5 Crossways, Chappaqua, NY 10514
OFF MARKET

5 Crossways
Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 2,212 sqft

$1,347,600

Trulia Estimate
as of Jul 22, 2026
Est. Refi. Payment $8,518/mo*
Refinance Your Home

$1,347,600

Trulia Estimate
as of Jul 22, 2026
Est. Refi. Payment $8,518/mo*
Refinance Your Home
4 Beds
2.5 Baths
2,212 sqft

Local Information

  • Map ViewExplore the area around 5 Crossways.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1934
Living Area
2,212 sqft
Price/Sqft
$609
Parking
Garage

Description

Move right into this walk-to-town beautifully updated 4-bedroom, 2.5-bath Colonial that offers the perfect balance of classic charm and modern convenience. Just steps from the heart of Chappaqua, this home features an open-concept layout and flexible spaces ideal for everyday living and effortless entertaining.
Step through the storybook Dutch door to a light-filled, double-height entry with a skylight and elegant wraparound staircase. The open floorplan offers flexible spaces that can change and evolve with your lifestyle. The sun-drenched updated chef’s kitchen is the centerpiece of the home with generous custom recessed panel cabinetry, large center island seating and stainless steel appliances. It is open to the living and dining areas with custom built ins. Lovely architectural beamed ceilings and a charming fireplace add warmth and character to the living room.
On the first floor, a versatile bedroom (currently used as a den) boasts elegant French doors and an adjacent half bath. With room to add a shower, this space can easily be transformed into a guest suite or convenient first-floor primary.
Upstairs, the generously sized primary suite offers soaring vaulted ceilings, abundant natural light and a newly renovated ensuite bath with double vanity, whirlpool tub and skylight. The second bedroom also features vaulted ceilings and a cozy loft area that is perfect for a reading nook, study space, or creative hideaway. Another bedroom with expansive closets and a newly updated hall bath complete the upper level.
Tucked behind the home, a charming patio with high-end, easy-care turf and lush, vibrant plantings offers a serene spot to enjoy your morning coffee or unwind at the end of the day.
This home has been thoughtfully transformed with numerous recent upgrades including stunning newly refinished floors, fresh interior and exterior paint, lighting, mechanicals and more.
Don’t miss this special Chappaqua gem where charm, convenience, and turnkey living come together in perfect harmony.
5 Crossways, Chappaqua, NY 10514 is a 4 bedroom, 3 bathroom, 2,212 sqft single-family home built in 1934. It last sold for $1,280,000 on Sep 3, 2025 (16% above the $1,099,000 asking price). It is currently off market. The Trulia Estimate is $1,347,600, with a rent estimate of $5,954/month.

Home Details for 5 Crossways

Interior Features

Interior Details
Basement: Full,Storage SpaceNumber of Rooms: 10
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2212 Square Feet
Appliances & Utilities
Utilities: Natural Gas AvailableAppliances: Dishwasher, Dryer, Electric Cooktop, Freezer, Microwave, Oven, Refrigerator, Stainless Steel Appliance(s), WasherDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Hot Water,Oil,See RemarksHas CoolingAir Conditioning: DuctlessHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Living Room, Wood BurningHas a FireplaceNo Spa
Windows, Doors, Floors & Walls
Flooring: Hardwood
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Exterior Home Features
No Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageParking Spaces: 1Parking: Garage
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 12

Property Information

Year Built
Year Built: 1934
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Colonial
Building
Construction Materials: Wood SidingNot Attached Property
Property Information
Included in Sale: Grill, Back patio table and chairsParcel Number: 3600092020000020000016

Price & Status

Price
List Price: $1,099,000
Status Change & Dates
Off Market Date: Tue May 13 2025

Active Status

MLS Status: Sold

Location

Direction & Address
City: Chappaqua
School Information
Elementary School: Douglas G Grafflin SchoolJr High / Middle School: Robert E Bell SchoolHigh School: Horace Greeley High SchoolHigh School District: Chappaqua

Building

Building Area
Building Area: 2212 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 9148 sqft

Listing Info

Special Conditions: None

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: 844639Attic: CrawlAttribution Contact: 914-238-0676Showing Requirements: Appointment Only, Lockbox
Last check for updates: about 18 hours ago
Listed by Jill Urban, (646) 245-8048
Compass Greater NY, LLC, (914) 238-0676
Bought with: Amy M. Singer, (914) 772-3526, Houlihan Lawrence Inc., (914) 273-9505
Source: OneKey® MLS as distributed by MLS GRID, MLS#844639

Price History for 5 Crossways

DatePriceEventSource
09/03/2025$1,280,000Sold
OneKey® MLS as distributed by MLS GRID #844639
05/17/2025$1,099,000PendingOneKey® MLS as distributed by MLS GRID #844639
05/13/2025$1,099,000ListingRemovedOneKey® MLS as distributed by MLS GRID #844639
05/01/2025$1,099,000Listed For SaleOneKey® MLS as distributed by MLS GRID #844639

Market trends in Chappaqua

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
32
5MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$144,000
Home facts updated by county records

Comparable Sales for 5 Crossways

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
45 Crossways, Chappaqua, NY
0.08
Single-Family Home
$1,560,000
08/07/25
3
2.5
2,246
59 Crest Road, Chappaqua, NY
0.17
Single-Family Home
$1,646,500
10/21/25
4
2.5
2,550
26 Kings Court, Chappaqua, NY
0.51
Single-Family Home
$1,298,000
12/18/25
4
2.5
2,060
33 High Way, Chappaqua, NY
0.19
Single-Family Home
$1,465,000
10/01/25
3
3.5
1,917
21 Kitchawan Drive, Chappaqua, NY
0.31
Single-Family Home
$1,850,000
06/01/26
4
2.5
3,956
100 Castle Road, Chappaqua, NY
0.19
Single-Family Home
$1,025,000
08/22/25
3
3.5
2,590
71 Commodore Road, Chappaqua, NY
0.52
Single-Family Home
$1,290,000
01/21/26
3
2
1,957
58 Spring Lane, Chappaqua, NY
0.46
Single-Family Home
$1,815,000
11/10/25
4
2.5
3,457

Nearby homes

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Assigned Schools

These are the assigned schools for 5 Crossways.
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 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.
  • Trulia User
    "It’s a dog friendly place."
    0
    Flag
  • Chaarey
    "Easily accessible to all major roadways. I moved from one town over and absolutely love everything about it here. Shopping is amazing, food choices are plentiful, it’s clean but most of all, the people are amazing! "
    0
    Flag
  • Mereslavin
    "The commute is not too long and metro north is nice. Commuting into grand central is much nicer than commuting into penn."
    0
    Flag
  • Mereslavin
    "There’s Lots of space to play in and it’s very quiet. There’s lot of other animals which dogs might not like"
    1
    Flag
  • Marta V.
    "Very upscale. Safe. Family oriented. Clean. Good school district. Good for outdoors. Train to Manhattan makes it an easy and convenient commute. "
    0
    Flag
  • Jill B.
    "It’s great place to live, safe and friendly great neighborhood, easy commute to NYC. Lived here for 25 years, we have looked to downsize but can’t find a better place to live. "
    2
    Flag
  • Jill B.
    "Lived here for 18 years and love it, safe and friendly love my neighbors , perfect for country living and easy access to NYC great schools and community activities "
    0
    Flag
  • Trulia User
    "Feels safe and neighborhood friendly a golf course and great restaurant very pretty landescapes and trees beautiful houses "
    0
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  • Lizrappaport
    "It is very wooded with homes that are far apart from each other. There is no seeing into the neighbor’s kitchen, for example. The schools are excellent and the people are generally laid back. They are discerning and demanding, but not snobbish. "
    2
    Flag
  • Diane N. W.
    "My community has access to MetroNorth Station, buses, parks, bicycle paths, elite school system, restaurants, country setting...."
    0
    Flag
  • Elymiani
    "Amicable woodland safe all you need is her . Friendly. The best school are in chappaqua district . "
    1
    Flag
  • Carlosgamboan
    "I just moved in and already love the neighborhood. Great Schools, peaceful, lots of trees, friendly neighbors"
    1
    Flag
  • Christine R.
    "I grew up in Chappaqua, and lived there with my own children for several years. The Chappaqua schools are very highly rated, and the Park & Recreation department is very active as well. There is a small town feeling, but easily accessibility to NYC and White Plains via Metro North."
    0
    Flag
  • bal
    "i am so impressed with this litttle jewel of place in Chappaqua "
    0
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  • Susan S.
    "Incredible Old Farm Lake. Families, Singles and Couples all welcome. Convenient to the greatest schools, shopping and restaurants."
    0
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Homes for sale near 5 Crossways

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Off Market Homes Near 5 Crossways

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Based on information submitted to the MLS GRID as of 2026-07-21 12:43:08 PDT All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. Click here for more information