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For sale
    • Price cut: $100K (7/21)
    $2,800,000

    44 Tiffany Dr, Oak Bluffs, MA 02557

    4beds
    4,023sqft
    : 
    $16,764/mo
    Get pre-qualified
    Single Family Residence
    Built in 1987
    1.38 Acres Lot
    $2,664,200 Zestimate®
    $696/sqft
    $50/mo HOA

    What's special

    Outdoor showerScreened porchFamily roomDining roomPowder roomEnsuite bedroomGame room
    Tucked away in a serene setting and set on 1.38 private acres, this beautifully renovated 4BR/4.5BA Cape offers over 4,000 sq. ft. of living space with plenty of room for a backyard pool. The main portion of the house includes a gourmet kitchen, multiple entertaining areas including living room, family room, game room, a screened porch, ensuite bedroom and powder room. An attached one-bedroom guest apartment above the garage includes new kitchen, bedroom, living room, washer/dryer and mini-split heat/AC. Recent imporvements outlined in the documents section. It's seamless floor plan is great for entertaining and flows family and guests from an oversized living room with fireplace to the dining room, gourmet kitchen and an inviting family room with cathedral ceiling and propane stove. The 2nd floor includes two large bedrooms (one ensuite), a second full bathroom and new washer/dryer. To the side of the garage is a large separate bonus/variable use room with heat/AC that could be used as an office or game/family room. Property includes a spacious rear patio and deck with access off both the kitchen and screened in porch, as well as an outdoor shower and parking for several cars in the driveway. The lot is large enough in this R3 zone for an in-ground pool. Seller will escrow $50K at closing towards a pool depending on the offer. Assessed value does not reflect extensive 2026 renovations. Title V septic passed inspection 5/12/25 and in-ground propane tank pressured tested in 2025.
    70 days
    |
    749
    |
    45
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Perry Patterson,

    MV Luxury Homes

    Source: LINK,MLS#: 44347

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 5
      • Full bathrooms: 4
      • 1/2 bathrooms: 1
      • Main level bedrooms: 1
      Heating
      • GFHA
      Appliances
      • Included: Stove: New (Bosch in main house and attached apt), Washer: New (Electrolux in main house and LG in attached apt)
      Features
      • AC, Ins, MiniSplit, OSh, Floor 1: Living room, dining room, kitchen, family room, ensuite bedroom with walk-in closet, office/game room with separate entrance., Floor 2: Large ensuite bedroom, a third bedroom, full bathroom and washer/dryer.
      • Flooring: 2
      • Basement: Full unfinished basement has bulkhead access.
      • Fireplace features: 1 Rumford fireplace in LR and a propane stove in family room
      Interior area
      • Total structure area: 4,023
      • Total interior livable area: 4,023 sqft

      Property

      Parking
      • Parking features: Ample parking area in front of 2-car garage
      • Has garage: Yes
      Features
      • Exterior features: Deck, Patio, ScrPorch
      • Has view: Yes
      • View description: None, Trees/Woods
      • Frontage type: None
      Lot
      • Size: 1.38 Acres
      • Features: Landscaped and wooded
      Details
      • Additional structures: The listed square footage includes the attached one bedroom apartment above the garage finished in 2013 and renovated in 2026 and, a 1st floor variable use office/family room adjacent to the garage with heat/AC and entrances to the main house and the driveway.
      • Parcel number: 11
      • Zoning: R3

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Foundation: Poured concrete
      Condition
      • Year built: 1987
      • Major remodel year: 2026

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Town
      • Utilities for property: Cbl

      Community & HOA

      HOA
      • Has HOA: Yes
      • Services included: Road maintenance
      • HOA fee: $600 annually
      Location
      • Region: Oak Bluffs

      Financial & listing details

      • Price per square foot: $696/sqft
      • Tax assessed value: $1,799,600
      • Annual tax amount: $13,000
      • Date on market: 5/15/2026
      • Listing agreement: E

        Estimated market value

        $2,664,200

        $2.53M - $2.80M

        $7,996/mo

        Price history

        DateEventPrice
        7/21/2026Price change$2,800,000-3.4%$696/sqft
        Source: LINK #44347 Report a problem
        7/3/2026Price change$2,900,000-6.3%$721/sqft
        Source: LINK #44347 Report a problem
        6/5/2026Price change$3,095,000-4.6%$769/sqft
        Source: LINK #44347 Report a problem
        5/15/2026Listed for sale$3,245,000+102.8%$807/sqft
        Source: LINK #44347 Report a problem
        1/6/2026Sold$1,600,000$398/sqft
        Source: LINK #43516 Report a problem
        11/28/2025Pending sale$1,600,000$398/sqft
        Source: LINK #43516 Report a problem
        10/31/2025Contingent$1,600,000$398/sqft
        Source: LINK #43516 Report a problem
        10/31/2025Pending sale$1,600,000$398/sqft
        Source: CCIMLS #22503290 Report a problem
        10/17/2025Price change$1,600,000-7.2%$398/sqft
        Source: CCIMLS #22503290 Report a problem
        9/29/2025Price change$1,725,000-5.5%$429/sqft
        Source: LINK #43516 Report a problem
        8/12/2025Price change$1,825,000-5.2%$454/sqft
        Source: LINK #43516 Report a problem
        7/23/2025Price change$1,925,000-8.1%$478/sqft
        Source: LINK #43516 Report a problem
        7/3/2025Listed for sale$2,095,000$521/sqft
        Source: LINK #43516 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$8,818 +3%$1,746,100 +6.6%
        2024$8,563 -0.3%$1,637,300 +0.6%
        2023$8,590 +0.7%$1,626,800 +29.5%
        2022$8,532 +3.1%$1,256,500 +11.9%
        2021$8,279 +5.7%$1,123,300 +6.7%
        2020$7,834 +1%$1,052,900 +4.4%
        2019$7,757 +0.3%$1,008,700 +2.1%
        2018$7,734 +6.5%$987,800 +10.9%
        2017$7,261 +7.9%$890,900 +7.4%
        2016$6,727 +9.9%$829,500 +7.8%
        2015$6,123 +2.2%$769,200 +0.2%
        2014$5,993 +4.5%$767,400 +3.2%
        2013$5,733 +4.3%$743,600
        2012$5,495 -5.3%$743,600 -9.9%
        2011$5,804 +1.6%$825,600 -9%
        2010$5,713 -2.3%$906,800 -6.4%
        2009$5,849 +7.3%$968,300
        2008$5,452 +7.9%$968,300 +7.1%
        2007$5,053 -1.5%$903,900 +20.3%
        2004$5,131 +13.1%$751,200 +15.6%
        2003$4,537 $650,000
        Find assessor info on the county website

        Monthly payment

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 02557

        Getting around

        1 / 100
        Car-Dependent
        25 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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