39 Upland Dr
Chappaqua, NY 10514
4 Beds
3.5 Baths
5,867 sqft (on 1.07 acres)
4 Beds
3.5 Baths
5,867 sqft
(on 1.07 acres)
Local Information
- Map ViewExplore the area around 39 Upland Dr.
- Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1938
Lot Size
1.07 acres
Living Area
5,867 sqft
Price/Sqft
$530
Parking
Garage
About this House
This 5867 square foot single family home has 4 bedrooms and 3.5 bathrooms. Complete home renovation with 2500 sq foot addition in 2008. It is located at 39 Upland Dr Chappaqua, New York. This home is in the Chappaqua Central School District. The nearest schools are Douglas G. Grafflin School, Robert E. Bell Middle School and Horace Greeley High School.
39 Upland Dr, Chappaqua, NY 10514 is a 4 bedroom, 4 bathroom, 5,867 sqft single-family home built in 1938. It last sold for $2,000,000 on Jul 7, 2016. It is currently off market. The Trulia Estimate is $3,110,700, with a rent estimate of $8,096/month.
Home Details for 39 Upland Dr
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Interior Details BasementAtticNumber of Rooms: 12Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Office, Pantry, Recreation RoomCeiling Fan |
Heating & Cooling Heating: Forced Air, Radiant, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 2Floors: Hardwood |
Appliances & Utilities Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher |
Fireplace & Spa Fireplace |
Windows, Doors, Floors & Walls Double Paned Windows |
Security Security System |
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Exterior Home Features Roof: AsphaltExterior: WoodGardenLawnPatioPorch |
Pool Pool |
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached |
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Year Built Year Built: 1938Year Updated: 2008 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Units in Building: 1 |
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Lot Area: 1.07 acres |
Price History for 39 Upland Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 07/07/2016 | $2,000,000 | Sold | OneKey® MLS as distributed by MLS GRID #H4612039 |
| 04/21/2016 | $2,000,000 | Pending | Agent Provided |
| 03/31/2016 | $2,000,000 | Listed For Sale | Agent Provided |
| 12/01/2005 | $1,430,000 | Sold | N/A |
Market trends in Chappaqua
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
32
5MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | |
| Assessment | $350,000 |
Home facts updated by county records
Comparable Sales for 39 Upland Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.10 | Single-Family Home | $2,000,000 | 10/29/25 | 6 | 5 | 5,234 | |
0.15 | Single-Family Home | $2,700,000 | 11/04/25 | 4 | 6.5 | 5,354 | |
0.20 | Single-Family Home | $1,609,031 | 06/29/26 | 4 | 2.5 | 2,443 | |
0.42 | Single-Family Home | $1,850,000 | 06/01/26 | 4 | 2.5 | 3,956 | |
0.45 | Single-Family Home | $2,375,000 | 06/12/26 | 3 | 3.5 | 3,960 | |
0.45 | Single-Family Home | $2,300,000 | 12/03/25 | 3 | 3.5 | 3,638 | |
0.15 | Single-Family Home | $450,000 | 08/28/25 | 4 | 3 | 2,949 | |
0.51 | Single-Family Home | $1,391,022 | 10/23/25 | 4 | 3.5 | 3,776 | |
0.19 | Single-Family Home | $3,975,000 | 06/10/26 | 5 | 6 | 6,935 | |
0.54 | Single-Family Home | $1,720,000 | 02/04/26 | 4 | 3.5 | 3,244 |
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Assigned Schools
These are the assigned schools for 39 Upland Dr.
- Douglas G Grafflin School
- PK-4
- Public
- 415 Students
10/10GreatSchools RatingParent Rating AverageI have 3 children at Grafflin and they have had wonderful experiences there. The school has great leadership with the principal and assistant principal; a caring and attentive support staff of custodians, admins, and security; and an outstanding group of teachers. The school and parents support many extracurricular programs to expose the children to different topics, through assemblies, after-school enrichment, and special family activities. In the classroom, the children (my children at least) have enough work to be challenged without being overwhelmed. Homework is consistent and manageable. Overall, we've had a great experience at the school.Parent Review10y ago - Horace Greeley High School
- 9-12
- Public
- 1122 Students
10/10GreatSchools RatingParent Rating AverageExcellent! There were lots of wholesome activities, and there was Canteen on Friday nights where we could dance and be with friends. I was well prepared for college when I graduated.Other Review6y ago - Robert E Bell School
- 5-8
- Public
- 587 Students
9/10GreatSchools RatingParent Rating AverageThe good:Smart, straight A students do well and get some opportunity for advanced classes in 8th grade.Most teachers are amazing and kind.The counselors are supportive. The bad:Most other students struggle.Stressful environment.Unreasonable homework load, that consists mostly of busy work.Overworked children and teachers.Neurodivergent kids are not supported even with accommodations (see above - overworked teachers. There’s only so much they can do.). Brilliant ND kids are constantly being pushed out to private schools, if the parents are able to afford.District schools tend to dismiss mid-day for disagreeable various reasons, like rain. With too short of a notice to parents. (Happened twice this school year alone.)Also worth mentioning that cost of housing and taxes for the district are very high.Parent Review2y ago 
Check out schools near 39 Upland Dr.
What Locals Say about Chappaqua
At least 64 Trulia users voted on each feature.
91 % Say it's quiet
90 % Say car is needed
86 % Say parking is easy
85 % Say it's dog friendly
78 % Say yards are well-kept
75 % Say people would walk alone at night
73 % Say there's wildlife
72 % Say there's holiday spirit
62 % Say neighbors are friendly
61 % Say they plan to stay for at least 5 years
54 % Say kids play outside
50 % Say it's walkable to restaurants
37 % Say there are community events
35 % Say there are sidewalks
32 % Say streets are well-lit
26 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
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