23 Cunningham Drive
Monroe, NY 10950
4 Beds
2.5 Baths
3,424 sqft (on 0.46 acres)
4 Beds
2.5 Baths
3,424 sqft
(on 0.46 acres)
Local Information
- Map ViewExplore the area around 23 Cunningham Drive.
- Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
Description
Discover this stunning 5-bedroom colonial home nestled in the highly desirable Highland Mills area, offering the perfect blend of classic charm and comfort. Spanning over 3,400 square feet of sun-filled living space, this meticulously maintained residence features elegant architectural details, spacious formal and informal entertaining areas, and a versatile finished basement with a private entrance from the backyard—ideal for guests, a home office, or recreation. The generously sized bedrooms provide ample space for rest and relaxation, while the main level seamlessly connects a welcoming living room, a formal dining area, and a bright kitchen. Step outside to enjoy the serene backyard, perfect for gatherings or quiet evenings. Located just moments from Winchester and close to top-rated schools, shopping, parks, and all essential amenities, this home offers both convenience and a vibrant neighborhood atmosphere. Brimming with potential, this Highland Mills gem is a rare opportunity for discerning buyers seeking space, style, and a prime location.
Home Highlights
Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
$213
Listed
21 days ago
Last check for updates: about 12 hours ago
Listing by: MK Realty Inc, (845) 782-0205
David Kraus, (845) 274-3765
Source: OneKey® MLS as distributed by MLS GRID, MLS#1016710
Also Listed on OneKey® MLS as distributed by MLS GRID.
Home Details for 23 Cunningham Drive
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Interior Details Basement: FullNumber 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: 3424 Square Feet |
Appliances & Utilities Utilities: Electricity Connected, Trash Collection Public, Water ConnectedAppliances: Dishwasher, Gas Cooktop, Oven, RefrigeratorDishwasherRefrigerator |
Heating & Cooling Heating: Baseboard,Hot Water,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Baseboard |
Gas & Electric Has Electric on Property |
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Exterior Home Features No Private Pool |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageParking Spaces: 2Parking: Attached |
Water & Sewer Sewer: Public Sewer |
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Cumulative Days on Market: 1Days on Market: 21 |
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Year Built Year Built: 1971 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Colonial |
Building Construction Materials: Brick, Frame, Shake SidingNot Attached Property |
Property Information Parcel Number: 3340012270000001036.0000000 |
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Price List Price: $729,000Price Per Sqft: $213 |
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MLS Status: Active |
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Direction & Address City: Monroe |
School Information Elementary School: Pine Tree Elementary SchoolJr High / Middle School: Monroe-Woodbury Middle SchoolHigh School: Monroe-Woodbury High SchoolHigh School District: Monroe-Woodbury |
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Listing Agent Listing ID: 1016710 |
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Building Area Building Area: 3424 Square Feet |
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Not Senior Community |
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No HOA |
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Lot Area: 0.46 acres |
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Special Conditions: None |
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Listing Agreement Type: Exclusive Right To Sell |
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BasementMls Number: 1016710Attic: ScuttleAttribution Contact: 845-782-0205Showing Requirements: 24 Hour Notice, Occupied |
Market trends in Monroe
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
235
20MoM
Price History for 23 Cunningham Drive
| Date | Price | Event | Source |
|---|---|---|---|
| 06/24/2026 | $729,000 | Listed For Sale | OneKey® MLS as distributed by MLS GRID #1016710 |
| 08/17/2025 | $4,700 | ListingRemoved | Zillow Rentals |
| 07/27/2025 | $4,700 | Listed For Rent | Zillow Rentals |
| 07/24/2025 | $635,000 | Sold | OneKey® MLS as distributed by MLS GRID #848678 |
| 06/11/2025 | $675,000 | Pending | OneKey® MLS as distributed by MLS GRID #848678 |
| 04/14/2025 | $675,000 | Listed For Sale | OneKey® MLS as distributed by MLS GRID #848678 |
| 03/06/2025 | $650,000 | ListingRemoved | OneKey® MLS as distributed by MLS GRID #H6330651 |
| 01/14/2025 | $650,000 | Pending | OneKey® MLS as distributed by MLS GRID #H6330651 |
| 12/02/2024 | $650,000 | PriceChange | OneKey® MLS as distributed by MLS GRID #H6330651 |
| 11/11/2024 | $680,000 | PriceChange | OneKey® MLS as distributed by MLS GRID #H6330651 |
| 10/04/2024 | $700,000 | Listed For Sale | OneKey® MLS as distributed by MLS GRID #H6330651 |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | |
| Assessment | $718,800 |
Home facts updated by county records
Comparable Sales for 23 Cunningham Drive
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.14 | Single-Family Home | $670,000 | 11/03/25 | 4 | 3.5 | 2,000 | |
0.31 | Single-Family Home | $655,000 | 01/13/26 | 4 | 2.5 | 2,278 | |
0.43 | Single-Family Home | $730,000 | 11/25/25 | 4 | 2.5 | 2,350 | |
0.47 | Single-Family Home | $680,000 | 07/21/25 | 4 | 2.5 | 2,275 | |
0.57 | Single-Family Home | $780,000 | 03/26/26 | 4 | 3.5 | 3,146 | |
0.71 | Single-Family Home | $617,500 | 06/11/26 | 5 | 2.5 | 3,302 | |
0.58 | Single-Family Home | $725,000 | 02/27/26 | 5 | 4 | 3,117 | |
0.59 | Single-Family Home | $850,000 | 06/02/26 | 5 | 4 | 3,103 | |
0.61 | Single-Family Home | $560,000 | 10/22/25 | 4 | 2.5 | 2,200 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
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FOR SALE6.93 ACRESListing by: Skyline Real Estate Partners
Assigned Schools
These are the assigned schools for 23 Cunningham Drive.
- Monroe Woodbury Middle School
- 6-8
- Public
- 1559 Students
5/10GreatSchools RatingParent Rating AverageExcellent school with a loving caring environment. Staff is awesome. Classes offer hard work but staff is terrific.Parent Review2y ago - Monroe Woodbury High School
- 9-12
- Public
- 2285 Students
6/10GreatSchools RatingParent Rating AverageMy daughter graduated and was well prepared for university life. I do believe there needs to be more emphasis on building the kids up, not limiting their potential. My daughter‘s counselor stated to her maybe she should think of a back up career as opposed to becoming a veterinarian. While at that meeting, I stated to the counselor excuse me, my daughter can be whatever she wants, and then she tried to backtrack and say well her grades really don’t support that type of career and I told her well. Your job is not to tell her what not to be. Your job is to tell her and advise her on what she needs to do to get there!!! my daughter is about to graduate with the animal science degree and is looking into veterinarian schools. She applied to 15 schools and was accepted to nine. She has proven that she can accomplished anything. She sets her mind to. If any administrators of this school are reading this review, I would encourage you to have a staff meeting and to emphasize on a yearly basis that an educator’s job is to pour in and to provide tools not to limit a students, imagination or mind.Parent Review3mo ago - Pine Tree Elementary School
- 2-5
- Public
- 746 Students
4/10GreatSchools RatingParent Rating AverageIt’s been almost two years and we love the school as well as the hard working staff. I always have been updated on any changes & it’s very easy to email/call when something comes up. My daughter is very happy going to school & riding the bus.Parent Review10mo ago - Sapphire Elementary School
- PK-1
- Public
- 324 Students
NAGreatSchools RatingParent Rating AverageN/AParent Review18y ago 
Check out schools near 23 Cunningham Drive.
What Locals Say about Monroe
At least 292 Trulia users voted on each feature.
88 % Say car is needed
85 % Say parking is easy
81 % Say yards are well-kept
80 % Say there's holiday spirit
76 % Say there's wildlife
75 % Say it's dog friendly
69 % Say it's quiet
69 % Say kids play outside
68 % Say people would walk alone at night
57 % Say they plan to stay for at least 5 years
54 % Say neighbors are friendly
43 % Say it's walkable to restaurants
42 % Say streets are well-lit
41 % Say there are sidewalks
37 % Say there are community events
33 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
David Kraus, MK Realty Inc, (845) 782-0205
Agent Phone: (845) 274-3765
Based on information submitted to the MLS GRID as of 2026-07-15 04:23:11 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
23 Cunningham Drive, Monroe, NY 10950 is a 4 bedroom, 3 bathroom, 3,424 sqft single-family home built in 1971. This property is currently available for sale and was listed by OneKey® MLS as distributed by MLS GRID on Jun 24, 2026. The MLS # for this home is MLS# 1016710.