29 Crossways, Chappaqua, NY 10514
OFF MARKET

29 Crossways
Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 2,946 sqft

$1,580,300

Trulia Estimate
as of Jul 23, 2026
Est. Refi. Payment $9,993/mo*
Refinance Your Home

$1,580,300

Trulia Estimate
as of Jul 23, 2026
Est. Refi. Payment $9,993/mo*
Refinance Your Home
3 Beds
2.5 Baths
2,946 sqft

Local Information

  • Map ViewExplore the area around 29 Crossways.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1921
Living Area
2,946 sqft
Price/Sqft
$536
Parking
Garage

Description

Welcome home to a 1920s Sears Roebuck English cottage style home that was impeccably renovated and expanded while honoring the original aesthetic. This walk to shopping, dining, train & school three bedroom home that can live like a four bedroom blends timeless elegance with an open, livable floor plan suited for today’s lifestyle. From the moment you enter the home through the arch doorway, you are greeted by a foyer leading to a living room with a wood burning fireplace and French doors to an office/study with an en suite powder room. On the other side of the living room you will find a large formal dining room. The highlight of the main level is a stunning coffered ceiling chef’s kitchen with center island seating, custom recessed paneled cabinetry, high end stainless steel appliances, radiant flooring and a sensational windowed breakfast room overlooking the rear bluestone patio and yard. The kitchen seamlessly flows into a large family room that is ideal for entertaining. The second level’s living space has hardwood flooring throughout & boasts a primary bedroom with a cathedral ceiling, large walk in closet and en suite bath with marble vanity and marble & radiant flooring. There are two additional generously sized bedrooms- one with an oversized bay window & built in cabinetry, and a renovated skylit bathroom with vintage reproduction tile flooring. The approximately 600 sq foot finished lower level (included in total) is sure to impress with its 9 foot ceilings. The rear yard is a private oasis with a 225 sq foot bluestone patio and a very flat area for play. Low taxes, natural gas, town sewer & central air. This home with storybook features blends suburban tranquility on a quiet tree-lined street with the convenience of being just steps from everything Chappaqua has to offer! Additional Information: Amenities:Marble Bath,ParkingFeatures:1 Car Attached,
29 Crossways, Chappaqua, NY 10514 is a 3 bedroom, 3 bathroom, 2,946 sqft single-family home built in 1921. It last sold for $1,425,000 on Jan 7, 2025 (19% above the $1,200,000 asking price). It is currently off market. The Trulia Estimate is $1,580,300, with a rent estimate of $6,593/month.

Home Details for 29 Crossways

Interior Features

Interior Details
Basement: Finished,FullNumber of Rooms: 9
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2946 Square Feet
Appliances & Utilities
Utilities: Trash Collection PublicAppliances: Stainless Steel Appliance(s), Gas Water Heater, Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, WasherDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,RadiantHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Window: Drapes, Screens, Blinds
Levels, Entrance, & Accessibility
Stories: 3Levels: Three Or More

Exterior Features

Exterior Home Features
Patio / Porch: PatioExterior: Basketball Hoop
Parking & Garage
No CarportGarageParking Spaces: 1Parking: Attached,Garage Door Opener
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 67

Property Information

Year Built
Year Built: 1921
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Tudor
Building
Construction Materials: Cedar, Shingle SidingNot Attached Property
Property Information
Included in Sale: Light Fixtures, Oven/Range, Playset, Second RefrigeratorParcel Number: 3600092020000020000020

Price & Status

Price
List Price: $1,200,000
Status Change & Dates
Off Market Date: Fri Nov 08 2024

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: 2946 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 10454 sqft

Offer

Listing Agreement Type: Exclusive Right To SellListing Terms: Cash

Miscellaneous

BasementMls Number: H6331259Attic: PartialAttribution Contact: 914-238-0505Showing AttendedShowing Requirements: Lockbox
Last check for updates: about 10 hours ago
Listed by Amanda M. Goldberg, (917) 359-6845
William Raveis-New York, LLC, (914) 238-0505
Bought with: Jill Urban, (646) 245-8048, William Raveis-New York, LLC, (914) 238-0505
Source: OneKey® MLS as distributed by MLS GRID, MLS#H6331259

Price History for 29 Crossways

DatePriceEventSource
01/07/2025$1,425,000Sold
OneKey® MLS as distributed by MLS GRID #H6331259
11/08/2024$1,200,000PendingOneKey® MLS as distributed by MLS GRID #H6331259
11/01/2024$1,200,000Listed For SaleOneKey® MLS as distributed by MLS GRID #H6331259
06/12/2015$860,000Sold
OneKey® MLS as distributed by MLS GRID #H4506788
02/25/2015$885,000Listed For SaleAgent Provided

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$128,500
Home facts updated by county records

Comparable Sales for 29 Crossways

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
45 Crossways, Chappaqua, NY
0.04
Single-Family Home
$1,560,000
08/07/25
3
2.5
2,246
5 Crossways, Chappaqua, NY
0.05
Single-Family Home
$1,280,000
09/03/25
4
2.5
2,212
59 Crest Road, Chappaqua, NY
0.22
Single-Family Home
$1,646,500
10/21/25
4
2.5
2,550
40 Kings Court, Chappaqua, NY
0.50
Single-Family Home
$2,025,000
07/22/26
3
2.5
3,121
33 High Way, Chappaqua, NY
0.15
Single-Family Home
$1,465,000
10/01/25
3
3.5
1,917
26 Kings Court, Chappaqua, NY
0.56
Single-Family Home
$1,298,000
12/18/25
4
2.5
2,060
21 Kitchawan Drive, Chappaqua, NY
0.32
Single-Family Home
$1,850,000
06/01/26
4
2.5
3,956
100 Castle Road, Chappaqua, NY
0.21
Single-Family Home
$1,025,000
08/22/25
3
3.5
2,590
71 Commodore Road, Chappaqua, NY
0.49
Single-Family Home
$1,290,000
01/21/26
3
2
1,957

Nearby homes

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Assigned Schools

These are the assigned schools for 29 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
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  • 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
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  • 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
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  • 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 29 Crossways

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Off Market Homes Near 29 Crossways

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Based on information submitted to the MLS GRID as of 2026-07-22 16:13:18 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