The 10 Most Expensive Homes on Zillow Massachusetts (2025 Edition)
Massachusetts has long been home to some of the most desirable and prestigious real estate in the country. From iconic Boston brownstones to sprawling coastal estates on Nantucket, the state offers a rich mix of architecture, history, and high-end living. If you’re curious about the top-tier listings in the Bay State, here are the 10 most expensive homes currently for sale on Zillow in Massachusetts, organized from least to most expensive.
10. $23,000,000 – 9 The Ledges Rd, Newton, MA
- Type: Single-family home
- Size: 12,060 sq ft
- Bedrooms/Bathrooms: 6 beds, 10 baths (6 full, 4 half)
- Lot Size: 0.99 acres
- Year Built: 1915 (recently renovated)
Set behind gates on a quiet, tree-lined street, this elegant Georgian Revival estate in Newton showcases timeless grandeur with modern touches. The grand foyer, curved staircase, and formal entertaining rooms are accented by exquisite millwork and original architectural detail. The home features multiple living rooms, a gourmet kitchen with professional-grade appliances, a sunroom, a study, and an expansive primary suite. Outdoor amenities include manicured gardens, wraparound terraces, a heated pool, and a cabana. This home provides both refined luxury and a warm, inviting atmosphere.
9. $23,990,000 – 1, 3, & 3A Reeds Way, Nantucket, MA
- Type: Single-family estate compound
- Size: 8,771 sq ft
- Bedrooms/Bathrooms: 15 beds, 11 baths
- Lot Size: 5.62 acres
A rare opportunity to own one of Nantucket’s largest and most versatile compounds, this three-home estate offers sweeping Atlantic Ocean views and direct beach access. Built to host large family gatherings or provide private guest accommodations, the property includes expansive living areas, multiple kitchens, a heated outdoor pool with poolside kitchen and cabana, and several porches and decks to take in the ocean air. The estate spans a private street that the buyer has the right to rename—truly a legacy property meant for generations to enjoy.
8. $24,000,000 – 55 Fayerweather St, Cambridge, MA
- Type: Single-family home
- Size: 8,728 sq ft
- Bedrooms/Bathrooms: 7 beds, 8.5 baths
- Lot Size: 0.38 acres
- Year Built: 1905
This refined estate in West Cambridge pairs classic 19th-century architectural roots with an artful modern aesthetic. The interiors have been completely reimagined to create open, gallery-like spaces, ideal for contemporary living. The main level features a floating staircase, open-concept kitchen with custom cabinetry, and expansive windows that frame lush views. Each bedroom has its own unique layout and luxurious bath. Additional highlights include a sculptural wine display, elevator access, smart home automation, and serene gardens.
7. $24,500,000 – 333 Lee St, Brookline, MA
- Type: Single-family home
- Size: 20,074 sq ft
- Bedrooms/Bathrooms: 11 beds, 11 baths
- Lot Size: 3.1 acres
- Year Built: 1929
An icon of Brookline real estate, this grand Georgian estate was designed by renowned architect William Truman Aldrich and offers unrivaled scale and historic character. Enter through wrought iron gates to over 3 acres of landscaped grounds and be welcomed into a residence filled with handcrafted woodwork, 10 fireplaces, a formal library, music and dining rooms, and a chef’s kitchen centered on a French-imported Molteni stove. Below ground, a 75-foot indoor pool with spa is connected to the main house by an underground passage—an architectural marvel in itself.
6. $24,950,000 – 2 Marion Ave, Nantucket, MA
- Type: Single-family home
- Size: 6,632 sq ft
- Bedrooms/Bathrooms: 6 beds, 9 baths (6 full, 3 half)
- Lot Size: 1.62 acres
- Year Built: 2019
Located in the heart of Cisco, this coastal masterpiece is designed for indoor-outdoor living. Featuring a primary residence and guest house, this estate offers multiple living areas, wraparound decks, a gourmet kitchen, and floor-to-ceiling windows. Amenities include a climate-controlled wine room, fitness center, surround-sound system, outdoor shower, and landscaped lawn that stretches toward unobstructed Atlantic views. The property is within minutes of Cisco Beach, Bartlett’s Farm, and the island’s most sought-after destinations.
5. $25,000,000 – 25 Dock St, Edgartown, MA
- Type: Single-family home with marina
- Size: 2,347 sq ft
- Bedrooms/Bathrooms: 4 beds, 5 baths (4 full, 1 half)
- Lot Size: 0.25 acres
- Year Built: 2005
Overlooking the heart of Edgartown Harbor, this property merges world-class yachting capabilities with a luxurious residential retreat. The main residence spans three levels with premium finishes, water-facing balconies, and bespoke design. Included is a two-story marina clubhouse, and over 500 feet of dockage—rare for Martha’s Vineyard—suitable for yachts and multiple vessels. It’s a dream estate for boaters or anyone seeking prestige on the water.
4. $29,000,000 – 1 Dalton St #6102, Boston, MA
- Type: Condominium
- Size: 7,557 sq ft
- Bedrooms/Bathrooms: 5 beds, 8 baths (6 full, 2 half)
- Year Built: 2020
Occupying the 61st floor of Boston’s tallest residential tower, this penthouse is a haven in the sky. With 270-degree views across Boston, the Charles River, and the Atlantic, every detail reflects elegance—from soaring ceilings and custom millwork to the expansive private terrace with a fireplace. Access to Four Seasons amenities including valet, spa, in-residence dining, concierge, and pool completes the five-star experience.
3. $33,000,000 – 36 Easton St, Nantucket, MA
- Type: Single-family home
- Size: 4,959 sq ft
- Bedrooms/Bathrooms: 9 beds, 10 baths (9 full, 1 half)
- Lot Size: 0.32 acres
- Year Built: 1851 (recently renovated)
Blending historic charm and modern upgrades, this Nantucket estate delivers the ultimate waterfront lifestyle. The interior showcases exposed beams, custom millwork, gourmet kitchen, spa-like bathrooms, a gym, and entertainment areas. Outdoor living is unmatched with porches, water-facing lawns, and multiple decks. Offered fully furnished (excluding art), it is move-in ready for the most discerning buyer.
2. $38,000,000 – 1 Dalton St #5801/5802, Boston, MA
- Type: Condominium
- Size: 7,848 sq ft
- Bedrooms/Bathrooms: 5 beds, 8 baths (6 full, 2 half)
- Year Built: 2020
The pinnacle of Boston penthouse living, this 58th-floor residence is the result of merging two premium Four Seasons units into a sprawling designer home. Crafted with an artistic eye, it includes a white onyx main kitchen, formal entertaining areas, an art-deco inspired great room, a second full-service catering kitchen, and a temperature-controlled wine vault. Smart home systems, radiant heat floors, and two private terraces elevate the lifestyle. Full access to hotel amenities is included.
1. $40,000,000 – 0 Standish St, Duxbury, MA
- Type: Single-family estate
- Size: 14,000 sq ft
- Bedrooms/Bathrooms: 6 beds, 9 baths (7 full, 2 half)
- Lot Size: 25 acres
- Year Built: 1995
Spanning 25 acres of unmatched privacy, this waterfront sanctuary includes multiple living structures and over 1,000 feet of direct shoreline. The estate features a grand main house, guest cottage, barn with apartment, greenhouse, original antique homestead, and more. Outdoor amenities include a sandy beach, private dock, a pond, gardens, and a fully equipped entertaining pavilion with outdoor kitchen. Just 35 miles from Boston, this is a true legacy estate built for generations.
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Property data sourced from Zillow. Listings are subject to change.