20 Captains Way
Ossipee, NH 03864
2 Beds
2 Baths
2,416 sqft (on 1.04 acres)
$413,600
as of Jul 22, 2026
$413,600
as of Jul 22, 2026
2 Beds
2 Baths
2,416 sqft
(on 1.04 acres)
Local Information
- Map ViewExplore the area around 20 Captains Way.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1977
Lot Size
1.04 acres
Living Area
2,416 sqft
Price/Sqft
$171
Parking
Garage
Description
At this price how can you go wrong!?! Huge hangar with high door, with garage space, work shop, studio over and right on the runway. Home is set up for 2 living spaces! 2 Living rooms, 2 kitchens 2 baths even 2 separate screen porches overlooking runway NH69. Use as is or redesign to fit you needs. Level lot. Home set back from road with lots of tall pines. Located in Windsock Village in West Ossipee, NH. 30 minutes to North Conway for shopping, restaurants and other attractions. Fly or drive to this year round home.
20 Captains Way, Ossipee, NH 03864 is a 2 bedroom, 2 bathroom, 2,416 sqft single-family home built in 1977. It is currently off market. The Trulia Estimate is $413,600, with a rent estimate of $2,451/month.
Home Details for 20 Captains Way
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Heating & Cooling Heating: Forced Air, Electric, OilHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 2Floors: Carpet, Linoleum Vinyl |
Interior Details Number of Rooms: 9Types of Rooms: Dining RoomCeiling Fan |
Appliances & Utilities Cable ReadyDryerRefrigeratorWasher |
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Exterior Home Features Roof: MetalDeckExterior: WoodPorch |
Parking & Garage GarageParking: Garage Detached |
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Year Built Year Built: 1977 |
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional |
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Levels, Entrance, & Accessibility Disabled Access |
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Lot Area: 1.04 acres |
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On Site Laundry Available |
Price History for 20 Captains Way
| Date | Price | Event | Source |
|---|---|---|---|
| 07/01/2015 | $158,000 | ListingRemoved | Agent Provided |
| 06/29/2015 | $158,000 | PriceChange | Agent Provided |
| 03/30/2015 | $200,000 | PriceChange | Agent Provided |
| 11/02/2014 | $235,000 | PriceChange | Agent Provided |
| 10/28/2014 | $249,900 | PriceChange | Agent Provided |
| 09/30/2014 | $235,000 | PriceChange | Agent Provided |
| 06/20/2014 | $249,900 | Listed For Sale | Agent Provided |
Market trends in Ossipee
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
36
9MoM
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Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $4,569 |
| Assessment | $393,900 |
Home facts updated by county records
Comparable Sales for 20 Captains Way
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.40 | Single-Family Home | $489,000 | 12/15/25 | 4 | 2.5 | 2,421 | |
0.86 | Single-Family Home | $400,000 | 11/10/25 | 3 | 2 | 1,686 | |
1.32 | Single-Family Home | $586,000 | 09/22/25 | 3 | 2 | 1,859 | |
1.26 | Single-Family Home | $382,500 | 01/16/26 | 3 | 3 | 1,200 | |
1.31 | Single-Family Home | $485,000 | 06/11/26 | 3 | 2 | 1,638 | |
1.12 | Single-Family Home | $290,000 | 05/04/26 | 2 | 1 | 1,453 | |
1.25 | Single-Family Home | $276,800 | 08/28/25 | 4 | 2 | 3,098 | |
1.29 | Single-Family Home | $349,900 | 03/31/26 | 3 | 1 | 936 | |
1.55 | Single-Family Home | $528,000 | 09/05/25 | 3 | 2.5 | 2,250 | |
1.29 | Single-Family Home | $165,000 | 12/05/25 | 4 | 2 | 2,224 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
Assigned Schools
These are the assigned schools for 20 Captains Way.
- Kingswood Regional High School
- 9-12
- Public
- 729 Students
7/10GreatSchools RatingParent Rating AveragePoor administration at the top end. The teachers are great, but the upper administration is horrible. They let the students run the place with limited discipline. If you want your kid to be bullied, picked on, and feel worthless, this is the school for you! Do yourself a favor and stay clear!Parent Review1y ago - Ossipee Central School
- PK-6
- Public
- 276 Students
5/10GreatSchools RatingParent Rating AverageOssipee Central has a dedicated staff with a strong reading program that has paid off as our children continued their upper education. The building is kept impeccably and is always a welcoming space to walk into with the students, art and scholastic work prominent ally displayed.Parent Review10y ago - Kingswood Regional Middle School
- 7-8
- Public
- 345 Students
6/10GreatSchools RatingParent Rating AverageThis school isn't a safe place to learn, I am a student in 8th grade. I was walking up to my class minding my own business when a punk came up to me and "flat tired" me. he ended up taking off my shoe. I turned around and looked at who did it. another student who I've known for many years came to me and squared up, said "Want to f-ing go?" he put his fists up and came twords me, in self defense I put my hands up. The student then tried to punch me so I defended myself. I ended up getting punched multiple times in the head / face, almost getting pushed out of a window. I only swung once to defend myself.I am not a human punching bag, and I will not stay quiet about this. this school is not safe. and the staff need more training in how to prevent things that have happened for the last 5+ years. All 3 of the students (that includes me) where suspended for 3 days.Student Review4y ago 
Check out schools near 20 Captains Way.
What Locals Say about Ossipee
At least 14 Trulia users voted on each feature.
93 % Say parking is easy
87 % Say yards are well-kept
87 % Say there's wildlife
78 % Say car is needed
69 % Say there's holiday spirit
69 % Say it's quiet
63 % Say it's dog friendly
63 % Say people would walk alone at night
60 % Say neighbors are friendly
50 % Say they plan to stay for at least 5 years
43 % Say kids play outside
43 % Say there are community events
10 % Say it's walkable to restaurants
Sourced by Trulia users. Learn more about our methodology.
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