45 Crossways, Chappaqua, NY 10514
OFF MARKET

$1,693,400

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 2,246 sqft (on 0.25 acres)

45 Crossways, Chappaqua, NY 10514

Est. Refi. Payment $10,907/mo*
Refinance Your Home
Currently Off Market - Sold Aug 7, 2025 for $1,560,000

Home Value

Trulia Estimate
$1.69M
Since last month
Increased$27K (+1.6%)
Since last year
Increased$126K (+8%)
Since last sale
Increased$132K (+8.4%)
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 +140% in the last 10 years
MonthEstimated value
2026
August 2026$1.69M
August 2026$1.69M
July 2026$1.66M
June 2026$1.64M
May 2026$1.62M
April 2026$1.63M
March 2026$1.63M
February 2026$1.58M
January 2026$1.6M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
59 Crest Road, Chappaqua, NY
0.26
Single-Family Home
$1,646,500
10/21/25
4
2.5
2,550
14 Crossways, Chappaqua, NY
0.08
Single-Family Home
$1,731,000
08/06/26
4
3.5
3,138
33 High Way, Chappaqua, NY
0.12
Single-Family Home
$1,465,000
10/01/25
3
3.5
1,917
40 Kings Court, Chappaqua, NY
0.53
Single-Family Home
$2,025,000
07/22/26
3
2.5
3,121
26 Kings Court, Chappaqua, NY
0.59
Single-Family Home
$1,298,000
12/18/25
4
2.5
2,060
80 Bischoff Avenue, Chappaqua, NY
0.39
Single-Family Home
$715,000
09/01/26
3
2.5
1,299
21 Kitchawan Drive, Chappaqua, NY
0.33
Single-Family Home
$1,850,000
06/01/26
4
2.5
3,956
71 Commodore Road, Chappaqua, NY
0.48
Single-Family Home
$1,290,000
01/21/26
3
2
1,957

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
30 Lori Lane, Chappaqua, NY 10514
0.06
$1,340,300
4
3
2,288
Off Market
29 Crossways, Chappaqua, NY 10514
0.04
$1,671,000
3
2.5
2,946
Off Market
33 High Way, Chappaqua, NY 10514
0.12
$1,571,900
3
3.5
1,917
Off Market
5 Crossways, Chappaqua, NY 10514
0.08
$1,380,600
4
2.5
2,212
Off Market
14 Crossways, Chappaqua, NY 10514
0.08
$1,731,000
4
3.5
3,138
Recently Sold
339 N Greeley Avenue #339, Chappaqua, NY 10514
0.16
$678,400
2
2
1,563
Off Market
301 N Greeley Avenue, Chappaqua, NY 10514
0.16
$550,000
1
1.5
1,226
Off Market
324 N Greeley Avenue, Chappaqua, NY 10514
0.16
$651,700
2
2
1,608
Off Market
325 N Greeley Avenue, Chappaqua, NY 10514
0.16
$491,700
1
1.5
1,226
Off Market
356 North Greeley Avenue, Chappaqua, NY 10514
0.16
$460,000
1
1.5
1,207
Recently Sold
368 N Greeley Avenue, Chappaqua, NY 10514
0.16
$510,000
1
1.5
1,207
Recently Sold

Local Information

  • Map ViewExplore the area around 45 Crossways.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1935
0.25 acre lot
2,246 sqft
$754/sqft
Garage

About this House

Storybook 1930’s-era Tudor-style shingle cottage delightfully renovated & updated with all the comforts for the 21st century. Believed to be originally derived from Standard Homes Co. classic Densmore model. A welcoming entry vestibule with French door introduces a wide, front-facing living room, warmed by a stout wood-burning fireplace. Gather together in the dining room to enjoy holiday feasts artfully prepared in the modern, gourmet chef's kitchen outfitted with upscale appliances, functionally beautiful cabinetry, all sweetly accented by a backsplash of small glass subway tile. Relax, play or entertain in the large & inviting family room which adjoins the kitchen and enjoys light exposures on three sides including floor-to-ceiling windows & French doors which bring the outside in. An expansive bluestone terrace lays just beyond. The sun parlor is an ideal spot for more solitary pursuits, like reading, painting, practicing a musical instrument, or working from home. A small powder room completes the main level. A proud, L-shaped staircase ascends to the upper-level, home to a front-corner bedroom; a side-facing bedroom; an updated hall bath with glass-walled shower with bench, radiant heat & heated towel rack; an enchanting primary suite, endowed with a high ceiling, dramatic rear-facing windows, and luxurious ensuite bath with radiant heat & heated towel rack; and a front-facing den/study, which could also serve as a home office, and has a staircase ascending to the full attic. Downstairs houses an unfinished basement with laundry, natural gas utilities, storage, and access to the 1-car attached garage. With central air conditioning, municipal water and sewer. The outside grounds are very attractive. A bluestone terrace spreads out from the family room. Five wide steps lead from the terrace up to a lush lawn blanketing the back yard. Lovely, well-tended landscaping surrounds the property. A true village charmer just a short stroll to shops, schools, town & train.
45 Crossways, Chappaqua, NY 10514 is a 3 bedroom, 3 bathroom, 2,246 sqft single-family home built in 1935. It last sold for $1,560,000 on Aug 7, 2025 (30% above the $1,200,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,693,400, with a rent estimate of $6,457/month.
Last check for updates: about 17 hours ago
Listed by Stacy Levey, (914) 400-3962
William Raveis-New York, LLC, (914) 238-0505
Bought with: Jia Wei, (917) 601-2697, Keller Williams Realty Group, (914) 713-3270
Source: OneKey® MLS as distributed by MLS GRID, MLS#H6330095

Home Details for 45 Crossways

Interior Features

Interior Details
Basement: UnfinishedNumber of Rooms: 8
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2246 Square Feet
Appliances & Utilities
Utilities: Trash Collection PublicAppliances: Convection Oven, Dishwasher, Dryer, Gas Cooktop, Microwave, Oven, Refrigerator, Stainless Steel Appliance(s), Washer, Indirect Water HeaterDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,SteamHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Window: Drapes, BlindsFlooring: Hardwood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Hardwood

Exterior Features

Exterior Home Features
Patio / Porch: Patio
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageHas Open ParkingParking Spaces: 1Parking: Attached,Driveway
Frontage
Responsible for Road Maintenance: Public Maintained Road
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 4

Property Information

Year Built
Year Built: 1935Year Renovated: 2013
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Chalet,Colonial,Cottage,Tudor
Building
Construction Materials: Shake Siding, CedarNot Attached Property
Property Information
Not Included in Sale: Dining Room Draperies, Primary Bedroom Chandelier & DraperiesIncluded in Sale: Light Fixtures, Second RefrigeratorParcel Number: 3600092020000020000009

Price & Status

Price
List Price: $1,200,000
Status Change & Dates
Off Market Date: Mon Mar 03 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: 2246 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 10890 sqft

Listing Info

Special Conditions: None

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: H6330095Attic: Full, WalkupAttribution Contact: 914-238-0505Showing AttendedShowing Requirements: Appointment Only, No Lockbox, No Sign, Occupied

Price and Tax history

DateEventPrice
Aug 7, 2025
Source: OneKey® MLS as distributed by MLS GRID #H6330095
Sold
$1,560,000
Mar 10, 2025
Source: OneKey® MLS as distributed by MLS GRID #H6330095
Pending
$1,200,000
Mar 4, 2025
Source: William Raveis Real Estate, Mortgage & Insurance #H6330095
ListingRemoved
$1,200,000
Feb 27, 2025
Source: OneKey® MLS as distributed by MLS GRID #H6330095
Listed For Sale
$1,200,000
Jan 7, 2004
Source: N/A
Sold
$620,000

Market trends in Chappaqua

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
27
5MoM

Around this home

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
    "Plenty of areas that can walk dogs , quiet and safe"
    0
    Flag
  • Alvin Robert Colby
    "The community is relatively safe."
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • Susan S.
    "Incredible Old Farm Lake. Families, Singles and Couples all welcome. Convenient to the greatest schools, shopping and restaurants."
    0
    Flag

LGBTQ Local Legal Protections

Based on information submitted to the MLS GRID as of 2026-09-09 09:48:16 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

Frequently asked questions about 45 Crossways

  • What is 45 Crossways estimated to be worth?
    Trulia's estimated value for 45 Crossways in Chappaqua, NY is $1,693,400.
  • What is the price history for 45 Crossways?
    45 Crossways in Chappaqua, NY last sold for $1,560,000 in August 2025.
  • Is Chappaqua a buyer's or seller's market?
    Chappaqua is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Chappaqua?
    Residents describe Chappaqua, NY as quiet, easy to park in, and dog-friendly. Most residents say you need a car. See recently sold homes in Chappaqua, NY.
  • Does 45 Crossways have air conditioning?
    Yes, 45 Crossways in Chappaqua, NY has air conditioning.
  • Does 45 Crossways have laundry facilities?
    Yes, 45 Crossways in Chappaqua, NY has in-unit laundry.

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