1,183

Old Hill Homes

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  • 6 Edge Hill Trail, Westport, CT 06880

    $1,085,000 Sold Aug 29, 2024

    • 2,368 Sq Ft
    • $458/SF
    • 63 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1964

    6 Edge Hill Trail, Westport, CT 06880

    WALK TO TOWN from this private, tucked away Old Hill location. Secluded yet near the heart of Westport with River & City seasonal views and stunning sunsets. Great opportunity to move in this summer, renovate or build new. Well maintained 4BR/3BA oversized Cape Cod style home with 1st floor Primary Bedroom/Bath, Family room/fp, LR, Kitchen/Dining area, lower level playroom, gym, or office area.

    Nancy Hatfield Coldwell Banker Realty

    6 Edge Hill Trail, Westport, CT 06880
  • 2 Broadview Rd, Westport, CT 06880

    $4,700,000 Sold Aug 26, 2024

    • 13,203 Sq Ft
    • $356/SF
    • 295 Days On Market
    • 6 Beds
    • 8.5 Baths
    • Built 2005

    2 Broadview Rd, Westport, CT 06880

    60-mins from NYC! Set amid acres of matured specimen plantings, this New England shingle style home is a classically inspired masterpiece. With 6 bedrooms & 9 bathrooms as well as a paneled library, staff quarters, movie screening & recreation rooms, the home displays a blend of classic design & the finest craftsmanship. Fine materials & finishes distinguish the home, further refined by vaulted

    Todd David Miller William Raveis Real Estate

    2 Broadview Rd, Westport, CT 06880
  • 78 Sylvan Rd N, Westport, CT 06880

    $4,080,000 Sold Aug 22, 2024

    • 7,987 Sq Ft
    • $511/SF
    • 49 Days On Market
    • 5 Beds
    • 8 Baths
    • Built 2024

    78 Sylvan Rd N, Westport, CT 06880

    Step into luxury with this remarkable modern colonial, featuring 5-bedrooms, 6-full bathrooms, and 2 half baths. Meticulously designed and crafted to perfection by Epoch Homes, this home sits in close proximity to major commuting lines as well as downtown Westport. European windows flood the home with natural light. The gourmet kitchen boasts custom cabinetry, high-end appliances, and sleek

    Kasia Babinski William Raveis Real Estate

    78 Sylvan Rd N, Westport, CT 06880
  • 33 Grassy Plains Rd, Westport, CT 06880

    $2,100,000 Sold Aug 21, 2024

    • 4,371 Sq Ft
    • $480/SF
    • 104 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 2014

    33 Grassy Plains Rd, Westport, CT 06880

    Explore this custom Nantucket-style home nestled in the private Reserve at Poplar Plains community. Absolutely gorgeous home brimming with sophistication, set at the end of a cul-de-sac of similarly impressive homes, this home boasts gorgeous views of the 33-acre conservation, with easy accessibility to the Merritt, I-95, downtown, train or the Compo beach. The open floor-plan with 9 feet

    Anshu Chawla Brown Harris Stevens

    33 Grassy Plains Rd, Westport, CT 06880
  • 14 Pequot Trail, Westport, CT 06880

    $3,501,000 Sold Aug 19, 2024

    • 4,421 Sq Ft
    • $792/SF
    • 17 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1962

    14 Pequot Trail, Westport, CT 06880

    Widely regarded as having the best view on Nash Pond, 14 Pequot Trail will charm you with modern elegance inside and magazine-worthy spaces outside. This immaculate, extensively renovated home on a beautifully manicured acre offers 4,400 sq ft +/- of comfort and style, optimized to fully enjoy the tranquil backyard waterfront. Masterful design with custom millwork encompasses 3-4 bedrooms,

    Jenny Bentley The Riverside Realty Group

    14 Pequot Trail, Westport, CT 06880
  • 7 Indian Point Ln, Westport, CT 06880

    $2,205,000 Sold Aug 15, 2024

    • 3,498 Sq Ft
    • $630/SF
    • 10 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1948

    7 Indian Point Ln, Westport, CT 06880

    Welcome to this exquisite Mid-Century Modern home, nestled on a private acre in the highly sought-after Old Hill neighborhood. This serene retreat is situated down a quiet drive off of a cul-de-sac, offering the perfect blend of privacy and convenience, walkable to many amenities, and minutes to town, train and schools. The gracious foyer leads to an open floorplan with sitting area, large

    Jen Kass Higgins Group Bedford Square

    7 Indian Point Ln, Westport, CT 06880
  • 6 Stonybrook Rd, Westport, CT 06880

    $4,628,834 Sold Aug 01, 2024

    • 8,957 Sq Ft
    • $517/SF
    • 93 Days On Market
    • 6 Beds
    • 8 Baths
    • Built 2011

    6 Stonybrook Rd, Westport, CT 06880

    Nestled in the heart of Old Hill, this magnificent residence seamlessly blends storied history with modern elegance. Designed to incorporate the original 1769 barn that once graced the property this 6-bedroom home, completed in 2012, features a professional-grade indoor squash court with a soaring 22' ceiling and glass encasement. The private sports sanctuary, complete with a basketball net,

    Meredith Kamo Compass Connecticut, LLC

    6 Stonybrook Rd, Westport, CT 06880
  • 95 Partrick Rd, Westport, CT 06880

    $1,575,000 Sold Jul 18, 2024

    • 2,058 Sq Ft
    • $765/SF
    • 10 Days On Market
    • 2 Beds
    • 3 Baths
    • Built 1933

    95 Partrick Rd, Westport, CT 06880

    Nestled on a sprawling 1.3-acre lot, this charming, sun filled 2/3 bedroom, 3 bathroom, 2,058 sq ft home is complemented by high ceilings with exposed beams, open floor plan, and generously sized rooms creating a spacious and inviting atmosphere. The storybook gardens and renovated in-ground pool, set the stage for a serene outdoor living experience making it perfect for entertaining. The gazebo,

    Brett Lieberman The Riverside Realty Group

    95 Partrick Rd, Westport, CT 06880
  • 7 Ridgewood Ln, Westport, CT 06880

    $3,625,000 Sold Jul 16, 2024

    • 6,680 Sq Ft
    • $543/SF
    • 13 Days On Market
    • 7 Beds
    • 8 Baths
    • Built 2024

    7 Ridgewood Ln, Westport, CT 06880

    Tucked away on a serene, country lane, in the prestigious Old Hill section of Westport, this ready to go, NEW CONSTRUCTION home combines timeless elegance with modern comfort. 7 bedrooms/6 full and 2 half baths, 1st floor office and additional WFH spaces, this residence is finished on all 4 floors and is ideal for both living and working. Walk to Main Street and minutes to the train, and all town

    Lori Popkin Coldwell Banker Realty

    7 Ridgewood Ln, Westport, CT 06880
  • 11 Crawford Rd, Westport, CT 06880

    $1,895,000 Sold Jul 12, 2024

    • 4,304 Sq Ft
    • $440/SF
    • 28 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1956

    11 Crawford Rd, Westport, CT 06880

    Nestled in the sought after neighborhood of Old Hill on over 2 lush acres, this 4 BR, 4 BA expanded cape offers both privacy and convenience. The space above the garage can be utilized as a bedroom with a full bath, au pair or in-law/guest suite, home office or gym. The finished lower level adds additional versatility, making it suitable for a playroom, exercise room, or any other specific needs.

    Gina Hackett Compass Connecticut, LLC

    11 Crawford Rd, Westport, CT 06880
  • 60 Wilton Rd Unit Penthouse 4C, Westport, CT 06880
    60 Wilton Rd Unit Penthouse 4C, Westport, CT 06880
    60 Wilton Rd Unit Penthouse 4C, Westport, CT 06880
    /35

    $3,500,000 Sold Jul 01, 2024

    • 2,437 Sq Ft
    • $1436/SF
    • 266 Days On Market
    • 2 Beds
    • 3 Baths
    • Built 2023

    60 Wilton Rd Unit Penthouse 4C, Westport, CT 06880

    Nestled along the Saugatuck River comes a collection of twelve refined, private homes designed by critically acclaimed architecture firm Roger Ferris + Partners. Bankside House, built by award winning Westport developer David Adam Realty in partnership with Urbane NewHaven, provides home-owners with an exciting opportunity to enjoy all the benefits of living in Downtown Westport, without any of

    Kim Harizman Compass Connecticut, LLC

    60 Wilton Rd Unit Penthouse 4C, Westport, CT 06880
  • 14 Side Hill Rd, Westport, CT 06880

    $1,995,107 Sold Jun 17, 2024

    • 4,204 Sq Ft
    • $475/SF
    • 11 Days On Market
    • 6 Beds
    • 4.5 Baths
    • Built 1959

    14 Side Hill Rd, Westport, CT 06880

    Beautifully situated on the aptly named Side Hill Road in the Old Hill neighborhood, this sprawling Colonial boasts 6 bedrooms, 4.5 baths, a heated pool, over 4200 sqft of spacious living areas and stunning multi level property for privacy and play. Through the grand, double door entry a welcoming foyer draws you into the formal living room with a wood burning fireplace and a full wall of windows

    Leslie Clarke Compass Connecticut, LLC

    14 Side Hill Rd, Westport, CT 06880
  • 65 Woodside Ave, Westport, CT 06880

    $4,150,000 Sold Jun 14, 2024

    • 7,560 Sq Ft
    • $549/SF
    • 158 Days On Market
    • 6 Beds
    • 8 Baths
    • Built 2021

    65 Woodside Ave, Westport, CT 06880

    The perfect Westport location, 5 minutes from the train, schools & shops in this better-than-new construction in Old Hill. The WOW factor is evident throughout this exquisitely detailed home offering the ultimate in luxurious living and state of the art technology. Featuring clean line interiors, this home was built for today's lifestyle with wide open spaces, oversized doorways and abundant

    Susan Lieberman The Riverside Realty Group

    65 Woodside Ave, Westport, CT 06880
  • 7 Tanglewood Ln, Westport, CT 06880

    $1,475,000 Sold May 31, 2024

    • 3,492 Sq Ft
    • $422/SF
    • 44 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1939

    7 Tanglewood Ln, Westport, CT 06880

    Rare opportunity in the prime Old Hill area of Westport. Warm and inviting 5 Bedroom, 3.5 Bath European inspired Colonial sited on a picturesque level acre with a gunite pool at the end of a quiet cul-de-sac. Featuring a perfect floor plan with lots of natural light and well-proportioned rooms, this home is comfortable and spacious, with unique charm throughout. The large foyer leads to an

    Patricia Shea Coldwell Banker Realty

    7 Tanglewood Ln, Westport, CT 06880
  • 1 Ivy Knoll, Westport, CT 06880

    $1,580,000 Sold May 30, 2024

    • 3,338 Sq Ft
    • $473/SF
    • 22 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1963

    1 Ivy Knoll, Westport, CT 06880

    Warm and inviting 4 Bedroom, 2.5 Bath well maintained Colonial sited on a picturesque level acre on a convenient cul-de-sac near town. Featuring a perfect floor plan with lots of natural light and well-proportioned rooms, this home is comfortable and spacious, with unique charm throughout. The foyer leads to an expansive living room with a fireplace, built-ins, and access to a delightful,

    Patricia Shea Coldwell Banker Realty

    1 Ivy Knoll, Westport, CT 06880
  • 15 Newtown Turnpike, Westport, CT 06880

    $1,295,000 Sold May 24, 2024

    • 4,222 Sq Ft
    • $307/SF
    • 64 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1968

    15 Newtown Turnpike, Westport, CT 06880

    Discover this exquisite colonial in Westport's Old Hill, set on 2 acres with stone accents and year-round pond views. The property features an enclosed porch, patio, and large fenced backyard with an underground sprinkler, embodying suburban charm. Offering five bedrooms and 3.5 baths, with the flexibility of a main-floor bedroom being currently used as a home office, this home has space for

    Cynde Koritzinsky William Pitt Sotheby's Int'l

    15 Newtown Turnpike, Westport, CT 06880
  • 60 Wilton Rd Unit 3B, Westport, CT 06880

    $2,700,000 Sold May 24, 2024

    • 2,437 Sq Ft
    • $1108/SF
    • 302 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2023

    60 Wilton Rd Unit 3B, Westport, CT 06880

    Fully completed and ready for occupancy! Unit 3B, on the southwest corner of the building, enjoys water views from the primary bedroom and dining area with tremendous natural light from all 4 exposures. The adjacent 553 square foot terrace, accessed from the foyer, also features views of the Saugatuck River. The terrace is plumbed for a hot tub and outdoor kitchen in addition to being engineered

    Kim Harizman Compass Connecticut, LLC

    60 Wilton Rd Unit 3B, Westport, CT 06880
  • 9 Ludlow Rd Unit A, Westport, CT 06880

    $775,000 Sold Apr 15, 2025

    • 1,150 Sq Ft
    • $674/SF
    • 48 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1988

    9 Ludlow Rd Unit A, Westport, CT 06880

    Wonderful Old Hill Location, walk to elementary school, down town for concerts at the Levitt, The Library, shopping, restaurants and walking trails along riverfront. 2 BR, 2.5 BA condo is a desirable end unit. Living Room has 9' vaulted ceiling and fireplace, with glass door opening to a private patio and small yard, perfect for outdoor entertaining and gardening.The kitchen and dining room are

    Jillian Klaff Coldwell Banker Realty

    9 Ludlow Rd Unit A, Westport, CT 06880
  • 50 Sylvan Rd N, Westport, CT 06880

    $3,750,000 Sold Dec 09, 2024

    • 10,959 Sq Ft
    • $342/SF
    • 482 Days On Market
    • 9 Beds
    • 8.5 Baths
    • Built 1920

    50 Sylvan Rd N, Westport, CT 06880

    Dramatic & inspiring, this 1920's stone & brick Family Compound in Westport's Premier Old Hill Estate Area neighborhood achieves the perfect balance of old world charm, intimacy, and opulence with distinctive custom millwork and modern expensive upgrades throughout. Tucked behind tall privacy stonewalls and iron gates on a beautifully manicured and professionally landscaped 3 acres w/heated

    Jaclyn Picarillo Higgins Group Bedford Square

    50 Sylvan Rd N, Westport, CT 06880
  • 6 Shadbush Ln, Westport, CT 06880

    $1,700,000 Sold Aug 29, 2024

    • 4,123 Sq Ft
    • $412/SF
    • 0 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1965

    6 Shadbush Ln, Westport, CT 06880

    Welcome to this 5/6 bedroom, 4 full/1 half bath home set on a serene parklike property with heated gunite pool and spa. Located in the Old Hill section of Westport, this home provides ample room to spread out with generously sized rooms offering multiple options for work, play, entertaining, and relaxation. Freshly painted with new hardwood floors on the second level and new flooring in the lower

    Brett Lieberman The Riverside Realty Group

    6 Shadbush Ln, Westport, CT 06880

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