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Upton, MA Homes for Sale with Garage

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  • /35

    $749,900

    Open Fri 1PM - 3PM
    • 2 Beds
    • 2 Baths
    • 1,734 Sq Ft

    5 Boot Shop Rd Unit 5, Upton, MA 01568

    Beautiful new construction one-level "Starling" floor plan now available at Cobbler's Creek, a vibrant 55+ community built by exceptional builders with a reputation for excellence! You're welcomed by an open & airy floor plan that seamlessly connects the sunny living room w/fireplace & built-ins, dining rm & kitchen all w/hardwood floors. The kitchen features attractive cabinets with moldings

    Agent Photo

    Jeffrey Germagian

    ERA Key Realty Services-Bay State Group

    5 Boot Shop Rd Unit 5, Upton, MA 01568
  • /37

    $495,000

    • 3 Beds
    • 1 Bath
    • 1,080 Sq Ft

    4 Picadilly St, Upton, MA 01568

    Welcome to this 3-bedroom split-level home offering a wonderful opportunity to build equity and create the home you’ve always envisioned. The main level features a bright living room, a spacious eat-in kitchen with access to the rear deck, and three comfortable bedrooms. The finished lower-level family room provides additional living space ideal for a playroom, home office, media room, or gym. An

    Agent Photo

    Robyn Nasuti

    Realty ONE Group Suburban Lifestyle

    4 Picadilly St, Upton, MA 01568
  • /34

    $799,000

    Open Fri 1PM - 3PM
    • 2 Beds
    • 2 Baths
    • 1,734 Sq Ft

    21 Boot Shop Rd Unit 21, Upton, MA 01568

    Are you looking for low-maintenance single-level living in a thoughtfully designed new construction condo located in an amazing 55+ community? Come check out the "Starling" floor plan at Cobbler's Creek, built by exceptional builders with a reputation for excellence. As you step inside, you're welcomed by an open and airy floor plan that seamlessly connects the sunny living room, dining room &

    Agent Photo

    Jeffrey Germagian

    ERA Key Realty Services-Bay State Group

    21 Boot Shop Rd Unit 21, Upton, MA 01568
  • /23

    $749,900

    Open Fri 1PM - 3PM
    • 2 Beds
    • 2.5 Baths
    • 2,245 Sq Ft

    19 Boot Shop Rd Unit 19, Upton, MA 01568

    Welcome to the fabulous free-standing Blue Bird Model at Cobbler's Creek! Enjoy a distinctive townhouse with 2,200+ square feet of great space easily adaptable to your decor & lifestyle. From a welcoming front porch, enter a foyer with custom moldings & closet open to a spacious open floor plan including a living room & door to a deck, dining area & stylish kitchen w/white cabinets, Quartz

    Agent Photo

    Jeffrey Germagian

    ERA Key Realty Services-Bay State Group

    19 Boot Shop Rd Unit 19, Upton, MA 01568
  • /41

    $855,900

    Open Fri 1PM - 3PM
    • 2 Beds
    • 2.5 Baths
    • 2,228 Sq Ft

    7 Boot Shop Rd Unit 7, Upton, MA 01568

    Come see what's new at Cobbler's Creek, a premier 55+ community of detached condominiums by the renowned Black Brook Realty builder group! Enjoy a Storybook setting of homes nestled in a serene landscape where every day feels like a retreat! The popular "Cardinal" model offers two-story living with everything you need handy on the first floor such as a covered front porch, foyer, powder room,

    The Kattman Team ERA Key Realty Services-Bay State Group

    7 Boot Shop Rd Unit 7, Upton, MA 01568
  • /12

    $989,900

    New Construction
    • 4 Beds
    • 4 Baths
    • 2,990 Sq Ft

    19 W Main St, Upton, MA 01568

    UNDER CONSTRUCTION...Enjoy The Benefits of New Construction with Energy Efficiency & Low Future Maintenance! This stunning home offers the perfect blend of classic elegance and modern convenience with a spacious 1st FLOOR PRIMARY SUITE and laundry and 3 additional bedrooms on the 2nd level. The partially finished basement with finished half bath provides extra square footage plus access to the

    Kim Backlund Northeast Realty + Co.

    19 W Main St, Upton, MA 01568
  • /41

    $1,300,000

    • 4 Beds
    • 3.5 Baths
    • 3,556 Sq Ft

    9 South St, Upton, MA 01568

    Room to grow......inside and out! Expansive 4 bedroom 2 1/2 bath home with separate IN-LAW in finished basement all nestled on a picturesque 8.3 acres! This gem boasts a 2 story foyer, hardwoods throughout the first floor and newer carpet throughout the second floor. Oversized primary suite with cathedral ceiling, large walk-in closet, jacuzzi tub, stand up shower/double vanity. Huge family room

    Robin Haddad Mendon Local Realty

    9 South St, Upton, MA 01568
  • /42

    $2,500,000

    • 4 Beds
    • 5 Baths
    • 4,040 Sq Ft

    117 South St, Upton, MA 01568

    75-Acre Elite Equestrian & Wellness Sanctuary. Ultimate private retreat with a 4,040 SF luxury Cape, world-class horse facilities, and resort backyard. Trail access to West Hill Dam. RESIDENCE: Chef's kitchen (Jade 6-burner, Sub-Zero, granite waterfall island). 1st-floor primary suite with vaulted ceilings & spa bath. 3 upper bedrooms, office, large bonus room + finished walkout lower level.

    Beth Byrne Gibson Sotheby's International Realty

    117 South St, Upton, MA 01568
  • /41

    $1,159,000

    • 4 Beds
    • 2.5 Baths
    • 3,360 Sq Ft

    33 Dairy Dr, Upton, MA 01568

    NEIGHBORHOOD SETTING WITH COMMUTER CONVENIENCE! This North-facing colonial offers over an acre of mature, professionally landscaped yard space that abuts trails and conservation land. Inside, the open layout is anchored by an incredibly spacious family room and modern chef’s kitchen with a double oven, 5-burner gas cooktop and oversized island to use for casual dining eating or as a homework hub.

    Erika Steele REMAX Executive Realty

    33 Dairy Dr, Upton, MA 01568
  • /42

    $899,900

    • 4 Beds
    • 2.5 Baths
    • 2,806 Sq Ft

    10 Sadler Rd, Upton, MA 01568

    Tucked away on a quiet cul-de-sac with 2 acres of wooded bliss, this Federal-front Colonial is pure serenity with an incredibly spacious layout to boot. It's 3000+ square feet that feels warm and homey with New England charm oozing from every room. The kitchen has NEW quartz countertops and a massive eat-in area with a downdraft gas stove. It flows seamlessly into a sun-drenched family room with

    Erika Steele REMAX Executive Realty

    10 Sadler Rd, Upton, MA 01568
  • /7

    $999,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,780 Sq Ft

    17 W Main St, Upton, MA 01568

    UNDER CONSTRUCTION...Enjoy The Benefits of New Construction with Energy Efficiency & Low Future Maintenance! This stunning Colonial offers the perfect blend of classic elegance and modern convenience. Every detail has been carefully selected to provide style and functionality. 1ST floor hardwoods, Quartz countertops and GE Cafe appliances are just a few of the upgraded details that make this home

    Kim Backlund Northeast Realty + Co.

    17 W Main St, Upton, MA 01568
  • /42

    $1,225,000

    $25K PRICE DROP
    • 4 Beds
    • 5.5 Baths
    • 5,736 Sq Ft

    12 Breton Rd, Upton, MA 01568

    With a flexible layout that supports multigenerational living, this gorgeous custom-built colonial has ample space and is situated on 3+ private acres. From the moment you step into the grand two-story foyer adorned w/ granite flooring, you’ll be captivated by the attention to detail & luxurious features throughout, incl 9ft+ ceilings & gleaming hardwoods. Spacious fam rm is a true showpiece w/

    Melissa Ellison Mathieu Newton Sotheby's International Realty

    12 Breton Rd, Upton, MA 01568
  • /36

    $699,900

    $29K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,950 Sq Ft

    87 Shannon Way Unit 86, Upton, MA 01568

    Enjoy low-maintenance living at Upton Ridge, a desirable 55+ community just a short stroll from the renowned Shining Rock Golf Course. This beautiful Milan-style two-story home offers a spacious, thoughtfully designed floor plan featuring a first-floor primary suite and open-concept living. The oversized kitchen is perfect for entertaining, complete with upgraded cabinetry, quartz countertops,

    Shane Brady Keller Williams Realty

    87 Shannon Way Unit 86, Upton, MA 01568
  • /36

    $709,000

    $16K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,950 Sq Ft

    56 Shannon Way Unit 56, Upton, MA 01568

    Welcome to this beautifully maintained two-story townhouse in the highly desirable 55+ Upton Ridge community, where comfort, style, and low-maintenance living come together. Built in 2023 this floor plan features a first-floor primary suite, offering both privacy and ease of living. Upstairs features a generously sized second bedroom with walk in closet, full bath and a spacious second-floor loft

    The Semple and Hettrich Team Coldwell Banker Realty - Sudbury

    56 Shannon Way Unit 56, Upton, MA 01568
  • /28

    $799,000

    Open Fri 1PM - 3PM
    • 2 Beds
    • 2.5 Baths
    • 2,228 Sq Ft

    12 Boot Shop Rd Unit 12, Upton, MA 01568

    New amazing price at Cobbler's Creek, a premier 55+ community of detached condominiums by the renowned Black Brook Realty builder group! Enjoy a Storybook setting of homes nestled in a serene landscape where every day feels like a retreat! The popular "Cardinal" model offers 2-story living with everything you need handy on the 1st floor such as a covered front porch, foyer, powder rm, laundry rm

    The Kattman Team ERA Key Realty Services-Bay State Group

    12 Boot Shop Rd Unit 12, Upton, MA 01568
  • /42

    $519,999

    • 3 Beds
    • 3.5 Baths
    • 2,091 Sq Ft

    13 Knowlton Cir Unit 13, Upton, MA 01568

    Welcome to this WEST-FACING townhouse in the desirable SAMREEN VILLAS community. 13 KNOWLTON CIRCLE offers low-maintenance living in a convenient Upton location.This 3-BEDROOM, 3.5-BATH home features an OPEN-CONCEPT FLOOR PLAN with HARDWOOD FLOORS, a SPACIOUS KITCHEN, and abundant natural light throughout the main living area. The second floor includes THREE GENEROUSLY SIZED BEDROOMS and a LARGE

    Smita Sinha Keller Williams Pinnacle MetroWest

    13 Knowlton Cir Unit 13, Upton, MA 01568
  • /42

    $1,125,000

    $50K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,054 Sq Ft

    35 Howarth Dr, Upton, MA 01568

    Glen Echo is a most desirable neighborhood close to Rt 495, MA Pike & Westborough. This pristine & spacious 4 bedroom, 3.5 bath Chatsworth Model Colonial has been impeccably maintained by its original owners. Enter to dramatic 2 story foyer w/ wainscoting & balcony. Open floor plan, 9 ft ceilings & tons of windows give this home an airy & roomy feel. Main level boasts hardwoods throughout.

    Gerald Simone Mathieu Newton Sotheby's International Realty

    35 Howarth Dr, Upton, MA 01568
  • /41

    $1,125,000

    $74K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,402 Sq Ft

    30 Mendon St, Upton, MA 01568

    30 Mendon St, Upton, MA Experience modern luxury in this newly constructed 2026 single-family home over 3,000 square feet of thoughtfully designed living space. Blending timeless elegance with contemporary comfort, this exceptional residence is crafted for today’s lifestyle. Featuring four spacious bedrooms and four full bathrooms, the home provides both privacy and convenience with high-end

    Luana Velame Century 21 The Real Estate Group

    30 Mendon St, Upton, MA 01568
  • /39

    $675,000

    • 4 Beds
    • 2 Baths
    • 2,534 Sq Ft

    90 Glenview St, Upton, MA 01568

    WOW! This two-family home has had major systems updated in the last two years: Oil-fired boiler w/oil-fired hot water tank, new well pump & piping, all appliances less than 2 years except for one 8-9 year old refrigerator, exterior of fireplace just repointed, updated electrical. Updated windows. First floor unit has a large foyer, generously sized living room with stunning hardwoods and

    Laura Hebb ERA Key Realty Services

    90 Glenview St, Upton, MA 01568
  • /38

    $779,900

    • 2 Beds
    • 2 Baths
    • 1,653 Sq Ft

    41 Rockwood Ln Unit 41, Upton, MA 01568

    Impressive Like New Freestanding Ranch Home in Highly Sought-After Rockwood Meadows Over 55 Community on The Hopkinton Line Just A Few Miles Away From 495/MA Pike Exits. Premium Lot Which Backs up Conservation Area Offering Miles Hiking, Biking and Running Trails. Features an Open Plan With Gorgeous Cherry Cabinet Kitchen, Granite Counters, Stainless Appliances, Center Island and Access to

    Bill Gassett REMAX Executive Realty

    41 Rockwood Ln Unit 41, Upton, MA 01568
  • /42

    $760,000

    $60K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,304 Sq Ft

    11 James Rd, Upton, MA 01568

    Upton Horse Haven: Iconic 3-Bed, 3-Bath Retreat on 3.75 Acres. Discover one of Upton’s most beloved properties, a premier estate where timeless charm meets outdoor living. This home features modern upgrades including 200-amp electrical system, a new oil tank, and town water for seamless reliability. A newly finished basement for entertaining or retreat. Property offers direct access to miles of

    Team ROVI Real Broker MA, LLC

    11 James Rd, Upton, MA 01568
  • /39

    $1,699,000

    $176K PRICE DROP
    • 8 Beds
    • 6 Baths
    • 6,850 Sq Ft

    175 Pleasant St, Upton, MA 01568

    ABSOLUTELY STUNNING. Enormous 8 Bedroom Home with over 6000 square feet of living on 5.5 acres bordering the Shining Rock Golf Course. Privacy abounds on this special property that has been completely updated. Septic System, Roof, Heat/AC, Kitchen, 6 Bathrooms, Windows, Flooring, Well....All NEW. First floor has kitchen, dining room, TWO front to back family/living rooms, full bath, pantry and an

    Matthew Sousa Bullseye Realty Group

    175 Pleasant St, Upton, MA 01568
  • /42

    $1,075,000

    $75K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,924 Sq Ft

    32 Mendon St, Upton, MA 01568

    32 Mendon St, Upton, MA. Where modern sophistication meets timeless design. This newly constructed 2026 residence offers 2,924 square feet of impeccably curated living space, blending contemporary elegance with refined modern farmhouse architecture. Every detail has been intentionally selected — from premium finishes to elevated craftsmanship — creating a home that feels both luxurious and

    Luana Velame Century 21 The Real Estate Group

    32 Mendon St, Upton, MA 01568
  • /41

    $609,900

    • 2 Beds
    • 2.5 Baths
    • 1,810 Sq Ft

    44 Cherry Ln Unit 44, South Grafton, MA 01560

    Welcome to this beautifully maintained Pulte-built townhouse in the desirable Hilltop Farms community! This versatile floor plan features two primary suites—one on each level—ideal for one-level living, guests, or multigenerational living. The kitchen offers oak cabinetry, Corian countertops, LVP flooring, and updated appliances (2019). Enjoy hardwood floors, 9-foot ceilings, a dramatic two-story

    Claire Rainville REMAX Executive Realty

    44 Cherry Ln Unit 44, South Grafton, MA 01560
  • /36

    $3,450,000

    $300K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,014 Sq Ft

    186 Spring St, Hopkinton, MA 01748

    Prime Investment Opportunity: 20.9-Acre Private Estate in Top-Rated Hopkinton School District Nestled on an expansive 20.9-acre wooded lot bordering the Upton State Forest (one of the largest in Hopkinton), 186 Spring Street offers exceptional privacy, tucked deep in the forest with mature trees and natural seclusion. This rare parcel provides significant development potential — including the

    Brendon Sullivan-Monson StartPoint Realty

    186 Spring St, Hopkinton, MA 01748
  • /33

    $600,000

    Open Wed 12PM - 1:30PM
    • 3 Beds
    • 2.5 Baths
    • 1,796 Sq Ft

    17 Tulip Cir Unit 17, South Grafton, MA 01560

    Welcome to condo living at its finest in Grafton’s highly sought-after Hilltop Farms! This beautiful 3BR, 2.5BA townhouse has it all, starting w gorgeous HW floors that flow seamlessly throughout the main level & lots of natural light. The LR has a cozy fireplace perfect for New England winters, & a renovated kitchen that’s a chef’s dream w a large center island, gas cooking & stainless

    Colleen Crowley Lamacchia Realty, Inc.

    17 Tulip Cir Unit 17, South Grafton, MA 01560
  • /41

    $576,800

    $34K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,778 Sq Ft

    46 Tulip Cir Unit 46, South Grafton, MA 01560

    Welcome to this beautiful townhouse in the desirable “Hilltop Farms Community”. Within this appealing property, an open floor plan, a gas fireplace in the living room & hardwood floors.Kitchen with island. This charming 3-bedroom offers 1,778 Sq.Ft. Above-grade living space, plus and additinal approximately 710 Sq.Ft. in finished walkout Basement with sliding door as a family room. Relax in the

    Dalia Izvolsky Century 21 North East

    46 Tulip Cir Unit 46, South Grafton, MA 01560
  • /42

    $550,000

    $20K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    91 Buttercup Ln Unit 91, South Grafton, MA 01560

    Welcome to Hilltop Farm, a serene retreat on a quiet cul-de-sac. This Pulte-built home features a bright, open floor plan with HW floors, crown molding, and a gas fireplace. The upgraded kitchen boasts SS appliances and ample workspace.The 1st-floor primary suite offers a private escape with a tray ceiling and great natural light. Flexible living areas and extra BRs easily accommodate guests or a

    Kiran Kumar Gundavarapu Key Prime Realty LLC

    91 Buttercup Ln Unit 91, South Grafton, MA 01560
  • /42

    $625,000

    $45K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,170 Sq Ft

    204 Sand Trap Ct Unit 204, Northbridge, MA 01534

    Welcome to Shining Rock Golf Club, where luxury living meets breathtaking views. Perfectly situated on the 18th hole directly across from the clubhouse, this upgraded Morgan Plan condo offers an exceptional lifestyle in one of the area's most desirable communities. The custom cherry kitchen features granite, SS appliances and a seamless flow into the DR/LR areas. The spacious first-floor primary

    Katie McBride REMAX Executive Realty

    204 Sand Trap Ct Unit 204, Northbridge, MA 01534
  • /29

    $619,000

    $6K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,558 Sq Ft

    48 Tulip Cir, South Grafton, MA 01560

    Rarely available, this beautifully maintained Jamison-style end unit by Pulte Homes offers the perfect blend of privacy, natural light, and effortless elegance. Tucked against a private wooded backdrop, this luxurious 3-bedroom, 2.5-bath townhouse is a true standout. Step inside to a bright, open floor plan enhanced by designer color palettes and laminate flooring throughout. The eat-in kitchen

    Peter Kim Berkshire Hathaway HomeServices Commonwealth Real Estate

    48 Tulip Cir, South Grafton, MA 01560

Home Price Trends

Median Sale Price
$770,000
Median Single Family Sale Price
$800,000
Median Townhouse Sale Price
$489,999
Median 2 Bedroom Sale Price
$714,500
Average Price Per Sq Ft
$334
Number of Homes for Sale
26
Last 12 months Home Sales
89
Months of Supply
3.50
Median List Price
$789,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
8%
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