Westover Homes for Sale

Welcome to Westover, one of Stamford, Connecticut's most charming neighborhoods, where suburban tranquility meets urban convenience. Nestled in the heart of Fairfield County, Westover is a hidden gem that boasts tree-lined streets, picturesque parks, and a strong sense of community. Known for its spacious lots and beautiful homes, this neighborhood is ideal for families, professionals, and anyone seeking a peaceful retreat just minutes from the bustling city center.

Westover offers a delightful mix of architectural styles, from classic colonials to contemporary designs, ensuring there’s something for everyone. Each property reflects the character of the area, often set against lush backdrops and well-maintained gardens. With homes for sale in various price ranges, you’ll find an array of options that cater to diverse lifestyles and preferences.

Living in Westover means enjoying the best of both worlds. Residents benefit from easy access to Stamford's vibrant downtown, where you can explore an array of dining, shopping, and entertainment options. The neighborhood is also conveniently located near major highways and public transportation, making commutes a breeze. For those who appreciate the outdoors, nearby parks and recreational facilities provide ample opportunities for hiking, biking, and family picnics.

In Westover, community spirit thrives, with friendly neighbors and local events that foster connections. Whether you’re looking for a place to raise a family, downsize, or simply invest in a beautiful home, Westover is a neighborhood that welcomes you with open arms. Discover your dream home in this delightful enclave today!

Newest Westover Homes for Sale

$2,295,000

6 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24204113 MLS

Experience refined luxury in this expansive Westover residence, privately nestled at the end of a tranquil drive and moments from premier schools, major highways, transportation, and the exceptional amenities of Stamford and Greenwich. Surrounded by lush, mature landscaping with access to the beauty of Mianus River Park, this move-in-ready home offers a rare blend of privacy, sophistication, and convenience. Designed for elegant entertaining and effortless everyday living, the residence features a gourmet chef's kitchen with an exquisite butler's pantry flowing seamlessly into gracious open-concept living spaces. French doors open to an expansive west-facing deck, perfectly positioned for spectacular sunset views, while a sun-drenched patio just off the kitchen creates a seamless indoor-outdoor lifestyle. The luxurious main-level primary suite offers exceptional privacy and scale, with dual walk-in closets and a spa-inspired bath featuring a Jacuzzi tub. Upstairs, four generously sized bedrooms include two en-suite bedrooms and two sharing a bath. The extraordinary walk-out lower level provides a private en-suite guest suite, spacious office, and expansive recreation room anchored by a dramatic stone fireplace. Thoughtfully curated throughout, this exceptional residence delivers timeless elegance, comfort, and privacy in a coveted Westover setting.

46 Old Mill Ln, Stamford

$1,975,000

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24203285 MLS

A Westover Masterpiece of Luxury, Comfort & Style. Set in one of Stamford's most sought-after neighborhoods, this exceptional residence offers a rare combination of timeless elegance, sophisticated updates, and effortless everyday living. Once owned by renowned basketball player and coach Doc Rivers, the home has been thoughtfully enhanced while retaining its grand architectural character. From the moment you enter the dramatic two-story foyer, the sweeping staircase and stunning crystal chandelier make an unforgettable impression. The chandelier is thoughtfully mounted on a lift, allowing it to be conveniently lowered for cleaning: a perfect example of the home's attention to both beauty and practicality. The recently remodeled kitchen is elegant yet inviting, with three skylights, top-of-the-line appliances, and an open connection to the comfortable family room. A stone fireplace anchors the family room, while expansive views extend to the large deck and patio and the beautiful, heated in-ground gunite pool. Re-plastered in 2025 and equipped with an automatic cover, it creates an exceptional private setting for summer fun. You will love entertaining guests in the fully fenced back yard and on the expansive deck and patio. A full house generator offers peace of mind.

97 Brookhollow Ln, Stamford

$1,075,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24200831 MLS

Welcome to Your Westover Oasis! Set on a quiet, tree-lined street in one of Stamford's most desirable neighborhoods, this inviting 3-bedroom, 3-bath Ranch offers easy living, wonderful indoor-outdoor spaces, and a fabulous pool setting. The main level is open and airy, featuring a spacious Living Room with gas fireplace, lovely Dining Room overlooking the beautiful yard and pool, and a granite-and-stainless Eat-In Kitchen with entry to the Deck. The bedroom wing includes a generous Primary Bedroom with walk-in closet & private bath with double vanity, heated floors & steam shower, two additional Bedrooms-one en-suite-and a Full Hall Bath. The walk-out lower level adds exceptional living space with a comfortable Family Room featuring a brick fireplace with wood-stove insert, wet bar, and sliders to the Patio and yard. An expansive Office, Laundry, and generous Storage/Pool Room complete the lower level. Step outside and discover your own private oasis! The fully fenced yard with sprinkler system centers around a heated pool, creating the perfect gathering spot while still offering plenty of lawn for play and relaxation. Mature plantings and thoughtfully designed landscaping provide privacy and enhance the peaceful setting. Ideally located in Westover, you're just minutes from commuting routes, shopping, dining, and all the restaurants, entertainment, and waterfront attractions of Downtown Stamford and Harbor Point. A wonderful home in a truly special setting-welcome home

45 Hemlock Dr, Stamford

$1,530,000

5 Beds ⋅ 4 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24199719 MLS

A home of enduring beauty and remarkable provenance, Roxbury Rose is a rare offering that celebrates the craftsmanship and character of a bygone era. Believed to be one of Westover's original farmhouses, this distinguished 1860 Greek Revival Colonial has been thoughtfully preserved while embracing the comforts of modern living. Rich in authentic architectural detail, the residence is defined by soaring ceilings, five original fireplaces, wide-board pumpkin pine floors, handcrafted millwork, and warm brick passageways that create an atmosphere both elegant and inviting. An award winning, architecturally faithful addition seamlessly expands the home's living spaces, honoring its historic integrity while providing exceptional scale for today's lifestyle. Set amid 1.22 acres of beautifully landscaped grounds with mature specimen trees, Roxbury Rose offers over 5,300 sf of timeless living where every room tells a story. More than a residence, it is a legacy property that preserves the romance of New England's past while offering an extraordinary setting for generations yet to come.

530 Roxbury Rd, Stamford

$1,900,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24199455 MLS

Modern Sophistication Meets Suburban Serenity in Westover - Tucked away on a tranquil cul-de-sac, this recently built architectural gem offers a masterclass in modern living, blending refined elegance with the vibrant energy of nearby downtown Stamford. The residence unfolds through a dramatic two-story foyer into a sun-drenched, open-concept sanctuary, where a chef-inspired kitchen-adorned with pristine white cabinetry and expansive granite surfaces-flows effortlessly into a fireside living room and adjacent sunroom with French doors leading outside. The outdoor experience is truly peerless, featuring a resort-style saltwater pool with waterfall, a professional-grade basketball/sports court, and a sprawling bluestone patio framed by artisanal rock walls and secure perimeter fencing. With a high-efficiency infrastructure, vast expansion potential in the walk-out basement, and a commute to Manhattan in under an hour, this property represents a rare opportunity to enjoy "like-new" luxury and a private backyard oasis without the wait.

47 Summit Ridge Rd, Stamford

$1,425,000

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24196442 MLS

Nestled at the end of one of Westover's most sought after cul-de-sacs, this exceptional five bedroom residence offers the perfect blend of privacy, elegance, and convenience. Ideally positioned on the Greenwich border, you'll enjoy quick access to downtown Stamford, Metro North, and vibrant downtown Greenwich, while returning home to a peaceful, secluded setting surrounded by nature. Designed with both entertaining and gracious everyday living in mind, the thoughtfully crafted floor plan offers spacious, light filled rooms and an effortless flow throughout. The expansive deck serves as a true outdoor retreat, providing exceptional privacy and generous space for hosting summer gatherings, dining alfresco, or simply relaxing while overlooking the tranquil surroundings. The main level features a separate and private bedroom with an adjacent full bath, creating the perfect accommodations for guests, au pair, or for multigenerational living. Upstairs, the luxurious primary suite is a sanctuary all its own. The dramatic vaulted beamed ceiling, a stunning Palladian window, and three oversized closets create an impressive yet inviting space. The spa inspired primary bath offers a whirlpool tub, a walk-in shower, and the comfort of a private retreat at the end of each day. Located in one of Stamford's, most desirable neighborhoods, this home combines timeless style, exceptional privacy, and an unbeatable location to create a truly remarkable place to call home.

89 W Bank Ln, Stamford

$999,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24193896 MLS

Set on 1.5 picturesque acres in Stamford's desirable Westover neighborhood, this sprawling ranch offers comfortable living surrounded by a pond, and mature perennial gardens. The main level features a spacious eat-in kitchen with stainless steel appliances, a formal dining room, a private office, and a light-filled living room with hardwood floors, a fireplace with a custom mantel, and a large bay window overlooking the grounds. The primary bedroom suite includes its own full bathroom, while two additional bedrooms and another full bathroom complete the main level. The finished walkout lower level provides additional living space with a kitchenette and full bathroom, offering flexibility for guests, a potential in-law setup, or everyday use. A large deck overlooking the scenic backyard creates an inviting setting for relaxing and entertaining. Additional highlights include central air, a two-car garage, and a convenient location near shopping, parks, downtown Stamford, Metro-North, and major commuter routes.

207 Barncroft Rd, Stamford

$950,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24191783 MLS

Thoughtfully designed for both comfortable everyday living and effortless entertaining, this spacious home offers an inviting layout and a backyard setting overlooking the E. Gaynor Brennan Golf Course. A dramatic two-story foyer greets you upon entry and leads to a formal living room and formal dining room. Adjacent to the dining room, the large kitchen features a center island, breakfast nook, and overlooks the backyard and golf course beyond. The kitchen opens seamlessly to an expansive family room with a fireplace, creating a natural gathering space, while two powder rooms complete the main level. Upstairs, the generously sized primary bedroom suite includes a spa-like bathroom, complemented by three additional bedrooms and two full bathrooms. The lower level offers a large rec room, wine room, additional storage space, and a convenient mudroom with direct access to the attached two-car garage with an EV charger. Step outside to a private backyard retreat featuring a hot tub, providing the perfect place to unwind while overlooking the golf course. Ideally located, and just minutes from shopping, restaurants, parks, Metro-North, and major commuter routes.

387 Stillwater Ave, Stamford

$2,195,000

6 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24156764 MLS

Rare 3.75-Acre Builder Opportunity on W Hill Road Exceptional opportunity to own 3.75 private acres in one of the area's most prestigious and sought-after locations-W Hill Road. This unique property features an existing 4,400 sq ft main residence plus a separate 900 sq ft cottage, offering endless possibilities for builders, investors, or end-users seeking a private estate setting. The current home presents a prime rehab opportunity with substantial square footage, solid footprint, and the potential to transform into a luxury showpiece. The detached cottage is ideal for guest quarters, rental income, or on-site living during construction. For developers, the expansive parcel offers subdivision potential to create up to three additional home sites. Surrounded by high-end properties and set in an enclave, this is a rare chance to build new luxury homes in a premier location with strong resale value. land, privacy, and prime positioning make this a standout investment. Endless possibilities - renovate, build new, or develop. Opportunities like this on W Hill Road are few and far between. Tenant-occupied. Please do not walk the property or disturb tenants. All showings require confirmed appointment .Tenant-occupied. Please do not walk the property or disturb tenants. All showings require confirmed appointment

677 W Hill Rd, Stamford

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