Skip to content
208 Oakland Avenue, Monroe, photo 1
View all 50 photos
208 Oakland Avenue, photo 2
208 Oakland Avenue, photo 3
208 Oakland Avenue, photo 4
208 Oakland Avenue, photo 5
208 Oakland Avenue, photo 6
208 Oakland Avenue, photo 7
208 Oakland Avenue, photo 8
208 Oakland Avenue, photo 9
208 Oakland Avenue, photo 10
208 Oakland Avenue, photo 11
208 Oakland Avenue, photo 12
208 Oakland Avenue, photo 13
208 Oakland Avenue, photo 14
208 Oakland Avenue, photo 15
208 Oakland Avenue, photo 16
208 Oakland Avenue, photo 17
208 Oakland Avenue, photo 18
208 Oakland Avenue, photo 19
208 Oakland Avenue, photo 20
208 Oakland Avenue, photo 21
208 Oakland Avenue, photo 22
208 Oakland Avenue, photo 23
208 Oakland Avenue, photo 24
208 Oakland Avenue, photo 25
208 Oakland Avenue, photo 26
208 Oakland Avenue, photo 27
208 Oakland Avenue, photo 28
208 Oakland Avenue, photo 29
208 Oakland Avenue, photo 30
208 Oakland Avenue, photo 31
208 Oakland Avenue, photo 32
208 Oakland Avenue, photo 33
208 Oakland Avenue, photo 34
208 Oakland Avenue, photo 35
208 Oakland Avenue, photo 36
208 Oakland Avenue, photo 37
208 Oakland Avenue, photo 38
208 Oakland Avenue, photo 39
208 Oakland Avenue, photo 40
208 Oakland Avenue, photo 41
208 Oakland Avenue, photo 42
208 Oakland Avenue, photo 43
208 Oakland Avenue, photo 44
208 Oakland Avenue, photo 45
208 Oakland Avenue, photo 46
208 Oakland Avenue, photo 47
208 Oakland Avenue, photo 48
208 Oakland Avenue, photo 49
208 Oakland Avenue, photo 50

208 Oakland Avenue

Monroe, NY 10950 · Orange County

Beds
4
Baths
4.5
Sqft
3,510
Status
Active
On site
107 days

Know your budget before you tour. Get pre-qualified

About this home

208 Oakland, Monroe Specifications: 4 Bedrooms | 4.5 Bathrooms | 2 Kitchens | 2-Car Garage Key Layout Features: Interior Residential Elevator(Basement to First Floor)l Lower-Level Accessory Apartment with Walk-Out Welcome to 208 Oakland, a beautifully maintained 2004 residence offering private living and exceptional layout flexibility. Spanning three finished levels, this property is uniquely tailored for multi-generational living or guest accommodations. A standout mechanical feature is the fully integrated residential elevator, providing seamless internal transit directly from the the lower level to the main first floor. Main Level Living Spaces The home opens into a grand two-story foyer featuring double-height ceilings that maximize natural light. Hardwood flooring extends throughout the principal formal and casual areas: Formal Living Room: Located immediately to the left of the foyer, this bright and inviting sitting room features large front-facing windows and an elegant pocket glass paned door, providing a quiet space separate from the main living areas. Formal Dining Room: Positioned to the right of the entryway, this sophisticated space features French doors, offering an ideal setting for hosting dinners and large gatherings. Epicurean Kitchen: Moving toward the rear of the home, the spacious kitchen is outfitted with custom wood cabinetry, premium granite countertops, a unique handmade backsplash, and stainless steel appliances. The eat-in kitchen is perfectly designed for seamless indoor-outdoor living. The dining area flows through a sliding glass door onto a spacious elevated deck. Enjoy peaceful views of your private tree-lined backyard. Family Room: Directly open to the kitchen area, this relaxing everyday living space features a clean gas fireplace and a large bank of windows framing views of the private rear property. Main Floor Conveniences: A dedicated laundry room, the elevator access station, and an updated powder room are all conveniently located on this level. Upper Level Private Quarters An open staircase leads to the second floor, which serves as the main sleeping area and includes a large hallway linen closet: Primary Bedroom Suite: A spacious master retreat featuring a vaulted ceiling and an expansive, custom-organized walk-in closet. The attached en-suite bathroom is equipped with a deep soaking tub, a separate stall shower, and a large vanity. Secondary Bedrooms: Two additional nice-sized bedrooms offer excellent natural light and generous closet storage, sharing access to a pristine full hallway bathroom. Lower Level (Legal Accessory Apartment) The finished walk-out basement functions as a complete, independent living space equipped with its own dedicated systems and layout: Living & Dining Area: An open-concept living space centered around a tile-surround fireplace, complete with a walk-out straight to the backyard patio area. Second Kitchen: A fully operational custom kitchen featuring matching wood cabinetry, granite countertops and premium stainless steel appliances. The central peninsula provides casual counter seating. Bed & Bath: Includes one private, spacious bedroom and two beautifully tiled full bathrooms. Elevator Station: The residential elevator begins on this floor, offering effortless internal transport straight up to the first floor. Top Two Floors: Serviced by traditional baseboard heating and a central air conditioning system. Basement Level: Operates completely independently, powered by its own dedicated forced-air heating system and separate central AC unit. Situated on a private, landscaped lot, the exterior features manicured lawns, mature trees, and elegant stone-paver walkways. Outdoor entertaining is anchored by a large upper deck complete with a permanent, hard-top gazebo pavilion for covered dining, the two sheds in backyard are included in the sale, two kitchens, deck, gazebo. Wired Alarm System in the Entire house,

Listed with Preferred Properties Real Esta · Yakov Winkler · Source: OneKey MLS

One Key MLS

Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Sep 17, 2026, 7:08 PM ET. ©2026 One Key MLS.

Estimate Your Monthly Payment

Estimate your mortgage payment, including the principal and interest, taxes, insurance, HOA, and Private Mortgage Insurance.

$5,899.37Total / mo

Estimated Monthly Payment

Principal & interest
$4,181.95 (70.9%)
Taxes
$1,517.42 (25.7%)
Insurance
$200.00 (3.4%)

Representative rates

Representative rates only, indicative for comparison. Edit the interest rate for your own quote; your lender’s numbers vary with credit, points, and insurance.

Never miss a property

Be the first to know when a Orange County home hits the market.

Save this search

Market Insights

The market around Monroe, NY

Current Listings

New in the last 30 days

56

Sep 2026

Average Price

Active listings

$729,411

Sep 2026

Average Days on Market

Active listings

91 days

Sep 2026

Computed from 274 active OneKey MLS listings in Monroe, NY.

Similar homes in Orange County

See all 757
110-112 S Jacqueline Street, New Windsor, NY
Photo 1 of 6
Coming SoonNew

$619,900

5 Bed • 2 Bath

110-112 S Jacqueline Street

New Windsor, NY 12553

Listed with RE/MAX Benchmark Realty Group

7 Abbey Road, Warwick, NY
Photo 1 of 3
Coming SoonNew

$629,900

3 Bed • 2 Bath • 1,440 Sq. Ft.

7 Abbey Road

Warwick, NY 10990

Listed with Howard Hanna Rand Realty

10 Willow Court, Tuxedo Park, NY
Photo 1 of 50
Coming SoonNew

$699,999

2 Bed • 3 Bath • 2,140 Sq. Ft.

10 Willow Court

Tuxedo Park, NY 10987

Listed with Ellis Sotheby's Intl Realty