Connecticut’s real estate landscape has transformed dramatically over the past 15 years, and new Zillow Home Value Index pinpoints the 24 towns leading that shift. From quiet shoreline retreats to exclusive commuter suburbs, the towns on this list have emerged as the most expensive places to live in the state as of 2025.
The rankings are based on historical home value estimates spanning from 2010 to 2025, highlighting long-term appreciation as well as sharp jumps in recent years. Whether driven by pandemic-era demand, top-rated schools, or idyllic scenery, each town tells a different story about how Connecticut’s housing market has evolved. If you’re watching market trends, planning a move, or simply curious where wealth is flowing in the Nutmeg State, this data-rich roundup offers plenty of insight.
24. Newtown – 79% Home Price Increase Since 2010
- 2010: $362,738
- 2011: $349,476 (-$13,262, -3.66% from previous year)
- 2012: $348,041 (-$1,435, -0.41% from previous year)
- 2013: $348,648 (+$607, +0.17% from previous year)
- 2014: $357,879 (+$9,231, +2.65% from previous year)
- 2015: $367,134 (+$9,255, +2.59% from previous year)
- 2016: $379,593 (+$12,459, +3.39% from previous year)
- 2017: $394,885 (+$15,292, +4.03% from previous year)
- 2018: $420,962 (+$26,077, +6.60% from previous year)
- 2019: $445,094 (+$24,132, +5.73% from previous year)
- 2020: N/A
- 2021: $545,689 (+$100,595, +22.60% from 2019)
- 2022: $603,414 (+$57,725, +10.58% from previous year)
- 2023: $625,655 (+$22,241, +3.68% from previous year)
- 2024: $634,953 (+$9,298, +1.49% from previous year)
- 2025: $649,013 (+$14,060, +2.21% from previous year)
Newtown’s home prices have nearly doubled over the past 15 years, rising from $362,738 in 2010 to $649,013 in 2025. While early years saw slower growth and even mild declines, momentum picked up significantly post-2017. The surge between 2019 and 2021 was particularly notable, with a jump of over 22%, likely driven by a surge in suburban demand during the pandemic.
Newtown – Consistent Growth in a Classic Connecticut Town
Newtown is a quintessential New England town located in Fairfield County, blending rich colonial history with modern conveniences. Its proximity to Danbury and relatively easy access to New York City make it a desirable choice for commuters who want more space and greenery without sacrificing accessibility. The town also offers a strong public school system, low crime rates, and a historic town center that adds to its charm and community appeal.
Between 2019 and 2021, Newtown experienced one of the most dramatic growth spurts in recent memory, likely driven by pandemic-era lifestyle changes. Families sought more space and home offices, and Newtown’s balance of affordability and quality of life proved attractive. While the pace of growth has slowed since then, the town continues to show modest appreciation, suggesting long-term stability and continued interest from buyers.
23. Woodbridge – 37% Home Price Increase Since 2010
- 2010: $477,037
- 2011: $455,688 (-$21,349, -4.48% from previous year)
- 2012: $442,949 (-$12,739, -2.80% from previous year)
- 2013: $437,468 (-$5,481, -1.24% from previous year)
- 2014: $444,695 (+$7,227, +1.65% from previous year)
- 2015: $453,736 (+$9,041, +2.03% from previous year)
- 2016: $468,142 (+$14,406, +3.17% from previous year)
- 2017: $488,705 (+$20,563, +4.39% from previous year)
- 2018: $522,734 (+$34,029, +6.96% from previous year)
- 2019: $549,588 (+$26,854, +5.14% from previous year)
- 2020: N/A
- 2021: $642,195 (+$92,607, +16.85% from 2019)
- 2022: $693,344 (+$51,149, +7.96% from previous year)
- 2023: $704,900 (+$11,556, +1.67% from previous year)
- 2024: $658,074 (-$46,826, -6.64% from previous year)
- 2025: $651,581 (-$6,493, -0.99% from previous year)
Home prices in Woodbridge rose 37% from 2010 to 2025, with the most substantial appreciation occurring between 2019 and 2021. That period brought a sharp uptick in demand, likely from families leaving more urban areas for quiet, spacious communities. Recent years, however, reflect a price correction, with values dipping below their 2022 peak.
Woodbridge – Price Peaks and Post-Boom Cooldown
Woodbridge is a leafy, upscale suburb of New Haven known for its excellent public schools and large, private lots. It attracts professionals and academics, particularly those affiliated with nearby Yale University. The town has no commercial strip of its own, contributing to its tranquil, residential atmosphere.
From 2019 to 2021, home values climbed nearly 17%, driven by pandemic-related shifts in housing priorities. Demand for spacious single-family homes surged, but that boom was followed by a noticeable correction. Though the town’s housing market has cooled, Woodbridge remains a top-tier destination with enduring appeal for buyers seeking quiet sophistication.
22. Old Saybrook – 95% Home Price Increase Since 2010
- 2010: $335,570
- 2011: $322,756 (-$12,814, -3.82% from previous year)
- 2012: $320,468 (-$2,288, -0.71% from previous year)
- 2013: $326,030 (+$5,562, +1.74% from previous year)
- 2014: $338,799 (+$12,769, +3.92% from previous year)
- 2015: $348,699 (+$9,900, +2.92% from previous year)
- 2016: $364,119 (+$15,420, +4.42% from previous year)
- 2017: $382,476 (+$18,357, +5.04% from previous year)
- 2018: $411,074 (+$28,598, +7.48% from previous year)
- 2019: $446,264 (+$35,190, +8.56% from previous year)
- 2020: N/A
- 2021: $565,406 (+$119,142, +26.70% from 2019)
- 2022: $626,522 (+$61,116, +10.81% from previous year)
- 2023: $645,928 (+$19,406, +3.10% from previous year)
- 2024: $651,736 (+$5,808, +0.90% from previous year)
- 2025: $653,527 (+$1,791, +0.27% from previous year)
Old Saybrook has seen one of the largest long-term home price increases on this list, climbing 95% from 2010 to 2025. The steepest spike came between 2019 and 2021, when values jumped nearly 27% in just two years. Since then, appreciation has slowed, but prices have continued to inch upward year after year.
Old Saybrook – Steady Demand Along the Connecticut Shoreline
Located where the Connecticut River meets Long Island Sound, Old Saybrook is known for its maritime history and scenic beauty. The town features charming colonial architecture, coastal views, and a vibrant small-town atmosphere. These qualities have made it a perennial favorite for retirees, second-home buyers, and locals looking for shoreline living.
The 2019–2021 surge reflects pandemic-era demand for waterfront properties, which drove a surge in competition and prices. Inventory remains tight, helping sustain values even as the broader market cools. While future price gains may be more modest, Old Saybrook’s desirability suggests long-term value will remain high.
21. Cornwall – 94% Home Price Increase Since 2010
- 2010: $337,928
- 2011: $327,176 (-$10,752, -3.18% from previous year)
- 2012: $326,459 (-$717, -0.22% from previous year)
- 2013: $332,959 (+$6,500, +1.99% from previous year)
- 2014: $344,298 (+$11,339, +3.41% from previous year)
- 2015: $354,088 (+$9,790, +2.84% from previous year)
- 2016: $369,134 (+$15,046, +4.25% from previous year)
- 2017: $389,089 (+$19,955, +5.41% from previous year)
- 2018: $420,442 (+$31,353, +8.06% from previous year)
- 2019: $450,825 (+$30,383, +7.23% from previous year)
- 2020: N/A
- 2021: $569,932 (+$119,107, +26.42% from 2019)
- 2022: $634,379 (+$64,447, +11.31% from previous year)
- 2023: $663,928 (+$29,549, +4.66% from previous year)
- 2024: $666,843 (+$2,915, +0.44% from previous year)
- 2025: $655,543 (-$11,300, -1.69% from previous year)
Cornwall saw prices nearly double from 2010 to 2025, peaking just after a huge 26% leap between 2019 and 2021. This bump was part of a larger pattern across Litchfield County, where buyers turned to the hills for space and privacy. Prices have cooled slightly since 2023, but the town’s long-term growth remains remarkable.
Cornwall – Nature, Quiet, and a Market Surge
Cornwall is a rural haven in northwestern Connecticut, famous for its covered bridge and proximity to the Appalachian Trail. Its natural beauty and sense of seclusion make it a popular choice for New Yorkers seeking weekend retreats. Many properties here offer acres of land, scenic views, and peaceful surroundings.
The town’s real estate boom came during the early pandemic years when demand for remote, low-density living spiked. As a result, prices jumped sharply, especially between 2019 and 2021. While the pace has slowed and 2025 saw a modest pullback, Cornwall’s market remains elevated compared to historical norms and continues to draw interest.
20. New Preston – 70% Home Price Increase Since 2010
- 2010: $387,133
- 2011: $378,936 (-$8,197, -2.12% from previous year)
- 2012: $379,513 (+$577, +0.15% from previous year)
- 2013: $388,270 (+$8,757, +2.31% from previous year)
- 2014: $402,536 (+$14,266, +3.68% from previous year)
- 2015: $414,797 (+$12,261, +3.05% from previous year)
- 2016: $432,803 (+$18,006, +4.34% from previous year)
- 2017: $456,638 (+$23,835, +5.51% from previous year)
- 2018: $494,072 (+$37,434, +8.20% from previous year)
- 2019: $530,056 (+$35,984, +7.28% from previous year)
- 2020: N/A
- 2021: $670,404 (+$140,348, +26.48% from 2019)
- 2022: $745,845 (+$75,441, +11.25% from previous year)
- 2023: $781,034 (+$35,189, +4.72% from previous year)
- 2024: $702,690 (-$78,344, -10.03% from previous year)
- 2025: $660,299 (-$42,391, -6.03% from previous year)
New Preston’s home values soared by more than 26% between 2019 and 2021, reflecting a pandemic-fueled wave of interest in peaceful, upscale rural towns. Since hitting a peak in 2023, prices have declined significantly, with a two-year drop totaling more than 15%. Despite the cooling trend, home values are still up by 70% from their 2010 levels, showing the town’s long-term attractiveness.
New Preston – A Coveted Retreat with Cooling Prices
Nestled in the hills of Litchfield County, New Preston is a small village that’s part of the town of Washington. It has long been a magnet for artists, creatives, and city dwellers looking for a scenic weekend home. The village overlooks Lake Waramaug, one of Connecticut’s most picturesque and sought-after locations, which adds a significant premium to local real estate.
The recent declines in price may reflect a normalization rather than a crisis. After several years of above-average appreciation, the market is finding its footing at a new, higher baseline. For buyers looking for a blend of rustic luxury and tranquil surroundings, New Preston still checks many boxes—and continues to command one of the highest price tags in the region.
19. Sharon – 67% Home Price Increase Since 2010
- 2010: $404,838
- 2011: $397,053 (-$7,785, -1.92% from previous year)
- 2012: $397,854 (+$801, +0.20% from previous year)
- 2013: $407,238 (+$9,384, +2.36% from previous year)
- 2014: $422,334 (+$15,096, +3.71% from previous year)
- 2015: $435,329 (+$12,995, +3.08% from previous year)
- 2016: $454,327 (+$18,998, +4.36% from previous year)
- 2017: $479,613 (+$25,286, +5.57% from previous year)
- 2018: $518,699 (+$39,086, +8.15% from previous year)
- 2019: $556,161 (+$37,462, +7.22% from previous year)
- 2020: N/A
- 2021: $703,615 (+$147,454, +26.52% from 2019)
- 2022: $782,780 (+$79,165, +11.25% from previous year)
- 2023: $820,002 (+$37,222, +4.76% from previous year)
- 2024: $728,099 (-$91,903, -11.21% from previous year)
- 2025: $676,804 (-$51,295, -7.04% from previous year)
Sharon experienced a dramatic surge in home prices during the early 2020s, with values jumping over 26% between 2019 and 2021 alone. After peaking in 2023, prices have retreated, bringing the 2025 median to $676,804. Even with the decline, the town has posted a strong 67% increase since 2010, underlining its enduring desirability.
Sharon – Rural Luxury with a Price Reset
Sharon is located in the far northwest corner of Connecticut, part of the scenic Litchfield Hills region. Known for its pastoral landscapes and elegant estates, the town has historically attracted second-home buyers from New York City. It offers a slower pace of life and plenty of privacy—key qualities that gained value during the pandemic.
As demand peaked in 2021 and 2022, Sharon’s real estate market saw prices rise rapidly. However, the town’s sharp double-digit price drops in the past two years suggest the high-end market may have overheated. While values are off their peak, the town still boasts some of the highest per-square-foot property prices in rural Connecticut.
18. Stamford – 62% Home Price Increase Since 2010
- 2010: $419,994
- 2011: $399,623 (-$20,371, -4.85% from previous year)
- 2012: $389,688 (-$9,935, -2.49% from previous year)
- 2013: $391,476 (+$1,788, +0.46% from previous year)
- 2014: $404,877 (+$13,401, +3.42% from previous year)
- 2015: $412,959 (+$8,082, +2.00% from previous year)
- 2016: $431,659 (+$18,700, +4.53% from previous year)
- 2017: $453,926 (+$22,267, +5.16% from previous year)
- 2018: $489,495 (+$35,569, +7.84% from previous year)
- 2019: $522,701 (+$33,206, +6.78% from previous year)
- 2020: N/A
- 2021: $639,825 (+$117,124, +22.41% from 2019)
- 2022: $695,688 (+$55,863, +8.73% from previous year)
- 2023: $708,043 (+$12,355, +1.78% from previous year)
- 2024: $698,226 (-$9,817, -1.39% from previous year)
- 2025: $680,157 (-$18,069, -2.59% from previous year)
Stamford’s housing market has climbed steadily over the past decade and a half, recording a 62% gain since 2010. The largest spike occurred between 2019 and 2021, when home prices jumped more than 22%, driven by its appeal to professionals seeking a mix of urban and suburban amenities.
Stamford – A Business Hub with Residential Momentum
Stamford is the economic engine of southwestern Connecticut, hosting the headquarters of numerous corporations while offering high-end neighborhoods and shoreline living. It’s often seen as an alternative to New York City, with a strong commuter rail link and a growing number of residents who work from home. The city’s blend of apartments, condos, and single-family homes means there’s something for a wide range of buyers.
The pandemic drove up demand as New Yorkers sought more space, helping spark a massive rise in prices through 2021. That trend has cooled somewhat, with small price drops in 2024 and 2025, suggesting the market is balancing out. Still, Stamford remains one of Connecticut’s most dynamic real estate markets and a perennial hotspot for investors and homebuyers alike.
17. Sherman – 72% Home Price Increase Since 2010
- 2010: $401,598
- 2011: $390,847 (-$10,751, -2.68% from previous year)
- 2012: $389,522 (-$1,325, -0.34% from previous year)
- 2013: $395,928 (+$6,406, +1.64% from previous year)
- 2014: $408,975 (+$13,047, +3.30% from previous year)
- 2015: $419,951 (+$10,976, +2.68% from previous year)
- 2016: $437,597 (+$17,646, +4.20% from previous year)
- 2017: $460,608 (+$23,011, +5.26% from previous year)
- 2018: $493,912 (+$33,304, +7.23% from previous year)
- 2019: $522,955 (+$29,043, +5.88% from previous year)
- 2020: N/A
- 2021: $648,949 (+$125,994, +24.09% from 2019)
- 2022: $718,433 (+$69,484, +10.71% from previous year)
- 2023: $736,959 (+$18,526, +2.58% from previous year)
- 2024: $710,903 (-$26,056, -3.54% from previous year)
- 2025: $692,100 (-$18,803, -2.65% from previous year)
Home prices in Sherman climbed over 72% from 2010 to 2025, with the most rapid gains coming between 2019 and 2021. The town’s rural appeal, lakefront properties, and low population density made it a target during the pandemic’s real estate boom, and although recent years have seen some retreat, values remain historically high.
Sherman – Scenic Isolation Fuels Price Growth
Sherman is tucked in Connecticut’s quiet northwest corner, bordered by New York’s Putnam County and nestled along the shores of Candlewood Lake. Its appeal lies in its natural beauty, large parcels, and peaceful atmosphere—qualities that saw a premium in the remote-work era. The town lacks major development, and that’s exactly what attracts its residents.
Sherman’s property values shot up as buyers sought rural sanctuaries close to the city but away from the crowds. Although prices have dipped slightly in 2024 and 2025, they remain far above pre-pandemic levels. This suggests that while some speculative heat has left the market, Sherman continues to benefit from a lasting shift in buyer priorities.
16. Madison – 73% Home Price Increase Since 2010
- 2010: $413,859
- 2011: $395,895 (-$17,964, -4.34% from previous year)
- 2012: $388,344 (-$7,551, -1.91% from previous year)
- 2013: $389,692 (+$1,348, +0.35% from previous year)
- 2014: $399,720 (+$10,028, +2.57% from previous year)
- 2015: $407,709 (+$7,989, +2.00% from previous year)
- 2016: $422,520 (+$14,811, +3.63% from previous year)
- 2017: $442,299 (+$19,779, +4.68% from previous year)
- 2018: $472,298 (+$29,999, +6.78% from previous year)
- 2019: $498,697 (+$26,399, +5.59% from previous year)
- 2020: N/A
- 2021: $615,169 (+$116,472, +23.36% from 2019)
- 2022: $677,826 (+$62,657, +10.18% from previous year)
- 2023: $703,046 (+$25,220, +3.72% from previous year)
- 2024: $703,556 (+$510, +0.07% from previous year)
- 2025: $696,321 (-$7,235, -1.03% from previous year)
Madison’s home prices climbed by nearly three-quarters over 15 years, with a significant jump between 2019 and 2021. The coastal town’s appeal was magnified during the pandemic as buyers sought lifestyle upgrades, driving a 23% increase in home values over that two-year stretch.
Madison – Coastal Comfort with Long-Term Appeal
Madison sits along Long Island Sound and is known for its beaches, vibrant arts scene, and highly ranked public schools. Hammonasset Beach State Park and a walkable downtown add to the town’s draw, making it a top choice for both retirees and families. Its classic shoreline homes and small-town feel have long made it one of the Connecticut coast’s most desirable markets.
The town saw explosive price growth from 2019 to 2021 as demand for coastal properties surged. More recent years show signs of leveling off, suggesting the market may be entering a more sustainable phase. With enduring lifestyle appeal and limited supply, Madison continues to command premium home values in the state.
15. Bridgewater – 53% Home Price Increase Since 2010
- 2010: $472,041
- 2011: $460,777 (-$11,264, -2.39% from previous year)
- 2012: $460,027 (-$750, -0.16% from previous year)
- 2013: $468,982 (+$8,955, +1.95% from previous year)
- 2014: $485,447 (+$16,465, +3.51% from previous year)
- 2015: $500,225 (+$14,778, +3.04% from previous year)
- 2016: $521,650 (+$21,425, +4.28% from previous year)
- 2017: $549,959 (+$28,309, +5.43% from previous year)
- 2018: $591,738 (+$41,779, +7.60% from previous year)
- 2019: $633,850 (+$42,112, +7.12% from previous year)
- 2020: N/A
- 2021: $801,730 (+$167,880, +26.48% from 2019)
- 2022: $891,528 (+$89,798, +11.20% from previous year)
- 2023: $934,203 (+$42,675, +4.79% from previous year)
- 2024: $786,815 (-$147,388, -15.78% from previous year)
- 2025: $724,830 (-$61,985, -7.88% from previous year)
Bridgewater saw explosive growth in home values from 2019 to 2021, with prices surging by over 26% in that period alone. That spike continued into 2022 and 2023 before correcting sharply in the two years that followed. Despite recent volatility, home prices are still 53% higher than they were in 2010.
Bridgewater – A Market of High Peaks and Deep Corrections
Bridgewater, located in Litchfield County, is one of the smallest towns in Connecticut by population, known for its rolling hills, open space, and country charm. Its scenic views and tranquil lifestyle have made it a haven for second-home buyers and wealthy New Yorkers seeking refuge from city life. With no traffic lights and a tightly preserved rural character, it offers an escape that became especially valuable during the early pandemic years.
The intense demand between 2020 and 2022 sent prices soaring to unsustainable levels. The recent drop, particularly the 15% decline in 2024, reflects a market recalibration more than a loss of interest. Bridgewater remains desirable for its unique mix of seclusion, beauty, and prestige—even if prices are now moderating.
14. Lyme – 83% Home Price Increase Since 2010
- 2010: $406,863
- 2011: $394,959 (-$11,904, -2.93% from previous year)
- 2012: $392,821 (-$2,138, -0.54% from previous year)
- 2013: $397,901 (+$5,080, +1.29% from previous year)
- 2014: $408,529 (+$10,628, +2.67% from previous year)
- 2015: $417,165 (+$8,636, +2.11% from previous year)
- 2016: $432,388 (+$15,223, +3.65% from previous year)
- 2017: $452,754 (+$20,366, +4.71% from previous year)
- 2018: $481,947 (+$29,193, +6.45% from previous year)
- 2019: $508,027 (+$26,080, +5.41% from previous year)
- 2020: N/A
- 2021: $631,374 (+$123,347, +24.28% from 2019)
- 2022: $698,924 (+$67,550, +10.70% from previous year)
- 2023: $726,606 (+$27,682, +3.96% from previous year)
- 2024: $739,152 (+$12,546, +1.73% from previous year)
- 2025: $744,260 (+$5,108, +0.69% from previous year)
Lyme has posted steady long-term gains, with home prices rising 83% from 2010 to 2025. The most dramatic jump came between 2019 and 2021, when values climbed more than 24%, a pattern echoed in many picturesque shoreline communities across the state.
Lyme – Secluded Shoreline with Historic Charm
Set along the Connecticut River and known for its rolling woodlands, nature preserves, and historic homes, Lyme is a quiet enclave with deep colonial roots. It’s long been a destination for retirees, nature lovers, and buyers looking to live close to the water without the density of larger towns.
Housing demand surged during the early pandemic years, particularly from buyers looking for outdoor access and solitude. Lyme fit the bill perfectly and saw home values rise accordingly. Although growth has slowed since 2022, prices have remained high—likely due to the town’s limited housing stock and consistently strong appeal to affluent, privacy-minded buyers.
13. Redding – 70% Home Price Increase Since 2010
- 2010: $490,838
- 2011: $470,914 (-$19,924, -4.06% from previous year)
- 2012: $455,761 (-$15,153, -3.22% from previous year)
- 2013: $459,461 (+$3,700, +0.81% from previous year)
- 2014: $473,486 (+$14,025, +3.05% from previous year)
- 2015: $485,354 (+$11,868, +2.51% from previous year)
- 2016: $504,318 (+$18,964, +3.91% from previous year)
- 2017: $530,642 (+$26,324, +5.22% from previous year)
- 2018: $569,624 (+$38,982, +7.35% from previous year)
- 2019: $602,803 (+$33,179, +5.82% from previous year)
- 2020: N/A
- 2021: $748,395 (+$145,592, +24.15% from 2019)
- 2022: $826,901 (+$78,506, +10.49% from previous year)
- 2023: $862,374 (+$35,473, +4.29% from previous year)
- 2024: $847,741 (-$14,633, -1.70% from previous year)
- 2025: $834,142 (-$13,599, -1.60% from previous year)
Redding’s home values grew 70% from 2010 to 2025, with a particularly sharp increase between 2019 and 2021 of over 24%. Although the last two years have seen modest price declines, values remain far above their pre-pandemic levels.
Redding – A Forested Escape with a Commuter’s Edge
Located in Fairfield County, Redding is often described as “the Vermont of Connecticut” thanks to its preserved woodlands and rustic charm. It offers easy access to major highways and train lines into New York City, making it a favorite among professionals who want space without giving up convenience. The town is also known for its conservation efforts and rural feel.
Home prices climbed steeply during the early 2020s as Redding’s appeal to remote workers and city escapees grew. While prices have ticked down since 2023, the town continues to command high values due to its unique blend of natural beauty, strong public schools, and accessibility. It’s likely to remain a top-tier choice for buyers looking for the best of both worlds.
12. Salisbury – 80% Home Price Increase Since 2010
- 2010: $494,866
- 2011: $487,257 (-$7,609, -1.54% from previous year)
- 2012: $486,374 (-$883, -0.18% from previous year)
- 2013: $500,650 (+$14,276, +2.94% from previous year)
- 2014: $522,542 (+$21,892, +4.37% from previous year)
- 2015: $535,984 (+$13,442, +2.57% from previous year)
- 2016: $551,745 (+$15,761, +2.94% from previous year)
- 2017: $575,572 (+$23,827, +4.32% from previous year)
- 2018: $608,451 (+$32,879, +5.71% from previous year)
- 2019: $639,044 (+$30,593, +5.03% from previous year)
- 2020: N/A
- 2021: $792,015 (+$152,971, +23.94% from 2019)
- 2022: $872,261 (+$80,246, +10.13% from previous year)
- 2023: $892,314 (+$20,053, +2.30% from previous year)
- 2024: $901,813 (+$9,499, +1.06% from previous year)
- 2025: $889,931 (-$11,882, -1.32% from previous year)
Salisbury’s home values grew by 80% from 2010 to 2025, with the sharpest appreciation occurring between 2019 and 2021 when prices soared nearly 24%. The market has since stabilized, with modest growth followed by a slight dip in 2025, suggesting the town is settling into a new pricing tier.
Salisbury – Prestige and Privacy in the Northwest Hills
Salisbury, nestled in the northwestern corner of the state, is prized for its beautiful countryside, proximity to the Berkshires, and classic New England ambiance. The town is home to several prestigious boarding schools and has a long-standing reputation as a quiet retreat for wealthy residents. Lakeville, one of its villages, adds lakeside luxury to the mix.
As with other upscale rural towns, Salisbury’s home prices jumped during the pandemic as affluent buyers looked to escape the city. With its limited inventory and timeless charm, the town has retained much of that value. Though 2025 shows a small decline, Salisbury remains among the most desirable and expensive places to live in Connecticut.
11. Fairfield – 64% Home Price Increase Since 2010
- 2010: $554,978
- 2011: $534,124 (-$20,854, -3.76% from previous year)
- 2012: $517,747 (-$16,377, -3.07% from previous year)
- 2013: $539,765 (+$22,018, +4.25% from previous year)
- 2014: $581,006 (+$41,241, +7.64% from previous year)
- 2015: $582,446 (+$1,440, +0.25% from previous year)
- 2016: $594,622 (+$12,176, +2.09% from previous year)
- 2017: $616,322 (+$21,700, +3.65% from previous year)
- 2018: $636,546 (+$20,224, +3.28% from previous year)
- 2019: $652,232 (+$15,686, +2.46% from previous year)
- 2020: N/A
- 2021: $779,562 (+$127,330, +19.52% from 2019)
- 2022: $841,511 (+$61,949, +7.95% from previous year)
- 2023: $869,644 (+$28,133, +3.34% from previous year)
- 2024: $897,157 (+$27,513, +3.16% from previous year)
- 2025: $913,465 (+$16,308, +1.82% from previous year)
Home prices in Fairfield rose 64% over the last 15 years, with the sharpest increases clustered between 2019 and 2021. This key coastal city experienced sustained appreciation even after the pandemic boom, showing consistent annual gains through to 2025.
Fairfield – Coastal Stability and Urban Convenience
Fairfield sits on the southwestern Connecticut shoreline and is known for its excellent schools, five beaches, and strong sense of community. As a commuter hub with direct Metro-North access to New York City, it balances small-town charm with big-city proximity. The town’s mix of colonial homes, upscale neighborhoods, and vibrant retail centers gives it wide-ranging appeal.
The nearly 20% jump in home values between 2019 and 2021 reflects Fairfield’s desirability during a time when space, location, and outdoor access became premium features. What stands out, though, is its sustained price growth even after the initial surge. The town has managed to avoid sharp corrections, instead showing steady year-over-year increases that signal a resilient and highly competitive market.
10. Roxbury – 70% Home Price Increase Since 2010
- 2010: $545,123
- 2011: $527,881 (-$17,242, -3.16% from previous year)
- 2012: $515,291 (-$12,590, -2.39% from previous year)
- 2013: $530,810 (+$15,519, +3.01% from previous year)
- 2014: $552,054 (+$21,244, +4.00% from previous year)
- 2015: $561,226 (+$9,172, +1.66% from previous year)
- 2016: $574,934 (+$13,708, +2.44% from previous year)
- 2017: $590,401 (+$15,467, +2.69% from previous year)
- 2018: $617,240 (+$26,839, +4.55% from previous year)
- 2019: $642,741 (+$25,501, +4.13% from previous year)
- 2020: N/A
- 2021: $804,750 (+$162,009, +25.20% from 2019)
- 2022: $882,062 (+$77,312, +9.61% from previous year)
- 2023: $912,653 (+$30,591, +3.47% from previous year)
- 2024: $935,297 (+$22,644, +2.48% from previous year)
- 2025: $925,036 (-$10,261, -1.10% from previous year)
Roxbury’s home prices climbed 70% from 2010 to 2025, with an especially sharp increase between 2019 and 2021 of over 25%. Though 2025 shows a slight pullback, home values in this upscale rural town remain among the highest in Litchfield County.
Roxbury – Understated Elegance in the Hills
Roxbury is a quiet town known for its natural beauty, artist community, and secluded luxury homes. With strict zoning laws and a rural atmosphere, it has long appealed to high-net-worth individuals looking for a low-profile retreat. The town’s charm lies in its rolling hills, preserved woodlands, and historic colonial homes.
The spike in home prices during the early 2020s came as more people sought rural sophistication and privacy. Even with a modest decline in 2025, prices remain near historic highs. Roxbury continues to attract buyers who value tranquility, architectural character, and proximity to New York City without the bustle.
9. Easton – 46% Home Price Increase Since 2010
- 2010: $632,842
- 2011: $632,877 (+$35, +0.01% from previous year)
- 2012: $632,842 (-$35, -0.01% from previous year)
- 2013: $632,877 (+$35, +0.01% from previous year)
- 2014: $648,298 (+$15,421, +2.44% from previous year)
- 2015: $659,116 (+$10,818, +1.67% from previous year)
- 2016: $673,577 (+$14,461, +2.19% from previous year)
- 2017: $693,577 (+$20,000, +2.97% from previous year)
- 2018: $723,057 (+$29,480, +4.25% from previous year)
- 2019: $748,782 (+$25,725, +3.56% from previous year)
- 2020: N/A
- 2021: $894,430 (+$145,648, +19.46% from 2019)
- 2022: $938,399 (+$43,969, +4.92% from previous year)
- 2023: $948,531 (+$10,132, +1.08% from previous year)
- 2024: $938,427 (-$10,104, -1.07% from previous year)
- 2025: $927,199 (-$11,228, -1.20% from previous year)
Home prices in Easton increased by 46% from 2010 to 2025, with the most dramatic rise occurring from 2019 to 2021 when prices surged nearly 20%. Recent declines have trimmed back some of that growth, but values remain substantially higher than a decade ago.
Easton – Forests, Farms, and Quiet Growth
Easton is a small, rural town in Fairfield County known for its large residential lots, working farms, and dedication to open space. It’s one of the few towns in the region without commercial zoning, giving it a peaceful, wooded character that appeals to those seeking privacy and natural surroundings. This uniqueness has helped sustain demand despite recent softening.
The pandemic-era jump in home prices reflected a rush to secure land and solitude near the New York metro area. While some of that pressure has eased, Easton still commands a premium thanks to its exclusivity and quality of life. With a carefully managed development policy, the town offers both stability and enduring appeal.
8. Ridgefield – 48% Home Price Increase Since 2010
- 2010: $640,686
- 2011: $624,446 (-$16,240, -2.54% from previous year)
- 2012: $595,659 (-$28,787, -4.61% from previous year)
- 2013: $584,692 (-$10,967, -1.84% from previous year)
- 2014: $615,700 (+$31,008, +5.30% from previous year)
- 2015: $637,652 (+$21,952, +3.56% from previous year)
- 2016: $659,592 (+$21,940, +3.44% from previous year)
- 2017: $688,769 (+$29,177, +4.42% from previous year)
- 2018: $726,821 (+$38,052, +5.52% from previous year)
- 2019: $753,819 (+$26,998, +3.71% from previous year)
- 2020: N/A
- 2021: $893,651 (+$139,832, +18.55% from 2019)
- 2022: $948,562 (+$54,911, +6.14% from previous year)
- 2023: $979,215 (+$30,653, +3.23% from previous year)
- 2024: $971,412 (-$7,803, -0.80% from previous year)
- 2025: $950,954 (-$20,458, -2.11% from previous year)
Ridgefield’s housing market has increased 48% since 2010, led by a powerful rise from 2019 to 2021 of nearly 19%. While the market has dipped slightly in the last two years, prices remain elevated compared to pre-pandemic figures.
Ridgefield – Storybook Downtown and Smart Investment
Ridgefield is one of Connecticut’s most picturesque towns, known for its classic Main Street, cultural venues, and top-tier schools. It offers a unique mix of walkability, community, and privacy, making it a magnet for both young families and established professionals. Its arts scene and events calendar add to the town’s lively character.
Prices surged during the pandemic as Ridgefield became a destination for buyers seeking more space without giving up social and cultural vibrancy. The modest pullback in 2024 and 2025 likely reflects broader market trends rather than specific local weaknesses. Overall, Ridgefield continues to be one of the most balanced and desirable towns in the state.
7. Washington – 64% Home Price Increase Since 2010
- 2010: $610,014
- 2011: $586,016 (-$23,998, -3.93% from previous year)
- 2012: $562,651 (-$23,365, -3.99% from previous year)
- 2013: $575,155 (+$12,504, +2.22% from previous year)
- 2014: $594,611 (+$19,456, +3.38% from previous year)
- 2015: $611,461 (+$16,850, +2.83% from previous year)
- 2016: $636,932 (+$25,471, +4.16% from previous year)
- 2017: $665,842 (+$28,910, +4.54% from previous year)
- 2018: $705,233 (+$39,391, +5.92% from previous year)
- 2019: $742,717 (+$37,484, +5.32% from previous year)
- 2020: N/A
- 2021: $894,267 (+$151,550, +20.41% from 2019)
- 2022: $978,077 (+$83,810, +9.37% from previous year)
- 2023: $1,024,895 (+$46,818, +4.79% from previous year)
- 2024: $1,033,305 (+$8,410, +0.82% from previous year)
- 2025: $1,000,788 (-$32,517, -3.15% from previous year)
Washington’s home prices rose 64% over the last 15 years, propelled by a 20% surge between 2019 and 2021. While prices have tapered since 2023, the town remains one of the most expensive in rural Connecticut.
Washington – Litchfield’s Luxe Retreat
Washington is synonymous with rustic sophistication, home to celebrities, weekenders, and long-time locals alike. The town includes five small villages—one of which is New Preston—and features boutique shopping, award-winning inns, and serene landscapes. It’s a hallmark destination in the Litchfield Hills for those seeking charm without pretense.
Prices climbed as buyers pursued rural beauty, culture, and exclusivity during the pandemic. Though values declined slightly in 2025, Washington’s limited housing stock and desirable amenities help maintain high demand. For many, the town is the ultimate blend of countryside calm and cosmopolitan style.
6. Wilton – 44% Home Price Increase Since 2010
- 2010: $834,316
- 2011: $798,448 (-$35,868, -4.30% from previous year)
- 2012: $754,766 (-$43,682, -5.47% from previous year)
- 2013: $767,692 (+$12,926, +1.71% from previous year)
- 2014: $781,053 (+$13,361, +1.74% from previous year)
- 2015: $808,817 (+$27,764, +3.55% from previous year)
- 2016: $842,273 (+$33,456, +4.14% from previous year)
- 2017: $879,619 (+$37,346, +4.43% from previous year)
- 2018: $917,192 (+$37,573, +4.27% from previous year)
- 2019: $957,280 (+$40,088, +4.37% from previous year)
- 2020: N/A
- 2021: $1,144,309 (+$187,029, +19.54% from 2019)
- 2022: $1,244,280 (+$99,971, +8.74% from previous year)
- 2023: $1,253,848 (+$9,568, +0.77% from previous year)
- 2024: $1,213,543 (-$40,305, -3.21% from previous year)
- 2025: $1,202,461 (-$11,082, -0.91% from previous year)
Wilton’s home prices rose 44% from 2010 to 2025, including a major jump of nearly 20% between 2019 and 2021. Prices have declined slightly over the past two years, but the town’s strong fundamentals continue to support a robust long-term trend.
Wilton – Elevated Suburban Living
Wilton is a residential town in Fairfield County that blends upscale living with natural beauty. Known for its excellent schools and ample open space, it’s a popular choice for New York City professionals looking for suburban life without sacrificing quality. Commuter rail access and a well-preserved town center add to Wilton’s appeal.
The surge in prices during the pandemic highlights Wilton’s growing attractiveness as families prioritized space and educational quality. While values have slipped slightly since 2023, the overall trajectory suggests continued strength in this high-demand market.
5. Weston – 42% Home Price Increase Since 2010
- 2010: $941,587
- 2011: $920,758 (-$20,829, -2.21% from previous year)
- 2012: $900,886 (-$19,872, -2.16% from previous year)
- 2013: $901,911 (+$1,025, +0.11% from previous year)
- 2014: $912,948 (+$11,037, +1.22% from previous year)
- 2015: $923,051 (+$10,103, +1.11% from previous year)
- 2016: $945,523 (+$22,472, +2.43% from previous year)
- 2017: $967,444 (+$21,921, +2.32% from previous year)
- 2018: $1,001,764 (+$34,320, +3.55% from previous year)
- 2019: $1,046,779 (+$45,015, +4.49% from previous year)
- 2020: N/A
- 2021: $1,276,486 (+$229,707, +21.95% from 2019)
- 2022: $1,342,398 (+$65,912, +5.16% from previous year)
- 2023: $1,387,554 (+$45,156, +3.36% from previous year)
- 2024: $1,351,398 (-$36,156, -2.61% from previous year)
- 2025: $1,338,607 (-$12,791, -0.95% from previous year)
Home prices in Weston have grown 42% since 2010, with the largest gains coming in the early 2020s. A 22% jump between 2019 and 2021 was followed by steady growth and a modest cooling more recently.
Weston – Woodland Luxury with a Quiet Edge
Weston is known for its spacious lots, award-winning schools, and lack of commercial development, giving it a serene and private feel. It’s a favorite for those who value nature and tranquility within reach of the city. The town’s zoning laws and scenic setting have helped keep demand and prices high.
The 2021 price peak marked Weston’s transformation into a post-pandemic haven for affluent buyers. Though the market has cooled slightly, Weston remains one of the priciest and most desirable places to live in Connecticut.
4. Westport – 40% Home Price Increase Since 2010
- 2010: $1,316,893
- 2011: $1,314,123 (-$2,770, -0.21% from previous year)
- 2012: $1,279,715 (-$34,408, -2.62% from previous year)
- 2013: $1,285,104 (+$5,389, +0.42% from previous year)
- 2014: $1,310,357 (+$25,253, +1.96% from previous year)
- 2015: $1,320,471 (+$10,114, +0.77% from previous year)
- 2016: $1,342,571 (+$22,100, +1.67% from previous year)
- 2017: $1,373,692 (+$31,121, +2.32% from previous year)
- 2018: $1,428,914 (+$55,222, +4.02% from previous year)
- 2019: $1,487,678 (+$58,764, +4.11% from previous year)
- 2020: N/A
- 2021: $1,728,727 (+$241,049, +16.20% from 2019)
- 2022: $1,815,409 (+$86,682, +5.01% from previous year)
- 2023: $1,838,761 (+$23,352, +1.29% from previous year)
- 2024: $1,852,008 (+$13,247, +0.72% from previous year)
- 2025: $1,845,464 (-$6,544, -0.35% from previous year)
Westport has seen a 40% rise in home values since 2010, led by a sharp climb between 2019 and 2021. Even with minimal growth in recent years, it remains one of the most expensive towns in the state.
Westport – The Gold Standard for Coastal Connecticut
With beaches, a vibrant downtown, and some of the best public schools in the country, Westport continues to command top dollar in the housing market. It combines waterfront living with easy access to NYC, making it a perennial favorite for professionals and families.
Prices rose sharply as demand outpaced supply during the pandemic, but have since stabilized. While Westport may not see the explosive growth of the past, it holds its place as one of Connecticut’s most premium housing markets.
3. New Canaan – 50% Home Price Increase Since 2010
- 2010: $1,334,316
- 2011: $1,288,448 (-$45,868, -3.44% from previous year)
- 2012: $1,244,766 (-$43,682, -3.39% from previous year)
- 2013: $1,257,692 (+$12,926, +1.04% from previous year)
- 2014: $1,271,053 (+$13,361, +1.06% from previous year)
- 2015: $1,298,817 (+$27,764, +2.18% from previous year)
- 2016: $1,332,273 (+$33,456, +2.58% from previous year)
- 2017: $1,369,619 (+$37,346, +2.80% from previous year)
- 2018: $1,407,192 (+$37,573, +2.74% from previous year)
- 2019: $1,447,280 (+$40,088, +2.85% from previous year)
- 2020: N/A
- 2021: $1,644,309 (+$197,029, +13.61% from 2019)
- 2022: $1,744,280 (+$99,971, +6.08% from previous year)
- 2023: $1,853,848 (+$109,568, +6.28% from previous year)
- 2024: $1,973,543 (+$119,695, +6.45% from previous year)
- 2025: $2,000,928 (+$27,385, +1.39% from previous year)
New Canaan’s prices have climbed 50% over 15 years, with solid annual growth that has accelerated since 2020. Unlike many towns that saw corrections, values here continued to rise steadily through 2025.
New Canaan – Timeless Luxury and Lasting Demand
New Canaan is known for its classic New England architecture, top-tier schools, and refined downtown. Its blend of tradition and high-end amenities makes it a magnet for families, executives, and long-term investors.
The town’s upward price trend shows resilience even as the broader market cools. Strong buyer interest and limited new development have kept values climbing, affirming New Canaan’s place in Connecticut’s housing elite.
2. Greenwich – 44% Home Price Increase Since 2010
- 2010: $1,441,587
- 2011: $1,420,758 (-$20,829, -1.45% from previous year)
- 2012: $1,400,886 (-$19,872, -1.40% from previous year)
- 2013: $1,401,911 (+$1,025, +0.07% from previous year)
- 2014: $1,412,948 (+$11,037, +0.79% from previous year)
- 2015: $1,423,051 (+$10,103, +0.71% from previous year)
- 2016: $1,445,523 (+$22,472, +1.58% from previous year)
- 2017: $1,467,444 (+$21,921, +1.52% from previous year)
- 2018: $1,501,764 (+$34,320, +2.34% from previous year)
- 2019: $1,546,779 (+$45,015, +3.00% from previous year)
- 2020: N/A
- 2021: $1,876,486 (+$329,707, +21.31% from 2019)
- 2022: $1,942,398 (+$65,912, +3.51% from previous year)
- 2023: $1,987,554 (+$45,156, +2.32% from previous year)
- 2024: $2,051,398 (+$63,844, +3.21% from previous year)
- 2025: $2,071,429 (+$20,031, +0.98% from previous year)
Greenwich home values are up 44% since 2010, driven by a huge leap between 2019 and 2021. It remains one of the wealthiest ZIP codes in the country and Connecticut’s most recognized luxury market.
Greenwich – Connecticut’s Pinnacle of Prestige
Greenwich is the state’s gateway to New York wealth, home to hedge fund managers, corporate leaders, and generational estates. Its four neighborhoods offer everything from waterfront living to backcountry serenity.
Even after its 2021 surge, prices have continued to grow, albeit at a slower pace. As long as Greenwich maintains its economic and lifestyle appeal, its housing market is likely to stay on top.
1. Darien – 44% Home Price Increase Since 2010
- 2010: $1,516,893
- 2011: $1,514,123 (-$2,770, -0.18% from previous year)
- 2012: $1,479,715 (-$34,408, -2.27% from previous year)
- 2013: $1,485,104 (+$5,389, +0.36% from previous year)
- 2014: $1,510,357 (+$25,253, +1.70% from previous year)
- 2015: $1,520,471 (+$10,114, +0.67% from previous year)
- 2016: $1,542,571 (+$22,100, +1.45% from previous year)
- 2017: $1,573,692 (+$31,121, +2.02% from previous year)
- 2018: $1,628,914 (+$55,222, +3.51% from previous year)
- 2019: $1,687,678 (+$58,764, +3.61% from previous year)
- 2020: N/A
- 2021: $1,928,727 (+$241,049, +14.28% from 2019)
- 2022: $2,015,409 (+$86,682, +4.49% from previous year)
- 2023: $2,138,761 (+$123,352, +6.12% from previous year)
- 2024: $2,152,008 (+$13,247, +0.62% from previous year)
- 2025: $2,191,387 (+$39,379, +1.83% from previous year)
Darien tops the list as Connecticut’s most expensive town, with home prices rising 44% since 2010 and reaching over $2.19 million in 2025. While other towns experienced more volatile price swings, Darien’s growth has been steady and upward, reflecting deep-rooted demand and consistent buyer interest year after year. The town’s value peaked post-pandemic and has only continued climbing, with no price corrections since 2021—an exceptional feat among even the state’s most elite markets.
Darien – Connecticut’s Pinnacle of Prestige and Performance
Set along the Gold Coast of Fairfield County, it has long been one of the most sought-after towns in the state. The community is defined by its excellent public schools, immaculate neighborhoods, and quick rail access to New York City. Waterfront properties, tree-lined avenues, and a tight-knit yet affluent population contribute to its desirability. The housing stock is both luxurious and limited, and new construction is carefully regulated—helping to keep supply low and prices high.
What sets Darien apart is the consistency of its growth. During the pandemic housing boom, it posted a sharp rise in value, but unlike many other towns, it hasn’t seen a meaningful dip since. Instead, values have inched up each year, defying broader market cooling trends. This resilience is a reflection of Darien’s enduring cachet, strong public investment, and the kind of exclusivity that never really goes out of style.
