99 E Main Street, Pawling, NY 12564
OFF MARKET

99 E Main Street
Pawling, NY 12564

  • 4 Beds
  • 2.5 Baths
  • 4,013 sqft (on 0.84 acres)

$773,900

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $5,124/mo*
Refinance Your Home

$773,900

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $5,124/mo*
Refinance Your Home
4 Beds
2.5 Baths
4,013 sqft
(on 0.84 acres)

Local Information

  • Map ViewExplore the area around 99 E Main Street.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Introducing to the market for the first time in over twenty years, one of the Village of Pawling's most iconic homes. If you've been to Pawling, you've probably admired this home on your way into the Village. On East Main Street on a double lot sits this 4,000+ square foot mid-century modern home. The meticulous landscaping and sprawling design of the home catch the eye of all who pass. The functional elegance of the mid-century modern movement is evident everywhere in the home, from the huge rooms with wide openings, to the built-in wood cabinetry, to the clean lines of the Cox metal kitchen cabinetry. Because of the simple timeless design and loving attention to all its details from the homeowners, this home has managed to retain its original character and needs no repairs or decorating. You can move in right away and start enjoying life in the Village. Follow the bluestone walkway to the elegant front entrance flanked by local stone, and step into the foyer. The stone fireplace then welcomes you into the 16' x 26' living room. From the living room one can see through the wide openings into the dining room and family room. The family room, at the south end of the home, features a wall of built-in cabinetry and a wet bar. It's open to the formal dining room and has a wide sliding glass door out to the bluestone floored sunroom and backyard. At the rear center is the kitchen. Cork flooring is complemented by quartz countertops over and under white Cox metal cabinets with original space saver features. You'd be hard pressed to find a home with more functional cabinet space. In the kitchen is an ample breakfast area, bright with sunlit bay windows. At the rear north-west side of the home is the primary bedroom that shares a full bath with the second bedroom at the front of the home. The bath features an updated tiled stall shower, soaking tub, and glass tiled walls. The laundry/mud room, next to the kitchen, has an entrance from the backyard. From the foyer a staircase leads up one flight to an office/den with a cedar closet, a hall bath with a tub, and the third and fourth dormered front to back bedrooms, both with access to enormous attic space at each end of the home. The two-car attached garage has hot and cold water, is heated with its own zone, and it enters the home from the front covered porch. The backyard is enclosed with a white fence that has a deck built into the perimeter. The amazing front yard is perfectly level and landscaped with blooming fruit trees, shrubs, and flowers. This home is pedestrian friendly. The village center is only a 5-minute walk away, with Metro North to NYC, shopping, restaurants, and a host of outdoor activities, all nearby. Perfect for full time living or a weekend escape. Additional Information: Amenities:Stall Shower,Storage,HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Attached,
99 E Main Street, Pawling, NY 12564 is a 4 bedroom, 3 bathroom, 4,013 sqft single-family home built in 1955. It last sold for the $700,000 asking price on Jun 22, 2023. It is currently off market. The Trulia Estimate is $773,900, with a rent estimate of $5,853/month.

Home Highlights

Parking
Open Parking
Outdoor
Porch, Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 99 E Main Street

Interior Features

Interior Details
Basement: Bilco Door(s),Partially FinishedNumber 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: 4013 Square Feet
Appliances & Utilities
Utilities: Trash Collection PublicAppliances: Dishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Stainless Steel Appliance(s), WasherDishwasherDryerLaundry: InsideMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,OilHas CoolingAir Conditioning: Wall/Window Unit(s)Has HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Window: Oversized Windows, Wall of WindowsFlooring: Hardwood
Levels, Entrance, & Accessibility
Stories: 3Levels: Three Or MoreFloors: Hardwood

Exterior Features

Exterior Home Features
Patio / Porch: Patio, PorchFencing: FencedVegetation: Partially Wooded
Parking & Garage
No CarportHas Open ParkingParking Spaces: 2Parking: Attached,Driveway
Frontage
Responsible for Road Maintenance: Public Maintained Road
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 1955
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Contemporary,Mid-Century Modern,Ranch
Building
Construction Materials: Stone, Wood SidingNot Attached Property
Property Information
Not Included in Sale: Whole House Ent. SystIncluded in Sale: Oven/RangeParcel Number: 1340017056051588490000

Price & Status

Price
List Price: $700,000
Status Change & Dates
Off Market Date: Tue May 16 2023

Active Status

MLS Status: Sold

Location

Direction & Address
City: Pawling
School Information
Elementary School: Pawling Elementary SchoolJr High / Middle School: Pawling Middle SchoolHigh School: Pawling High SchoolHigh School District: Pawling

Building

Building Area
Building Area: 4013 Square Feet

Community

Community Features: ParkNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.84 acres

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: H6239304Attic: PartialAttribution Contact: (914) 447-3761Showing Advance Notice: 2Showing Requirements: Combination Lock Box, Showing Service

Additional Information

HOA Amenities: Park
Last check for updates: about 9 hours ago
Listed by Claudia Jiskra, (914) 447-3761
McGrath Realty Inc, (845) 855-5550
Bought with: Margaret MacLeay, (845) 656-8595, BHHS Hudson Valley Properties, (845) 855-8500
Source: OneKey® MLS as distributed by MLS GRID, MLS#H6239304

Price History for 99 E Main Street

DatePriceEventSource
06/22/2023$700,000Sold
OneKey® MLS as distributed by MLS GRID #H6239304
05/16/2023$700,000PendingOneKey® MLS as distributed by MLS GRID #H6239304
04/01/2023$700,000Listed For SaleOneKey® MLS as distributed by MLS GRID #H6239304
06/22/2002$399,000Sold
N/A
05/01/2000$295,000Sold
N/A

Market trends in Pawling

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
24
3MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$478,200
Home facts updated by county records

Comparable Sales for 99 E Main Street

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
66 Fairway Drive, Pawling, NY
0.17
Single-Family Home
$535,000
03/10/26
3
2
1,490
48 W Main Street, Pawling, NY
0.55
Single-Family Home
$742,000
01/20/26
5
3.5
3,766
68 W Main Street, Pawling, NY
0.63
Single-Family Home
$700,000
10/06/25
7
3
3,400
40 Walnut Street, Pawling, NY
0.70
Single-Family Home
$439,370
05/20/26
4
1.5
1,776
79 W Main Street, Pawling, NY
0.72
Single-Family Home
$615,000
04/02/26
3
2
2,254
26 Frenchmans Lane, Pawling, NY
0.80
Single-Family Home
$575,000
11/24/25
3
1.5
1,518
12 W Wind Road, Pawling, NY
0.85
Single-Family Home
$688,000
11/24/25
4
4.5
2,920
36 Elm Street, Pawling, NY
0.62
Single-Family Home
$436,000
12/18/25
3
1.5
1,680
7 Juniper Lane, Pawling, NY
0.36
Single-Family Home
$415,000
05/22/26
2
2
2,596
16 Townsend Boulevard, Pawling, NY
0.30
Single-Family Home
$375,000
03/04/26
2
1
1,080

Nearby homes

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Assigned Schools

These are the assigned schools for 99 E Main Street.
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 Pawling

At least 43 Trulia users voted on each feature.

  • 84 % Say parking is easy

  • 82 % Say car is needed

  • 81 % Say yards are well-kept

  • 80 % Say it's dog friendly

  • 78 % Say there's wildlife

  • 76 % Say there's holiday spirit

  • 71 % Say people would walk alone at night

  • 66 % Say neighbors are friendly

  • 65 % Say it's quiet

  • 64 % Say kids play outside

  • 56 % Say they plan to stay for at least 5 years

  • 50 % Say streets are well-lit

  • 47 % Say it's walkable to restaurants

  • 46 % Say there are sidewalks

  • 35 % Say there are community events

  • 21 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Jriina78
    "Pawling is very family friendly. Fun hiking trails and easy to get around if you need public transportation. "
    0
    Flag
  • Suzie F.
    "My work is 3 mins away so my commute is super easy. My husband drives to Poughkeepsie and it’s not bad either. "
    5
    Flag
  • Dawn Z.
    "picking up after there animal, and making sure where they went is cleaned up. It's a nice place for animals and people to walk."
    1
    Flag
  • Trulia User
    "I lived in Pawling my whole life. It's a small and friendly community. My biggest criticism is the sudden increase on the rentals and the housing market, making it near!y impossible for long time locals to maintain cost of living"
    10
    Flag
  • Trulia User
    "People walk their dogs out on the road due to lack of sidewalks. Not very safe. We do have a local park with access to trails and a lake where dogs can go for a swim."
    0
    Flag
  • Francesca T. B.
    "It’s a 35 minute drive to Poughkeepsie. It’s an easy drive straight down Rt. 55. I leave daily by 7:30 and get home by 5. "
    0
    Flag
  • Francesca T. B.
    "I’ve lived here for 20 years. You can walk unafraid. Restaurants, small store, library all close by. "
    0
    Flag
  • Sarah
    "Quiet country life with lots of space For dogs to run around or take a long walk. Plenty of beauty and fresh air for all with reasonable proximity to conveniences. "
    0
    Flag
  • Christine O. l.
    "Good trails, lots of great veterinarians, good doggy day cares. It’s a very country/animal focused and welcoming community. "
    0
    Flag
  • Carolyn C.
    "Have lived in the area for 15 years. Pawling is a very small town surrounded by mountains, hiking trails, art and culture. Very safe and a decidedly suburban vibe. Since I am a city girl born and raised in NYC, I thought I would become very bored very quickly but it has grown on me. I live within 2 hrs drive of the Berkshire Mountains, Long Island Sound and New York City (depending on traffic) but I can come home and revel in the silence. "
    0
    Flag
  • Annmarie P.
    "Good area for commuting to work - Metro North to most major areas. Lots of things to do in the area, friendly, helpful people. Affordable. Municiple water and sewers. "
    0
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Apartments for Rent

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Homes for sale near 99 E Main Street

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Off Market Homes Near 99 E Main Street

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Based on information submitted to the MLS GRID as of 2026-02-06 15:18:24 PST. 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