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Winchester Woods Apartments

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(877) 706-9968
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41 Winchester Dr, Portland, ME 04103

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Winchester Woods

41 Winchester Dr
Portland, ME 04103
(877) 706-9968
Winchester Woods in Portland, ME - Building Photo
  • 1–2 Bedrooms
  • $1,722-$2,572 Pricing
  • 745–907 Square Feet

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 located in the East Deering Neighborhood and 04103 Zip code of Portland, ME. This community is professionally managed by Universal Property Management

Property Contact Info

Office Hours

MondayBy Appointment
TuesdayBy Appointment
WednesdayBy Appointment
ThursdayBy Appointment
FridayBy Appointment
SaturdayBy Appointment
SundayBy Appointment

Floorplan Pricing and Availability

Winchester Woods offers 1 to 2 Bedroom apartments starting from $1,722 and having 745–907 sq ft. Here is the current pricing and availability:

  • 1 Bedroom

    $2,068

    29-203

    1 Bed, 1 Bath, 745 sq ft
    $1,895 depositAvailable Now

    Availability Details

    PriceAvailability DateUnitSq FtDeposit
    $2,068Available Now29-203745$1,895

    Unit 29-203 Rent and Fees

    Unit Price

    • $2,068

    Deposit

    • $1,895 deposit

    $2,105

    17-103

    1 Bed, 1 Bath, 745 sq ft
    $2,080 depositAvailable Sep 5

    Availability Details

    PriceAvailability DateUnitSq FtDeposit
    $2,105 September 5, 202617-103745$2,080

    Unit 17-103 Amenities and Features

    Features

    • Air Conditioning
    • Cable Ready
    • Heating
    • Smoke Free
    • Tub/Shower
    • Washer/Dryer

    Kitchen

    • Freezer
    • Instant Hot Water
    • Island Kitchen
    • Kitchen
    • Microwave
    • Oven
    • Refrigerator
    • Stainless Steel Appliances

    Living Space

    • Carpet
    • Vinyl Flooring

    Unique Features

    • Free Parking, Snow Removal.

    Unit 17-103 Rent and Fees

    Unit Price

    • $2,105

    Deposit

    • $2,080 deposit

    $1,722

    48-103

    1 Bed, 1 Bath, 745 sq ft
    Available Sep 15

    Availability Details

    PriceAvailability DateUnitSq Ft
    $1,722 September 15, 202648-103745

    Unit 48-103 Rent and Fees

    Unit Price

    • $1,722
  • 2 Bedrooms

    Two Bedroom

    From $2,295

    2 Beds, 1 Bath, 907 sq ft
    Available Now

    Availability Details

    PriceAvailability DateUnitSq Ft
    From $2,295Available NowTwo Bedroom907 sq ft

    Model Amenities and Features

    Features

    • Air Conditioning
    • Heating
    • Tub/Shower

    Kitchen

    • Instant Hot Water
    • Kitchen
    • Oven
    • Range
    • Refrigerator
    • Stainless Steel Appliances

    Model Rent and Fees

    Model Price Range

    • $2,295 - $2,572

    $1,949

    More 2 bedroom units

    2 Beds, 1 Bath, 907 sq ft
    Available Now

    Availability Details

    PriceAvailability DateUnitSq Ft
    $1,949Available Now48-204907

    Unit 48-204 Rent and Fees

    Unit Price

    • $1,949
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.

Schedule a Tour

Request Tour
Call us at: (877) 706-9968 to request a tour.

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Property Information

  • 48 Units
  • 3 Stories
  • Built in 2023

Lease Terms

  • 12 mo

Fees and Policies

The fees listed below are community-provided and may exclude utilities or add-ons. All payments are made directly to the property and are non-refundable unless otherwise specified.

Required Fees

One-Time Basics

Due at Application
Application Fee Per ApplicantiCharged per applicant.$0.00
Due at Move-In
Administrative FeeiCharged per unit.$300.00

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.

Features and Amenities

Recreation and Fitness

  • Walking/Biking Trails

Interior Features

  • Tub/Shower
  • Heating
  • Air Conditioning

Kitchen Amenities

  • Oven
  • Range
  • Refrigerator
  • Stainless Steel Appliances
  • Instant Hot Water
  • Kitchen

Living Area Features

  • Carpet

Outdoor Features

  • Lawn
Google Map

Map

41 Winchester Dr, Portland, ME 04103

Getting Around

  • 60 / 100 Moderately walkable

    Most day-to-day needs are within walking distance

  • 30 / 100 Limited public transit

    Transit is available for some trips

  • 50 / 100 Fairly bikeable

    Somewhat suitable for bicycle commuting and/or recreation

  • 90 / 100 Exceptionally car friendly

    Excellent access to freeways and/or major arteries, with almost no chance of parking problems

Scores provided by Local Logic details

Getting to Know the Area

  • 70 / 100 Restaurants

    Variety of restaurants within a few minutes

  • 60 / 100 Cafes

    Variety of cafés within a few minutes

  • 70 / 100 Nightlife

    Several bars within a few minutes

  • 60 / 100 Shopping

    Several shops within a few minutes

  • 50 / 100 Noise Level

    Some sources of noise nearby

Scores provided by Local Logic

Frequently Asked Questions about Winchester Woods

Where is Winchester Woods located?

Winchester Woods is located at 41 Winchester Dr near the East Deering area of Portland, ME

What is the current rent range at Winchester Woods?

1 Bedroom to 2 Bedroom Apartments at Winchester Woods currently range from $1,722 to $2,105

When is the leasing office open?

  • The office Hours for Winchester Woods are
  • Monday By Appointment
  • Tuesday By Appointment
  • Wednesday By Appointment
  • Thursday By Appointment
  • Friday By Appointment
  • Saturday By Appointment
  • Sunday By Appointment

Are pets allowed?

Call us today to find out our pet policy and if we allow pets

Lifestyle Ratings

  • Affordability Nice Value3.0

    The Winchester Woods Apartments are 3.8% more expensive than the average apartment in the East Deering area.

    Rent Comparison to the East Deering Neighborhood

    FloorplanLowest Price HereNeighborhood Avg RentNbhd Avg RentCost Difference%
    2 Bedroom$2,295$2,210+$853.8%

    Methodology: On 08/03/2026, ApartmentHomeLiving.com compared current rents by floorplan to 74 other apartment communities in the immediate area around Winchester Woods (East Deering) using today’s up-to-date pricing using the sum/count averaging formula. This data will be updated in real-time as prices fluctuate.

    Rent Pricing Data as of 08/03/2026

Learn more about Lifestyle Search

Nearby Schools

Presumpscot School

Portland Public Schools
69 Presumpscot Street
Public School - Grades PK-5 (266 Students)
In Attendance Zone1 minute drive / 0.1 miles away
5/10

Portland High School

Portland Public Schools
284 Cumberland Avenue
Public School - Grades 9-12 (912 Students)
In Attendance Zone5 minute drive / 1.7 miles away
4/10

Casco Bay High School

Portland Public Schools
196 Allen Avenue
Public School - Grades 9-12 (382 Students)
In Attendance Zone4 minute drive / 2.0 miles away
5/10

Howard C Reiche Community School

Portland Public Schools
166 Brackett Street
Public School - Grades PK-5 (427 Students)
In Attendance Zone4 minute drive / 2.3 miles away
3/10

Lyman Moore Middle School

Portland Public Schools
171 Auburn Street
Public School - Grades 6-8 (482 Students)
In Attendance Zone4 minute drive / 2.2 miles away
4/10
School data provided by GreatSchools.
details
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 scale of 1 (below average) and 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 needs as part of the school selection process.

About GreatSchools Data on ApartmentHomeLiving.com.

Points of Interest

Time and distance from Winchester Woods.

Big Box and Retail

Walgreens

340 Allen Ave
5 minute drive / 1.98 miles away

Kohl's

41 Main St
7 minute drive / 3.57 miles away

Macy's

100 Maine Mall Rd
10 minute drive / 4.85 miles away

Colleges and Universities

University of Southern Maine - Portland Campus

96 Falmouth St
4 minute drive / 1.48 miles away

Southern Maine Community College - South Portland Campus

2 Fort Rd
5 minute drive / 2.73 miles away

University of Southern Maine - Gorham Campus

149 State Street
20 minute drive / 9.41 miles away

Groceries

Trader Joe's

87 Marginal Way
3 minute drive / 1.28 miles away

Market Basket

100-200 Market St
15 minute drive / 7.35 miles away

Hospitals

Northern Light Mercy Hospital

144 State Street
5 minute drive / 1.95 miles away

Maine Medical Center

22 Bramhall St
4 minute drive / 2.06 miles away

Spring Harbor Hospital

123 Andover Road
9 minute drive / 4.33 miles away

Military Bases

South Portland Coast Guard Base

5 minute drive / 2.52 miles away

Shopping Centers

Hannaford Plaza

295 Forest Ave
3 minute drive / 1.2 miles away

449 Forest Ave Plaza

449-471 Forest Ave
3 minute drive / 1.27 miles away

Congress Plaza

290 Congress St
4 minute drive / 1.36 miles away

Winchester Woods has 5 shopping centers within 2.1 miles.

Nearby Neighborhoods

East Deering

Studio to 4 Bedroom Apartments from $1,174
View Rentals

Back Cove

Studio to 4 Bedroom Apartments from $1,174
View Rentals

Oakdale

Studio to 4 Bedroom Apartments from $1,150
View Rentals

Rental Price Ranges in the Area

BedroomAverage RentCheapest RentHighest Rent
Portland Studio Apartments $2,111$1,174$3,558
Portland 1 Bedroom Apartments $2,290$1,275$4,048
Portland 2 Bedroom Apartments $2,494$1,516$4,113
Portland 3 Bedroom Apartments $2,693$1,150$4,500
Portland 4 Bedroom Apartments $3,133$3,000$3,200
2 Bedroom Homes$2,617$1,600$4,500
3 Bedroom Homes$3,377$1,450$6,200
4 Bedroom Homes$3,942$1,600$10,000+
5 Bedroom Homes$14,500$10,000$10,000+

Browse Top Apartments in Portland

Viewing: Winchester Woods | Desktop Version | Listing Updated: 08/01/2026 | AHLGLD