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Maine Cumberland County Portland East Deering Winchester Woods

Winchester Woods

41 Winchester Dr, Portland, ME 04103

(0 reviews)

Property Rating

5.0
Excellent
Out of 5

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How Is This Rating Determined?

Every community on Apartments.com features a rating displayed on a 5-star scale. This rating includes average renter review scores and a building rating to determine an overall blended score for this property.

Building ratings are based on this community’s features, including the building design, construction, exterior spaces, and amenities. To learn more about the CoStar Building Rating System, refer to our official guidelines here.

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  • Monthly Rent

    $1,995 - $2,516

  • Bedrooms

    1 - 2 bd

  • Bathrooms

    1 ba

  • Square Feet

    745 - 907 sq ft

Winchester Woods
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Welcome to Winchester Woods Located within the desirable neighborhoods of East Deering, this beautiful area sits just outside of Downtown Portland. Winchester Woods is located less than a mile from Portland's multi-published and world renowned food scene, as well as grocery, retail, and Back Bay, which boasts a 3 1/2 mile walking loop around the bay. Family-friendly Payson Park, Portland trails, and access to I-295 are almost right around the corner. USM and UNE Portland campuses are also close by for anyone attending or seeking to attend classes. Winchester Woods is comprised of 4 buildings with one and two-bedroom units that feature spacious and open floor plans with modern fixtures, stainless steel appliances. Some added features include onsite parking, snow removal, lawn care, trash removal and maintenance with a 24/7 emergency response team. professionally managed, this properly has everything an apartment could have. Residents are respon sible for electricity (including heating /cooling and hot water), internet/cable. Some highlights of the location Each unit is equipped with heat pumps for unequalled year-round comfort. Efficient stainless-steel appliances Luxury vinyl plank flooring Carpets in the bedrooms What is included in the monthly rent? Parking Cold Water Lawn Care Snow Removal What utilities am I respon sible for as a Resident? Hot Water (electric) Cable/internet/phone Electric. Heat & Air Conditioning Supplied by energy efficient heat pumps monthly utility reimbursement charge of $18

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Pricing & Floor Plans

filter results by bedrooms
One Bedroom $1,995
1 Bed 1 Bath 745 Sq Ft
1 Available unit
Unit
Base Price
Sq Ft
Availability
Unit Details
  • Unit 41-303
    price $1,995
    square feet 745
    availibility Jan 1, 2026
Two Bedroom $2,495 – $2,516
2 Beds 1 Bath 907 Sq Ft
3 Available units
Unit
Base Price
Sq Ft
Availability
Unit Details
  • Unit 48-302
    price $2,495
    square feet 907
    availibility Now
  • Unit 41-104
    price $2,516
    square feet 907
    availibility Now
  • Unit 41-202
    price $2,495
    square feet 907
    availibility Jan 1, 2026
One Bedroom $1,995
1 Bed 1 Bath 745 Sq Ft
1 Available unit
Unit
Base Price
Sq Ft
Availability
Unit Details
  • Unit 41-303
    price $1,995
    square feet 745
    availibility Jan 1, 2026
Two Bedroom $2,495 – $2,516
2 Beds 1 Bath 907 Sq Ft
3 Available units
Unit
Base Price
Sq Ft
Availability
Unit Details
  • Unit 48-302
    price $2,495
    square feet 907
    availibility Now
  • Unit 41-104
    price $2,516
    square feet 907
    availibility Now
  • Unit 41-202
    price $2,495
    square feet 907
    availibility Jan 1, 2026
* Price shown is base rent. Excludes user-selected optional fees and variable or usage-based fees and required charges due at or prior to move-in or at move-out. View Fees and Policies for details. Price, availability, fees, and any applicable rent special are subject to change without notice.
* Square footage definitions vary. Displayed square footage is approximate.

Fees and Policies

The fees below are based on community-supplied data and may exclude additional fees and utilities.

  • One-Time Basics
    • Due at Application
      • Application Fee Per Applicant
        Charged per applicant.
        $0
    • Due at Move-In
      • Administrative Fee
        Charged per unit.
        $300

Property Fee Disclaimer: Based on community-supplied data and independent market research. Subject to change without notice. May exclude fees for mandatory or optional services and usage-based utilities.

Details

Lease Options

  • 12 mo

Property Information

  • Built in 2023
  • 48 units/3 stories

Matterport 3D Tours

1BD, 1BA Unit
1/2

About Winchester Woods

Welcome to Winchester Woods Located within the desirable neighborhoods of East Deering, this beautiful area sits just outside of Downtown Portland. Winchester Woods is located less than a mile from Portland's multi-published and world renowned food scene, as well as grocery, retail, and Back Bay, which boasts a 3 1/2 mile walking loop around the bay. Family-friendly Payson Park, Portland trails, and access to I-295 are almost right around the corner. USM and UNE Portland campuses are also close by for anyone attending or seeking to attend classes. Winchester Woods is comprised of 4 buildings with one and two-bedroom units that feature spacious and open floor plans with modern fixtures, stainless steel appliances. Some added features include onsite parking, snow removal, lawn care, trash removal and maintenance with a 24/7 emergency response team. professionally managed, this properly has everything an apartment could have. Residents are respon sible for electricity (including heating /cooling and hot water), internet/cable. Some highlights of the location Each unit is equipped with heat pumps for unequalled year-round comfort. Efficient stainless-steel appliances Luxury vinyl plank flooring Carpets in the bedrooms What is included in the monthly rent? Parking Cold Water Lawn Care Snow Removal What utilities am I respon sible for as a Resident? Hot Water (electric) Cable/internet/phone Electric. Heat & Air Conditioning Supplied by energy efficient heat pumps monthly utility reimbursement charge of $18

Winchester Woods is an apartment community located in Cumberland County and the 04103 ZIP Code. This area is served by the Portland Public Schools attendance zone.

Contact

Language: English
Open By Appointment Today
  • Monday - Friday, By Appointment
  • Saturday & Sunday, By Appointment
Property Management Company Logo

Community Amenities

  • Walking/Biking Trails

Apartment Features

Air Conditioning

Refrigerator

Tub/Shower

Stainless Steel Appliances

  • Air Conditioning
  • Heating
  • Tub/Shower
  • Stainless Steel Appliances
  • Kitchen
  • Oven
  • Range
  • Refrigerator
  • Instant Hot Water
  • Carpet
  • Lawn
Location Get Directions
Schools Restaurants Groceries Coffee Banks Shops Fitness
Amenities
  • Walking/Biking Trails
  • Air Conditioning
  • Heating
  • Tub/Shower
  • Stainless Steel Appliances
  • Kitchen
  • Oven
  • Range
  • Refrigerator
  • Instant Hot Water
  • Carpet
  • Lawn
Office Hours
Monday By Appointment
Tuesday By Appointment
Wednesday By Appointment
Thursday By Appointment
Friday By Appointment
Saturday By Appointment
Sunday By Appointment
877-652-5991
City - Portland

Welcome to Portland, Maine, where historic architecture meets coastal charm along the shores of Casco Bay. Portland's rental market offers diverse housing options, with one-bedroom apartments averaging $1,817. From converted warehouses in the Old Port to apartments in the West End and East End neighborhoods, including Munjoy Hill, renters can find homes that match their preferences. The tree-lined streets of Back Cove and Deering Center provide residential settings near parks and trails.

Portland's Congress Street Arts District serves as a cultural hub, anchored by the Portland Museum of Art. The Eastern Promenade stretches across 68 acres of waterfront parkland, offering walking trails and scenic harbor views. The city's acclaimed restaurant scene features James Beard Award-winning establishments, particularly concentrated in the Old Port and downtown areas.

Learn more about living in Portland 
Education
Colleges & Universities Distance
Colleges & Universities Distance
Univ. Southern Maine,Portland
Drive: 4 min 2.2 mi
Southern Maine Comm. Coll.
Drive: 12 min 6.2 mi
Univ. Southern Maine, Gorham
Drive: 22 min 12.6 mi
St. Joseph's College of Maine
Drive: 37 min 19.6 mi
Winchester Woods is within 4 minutes or 2.2 miles from Univ. Southern Maine,Portland. It is also near Southern Maine Comm. Coll. and Univ. Southern Maine, Gorham.
Schools
  • Public Schools
  • Private Schools
Presumpscot School
Public Elementary School
Grades PK-5
230 Students
Attendance Zone
Howard C Reiche Community School
Public Elementary School
Grades PK-5
427 Students
Attendance Zone
Lyman Moore Middle School
Public Middle School
Grades 6-8
482 Students
Attendance Zone
Portland High School
Public High School
Grades 9-12
952 Students
Attendance Zone
Casco Bay High School
Public High School
Grades 9-12
382 Students
Attendance Zone
Friends School Of Portland
Private Elementary & Middle School
Grades PK-8
119 Students
Nearby
Spurwink School-Cummings
Private Middle & High School
Grades 8-12
34 Students
Nearby
School data provided by The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.

View GreatSchools Rating Methodology


Data provided by GreatSchools.org © 2025. All rights reserved.
Transportation

Winchester Woods is near Portland International Jetport, located 5.4 miles or 11 minutes away.

Commuter Rail Distance
Commuter Rail Distance
Portland
Drive: 5 min 3.1 mi
Freeport Amtrak Station
Drive: 21 min 15.8 mi
Old Orchard Beach Amtrak
Drive: 25 min 17.6 mi
Saco Amtrak Station
Drive: 25 min 18.8 mi
Brunswick Amtrak Station
Drive: 33 min 25.0 mi
Airports Distance
Airports Distance
Portland International Jetport
Drive: 11 min 5.4 mi
Somewhat Walkable
57
Walk Score®
Out of 100
You might be able to get out and walk when living in this area. Some errands can be accomplished on foot, but for others you’ll need a car.
Some Transit
36
Transit Score®
Out of 100
You'll likely want a car when living in this area since it has few transit options.
Very Bikeable
70
Bike Score®
Out of 100
This area is very Bikeable. You’ll find a variety of bike paths and lanes.
-
-
Soundscore™
Out of 100

Traffic:

-

Airport:

-

Businesses:

-

Score provided by

Scores provided by  and

Score provided by

Points of Interest

Time and distance from Winchester Woods.

Shopping Centers Distance
Shopping Centers Distance
Congress Plaza
Drive: 3 min 1.8 mi
Century Plaza
Drive: 4 min 2.0 mi
Hannaford Plaza
Drive: 4 min 2.1 mi
Winchester Woods has 3 shopping centers within 2.1 miles, which is about a 4-minute drive. The miles and minutes will be for the farthest away property.
Parks and Recreation Distance
Parks and Recreation Distance
Portland Observatory
Drive: 3 min 1.7 mi
Maine Narrow Gauge Railroad
Drive: 4 min 1.9 mi
East End Beach and Eastern Prom Trail
Drive: 5 min 2.1 mi
Gilsland Farm Audubon Center
Drive: 5 min 2.4 mi
Southworth Planetarium
Drive: 4 min 2.4 mi
Winchester Woods has 5 parks within 2.4 miles, including Portland Observatory, East End Beach and Eastern Prom Trail, and Maine Narrow Gauge Railroad.
Hospitals Distance
Hospitals Distance
Northern Light Mercy Hospital
Drive: 5 min 2.9 mi
Maine Medical Center
Drive: 6 min 3.1 mi
Spring Harbor Hospital
Drive: 10 min 5.9 mi
Winchester Woods has 3 hospitals within 5.9 miles, the nearest is Northern Light Mercy Hospital which is 2.9 miles away and a 5 minute drive.
Military Bases Distance
Military Bases Distance
South Portland Coast Guard Base
Drive: 11 min 5.6 mi
Brunswick Naval Air Station
Drive: 40 min 31.6 mi
Portsmouth Naval Shipyard
Drive: 64 min 52.1 mi
Winchester Woods has 3 military bases within 52.1 miles, the nearest is South Portland Coast Guard Base which is 5.6 miles away and a 11 minute drive.
 
 

Property Ratings at Winchester Woods

How Is This Rating Determined? How Is This Rating Determined? Every community on Apartments.com features a rating displayed on a 5-star scale. This rating includes average renter review scores and a building rating to determine an overall blended score for this property.

Building ratings are based on this community’s features, including the building design, construction, exterior spaces, and amenities. To learn more about the CoStar Building Rating System, refer to our official guidelines here.
5.0
Excellent
Out of 5

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Winchester Woods Photos

  • Winchester Woods

  • 1BD, 1BA Unit

  • Primary Photo

  • 1BD, 1BA - Living Room/Dining Room

  • 1BD, 1BA - Living Room

  • 1BD, 1BA - Kitchen

Frequently Asked Questions
Does Winchester Woods have in-unit laundry?

Winchester Woods does not offer in-unit laundry or shared facilities. Please contact the property to learn about nearby laundry options.

What utilities are included in rent at Winchester Woods?

Utilities are not included in rent. Residents should plan to set up and pay for all services separately.

Which floor plans are available, and what are the price ranges?

Winchester Woods has one to two-bedrooms with rent ranges from $1,995/mo. to $2,516/mo.

Is Winchester Woods pet-friendly?

Winchester Woods does not allow pets, though service animals are always welcome in accordance with applicable laws.

How much income do I need to rent at Winchester Woods?

A good rule of thumb is to spend no more than 30% of your gross income on rent. Based on the lowest available rent of $1,995 for a one-bedroom, you would need to earn about $72,000 per year to qualify. Want to double-check your budget? Try our Rent Affordability Calculator to see how much rent fits your income and lifestyle.

Does Winchester Woods have move-in specials?

Winchester Woods is offering Specials for eligible applicants, with rental rates starting at $1,995.

Does Winchester Woods offer Matterport 3D tours?

Yes! Winchester Woods offers 2 Matterport 3D Tours. Explore different floor plans and see unit level details, all without leaving home.

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What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

Walk Score® measures the walkability of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address.

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What is a Sound Score Rating?

A Sound Score Rating aggregates noise caused by vehicle traffic, airplane traffic and local sources

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41 Winchester Dr

Portland, ME 04103

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