1,181

Old Hill Homes

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  • 21 Wright St, Westport, CT 06880
    21 Wright St, Westport, CT 06880
    21 Wright St, Westport, CT 06880
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    $995,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,507 Sq Ft

    21 Wright St, Westport, CT 06880

    Welcome to 21 Wright Street, Westport, CT - a charming blend of history and modern living. This classic mid-1800s home offers the allure of high ceilings and wide plank floors, exuding rustic elegance across its 1,507 square feet. Featuring three bedrooms and a rare primary suite with its own bath, this antique home provides both comfort and privacy. The living spaces are thoughtfully designed,

    Laurie Morris Compass Connecticut, LLC

    21 Wright St, Westport, CT 06880
  • 9 Woodside Ln, Westport, CT 06880

    $2,600,000 Sold Aug 15, 2025

    • 3,683 Sq Ft
    • $706/SF
    • 24 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1954

    9 Woodside Ln, Westport, CT 06880

    Welcome to this charming Colonial home in the desirable Old Hill neighborhood of Westport, CT. This 3,683 sq ft residence on a generous 0.95-acre lot blends classic character with modern convenience. The open layout connects living areas to the outdoors, creating an inviting space for relaxation and entertaining. The home boasts attractive exterior accents while maximizing space and inviting

    Judy Michaelis Coldwell Banker Realty

    9 Woodside Ln, Westport, CT 06880
  • 6 Weathervane Hill, Westport, CT 06880

    $2,591,000 Sold Aug 07, 2025

    • 4,771 Sq Ft
    • $543/SF
    • 29 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1949

    6 Weathervane Hill, Westport, CT 06880

    Welcome to 6 Weathervane Hill, a 4,196 sq ft sun-drenched home on over a private acre in a quiet cul-de-sac. Enjoy a versatile floor plan ideal for modern living. This classic colonial features a formal living and dining room, bright white kitchen, and cozy family room with a stone fireplace. The sunroom/playroom opens to a wraparound stone patio, Gunite pool. Upstairs are three spacious

    Amy van Arsdale Compass Connecticut, LLC

    6 Weathervane Hill, Westport, CT 06880
  • 52 Woodside Ave, Westport, CT 06880

    $1,850,000 Sold Jul 14, 2025

    • 2,891 Sq Ft
    • $640/SF
    • 8 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1965

    52 Woodside Ave, Westport, CT 06880

    Enjoy a wonderful life on Woodside Avenue, one of Old Hill's most popular streets, walking distance to town & Earthplace Nature Centre. This charming ranch home offers sophisticated, easy living & so much more. The open floorplan radiates off the bright kitchen with stainless steel appliances, including a wine fridge & gorgeous granite countertops. The formal living room enjoys a wall of sliding

    Jessica Brookbanks Coldwell Banker Realty

    52 Woodside Ave, Westport, CT 06880
  • 75 Old Hill Rd, Westport, CT 06880

    $2,225,000 Sold Jul 07, 2025

    • 3,585 Sq Ft
    • $621/SF
    • 23 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1993

    75 Old Hill Rd, Westport, CT 06880

    Stunning colonial with contemporary flair set on a private acre in much sought after Old Hill. Convenient to town, train and beach. This is not your cookie cutter colonial with wonderful, flexible, open floor plan and top of the line remodeled kitchen. Current piano room could be formal dining room or office/study. Impressive Primary Bedroom suite with beautiful bath. Large upstairs room with

    Regina Kendig William Raveis Real Estate

    75 Old Hill Rd, Westport, CT 06880
  • 30 Hills Ln Unit 30, Westport, CT 06880

    $450,500 Sold Jun 27, 2025

    • 1,200 Sq Ft
    • $375/SF
    • 5 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1973

    30 Hills Ln Unit 30, Westport, CT 06880

    Welcome home to Birchwood! This beautifully maintained community offers a tranquil escape from city life. Tucked away, yet minutes to all Norwalk/Westport attractions. Here you will find meticulous landscaping, community club house and an in-ground pool, setting the stage for a super summer retreat. This wonderful 2 bedrooms, 1.5 bath condo offers a rare two car garage with two storage bay areas,

    Aurelia Gilbert Coldwell Banker Realty

    30 Hills Ln Unit 30, Westport, CT 06880
  • 19 Old Hill Farms Rd, Westport, CT 06880
    19 Old Hill Farms Rd, Westport, CT 06880
    19 Old Hill Farms Rd, Westport, CT 06880
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    $6,250,000 Sold Jun 20, 2025

    • 7,595 Sq Ft
    • $823/SF
    • 2 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 2012

    19 Old Hill Farms Rd, Westport, CT 06880

    Better than new! This impeccably designed home, built by Coastal Home Builders, is nestled on a coveted street in the desirable Old Hill section of Westport. Recent upgrades have further enhanced this already exceptional property. From the moment you enter the grand foyer, you'll be greeted by luxurious interiors and a seamless floor plan ideal for both everyday living and entertaining. French

    Jennifer Leahy Compass Connecticut, LLC

    19 Old Hill Farms Rd, Westport, CT 06880
  • 10 Heathwood Ln, Westport, CT 06880

    $2,290,000 Sold Jun 17, 2025

    • 4,000 Sq Ft
    • $572/SF
    • 13 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 2020

    10 Heathwood Ln, Westport, CT 06880

    Nestled on a private street in the sought-after Old Hill neighborhood, this contemporary/colonial style home provides the perfect blend of picturesque tranquility and convenience. The home is in pristine condition and is tastefully decorated featuring modern finishes, designer lighting and an overall inviting ambiance. Sunshine flows through the energy-efficient glass windows as you feel the

    Lauren Turner Corcoran Centric Realty

    10 Heathwood Ln, Westport, CT 06880
  • 97 Partrick Rd, Westport, CT 06880

    $1,068,900 Sold Jun 16, 2025

    • 2,030 Sq Ft
    • $527/SF
    • 18 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1969

    97 Partrick Rd, Westport, CT 06880

    HIGHEST & BEST by SUNDAY APRIL 13th at 5:00 pm. Find your private Shangri-La, with in-ground pool, set back from the road on 1.35 acres in prestigious Old Hill. The custom Split was built by the original owners and is on the market for the first time. Entering from the front porch you are greeted by the welcoming entry hall with slate floor. Hand-pegged wide Antique hardwood floors are found in

    Mindy Wolkstein William Raveis Real Estate

    97 Partrick Rd, Westport, CT 06880
  • 27 Old Hill Farms Rd, Westport, CT 06880

    $3,250,000 Sold Jun 06, 2025

    • 4,298 Sq Ft
    • $756/SF
    • 8 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1931

    27 Old Hill Farms Rd, Westport, CT 06880

    Classic "Old Hill Farms" Estate. One of a kind custom home completely renovated and restored to perfection. Showcase sun filled home with a marriage of old and new. Exceptional details, all custom millwork and cabinetry set on over one acre in premier Old Hill location. Gracious formal living room with custom built in window seat.Original wood burning fireplace complete this large gathering room

    Debra Grant Show to Sell Homes, LLC

    27 Old Hill Farms Rd, Westport, CT 06880
  • 115 Wilton Rd, Westport, CT 06880

    $955,000 Sold Apr 18, 2025

    • 2,065 Sq Ft
    • $462/SF
    • 54 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1886

    115 Wilton Rd, Westport, CT 06880

    RARE OPPORTUNITY to own in Westport with income to support your family. This multi-family home is just across the street from scenic Saugatuck River and convenient to Westport center. Remodeled features include updated kitchens, bathrooms, windows, mechanicals & more. UNIT #1 is on 1st floor: Living Rm, Eat-in Kitchen, 2 Bedrooms, Full Bathroom with laundry, Screened Porch. UNIT #2: 2nd floor:

    Lynn Fraund William Pitt Sotheby's Int'l

    115 Wilton Rd, Westport, CT 06880
  • 2 Twin Falls Ln, Westport, CT 06880

    $3,450,000 Sold Apr 15, 2025

    • 6,789 Sq Ft
    • $508/SF
    • 4 Days On Market
    • 5 Beds
    • 6.5 Baths
    • Built 2002

    2 Twin Falls Ln, Westport, CT 06880

    A circular drive welcomes you as you approach this grand Center Hall Colonial, on 2 scenic acres with a fantastic Har-Tru tennis court, pool site & beautiful perennial gardens, sited on a quiet private lane in central Westport. Timeless elegance & quality construction is evident, from the moment you step into the impressive Entry Hall of this masterfully crafted home. Be delighted by the 10'

    Laurie Crouse Coldwell Banker Realty

    2 Twin Falls Ln, Westport, CT 06880
  • 219 Wilton Rd, Westport, CT 06880

    $1,098,000 Sold Mar 31, 2025

    • 1,908 Sq Ft
    • $575/SF
    • 38 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1973

    219 Wilton Rd, Westport, CT 06880

    Nestled in the heart of Westport this unique contemporary sits high on a 1-acre lot. Bright & airy w/high ceilings, multiple windows, French doors, and skylights this home is bathed in natural light. An inviting covered entrance w/large glass paneled doors welcomes you. From the entrance hall take the stairs to the heart-of-the-home, an open great-room w/hardwood flr, grand fireplace, vaulted

    Sandra Kinseley William Raveis Real Estate

    219 Wilton Rd, Westport, CT 06880
  • 7 Hills Ln, Westport, CT 06880

    $555,000 Sold Mar 20, 2025

    • 1,639 Sq Ft
    • $339/SF
    • 24 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1973

    7 Hills Ln, Westport, CT 06880

    Nestled in the sought-after Birchwood complex, this spacious three-bedroom, two-bath condo offers comfort and convenience.This one-level living unit features beautiful hardwood floors and a desirable open floor plan.The welcoming foyer leads to a living room with a wood-burning fireplace, seamlessly flowing into the dining area and private balcony, perfect for relaxing or entertaining.The

    Maria Tziolis William Pitt Sotheby's Int'l

    7 Hills Ln, Westport, CT 06880
  • 52 Hills Ln, Westport, CT 06880

    $410,000 Sold Mar 14, 2025

    • 1,386 Sq Ft
    • $296/SF
    • 51 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1973

    52 Hills Ln, Westport, CT 06880

    Welcome to the desirable Birchwood complex located on the Westport line. Spacious and bright ranch-style unit with just under 1400 sqft of living space, carport and private storage. Complex is secluded and well maintained with beautiful landscaping, in-ground pool and clubhouse. Unit features three bedrooms and two full baths. Primary bedroom w/ full bath, living room with sliders to deck &

    Jennifer Capozziello Coldwell Banker Realty

    52 Hills Ln, Westport, CT 06880
  • 56 Wright St, Westport, CT 06880

    $1,643,000 Sold Feb 28, 2025

    • 3,450 Sq Ft
    • $476/SF
    • 125 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1912

    56 Wright St, Westport, CT 06880

    Welcome to a truly enchanting opportunity nestled in the coveted Old Hill neighborhood of Westport, CT.Some special features of this 1912 home that help tell its story of a bygone era are the sun drenched loft -like Great Room with it's enormous window offering northern light exposure. It was an artist's studio in the past.This magical space is divided into many living areas & has infinite

    Jillian Klaff Coldwell Banker Realty

    56 Wright St, Westport, CT 06880
  • 60 Wilton Rd, Westport, CT 06880

    $2,925,000 Sold Feb 21, 2025

    • 2,517 Sq Ft
    • $1,162/SF
    • 102 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2023

    60 Wilton Rd, Westport, CT 06880

    Welcome to Bankside House in vibrant downtown Westport. Unit never lived in and staged to perfection! This unit is the largest 2Bedroom in building, southwest corner exposure with two outside terraces one plumbled for an outdoor kitchen and engineered hot tub. Saugatuck River views from primary bedroom and dining room. The fantistic open floor plans allows sun light galory. Custom built-ins

    Robert DiDonato William Raveis Real Estate

    60 Wilton Rd, Westport, CT 06880
  • 60 Wilton Rd Unit 2B, Westport, CT 06880
    60 Wilton Rd Unit 2B, Westport, CT 06880
    60 Wilton Rd Unit 2B, Westport, CT 06880
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    $2,925,000 Sold Feb 21, 2025

    • 2,517 Sq Ft
    • $1,162/SF
    • 101 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2023

    60 Wilton Rd Unit 2B, Westport, CT 06880

    AO No more show Jan 30thWelcome to Bankside House in vibrant downtown Westport. Unit never lived in and staged to perfection! This unit is the largest 2Bedroom in building, southwest corner exposure with two outside terraces one plumbled for an outdoor kitchen and engineered hot tub. Saugatuck River views from primary bedroom and dining room. The fantistic open floor plans allows sun

    Robert DiDonato William Raveis Real Estate

    60 Wilton Rd Unit 2B, Westport, CT 06880
  • 10 Bolton Ln, Westport, CT 06880

    $4,525,000 Sold Jan 24, 2025

    • 7,754 Sq Ft
    • $584/SF
    • 27 Days On Market
    • 6 Beds
    • 8 Baths
    • Built 2023

    10 Bolton Ln, Westport, CT 06880

    Experience the epitome of modern luxury in this extraordinary 6-bedroom, 6/2 bath 7700+ sf new construction waterfront home with a pool and a dock. Built by Bear Paw Construction and designed by Don Fairbanks, this stunning light-filled home is finished on 4 levels. With meticulous attention to detail and a sleek, contemporary design, this home sets a new standard for sophistication.

    Susan Lieberman The Riverside Realty Group

    10 Bolton Ln, Westport, CT 06880
  • 5 White Woods Ln, Westport, CT 06880

    $2,200,000 Sold Jan 22, 2025

    • 4,068 Sq Ft
    • $541/SF
    • 12 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1976

    5 White Woods Ln, Westport, CT 06880

    Nestled on a serene cul-de-sac in the sought-after Old Hill neighborhood, this exquisite 5-bedroom, 4.1-bath home sits on 1.4 acres of beautifully lush, mature landscaping. Ideally located, you're just minutes from town, schools, the train, beaches, Earthplace, and the YMCA, blending convenience with tranquility. Stepping into the heart of this home is a bright, modern kitchen and breakfast

    Beth Saunders Berkshire Hathaway NE Prop.

    5 White Woods Ln, Westport, CT 06880
  • 6 Hilly Field Ln, Westport, CT 06880

    $2,150,000 Sold Jan 02, 2025

    • 2,950 Sq Ft
    • $729/SF
    • 22 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1965

    6 Hilly Field Ln, Westport, CT 06880

    Welcome to the most charming and delightful home in Old Hill! Beautiful 6 Hilly Field Lane has been lovingly renovated & is waiting for you. Set on a peaceful cul-de-sac that's perfect for any walk, bike or ride. Less than 6 minutes to downtown Westport and the train and Less than 10 minutes to Compo beach- you'll have easy access to everything. The spacious, flat backyard features a stunning

    Kit Tingley Higgins Group Bedford Square

    6 Hilly Field Ln, Westport, CT 06880

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