Darien, CT Homes

• 

  

  /2

  Est $2,949,609

  Not Listed For Sale

  5 Plymouth Rd, Darien, CT 06820

  • 4 Beds
  • 3 Baths
  • 2,622 Sq Ft
  • Built 1995

  5 Plymouth Rd, Darien, CT 06820

  Last Sold Summary

  • 20% Below List Price
  • $936/SF

  • Last Sold Price $2,455,000

  Last Listing Agent Sheree Frank Houlihan Lawrence
• 

  

  

  /39

  $8,995,000

  • 9 Beds
  • 10 Baths
  • 8,188 Sq Ft

  16 East Trail, Darien, CT 06820

  Set within the coveted Tokeneke Association, 16 East Trail is a rare legacy property where architectural pedigree meets modern luxury. Originally built in 1908 as one of the enclave's earliest residences, the home reflects the timeless elegance of McKim, Mead & White and Delano & Aldrich-thoughtfully reimagined for today's living. A masterful renovation by architect Peter Pennoyer preserves the

  Ashley Dineen Compass Connecticut, LLC

  16 East Trail, Darien, CT 06820
• 

  $980,000

  Sold Dec 15, 2025

  10 Pine Brook Ln, Darien, CT 06820

  • 2 Beds
  • 2 Baths
  • 1,278 Sq Ft
  • Built 1987

  Last Sold Summary

  • 4% Above List Price
  • $767/SF
  • 52 Days On Market

  Current Estimated Value $997,019

  Last Listing Agent Sara Hesli Houlihan Lawrence

  10 Pine Brook Ln, Darien, CT 06820
• 

  

  /2

  Est $4,050,026

  Not Listed For Sale

  16 Plymouth Rd, Darien, CT 06820

  • 5 Beds
  • 5 Baths
  • 4,690 Sq Ft
  • Built 1953

  16 Plymouth Rd, Darien, CT 06820

  Last Sold Summary

  • 13% Below List Price
  • $768/SF

  • Last Sold Price $3,600,000

  Last Listing Agent Nellie Snell William Raveis Real Estate
• 

  

  

  /40

  $4,295,000

  Pending

  • 6 Beds
  • 5.5 Baths
  • 5,505 Sq Ft

  8 Pasture Ln, Darien, CT 06820

  Welcome to 8 Pasture Lane, a property that redefines FUN in luxury living with resort-style elegance in one of Darien's most desirable locations. This stunning 6-bedroom, 5,500 sq. ft. home offers impeccable design, thoughtful architecture & an extraordinary flow that's as unique and functional as it is beautiful. From the moment you step inside, the first floor sets the tone for a home that's

  Keiley Fuller Compass Connecticut, LLC

  8 Pasture Ln, Darien, CT 06820
• 

  $26,500,000

  Sold Nov 14, 2025

  0 Hay Island Unit 24078034, Darien, CT 06820

  • 6 Beds
  • 7.5 Baths
  • 8,684 Sq Ft
  • Built 2010

  Last Sold Summary

  • 24% Below List Price
  • $3,052/SF
  • 244 Days On Market

  Last Listing Agent Leslie McElwreath Sotheby's International Realty

  0 Hay Island Unit 24078034, Darien, CT 06820
• 

  /2

  Est $3,597,016

  Not Listed For Sale

  10 Plymouth Rd, Darien, CT 06820

  • 3 Beds
  • 4 Baths
  • 3,386 Sq Ft
  • Built 1994

  10 Plymouth Rd, Darien, CT 06820

  Last Sold Summary

  • 15% Below List Price
  • $923/SF

  • Last Sold Price $3,125,000

  Last Listing Agent Angela Swift Compass Connecticut, LLC
• 

  

  /4

  $2,525,000

  • 8 Beds
  • 3 Baths
  • 3,443 Sq Ft

  2646 Boston Post Rd, Darien, CT 06820

  Home with seasonal water views of Holly Pond. Present use: Boarding House. Sold "As Is".

  Angela Abate William Raveis Real Estate

  2646 Boston Post Rd, Darien, CT 06820
• 

  $2,710,000

  Sold Dec 08, 2025

  23 Maplewood Dr, Darien, CT 06820

  • 5 Beds
  • 3.5 Baths
  • 3,506 Sq Ft
  • Built 1969

  Last Sold Summary

  • 8% Above List Price
  • $773/SF
  • 20 Days On Market

  Current Estimated Value $2,805,725

  Last Listing Agent Meredith Derosa William Pitt Sotheby's Int'l

  23 Maplewood Dr, Darien, CT 06820
• 

  Est $3,785,946

  Not Listed For Sale

  16 Mayflower Rd, Darien, CT 06820

  • 5 Beds
  • 3.5 Baths
  • 3,431 Sq Ft
  • Built 1952

  16 Mayflower Rd, Darien, CT 06820

  Last Sold Summary

  • 11% Above List Price
  • $991/SF
  • 12 Days On Market

  • Last Sold Price $3,400,521
  • Aug 15, 2023

  Last Listing Agent Tamie Thomas Houlihan Lawrence
• 

  

  /34

  $2,475,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 2,750 Sq Ft

  12 Libby Ln, Darien, CT 06820

  Modern ranch perfection in one of Darien's most sought after neighborhoods. This exceptional home was stripped down to the studs and completely rebuilt, offering the rare combination of one-level living with the style and confidence of a near-new construction renovation. Thoughtfully re-imagined with clean and modern finishes and an easy, open flow, this home is designed for today's lifestyle-

  Pam Pokorny Compass Connecticut, LLC

  12 Libby Ln, Darien, CT 06820
• 

  $3,000,000

  Sold Mar 02, 2026

  109 Stephen Mather Rd, Darien, CT 06820

  • 5 Beds
  • 3.5 Baths
  • 4,817 Sq Ft
  • Built 1971

  Last Sold Summary

  • 9% Below List Price
  • $623/SF
  • 114 Days On Market

  Current Estimated Value $3,045,752

  Last Listing Agent Suzanne Okie Brown Harris Stevens

  109 Stephen Mather Rd, Darien, CT 06820
• 

  /2

  Est $3,011,781

  Not Listed For Sale

  6 Mayflower Rd, Darien, CT 06820

  • 4 Beds
  • 4 Baths
  • 2,855 Sq Ft
  • Built 1953

  6 Mayflower Rd, Darien, CT 06820

  Last Sold Summary

  • 21% Below List Price
  • $874/SF

  • Last Sold Price $2,495,000

  Last Listing Agent Deborah Hidy Houlihan Lawrence
• 

  

  /40

  $7,900,000

  • 7 Beds
  • 9 Baths
  • 8,100 Sq Ft

  246 Brookside Rd, Darien, CT 06820

  Introducing a one-of-a-kind gem in Darien: the historic Eliaseph Whitney House, originally built in 1770, nestled on an expansive 4.12-acre parcel- one of the largest of its kind in town. This iconic property effortlessly blends centuries-old charm with modern-day functionality. Step inside to discover timeless details like wood-beamed ceilings and floors, multiple fireplaces, a cozy den and

  Keiley Fuller Compass Connecticut, LLC

  246 Brookside Rd, Darien, CT 06820
• 

  $3,000,500

  Sold Jun 05, 2025

  15 Gardiner St, Darien, CT 06820

  • 7 Beds
  • 6 Baths
  • 5,722 Sq Ft
  • Built 2016

  Last Sold Summary

  • 6% Below List Price
  • $524/SF
  • 17 Days On Market

  Current Estimated Value $3,256,472

  Last Listing Agent Kathryn Bates Compass Connecticut, LLC

  15 Gardiner St, Darien, CT 06820
• 

  

  /47

  Est $4,571,011

  Not Listed For Sale

  15 Waverly Rd, Darien, CT 06820

  • 5 Beds
  • 7 Baths
  • 4,301 Sq Ft
  • Built 2021

  15 Waverly Rd, Darien, CT 06820

  Last Sold Summary

  • 11% Above List Price
  • $959/SF
  • 36 Days On Market

  • Last Sold Price $4,125,000
  • Jul 31, 2023

  Last Listing Agent Holly Hawes Compass Connecticut, LLC
• 

  

  /30

  $1,680,000

  Open Sun 1PM - 3PM

  • 4 Beds
  • 2 Baths
  • 2,563 Sq Ft

  150 Holmes Ave, Darien, CT 06820

  Step into timeless elegance at 150 Holmes Avenue in Darien. This sunlit Victorian home effortlessly blends classic charm with modern convenience, offering a warm and inviting space for living, entertaining, and making memories. With 4 spacious bedrooms and 2 full baths, there's plenty of room to grow, host, or simply enjoy the good life. Inside, high ceilings and an abundance of natural light

  Keiley Fuller Compass Connecticut, LLC

  150 Holmes Ave, Darien, CT 06820
• 

  $3,650,000

  Sold Aug 20, 2025

  326 Hollow Tree Ridge Rd, Darien, CT 06820

  • 5 Beds
  • 4.5 Baths
  • 6,860 Sq Ft
  • Built 1993

  Last Sold Summary

  • 16% Above List Price
  • $532/SF
  • 11 Days On Market

  Current Estimated Value $3,656,345

  Last Listing Agent Nancy Peter Houlihan Lawrence

  326 Hollow Tree Ridge Rd, Darien, CT 06820
• 

  

  /37

  Est $8,066,428

  Not Listed For Sale

  11 Pratt Island, Darien, CT 06820

  • 5 Beds
  • 8 Baths
  • 8,804 Sq Ft
  • Built 2007

  11 Pratt Island, Darien, CT 06820

  Last Sold Summary

  • 23% Below List Price
  • $1,193/SF
  • 163 Days On Market

  • Last Sold Price $10,500,000
  • Jun 14, 2024

  Last Listing Agent Jennifer Leahy Compass Connecticut, LLC
• 

  

  /32

  $2,395,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 3,384 Sq Ft

  27 Point o Woods Rd S, Darien, CT 06820

  Tucked away on a quiet cul-de-sac in the sought after Ox-Ridge school district, this beautifully updated 4 Bedroom, 2.5 Bath Colonial offers an exceptional blend of timeless elegance and modern sophistication. Thoughtfully designed for both refined living and effortless entertaining, the home features a stunning renovated kitchen and spa inspired baths, all finished with quality craftsmanship and

  Caroline Hanley Houlihan Lawrence

  27 Point o Woods Rd S, Darien, CT 06820
• 

  $3,815,139

  Sold May 21, 2025

  25 Gardiner St, Darien, CT 06820

  • 6 Beds
  • 4.5 Baths
  • 5,950 Sq Ft
  • Built 2017

  Last Sold Summary

  • 12% Above List Price
  • $641/SF
  • 6 Days On Market

  Current Estimated Value $4,016,914

  Last Listing Agent Nellie Snell William Raveis Real Estate

  25 Gardiner St, Darien, CT 06820
• 

  /2

  Est $5,668,935

  Not Listed For Sale

  2 Baywater Dr, Darien, CT 06820

  • 5 Beds
  • 6 Baths
  • 5,124 Sq Ft
  • Built 2012

  2 Baywater Dr, Darien, CT 06820

  Last Sold Summary

  • 28% Below List Price
  • $864/SF

  • Last Sold Price $4,425,000

  Last Listing Agent Catherine Russell Brown Harris Stevens
• 

  

  /33

  $2,700,000

  • 4 Beds
  • 3 Baths
  • 2,796 Sq Ft

  8 Seagate Rd, Darien, CT 06820

  Waterviews!! Welcome to 8 Seagate Road, a rare opportunity to live in one of Darien's most sought after waterfront communities! Enjoy views of Holly Pond from this custom-built home, offering a terrific layout. The large living room offers built-in cabinetry, a cozy fireplace & leads to the formal dining room, both with beautiful water views! The bright kitchen is nicely sized, with quartz

  Kevin Quick William Pitt Sotheby's Int'l

  8 Seagate Rd, Darien, CT 06820
• 

  $3,725,000

  Sold Aug 01, 2025

  2 Dogwood Ln, Darien, CT 06820

  • 5 Beds
  • 3.5 Baths
  • 5,265 Sq Ft
  • Built 1959

  Last Sold Summary

  • 8% Above List Price
  • $708/SF
  • 5 Days On Market

  Current Estimated Value $3,856,809

  Last Listing Agent Keiley Fuller Compass Connecticut, LLC

  2 Dogwood Ln, Darien, CT 06820
• 

  Est $1,054,631

  Not Listed For Sale

  18 Catalpa Terrace, Darien, CT 06820

  • 3 Beds
  • 1 Bath
  • 1,102 Sq Ft
  • Built 1936

  18 Catalpa Terrace, Darien, CT 06820

  Last Sold Summary

  • 15% Above List Price
  • $832/SF
  • 7 Days On Market

  • Last Sold Price $917,096
  • Dec 10, 2024

  Last Listing Agent COURTNEY HAIDINGER Houlihan Lawrence
• 

  

  /31

  $1,395,000

  Pending

  • 2 Beds
  • 1.5 Baths
  • 1,292 Sq Ft

  25 Lakeside Ave, Darien, CT 06820

  A Rare Opportunity to live on the Coveted Tilley Pond Park with Sweeping Park & Water views. Beautifully designed for effortless living & entertaining, offering a rare blend of natural beauty, walkability, & coastal town charm. On the Pond - where mornings begin with coffee, peaceful water views and evenings end with sunsets reflecting off the park. Stroll along an idyllic street to downtown

  Kathryn Bates Compass Connecticut, LLC

  25 Lakeside Ave, Darien, CT 06820
• 

  $3,625,000

  Sold Jun 24, 2025

  9 Beach Dr, Darien, CT 06820

  • 5 Beds
  • 3.5 Baths
  • 4,223 Sq Ft
  • Built 1924

  Last Sold Summary

  • 21% Above List Price
  • $858/SF
  • 7 Days On Market

  Current Estimated Value $3,804,763

  Last Listing Agent Nellie Snell William Raveis Real Estate

  9 Beach Dr, Darien, CT 06820
• 

  /2

  Est $1,166,475

  Not Listed For Sale

  4 Oakland Terrace, Darien, CT 06820

  • 4 Beds
  • 2 Baths
  • 1,428 Sq Ft
  • Built 1921

  4 Oakland Terrace, Darien, CT 06820

  Last Sold Summary

  • 6% Below List Price
  • $770/SF

  • Last Sold Price $1,100,000

  Last Listing Agent Lucille Story Brown Harris Stevens
• 

  

  /36

  $8,500,000

  $850K PRICE DROP

  • 7 Beds
  • 10 Baths
  • 9,649 Sq Ft

  18 Tokeneke Trail, Darien, CT 06820

  This magnificent Round Meadows estate with a fantastic 9700 sf house on 5.346 acres of private property is now on the market for the first time in more than 54 years. Located in the private Tokeneke Association with protected land trust property to the East and West of it, Round Meadows is the ultimate in privacy and natural beauty. The owners had the vision to preserve, restore and ultimately

  Robin Stineman William Pitt Sotheby's Int'l

  18 Tokeneke Trail, Darien, CT 06820
• 

  $755,000

  Sold Jun 20, 2025

  33 Hale Ln, Darien, CT 06820

  • 1 Bed
  • 1.5 Baths
  • 900 Sq Ft
  • Built 1987

  Last Sold Summary

  • 10% Above List Price
  • $839/SF
  • 47 Days On Market

  Current Estimated Value $789,921

  Last Listing Agent Robin Halsey Compass Connecticut, LLC

  33 Hale Ln, Darien, CT 06820
• 

  Est $846,769

  Not Listed For Sale

  15 Catalpa Terrace, Darien, CT 06820

  • 3 Beds
  • 1 Bath
  • 941 Sq Ft
  • Built 1926

  15 Catalpa Terrace, Darien, CT 06820

  Last Sold Summary

  • 35% Above List Price
  • $664/SF
  • 23 Days On Market

  • Last Sold Price $625,000
  • Nov 28, 2023

  Last Listing Agent Monica Osorio Realty ONE Group Connect
• 

  /2

  $800,000

  Under Contract

  • Land
  • 7,405 Sq Ft
  • $4,705,882 per Acre

  166 Hollow Tree Ridge Rd, Darien, CT 06820

  Ideal location for your dream house. Level, open building lot close to the brand new Heights Crossing and Darien Commons with new shops and restaurants. Train into NYC is minutes away. Darien has award winning schools, two town beaches, easy commute, and the world class Great Island Nature Park. Darien is where you want to be. Don't miss this golden opportunity. There are two adjacent building

  Gunnar Edelstein BHHS Darien/New Canaan

  166 Hollow Tree Ridge Rd, Darien, CT 06820
• 

  $4,500,000

  Sold Aug 12, 2025

  1 Fox Hill Ln, Darien, CT 06820

  • 4 Beds
  • 6 Baths
  • 5,561 Sq Ft
  • Built 1998

  Last Sold Summary

  • 5% Above List Price
  • $809/SF
  • 6 Days On Market

  Current Estimated Value $4,531,815

  Last Listing Agent Janine Tienken Houlihan Lawrence

  1 Fox Hill Ln, Darien, CT 06820
• 

  Est $2,714,014

  Not Listed For Sale

  5 Weeds Landing, Darien, CT 06820

  • 4 Beds
  • 2.5 Baths
  • 3,880 Sq Ft
  • Built 1979

  5 Weeds Landing, Darien, CT 06820

  Last Sold Summary

  • 17% Above List Price
  • $597/SF
  • 7 Days On Market

  • Last Sold Price $2,315,000
  • Jun 26, 2023

  Last Listing Agent Karen Bonner Houlihan Lawrence
• 

  

  /31

  $1,995,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,760 Sq Ft

  217 Mansfield Ave, Darien, CT 06820

  217 Mansfield Avenue presents a rare opportunity to secure a full, flat acre in one of North Darien's most desirable and rapidly evolving neighborhoods. Set on beautiful, level land, the property currently features a charming but dated Cape Cod-style home ready for its next chapter. Buyers may choose to renovate and restore the existing residence, bringing new life to its classic bones, or take

  Peter Stuart Houlihan Lawrence

  217 Mansfield Ave, Darien, CT 06820
• 

  $2,250,000

  Sold Sep 29, 2025

  27 Kensett Ln Unit 27, Darien, CT 06820

  • 3 Beds
  • 4.5 Baths
  • 4,068 Sq Ft
  • Built 2014

  Last Sold Summary

  • 18% Above List Price
  • $553/SF
  • 5 Days On Market

  Last Listing Agent Luke Broughton Compass Connecticut, LLC

  27 Kensett Ln Unit 27, Darien, CT 06820
• 

  Est $3,014,258

  Not Listed For Sale

  6 Weeds Landing, Darien, CT 06820

  • 4 Beds
  • 4.5 Baths
  • 4,863 Sq Ft
  • Built 1977

  6 Weeds Landing, Darien, CT 06820

  Last Sold Summary

  • 21% Above List Price
  • $514/SF
  • 15 Days On Market

  • Last Sold Price $2,500,000
  • Jul 17, 2024

  Last Listing Agent Sara Littlefield Berkshire Hathaway Home Services
• 

  

  /38

  $8,890,000

  New Construction Coming Soon

  • 5 Beds
  • 7.5 Baths
  • 9,396 Sq Ft

  45 Old Farm Rd, Darien, CT 06820

  Privately set within Darien's coveted Tokeneke neighborhood, 45 Old Farm is a remarkable custom estate by award-winning builder Oliver Wilson. A tree-lined drive framed by natural stone pillars sets the tone for this exceptional property. Inside, every room is thoughtfully composed with striking sight lines and abundant natural light. The chef's kitchen is a true centerpiece, anchored by a

  Amanda Spatola Houlihan Lawrence

  45 Old Farm Rd, Darien, CT 06820
• 

  $2,050,000

  Sold Dec 30, 2025

  72 Kensett Ln, Darien, CT 06820

  • 3 Beds
  • 3.5 Baths
  • 4,067 Sq Ft
  • Built 2017

  Last Sold Summary

  • 3% Above List Price
  • $504/SF
  • 19 Days On Market

  Current Estimated Value $2,088,469

  Last Listing Agent Pam Pokorny Compass Connecticut, LLC

  72 Kensett Ln, Darien, CT 06820
• 

  /2

  Est $3,766,742

  Not Listed For Sale

  2 Seagate Rd, Darien, CT 06820

  • 5 Beds
  • 8 Baths
  • 5,183 Sq Ft
  • Built 2007

  2 Seagate Rd, Darien, CT 06820

  Last Sold Summary

  • 28% Below List Price
  • $569/SF

  • Last Sold Price $2,950,000

  Last Listing Agent Nancy Peter Houlihan Lawrence

Showing Results 161 - 200, Page 5 of 18