Is a car needed in Naples, ME?

As of early 2026, 100% of users say car is needed

Are yards well-kept in Naples, ME?

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

Is parking easy in Naples, ME?

As of early 2026, 93% of users say parking is easy

Does Naples, ME show holiday spirit?

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

Is there wildlife in Naples, ME?

As of early 2026, 73% of users say there's wildlife

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

As of early 2026, 63% of users say they plan to stay for at least 5 years

As of early 2026, 60% of users say it's quiet

Are neighbors friendly in Naples, ME?

As of early 2026, 55% of users say neighbors are friendly

Is Naples, ME dog-friendly?

As of early 2026, 55% of users say it's dog friendly

Is Naples, ME walkable to restaurants?

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

Do kids play outside in Naples, ME?

As of early 2026, 47% of users say kids play outside

Would people walk alone at night in Naples, ME?

As of early 2026, 45% of users say people would walk alone at night

Are there community events in Naples, ME?

As of early 2026, 40% of users say there are community events

Is Naples, ME walkable to grocery stores?

As of early 2026, 29% of users say it's walkable to grocery stores

Are the streets well-lit in Naples, ME?

As of early 2026, 27% of users say streets are well-lit

What is 39 Windsor Green Rd estimated to be worth?

Trulia's estimated value for 39 Windsor Green Rd in Naples, ME is $541,300 .

Is Naples a buyer's or seller's market?

Naples is currently a seller's market, based on recent for-sale activity.

What do residents say about Naples?

Residents describe Naples, ME as well-kept, easy to park in, and established. Most residents say you need a car. See recently sold homes in Naples, ME .

What are the closest schools to 39 Windsor Green Rd?

The closest schools to 39 Windsor Green Rd in Naples, ME are Lake Region High School (rated 4/10), Lake Region Middle School (rated 3/10), Songo Locks School (Pre-K/Elementary).

How big is the lot at 39 Windsor Green Rd?

The lot at 39 Windsor Green Rd in Naples, ME is about 1 acre .

OFF MARKET

$541,300

Trulia Estimate

Studio
726 sqft (on 1 acre)

39 Windsor Green Rd, Naples, ME 04055

Refinance Your Home

Home Value

Trulia Estimate

$541K

Since last month

$23K (-4%)

Since last year

$54K (+11%)

Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +33% in the last 10 years

Month	Estimated value
2026
August 2026	$541K
August 2026	$540K
July 2026	$564K
June 2026	$569K
May 2026	$501K
April 2026	$497K
March 2026	$489K
February 2026	$469K
January 2026	$467K
2025
December 2025	$472K
November 2025	$475K
October 2025	$476K
September 2025	$494K
August 2025	$488K
July 2025	$502K
June 2025	$497K
May 2025	$513K
April 2025	$484K
March 2025	$503K
February 2025	$480K
January 2025	$482K
2024
December 2024	$484K
November 2024	$455K
October 2024	$579K
September 2024	$595K
August 2024	$599K
July 2024	$584K
June 2024	$616K
May 2024	$596K
April 2024	$584K
March 2024	$539K
February 2024	$548K
January 2024	$542K
2023
December 2023	$552K
November 2023	$515K
October 2023	$542K
September 2023	$553K
August 2023	$555K
July 2023	$553K
June 2023	$567K
May 2023	$421K
April 2023	$400K
March 2023	$395K
February 2023	$378K
January 2023	$372K
2022
December 2022	$392K
November 2022	$421K
October 2022	$431K
September 2022	$429K
August 2022	$434K
July 2022	$435K
June 2022	$432K
May 2022	$437K
April 2022	$422K
March 2022	$405K
February 2022	$389K
January 2022	$406K

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
29 Windsor Green Rd, Naples, ME	0.04	Single-Family Home	$700,000	05/28/26		-	726
6 Excalibur Ct, Naples, ME	0.11	Single-Family Home	$774,000	05/22/26	4	2.5	2,350
4 Quiet Cove Ln, Naples, ME	0.35	Single-Family Home	$375,000	03/03/26		-	840
589 Roosevelt Trail, Naples, ME	0.27	Single-Family Home	$510,000	10/28/25	3	2	1,775
4 Goodridge Dr, Naples, ME	0.63	Single-Family Home	$810,000	08/18/26		-	890
7 Goodridge Dr, Naples, ME	0.64	Single-Family Home	$840,000	09/19/25		-	890
19 Goodridge Dr, Naples, ME	0.64	Single-Family Home	$824,900	07/02/26		-	890
12 Bay Village Rd, Naples, ME	0.37	Single-Family Home	$645,000	12/01/25	3	1.5	1,728
31 Knight Drive, Naples, ME	0.60	Single-Family Home	$390,875	01/02/26	3	2	1,237
750 Roosevelt Trail #7, Naples, ME	0.56	Single-Family Home	$338,500	04/13/26	2	1	400

Nearby home prices

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

Address	Distance	Price	Bed	Bath	Sqft	Status
9 Guinevere Court #9, Naples, ME 04055	0.04	$609,200	3	2.5	1,484	Off Market
7 Guinevere Court #7, Naples, ME 04055	0.05	$706,500	2	2.5	1,584	Off Market
29 Winsor Green Road #29, Naples, ME 04055	0.05	$700,000	2	2.5	1,376	Recently Sold
37 Winsor Green Road #30, Naples, ME 04055	0.06	$582,600	2	2.5	1,969	Off Market
22 Lancelot Road #22, Naples, ME 04055	0.08	$533,700	2	2.5	1,600	Off Market
7 Scenic View Drive, Naples, ME 04055	0.09	$1,728,500	3	2	1,842	Off Market
17 Winsor Green Road #23, Naples, ME 04055	0.10	$496,500	2	2.5	1,600	Off Market
14 Lancelot Road #14, Naples, ME 04055	0.11	$639,000	3	2.5	2,376	For Sale
7 Excalibur Court #7, Naples, ME 04055	0.10	$846,700	2	3	2,934	Off Market
16 Scenic View Drive, Naples, ME 04055	0.12	$799,999	4	2.5	1,525	For Sale
6 Excalibur Court #37, Naples, ME 04055	0.15	$774,000	4	2.5	2,744	Recently Sold
Lot U10-40 Scenic View Drive, Naples, ME 04055	0.23	-	-	-	-	Off Market

Local Information

Map ViewExplore the area around 39 Windsor Green Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

1 acre lot

726 sqft

$746/sqft

About this House

This single-family home is located at 39 Windsor Green Rd, Naples, ME. 39 Windsor Green Rd is in Naples, ME and in ZIP code 04055. This property has approximately 726 sqft of floor space. This property has a lot size of 1 acre.

39 Windsor Green Rd, Naples, ME 04055 is a studio, 726 sqft single-family home. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $541,300, with a rent estimate of $2,771/month.

Home Details for 39 Windsor Green Rd

Interior Features
Levels, Entrance, & Accessibility Stories: 2

Property Information
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 1 acre

Price and Tax history

Year	Property tax	Tax assessment
2024	$4,163	$447,599

Home facts updated by county records

Additional Cost

Market trends in Naples

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

6MoM

Around this home

Songo Locks School
PK-2
Public
249 Students
Regional School Unit 61 Msad 61
NA
GreatSchools Rating
Parent Rating Average
Do not pick this school district if you have a special needs child. They do not work with you what so ever. They approach your child as a “bad kid” when they aren’t a “normal” child. I’ve had the principal call me asking why my child wasn’t acting like a normal first grader. The teacher are essentially forced to stay quiet during IEP meetings, leaving your child lacking the accommodations they need for a successful year. There are teachers that work there sending their elementary age kids to other charter schools around. I do not recommend.
Parent Review
10mo ago
7 Reviews

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 Naples

At least 10 Trulia users voted on each feature.

100 % Say car is needed
100 % Say yards are well-kept
93 % Say parking is easy
75 % Say there's holiday spirit
73 % Say there's wildlife
63 % Say they plan to stay for at least 5 years
60 % Say it's quiet
55 % Say neighbors are friendly
55 % Say it's dog friendly
50 % Say it's walkable to restaurants
47 % Say kids play outside
45 % Say people would walk alone at night
40 % Say there are community events
29 % Say it's walkable to grocery stores
27 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.

Cjw.plymouth
Visitor
6y ago
"Not many sidewalks on roads outside of the main strip off long lake. Lots of the roads leading out of town are busy state roads that are also windy and for instance I noticed while driving that joggers can’t always been seen around corners."
8
Flag
Rrbygib
Resident
6y ago
"Naples has a lot to offer, from summer water sports, such as boating and swimming,to winter sports, skiing, snowshoeing, ice fishing, snowmobiling.....and the area is magical. "
2
Flag

LGBTQ Local Legal Protections

Frequently asked questions about 39 Windsor Green Rd

What is 39 Windsor Green Rd estimated to be worth?
Trulia's estimated value for 39 Windsor Green Rd in Naples, ME is $541,300.
Is Naples a buyer's or seller's market?
Naples is currently a seller's market, based on recent for-sale activity.
What do residents say about Naples?
Residents describe Naples, ME as well-kept, easy to park in, and established. Most residents say you need a car. See recently sold homes in Naples, ME.
What are the closest schools to 39 Windsor Green Rd?
The closest schools to 39 Windsor Green Rd in Naples, ME are Lake Region High School (rated 4/10), Lake Region Middle School (rated 3/10), Songo Locks School (Pre-K/Elementary).
How big is the lot at 39 Windsor Green Rd?
The lot at 39 Windsor Green Rd in Naples, ME is about 1 acre.

Explore by feature - Air Conditioning

APPLY INSTANTLY
FURNISHED
$2,250/mo
2 bd
1 ba
1,250 sqft
10 Burke Rd,
Naples, ME 04055
APPLY INSTANTLY
$3,500/mo
5 bd
2 ba
1,700 sqft
Address Not Disclosed,
Naples, ME 04055
APPLY INSTANTLY
PET FRIENDLY
FURNISHED
$2,000/mo
2 bd
1 ba
1,300 sqft
50 Harrison Rd,
Naples, ME 04055
Maine A La Carte Real Estate LLC
APPLY INSTANTLY
FURNISHED
$2,500/mo
3 bd
1.5 ba
1,728 sqft
12 Bay Village Rd,
Naples, ME 04055
Maine A La Carte Real Estate LLC
APPLY INSTANTLY
FURNISHED
$3,000/mo
Total price
3 bd
2 ba
1,064 sqft
3 Autumn St,
Naples, ME 04055

Explore by feature - Washer/dryer

APPLY INSTANTLY
FURNISHED
$2,250/mo
2 bd
1 ba
1,250 sqft
10 Burke Rd,
Naples, ME 04055
APPLY INSTANTLY
PET FRIENDLY
FURNISHED
$2,000/mo
2 bd
1 ba
1,300 sqft
50 Harrison Rd,
Naples, ME 04055
Maine A La Carte Real Estate LLC
APPLY INSTANTLY
FURNISHED
$2,500/mo
3 bd
1.5 ba
1,728 sqft
12 Bay Village Rd,
Naples, ME 04055
Maine A La Carte Real Estate LLC
APPLY INSTANTLY
FURNISHED
$3,000/mo
Total price
3 bd
2 ba
1,064 sqft
3 Autumn St,
Naples, ME 04055
PET FRIENDLY
$1,250/mo
4 bd
3 ba
15 Krainin Ln,
Naples, ME 04055

Apartments for Rent

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Off Market Homes Near 39 Windsor Green Rd

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SOLD
AUG 28, 2026
$329,900
3 bd
1 ba
1,210 sqft
29 Bear Pine Drive,
Casco, ME 04015
Kern Real Estate, Closed
SOLD
AUG 27, 2026
$340,000
3 bd
1.5 ba
1,547 sqft
1328 Roosevelt Trail,
Naples, ME 04055
Hearth & Key Realty, Closed
SOLD
AUG 26, 2026
$380,000
2 bd
2 ba
960 sqft
1617 Pine Drive,
Casco, ME 04015
Leading Edge Real Estate, Closed
SOLD
AUG 25, 2026
$375,000
3 bd
2 ba
1,288 sqft
301 Chaplins Mill Rd,
Naples, ME 04055
SOLD
AUG 24, 2026
$650,000
3 bd
3 ba
2,582 sqft
79 Lukes Road,
Casco, ME 04015
Keller Williams Realty, Closed
SOLD
AUG 24, 2026
$429,900
3 bd
2.5 ba
1,728 sqft
528 Sebago Road,
Naples, ME 04055
Landing Real Estate, Closed
SOLD
AUG 19, 2026
$340,000
3 bd
1 ba
1,092 sqft
14 Balsam Lane,
Naples, ME 04055
Maine Real Estate Experts, Closed
SOLD
AUG 18, 2026
$810,000
890 sqft
4 Goodridge Dr,
Naples, ME 04055
SOLD
AUG 18, 2026
$775,000
4 bd
3.5 ba
3,536 sqft
37 Woodland Shore Drive,
Naples, ME 04055
Maine Real Estate Choice, Closed
SOLD
AUG 14, 2026
$322,500
2 bd
1 ba
936 sqft
33 Ridge Terrace Drive,
Casco, ME 04015
Locations Real Estate Group LLC, Closed
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Naples
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Homes for sale near 39 Windsor Green Rd

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0.57 ACRES
$799,999
4 bd
2.5 ba
1,525 sqft
16 Scenic View Drive,
Naples, ME 04055
www.HomeZu.com, Active
0.62 ACRES
$315,000
3 bd
1 ba
1,008 sqft
115 Sand Road,
Naples, ME 04055
Plowman Realty Group, Active
1.54 ACRES
$999,900
3 bd
2 ba
1,988 sqft
67 Fairway Drive,
Naples, ME 04055
Landing Real Estate, Active
0.6 ACRES
$1,045,000
3 bd
1 ba
800 sqft
86 Pine Rock Road,
Naples, ME 04055
The Lakes Real Estate, Active
NEW CONSTRUCTION
1.64 ACRES
$1,350,000
4 bd
3.5 ba
2,863 sqft
47 Fairway Drive,
Naples, ME 04055
Legacy Properties Sotheby's International Realty, Active
0.49 ACRES
$559,000
4 bd
2 ba
1,588 sqft
11 Rabbit Lane,
Naples, ME 04055
Chalmers Realty, Active
NEW CONSTRUCTION
1.38 ACRES
$512,000
3 bd
2 ba
1,400 sqft
24 Mayberry Landing,
Naples, ME 04055
Maine Real Estate Choice, Active
3.49 ACRES
$375,000
3 bd
1.5 ba
1,420 sqft
148 Lake House Road,
Naples, ME 04055
Oberg Insurance & Real Estate Agency, Inc., Active
1.55 ACRES
$398,900
2 bd
1 ba
912 sqft
193 Dunton Road,
Naples, ME 04055
Keller Williams Realty, Active
NEW CONSTRUCTION
0.95 ACRES
$429,500
3 bd
1.5 ba
1,456 sqft
201 Dunton Road,
Naples, ME 04055
EXP Realty, Active
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Naples
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