Why rent when you can own? Welcome to Callaway Commons - this unique standalone condo offers the best of both worlds, combining privacy with convenience. Tucked at the end of the road, the home enjoys a peaceful setting with a private backyard oasis, while remaining just minutes from the amenities of Westbrook, Portland and Windham. Inside, you'll find 1,552 square feet of living space across two levels, featuring a distinctive and flexible floor plan. The bright, open kitchen has been tastefully updated with new cabinetry, granite countertops and stainless steel appliances. It flows seamlessly into an eat in dining area with pantry and an inviting living room, perfect for everyday living and entertaining. Step outside to enjoy the elevated deck overlooking the spacious backyard. Additional highlights include an oversized two car garage and low maintenance living, with lawn care and snow removal included in the condo fee. A rare opportunity for comfort, convenience, and value - don't miss it.
Closed
$385,000
37 Callaway Drive #37, Westbrook, ME 04092
2beds
1,552sqft
Condominium
Built in 2005
-- sqft lot
$385,900 Zestimate®
$248/sqft
$2,718 Estimated rent
Home value
$385,900
$355,000 - $417,000
$2,718/mo
Zestimate® history
Owner options
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$2,736/mo
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$2,736/mo
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List your homeWhat's special
Oversized two car garageGranite countertopsPrivate backyard oasisBright open kitchenStainless steel appliancesTwo levels
Zillow last checked:
Listing updated:
Listed by:
Portside Real Estate Group
Bought with:
Allied Real Estate
Source: Maine Listings,MLS#: 1659600
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 1
- Full bathrooms: 1
Bedroom 1
- Features: Closet
- Level: First
Bedroom 2
- Features: Heat Stove
- Level: Second
Den
- Features: Closet, Vaulted Ceiling(s)
- Level: Second
Kitchen
- Features: Eat-in Kitchen
- Level: Second
Living room
- Level: Second
Heating
- Baseboard
Cooling
- None
Appliances
- Included: Dishwasher, Dryer, Microwave, Electric Range, Refrigerator, Washer
Features
- Flooring: Luxury Vinyl
- Has fireplace: No
Interior area
- Total structure area: 1,552
- Total interior livable area: 1,552 sqft
- Finished area above ground: 1,244
- Finished area below ground: 308
Property
Parking
- Total spaces: 2
- Parking features: Paved, 1 - 4 Spaces, Garage Door Opener
- Garage spaces: 2
Lot
- Size: 2.1 Acres
- Features: Near Town, Suburban, Level, Wooded
Details
- Parcel number: WSBR00002100000000002935
- Zoning: 20
Construction
Type & style
- Home type: Condo
- Architectural style: Colonial
- Property subtype: Condominium
Materials
- Wood Frame, Vinyl Siding
- Roof: Shingle
Condition
- Year built: 2005
Utilities & green energy
- Electric: Circuit Breakers
- Sewer: Private Sewer
- Water: Public
Community & HOA
HOA
- Has HOA: Yes
- HOA fee: $300 monthly
Location
- Region: Westbrook
Financial & listing details
- Price per square foot: $248/sqft
- Annual tax amount: $4,912
- Date on market: 4/28/2026
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 6/2/2026 | Sold | $385,000+4.3%$248/sqft |
Source:  Maine Listings #1659600 Report a problem | ||
| 5/8/2026 | Pending sale | $369,000$238/sqft |
Source: Maine Listings #1659600 Report a problem | ||
| 4/28/2026 | Listed for sale | $369,000$238/sqft |
Source: Maine Listings #1659600 Report a problem | ||
Public tax history
Tax history is unavailable.
Neighborhood: 04092
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Nearby schools
GreatSchools rating
- 3/10Congin SchoolGrades: PK-4Distance: 3.2 mi
- 4/10Westbrook Middle SchoolGrades: 5-8Distance: 4.9 mi
- 3/10Westbrook High SchoolGrades: 9-12Distance: 4.3 mi
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$385,900
2% more
+$7,718
With Zillow Showcase(estimated)
$393,618
- Maine
- Cumberland County
- Westbrook
- 04092
- 37 Callaway Drive Unit 37
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