fitness centers or swimming pools. Additionally, townhomes can offer cost savings compared to single-family homes, both in terms of purchase price and ongoing maintenance expenses. Winchester's townhome communities are often located in convenient locations with easy access to schools, parks, shopping, and public transportation, making them a popular choice for many.

Winchester offers a variety of townhome styles to suit different preferences. You can find traditional New England-style townhomes with classic architectural features like clapboard siding and gabled roofs. Alternatively, there are modern townhomes with sleek designs, open floor plans, and contemporary finishes. Some townhome communities are part of larger developments, while others are standalone or part of smaller, more intimate complexes. Townhomes in Winchester come in various sizes, from two-bedroom units to more spacious three or four-bedroom layouts, accommodating different family sizes and lifestyles.

The real estate market for townhomes in Winchester, MA, tends to be dynamic and competitive. Like many desirable suburbs around Boston, Winchester experiences fluctuations in inventory and demand. Overall, the market has been strong, with a consistent demand for townhomes due to their affordability compared to single-family homes and the convenience of shared maintenance. Prices can vary based on location, size, and condition, so it's essential for buyers and sellers to stay informed about the latest market trends and work with experienced local real estate agents to make well-informed decisions.

Yes, many townhome communities in Winchester, MA, have homeowner associations (HOAs) that manage common areas, exterior maintenance, and other shared responsibilities. HOAs typically collect monthly or annual fees from homeowners to cover these costs. Before purchasing a townhome, it's essential to review the HOA's rules, regulations, and financial health. HOAs can provide valuable benefits, such as maintaining property values and ensuring that shared spaces are well-kept. However, it's crucial to understand the HOA's rules and fees and determine if they align with your preferences and budget.

Financing a townhome purchase in Winchester, MA, is similar to financing other types of real estate. Buyers can explore various mortgage options, including conventional loans, FHA loans, or VA loans if eligible. It's advisable to get pre-approved for a mortgage before starting your home search to understand your budget and make competitive offers. Additionally, some townhome developments may have financing restrictions or requirements imposed by the HOA, so it's crucial to work with a knowledgeable local lender who can guide you through the financing process and help you navigate any unique considerations related to townhome purchases.

Work With Kim

My team and I have a proven track record when it comes to negotiating skills and sourcing buyers from many different markets thanks to our premiere listings and strong referral base spanning Winchester and beyond. Referrals from past and present clients have become the base of our business, further proving our unmatched service!