Are yards well-kept in Madison, ME?

As of early 2026, 100% of users say yards are well-kept

Is parking easy in Madison, ME?

As of early 2026, 86% of users say parking is easy

Do kids play outside in Madison, ME?

As of early 2026, 86% of users say kids play outside

Is Madison, ME dog-friendly?

As of early 2026, 83% of users say it's dog friendly

Does Madison, ME show holiday spirit?

As of early 2026, 75% of users say there's holiday spirit

Do residents of Madison, ME plan to stay at least 5 years?

As of early 2026, 75% of users say they plan to stay for at least 5 years

Is a car needed in Madison, ME?

As of early 2026, 71% of users say car is needed

Would people walk alone at night in Madison, ME?

As of early 2026, 70% of users say people would walk alone at night

Are neighbors friendly in Madison, ME?

As of early 2026, 67% of users say neighbors are friendly

Does Madison, ME have sidewalks?

As of early 2026, 63% of users say there are sidewalks

Are the streets well-lit in Madison, ME?

As of early 2026, 63% of users say streets are well-lit

Is Madison, ME walkable to grocery stores?

As of early 2026, 60% of users say it's walkable to grocery stores

Is there wildlife in Madison, ME?

As of early 2026, 54% of users say there's wildlife

Is Madison, ME walkable to restaurants?

As of early 2026, 50% of users say it's walkable to restaurants

Are there community events in Madison, ME?

As of early 2026, 44% of users say there are community events

Is Madison, ME quiet?

As of early 2026, 40% of users say it's quiet

OFF MARKET

5 Winter St
Madison, ME 04950

Studio
2 Baths
1,092 sqft (on 1.40 acres)

$258,300

Trulia Estimate

as of Jul 28, 2026

Est. Refi. Payment $1,645/mo*

Refinance Your Home

$258,300

Trulia Estimate

as of Jul 28, 2026

Est. Refi. Payment $1,645/mo*

Refinance Your Home

Studio

2 Baths

1,092 sqft

(on 1.40 acres)

Local Information

Map ViewExplore the area around 5 Winter St.
Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1984

Lot Size

1.4 acres

Living Area

1,092 sqft

Price/Sqft

$237

Parking

Garage

About this House

This single-family home is located at 5 Winter St, Madison, ME. 5 Winter St is in Madison, ME and in ZIP code 04950. This property has 2 bathrooms and approximately 1,092 sqft of floor space. This property has a lot size of 1.40 acres and was built in 1984.

5 Winter St, Madison, ME 04950 is a studio, 2 bathroom, 1,092 sqft single-family home built in 1984. It is currently off market. The Trulia Estimate is $258,300, with a rent estimate of $1,631/month.

Home Details for 5 Winter St

Property Information
Year Built Year Built: 1984
Property Type / Style Property Type: Single Family Home

Exterior Features
Pool Pool
Parking & Garage GarageParking: Garage Attached

Lot Information
Lot Area: 1.40 acres

Market trends in Madison

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

8MoM

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Property Tax and Assessment

Year	2024
Tax	$2,853
Assessment	$177,200

Home facts updated by county records

Comparable Sales for 5 Winter St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
56 Myrtle Street, Madison, ME	0.15	Single-Family Home	$293,000	08/22/25	3	2	1,532
174 Old Point Avenue, Madison, ME	0.44	Single-Family Home	$240,000	03/09/26	2	2	1,100
9 Locust Street, Madison, ME	0.17	Single-Family Home	$212,000	09/19/25	3	1.5	1,183
26 Jones Street, Madison, ME	0.27	Single-Family Home	$209,900	08/01/25	3	1	1,104
11 Ash Street, Madison, ME	0.10	Single-Family Home	$271,350	12/22/25	3	2	2,176
83 Preble Avenue, Madison, ME	0.19	Single-Family Home	$270,000	05/29/26	2	1	1,152
76 Pine Street, Madison, ME	0.26	Single-Family Home	$229,000	10/03/25	3	2	1,300
20 Spruce Street, Madison, ME	0.11	Single-Family Home	$312,900	09/04/25	3	3	2,182
81 Nichols Street, Madison, ME	0.42	Single-Family Home	$212,000	07/10/26	2	1	800
24 Locust Street, Madison, ME	0.13	Single-Family Home	$285,000	03/26/26	5	2.5	1,878

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Est. $199,200
3 bd
1 ba
1,092 sqft
8 Winter Street,
Madison, ME 04950
Palmer Realty Group, Closed
OFF MARKET
Est. $224,900
3 bd
1 ba
1,040 sqft
28 Winter Street,
Madison, ME 04950
Better Homes & Gardens Real Estate/The Masiello Group, Closed
OFF MARKET
Est. $213,000
3 bd
1 ba
1,120 sqft
66 Preble Avenue,
Madison, ME 04950
Allied Realty, Closed
SOLD
MAR 6, 2026
$40,000
0000 Winter Street,
Madison, ME 04950
Allied Realty, Closed
SOLD
DEC 22, 2025
$271,350
3 bd
2 ba
2,176 sqft
11 Ash Street,
Madison, ME 04950
Allied Realty, Closed
OFF MARKET
Est. $217,800
2 bd
1 ba
864 sqft
4 Summer Street,
Madison, ME 04950
Allied Realty, Closed
OFF MARKET
Est. $276,300
2 bd
1 ba
1,175 sqft
68 Preble Avenue,
Madison, ME 04950
Allied Realty, Closed
OFF MARKET
Est. $325,200
3 bd
3 ba
2,182 sqft
20 Spruce Street,
Madison, ME 04950
Allied Realty, Closed
OFF MARKET
Est. $252,900
3 bd
1 ba
1,634 sqft
16 Locust Street,
Madison, ME 04950
Allied Realty, Closed
SOLD
MAR 26, 2026
$285,000
5 bd
2.5 ba
1,878 sqft
24 Locust Street,
Madison, ME 04950
Allied Realty, Closed
OFF MARKET
Est. $227,800
4 bd
1.5 ba
2,056 sqft
17 Spring Street,
Madison, ME 04950
Century 21 Nason Realty, Closed
OFF MARKET
Est. $169,300
3 bd
1 ba
788 sqft
20 Summer Street,
Madison, ME 04950
Coldwell Banker Plourde Real Estate, Closed

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Additional Cost

Assigned Schools

These are the assigned schools for 5 Winter St.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Madison

At least 6 Trulia users voted on each feature.

100 % Say yards are well-kept
86 % Say parking is easy
86 % Say kids play outside
83 % Say it's dog friendly
75 % Say there's holiday spirit
75 % Say they plan to stay for at least 5 years
71 % Say car is needed
70 % Say people would walk alone at night
67 % Say neighbors are friendly
63 % Say there are sidewalks
63 % Say streets are well-lit
60 % Say it's walkable to grocery stores
54 % Say there's wildlife
50 % Say it's walkable to restaurants
44 % Say there are community events
40 % Say it's quiet

Sourced by Trulia users. Learn more about our methodology.

Amandaroy14
Resident
6y ago
"Many families in Area, good schools, friendly townspeople, nice town events, old down home feeling to it "
1
Flag
Trulia User
Resident
6y ago
"I’ve seen a woman drive into the neighborhood and let her older dog out of the car to do his business. 2x’s so far."
0
Flag
Sharyn
15y ago
"Great area for recreation year round: boating, fishing, snow mobiling, skiing nearby, golf, summer theatre, involved summer community. Small town feeling. "
0
Flag

LGBTQ Local Legal Protections

Apartments for Rent

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$900 - $1,290/mo
Studio-1 bd
1 ba
55 Weston Ave LLC | 55 Weston Ave,
Madison, ME 04950
Dooryard Management LLC
APPLY INSTANTLY
FURNISHED
$1,400/mo
1 bd
1 ba
8 Thomas St #1B,
Madison, ME 04950
APPLY INSTANTLY
PET FRIENDLY
$975/mo
2 bd
1 ba
49 Madison Ave #2,
Madison, ME 04950
APPLY INSTANTLY
FURNISHED
$1,400/mo
1 bd
1 ba
8 Thomas St #2A,
Madison, ME 04950
FURNISHED
$240/mo
8 bd
1 ba
327 Shusta Rd #1,
Madison, ME 04950
Home Deals of Maine
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Madison
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Homes for sale near 5 Winter St

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0.25 ACRES
$195,000
2 bd
1.5 ba
735 sqft
8 Fern Street,
Madison, ME 04950
Keller Williams Realty, Active
0.27 ACRES
$130,000
4 bd
1.5 ba
2,150 sqft
13 Heald Street,
Madison, ME 04950
Allied Realty, Active
0.26 ACRES
$109,900
3 bd
2 ba
1,700 sqft
15 Garfield Street,
Madison, ME 04950
Sprague & Curtis Real Estate, Active
$189,000
3 bd
1 ba
1,092 sqft
17 Bean Street,
Madison, ME 04950
Coldwell Banker Plourde Real Estate, Active
0.25 ACRES
$299,000
5 bd
3 ba
3,273 sqft
16 Park Street,
Madison, ME 04950
LAER, Active
$234,000
4 bd
1 ba
2,128 sqft
7 Bean Street,
Madison, ME 04950
Allied Realty, Active
AUCTION
0.37 ACRES
Est. $183,400
3 bd
1 ba
768 sqft
132 Weston Ave,
Madison, ME 04950
0.5 ACRES
$235,000
3 bd
1 ba
1,200 sqft
189 Shusta Road,
Madison, ME 04950
The Maine Real Estate Experience, Active
$150,000
2 bd
1 ba
1,000 sqft
22 Highland Avenue,
Anson, ME 04911
LPT Realty, Active
32.3 ACRES
$465,000
4 bd
1.5 ba
2,324 sqft
139 Lloyd Road,
Anson, ME 04911
Real Broker, Active
See more homes for sale in
Madison
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Off Market Homes Near 5 Winter St

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SOLD
JUL 10, 2026
$212,000
2 bd
1 ba
800 sqft
81 Nichols Street,
Madison, ME 04950
Real Broker, Closed
SOLD
JUL 9, 2026
$290,000
2 bd
2 ba
880 sqft
285 Ward Hill Road,
Madison, ME 04950
Summit Real Estate, Closed
SOLD
JUN 30, 2026
$270,000
4 bd
2 ba
1,820 sqft
8 Spring Street,
Madison, ME 04950
LAER, Closed
SOLD
JUN 29, 2026
$375,000
8 bd
9 ba
4,400 sqft
69 Main Street,
Madison, ME 04950
Allied Realty, Closed
SOLD
JUN 18, 2026
$203,000
3 bd
1 ba
928 sqft
6 Myrtle Street,
Madison, ME 04950
Keller Williams Realty, Closed
SOLD
JUN 2, 2026
$229,900
2 bd
1 ba
1,518 sqft
88 Pine Street,
Madison, ME 04950
Real Broker, Closed
SOLD
MAY 29, 2026
$270,000
2 bd
1 ba
1,152 sqft
83 Preble Avenue,
Madison, ME 04950
Keller Williams Realty, Closed
SOLD
MAY 22, 2026
$168,840
4 bd
1 ba
1,951 sqft
95 Main Street,
Anson, ME 04911
Allied Realty, Closed
SOLD
APR 28, 2026
$199,000
5 bd
2 ba
2,564 sqft
75 Madison Avenue,
Madison, ME 04950
Coldwell Banker Plourde Real Estate, Closed
SOLD
APR 23, 2026
$260,000
3 bd
1.5 ba
1,700 sqft
51 Maple Street,
Madison, ME 04950
Keller Williams Realty, Closed
See more homes for sale in
Madison
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5 Winter St
Madison, ME 04950

$258,300

$258,300