44 Tiffany Dr, Oak Bluffs, MA, 02557
About This Home
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 improvements 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.
Getting Around
Car-Dependent
Very Limited Transit
Somewhat BikeableSchools
Construction
Condition
- Year built: 1987
Materials
- Foundation: Poured concrete
Notable Dates
- Major remodel year: 2026
Type & Style
- Home type: SingleFamily
- Property subType: Single Family Residence
Interior
Appliances
- Appliances included: Stove: New (Bosch in main house and attached apt),Washer: New (Electrolux in main house and LG in attached apt)
Basement
- Has basement: Yes
- Basement: Full unfinished basement has bulkhead access.
Bedrooms & Bathrooms
- Bedrooms: 4
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
- Main level bedrooms: 1
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
- Fireplace features: 1 Rumford fireplace in LR and a propane stove in family room
Heating
- Heating features: GFHA
Interior Area
- Total structure area: 4,023
- Total interior livable area: 4,023 sqft
Property
Details
- Parcel number: 11
- Zoning: R3
Features
- Exterior features: Deck,Patio,ScrPorch
- Has view: Yes
- View description: None,Trees/Woods
- Frontage type: None
Lot
- Lot size: 1.38 Acres
- Features: Landscaped and wooded
Parking
- Parking features: Ample parking area in front of 2-car garage
- Has garage: Yes
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Hurricane
- Inland Flooding
- Coastal Flooding
- Lightning
- Tsunami
How This Home’s Risks Compare
FEMA Declared Disasters Across Massachusetts Counties
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $14,158 | $169,896 |
| Home Insurance * | $2,029 | $24,348 |
| Property Taxes | $1,161 | $13,932 |
| Electricity | $793 | $9,519 |
| Total | $18,141 | $217,692 |
Income You'd Need if You Spent...
Massachusetts FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
Price History
| Date | Event | Price |
|---|---|---|
| 2026-07-21 | Price change | $2,800,000 |
| 2026-07-03 | Price change | $2,900,000 |
| 2026-06-05 | Price change | $3,095,000 |
| 2026-05-15 | Listed for sale | $3,245,000 |
| 2026-01-06 | Sold | $1,600,000 |
| 2025-11-28 | Pending sale | $1,600,000 |
| 2025-10-31 | Contingent | $1,600,000 |
| 2025-10-31 | Pending sale | $1,600,000 |
| 2025-10-17 | Price change | $1,600,000 |
| 2025-09-29 | Price change | $1,725,000 |
| 2025-08-12 | Price change | $1,825,000 |
| 2025-07-23 | Price change | $1,925,000 |
| 2025-07-03 | Listed for sale | $2,095,000 |
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