# 29 Smiley Avenue, Winslow, ME 04901

> **TL;DR:** 4bd/2ba single family, $289,900 ($212/sqft), built 1967, 1,368 sqft.
> Fireplace, A/C. Est. $1,551/mo.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $289,900 |
| Price/sqft | $212 |
| Bedrooms | 4 |
| Bathrooms | 1 full, 1 half |
| Square Feet | 1,368 |
| Year Built | 1967 |
| Lot Size | 35,284 sqft (0.81 acres) |
| Property Type | Single Family (Single Family Residence) |
| Status | Active |
| Days on Market | 0 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $1,466 |
| Estimated Insurance | $85 |
| **Total** | **$1,551** |

## Key Amenities

- Fireplace
- A/C

## Property Highlights

- Built in 1967
- 0.81 acre lot
- Fireplace

## Description

### Agent Description
Welcome home to this 4-bedroom, 1.5-bath ranch-style property located on generous double lot, this home offers plenty of room both inside and out. Enjoy hardwood floors, a spacious layout perfect for entertaining family and friends, and a large backyard deck ideal for summer barbecues and outdoor gatherings. The full basement provides ample storage or potential for additional living space. With an expansive yard surrounding the home, you'll have endless opportunities for gardening, recreation, or creating your own outdoor oasis.

## Location

- **Address:** 29 Smiley Avenue, Winslow, ME 04901
- **County:** Kennebec
- **Coordinates:** 44.549001, -69.606022
- **Google Maps:** https://www.google.com/maps?q=44.549001,-69.606022

## Listing Agent

- **Name:** Jessica Fike
- **Brokerage:** Brookewood Realty
- **Phone:** 2074589108
- **Broker Phone:** (207) 458-5600
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/29-Smiley-Ave_Winslow_ME_04901_M40606-88390?f=listhub&s=MREISME&m=1667295&c=propsimple)

## Photos

![29 Smiley Avenue - Photo 1](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f1011678662r.jpg)

![29 Smiley Avenue - Photo 2](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f2200797887r.jpg)

![29 Smiley Avenue - Photo 3](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f1725876742r.jpg)

![29 Smiley Avenue - Photo 4](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f3322986633r.jpg)

![29 Smiley Avenue - Photo 5](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f940497472r.jpg)

![29 Smiley Avenue - Photo 6](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f2873120764r.jpg)

![29 Smiley Avenue - Photo 7](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f2079810794r.jpg)

![29 Smiley Avenue - Photo 8](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f1601938708r.jpg)

![29 Smiley Avenue - Photo 9](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f441058321r.jpg)

![29 Smiley Avenue - Photo 10](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f2725899928r.jpg)

![29 Smiley Avenue - Photo 11](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f3441411894r.jpg)

![29 Smiley Avenue - Photo 12](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f1455206358r.jpg)

![29 Smiley Avenue - Photo 13](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f3881196834r.jpg)

![29 Smiley Avenue - Photo 14](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f4220584612r.jpg)

![29 Smiley Avenue - Photo 15](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f2933643105r.jpg)

![29 Smiley Avenue - Photo 16](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f2784791314r.jpg)

![29 Smiley Avenue - Photo 17](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f3887833426r.jpg)

![29 Smiley Avenue - Photo 18](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f3469348513r.jpg)

![29 Smiley Avenue - Photo 19](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f2886658287r.jpg)

![29 Smiley Avenue - Photo 20](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f1961821381r.jpg)

![29 Smiley Avenue - Photo 21](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f3327790730r.jpg)

![29 Smiley Avenue - Photo 22](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f2750380935r.jpg)

![29 Smiley Avenue - Photo 23](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f642836760r.jpg)

![29 Smiley Avenue - Photo 24](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f2708695215r.jpg)

![29 Smiley Avenue - Photo 25](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f3278134160r.jpg)

![29 Smiley Avenue - Photo 26](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f1534644028r.jpg)

![29 Smiley Avenue - Photo 27](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f3772095200r.jpg)

![29 Smiley Avenue - Photo 28](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f3088395003r.jpg)

![29 Smiley Avenue - Photo 29](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f3390585408r.jpg)

![29 Smiley Avenue - Photo 30](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f4078592993r.jpg)

![29 Smiley Avenue - Photo 31](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f2314722688r.jpg)

![29 Smiley Avenue - Photo 32](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f2493375496r.jpg)

![29 Smiley Avenue - Photo 33](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f2074865820r.jpg)

![29 Smiley Avenue - Photo 34](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f3143766617r.jpg)

![29 Smiley Avenue - Photo 35](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f1615407153r.jpg)

![29 Smiley Avenue - Photo 36](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f1240173576r.jpg)

![29 Smiley Avenue - Photo 37](http://lh.rdcpix.com/03f987f1df2e8287703cac9be0b5ead3l-f2986883068r.jpg)

---

**MLS#:** 1667295 | **Updated:** 2026-08-28
**Source:** listhub

*Copyright © 2026 Maine Listings. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.ai/listing/29-smiley-avenue-winslow-me-04901-1667295)

---

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