Cookstown Property: 4 Houses & Condos for Sale

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House for sale: 7 RILEY Street, Cookstown

50 photos

$1,199,000

7 Riley Street, Cookstown, Ontario L0L 1L0

4 beds
5 baths
23 days

... offering approximately 3,400+ sq. ft(Above Ground level) and approx. 1,350+ sq. ft (Below ground level) of luxurious living space. This beautiful property features , a specious double car garage , an Open concept layout, and an abundant day light throughout. The Modern kitchen equipped with...

Listed by: Ajay Shah ,Homelife Miracle Realty Ltd (416) 809-2555
2884 89 Highway, Cookstown

12 photos

$1,990,000

2884 89 Highway, Cookstown, Ontario L0L 1L0

4 beds
1 baths
36 days

... floor, area=40 x 26 ft, 3rd floor attic =40 x 18 ft. 2) Warehouse Storage 100 x 40 ft, Concrete floor, 16' ceiling height, door 14'. Bungalow:$1900/month +utilities, Warehouse Storage $3250/month +utilities, Workshop/office currently vacant. 2 Septic beds and 2 drilled wells, Zoning: AG-Agricultural...

Andrew Kokelj,Coldwell Banker The Real Estate Centre Brokerage
Listed by: Andrew Kokelj ,Coldwell Banker The Real Estate Centre Brokerage (705) 734-4547
House for sale: 2 COPELAND Crescent, Cookstown

49 photos

$1,499,000

2 Copeland Crescent, Cookstown, Ontario L0L 1L0

6 beds
5 baths
58 days

Hwy 27 to Riley Street to Copeland Crescent Stunning Renovated Home in Cookstown, ideal for multigenerational living! - Beautiful corner-lot home filled with natural light. and exceptional curb appeal. Features include a stone driveway, landscaping, and French doors leading to a large composite

Geoff Morgan,Painted Door Realty Brokerage
Listed by: Geoff Morgan ,Painted Door Realty Brokerage (705) 790-0830
House for sale: 18 HERITAGE Road, Cookstown

43 photos

$1,000,000

18 Heritage Road, Cookstown, Ontario L0L 1L0

3 beds
3 baths
64 days

KING ST S (HWY 27S) LEFT ON KIDD'S LANE LEFT ON HERITAGE Welcome to 18 Heritage Road, a timeless gem located in the heart of the charming and historic village of Cookstown. This classic 3-bedroom, 3-bathroom home is full of warmth and character, featuring hardwood floors, a stunning open-concept

Home Prices in Cookstown

In 2025, Cookstown real estate in Ontario presents a classic small?town market: a mix of established streets, rural edges, and pockets of newer infill that draw buyers looking for space, privacy, and manageable commutes. Rather than wild price swings, conditions are set by a steady flow of Cookstown Real Estate listings, with sellers paying close attention to presentation while buyers focus on setting, lot traits, and renovation quality. Conversations about home prices usually centre on property condition and location within the village, as those remain the main drivers of value here.

Instead of fixating on headlines, many who search Cookstown Homes For Sale watch the balance between inventory and demand, the split of detached versus attached properties, and indicators like days on market to estimate negotiation room. Well?prepared homes in desirable pockets tend to attract prompt attention, while properties needing updates often move after longer exposure. Smart pricing strategy, staging, professional photography, and clear notes about recent improvements can influence outcomes as much as broader market sentiment; reviewing comparable sales and listing histories helps set realistic expectations when you Buy a House in Cookstown.

Explore Real Estate & MLS® Listings in Cookstown

There are 2 active MLS listings in Cookstown, including 2 houses. Listing data is refreshed regularly.

Use search filters to focus on the features that matter most: narrow by price range, select preferred bed and bath configurations, and refine for lot size, parking, and outdoor space. As you browse Cookstown Real Estate Listings, study full photo sets and floor plans to understand flow and storage, and compare finishes, mechanical updates, and yard utility. Reviewing recent activity on nearby streets and similar property types will help you shortlist the homes that best fit your plans.

Neighbourhoods & amenities

Cookstown offers a blend of a walkable village core and quieter residential pockets with mature trees and easy access to surrounding countryside. Proximity to schools, parks, community facilities, and local shops often shapes buyer preferences, with many valuing a short stroll to daily essentials and family?friendly amenities. On the edges of town, larger lots and calmer streets appeal to those prioritizing privacy, outdoor hobbies, and space for future projects. Commuter links to nearby employment centres add convenience for hybrid schedules, while trail networks, playgrounds, and recreational fields support an active lifestyle. Waterfront and greenspace access in the broader region also influences value signals, especially for buyers who prize weekend escapes, dog walking routes, or cycling?friendly terrain. When comparing Cookstown Neighborhoods, consider traffic patterns, sun exposure in the yard, and the character of adjacent homes, all of which can subtly affect long?term enjoyment and resale appeal.

Cookstown City Guide

Set within the Town of Innisfil in Simcoe County, Cookstown blends country calm with convenient access to larger centres. This Cookstown city guide gives a practical sense of the community's history, daily rhythm, and essentials for getting around, while highlighting things to do for weekends and casual outings. Whether you're visiting, relocating, or exploring Cookstown Real Estate, you'll find an approachable village atmosphere anchored by heritage charm and up?to?date amenities.

History & Background

Cookstown traces its roots to the 19th century, when settlers established a compact crossroads community serving surrounding farms and travellers. Over time, a main street of brick storefronts and Victorian?era homes took shape, reflecting the prosperity of a rural service hub where agriculture, milling, and general merchandising supported daily life. Around the region you'll also find towns like Thornton that share historical ties and amenities. Cookstown's heritage is visible in preserved architecture, seasonal fairs, and a tradition of local businesses that have adapted through generations.

Being part of Innisfil connects Cookstown to a broader municipal network while allowing the village to keep its distinct identity. Proximity to a major highway corridor later encouraged growth: as road travel increased, Cookstown evolved into a convenient stop for shoppers and day?trippers as well as a residential community. Today, the village balances antiques and independent shops with newer retail and services that support both locals and visitors.

Economy & Employment

Cookstown's economy is anchored by a mix of small?town retail, agriculture, and trades, with the regional draw of outlet shopping and antiques. Agriculture remains visible just beyond the village, with cash crops, market gardens, and agri?services shaping the local landscape. Construction and home?improvement trades are well represented, reflecting steady residential growth in Innisfil and neighbouring centres. Retail and hospitality provide ongoing employment, from boutique storefronts to larger shopping and dining options that serve a country?urban customer base.

Thanks to its location near a major north?south highway, Cookstown also benefits from logistics, warehousing, and service roles tied to transportation and regional distribution. Many residents commute to Barrie for healthcare and education, to Alliston for manufacturing, or to Newmarket and the northern GTA for professional services. Remote and hybrid work have become more common, and the village's quieter setting appeals to people who want more space while staying connected to the broader Ontario economy. Public sector roles — schools, municipal services, and community health — round out a stable employment mix that doesn't rely on a single industry.

Neighbourhoods & Lifestyle

Cookstown's neighbourhoods centre on a walkable historic core surrounded by residential pockets, rural concessions, and hobby farms. In the village heart you'll find character homes on tree?lined streets, welcoming front porches, and community halls that double as gathering places. A short stroll reaches everyday essentials: cafés, convenience spots, and independent shops, with plentiful window?browsing for antiques and unique finds. Neighbourhood?hopping is easy with nearby communities like Egbert and Churchill. Just beyond the core, newer subdivisions offer family?sized dwellings and cul?de?sac living, while the surrounding countryside features farmhouses, equestrian properties, and wooded lots for buyers seeking extra room.

Living in Cookstown means enjoying a calendar of small?town events and simple pleasures: seasonal fairs, holiday parades, and roadside produce stands in harvest months. Weekends often involve browsing antiques, meeting friends for brunch, or taking scenic drives to farmers' markets across Simcoe County. Parks and green spaces provide playgrounds, ball fields, and open lawns for picnics, while trails and quiet concession roads attract walkers, runners, and cyclists. Families value the community feel — kids can ride bikes to the park, neighbours greet one another, and local schools and clubs keep social life active.

For activities beyond shopping and dining, look to the wider Innisfil area for recreation centres, libraries, and lake access. Lake Simcoe is a short drive for boating and beach days in summer, and nearby conservation lands invite hiking in fall and snowshoeing or cross?country skiing in winter. The mix of rural vistas and accessible amenities makes Cookstown a comfortable choice for people who want the quiet of the country without losing everyday convenience.

Getting Around

Cookstown sits at a convenient crossroads, so driving is the simplest way to get around. Local routes connect quickly to a major north?south highway, making commutes to Barrie, Alliston, or the northern GTA straightforward when traffic allows. Within the village, streets are calm and walkable with ample parking near shops and services. Cyclists enjoy scenic concession roads, though lights and high?visibility gear are advisable, particularly at dusk. For broader commuting and day trips, consider nearby hubs such as Bond Head and New Tecumseth.

Regional transit usually involves driving to a GO Transit station or using local on?demand services through the town. Barrie and Bradford provide rail connections toward Toronto, with park?and?ride facilities to ease rush?hour travel. Carpooling is common among residents who share schedules with coworkers in larger centres, and winter tires are a useful seasonal investment since rural roads can be slick after snow squalls. If you're searching Cookstown Condos For Sale or Cookstown Houses For Sale, most daily errands are a quick trip and the county road grid makes navigation straightforward for newcomers.

Climate & Seasons

Cookstown experiences the full four?season cycle typical of central Ontario. Winters are cold and snowy with regular frost and occasional storms influenced by nearby lakes. The village looks postcard?ready after fresh snow, and residents take advantage of skating, tobogganing, and snowshoeing on local trails. It helps to allow extra time for winter commutes and to keep a shovel and sand in the car; rural gusts can create drifting snow in open fields.

Spring arrives gradually, coaxing early wildflowers along hedgerows and filling roadside stands with maple treats and greenhouse plants. As roads dry, gravel routes become popular for bike rides, and the village wakes from winter with community clean?ups and outdoor markets. Summer brings warm, sunny days and long evenings ideal for barbecues, patio dinners, and day trips to Lake Simcoe. Farm fields green up, produce stands flourish, and evening breezes keep things comfortable even when temperatures rise.

Autumn is a highlight: red maples and golden birches colour the countryside and harvest festivals populate the weekend calendar. It's prime time for scenic drives, apple picking, and trail walks beneath colourful canopies. As temperatures cool, residents settle into cozy routines, with cafés and community halls offering warm gathering spots. Across the year, the steady progression of seasons shapes life in Cookstown, appealing to those who favour small?town living with space to breathe.

Nearby Cities

If you are considering a home in Cookstown, explore nearby communities such as Scugog, Port Perry, Little Britain, Sunderland, and Caesarea to compare housing styles, local amenities and lifestyle options.

Browse listings or speak with a local agent to learn more about what each community offers and how it may fit your needs when searching for a home near Cookstown or comparing Ontario Real Estate Cookstown options.

Demographics

Cookstown is typically home to a mix of families, retirees and professionals, creating a community with diverse household types and life stages. Housing tends to include a prevalence of detached homes alongside condominium options and rental units, offering choices for those looking to settle, downsize, or rent while browsing Cookstown Real Estate Listings.

The area has a suburban, small?town character with nearby open space and local amenities that support a quieter lifestyle than a city core while still allowing reasonable access to larger urban centres for work, shopping and services across Ontario.