Unless you have a gold-plated income or mountains of cash and investments to fuel an affluent lifestyle, there are some towns that, while nice, are prohibitively expensive. Every state and region has them. New England is no exception. While many of the towns on this list are beautiful, you’re going to pay dearly for that beauty. Check out these towns and if it’s affordable you want, don’t move there. If it’s affluent you want, these are right up your alley. Each town includes current price ranges for basic three and four bedroom homes giving you a sense of just how pricey these towns are. Home prices obtained from Zillow.
25. Freeport, Maine
reeport, Maine, known for its rich history as a shipbuilding and trading center, has evolved into a charming town famous for its outlet shopping and as the home of L.L.Bean’s flagship store. This coastal town offers a picturesque New England experience with its historic architecture, scenic waterfront views, and access to outdoor activities like hiking at Wolfe’s Neck Woods State Park. The town’s community is vibrant, hosting events such as free concerts and festivals that attract both locals and visitors. Home prices reflect the desirability of the area, with 3-bedroom homes priced in the $749,000 to $945,000 range, showcasing its status as an upscale locale with strong real estate values. Despite its modern developments, Freeport retains its small-town charm while offering residents quality schools, artisanal dining options, and proximity to Portland for broader amenities. This blend of history, coastal beauty, and a flourishing community makes Freeport a sought-after location for those seeking both comfort and character.
24. Rockport, Massachusetts
Rockport, Massachusetts, a quintessential New England coastal town, is steeped in maritime history and renowned for its vibrant arts scene and iconic Motif No. 1, a symbol of its fishing and artistic heritage. The town boasts a mix of rugged coastline, sandy beaches, and charming streets lined with galleries, boutiques, and cafes that reflect its longstanding cultural allure. Current home prices in Rockport emphasize its status as an affluent area, with 3-bedroom homes priced in the $700K to $1 million+ range, highlighting its desirability and exclusivity. Despite being a popular tourist destination, Rockport maintains a tight-knit community feel, where residents enjoy seasonal festivals, live music, and easy access to activities like whale watching and sailing. Its proximity to Boston allows for a perfect blend of serene, small-town living with convenient city access. The combination of historic charm, natural beauty, and a strong sense of community makes Rockport a coveted place to call home.
23. Chester, Vermont
Chester, Vermont, is a picturesque town known for its well-preserved historic stone buildings, antique shops, and charming village green that evoke classic New England charm. This quaint town boasts a rich history, with its roots tracing back to the late 18th century as a hub for early settlers. Chester offers residents and visitors a unique blend of rural tranquility and vibrant arts and cultural scenes, featuring local galleries, cozy cafes, and community events throughout the year. The real estate market reflects its growing appeal, with 3-bedroom homes priced in the $459K to $725K range, showcasing that Chester is not an affordable area and signals its status as an affluent choice for homebuyers seeking quality and character. Outdoor enthusiasts enjoy the proximity to hiking trails, ski resorts, and scenic drives through Vermont’s lush landscapes. Chester’s combination of historic architecture, strong community ties, and modern amenities make it an attractive and desirable place to live.
22. Stonington, Connecticut
Stonington, Connecticut, is a historic coastal town that perfectly captures the essence of New England with its scenic waterfront, charming 18th-century buildings, and a rich maritime heritage. Nestled along the southeastern coastline, Stonington offers residents a mix of small-town charm and upscale living, with boutique shops, gourmet restaurants, and art galleries that line its quaint streets. The town’s appeal is evident in its real estate market, where 3-bedroom homes are priced in the $533K to $690K range and can go way up, underlining that it is not an affordable area but rather an affluent community. Stonington’s residents enjoy a wealth of amenities, including access to boating, fishing, and beach activities, as well as cultural events and historical tours. Its proximity to Mystic and larger cities provides additional convenience without compromising its serene, picturesque atmosphere. The blend of rich history, coastal beauty, and high-quality living makes Stonington a highly sought-after location.
21. Kennebunkport, Maine
Kennebunkport, Maine, is a famously affluent coastal town known for its historic charm, upscale lifestyle, and stunning seaside views. Renowned as a vacation spot for presidents and celebrities, this town combines its rich history as a shipbuilding center with a vibrant community that embraces fine dining, boutique shopping, and waterfront activities. The local real estate market highlights its exclusivity, with 3- and 4-bedroom homes priced in the $995K to $2 million+ range and reaching even higher, underscoring that Kennebunkport is far from an affordable area. Residents enjoy a blend of natural beauty, with pristine beaches and picturesque harbor scenes, and cultural experiences, from art galleries to seasonal festivals. The town’s welcoming atmosphere, combined with top-rated schools and easy access to outdoor recreation like sailing and golfing, makes it highly desirable. Kennebunkport’s blend of New England tradition and luxury living ensures it remains one of Maine’s most coveted destinations.
20. Woodstock, Vermont
Woodstock, Vermont, is an idyllic New England town renowned for its classic charm, historical significance, and vibrant community life. Established in the late 18th century, Woodstock showcases beautifully preserved colonial architecture, tree-lined streets, and a picturesque village green that has drawn visitors for generations. The town offers an array of cultural and recreational amenities, including art galleries, specialty shops, farm-to-table dining, and access to nearby outdoor activities like hiking and skiing in the Green Mountains. The real estate market reflects its status as a highly desirable and affluent area, with 3-bedroom homes priced in the $500,000 to $1 million+ range, emphasizing its exclusivity. Residents and visitors alike enjoy attractions such as the Billings Farm & Museum and the Marsh-Billings-Rockefeller National Historical Park, which further enrich Woodstock’s storied appeal. This blend of rich history, scenic beauty, and sophisticated living makes Woodstock a sought-after destination in Vermont.
19. Camden, Maine
Camden, Maine, is a picturesque coastal town known for its stunning harbor views, rolling hills, and a blend of nautical and small-town charm that draws residents and visitors alike. The town boasts a rich history tied to its maritime roots and has long been a destination for those seeking scenic beauty and an upscale lifestyle. Camden offers a vibrant arts and cultural scene, with local theaters, galleries, and seasonal festivals that create a lively community atmosphere. The real estate market in Camden reflects its reputation as an affluent area, with 3 and 4-bedroom homes priced in the $650,000 to $900,000 range and often going well beyond that, underscoring the high demand for property here. Residents enjoy access to top-notch amenities, including boutique shopping, gourmet dining, and outdoor activities like sailing, hiking in Camden Hills State Park, and exploring the picturesque downtown. Camden’s combination of natural splendor, historic charm, and sophisticated living makes it a highly coveted location along Maine’s coastline.
18. New Castle, New Hampshire
New Castle, New Hampshire, is a picturesque coastal town known for its historic charm, scenic beauty, and affluent community. As the smallest and easternmost town in New Hampshire, it comprises a series of islands connected by bridges, offering residents stunning waterfront views and a tranquil environment. The town’s rich history is evident in its well-preserved colonial architecture and landmarks such as Fort Constitution and the Wentworth-Coolidge Mansion. Current real estate trends highlight New Castle’s exclusivity, with 3- and 4-bedroom homes typically priced over $1 million, reflecting its status as a highly desirable and affluent area. The limited availability of homes for sale further underscores the town’s exclusivity and high demand. Residents enjoy access to pristine beaches, boating facilities, and proximity to cultural amenities in nearby Portsmouth, all while benefiting from a close-knit community atmosphere. New Castle’s unique blend of historical significance, natural beauty, and upscale living makes it a coveted destination for discerning homebuyers.
17. Chatham, Massachusetts
Chatham, Massachusetts, is a distinguished town on Cape Cod known for its stunning coastal scenery, rich maritime heritage, and vibrant community life. This historic area is filled with charming, shingle-style homes, pristine beaches, and a bustling downtown lined with boutique shops, art galleries, and gourmet dining. The real estate market in Chatham emphasizes its status as an affluent enclave, with 3- and 4-bedroom homes typically priced from $895,000 to $3 million and beyond, often reaching even higher, highlighting the town’s exclusivity and desirability. Residents enjoy an array of outdoor activities, including sailing, fishing, and scenic bike rides, along with cultural experiences like summer concerts and art shows. Chatham’s location at the “elbow” of Cape Cod provides breathtaking ocean views and access to protected nature preserves. This combination of upscale living, historical charm, and coastal beauty makes Chatham one of the most sought-after towns in Massachusetts.
16. Essex, Connecticut
Essex, Connecticut, is a charming riverside town steeped in history and known for its picturesque streets, colonial architecture, and vibrant community life. Situated along the Connecticut River, Essex has a rich maritime heritage that is celebrated through the town’s renowned historical sites and events like the annual Burning of the Ships parade. The real estate market in Essex reflects its status as an affluent community, with 3- and 4-bedroom homes priced from $500,000 to over $1 million, showcasing the town’s desirability and upscale appeal. Residents enjoy access to a range of amenities, including boutique shopping, fine dining, and cultural attractions such as the Essex Steam Train & Riverboat. The town’s close-knit atmosphere is enhanced by year-round community events, making it an inviting place to live. The blend of history, scenic beauty, and sophisticated living positions Essex as one of Connecticut’s most sought-after towns.
15. Manchester-by-the-Sea, Massachusetts
Manchester-by-the-Sea, Massachusetts, is a picturesque coastal town renowned for its historic charm, pristine beaches, and affluent community. Established in 1645, it boasts a rich maritime heritage, evident in its well-preserved colonial architecture and scenic harbor. The town offers residents and visitors a variety of amenities, including boutique shopping, fine dining, and access to outdoor activities such as sailing, fishing, and hiking in nearby conservation areas. The real estate market reflects its exclusivity, with even modest homes starting around $989,000, while more luxurious properties exceed $4 million, underscoring the area’s high desirability and status as a premium location. Manchester-by-the-Sea’s combination of natural beauty, historical significance, and upscale living makes it a coveted destination for discerning homebuyers.
14. Westport, Massachusetts
Westport, Massachusetts, is a coastal gem known for its scenic farmland, rolling vineyards, and beautiful shoreline along Buzzards Bay. The town’s history as a fishing and agricultural community is still visible in its charming landscape, with historic homes and working farms dotting the countryside. Today, Westport offers a blend of rural charm and upscale living, making it a sought-after destination for those seeking a peaceful yet affluent lifestyle. The real estate market reflects this, with entry-level 3- and 4-bedroom homes typically priced between $570,000 and $1.2 million, while $570,000 to $1 million will generally secure a home. Properties can exceed these prices, highlighting the town’s desirability and exclusivity. Residents enjoy access to scenic outdoor activities, such as hiking, beach-going, and exploring the Westport River, as well as a vibrant local culture with artisanal shops and dining. Westport’s combination of natural beauty, community-focused living, and upscale homes makes it a unique and attractive location.
13. Weston, Vermont
Weston, Vermont, is a quaint town known for its classic New England charm, highlighted by historic buildings, the famed Weston Playhouse, and a welcoming village green. Its peaceful ambiance and strong sense of community make it an appealing place for those seeking a blend of rural beauty and cultural richness. Unlike some of its more exclusive counterparts in New England, Weston is more affordable, with 3- and 4-bedroom homes typically priced from $275,000 to $900,000, positioning it as one of the more accessible towns on a list of generally unaffordable places. This affordability aligns with Vermont’s overall trend of offering lower home prices compared to other New England states. Despite this, Weston’s appeal is strong, featuring local treasures like the Vermont Country Store and nearby outdoor activities such as hiking and skiing. The mix of affordability, historic charm, and proximity to recreational opportunities makes Weston a unique and desirable choice for homebuyers.
12. Lincoln, Massachusetts
Lincoln, Massachusetts, is a picturesque town known for its rich history, scenic landscapes, and affluent community. Established in 1754, Lincoln has preserved its rural charm while offering modern amenities, including top-rated schools, cultural institutions like the deCordova Sculpture Park and Museum, and extensive conservation land with numerous trails for outdoor enthusiasts. The real estate market reflects its exclusivity, with 3- and 4-bedroom homes typically priced from $769,000 to over $4 million, underscoring its status as a highly desirable and affluent area. Residents enjoy a blend of tranquil living and convenient access to Boston, making Lincoln a sought-after location for those seeking both serenity and proximity to urban amenities. The town’s commitment to preserving open space and its strong sense of community contribute to its unique appeal.
11. York, Maine
York, Maine, is a historic coastal town known for its picturesque beaches, charming village centers, and rich colonial heritage. Established in 1630, it stands as one of the oldest towns in the United States, featuring well-preserved architecture and landmarks that reflect its storied past. Today, York offers residents and visitors a blend of natural beauty and modern amenities, including boutique shopping, fine dining, and outdoor activities such as hiking in Mount Agamenticus and enjoying the scenic Nubble Lighthouse. The real estate market reflects its desirability, with 3- and 4-bedroom homes typically priced between $650,000 and $1 million, though properties can exceed this range, highlighting the town’s status as an affluent area. York’s combination of historical charm, coastal living, and community-oriented lifestyle makes it a sought-after destination for discerning homebuyers.
10. Litchfield, Connecticut
Litchfield, Connecticut, is a historic town known for its well-preserved colonial architecture, vibrant cultural scene, and scenic landscapes. Established in 1719, it has played a significant role in American history, notably as the site of the first law school in the United States. Today, Litchfield offers residents and visitors a blend of small-town charm and modern amenities, including boutique shopping, fine dining, and access to outdoor activities such as hiking in the nearby White Memorial Conservation Center. The real estate market reflects its desirability, with 3- and 4-bedroom homes typically starting around $600,000, though properties can exceed this range, highlighting the town’s status as an affluent area. Despite its upscale market, Litchfield remains more affordable compared to some other New England towns, offering a unique combination of historical significance, natural beauty, and community-oriented living.
9. Marblehead, Massachusetts
Marblehead, Massachusetts, is a historic coastal town renowned for its well-preserved colonial architecture, vibrant maritime heritage, and picturesque harbor views. Established in 1629, it has evolved into a sought-after residential area, offering residents a blend of small-town charm and proximity to Boston. The town boasts a variety of amenities, including top-rated schools, boutique shopping, fine dining, and numerous recreational activities such as sailing, fishing, and beach access. The real estate market reflects its desirability, with 3- and 4-bedroom homes typically starting around $900,000 and extending into the multimillion-dollar range, underscoring its status as an affluent community. Marblehead’s combination of historical significance, coastal beauty, and high-quality living continues to attract discerning homebuyers seeking an exceptional lifestyle.
8. Nantucket, Massachusetts
Nantucket, Massachusetts, is a picturesque island renowned for its historic charm, pristine beaches, and exclusive real estate market. The island’s rich maritime history is evident in its well-preserved 19th-century architecture and cobblestone streets. Today, Nantucket offers residents and visitors a blend of upscale amenities, including fine dining, boutique shopping, and cultural institutions like the Nantucket Whaling Museum. The real estate market reflects its status as an affluent area, with modest homes typically starting around $3 million, while more luxurious properties can easily reach into the tens of millions. This high demand is driven by the island’s limited land availability and strict conservation efforts, which preserve its unique character and natural beauty. Despite its exclusivity, Nantucket maintains a close-knit community atmosphere, hosting annual events such as the Daffodil Festival and the Nantucket Wine & Food Festival, which attract visitors from around the world. The combination of historical significance, coastal beauty, and upscale living makes Nantucket a highly coveted destination for discerning homebuyers.
7. Lyme, Connecticut
Lyme, Connecticut, is a picturesque town known for its rolling hills, historic charm, and affluent community. Established in the 17th century, Lyme has preserved its rural character, featuring colonial-era homes and expansive estates. The town offers residents a tranquil lifestyle with access to outdoor activities such as hiking in the Nehantic State Forest and boating on the Connecticut River. The real estate market reflects its desirability, with entry-level homes starting around $400,000, while many properties extend into the millions, underscoring its status as an exclusive area. Despite its upscale market, Lyme maintains a close-knit community atmosphere, hosting local events and supporting a vibrant arts scene. The combination of natural beauty, historical significance, and high-quality living makes Lyme a sought-after destination for discerning homebuyers.
6. Weston, Connecticut
Weston, Connecticut, is a picturesque town known for its rural charm, top-rated schools, and affluent community. Established in the 18th century, Weston has preserved its natural beauty with extensive open spaces and a commitment to low-density housing. The town offers residents a tranquil lifestyle, with amenities such as the Weston Historical Society, the Lachat Town Farm, and access to outdoor activities like hiking in the Devil’s Den Nature Preserve. The real estate market reflects its exclusivity, with homes starting around $650,000 and quickly reaching into the millions, underscoring its status as a highly desirable area. Despite its upscale market, Weston maintains a close-knit community atmosphere, hosting local events and supporting a vibrant arts scene. The combination of natural beauty, historical significance, and high-quality living makes Weston a sought-after destination for discerning homebuyers.
5. Edgartown, Massachusetts
Edgartown, Massachusetts, located on Martha’s Vineyard, is renowned for its historic charm, picturesque harbor, and affluent community. The town boasts well-preserved 19th-century architecture, pristine beaches, and a vibrant cultural scene, making it a sought-after destination for both residents and visitors. The real estate market reflects its exclusivity, with 3- and 4-bedroom homes typically starting around $3 million, underscoring its status as a highly desirable and affluent area. Despite its upscale market, Edgartown maintains a close-knit community atmosphere, hosting local events and supporting a vibrant arts scene. The combination of natural beauty, historical significance, and high-quality living makes Edgartown a sought-after destination for discerning homebuyers.
4. New Canaan, Connecticut
New Canaan, Connecticut, is a picturesque town renowned for its affluent community, top-tier schools, and rich architectural heritage. Established in 1731, it has evolved into a sought-after residential area, offering a blend of suburban tranquility and proximity to New York City. The town boasts a variety of amenities, including upscale shopping, fine dining, and numerous parks and recreational facilities. The real estate market reflects its exclusivity, with 3- and 4-bedroom homes typically starting around $1.2 million, while many properties exceed $3 million, underscoring its status as a highly desirable and affluent area. Despite its upscale market, New Canaan maintains a close-knit community atmosphere, hosting local events and supporting a vibrant arts scene. The combination of natural beauty, historical significance, and high-quality living makes New Canaan a sought-after destination for discerning homebuyers.
3. Greenwich, Connecticut
Greenwich, Connecticut, is a renowned affluent enclave that exudes prestige with its coastal beauty, high-end amenities, and proximity to New York City. Established in 1640, Greenwich boasts a rich history complemented by its modern status as a hub for finance and affluent living. The town features upscale shopping, fine dining, and cultural attractions such as the Bruce Museum, along with scenic parks and marinas that appeal to both residents and visitors. The real estate market mirrors its exclusivity, with even modest 3-bedroom homes typically starting at $1,300,000, while larger properties and estates extend well into the multimillion-dollar range. This reflects the area’s reputation for luxury, where sprawling estates and grand homes dominate the landscape. Despite its upscale atmosphere, Greenwich maintains a strong sense of community and offers top-rated schools and various recreational facilities, solidifying its place as one of the most desirable locations in Connecticut.
2. Wellesley, Massachusetts
Wellesley, Massachusetts, is a prestigious town known for its academic excellence, affluent community, and picturesque suburban environment. Home to renowned institutions like Wellesley College and close to Boston, Wellesley offers a blend of intellectual vibrancy and upscale living. The town features tree-lined streets, boutique shopping, gourmet dining, and a variety of recreational amenities that appeal to its residents. The real estate market in Wellesley reflects its status, with even modest 3- and 4-bedroom homes typically starting around $1,400,000. Most properties consist of expansive estates that can cost several million and often go far beyond, underscoring the area’s exclusivity. Despite its high price point, Wellesley maintains a strong sense of community with excellent schools, cultural events, and beautiful parks, making it a coveted destination for discerning homebuyers seeking both elegance and proximity to urban life.
1. Brookline, Massachusetts
Brookline, Massachusetts, is an affluent town known for its close proximity to Boston, vibrant cultural scene, and blend of urban and suburban charm. Established in 1705, Brookline features a mix of historic and modern architecture, tree-lined streets, and upscale neighborhoods that appeal to both families and professionals. The town offers an array of amenities, including top-rated schools, fine dining, boutique shopping, and green spaces like the beloved Larz Anderson Park and Olmsted-designed Emerald Necklace. Real estate in Brookline reflects its prestige, with even modest single-family homes typically starting at $1,700,000, while the market includes estates priced in the twenty- to thirty-million-dollar range and beyond. This underscores Brookline’s status as a highly desirable and affluent area. Despite its luxury market, Brookline maintains a welcoming, community-focused atmosphere that provides residents with a high quality of life and seamless access to the cultural and economic opportunities of nearby Boston.
